#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116129.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_7116129 loop_ _publ_author_name 'L. Turunen' 'N. K. Beyeh' 'F. Pan' 'A. Valkonen' 'K. Rissanen' _publ_section_title ; Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors ; _journal_name_full Chem.Commun. _journal_page_first 15920 _journal_paper_doi 10.1039/C4cc07771G _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C68 H76 I4 O8, 7(C5 H5 N)' _chemical_formula_sum 'C103 H111 I4 N7 O8' _chemical_formula_weight 2082.58 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2014-02-11 _audit_creation_method ; Olex2 1.2 (compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) ; _cell_angle_alpha 90 _cell_angle_beta 90.8176(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 27.3028(5) _cell_length_b 12.2692(2) _cell_length_c 29.3240(5) _cell_measurement_reflns_used 9141 _cell_measurement_temperature 123.01(10) _cell_measurement_theta_max 75.3830 _cell_measurement_theta_min 3.9400 _cell_volume 9822.1(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 123.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1977 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0479110000 _diffrn_orient_matrix_UB_12 0.0087794000 _diffrn_orient_matrix_UB_13 -0.0268496000 _diffrn_orient_matrix_UB_21 -0.0295087000 _diffrn_orient_matrix_UB_22 -0.0034341000 _diffrn_orient_matrix_UB_23 -0.0451612000 _diffrn_orient_matrix_UB_31 -0.0041501000 _diffrn_orient_matrix_UB_32 0.1252212000 _diffrn_orient_matrix_UB_33 0.0006448000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.0486 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 19709 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 66.750 _diffrn_reflns_theta_max 76.848 _diffrn_reflns_theta_min 3.014 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 10.416 _exptl_absorpt_correction_T_max 0.232 _exptl_absorpt_correction_T_min 0.040 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_description brick _exptl_crystal_F_000 4216 _exptl_crystal_size_max 0.5087 _exptl_crystal_size_mid 0.151 _exptl_crystal_size_min 0.1181 _refine_diff_density_max 1.155 _refine_diff_density_min -0.802 _refine_diff_density_rms 0.078 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 592 _refine_ls_number_reflns 10048 _refine_ls_number_restraints 43 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0429 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+6.1300P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1141 _refine_ls_wR_factor_ref 0.1204 _reflns_Friedel_coverage 0.000 _reflns_number_gt 8788 _reflns_number_total 10048 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc07771g2.cif _cod_data_source_block 4c.Pyridine _cod_original_cell_volume 9822.0(3) _cod_database_code 7116129 #BEGIN Tags that were not found in dictionaries: _shelxl_version_number 2013-4 _chemical_oxdiff_formula 'C60 H60 O8 N4 I4' _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 99.75 _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 At 1.5 times of: All C(H,H,H) groups 2. Shared sites {C31A, C31B} 3. Restrained distances H32B-H46 2.1 with sigma of 0.02 4. Uiso/Uaniso restraints and constraints N3 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(C47) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C31A) = Uanis(C31B) 5. Others Sof(I1B)=1-FVAR(1) Sof(I1A)=FVAR(1) Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31C)=Sof(H31D)=Sof(C32B)=Sof(H32C)= Sof(H32D)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34D)=Sof(H34E)= Sof(H34F)=1-FVAR(2) Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(C32A)=Sof(H32A)= Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=Sof(H34B)= Sof(H34C)=FVAR(2) 6.a Ternary CH refined with riding coordinates: C11(H11), C28(H28) 6.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B), C30(H30A,H30B), C30(H30C,H30D), C31A(H31A,H31B), C32A(H32A,H32B), C33A(H33A, H33B), C31B(H31C,H31D), C32B(H32C,H32D), C33B(H33C,H33D) 6.c Aromatic/amide H refined with riding coordinates: C6(H6), C23(H23), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44) 6.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C34A(H34A,H34B,H34C), C34B(H34D,H34E,H34F) ; #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 I1A I 0.74250(2) 0.78761(19) 0.38969(4) 0.0534(3) Uani 0.872(8) 1 d . . P A 1 I1B I 0.7383(4) 0.7433(13) 0.3980(3) 0.0649(18) Uani 0.128(8) 1 d . . P A 2 I2 I 0.92869(2) 0.94474(2) 0.08129(2) 0.05277(9) Uani 1 1 d . . . . . O1 O 0.80237(9) 0.5243(2) 0.24876(8) 0.0467(5) Uani 1 1 d . . . . . O2 O 0.85559(9) 0.5811(2) 0.16836(8) 0.0451(5) Uani 1 1 d . . . . . O3 O 1.01284(9) 0.5880(2) 0.09865(8) 0.0455(5) Uani 1 1 d . . . . . O4 O 1.11364(9) 0.5345(2) 0.10620(8) 0.0471(5) Uani 1 1 d . . . . . C1 C 0.78169(14) 0.6705(4) 0.35582(13) 0.0567(10) Uani 1 1 d . . . . . C2 C 0.80914(14) 0.6093(4) 0.33877(12) 0.0510(8) Uani 1 1 d . . . . . C3 C 0.84508(13) 0.5347(3) 0.32107(11) 0.0443(7) Uani 1 1 d . . . . . C4 C 0.88405(12) 0.4989(3) 0.34914(10) 0.0422(7) Uani 1 1 d . . . . . C5 C 0.91842(12) 0.4245(3) 0.33391(10) 0.0384(6) Uani 1 1 d . . . . . C6 C 0.91388(11) 0.3884(3) 0.28881(10) 0.0387(6) Uani 1 1 d . . . . . H6 H 0.9378 0.3393 0.2776 0.046 Uiso 1 1 calc R . . . . C7 C 0.87597(12) 0.4209(3) 0.25956(10) 0.0388(6) Uani 1 1 d . . . . . C8 C 0.84157(12) 0.4953(3) 0.27603(11) 0.0419(7) Uani 1 1 d . . . . . C9 C 0.80398(14) 0.6333(4) 0.23027(12) 0.0512(8) Uani 1 1 d . . . . . H9A H 0.8005 0.6863 0.2555 0.061 Uiso 1 1 calc R . . . . H9B H 0.7758 0.6434 0.2090 0.061 Uiso 1 1 calc R . . . . C10 C 0.85074(14) 0.6573(3) 0.20530(13) 0.0501(8) Uani 1 1 d . . . . . H10A H 0.8499 0.7327 0.1932 0.060 Uiso 1 1 calc R . . . . H10B H 0.8791 0.6508 0.2265 0.060 Uiso 1 1 calc R . . . . C11 C 0.87230(11) 0.3787(3) 0.21067(10) 0.0388(6) Uani 1 1 d . . . . . H11 H 0.8398 0.4028 0.1982 0.047 Uiso 1 1 calc R . . . . C12 C 0.87251(12) 0.2545(3) 0.20917(11) 0.0431(7) Uani 1 1 d . . . . . H12A H 0.9014 0.2269 0.2264 0.052 Uiso 1 1 calc R . . . . H12B H 0.8754 0.2301 0.1771 0.052 Uiso 1 1 calc R . . . . C13 C 0.82602(14) 0.2064(3) 0.22942(13) 0.0499(8) Uani 1 1 d . . . . . H13A H 0.8228 0.2331 0.2611 0.060 Uiso 1 1 calc R . . . . H13B H 0.7974 0.2333 0.2117 0.060 Uiso 1 1 calc R . . . . C14 C 0.82493(16) 0.0841(4) 0.22981(14) 0.0566(9) Uani 1 1 d . . . . . H14A H 0.8387 0.0570 0.2009 0.068 Uiso 1 1 calc R . . . . H14B H 0.7904 0.0597 0.2310 0.068 Uiso 1 1 calc R . . . . C15 C 0.85310(18) 0.0329(4) 0.26928(16) 0.0616(10) Uani 1 1 d . . . . . H15A H 0.8378 0.0545 0.2983 0.074 Uiso 1 1 calc R . . . . H15B H 0.8871 0.0607 0.2696 0.074 Uiso 1 1 calc R . . . . C16 C 0.8539(2) -0.0904(5) 0.2659(2) 0.0773(13) Uani 1 1 d . . . . . H16A H 0.8198 -0.1173 0.2633 0.093 Uiso 1 1 calc R . . . . H16B H 0.8710 -0.1115 0.2376 0.093 Uiso 1 1 calc R . . . . C17 C 0.8786(3) -0.1447(5) 0.3057(2) 0.0885(17) Uani 1 1 d . . . . . H17A H 0.8821 -0.2228 0.2995 0.133 Uiso 1 1 calc GR . . . . H17B H 0.8589 -0.1345 0.3330 0.133 Uiso 1 1 calc GR . . . . H17C H 0.9111 -0.1124 0.3107 0.133 Uiso 1 1 calc GR . . . . C18 C 0.91113(12) 0.4333(3) 0.18188(10) 0.0387(6) Uani 1 1 d . . . . . C19 C 0.90144(12) 0.5353(3) 0.16318(10) 0.0403(6) Uani 1 1 d . . . . . C20 C 0.93614(12) 0.5906(3) 0.13666(11) 0.0421(7) Uani 1 1 d . . . . . C21 C 0.98062(12) 0.5380(3) 0.12840(10) 0.0406(6) Uani 1 1 d . . . . . C22 C 0.99184(12) 0.4363(3) 0.14621(10) 0.0383(6) Uani 1 1 d . . . . . C23 C 0.95665(11) 0.3857(3) 0.17337(10) 0.0374(6) Uani 1 1 d . . . . . H23 H 0.9640 0.3167 0.1865 0.045 Uiso 1 1 calc R . . . . C24 C 0.92750(13) 0.6981(3) 0.11899(12) 0.0467(7) Uani 1 1 d . . . . . C25 C 0.92479(15) 0.7888(3) 0.10492(12) 0.0503(8) Uani 1 1 d . . . . . C26 C 1.04670(13) 0.6635(3) 0.11956(12) 0.0478(7) Uani 1 1 d . . . . . H26A H 1.0480 0.6520 0.1530 0.057 Uiso 1 1 calc R . . . . H26B H 1.0360 0.7393 0.1135 0.057 Uiso 1 1 calc R . . . . C27 C 1.09660(14) 0.6440(3) 0.09953(12) 0.0504(8) Uani 1 1 d . . . . . H27A H 1.0951 0.6599 0.0664 0.061 Uiso 1 1 calc R . . . . H27B H 1.1204 0.6951 0.1137 0.061 Uiso 1 1 calc R . . . . C28 C 1.04045(12) 0.3831(3) 0.13495(10) 0.0395(6) Uani 1 1 d . . . . . H28 H 1.0487 0.4077 0.1035 0.047 Uiso 1 1 calc R . . . . C29 C 1.03855(12) 0.2578(3) 0.13325(11) 0.0426(7) Uani 1 1 d . . . . . H29A H 1.0386 0.2288 0.1647 0.051 Uiso 1 1 calc R . . . . H29B H 1.0077 0.2347 0.1180 0.051 Uiso 1 1 calc R . . . . C30 C 1.08186(15) 0.2102(4) 0.10770(16) 0.0601(10) Uani 1 1 d . . . . . H30A H 1.0832 0.2442 0.0771 0.072 Uiso 0.659(13) 1 calc R . P B 1 H30B H 1.1125 0.2295 0.1243 0.072 Uiso 0.659(13) 1 calc R . P B 1 H30C H 1.0832 0.2442 0.0771 0.072 Uiso 0.341(13) 1 calc R . P B 2 H30D H 1.1125 0.2295 0.1243 0.072 Uiso 0.341(13) 1 calc R . P B 2 C31A C 1.07980(19) 0.0893(5) 0.1021(2) 0.0772(16) Uani 0.659(13) 1 d . . P B 1 H31A H 1.0467 0.0669 0.0915 0.093 Uiso 0.659(13) 1 calc R . P B 1 H31B H 1.0868 0.0531 0.1317 0.093 Uiso 0.659(13) 1 calc R . P B 1 C32A C 1.1199(2) 0.0548(5) 0.0654(3) 0.0541(18) Uani 0.659(13) 1 d . . P B 1 H32A H 1.1135 0.0946 0.0366 0.065 Uiso 0.659(13) 1 calc R . P B 1 H32B H 1.1528 0.0763 0.0768 0.065 Uiso 0.659(13) 1 calc DR . P B 1 C33A C 1.1195(3) -0.0657(6) 0.0561(3) 0.065(2) Uani 0.659(13) 1 d . . P B 1 H33A H 1.0865 -0.0863 0.0446 0.078 Uiso 0.659(13) 1 calc R . P B 1 H33B H 1.1251 -0.1048 0.0853 0.078 Uiso 0.659(13) 1 calc R . P B 1 C34A C 1.1569(5) -0.1038(9) 0.0224(4) 0.074(3) Uani 0.659(13) 1 d . . P B 1 H34A H 1.1545 -0.0593 -0.0052 0.111 Uiso 0.659(13) 1 calc GR . P B 1 H34B H 1.1507 -0.1804 0.0147 0.111 Uiso 0.659(13) 1 calc GR . P B 1 H34C H 1.1897 -0.0966 0.0359 0.111 Uiso 0.659(13) 1 calc GR . P B 1 C31B C 1.07980(19) 0.0893(5) 0.1021(2) 0.0772(16) Uani 0.341(13) 1 d . . P B 2 H31C H 1.0654 0.0634 0.1310 0.093 Uiso 0.341(13) 1 calc R . P B 2 H31D H 1.0541 0.0780 0.0785 0.093 Uiso 0.341(13) 1 calc R . P B 2 C32B C 1.1167(5) 0.0072(10) 0.0917(4) 0.054(3) Uani 0.341(13) 1 d . . P B 2 H32C H 1.1046 -0.0676 0.0972 0.065 Uiso 0.341(13) 1 calc R . P B 2 H32D H 1.1474 0.0190 0.1094 0.065 Uiso 0.341(13) 1 calc R . P B 2 C33B C 1.1235(5) 0.0291(15) 0.0416(6) 0.062(4) Uani 0.341(13) 1 d . . P B 2 H33C H 1.1329 0.1063 0.0373 0.075 Uiso 0.341(13) 1 calc R . P B 2 H33D H 1.0920 0.0170 0.0252 0.075 Uiso 0.341(13) 1 calc R . P B 2 C34B C 1.1638(8) -0.046(2) 0.0204(6) 0.080(7) Uani 0.341(13) 1 d . . P B 2 H34D H 1.1718 -0.0197 -0.0102 0.121 Uiso 0.341(13) 1 calc GR . P B 2 H34E H 1.1514 -0.1210 0.0183 0.121 Uiso 0.341(13) 1 calc GR . P B 2 H34F H 1.1933 -0.0446 0.0398 0.121 Uiso 0.341(13) 1 calc GR . P B 2 N3 N 1.2534(2) 0.3632(6) 0.1516(3) 0.115(2) Uani 1 1 d . . . . . C45 C 1.2263(4) 0.2732(10) 0.1441(4) 0.145(4) Uani 1 1 d . . . . . H45 H 1.2077 0.2412 0.1678 0.174 Uiso 1 1 calc R . . . . C46 C 1.2265(4) 0.2339(10) 0.1056(6) 0.162(5) Uani 1 1 d . . . . . H46 H 1.2061 0.1717 0.1016 0.194 Uiso 1 1 calc DR . . . . C47 C 1.2493(4) 0.2623(9) 0.0703(4) 0.122(3) Uani 1 1 d . U . . . H47 H 1.2462 0.2228 0.0425 0.146 Uiso 1 1 calc R . . . . C48 C 1.2779(4) 0.3504(10) 0.0736(4) 0.146(4) Uani 1 1 d . . . . . H48 H 1.2948 0.3776 0.0479 0.175 Uiso 1 1 calc R . . . . C49 C 1.2823(4) 0.4019(8) 0.1165(4) 0.127(3) Uani 1 1 d . . . . . H49 H 1.3043 0.4609 0.1212 0.153 Uiso 1 1 calc R . . . . N4 N 1.0000 0.0950(7) 0.2500 0.0823(17) Uani 1 2 d S T P . . C50 C 0.9829(2) 0.0366(6) 0.21477(19) 0.0805(15) Uani 1 1 d . . . . . H50 H 0.9708 0.0750 0.1888 0.097 Uiso 1 1 calc R . . . . C51 C 0.9814(2) -0.0755(6) 0.21357(19) 0.0852(16) Uani 1 1 d . . . . . H51 H 0.9678 -0.1123 0.1879 0.102 Uiso 1 1 calc R . . . . C52 C 1.0000 -0.1339(9) 0.2500 0.096(3) Uani 1 2 d S T P . . H52 H 1.0000 -0.2113 0.2500 0.116 Uiso 1 2 calc RS T P . . N1 N 0.94175(14) 1.1557(3) 0.04893(11) 0.0572(8) Uani 1 1 d . . . . . C35 C 0.97696(19) 1.1774(4) 0.01938(14) 0.0641(11) Uani 1 1 d . . . . . H35 H 0.9954 1.1178 0.0081 0.077 Uiso 1 1 calc R . . . . C36 C 0.9883(2) 1.2787(5) 0.00420(17) 0.0767(14) Uani 1 1 d . . . . . H36 H 1.0140 1.2897 -0.0169 0.092 Uiso 1 1 calc R . . . . C37 C 0.9616(2) 1.3647(5) 0.0204(2) 0.0798(15) Uani 1 1 d . . . . . H37 H 0.9682 1.4368 0.0104 0.096 Uiso 1 1 calc R . . . . C38 C 0.9254(2) 1.3456(4) 0.05099(19) 0.0729(14) Uani 1 1 d . . . . . H38 H 0.9068 1.4042 0.0630 0.087 Uiso 1 1 calc R . . . . C39 C 0.91620(17) 1.2398(4) 0.06417(14) 0.0596(10) Uani 1 1 d . . . . . H39 H 0.8905 1.2267 0.0850 0.071 Uiso 1 1 calc R . . . . N2 N 0.69912(14) 0.9349(4) 0.44724(12) 0.0622(9) Uani 1 1 d . . . . . C40 C 0.70244(16) 0.9065(4) 0.49073(15) 0.0606(10) Uani 1 1 d . . . . . H40 H 0.7182 0.8396 0.4980 0.073 Uiso 1 1 calc R . . . . C41 C 0.68464(17) 0.9674(5) 0.52573(15) 0.0663(11) Uani 1 1 d . . . . . H41 H 0.6891 0.9444 0.5564 0.080 Uiso 1 1 calc R . . . . C42 C 0.66056(19) 1.0610(5) 0.51594(18) 0.0712(12) Uani 1 1 d . . . . . H42 H 0.6467 1.1031 0.5397 0.085 Uiso 1 1 calc R . . . . C43 C 0.65627(19) 1.0942(4) 0.4722(2) 0.0744(13) Uani 1 1 d . . . . . H43 H 0.6396 1.1600 0.4649 0.089 Uiso 1 1 calc R . . . . C44 C 0.67654(19) 1.0309(5) 0.43791(17) 0.0742(14) Uani 1 1 d . . . . . H44 H 0.6745 1.0557 0.4072 0.089 Uiso 1 1 calc R . . . . 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 I1A 0.04548(17) 0.0724(7) 0.0423(3) -0.0206(3) 0.00249(13) 0.0095(2) I1B 0.0608(19) 0.071(4) 0.0630(18) -0.014(3) -0.0138(14) 0.024(2) I2 0.06165(15) 0.05057(14) 0.04593(13) 0.00751(9) -0.00472(10) 0.00848(10) O1 0.0359(11) 0.0631(15) 0.0411(11) -0.0091(11) -0.0012(9) 0.0055(10) O2 0.0410(12) 0.0553(14) 0.0389(11) -0.0033(10) -0.0007(9) 0.0107(10) O3 0.0436(12) 0.0565(14) 0.0363(10) 0.0093(10) 0.0017(9) -0.0010(10) O4 0.0438(12) 0.0651(15) 0.0324(10) 0.0114(10) 0.0052(9) 0.0010(11) C1 0.0457(18) 0.082(3) 0.0419(17) -0.0204(18) 0.0002(14) 0.0127(18) C2 0.0429(17) 0.071(2) 0.0396(15) -0.0132(16) 0.0001(13) 0.0020(16) C3 0.0398(16) 0.0557(19) 0.0375(15) -0.0097(14) 0.0062(12) 0.0025(14) C4 0.0394(15) 0.0554(19) 0.0319(13) -0.0077(13) 0.0059(11) -0.0028(14) C5 0.0373(14) 0.0472(17) 0.0309(13) -0.0030(12) 0.0039(11) -0.0040(12) C6 0.0362(14) 0.0479(17) 0.0322(13) -0.0029(12) 0.0039(11) -0.0031(12) C7 0.0366(14) 0.0485(17) 0.0315(13) -0.0042(12) 0.0039(11) -0.0032(13) C8 0.0366(15) 0.0537(19) 0.0354(14) -0.0068(13) 0.0023(11) -0.0001(13) C9 0.0446(17) 0.065(2) 0.0444(16) -0.0071(16) 0.0004(13) 0.0120(16) C10 0.0488(18) 0.056(2) 0.0459(17) -0.0054(15) 0.0045(14) 0.0090(15) C11 0.0373(14) 0.0507(18) 0.0284(12) -0.0051(12) 0.0006(10) 0.0008(12) C12 0.0421(16) 0.0530(19) 0.0341(14) -0.0098(13) 0.0017(12) -0.0035(14) C13 0.0463(18) 0.058(2) 0.0451(17) -0.0054(15) 0.0054(14) -0.0056(15) C14 0.055(2) 0.060(2) 0.055(2) -0.0093(17) 0.0061(16) -0.0094(18) C15 0.062(2) 0.060(2) 0.063(2) -0.0002(19) 0.0030(19) -0.0042(19) C16 0.086(3) 0.062(3) 0.084(3) 0.002(2) -0.008(3) -0.007(3) C17 0.098(4) 0.071(3) 0.097(4) 0.014(3) -0.014(3) -0.004(3) C18 0.0393(15) 0.0478(17) 0.0290(12) -0.0044(11) -0.0008(11) 0.0007(13) C19 0.0393(15) 0.0486(18) 0.0329(13) -0.0051(12) -0.0012(11) 0.0061(13) C20 0.0417(16) 0.0488(18) 0.0356(14) 0.0011(13) -0.0017(12) 0.0038(13) C21 0.0403(15) 0.0496(18) 0.0317(13) 0.0036(12) 0.0010(11) 0.0007(13) C22 0.0384(15) 0.0470(17) 0.0294(12) -0.0005(11) -0.0002(11) 0.0014(12) C23 0.0390(15) 0.0445(16) 0.0287(12) -0.0016(11) -0.0007(10) 0.0028(12) C24 0.0455(17) 0.055(2) 0.0391(15) 0.0023(14) -0.0036(13) 0.0037(15) C25 0.054(2) 0.054(2) 0.0432(16) 0.0080(15) -0.0042(14) 0.0082(16) C26 0.0438(17) 0.055(2) 0.0451(16) 0.0085(14) 0.0002(13) -0.0037(15) C27 0.0464(18) 0.064(2) 0.0408(16) 0.0173(15) 0.0031(13) -0.0008(16) C28 0.0398(15) 0.0511(18) 0.0278(12) 0.0014(11) 0.0028(11) 0.0043(13) C29 0.0413(16) 0.0524(19) 0.0340(13) -0.0038(13) -0.0009(12) 0.0074(14) C30 0.0438(19) 0.075(3) 0.062(2) -0.021(2) 0.0036(16) 0.0107(18) C31A 0.066(3) 0.076(3) 0.089(3) -0.042(3) -0.019(2) 0.024(2) C32A 0.057(4) 0.049(4) 0.057(5) -0.009(3) 0.002(3) 0.008(2) C33A 0.080(5) 0.057(4) 0.059(4) -0.005(3) 0.007(3) 0.013(3) C34A 0.083(6) 0.075(6) 0.063(5) -0.014(5) -0.011(4) 0.028(5) C31B 0.066(3) 0.076(3) 0.089(3) -0.042(3) -0.019(2) 0.024(2) C32B 0.068(7) 0.052(7) 0.042(6) -0.001(5) 0.003(5) 0.024(5) C33B 0.051(7) 0.086(11) 0.051(7) -0.007(7) 0.000(5) 0.017(6) C34B 0.070(11) 0.13(2) 0.040(6) 0.005(11) 0.015(6) 0.047(14) N3 0.083(4) 0.124(5) 0.137(6) -0.027(4) -0.021(4) 0.031(4) C45 0.112(7) 0.157(9) 0.168(10) -0.032(8) 0.038(7) -0.048(6) C46 0.130(8) 0.130(8) 0.226(14) -0.053(9) 0.011(9) -0.027(7) C47 0.107(5) 0.129(6) 0.129(6) -0.050(5) -0.025(4) 0.036(5) C48 0.141(8) 0.155(9) 0.142(8) 0.028(7) 0.036(7) 0.028(7) C49 0.119(7) 0.112(6) 0.151(8) -0.027(6) 0.009(6) -0.017(5) N4 0.078(4) 0.096(5) 0.073(4) 0.000 0.005(3) 0.000 C50 0.077(3) 0.101(4) 0.063(3) 0.010(3) 0.000(2) 0.006(3) C51 0.093(4) 0.106(5) 0.056(3) -0.006(3) -0.006(3) -0.002(3) C52 0.122(8) 0.103(7) 0.065(4) 0.000 -0.014(5) 0.000 N1 0.070(2) 0.0552(19) 0.0466(16) 0.0047(13) -0.0002(14) 0.0084(16) C35 0.073(3) 0.075(3) 0.0445(18) 0.0025(18) 0.0020(18) 0.017(2) C36 0.077(3) 0.097(4) 0.055(2) 0.025(2) -0.004(2) -0.005(3) C37 0.086(4) 0.061(3) 0.092(4) 0.023(3) -0.027(3) -0.010(3) C38 0.078(3) 0.057(3) 0.083(3) -0.016(2) -0.031(3) 0.019(2) C39 0.062(2) 0.070(3) 0.0471(18) -0.0057(18) -0.0041(16) 0.008(2) N2 0.0529(18) 0.087(3) 0.0466(16) -0.0108(17) 0.0019(14) 0.0060(17) C40 0.056(2) 0.075(3) 0.051(2) -0.0011(19) 0.0063(16) 0.011(2) C41 0.057(2) 0.093(3) 0.049(2) -0.008(2) 0.0122(17) 0.006(2) C42 0.064(3) 0.082(3) 0.067(3) -0.014(2) 0.013(2) 0.006(2) C43 0.062(3) 0.059(3) 0.102(4) 0.004(3) -0.002(3) -0.002(2) C44 0.066(3) 0.102(4) 0.055(2) 0.019(2) -0.014(2) -0.018(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' I I -0.3257 6.8362 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -18 -1 0 0.1065 -17.9999 -1.0000 -0.0001 -0.8712 0.5346 -0.0505 18 0 0 0.0592 17.9998 -0.0000 -0.0001 0.8624 -0.5311 -0.0747 4 8 0 0.2073 4.0007 8.0002 0.0018 0.2619 -0.1456 0.9852 -6 -8 0 0.2421 -6.0007 -8.0002 -0.0018 -0.3577 0.2046 -0.9769 0 0 -19 0.0574 -0.0003 0.0001 -19.0000 0.5101 0.8581 -0.0122 0 0 19 0.0607 0.0003 -0.0001 19.0000 -0.5101 -0.8581 0.0122 -14 0 -11 0.1016 -14.0000 0.0001 -10.9999 -0.3754 0.9099 0.0510 14 0 11 0.0705 14.0000 -0.0001 10.9999 0.3754 -0.9099 -0.0510 -18 0 0 0.0918 -17.9998 0.0000 0.0001 -0.8624 0.5311 0.0747 -14 0 11 0.0869 -13.9996 -0.0000 11.0001 -0.9661 -0.0837 0.0652 10 0 15 0.0558 10.0001 -0.0001 14.9999 0.0764 -0.9725 -0.0318 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 C8 O1 C9 115.5(3) . . C19 O2 C10 116.1(3) . . C21 O3 C26 115.2(3) . . C4 O4 C27 115.8(3) 2_755 . C2 C1 I1A 171.8(4) . . C2 C1 I1B 164.0(6) . . C1 C2 C3 175.6(4) . . C4 C3 C2 120.0(3) . . C4 C3 C8 118.9(3) . . C8 C3 C2 121.1(3) . . O4 C4 C3 118.7(3) 2_755 . O4 C4 C5 119.4(3) 2_755 . C5 C4 C3 121.8(3) . . C4 C5 C6 117.5(3) . . C4 C5 C28 121.5(3) . 2_755 C6 C5 C28 121.0(3) . 2_755 C7 C6 C5 123.1(3) . . C6 C7 C8 118.1(3) . . C6 C7 C11 121.3(3) . . C8 C7 C11 120.7(3) . . O1 C8 C3 119.9(3) . . O1 C8 C7 119.3(3) . . C7 C8 C3 120.6(3) . . O1 C9 C10 113.2(3) . . O2 C10 C9 109.0(3) . . C12 C11 C7 111.5(3) . . C18 C11 C7 109.6(3) . . C18 C11 C12 114.9(3) . . C11 C12 C13 111.8(3) . . C14 C13 C12 113.9(3) . . C13 C14 C15 114.2(4) . . C14 C15 C16 111.7(4) . . C17 C16 C15 113.5(5) . . C19 C18 C11 119.1(3) . . C19 C18 C23 118.0(3) . . C23 C18 C11 122.9(3) . . O2 C19 C18 119.3(3) . . O2 C19 C20 118.9(3) . . C18 C19 C20 121.7(3) . . C19 C20 C24 122.2(3) . . C21 C20 C19 117.8(3) . . C21 C20 C24 120.0(3) . . O3 C21 C20 117.6(3) . . C22 C21 O3 119.7(3) . . C22 C21 C20 122.5(3) . . C21 C22 C23 117.6(3) . . C21 C22 C28 119.6(3) . . C23 C22 C28 122.7(3) . . C18 C23 C22 122.3(3) . . C25 C24 C20 174.0(4) . . C24 C25 I2 173.4(4) . . O3 C26 C27 108.1(3) . . O4 C27 C26 112.8(3) . . C5 C28 C29 112.1(3) 2_755 . C22 C28 C5 111.4(3) . 2_755 C22 C28 C29 114.0(3) . . C30 C29 C28 111.9(3) . . C31A C30 C29 114.0(4) . . C30 C31A C32A 108.1(5) . . C33A C32A C31A 112.2(6) . . C32A C33A C34A 114.9(8) . . C32B C33B C34B 112.2(12) . . C45 N3 C49 118.5(9) . . C46 C45 N3 117.5(11) . . C45 C46 C47 130.8(12) . . C46 C47 C48 117.2(10) . . C47 C48 C49 118.1(11) . . N3 C49 C48 117.7(9) . . C50 N4 C50 115.1(8) . 2_755 N4 C50 C51 124.4(6) . . C50 C51 C52 119.3(7) . . C51 C52 C51 117.3(10) . 2_755 C39 N1 C35 116.8(4) . . N1 C35 C36 124.6(5) . . C35 C36 C37 117.7(5) . . C38 C37 C36 119.3(5) . . C37 C38 C39 118.9(5) . . N1 C39 C38 122.6(5) . . C40 N2 C44 116.6(4) . . N2 C40 C41 124.1(5) . . C42 C41 C40 118.9(5) . . C43 C42 C41 119.6(5) . . C42 C43 C44 119.3(5) . . N2 C44 C43 121.5(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 I1A C1 2.056(4) . I1B C1 1.941(6) . I2 C25 2.038(4) . O1 C8 1.374(4) . O1 C9 1.443(5) . O2 C10 1.439(4) . O2 C19 1.382(4) . O3 C21 1.390(4) . O3 C26 1.439(5) . O4 C4 1.381(4) 2_755 O4 C27 1.435(5) . C1 C2 1.178(6) . C2 C3 1.444(5) . C3 C4 1.406(5) . C3 C8 1.408(4) . C4 O4 1.381(4) 2_755 C4 C5 1.387(5) . C5 C6 1.399(4) . C5 C28 1.524(4) 2_755 C6 C7 1.393(5) . C7 C8 1.400(5) . C7 C11 1.527(4) . C9 C10 1.510(5) . C11 C12 1.524(5) . C11 C18 1.520(4) . C12 C13 1.528(5) . C13 C14 1.501(6) . C14 C15 1.516(6) . C15 C16 1.517(7) . C16 C17 1.497(8) . C18 C19 1.391(5) . C18 C23 1.399(4) . C19 C20 1.408(5) . C20 C21 1.400(5) . C20 C24 1.436(5) . C21 C22 1.385(5) . C22 C23 1.402(4) . C22 C28 1.520(4) . C24 C25 1.190(6) . C26 C27 1.510(5) . C28 C5 1.524(4) 2_755 C28 C29 1.538(5) . C29 C30 1.525(5) . C30 C31A 1.493(7) . C31A C32A 1.604(9) . C32A C33A 1.504(10) . C33A C34A 1.505(14) . C32B C33B 1.509(19) . C33B C34B 1.57(2) . N3 C45 1.346(12) . N3 C49 1.389(13) . C45 C46 1.230(16) . C46 C47 1.264(17) . C47 C48 1.336(15) . C48 C49 1.409(15) . N4 C50 1.337(8) . N4 C50 1.337(8) 2_755 C50 C51 1.376(9) . C51 C52 1.377(8) . C52 C51 1.377(8) 2_755 N1 C35 1.330(6) . N1 C39 1.327(6) . C35 C36 1.358(8) . C36 C37 1.371(9) . C37 C38 1.365(9) . C38 C39 1.378(8) . N2 C40 1.324(6) . N2 C44 1.356(7) . C40 C41 1.364(6) . C41 C42 1.352(8) . C42 C43 1.348(8) . C43 C44 1.392(8) . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 O1 C9 C10 O2 59.3(4) . . O2 C19 C20 C21 -174.2(3) . . O2 C19 C20 C24 7.0(5) . . O3 C21 C22 C23 -175.5(3) . . O3 C21 C22 C28 3.1(5) . . O3 C26 C27 O4 -58.4(4) . . O4 C4 C5 C6 178.3(3) 2_755 . O4 C4 C5 C28 -1.5(5) 2_755 2_755 C2 C3 C4 O4 1.5(5) . 2_755 C2 C3 C4 C5 177.9(3) . . C2 C3 C8 O1 -2.7(6) . . C2 C3 C8 C7 -178.5(4) . . C3 C4 C5 C6 1.9(5) . . C3 C4 C5 C28 -177.9(3) . 2_755 C4 O4 C27 C26 -56.4(4) 2_755 . C4 C3 C8 O1 176.4(3) . . C4 C3 C8 C7 0.6(5) . . C4 C5 C6 C7 -2.1(5) . . C5 C6 C7 C8 1.5(5) . . C5 C6 C7 C11 -179.5(3) . . C5 C28 C29 C30 -70.4(3) 2_755 . C6 C7 C8 O1 -176.5(3) . . C6 C7 C8 C3 -0.7(5) . . C6 C7 C11 C12 54.5(4) . . C6 C7 C11 C18 -73.9(4) . . C7 C11 C12 C13 67.8(4) . . C7 C11 C18 C19 -83.8(3) . . C7 C11 C18 C23 95.9(4) . . C8 O1 C9 C10 53.5(4) . . C8 C3 C4 O4 -177.6(3) . 2_755 C8 C3 C4 C5 -1.3(6) . . C8 C7 C11 C12 -126.6(3) . . C8 C7 C11 C18 105.0(4) . . C9 O1 C8 C3 76.5(4) . . C9 O1 C8 C7 -107.7(4) . . C10 O2 C19 C18 96.8(4) . . C10 O2 C19 C20 -87.1(4) . . C11 C7 C8 O1 4.5(5) . . C11 C7 C8 C3 -179.7(3) . . C11 C12 C13 C14 -178.6(3) . . C11 C18 C19 O2 -4.7(4) . . C11 C18 C19 C20 179.3(3) . . C11 C18 C23 C22 179.1(3) . . C12 C11 C18 C19 149.7(3) . . C12 C11 C18 C23 -30.6(4) . . C12 C13 C14 C15 81.4(4) . . C13 C14 C15 C16 -175.7(4) . . C14 C15 C16 C17 -176.4(5) . . C18 C11 C12 C13 -166.7(3) . . C18 C19 C20 C21 1.9(5) . . C18 C19 C20 C24 -177.0(3) . . C19 O2 C10 C9 -135.4(3) . . C19 C18 C23 C22 -1.2(4) . . C19 C20 C21 O3 174.0(3) . . C19 C20 C21 C22 -1.7(5) . . C20 C21 C22 C23 0.1(5) . . C20 C21 C22 C28 178.7(3) . . C21 O3 C26 C27 136.5(3) . . C21 C22 C23 C18 1.4(5) . . C21 C22 C28 C5 83.1(3) . 2_755 C21 C22 C28 C29 -148.8(3) . . C22 C28 C29 C30 161.8(3) . . C23 C18 C19 O2 175.6(3) . . C23 C18 C19 C20 -0.5(5) . . C23 C22 C28 C5 -98.4(4) . 2_755 C23 C22 C28 C29 29.7(4) . . C24 C20 C21 O3 -7.2(5) . . C24 C20 C21 C22 177.1(3) . . C26 O3 C21 C20 89.0(4) . . C26 O3 C21 C22 -95.2(4) . . C28 C5 C6 C7 177.7(3) 2_755 . C28 C22 C23 C18 -177.1(3) . . C28 C29 C30 C31A -175.8(4) . . C29 C30 C31A C32A 167.1(4) . . C30 C31A C32A C33A -177.9(6) . . C31A C32A C33A C34A -179.1(7) . . N3 C45 C46 C47 2(3) . . C45 N3 C49 C48 6.0(15) . . C45 C46 C47 C48 -1(3) . . C46 C47 C48 C49 2.9(17) . . C47 C48 C49 N3 -5.3(16) . . C49 N3 C45 C46 -4.2(18) . . N4 C50 C51 C52 -2.1(10) . . C50 N4 C50 C51 1.1(5) 2_755 . C50 C51 C52 C51 1.0(4) . 2_755 N1 C35 C36 C37 -0.1(8) . . C35 N1 C39 C38 -0.8(6) . . C35 C36 C37 C38 0.5(8) . . C36 C37 C38 C39 -1.1(8) . . C37 C38 C39 N1 1.2(7) . . C39 N1 C35 C36 0.3(7) . . N2 C40 C41 C42 2.3(8) . . C40 N2 C44 C43 -2.4(7) . . C40 C41 C42 C43 -2.5(8) . . C41 C42 C43 C44 0.4(8) . . C42 C43 C44 N2 2.2(8) . . C44 N2 C40 C41 0.2(7) . .