#------------------------------------------------------------------------------ #$Date: 2020-05-28 06:49:21 +0300 (Thu, 28 May 2020) $ #$Revision: 252428 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157517.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7157517 loop_ _publ_author_name 'Martinez Bulit, Pablo' 'Wilson, Benjamin H.' 'Loeb, Stephen J.' _publ_section_title ; One-pot synthesis of porphyrin-based [5]rotaxanes ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00906G _journal_year 2020 _chemical_formula_moiety 'C96 H96 N8 O16, 3(B2 F8), 4(C24 H32 O8)' _chemical_formula_sum 'C192 H224 B6 F24 N8 O48' _chemical_formula_weight 3932.64 _chemical_name_systematic '[5]rotaxane' _space_group_crystal_system tetragonal _space_group_IT_number 86 _space_group_name_Hall '-P 4bc' _space_group_name_H-M_alt 'P 42/n :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-04-29 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-04-29 deposited with the CCDC. 2020-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 25.0521(11) _cell_length_b 25.0521(11) _cell_length_c 15.1716(18) _cell_measurement_reflns_used 7197 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 66.8500 _cell_measurement_theta_min 2.4510 _cell_volume 9521.8(13) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 193.23 288.23 1.00 75.00 -- -88.38 -59.86 110.31 95 2 \w -134.58 -25.58 1.00 75.00 -- -103.38 84.78 59.60 109 3 \w -11.09 81.91 1.00 75.00 -- 4.61 59.85 -20.31 93 4 \f 13.54 250.54 1.00 75.00 -86.12-103.38 -59.16 -- 237 5 \f 71.67 299.67 1.00 75.00 -23.88-103.38 30.17 -- 228 6 \f 91.67 240.67 1.00 75.00 -3.05 5.65 30.17 -- 149 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0430431000 _diffrn_orient_matrix_UB_12 -0.0423501000 _diffrn_orient_matrix_UB_13 0.0192231000 _diffrn_orient_matrix_UB_21 0.0434462000 _diffrn_orient_matrix_UB_22 -0.0433310000 _diffrn_orient_matrix_UB_23 0.0048268000 _diffrn_orient_matrix_UB_31 0.0061988000 _diffrn_orient_matrix_UB_32 0.0102779000 _diffrn_orient_matrix_UB_33 0.0996931000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_Laue_measured_fraction_full 0.981 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 38551 _diffrn_reflns_point_group_measured_fraction_full 0.981 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 50.412 _diffrn_reflns_theta_max 50.412 _diffrn_reflns_theta_min 2.494 _diffrn_source 'I\mS Microfocus Source' _exptl_absorpt_coefficient_mu 0.957 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic green' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.372 _exptl_crystal_description plate _exptl_crystal_F_000 4124 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile - isopropyl ether' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.096 _exptl_crystal_size_min 0.074 _refine_diff_density_max 0.573 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.096 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.677 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 656 _refine_ls_number_reflns 4886 _refine_ls_number_restraints 611 _refine_ls_restrained_S_all 1.654 _refine_ls_R_factor_all 0.2752 _refine_ls_R_factor_gt 0.1892 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.4626 _refine_ls_wR_factor_ref 0.5216 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2121 _reflns_number_total 4886 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00906g2.cif _cod_data_source_block cu_pb029_3 _cod_original_cell_volume 9521.8(14) _cod_original_sg_symbol_H-M 'P 42/n' _cod_database_code 7157517 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C50 H40 N2 O10 B F4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.933 _shelx_estimated_absorpt_t_min 0.724 _reflns_odcompleteness_completeness 99.99 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances F4-B1 1.402 with sigma of 0.02 F1-B1 1.402 with sigma of 0.02 F2-B1 1.402 with sigma of 0.02 F3-B1 1.402 with sigma of 0.02 B2-F5 1.402 with sigma of 0.02 F6A-B2 1.402 with sigma of 0.02 B2-F8A 1.402 with sigma of 0.02 B2-F6B 1.402 with sigma of 0.02 B2-F7B 1.402 with sigma of 0.02 F8B-B2 1.402 with sigma of 0.02 F7A-B2 1.402 with sigma of 0.02 F7A-F8A 2.21 with sigma of 0.02 F8A-F6A 2.21 with sigma of 0.02 F6A-F7A 2.21 with sigma of 0.02 F5-F7A 2.21 with sigma of 0.02 F8A-F5 2.21 with sigma of 0.02 F6A-F5 2.21 with sigma of 0.02 F8B-F7B 2.21 with sigma of 0.02 F7B-F6B 2.21 with sigma of 0.02 F6B-F8B 2.21 with sigma of 0.02 F8B-F5 2.21 with sigma of 0.02 F6B-F5 2.21 with sigma of 0.02 F7B-F5 2.21 with sigma of 0.02 C24A-C23 1.4 with sigma of 0.02 C24B-C23 1.4 with sigma of 0.02 C24A-O4 2.4 with sigma of 0.02 C24B-O4 2.4 with sigma of 0.02 C47-O12 1.36 with sigma of 0.02 C47-C48 1.395 with sigma of 0.02 O5-C48 1.5 with sigma of 0.02 F7B-H27_$1 -2.2 with sigma of 0.02 F3-H24A -2.2 with sigma of 0.02 F4-H24F -2.2 with sigma of 0.02 F3-H24C -2.2 with sigma of 0.02 H24B-F3 -2.2 with sigma of 0.02 H47A-F8B -2.2 with sigma of 0.02 H47B-F8B -2.2 with sigma of 0.01 H24E-F4 -2.2 with sigma of 0.02 C20-C21 1.4 with sigma of 0.02 C31-C32 1.4 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints C24A \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(F6B) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(C24A) \\sim Ueq, Uanis(C24B) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(C21) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(F6A) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08 4. Rigid body (RIGU) restrains C44, O10, C43, C42, C37, C41, O9, C38, O11, C40, C36, C39, C45, C35, C46, O8, C34, O12, C33, O7, C32, C31, O6, C30, C25, C29, C26, O5, C28, C27, C48, C47 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 F2, B1, F4, F3, F1 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 F6A, F8A, F5, B2, F7A with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 F8B, B2, F5, F7B, F6B with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 C7, N1, H1, C1, C4, C2, C5, C3, H2, C6, H3, C11, C10, H11, H7, C8, C9, H10, H8, C12, N2, H2A, H2B, C13, C18, C14, H18, C17, H14, C15, C16, C22, C19, H16, O4, O3, O2, O1, C23, C20, C24B, C24A, C21, H20A, H20B, H21A, H21B, H21C with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Fixed Sof: F3(0.5) F8A(0.5) F4(0.5) F6B(0.5) F6A(0.5) F7B(0.5) H23C(0.5) H23D(0.5) H23A(0.5) H23B(0.5) C24B(0.5) H24A(0.5) H24B(0.5) H24C(0.5) B1(0.5) F8B(0.5) F7A(0.5) C24A(0.5) H24D(0.5) H24E(0.5) H24F(0.5) 6.a Secondary CH2 refined with riding coordinates: N2(H2A,H2B), C32(H32A,H32B), C12(H12A,H12B), C43(H43A,H43B), C33(H33A,H33B), C36(H36A,H36B), C34(H34A,H34B), C46(H46A,H46B), C31(H31A,H31B), C48(H48A,H48B), C47(H47A,H47B), C23(H23C,H23D), C23(H23A,H23B), C44(H44A,H44B), C35(H35A, H35B), C45(H45A,H45B), C20(H20A,H20B) 6.b Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C3(H3), C26(H26), C27(H27), C28(H28), C29(H29), C10(H10), C11(H11), C7(H7), C8(H8), C18(H18), C16(H16), C14(H14), C38(H38), C39(H39), C40(H40), C41(H41) 6.c Fitted hexagon refined as free rotating group: C30(C25,C26,C27,C28,C29), C42(C37,C38,C39,C40,C41) 6.d Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C24B(H24A,H24B,H24C), C24A(H24D,H24E,H24F) ; _shelx_res_file ; TITL cu_pb029_3_a.res in P4(2)/n cu_pb029_3.res created by SHELXL-2018/3 at 12:27:09 on 29-Apr-2020 REM Old TITL cu_PB029_3 in P4(2)/n REM SHELXT solution in P4(2)/n: R1 0.427, Rweak 0.193, Alpha 0.138 REM 0.306 for 243 systematic absences, Orientation as input REM Formula found by SHELXT: C205 B4 N24 O2 F6 CELL 1.54184 25.0521 25.0521 15.1716 90 90 90 ZERR 2 0.0011 0.0011 0.0018 0 0 0 LATT 1 SYMM 0.5-X,0.5-Y,+Z SYMM -Y,0.5+X,0.5+Z SYMM 0.5+Y,-X,0.5+Z SFAC C H B F N O UNIT 384 448 12 48 16 96 EQIV $1 0.5-X,1.5-Y,+Z DFIX 1.402 F4 B1 DFIX 1.402 F1 B1 DFIX 1.402 F2 B1 DFIX 1.402 F3 B1 DFIX 1.402 B2 F5 DFIX 1.402 F6A B2 DFIX 1.402 B2 F8A DFIX 1.402 B2 F6B DFIX 1.402 B2 F7B DFIX 1.402 F8B B2 DFIX 1.402 F7A B2 DFIX 2.21 F7A F8A DFIX 2.21 F8A F6A DFIX 2.21 F6A F7A DFIX 2.21 F5 F7A DFIX 2.21 F8A F5 DFIX 2.21 F6A F5 DFIX 2.21 F8B F7B DFIX 2.21 F7B F6B DFIX 2.21 F6B F8B DFIX 2.21 F8B F5 DFIX 2.21 F6B F5 DFIX 2.21 F7B F5 DFIX 1.4 C24A C23 DFIX 1.4 C24B C23 DFIX 2.4 C24A O4 DFIX 2.4 C24B O4 DFIX 1.36 C47 O12 DFIX 1.395 C47 C48 DFIX 1.5 O5 C48 DFIX -2.2 F7B H27_$1 DFIX -2.2 F3 H24a DFIX -2.2 F4 H24f DFIX -2.2 F3 H24c DFIX -2.2 H24b F3 DFIX -2.2 H47a F8B DFIX -2.2 0.01 H47b F8B DFIX -2.2 H24e F4 DFIX 1.4 C20 C21 DFIX 1.4 C31 C32 SIMU 0.04 0.08 1.7 C24A C23 RIGU C44 O10 C43 C42 C37 C41 O9 C38 O11 C40 C36 C39 C45 C35 C46 O8 C34 O12 = C33 O7 C32 C31 O6 C30 C25 C29 C26 O5 C28 C27 C48 C47 RIGU F2 B1 F4 F3 F1 RIGU F6A F8A F5 B2 F7A RIGU F8B B2 F5 F7B F6B RIGU C7 N1 H1 C1 C4 C2 C5 C3 H2 C6 H3 C11 C10 H11 H7 C8 C9 H10 H8 C12 N2 = H2A H2B C13 C18 C14 H18 C17 H14 C15 C16 C22 C19 H16 O4 O3 O2 O1 C23 C20 = C24B C24A C21 H20A H20B H21A H21B H21C ISOR 0.04 0.08 F6B ISOR 0.04 0.08 C24A C24B ISOR 0.04 0.08 C21 ISOR 0.04 0.08 F6A L.S. 99 PLAN 20 SIZE 0.074 0.096 0.36 TEMP -100(2) BOND list 4 fmap 2 53 acta SHEL 55 1 OMIT 0 2 0 OMIT 0 2 2 OMIT 3 4 1 OMIT -2 15 1 OMIT 1 8 1 OMIT -2 8 0 OMIT 2 5 1 OMIT 1 5 0 OMIT 1 7 0 OMIT -4 9 5 OMIT 8 12 1 OMIT 0 7 4 OMIT 4 9 1 OMIT 3 15 3 OMIT -4 5 6 OMIT 7 7 8 OMIT 4 5 1 OMIT -1 3 2 OMIT -3 4 1 OMIT -7 10 5 OMIT 1 3 5 OMIT -8 15 3 OMIT -6 8 4 OMIT 6 8 6 OMIT 2 7 1 OMIT 5 15 2 OMIT 3 3 3 OMIT 0 18 2 OMIT 6 14 0 OMIT 9 13 0 OMIT 2 2 0 OMIT -11 17 0 OMIT 0 1 1 OMIT 1 10 3 OMIT 5 13 0 OMIT 1 4 1 OMIT 4 11 1 OMIT 2 8 2 OMIT -3 5 2 OMIT 0 6 8 OMIT 0 13 2 OMIT -11 15 0 OMIT 4 18 3 OMIT -3 14 2 OMIT -1 6 7 OMIT 4 21 1 OMIT 3 14 6 OMIT 7 12 1 OMIT 12 12 1 OMIT -7 8 1 OMIT 5 5 2 OMIT 2 2 2 OMIT 3 17 0 OMIT -4 6 1 OMIT 1 3 4 OMIT 4 8 0 OMIT -5 12 3 OMIT -5 17 3 OMIT 0 8 4 OMIT -1 10 1 OMIT 6 8 4 OMIT 4 8 2 OMIT -8 15 1 OMIT 1 11 0 OMIT -3 7 3 OMIT -12 13 1 OMIT 7 11 4 OMIT 3 6 4 OMIT 5 19 0 OMIT -3 5 0 OMIT -3 8 9 OMIT -5 6 1 OMIT -1 5 1 OMIT 5 12 2 OMIT 0 3 4 OMIT 5 17 0 OMIT -7 13 1 OMIT 2 11 1 OMIT -4 7 1 OMIT -8 12 2 OMIT -5 7 0 OMIT -6 15 7 OMIT -4 13 6 OMIT -1 11 8 OMIT 3 7 6 OMIT 4 4 10 OMIT 0 3 5 OMIT -6 20 0 OMIT 6 10 0 OMIT -9 16 1 OMIT 0 12 3 OMIT -1 3 0 OMIT 5 7 6 OMIT -3 5 9 OMIT 7 15 2 OMIT -2 9 5 OMIT 6 15 2 REM REM REM WGHT 0.200000 FVAR 0.15959 N1 5 0.266813 0.332383 0.244268 11.00000 0.07981 0.06093 = 0.14104 0.00382 -0.00442 -0.00167 AFIX 43 H1 2 0.260330 0.299353 0.227679 11.00000 -1.20000 AFIX 0 F1 4 -0.250000 0.750000 -0.116099 10.50000 0.14887 0.14186 = 0.17017 0.00000 0.00000 -0.01233 C1 1 0.317519 0.353344 0.265251 11.00000 0.08992 0.06200 = 0.16198 -0.01044 -0.00954 0.00605 F2 4 -0.250000 0.750000 0.031519 10.50000 0.21161 0.17365 = 0.17272 0.00000 0.00000 0.03186 C4 1 0.229233 0.371809 0.253903 11.00000 0.06717 0.07031 = 0.16960 0.00273 -0.00600 0.00393 C2 1 0.307364 0.406583 0.292430 11.00000 0.08760 0.06139 = 0.23035 -0.00386 -0.00690 -0.00232 AFIX 43 H2 2 0.333270 0.430878 0.314377 11.00000 -1.20000 AFIX 0 C5 1 0.173649 0.365093 0.240308 11.00000 0.08015 0.07895 = 0.11247 -0.00056 -0.00242 0.00399 C6 1 0.141925 0.414619 0.232982 11.00000 0.07035 0.07635 = 0.15204 -0.00232 -0.00216 0.00229 C3 1 0.254916 0.417073 0.282020 11.00000 0.07857 0.07887 = 0.17894 -0.01336 -0.01844 0.00785 AFIX 43 H3 2 0.238353 0.450586 0.292525 11.00000 -1.20000 AFIX 0 O10 6 0.003067 0.574973 0.454947 11.00000 0.21594 0.15324 = 0.27518 0.06199 0.07772 -0.00027 AFIX 66 C30 1 0.105163 0.704097 0.140436 11.00000 0.16980 0.16240 = 0.17086 0.02791 0.02091 -0.05073 C25 1 0.150756 0.697199 0.191392 11.00000 0.14609 0.24595 = 0.18988 0.05146 0.04392 -0.04729 C26 1 0.176912 0.741346 0.226239 11.00000 0.23937 0.31586 = 0.21369 -0.03168 -0.03529 -0.03239 AFIX 43 H26 2 0.208072 0.736631 0.261065 11.00000 -1.20000 AFIX 65 C27 1 0.157477 0.792391 0.210132 11.00000 0.25581 0.27174 = 0.40575 0.00388 0.04937 -0.07443 AFIX 43 H27 2 0.175354 0.822563 0.233949 11.00000 -1.20000 AFIX 65 C28 1 0.111885 0.799290 0.159177 11.00000 0.32945 0.18007 = 0.44983 0.07052 0.01129 -0.00245 AFIX 43 H28 2 0.098602 0.834177 0.148169 11.00000 -1.20000 AFIX 65 C29 1 0.085728 0.755144 0.124329 11.00000 0.30527 0.22671 = 0.24065 0.08692 -0.01833 0.01735 AFIX 43 H29 2 0.054567 0.759859 0.089503 11.00000 -1.20000 AFIX 0 O9 6 -0.072027 0.563523 0.351677 11.00000 0.13956 0.18226 = 0.36414 0.08975 0.03650 -0.00548 C9 1 0.081489 0.507132 0.221653 11.00000 0.09999 0.08893 = 0.20242 -0.01714 -0.03411 0.01996 C10 1 0.069326 0.469620 0.283282 11.00000 0.09763 0.12264 = 0.26487 0.01525 0.02587 0.02820 AFIX 43 H10 2 0.040774 0.475353 0.323388 11.00000 -1.20000 AFIX 0 C11 1 0.098992 0.422917 0.287044 11.00000 0.08779 0.09465 = 0.21955 0.00984 0.03095 0.00448 AFIX 43 H11 2 0.089262 0.396028 0.328171 11.00000 -1.20000 AFIX 0 C7 1 0.156570 0.453933 0.171797 11.00000 0.10115 0.10431 = 0.14991 0.01132 -0.00830 0.02096 AFIX 43 H7 2 0.186254 0.449123 0.133650 11.00000 -1.20000 AFIX 0 C8 1 0.125534 0.500916 0.169044 11.00000 0.13053 0.07967 = 0.20708 0.01040 -0.01247 0.00840 AFIX 43 H8 2 0.135378 0.528828 0.129898 11.00000 -1.20000 AFIX 0 O11 6 0.115533 0.564151 0.435531 11.00000 0.16936 0.22266 = 0.30302 -0.03803 -0.02446 0.04576 C18 1 -0.005307 0.655187 0.252518 11.00000 0.19925 0.09462 = 0.22800 0.00499 0.09187 0.01419 AFIX 43 H18 2 -0.018781 0.629851 0.211583 11.00000 -1.20000 AFIX 0 N2 5 0.065785 0.594995 0.284562 11.00000 0.34775 0.09263 = 0.18981 -0.02807 -0.01856 0.06271 AFIX 23 H2A 2 0.100710 0.601816 0.272521 11.00000 -1.20000 H2B 2 0.065098 0.577629 0.337231 11.00000 -1.20000 AFIX 0 C16 1 -0.009172 0.741586 0.334411 11.00000 0.30833 0.09079 = 0.25864 0.02324 0.14676 0.05868 AFIX 43 H16 2 -0.027033 0.773368 0.351645 11.00000 -1.20000 AFIX 0 C13 1 0.040120 0.647009 0.299062 11.00000 0.21144 0.08674 = 0.23725 0.01028 0.07643 0.02085 C19 1 0.065331 0.769016 0.425771 11.00000 0.49044 0.13610 = 0.14952 -0.03238 0.06442 0.07266 O4 6 -0.102919 0.685034 0.170573 11.00000 0.24241 0.12929 = 0.49404 0.03212 0.04102 0.07322 O6 6 0.084063 0.662247 0.102923 11.00000 0.27478 0.27519 = 0.25170 -0.03099 -0.03491 -0.07942 C17 1 -0.033365 0.708558 0.270990 11.00000 0.25727 0.10991 = 0.28646 0.03815 0.11161 0.05905 O5 6 0.164498 0.648446 0.229288 11.00000 0.16478 0.29837 = 0.91043 0.17531 -0.17591 -0.00497 O2 6 0.109468 0.758311 0.448691 11.00000 0.51064 0.19489 = 0.25625 -0.08631 -0.01344 0.07183 C14 1 0.061313 0.681346 0.353911 11.00000 0.28581 0.09784 = 0.19809 -0.01251 0.05698 0.05231 AFIX 43 H14 2 0.093800 0.671881 0.382176 11.00000 -1.20000 AFIX 0 O8 6 -0.058451 0.519800 0.162977 11.00000 0.12526 0.29064 = 0.43417 0.12605 -0.04817 -0.01939 C32 1 0.037851 0.618941 -0.018467 11.00000 0.28594 0.17742 = 0.30447 0.05281 -0.06551 -0.06036 AFIX 23 H32A 2 0.066606 0.592487 -0.028235 11.00000 -1.20000 H32B 2 0.022160 0.629587 -0.075719 11.00000 -1.20000 AFIX 0 C12 1 0.049219 0.560043 0.224083 11.00000 0.18381 0.11749 = 0.27036 -0.03361 -0.10047 0.05686 AFIX 23 H12A 2 0.051298 0.577100 0.165321 11.00000 -1.20000 H12B 2 0.011266 0.551502 0.235556 11.00000 -1.20000 AFIX 0 C15 1 0.039573 0.729778 0.372831 11.00000 0.33193 0.08430 = 0.23843 0.00536 0.11354 0.04419 O1 6 0.040488 0.807942 0.453595 11.00000 0.55385 0.12723 = 0.25327 -0.03629 0.06385 0.07858 C43 1 0.040831 0.578925 0.535687 11.00000 0.24794 0.35653 = 0.24977 0.11894 0.07373 -0.07424 AFIX 23 H43A 2 0.054648 0.615634 0.543640 11.00000 -1.20000 H43B 2 0.022951 0.567149 0.590533 11.00000 -1.20000 AFIX 0 O3 6 -0.106751 0.763100 0.229145 11.00000 0.40005 0.14607 = 0.64758 -0.00459 -0.01050 0.15940 O7 6 -0.007373 0.597167 0.050565 11.00000 0.42269 0.40385 = 0.40650 -0.01875 0.00577 -0.25774 C33 1 -0.032732 0.559165 0.032417 11.00000 0.25858 0.24171 = 0.30091 -0.11215 0.06396 -0.08025 AFIX 23 H33A 2 -0.006949 0.529425 0.026601 11.00000 -1.20000 H33B 2 -0.047157 0.565708 -0.027366 11.00000 -1.20000 AFIX 0 F3 4 -0.210068 0.686381 -0.060271 10.50000 0.22291 0.15940 = 0.21278 -0.00044 0.01305 0.03693 C36 1 -0.117670 0.548462 0.290108 11.00000 0.08417 0.43322 = 0.49578 0.08342 -0.03116 0.05133 AFIX 23 H36A 2 -0.130240 0.580103 0.256981 11.00000 -1.20000 H36B 2 -0.147999 0.533552 0.323928 11.00000 -1.20000 AFIX 0 C34 1 -0.075115 0.539363 0.082215 11.00000 0.17017 0.33442 = 0.40618 0.13218 -0.06039 -0.07824 AFIX 23 H34A 2 -0.101490 0.568204 0.091870 11.00000 -1.20000 H34B 2 -0.093002 0.510452 0.048950 11.00000 -1.20000 AFIX 0 PART 1 F8A 4 0.337032 0.578128 0.326676 10.50000 0.83065 0.67893 = 0.34155 0.19156 0.10320 -0.04755 PART 0 O12 6 0.182799 0.562210 0.324661 11.00000 0.18843 0.65878 = 0.54560 0.27500 -0.07091 -0.10576 AFIX 66 C42 1 -0.042002 0.606611 0.461664 11.00000 0.23902 0.15251 = 0.26512 0.08099 0.14568 0.00966 C37 1 -0.084518 0.597115 0.404925 11.00000 0.17662 0.26599 = 0.41944 0.06847 0.12628 0.03130 C38 1 -0.129020 0.630233 0.406766 11.00000 0.20905 0.19047 = 0.45947 0.08325 0.11977 0.02142 AFIX 43 H38 2 -0.158078 0.623743 0.367987 11.00000 -1.20000 AFIX 65 C39 1 -0.131006 0.672848 0.465345 11.00000 0.47269 0.28434 = 0.47737 0.02081 0.14832 0.06705 AFIX 43 H39 2 -0.161421 0.695483 0.466603 11.00000 -1.20000 AFIX 65 C40 1 -0.088490 0.682344 0.522084 11.00000 0.39835 0.20203 = 0.30045 0.06859 0.26163 0.02872 AFIX 43 H40 2 -0.089847 0.711470 0.562121 11.00000 -1.20000 AFIX 65 C41 1 -0.043988 0.649227 0.520244 11.00000 0.41364 0.16112 = 0.32023 0.05875 0.23677 0.01984 AFIX 43 H41 2 -0.014930 0.655717 0.559023 11.00000 -1.20000 AFIX 0 F4 4 -0.175547 0.773568 -0.069596 10.50000 0.18829 0.26050 = 0.24271 -0.05137 -0.00427 -0.09565 F5 4 0.394527 0.544284 0.225510 11.00000 0.59519 0.65349 = 0.60567 -0.02470 -0.11320 0.12042 C46 1 0.200729 0.564208 0.406490 11.00000 0.17096 0.45578 = 0.55037 0.13469 -0.06516 -0.00619 AFIX 23 H46A 2 0.196951 0.600069 0.433188 11.00000 -1.20000 H46B 2 0.238054 0.551641 0.411856 11.00000 -1.20000 AFIX 0 C31 1 0.054858 0.661308 0.028383 11.00000 0.22514 0.34884 = 0.18569 0.01188 0.00210 -0.15382 AFIX 23 H31A 2 0.022134 0.681757 0.042454 11.00000 -1.20000 H31B 2 0.075051 0.683465 -0.014134 11.00000 -1.20000 AFIX 0 PART 2 F6B 4 0.313829 0.569799 0.176322 10.50000 0.49116 0.35213 = 0.38104 -0.11437 -0.05936 -0.01147 PART 0 C48 1 0.214261 0.639534 0.279791 11.00000 0.20242 0.35753 = 1.16232 0.18488 -0.31812 -0.06655 AFIX 23 H48A 2 0.244568 0.660014 0.255091 11.00000 -1.20000 H48B 2 0.209820 0.648512 0.342914 11.00000 -1.20000 AFIX 0 C21 1 0.186841 0.779054 0.502777 11.00000 0.53094 0.28649 = 0.34032 -0.16315 -0.06293 0.07147 AFIX 137 H21A 2 0.206245 0.790672 0.555481 11.00000 -1.50000 H21B 2 0.204560 0.793170 0.450117 11.00000 -1.50000 H21C 2 0.186456 0.739967 0.500266 11.00000 -1.50000 AFIX 0 PART 1 F6A 4 0.306655 0.533227 0.209712 10.50000 0.61650 0.54180 = 0.73577 0.11493 -0.15619 -0.04046 PART 0 C47 1 0.220423 0.584806 0.266896 11.00000 0.20434 0.41413 = 0.67220 0.24483 0.06098 0.06452 AFIX 23 H47A 2 0.257073 0.573200 0.282003 11.00000 -1.20000 H47B 2 0.212734 0.574860 0.205032 11.00000 -1.20000 AFIX 0 PART 2 F7B 4 0.347937 0.605157 0.302212 10.50000 0.25586 0.42114 = 0.25734 0.16319 -0.11023 -0.14430 PART 0 C23 1 -0.147450 0.700595 0.108900 11.00000 0.26479 0.20733 = 0.68389 0.05865 -0.04493 0.11475 PART 2 AFIX 23 H23C 2 -0.172162 0.725642 0.138602 10.50000 -1.20000 H23D 2 -0.132720 0.718414 0.055979 10.50000 -1.20000 AFIX 23 PART 0 PART 1 H23A 2 -0.146536 0.678166 0.055196 10.50000 -1.20000 H23B 2 -0.182474 0.695735 0.138035 10.50000 -1.20000 AFIX 0 PART 0 C44 1 0.080532 0.544171 0.510881 11.00000 0.18362 0.38272 = 0.30955 0.00257 -0.06609 -0.07756 AFIX 23 H44A 2 0.063962 0.509966 0.493012 11.00000 -1.20000 H44B 2 0.103513 0.536930 0.562602 11.00000 -1.20000 AFIX 0 C35 1 -0.093829 0.504726 0.224434 11.00000 0.17693 0.27549 = 0.37348 0.10948 -0.08277 -0.07100 AFIX 23 H35A 2 -0.076734 0.476702 0.260764 11.00000 -1.20000 H35B 2 -0.124257 0.487791 0.193589 11.00000 -1.20000 AFIX 0 C45 1 0.162673 0.526388 0.440654 11.00000 0.20180 0.23656 = 0.33096 -0.01407 -0.06680 0.04525 AFIX 23 H45A 2 0.170852 0.515171 0.501748 11.00000 -1.20000 H45B 2 0.158429 0.494714 0.402270 11.00000 -1.20000 AFIX 0 PART 2 C24B 1 -0.174882 0.653506 0.084426 10.50000 0.30707 0.33766 = 0.59751 -0.03490 -0.00918 0.04510 AFIX 137 H24A 2 -0.170410 0.626474 0.130529 10.50000 -1.50000 H24B 2 -0.160314 0.639985 0.028791 10.50000 -1.50000 H24C 2 -0.212922 0.661442 0.077007 10.50000 -1.50000 AFIX 0 PART 0 C20 1 0.134694 0.798009 0.506276 11.00000 0.59991 0.30042 = 0.46942 -0.26425 -0.11468 0.18736 AFIX 23 H20A 2 0.131621 0.834620 0.482242 11.00000 -1.20000 H20B 2 0.120022 0.796982 0.566842 11.00000 -1.20000 AFIX 0 C22 1 -0.084735 0.720160 0.219164 11.00000 0.35639 0.14018 = 0.52753 -0.00346 -0.01298 0.13412 PART -1 B1 3 -0.217184 0.740269 -0.042947 10.50000 0.13005 0.15681 = 0.19100 -0.00649 -0.00835 0.00612 PART 0 B2 3 0.346598 0.563455 0.244093 11.00000 0.56750 0.53305 = 0.39747 0.03983 -0.06886 0.02003 PART 2 F8B 4 0.324811 0.521305 0.297792 10.50000 0.82269 0.39802 = 0.36760 -0.11082 -0.16745 -0.20080 PART 0 PART 1 F7A 4 0.344546 0.612641 0.192012 10.50000 0.24260 0.65022 = 0.26068 0.09141 0.08252 0.00361 C24A 1 -0.139635 0.754871 0.086758 10.50000 0.33478 0.25183 = 0.63860 0.10171 -0.05831 0.07211 AFIX 137 H24D 2 -0.122281 0.773302 0.136002 10.50000 -1.50000 H24E 2 -0.174228 0.771606 0.074674 10.50000 -1.50000 H24F 2 -0.116981 0.757315 0.034253 10.50000 -1.50000 AFIX 0 HKLF 4 REM cu_pb029_3_a.res in P4(2)/n REM wR2 = 0.5216, GooF = S = 1.677, Restrained GooF = 1.654 for all data REM R1 = 0.1892 for 2121 Fo > 4sig(Fo) and 0.2752 for all 4886 data REM 656 parameters refined using 611 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.573, deepest hole -0.399, 1-sigma level 0.096 Q1 1 0.2500 0.2500 0.2500 10.25000 0.05 0.57 Q2 1 -0.1721 0.6504 0.0043 11.00000 0.05 0.48 Q3 1 0.2376 0.4761 0.5195 11.00000 0.05 0.47 Q4 1 -0.0015 0.5863 -0.0529 11.00000 0.05 0.36 Q5 1 0.1650 0.6424 0.2008 11.00000 0.05 0.34 Q6 1 0.1139 0.5983 0.5031 11.00000 0.05 0.34 Q7 1 0.3632 0.5213 0.2355 11.00000 0.05 0.34 Q8 1 0.1600 0.6404 0.3107 11.00000 0.05 0.33 Q9 1 0.0175 0.5606 0.0200 11.00000 0.05 0.32 Q10 1 0.0356 0.7809 0.1284 11.00000 0.05 0.31 Q11 1 0.0368 0.6985 0.0446 11.00000 0.05 0.31 Q12 1 0.0323 0.5758 0.5019 11.00000 0.05 0.31 Q13 1 0.0248 0.5679 0.4784 11.00000 0.05 0.30 Q14 1 0.3028 0.5011 0.1518 11.00000 0.05 0.29 Q15 1 0.3996 0.6565 0.2952 11.00000 0.05 0.28 Q16 1 -0.0219 0.7023 0.2690 11.00000 0.05 0.28 Q17 1 -0.0410 0.5395 0.0119 11.00000 0.05 0.27 Q18 1 0.1011 0.5021 0.1811 11.00000 0.05 0.26 Q19 1 0.1762 0.6955 0.2557 11.00000 0.05 0.25 Q20 1 0.0166 0.7615 0.4342 11.00000 0.05 0.25 ; _shelx_res_checksum 79699 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.563 _oxdiff_exptl_absorpt_empirical_full_min 0.657 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2668(3) 0.3324(2) 0.2443(5) 0.094(2) Uani 1 1 d . U . . . H1 H 0.260330 0.299353 0.227679 0.113 Uiso 1 1 calc R U . . . F1 F -0.250000 0.750000 -0.1161(8) 0.154(3) Uani 1 2 d DS TU P . . C1 C 0.3175(4) 0.3533(3) 0.2653(7) 0.105(3) Uani 1 1 d . U . . . F2 F -0.250000 0.750000 0.0315(8) 0.186(4) Uani 1 2 d DS TU P . . C4 C 0.2292(3) 0.3718(3) 0.2539(7) 0.102(3) Uani 1 1 d . U . . . C2 C 0.3074(4) 0.4066(3) 0.2924(9) 0.126(4) Uani 1 1 d . U . . . H2 H 0.333270 0.430878 0.314377 0.152 Uiso 1 1 calc R U . . . C5 C 0.1736(3) 0.3651(3) 0.2403(6) 0.091(3) Uani 1 1 d . U . . . C6 C 0.1419(3) 0.4146(4) 0.2330(7) 0.100(3) Uani 1 1 d . U . . . C3 C 0.2549(4) 0.4171(4) 0.2820(8) 0.112(4) Uani 1 1 d . U . . . H3 H 0.238353 0.450586 0.292525 0.135 Uiso 1 1 calc R U . . . O10 O 0.0031(6) 0.5750(4) 0.4549(10) 0.215(5) Uani 1 1 d . U . . . C30 C 0.1052(5) 0.7041(5) 0.1404(8) 0.168(5) Uani 1 1 d . U . . . C25 C 0.1508(5) 0.6972(4) 0.1914(8) 0.194(6) Uani 1 1 d G U . . . C26 C 0.1769(5) 0.7413(6) 0.2262(8) 0.256(10) Uani 1 1 d G U . . . H26 H 0.208072 0.736631 0.261065 0.308 Uiso 1 1 calc R . . . . C27 C 0.1575(6) 0.7924(5) 0.2101(11) 0.311(14) Uani 1 1 d G U . . . H27 H 0.175354 0.822563 0.233949 0.373 Uiso 1 1 calc DR . . . . C28 C 0.1119(7) 0.7993(4) 0.1592(11) 0.320(16) Uani 1 1 d G U . . . H28 H 0.098602 0.834177 0.148169 0.384 Uiso 1 1 calc R . . . . C29 C 0.0857(5) 0.7551(6) 0.1243(9) 0.258(10) Uani 1 1 d G U . . . H29 H 0.054567 0.759859 0.089503 0.309 Uiso 1 1 calc R . . . . O9 O -0.0720(4) 0.5635(5) 0.3517(11) 0.229(5) Uani 1 1 d . U . . . C9 C 0.0815(5) 0.5071(4) 0.2217(10) 0.130(4) Uani 1 1 d . U . . . C10 C 0.0693(5) 0.4696(5) 0.2833(12) 0.162(5) Uani 1 1 d . U . . . H10 H 0.040774 0.475353 0.323388 0.194 Uiso 1 1 calc R U . . . C11 C 0.0990(4) 0.4229(4) 0.2870(9) 0.134(4) Uani 1 1 d . U . . . H11 H 0.089262 0.396028 0.328171 0.161 Uiso 1 1 calc R U . . . C7 C 0.1566(4) 0.4539(4) 0.1718(8) 0.118(4) Uani 1 1 d . U . . . H7 H 0.186254 0.449123 0.133650 0.142 Uiso 1 1 calc R U . . . C8 C 0.1255(5) 0.5009(4) 0.1690(9) 0.139(4) Uani 1 1 d . U . . . H8 H 0.135378 0.528828 0.129898 0.167 Uiso 1 1 calc R U . . . O11 O 0.1155(5) 0.5642(5) 0.4355(10) 0.232(5) Uani 1 1 d . U . . . C18 C -0.0053(7) 0.6552(5) 0.2525(12) 0.174(6) Uani 1 1 d . U . . . H18 H -0.018781 0.629851 0.211583 0.209 Uiso 1 1 calc R U . . . N2 N 0.0658(7) 0.5950(4) 0.2846(9) 0.210(6) Uani 1 1 d . U . . . H2A H 0.100710 0.601816 0.272521 0.252 Uiso 1 1 calc R U . . . H2B H 0.065098 0.577629 0.337231 0.252 Uiso 1 1 calc R U . . . C16 C -0.0092(10) 0.7416(7) 0.3344(15) 0.219(7) Uani 1 1 d . U . . . H16 H -0.027033 0.773368 0.351645 0.263 Uiso 1 1 calc R U . . . C13 C 0.0401(8) 0.6470(6) 0.2991(15) 0.178(6) Uani 1 1 d . U . . . C19 C 0.0653(15) 0.7690(12) 0.4258(19) 0.259(9) Uani 1 1 d . U . . . O4 O -0.1029(6) 0.6850(5) 0.1706(14) 0.289(8) Uani 1 1 d D U . . . O6 O 0.0841(7) 0.6622(7) 0.1029(12) 0.267(7) Uani 1 1 d . U . . . C17 C -0.0334(9) 0.7086(7) 0.2710(16) 0.218(6) Uani 1 1 d . U . . . O5 O 0.1645(6) 0.6484(8) 0.229(2) 0.458(19) Uani 1 1 d D U . . . O2 O 0.1095(12) 0.7583(8) 0.4487(17) 0.321(10) Uani 1 1 d . U . . . C14 C 0.0613(8) 0.6813(6) 0.3539(11) 0.194(6) Uani 1 1 d . U . . . H14 H 0.093800 0.671881 0.382176 0.233 Uiso 1 1 calc R U . . . O8 O -0.0585(5) 0.5198(7) 0.1630(16) 0.283(8) Uani 1 1 d . U . . . C32 C 0.0379(9) 0.6189(7) -0.0185(16) 0.256(9) Uani 1 1 d D U . . . H32A H 0.066606 0.592487 -0.028235 0.307 Uiso 1 1 calc R . . . . H32B H 0.022160 0.629587 -0.075719 0.307 Uiso 1 1 calc R . . . . C12 C 0.0492(6) 0.5600(5) 0.2241(12) 0.191(7) Uani 1 1 d . U . . . H12A H 0.051298 0.577100 0.165321 0.229 Uiso 1 1 calc R . . . . H12B H 0.011266 0.551502 0.235556 0.229 Uiso 1 1 calc R . . . . C15 C 0.0396(11) 0.7298(6) 0.3728(15) 0.218(6) Uani 1 1 d . U . . . O1 O 0.0405(9) 0.8079(5) 0.4536(10) 0.311(9) Uani 1 1 d . U . . . C43 C 0.0408(11) 0.5789(12) 0.5357(19) 0.285(12) Uani 1 1 d . U . . . H43A H 0.054648 0.615634 0.543640 0.342 Uiso 1 1 calc R . . . . H43B H 0.022951 0.567149 0.590533 0.342 Uiso 1 1 calc R . . . . O3 O -0.1068(8) 0.7631(6) 0.2291(17) 0.398(13) Uani 1 1 d . U . . . O7 O -0.0074(10) 0.5972(10) 0.0506(17) 0.411(15) Uani 1 1 d . U . . . C33 C -0.0327(10) 0.5592(9) 0.0324(16) 0.267(10) Uani 1 1 d . U . . . H33A H -0.006949 0.529425 0.026601 0.320 Uiso 1 1 calc R . . . . H33B H -0.047157 0.565708 -0.027366 0.320 Uiso 1 1 calc R . . . . F3 F -0.2101(7) 0.6864(6) -0.0603(12) 0.198(7) Uani 0.5 1 d D U . . . C36 C -0.1177(7) 0.5485(14) 0.290(2) 0.338(13) Uani 1 1 d . U . . . H36A H -0.130240 0.580103 0.256981 0.405 Uiso 1 1 calc R . . . . H36B H -0.147999 0.533552 0.323928 0.405 Uiso 1 1 calc R . . . . C34 C -0.0751(9) 0.5394(11) 0.082(2) 0.304(14) Uani 1 1 d . U . . . H34A H -0.101490 0.568204 0.091870 0.364 Uiso 1 1 calc R . . . . H34B H -0.093002 0.510452 0.048950 0.364 Uiso 1 1 calc R . . . . F8A F 0.337(2) 0.578(2) 0.3267(16) 0.62(4) Uani 0.5 1 d D U . A 1 O12 O 0.1828(8) 0.5622(17) 0.325(2) 0.46(2) Uani 1 1 d D U . . . C42 C -0.0420(6) 0.6066(6) 0.4617(12) 0.219(6) Uani 1 1 d . U . . . C37 C -0.0845(8) 0.5971(5) 0.4049(11) 0.287(11) Uani 1 1 d G U . . . C38 C -0.1290(6) 0.6302(7) 0.4068(12) 0.286(11) Uani 1 1 d G U . . . H38 H -0.158078 0.623743 0.367987 0.344 Uiso 1 1 calc R . . . . C39 C -0.1310(6) 0.6728(6) 0.4653(14) 0.41(2) Uani 1 1 d G U . . . H39 H -0.161421 0.695483 0.466603 0.494 Uiso 1 1 calc R . . . . C40 C -0.0885(9) 0.6823(5) 0.5221(10) 0.300(13) Uani 1 1 d G U . . . H40 H -0.089847 0.711470 0.562121 0.360 Uiso 1 1 calc R . . . . C41 C -0.0440(7) 0.6492(7) 0.5202(9) 0.298(10) Uani 1 1 d G U . . . H41 H -0.014930 0.655717 0.559023 0.358 Uiso 1 1 calc R . . . . F4 F -0.1755(7) 0.7736(8) -0.0696(13) 0.231(8) Uani 0.5 1 d D U . . . F5 F 0.3945(11) 0.5443(14) 0.226(2) 0.62(2) Uani 1 1 d D U . . . C46 C 0.2007(12) 0.564(2) 0.406(3) 0.39(2) Uani 1 1 d . U . . . H46A H 0.196951 0.600069 0.433188 0.471 Uiso 1 1 calc R . . . . H46B H 0.238054 0.551641 0.411856 0.471 Uiso 1 1 calc R . . . . C31 C 0.0549(9) 0.6613(10) 0.0284(14) 0.253(11) Uani 1 1 d D U . . . H31A H 0.022134 0.681757 0.042454 0.304 Uiso 1 1 calc R . . . . H31B H 0.075051 0.683465 -0.014134 0.304 Uiso 1 1 calc R . . . . F6B F 0.3138(15) 0.5698(14) 0.1763(18) 0.41(2) Uani 0.5 1 d D U . A 2 C48 C 0.2143(11) 0.6395(15) 0.280(3) 0.57(4) Uani 1 1 d D U . . . H48A H 0.244568 0.660014 0.255091 0.689 Uiso 1 1 calc R . . . . H48B H 0.209820 0.648512 0.342914 0.689 Uiso 1 1 calc R . . . . C21 C 0.1868(15) 0.7791(13) 0.503(2) 0.386(17) Uani 1 1 d D U . . . H21A H 0.206245 0.790672 0.555481 0.579 Uiso 1 1 calc GR U . . . H21B H 0.204560 0.793170 0.450117 0.579 Uiso 1 1 calc GR U . . . H21C H 0.186456 0.739967 0.500266 0.579 Uiso 1 1 calc GR U . . . F6A F 0.3067(16) 0.5332(17) 0.210(4) 0.63(4) Uani 0.5 1 d D U . A 1 C47 C 0.2204(11) 0.5848(15) 0.267(3) 0.43(2) Uani 1 1 d D U . . . H47A H 0.257073 0.573200 0.282003 0.516 Uiso 1 1 calc DR . . . . H47B H 0.212734 0.574860 0.205032 0.516 Uiso 1 1 calc DR . . . . F7B F 0.3479(9) 0.6052(8) 0.3022(16) 0.311(12) Uani 0.5 1 d D U . A 2 C23 C -0.1474(11) 0.7006(9) 0.109(3) 0.385(17) Uani 1 1 d D U . . . H23C H -0.172162 0.725642 0.138602 0.462 Uiso 0.5 1 calc R . . B 2 H23D H -0.132720 0.718414 0.055979 0.462 Uiso 0.5 1 calc R . . B 2 H23A H -0.146536 0.678166 0.055196 0.462 Uiso 0.5 1 calc R . . C 1 H23B H -0.182474 0.695735 0.138035 0.462 Uiso 0.5 1 calc R . . C 1 C44 C 0.0805(10) 0.5442(13) 0.511(2) 0.292(13) Uani 1 1 d . U . . . H44A H 0.063962 0.509966 0.493012 0.350 Uiso 1 1 calc R . . . . H44B H 0.103513 0.536930 0.562602 0.350 Uiso 1 1 calc R . . . . C35 C -0.0938(11) 0.5047(11) 0.2244(19) 0.275(9) Uani 1 1 d . U . . . H35A H -0.076734 0.476702 0.260764 0.330 Uiso 1 1 calc R . . . . H35B H -0.124257 0.487791 0.193589 0.330 Uiso 1 1 calc R . . . . C45 C 0.1627(9) 0.5264(9) 0.4407(19) 0.256(8) Uani 1 1 d . U . . . H45A H 0.170852 0.515171 0.501748 0.308 Uiso 1 1 calc R . . . . H45B H 0.158429 0.494714 0.402270 0.308 Uiso 1 1 calc R . . . . C24B C -0.175(2) 0.6535(17) 0.084(3) 0.41(3) Uani 0.5 1 d D U . D 2 H24A H -0.170410 0.626474 0.130529 0.621 Uiso 0.5 1 calc DGR . . D 2 H24B H -0.160314 0.639985 0.028791 0.621 Uiso 0.5 1 calc DGR . . D 2 H24C H -0.212922 0.661442 0.077007 0.621 Uiso 0.5 1 calc DGR . . D 2 C20 C 0.1347(17) 0.7980(13) 0.506(3) 0.46(3) Uani 1 1 d D U . . . H20A H 0.131621 0.834620 0.482242 0.548 Uiso 1 1 calc R U . . . H20B H 0.120022 0.796982 0.566842 0.548 Uiso 1 1 calc R U . . . C22 C -0.0847(16) 0.7202(10) 0.219(3) 0.341(16) Uani 1 1 d . U . . . B1 B -0.2172(9) 0.7403(9) -0.0429(13) 0.159(6) Uani 0.5 1 d D U . E -1 B2 B 0.3466(11) 0.5635(10) 0.2441(14) 0.50(2) Uani 1 1 d D U . . . F8B F 0.3248(13) 0.5213(9) 0.298(2) 0.53(3) Uani 0.5 1 d D U . A 2 F7A F 0.3445(12) 0.6126(14) 0.192(2) 0.385(19) Uani 0.5 1 d D U . A 1 C24A C -0.140(2) 0.7549(11) 0.087(2) 0.41(3) Uani 0.5 1 d D U . D 1 H24D H -0.122281 0.773302 0.136002 0.613 Uiso 0.5 1 calc GR . . D 1 H24E H -0.174228 0.771606 0.074674 0.613 Uiso 0.5 1 calc DGR . . D 1 H24F H -0.116981 0.757315 0.034253 0.613 Uiso 0.5 1 calc DGR . . D 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.080(4) 0.061(4) 0.141(7) 0.004(4) -0.004(4) -0.002(3) F1 0.149(8) 0.142(7) 0.170(9) 0.000 0.000 -0.012(6) C1 0.090(5) 0.062(5) 0.162(10) -0.010(5) -0.010(6) 0.006(4) F2 0.212(11) 0.174(9) 0.173(10) 0.000 0.000 0.032(8) C4 0.067(4) 0.070(5) 0.170(10) 0.003(6) -0.006(6) 0.004(4) C2 0.088(5) 0.061(5) 0.230(13) -0.004(6) -0.007(7) -0.002(4) C5 0.080(5) 0.079(5) 0.112(8) -0.001(5) -0.002(5) 0.004(4) C6 0.070(5) 0.076(5) 0.152(10) -0.002(5) -0.002(5) 0.002(4) C3 0.079(5) 0.079(5) 0.179(11) -0.013(6) -0.018(6) 0.008(4) O10 0.216(11) 0.153(8) 0.275(16) 0.062(9) 0.078(10) 0.000(7) C30 0.170(12) 0.162(11) 0.171(15) 0.028(10) 0.021(9) -0.051(10) C25 0.146(12) 0.246(15) 0.190(18) 0.051(12) 0.044(9) -0.047(10) C26 0.24(2) 0.32(2) 0.214(19) -0.03(2) -0.035(15) -0.032(17) C27 0.26(3) 0.272(18) 0.41(4) 0.00(3) 0.05(2) -0.074(19) C28 0.33(3) 0.180(14) 0.45(5) 0.071(19) 0.01(2) -0.002(17) C29 0.31(2) 0.227(14) 0.24(2) 0.087(18) -0.018(16) 0.017(15) O9 0.140(8) 0.182(10) 0.364(16) 0.090(9) 0.036(9) -0.005(7) C9 0.100(7) 0.089(6) 0.202(13) -0.017(6) -0.034(7) 0.020(6) C10 0.098(8) 0.123(9) 0.265(16) 0.015(9) 0.026(9) 0.028(7) C11 0.088(7) 0.095(6) 0.220(12) 0.010(7) 0.031(7) 0.004(5) C7 0.101(7) 0.104(7) 0.150(10) 0.011(6) -0.008(6) 0.021(5) C8 0.131(9) 0.080(6) 0.207(14) 0.010(7) -0.012(8) 0.008(6) O11 0.169(10) 0.223(12) 0.303(15) -0.038(11) -0.024(9) 0.046(8) C18 0.199(13) 0.095(8) 0.228(17) 0.005(8) 0.092(10) 0.014(8) N2 0.348(17) 0.093(7) 0.190(12) -0.028(7) -0.019(11) 0.063(8) C16 0.308(18) 0.091(10) 0.26(2) 0.023(10) 0.147(11) 0.059(11) C13 0.211(14) 0.087(8) 0.237(19) 0.010(8) 0.076(11) 0.021(9) C19 0.49(3) 0.136(14) 0.150(19) -0.032(12) 0.064(18) 0.073(16) O4 0.242(13) 0.129(9) 0.49(3) 0.032(11) 0.041(12) 0.073(9) O6 0.275(16) 0.275(13) 0.252(16) -0.031(12) -0.035(11) -0.079(11) C17 0.257(15) 0.110(10) 0.29(2) 0.038(10) 0.112(10) 0.059(10) O5 0.165(11) 0.298(17) 0.91(6) 0.18(2) -0.176(19) -0.005(11) O2 0.51(2) 0.195(15) 0.26(2) -0.086(13) -0.013(19) 0.072(15) C14 0.286(17) 0.098(9) 0.198(15) -0.013(8) 0.057(11) 0.052(10) O8 0.125(10) 0.291(16) 0.43(2) 0.126(16) -0.048(11) -0.019(9) C32 0.29(2) 0.177(16) 0.30(2) 0.053(14) -0.066(16) -0.060(15) C12 0.184(12) 0.117(8) 0.270(18) -0.034(9) -0.100(11) 0.057(8) C15 0.332(19) 0.084(8) 0.238(18) 0.005(9) 0.114(13) 0.044(10) O1 0.55(3) 0.127(8) 0.253(15) -0.036(8) 0.064(15) 0.079(12) C43 0.25(2) 0.36(3) 0.25(2) 0.12(2) 0.074(12) -0.074(18) O3 0.40(2) 0.146(10) 0.65(4) -0.005(14) -0.01(2) 0.159(13) O7 0.42(3) 0.40(3) 0.41(3) -0.02(2) 0.006(19) -0.26(2) C33 0.26(2) 0.24(2) 0.30(2) -0.112(16) 0.064(18) -0.080(15) F3 0.223(15) 0.159(10) 0.213(17) 0.000(10) 0.013(12) 0.037(10) C36 0.084(10) 0.43(4) 0.50(3) 0.08(2) -0.031(13) 0.051(15) C34 0.170(18) 0.33(3) 0.41(3) 0.13(3) -0.060(16) -0.078(18) F8A 0.83(12) 0.68(10) 0.34(3) 0.19(3) 0.10(5) -0.05(7) O12 0.188(17) 0.66(4) 0.55(4) 0.27(4) -0.07(2) -0.11(2) C42 0.239(14) 0.153(13) 0.265(19) 0.081(10) 0.146(11) 0.010(11) C37 0.177(15) 0.27(3) 0.42(3) 0.068(15) 0.126(13) 0.031(14) C38 0.209(15) 0.190(19) 0.46(3) 0.083(17) 0.120(17) 0.021(13) C39 0.47(4) 0.28(3) 0.48(5) 0.02(2) 0.15(3) 0.07(3) C40 0.40(3) 0.202(17) 0.30(2) 0.069(14) 0.26(2) 0.029(15) C41 0.41(3) 0.161(16) 0.32(2) 0.059(12) 0.237(18) 0.020(14) F4 0.188(13) 0.261(17) 0.243(19) -0.051(15) -0.004(11) -0.096(13) F5 0.60(4) 0.65(5) 0.61(5) -0.02(3) -0.11(3) 0.12(3) C46 0.171(18) 0.46(5) 0.55(4) 0.13(5) -0.07(2) -0.01(2) C31 0.225(19) 0.35(3) 0.186(18) 0.012(16) 0.002(12) -0.154(19) F6B 0.49(4) 0.35(4) 0.38(3) -0.11(3) -0.06(3) -0.01(3) C48 0.20(3) 0.36(4) 1.16(11) 0.18(4) -0.32(4) -0.07(2) C21 0.53(3) 0.29(3) 0.34(3) -0.16(3) -0.06(3) 0.07(3) F6A 0.62(5) 0.54(6) 0.74(8) 0.11(5) -0.16(6) -0.04(5) C47 0.20(3) 0.41(4) 0.67(5) 0.24(4) 0.06(3) 0.06(3) F7B 0.26(2) 0.42(3) 0.26(2) 0.163(18) -0.110(17) -0.144(19) C23 0.26(3) 0.21(2) 0.68(5) 0.06(3) -0.04(2) 0.11(2) C44 0.184(17) 0.38(3) 0.31(3) 0.00(2) -0.066(13) -0.078(16) C35 0.18(2) 0.28(2) 0.37(2) 0.109(14) -0.083(14) -0.071(16) C45 0.202(17) 0.24(2) 0.33(2) -0.014(17) -0.067(15) 0.045(13) C24B 0.31(5) 0.34(5) 0.60(7) -0.03(6) -0.01(4) 0.05(4) C20 0.60(4) 0.30(3) 0.47(5) -0.26(4) -0.11(4) 0.19(3) C22 0.36(3) 0.140(16) 0.53(4) -0.003(18) -0.01(2) 0.134(17) B1 0.130(18) 0.157(14) 0.191(18) -0.01(2) -0.008(10) 0.006(16) B2 0.57(5) 0.53(4) 0.40(4) 0.04(2) -0.07(3) 0.02(3) F8B 0.82(7) 0.40(4) 0.37(4) -0.11(3) -0.17(4) -0.20(5) F7A 0.24(3) 0.65(5) 0.26(3) 0.09(4) 0.08(2) 0.00(3) C24A 0.33(4) 0.25(3) 0.64(6) 0.10(4) -0.06(5) 0.07(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 109.0(7) . . ? N1 C1 C2 104.7(8) . . ? C5 C1 N1 125.8(7) 7_566 . ? C5 C1 C2 129.5(9) 7_566 . ? N1 C4 C5 125.0(8) . . ? C3 C4 N1 107.8(8) . . ? C3 C4 C5 127.2(8) . . ? C3 C2 C1 108.9(9) . . ? C1 C5 C4 126.6(8) 8_656 . ? C1 C5 C6 117.3(8) 8_656 . ? C4 C5 C6 116.1(7) . . ? C11 C6 C5 120.3(9) . . ? C11 C6 C7 119.7(9) . . ? C7 C6 C5 119.9(9) . . ? C2 C3 C4 109.4(8) . . ? C42 O10 C43 113.8(19) . . ? C25 C30 C29 120.0 . . ? O6 C30 C25 118.4(13) . . ? O6 C30 C29 121.4(13) . . ? C30 C25 C26 120.0 . . ? C30 C25 O5 122.8(12) . . ? C26 C25 O5 115.1(13) . . ? C27 C26 C25 120.0 . . ? C26 C27 C28 120.0 . . ? C29 C28 C27 120.0 . . ? C28 C29 C30 120.0 . . ? C37 O9 C36 112.8(18) . . ? C10 C9 C8 120.1(11) . . ? C10 C9 C12 117.2(14) . . ? C8 C9 C12 122.0(14) . . ? C9 C10 C11 119.4(12) . . ? C6 C11 C10 121.6(11) . . ? C6 C7 C8 117.5(11) . . ? C9 C8 C7 121.4(12) . . ? C45 O11 C44 101.8(19) . . ? C13 C18 C17 114.9(19) . . ? C12 N2 C13 123.3(15) . . ? C15 C16 C17 122.8(18) . . ? C18 C13 N2 115.1(18) . . ? C14 C13 C18 124.9(18) . . ? C14 C13 N2 120(2) . . ? O2 C19 C15 115(3) . . ? O2 C19 O1 123(3) . . ? O1 C19 C15 121(3) . . ? C22 O4 C23 117(2) . . ? C30 O6 C31 127(2) . . ? C16 C17 C18 116(2) . . ? C16 C17 C22 126.9(19) . . ? C22 C17 C18 117(2) . . ? C25 O5 C48 124(2) . . ? C19 O2 C20 115(3) . . ? C13 C14 C15 124(2) . . ? C35 O8 C34 121(2) . . ? C31 C32 O7 98.3(19) . . ? N2 C12 C9 114.5(11) . . ? C16 C15 C19 119(2) . . ? C14 C15 C16 117(2) . . ? C14 C15 C19 124(3) . . ? C44 C43 O10 101(3) . . ? C33 O7 C32 120(3) . . ? O7 C33 C34 125(3) . . ? O9 C36 C35 105.8(14) . . ? O8 C34 C33 112(2) . . ? C46 O12 C47 110(3) . . ? O10 C42 C37 118.8(17) . . ? O10 C42 C41 121.1(17) . . ? C37 C42 C41 120.0 . . ? O9 C37 C42 109.6(18) . . ? O9 C37 C38 129.6(18) . . ? C38 C37 C42 120.0 . . ? C37 C38 C39 120.0 . . ? C40 C39 C38 120.0 . . ? C39 C40 C41 120.0 . . ? C40 C41 C42 120.0 . . ? O12 C46 C45 95(3) . . ? C32 C31 O6 129(3) . . ? C47 C48 O5 100(2) . . ? C48 C47 O12 104(3) . . ? C24B C23 O4 107.9(19) . . ? C24A C23 O4 107(2) . . ? C43 C44 O11 114(3) . . ? O8 C35 C36 119(2) . . ? C46 C45 O11 95(2) . . ? C21 C20 O2 99(2) . . ? O4 C22 C17 119(2) . . ? O3 C22 O4 122(3) . . ? O3 C22 C17 119(3) . . ? F1 B1 F2 105.1(17) . . ? F3 B1 F1 95.4(15) . . ? F3 B1 F2 113.1(16) . . ? F3 B1 F4 116(2) . . ? F4 B1 F1 96.0(14) . . ? F4 B1 F2 124.1(18) . . ? F8A B2 F6A 112.6(18) . . ? F8A B2 F7A 105.7(17) . . ? F5 B2 F8A 117.7(19) . . ? F5 B2 F6B 116.1(18) . . ? F5 B2 F6A 112.6(18) . . ? F5 B2 F7B 113.1(17) . . ? F5 B2 F8B 101.4(15) . . ? F5 B2 F7A 102.8(15) . . ? F6B B2 F7B 115.1(17) . . ? F6B B2 F8B 107.0(17) . . ? F6A B2 F7A 103.6(17) . . ? F7B B2 F8B 101.8(15) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.411(11) . ? N1 C4 1.372(10) . ? F1 B1 1.403(19) . ? C1 C2 1.419(12) . ? C1 C5 1.373(12) 7_566 ? F2 B1 1.418(18) . ? C4 C5 1.418(12) . ? C4 C3 1.372(11) . ? C2 C3 1.349(12) . ? C5 C6 1.478(12) . ? C6 C11 1.368(13) . ? C6 C7 1.402(13) . ? O10 C43 1.55(3) . ? O10 C42 1.383(15) . ? C30 C25 1.3900 . ? C30 C29 1.3900 . ? C30 O6 1.305(15) . ? C25 C26 1.3900 . ? C25 O5 1.393(19) . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C28 C29 1.3900 . ? O9 C36 1.52(3) . ? O9 C37 1.208(17) . ? C9 C10 1.360(17) . ? C9 C8 1.371(16) . ? C9 C12 1.553(16) . ? C10 C11 1.387(14) . ? C7 C8 1.411(14) . ? O11 C44 1.53(3) . ? O11 C45 1.52(2) . ? C18 C13 1.35(2) . ? C18 C17 1.54(2) . ? N2 C13 1.470(19) . ? N2 C12 1.334(15) . ? C16 C17 1.41(3) . ? C16 C15 1.39(3) . ? C13 C14 1.31(2) . ? C19 O2 1.19(4) . ? C19 C15 1.42(4) . ? C19 O1 1.23(3) . ? O4 C23 1.51(3) . ? O4 C22 1.24(4) . ? O6 C31 1.35(2) . ? C17 C22 1.54(4) . ? O5 C48 1.480(18) . ? O2 C20 1.47(3) . ? C14 C15 1.36(2) . ? O8 C34 1.38(3) . ? O8 C35 1.34(3) . ? C32 O7 1.64(3) . ? C32 C31 1.347(16) . ? C43 C44 1.37(3) . ? O3 C22 1.22(2) . ? O7 C33 1.177(19) . ? C33 C34 1.39(3) . ? F3 B1 1.387(18) . ? C36 C35 1.60(4) . ? F8A B2 1.328(18) . ? O12 C46 1.32(5) . ? O12 C47 1.406(19) . ? C42 C37 1.3900 . ? C42 C41 1.3900 . ? C37 C38 1.3900 . ? C38 C39 1.3900 . ? C39 C40 1.3900 . ? C40 C41 1.3900 . ? F4 B1 1.395(18) . ? F5 B2 1.324(17) . ? C46 C45 1.44(4) . ? F6B B2 1.325(17) . ? C48 C47 1.39(2) . ? C21 C20 1.39(2) . ? F6A B2 1.359(18) . ? F7B B2 1.368(18) . ? C23 C24B 1.415(19) . ? C23 C24A 1.414(19) . ? B2 F8B 1.441(18) . ? B2 F7A 1.465(18) . ?