#------------------------------------------------------------------------------ #$Date: 2020-01-01 04:32:34 +0200 (Wed, 01 Jan 2020) $ #$Revision: 246352 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125705.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_7125705 loop_ _publ_author_name 'Fu, Wei' 'Wang, Lianhui' 'Yang, Zi' 'Shen, Jiang-Shan' 'Tang, Fei' 'Zhang, Jiayi' 'Cui, Xiuling' _publ_section_title ; Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization. ; _journal_name_full 'Chemical communications (Cambridge, England)' _journal_paper_doi 10.1039/c9cc07372h _journal_year 2019 _chemical_formula_moiety 'C22 H20 F2 N2 O4' _chemical_formula_sum 'C22 H20 F2 N2 O4' _chemical_formula_weight 414.40 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-11-02 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2019-11-04 deposited with the CCDC. 2019-12-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.347(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.6617(14) _cell_length_b 9.8335(5) _cell_length_c 12.6100(9) _cell_measurement_reflns_used 1967 _cell_measurement_temperature 293.1(2) _cell_measurement_theta_max 24.9560 _cell_measurement_theta_min 4.1910 _cell_volume 1992.4(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293.1(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1213 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.848 _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 1.00 83.00 1.00 7.50 -- 15.49 57.00 30.00 82 2 \w 35.00 60.00 1.00 7.50 -- 15.49 178.00-180.00 25 3 \w -49.00 42.00 1.00 7.50 -- 15.49 -77.00-120.00 91 4 \w -19.00 8.00 1.00 7.50 -- -16.12 -99.00 30.00 27 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0406586000 _diffrn_orient_matrix_UB_12 -0.0037742000 _diffrn_orient_matrix_UB_13 -0.0360731000 _diffrn_orient_matrix_UB_21 0.0068030000 _diffrn_orient_matrix_UB_22 -0.0692290000 _diffrn_orient_matrix_UB_23 -0.0108836000 _diffrn_orient_matrix_UB_31 -0.0158879000 _diffrn_orient_matrix_UB_32 -0.0199847000 _diffrn_orient_matrix_UB_33 0.0444779000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_unetI/netI 0.0614 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.848 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9755 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.848 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.262 _diffrn_reflns_theta_min 3.628 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_description plate _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.314 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.106 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 4601 _refine_ls_number_restraints 20 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0609 _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^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1262 _refine_ls_wR_factor_ref 0.1623 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2577 _reflns_number_total 4601 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07372h2.cif _cod_data_source_block syn-3l _cod_database_code 7125705 _shelx_shelxl_version_number 2018/1 _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. ; _reflns_odcompleteness_completeness 99.58 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Restrained distances C9-C8 \\sim C9B-C8 with sigma of 0.01 C9B-C10B \\sim C9-C10 with sigma of 0.01 3. Uiso/Uaniso restraints and constraints Uanis(C9) \\sim Ueq, Uanis(C9B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Others Sof(H8B)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C9B)=Sof(H9B)=1-FVAR(1) Sof(H8A)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C8(H8A), C8(H8B), C18(H18) 5.b Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C22(H22A,H22B) 5.c Aromatic/amide H refined with riding coordinates: C6(H6), C4(H4), C3(H3), C9(H9), C16(H16), C14(H14), C13(H13), C19(H19), C9B(H9B) 5.d X=CH2 refined with riding coordinates: C10(H10A,H10B), C20(H20A,H20B), C10B(H10C,H10D) ; _shelx_res_file ; TITL exp_7053_a.res in P2(1)/c syn-3l.res created by SHELXL-2018/1 at 15:09:00 on 02-Nov-2019 REM Old TITL exp_7053 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.204, Rweak 0.494, Alpha 0.026, Orientation as input REM Formula found by SHELXT: C19 N2 O8 CELL 0.71073 16.6617 9.8335 12.61 90 105.347 90 ZERR 4 0.0014 0.0005 0.0009 0 0.007 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 88 80 8 8 16 SADI 0.01 C9 C8 C9B C8 SADI 0.01 C9B C10B C9 C10 ISOR 0.01 0.02 C9 C9B ISOR 0.01 0.02 C10 L.S. 10 PLAN 4 TEMP 20.0(2) BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.067000 FVAR 0.66177 0.72450 F1 3 0.496301 0.902457 0.604154 11.00000 0.07727 0.06570 = 0.09004 0.00196 0.02819 -0.02531 F2 3 0.050909 0.335480 0.140344 11.00000 0.08855 0.07086 = 0.04799 -0.00194 0.00571 -0.00768 O2 5 0.326398 0.366836 0.732662 11.00000 0.05836 0.05215 = 0.05599 0.00877 0.02040 0.00249 O1 5 0.384740 0.309599 0.596712 11.00000 0.05850 0.04497 = 0.06881 -0.00380 0.02532 0.00539 O4 5 0.156456 0.442891 0.654680 11.00000 0.05852 0.04685 = 0.05027 0.00305 0.02259 0.00066 O3 5 0.122183 0.648844 0.579686 11.00000 0.05466 0.04027 = 0.06027 -0.00804 0.01389 0.00481 N1 4 0.294636 0.646295 0.719903 11.00000 0.05242 0.04133 = 0.05901 0.00110 0.02359 -0.00005 N2 4 0.206735 0.275634 0.510378 11.00000 0.05928 0.04326 = 0.04414 -0.00152 0.01608 0.01277 C1 1 0.365686 0.650977 0.685452 11.00000 0.04510 0.04810 = 0.03935 -0.00296 0.00980 -0.00307 C6 1 0.399147 0.775905 0.665078 11.00000 0.05062 0.04322 = 0.05482 -0.00386 0.01328 -0.00381 AFIX 43 H6 2 0.374142 0.856738 0.677561 11.00000 -1.20000 AFIX 0 C5 1 0.468138 0.778828 0.627080 11.00000 0.05492 0.05492 = 0.05484 -0.00227 0.01336 -0.01513 C4 1 0.510658 0.665106 0.609812 11.00000 0.04950 0.07552 = 0.06790 -0.00561 0.02379 -0.01084 AFIX 43 H4 2 0.559190 0.671082 0.586867 11.00000 -1.20000 AFIX 0 C3 1 0.477790 0.541808 0.628192 11.00000 0.04643 0.06074 = 0.06241 -0.00476 0.01620 0.00260 AFIX 43 H3 2 0.504587 0.462543 0.616290 11.00000 -1.20000 AFIX 0 C2 1 0.406067 0.531437 0.663864 11.00000 0.04152 0.04741 = 0.04136 0.00056 0.00928 0.00101 C7 1 0.368473 0.397312 0.671715 11.00000 0.04171 0.04585 = 0.04997 0.00567 0.00566 0.01086 C8 1 0.237328 0.759817 0.710292 11.00000 0.05289 0.04250 = 0.05871 -0.00863 0.02095 0.00112 PART 1 AFIX 13 H8A 2 0.240932 0.811631 0.645325 21.00000 -1.20000 AFIX 13 PART 0 PART 2 H8B 2 0.243223 0.822202 0.652215 -21.00000 -1.20000 AFIX 0 PART 0 C21 1 0.148447 0.709268 0.687487 11.00000 0.05788 0.04939 = 0.06937 -0.01515 0.02537 0.00524 AFIX 23 H21A 2 0.144484 0.642501 0.742499 11.00000 -1.20000 H21B 2 0.111981 0.784609 0.692237 11.00000 -1.20000 AFIX 0 PART 1 C9 1 0.251194 0.859387 0.803500 21.00000 0.05847 0.05648 = 0.08356 -0.03078 0.01505 0.00397 AFIX 43 H9 2 0.215009 0.932529 0.798602 21.00000 -1.20000 AFIX 0 C10 1 0.311963 0.845656 0.889816 21.00000 0.09132 0.09409 = 0.06019 -0.02230 0.01191 -0.01019 AFIX 93 H10A 2 0.348490 0.772857 0.895499 21.00000 -1.20000 H10B 2 0.319503 0.908497 0.946725 21.00000 -1.20000 AFIX 0 PART 0 C11 1 0.149222 0.345431 0.432473 11.00000 0.04198 0.03339 = 0.04790 0.00509 0.01332 -0.00129 C16 1 0.128118 0.304779 0.322082 11.00000 0.05757 0.03894 = 0.04690 0.00035 0.01384 -0.00175 AFIX 43 H16 2 0.152700 0.228468 0.300400 11.00000 -1.20000 AFIX 0 C15 1 0.070901 0.378983 0.246879 11.00000 0.05058 0.04958 = 0.04529 -0.00107 0.00959 -0.01315 C14 1 0.031379 0.491792 0.270647 11.00000 0.04187 0.05126 = 0.05867 0.00900 0.00504 -0.00255 AFIX 43 H14 2 -0.008244 0.537709 0.216690 11.00000 -1.20000 AFIX 0 C13 1 0.052999 0.534270 0.378277 11.00000 0.03669 0.04122 = 0.06577 0.00318 0.01475 0.00086 AFIX 43 H13 2 0.028728 0.612714 0.397007 11.00000 -1.20000 AFIX 0 C12 1 0.110025 0.463546 0.459948 11.00000 0.03586 0.03652 = 0.05038 0.00260 0.01450 -0.00343 C18 1 0.266219 0.180497 0.488292 11.00000 0.06448 0.03670 = 0.05191 0.00307 0.02121 0.01233 AFIX 13 H18 2 0.282077 0.211949 0.422915 11.00000 -1.20000 AFIX 0 C22 1 0.344260 0.178954 0.584573 11.00000 0.06037 0.03639 = 0.07274 0.00421 0.01600 0.01190 AFIX 23 H22A 2 0.329244 0.156257 0.651694 11.00000 -1.20000 H22B 2 0.382320 0.109861 0.572145 11.00000 -1.20000 AFIX 0 C19 1 0.233995 0.037495 0.467226 11.00000 0.08307 0.04035 = 0.05997 -0.00298 0.01430 0.00768 AFIX 43 H19 2 0.268322 -0.025357 0.445706 11.00000 -1.20000 AFIX 0 C20 1 0.162661 -0.006157 0.476345 11.00000 0.10167 0.05142 = 0.06213 0.00456 0.01240 -0.01268 AFIX 93 H20A 2 0.126321 0.053143 0.497648 11.00000 -1.20000 H20B 2 0.147854 -0.096755 0.461580 11.00000 -1.20000 AFIX 0 C17 1 0.131515 0.513364 0.573779 11.00000 0.03640 0.04061 = 0.05474 -0.00066 0.01970 0.00023 PART 2 C10B 1 0.284725 0.952142 0.848058 -21.00000 0.06450 0.06591 = 0.09269 -0.01345 0.02873 -0.00935 AFIX 93 H10C 2 0.275171 1.017599 0.792895 -21.00000 -1.20000 H10D 2 0.304855 0.977825 0.921280 -21.00000 -1.20000 AFIX 0 PART 0 H2 2 0.212578 0.300347 0.576082 11.00000 0.03935 H1 2 0.277555 0.568226 0.730288 11.00000 0.04890 PART 2 C9B 1 0.270030 0.825478 0.822959 -21.00000 0.05861 0.04099 = 0.09338 -0.00789 0.02916 0.01159 AFIX 43 H9B 2 0.281001 0.765753 0.882244 -21.00000 -1.20000 AFIX 0 HKLF 4 REM exp_7053_a.res in P2(1)/c REM R1 = 0.0609 for 2577 Fo > 4sig(Fo) and 0.1145 for all 4601 data REM 298 parameters refined using 20 restraints END WGHT 0.0670 0.0000 REM Highest difference peak 0.314, deepest hole -0.409, 1-sigma level 0.106 Q1 1 0.2968 0.7817 1.0414 11.00000 0.05 0.31 Q2 1 0.0217 0.2822 0.4506 11.00000 0.05 0.30 Q3 1 0.4772 0.6582 0.7915 11.00000 0.05 0.30 Q4 1 0.2984 0.9703 1.0659 11.00000 0.05 0.28 ; _shelx_res_checksum 65036 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 3.038 _oxdiff_exptl_absorpt_empirical_full_min 0.652 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 F1 F 0.49630(10) 0.90246(15) 0.60415(13) 0.0765(5) Uani 1 1 d . . . . . F2 F 0.05091(10) 0.33548(14) 0.14034(11) 0.0715(5) Uani 1 1 d . . . . . O2 O 0.32640(11) 0.36684(15) 0.73266(13) 0.0545(5) Uani 1 1 d . . . . . O1 O 0.38474(11) 0.30960(15) 0.59671(13) 0.0558(5) Uani 1 1 d . . . . . O4 O 0.15646(10) 0.44289(15) 0.65468(12) 0.0503(4) Uani 1 1 d . . . . . O3 O 0.12218(10) 0.64884(14) 0.57969(12) 0.0520(4) Uani 1 1 d . . . . . N1 N 0.29464(14) 0.6463(2) 0.71990(16) 0.0492(5) Uani 1 1 d . . . . . N2 N 0.20674(13) 0.27563(19) 0.51038(17) 0.0484(5) Uani 1 1 d . . . . . C1 C 0.36569(15) 0.6510(2) 0.68545(17) 0.0444(6) Uani 1 1 d . . . . . C6 C 0.39915(16) 0.7759(2) 0.66508(18) 0.0497(6) Uani 1 1 d . . . . . H6 H 0.374142 0.856738 0.677561 0.060 Uiso 1 1 calc R . . . . C5 C 0.46814(17) 0.7788(2) 0.6271(2) 0.0551(7) Uani 1 1 d . . . . . C4 C 0.51066(17) 0.6651(3) 0.6098(2) 0.0627(7) Uani 1 1 d . . . . . H4 H 0.559190 0.671082 0.586867 0.075 Uiso 1 1 calc R . . . . C3 C 0.47779(16) 0.5418(3) 0.62819(19) 0.0562(6) Uani 1 1 d . . . . . H3 H 0.504587 0.462543 0.616290 0.067 Uiso 1 1 calc R . . . . C2 C 0.40607(14) 0.5314(2) 0.66386(16) 0.0438(5) Uani 1 1 d . . . . . C7 C 0.36847(15) 0.3973(2) 0.67171(18) 0.0471(6) Uani 1 1 d . . . . . C8 C 0.23733(16) 0.7598(2) 0.7103(2) 0.0502(6) Uani 1 1 d D . . . . H8A H 0.240932 0.811631 0.645325 0.060 Uiso 0.725(8) 1 calc R . P A 1 H8B H 0.243223 0.822202 0.652215 0.060 Uiso 0.275(8) 1 calc R . P A 2 C21 C 0.14845(17) 0.7093(2) 0.6875(2) 0.0573(7) Uani 1 1 d . . . . . H21A H 0.144484 0.642501 0.742499 0.069 Uiso 1 1 calc R . . . . H21B H 0.111981 0.784609 0.692237 0.069 Uiso 1 1 calc R . . . . C9 C 0.2512(4) 0.8594(7) 0.8035(5) 0.067(2) Uani 0.725(8) 1 d D U P A 1 H9 H 0.215009 0.932529 0.798602 0.080 Uiso 0.725(8) 1 calc R . P A 1 C10 C 0.3120(3) 0.8457(6) 0.8898(4) 0.0834(19) Uani 0.725(8) 1 d D U P A 1 H10A H 0.348490 0.772857 0.895499 0.100 Uiso 0.725(8) 1 calc R . P A 1 H10B H 0.319503 0.908497 0.946725 0.100 Uiso 0.725(8) 1 calc R . P A 1 C11 C 0.14922(14) 0.3454(2) 0.43247(17) 0.0408(5) Uani 1 1 d . . . . . C16 C 0.12812(15) 0.3048(2) 0.32208(17) 0.0478(6) Uani 1 1 d . . . . . H16 H 0.152700 0.228468 0.300400 0.057 Uiso 1 1 calc R . . . . C15 C 0.07090(16) 0.3790(2) 0.24688(18) 0.0491(6) Uani 1 1 d . . . . . C14 C 0.03138(15) 0.4918(2) 0.27065(19) 0.0522(6) Uani 1 1 d . . . . . H14 H -0.008244 0.537709 0.216690 0.063 Uiso 1 1 calc R . . . . C13 C 0.05300(14) 0.5343(2) 0.37828(19) 0.0477(6) Uani 1 1 d . . . . . H13 H 0.028728 0.612714 0.397007 0.057 Uiso 1 1 calc R . . . . C12 C 0.11002(13) 0.4635(2) 0.45995(17) 0.0403(5) Uani 1 1 d . . . . . C18 C 0.26622(16) 0.1805(2) 0.48829(19) 0.0499(6) Uani 1 1 d . . . . . H18 H 0.282077 0.211949 0.422915 0.060 Uiso 1 1 calc R . . . . C22 C 0.34426(16) 0.1790(2) 0.5846(2) 0.0568(7) Uani 1 1 d . . . . . H22A H 0.329244 0.156257 0.651694 0.068 Uiso 1 1 calc R . . . . H22B H 0.382320 0.109861 0.572145 0.068 Uiso 1 1 calc R . . . . C19 C 0.2340(2) 0.0375(2) 0.4672(2) 0.0620(8) Uani 1 1 d . . . . . H19 H 0.268322 -0.025357 0.445706 0.074 Uiso 1 1 calc R . . . . C20 C 0.1627(2) -0.0062(3) 0.4763(2) 0.0735(9) Uani 1 1 d . . . . . H20A H 0.126321 0.053143 0.497648 0.088 Uiso 1 1 calc R . . . . H20B H 0.147854 -0.096755 0.461580 0.088 Uiso 1 1 calc R . . . . C17 C 0.13151(14) 0.5134(2) 0.57378(19) 0.0425(5) Uani 1 1 d . . . . . C10B C 0.2847(7) 0.9521(11) 0.8481(11) 0.073(4) Uani 0.275(8) 1 d D . P A 2 H10C H 0.275171 1.017599 0.792895 0.087 Uiso 0.275(8) 1 calc R . P A 2 H10D H 0.304855 0.977825 0.921280 0.087 Uiso 0.275(8) 1 calc R . P A 2 H2 H 0.2126(13) 0.300(2) 0.5761(18) 0.039(6) Uiso 1 1 d . . . . . H1 H 0.2776(15) 0.568(2) 0.7303(17) 0.049(7) Uiso 1 1 d . . . . . C9B C 0.2700(14) 0.8255(14) 0.8230(10) 0.063(6) Uani 0.275(8) 1 d D U P A 2 H9B H 0.281001 0.765753 0.882244 0.075 Uiso 0.275(8) 1 calc R . P A 2 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 F1 0.0773(12) 0.0657(10) 0.0900(11) 0.0020(8) 0.0282(9) -0.0253(9) F2 0.0885(13) 0.0709(10) 0.0480(8) -0.0019(7) 0.0057(8) -0.0077(8) O2 0.0584(12) 0.0522(10) 0.0560(10) 0.0088(8) 0.0204(9) 0.0025(8) O1 0.0585(12) 0.0450(9) 0.0688(11) -0.0038(8) 0.0253(9) 0.0054(8) O4 0.0585(11) 0.0468(9) 0.0503(9) 0.0030(8) 0.0226(8) 0.0007(8) O3 0.0547(11) 0.0403(9) 0.0603(10) -0.0080(7) 0.0139(8) 0.0048(7) N1 0.0524(13) 0.0413(11) 0.0590(13) 0.0011(9) 0.0236(10) 0.0000(10) N2 0.0593(14) 0.0433(11) 0.0441(12) -0.0015(9) 0.0161(10) 0.0128(9) C1 0.0451(14) 0.0481(13) 0.0394(12) -0.0030(10) 0.0098(10) -0.0031(11) C6 0.0506(16) 0.0432(13) 0.0548(14) -0.0039(11) 0.0133(12) -0.0038(11) C5 0.0549(17) 0.0549(15) 0.0548(15) -0.0023(12) 0.0134(12) -0.0151(13) C4 0.0495(17) 0.0755(19) 0.0679(17) -0.0056(14) 0.0238(13) -0.0108(14) C3 0.0464(15) 0.0607(15) 0.0624(15) -0.0048(12) 0.0162(12) 0.0026(13) C2 0.0415(14) 0.0474(13) 0.0414(12) 0.0006(10) 0.0093(10) 0.0010(11) C7 0.0417(14) 0.0458(13) 0.0500(13) 0.0057(11) 0.0057(11) 0.0109(11) C8 0.0529(16) 0.0425(12) 0.0587(14) -0.0086(11) 0.0209(12) 0.0011(11) C21 0.0579(17) 0.0494(14) 0.0694(16) -0.0151(12) 0.0254(13) 0.0052(12) C9 0.058(4) 0.056(4) 0.084(3) -0.031(3) 0.015(2) 0.004(3) C10 0.091(4) 0.094(4) 0.060(3) -0.022(3) 0.012(3) -0.010(3) C11 0.0420(13) 0.0334(11) 0.0479(13) 0.0051(9) 0.0133(10) -0.0013(9) C16 0.0576(16) 0.0389(11) 0.0469(13) 0.0003(10) 0.0138(11) -0.0017(11) C15 0.0506(15) 0.0496(13) 0.0453(13) -0.0011(11) 0.0096(11) -0.0132(12) C14 0.0419(14) 0.0513(14) 0.0587(15) 0.0090(12) 0.0050(11) -0.0026(11) C13 0.0367(13) 0.0412(12) 0.0658(15) 0.0032(11) 0.0148(11) 0.0009(10) C12 0.0359(13) 0.0365(11) 0.0504(13) 0.0026(10) 0.0145(10) -0.0034(10) C18 0.0645(17) 0.0367(12) 0.0519(14) 0.0031(10) 0.0212(12) 0.0123(11) C22 0.0604(18) 0.0364(12) 0.0727(16) 0.0042(11) 0.0160(14) 0.0119(11) C19 0.083(2) 0.0404(13) 0.0600(15) -0.0030(11) 0.0143(15) 0.0077(14) C20 0.102(3) 0.0514(16) 0.0621(17) 0.0046(13) 0.0124(16) -0.0127(16) C17 0.0364(13) 0.0406(12) 0.0547(14) -0.0007(11) 0.0197(10) 0.0002(10) C10B 0.065(8) 0.066(8) 0.093(8) -0.013(7) 0.029(6) -0.009(6) C9B 0.059(9) 0.041(7) 0.093(10) -0.008(6) 0.029(7) 0.012(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C7 O1 C22 117.77(19) C17 O3 C21 116.72(17) C1 N1 C8 123.6(2) C1 N1 H1 116.0(17) C8 N1 H1 118.2(17) C11 N2 C18 125.1(2) C11 N2 H2 116.1(14) C18 N2 H2 118.0(15) N1 C1 C6 120.6(2) N1 C1 C2 121.9(2) C6 C1 C2 117.4(2) C1 C6 H6 120.0 C5 C6 C1 119.9(2) C5 C6 H6 120.0 F1 C5 C4 118.2(3) C6 C5 F1 117.7(2) C6 C5 C4 124.0(2) C5 C4 H4 121.7 C5 C4 C3 116.5(3) C3 C4 H4 121.7 C4 C3 H3 118.8 C4 C3 C2 122.3(2) C2 C3 H3 118.8 C1 C2 C7 119.8(2) C3 C2 C1 119.7(2) C3 C2 C7 120.3(2) O2 C7 O1 122.8(2) O2 C7 C2 126.4(2) O1 C7 C2 110.8(2) N1 C8 H8A 106.6 N1 C8 H8B 110.5 N1 C8 C21 110.57(19) N1 C8 C9 118.3(3) N1 C8 C9B 100.5(7) C21 C8 H8A 106.6 C21 C8 H8B 110.5 C21 C8 C9B 114.0(9) C9 C8 H8A 106.6 C9 C8 C21 107.6(4) C9B C8 H8B 110.5 O3 C21 C8 110.6(2) O3 C21 H21A 109.5 O3 C21 H21B 109.5 C8 C21 H21A 109.5 C8 C21 H21B 109.5 H21A C21 H21B 108.1 C8 C9 H9 119.3 C10 C9 C8 121.3(6) C10 C9 H9 119.3 C9 C10 H10A 120.0 C9 C10 H10B 120.0 H10A C10 H10B 120.0 N2 C11 C16 121.1(2) N2 C11 C12 121.2(2) C16 C11 C12 117.7(2) C11 C16 H16 120.5 C15 C16 C11 118.9(2) C15 C16 H16 120.5 F2 C15 C16 117.4(2) C14 C15 F2 117.7(2) C14 C15 C16 124.9(2) C15 C14 H14 121.7 C15 C14 C13 116.7(2) C13 C14 H14 121.7 C14 C13 H13 119.0 C14 C13 C12 122.0(2) C12 C13 H13 119.0 C11 C12 C17 120.17(19) C13 C12 C11 119.82(19) C13 C12 C17 119.98(19) N2 C18 H18 108.0 N2 C18 C22 109.70(19) N2 C18 C19 114.2(2) C22 C18 H18 108.0 C19 C18 H18 108.0 C19 C18 C22 108.69(19) O1 C22 C18 110.62(18) O1 C22 H22A 109.5 O1 C22 H22B 109.5 C18 C22 H22A 109.5 C18 C22 H22B 109.5 H22A C22 H22B 108.1 C18 C19 H19 117.0 C20 C19 C18 125.9(3) C20 C19 H19 117.0 C19 C20 H20A 120.0 C19 C20 H20B 120.0 H20A C20 H20B 120.0 O4 C17 O3 122.57(19) O4 C17 C12 124.93(19) O3 C17 C12 112.49(19) H10C C10B H10D 120.0 C9B C10B H10C 120.0 C9B C10B H10D 120.0 C8 C9B H9B 115.3 C10B C9B C8 129.4(13) C10B C9B H9B 115.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C5 1.361(3) F2 C15 1.364(3) O2 C7 1.207(3) O1 C7 1.359(3) O1 C22 1.440(3) O4 C17 1.212(2) O3 C21 1.441(3) O3 C17 1.346(2) N1 C1 1.365(3) N1 C8 1.453(3) N1 H1 0.84(2) N2 C11 1.362(3) N2 C18 1.443(3) N2 H2 0.84(2) C1 C6 1.401(3) C1 C2 1.416(3) C6 H6 0.9300 C6 C5 1.358(3) C5 C4 1.372(4) C4 H4 0.9300 C4 C3 1.375(3) C3 H3 0.9300 C3 C2 1.388(3) C2 C7 1.475(3) C8 H8A 0.9800 C8 H8B 0.9800 C8 C21 1.516(4) C8 C9 1.500(5) C8 C9B 1.524(9) C21 H21A 0.9700 C21 H21B 0.9700 C9 H9 0.9300 C9 C10 1.282(7) C10 H10A 0.9300 C10 H10B 0.9300 C11 C16 1.401(3) C11 C12 1.420(3) C16 H16 0.9300 C16 C15 1.365(3) C15 C14 1.363(3) C14 H14 0.9300 C14 C13 1.374(3) C13 H13 0.9300 C13 C12 1.389(3) C12 C17 1.469(3) C18 H18 0.9800 C18 C22 1.526(4) C18 C19 1.504(3) C22 H22A 0.9700 C22 H22B 0.9700 C19 H19 0.9300 C19 C20 1.297(4) C20 H20A 0.9300 C20 H20B 0.9300 C10B H10C 0.9300 C10B H10D 0.9300 C10B C9B 1.292(10) C9B H9B 0.9300