# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Rissanen, Kari' # Name of author for correspondence _publ_contact_author_address ;Department of Chemistry University of Jyvaskyla P.O. Box 35 FIN-40014 Jyvaskyla, Finland ; # Address of author for correspondence _publ_contact_author_email kari.t.rissanen@jyu.fi _publ_contact_author_fax 358(14)2602501 _publ_contact_author_phone 358(50)5623721 _publ_contact_letter ; Submission dated :2011-11-14 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as part of a journal submission Rissanen, Kari ; _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _publ_section_title ; Substituent Effects on Axle Binding in Amide Pseudorotaxanes: Comparison of NMR and ITC Titration Data with Density Functional Calculations Pseudorotaxanes ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' E.V.Dzyuba ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; F.Mahlberg ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; L.Kaufmann ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; N.Low ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; M.Groschke ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; ; B.Brusilowskij ; ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; J.Huuskonen ; ? ; ;Department of Chemistry, Nanoscience Center University of Jyvaskyla P.O. Box 35 FIN-40014 Jyvaskyla, Finland ; K.Rissanen ; ? ; ;Department of Chemistry, Nanoscience Center University of Jyvaskyla P.O. Box 35 FIN-40014 Jyvaskyla, Finland ; B.Kirscher ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; C.A.Schalley ; ? ; ;Institut fur Chemie und Biochemie Freie Universitat Berlin Takustrasse 5 14195 Berlin, Germany ; data_2@1b _database_code_depnum_ccdc_archive 'CCDC 853879' _audit_creation_date 2011-11-02T13:20:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_formula_sum 'C82 H100 Cl12 N6 O6' _chemical_formula_moiety 'C68 H80 N4 O4, C10 H16 N2 O2, 4(C H Cl3)' _chemical_formula_weight 1691.08 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.087(3) _cell_length_b 13.192(2) _cell_length_c 14.620(3) _cell_angle_alpha 103.23(2) _cell_angle_beta 107.21(3) _cell_angle_gamma 108.81(2) _cell_volume 2130.5(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6843 _cell_measurement_theta_min 5.8 _cell_measurement_theta_max 63.31 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 886 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.42 _exptl_absorpt_correction_T_max 0.59 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.0143722 _diffrn_orient_matrix_ub_12 -0.0420361 _diffrn_orient_matrix_ub_13 0.0478804 _diffrn_orient_matrix_ub_21 0.0851353 _diffrn_orient_matrix_ub_22 0.0301667 _diffrn_orient_matrix_ub_23 0.011579 _diffrn_orient_matrix_ub_31 0.0176486 _diffrn_orient_matrix_ub_32 0.0684226 _diffrn_orient_matrix_ub_33 0.0587955 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_unetI/netI 0.0724 _diffrn_reflns_number 9544 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.8 _diffrn_reflns_theta_max 63.31 _diffrn_reflns_theta_full 63.31 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 6843 _reflns_number_gt 5265 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1038P)^2^+3.5602P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6843 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0956 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.216 _refine_ls_wR_factor_gt 0.1974 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.692 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.08 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1817(3) 0.2204(3) 0.3330(3) 0.0279(8) Uani 1 1 d . . . H14 H 1.1469 0.2662 0.36 0.033 Uiso 1 1 calc R . . C2 C 1.1347(3) 0.1587(3) 0.2281(3) 0.0264(8) Uani 1 1 d . . . C3 C 1.1869(3) 0.0921(3) 0.1897(3) 0.0275(8) Uani 1 1 d . . . H25 H 1.1537 0.0491 0.1183 0.033 Uiso 1 1 calc R . . C4 C 1.2858(3) 0.0868(3) 0.2528(3) 0.0274(8) Uani 1 1 d . . . C5 C 1.3312(3) 0.1487(3) 0.3582(3) 0.0275(8) Uani 1 1 d . . . H12 H 1.3982 0.1454 0.4034 0.033 Uiso 1 1 calc R . . C6 C 1.2794(3) 0.2147(3) 0.3975(3) 0.0265(8) Uani 1 1 d . . . C7 C 1.0269(3) 0.1616(3) 0.1558(3) 0.0285(8) Uani 1 1 d . . . C8 C 1.3291(3) 0.2757(3) 0.5114(3) 0.0288(8) Uani 1 1 d . . . C9 C 1.3452(4) 0.0164(4) 0.2085(3) 0.0319(9) Uani 1 1 d . . . C10 C 1.4496(5) 0.0177(5) 0.2904(4) 0.0580(14) Uani 1 1 d . . . H41 H 1.4236 -0.013 0.3386 0.087 Uiso 1 1 calc R . . H42 H 1.5101 0.0966 0.3274 0.087 Uiso 1 1 calc R . . H43 H 1.4824 -0.0299 0.258 0.087 Uiso 1 1 calc R . . C11 C 1.3869(5) 0.0640(5) 0.1340(4) 0.0538(13) Uani 1 1 d . . . H44 H 1.3202 0.0636 0.0809 0.081 Uiso 1 1 calc R . . H45 H 1.4198 0.0163 0.102 0.081 Uiso 1 1 calc R . . H46 H 1.4476 0.1428 0.1713 0.081 Uiso 1 1 calc R . . C12 C 1.2549(4) -0.1094(4) 0.1513(4) 0.0503(12) Uani 1 1 d . . . H47 H 1.2278 -0.1397 0.1993 0.075 Uiso 1 1 calc R . . H48 H 1.2918 -0.1548 0.1225 0.075 Uiso 1 1 calc R . . H49 H 1.1875 -0.1139 0.0958 0.075 Uiso 1 1 calc R . . C21 C 0.9097(3) 0.2782(3) 0.1432(3) 0.0293(9) Uani 1 1 d . . . C22 C 0.7986(3) 0.2092(3) 0.1333(3) 0.0291(8) Uani 1 1 d . . . C23 C 0.7060(3) 0.2403(3) 0.0981(3) 0.0293(8) Uani 1 1 d . . . H27 H 0.6296 0.1927 0.0904 0.035 Uiso 1 1 calc R . . C24 C 0.7225(3) 0.3400(3) 0.0738(3) 0.0261(8) Uani 1 1 d . . . C25 C 0.8340(3) 0.4038(3) 0.0819(3) 0.0287(8) Uani 1 1 d . . . H28 H 0.8462 0.4693 0.0623 0.034 Uiso 1 1 calc R . . C26 C 0.9293(3) 0.3769(4) 0.1173(3) 0.0310(9) Uani 1 1 d . . . C27 C 0.6230(3) 0.3810(3) 0.0498(3) 0.0282(8) Uani 1 1 d . . . C28 C 0.5004(3) 0.2794(4) -0.0132(3) 0.0318(9) Uani 1 1 d . . . H131 H 0.4885 0.2251 0.0236 0.038 Uiso 1 1 calc R . . H132 H 0.4388 0.3086 -0.0191 0.038 Uiso 1 1 calc R . . C29 C 0.4867(4) 0.2158(4) -0.1205(3) 0.0391(10) Uani 1 1 d . . . H50 H 0.5448 0.1822 -0.1148 0.047 Uiso 1 1 calc R . . H51 H 0.4069 0.1523 -0.158 0.047 Uiso 1 1 calc R . . C30 C 0.5050(4) 0.2953(5) -0.1807(3) 0.0480(12) Uani 1 1 d . . . H52 H 0.4411 0.3218 -0.1939 0.058 Uiso 1 1 calc R . . H53 H 0.5014 0.2529 -0.2477 0.058 Uiso 1 1 calc R . . C31 C 0.6238(4) 0.3987(4) -0.1213(3) 0.0416(11) Uani 1 1 d . . . H311 H 0.6307 0.4531 -0.1583 0.05 Uiso 1 1 calc R . . H312 H 0.6878 0.3731 -0.1172 0.05 Uiso 1 1 calc R . . C32 C 0.6379(4) 0.4598(4) -0.0127(3) 0.0322(9) Uani 1 1 d . . . H56 H 0.5789 0.4922 -0.0175 0.039 Uiso 1 1 calc R . . H57 H 0.7171 0.5244 0.0243 0.039 Uiso 1 1 calc R . . C33 C 0.7757(4) 0.1044(4) 0.1632(3) 0.0401(10) Uani 1 1 d . . . H58 H 0.6924 0.0683 0.1512 0.06 Uiso 1 1 calc R . . H59 H 0.8247 0.1271 0.236 0.06 Uiso 1 1 calc R . . H60 H 0.7953 0.0498 0.1219 0.06 Uiso 1 1 calc R . . C34 C 1.0498(4) 0.4541(4) 0.1306(4) 0.0425(10) Uani 1 1 d . . . H61 H 1.1059 0.4226 0.1564 0.064 Uiso 1 1 calc R . . H62 H 1.0743 0.5306 0.1797 0.064 Uiso 1 1 calc R . . H63 H 1.0477 0.4595 0.0644 0.064 Uiso 1 1 calc R . . C41 C 1.3381(4) 0.4332(3) 0.6468(3) 0.0308(9) Uani 1 1 d . . . C42 C 1.4389(3) 0.5326(3) 0.7074(3) 0.0299(9) Uani 1 1 d . . . C43 C 1.4521(3) 0.5905(3) 0.8057(3) 0.0277(8) Uani 1 1 d . . . H64 H 1.5212 0.659 0.8478 0.033 Uiso 1 1 calc R . . C44 C 1.3682(3) 0.5520(3) 0.8447(3) 0.0278(8) Uani 1 1 d . . . C45 C 1.2690(3) 0.4505(3) 0.7813(3) 0.0315(9) Uani 1 1 d . . . H65 H 1.2103 0.4219 0.8061 0.038 Uiso 1 1 calc R . . C46 C 1.2526(3) 0.3894(3) 0.6833(3) 0.0305(9) Uani 1 1 d . . . C47 C 1.5330(4) 0.5777(4) 0.6698(3) 0.0436(11) Uani 1 1 d . . . H66 H 1.5972 0.6485 0.7233 0.065 Uiso 1 1 calc R . . H67 H 1.4997 0.5937 0.6082 0.065 Uiso 1 1 calc R . . H68 H 1.5637 0.5203 0.6534 0.065 Uiso 1 1 calc R . . C48 C 1.1442(4) 0.2782(4) 0.6196(3) 0.0431(10) Uani 1 1 d . . . H69 H 1.1457 0.2463 0.5527 0.065 Uiso 1 1 calc R . . H70 H 1.0735 0.2926 0.6096 0.065 Uiso 1 1 calc R . . H71 H 1.1431 0.2234 0.6551 0.065 Uiso 1 1 calc R . . C49 C 0.7806(6) 0.0206(5) 0.4974(4) 0.0624(14) Uani 1 1 d . . . H72 H 0.7133 -0.0545 0.478 0.075 Uiso 1 1 calc R . . C50 C 1.1042(4) 0.1794(4) 0.9135(4) 0.0507(12) Uani 1 1 d . . . H73 H 1.0468 0.1082 0.9142 0.061 Uiso 1 1 calc R . . C51 C 1.0510(6) 0.4875(5) 0.5266(4) 0.0621(15) Uani 1 1 d . . . H74 H 1.0542 0.4888 0.5954 0.074 Uiso 1 1 calc R . . H75 H 1.0387 0.4098 0.4867 0.074 Uiso 1 1 calc R . . C53 C 1.2023(5) 0.5498(4) 0.4640(4) 0.0487(12) Uani 1 1 d . . . C54 C 1.3125(5) 0.6369(5) 0.4723(4) 0.0620(15) Uani 1 1 d . . . H54 H 1.362 0.6983 0.536 0.074 Uiso 1 1 calc R . . C55 C 1.3447(5) 0.6326(6) 0.3952(5) 0.0760(18) Uani 1 1 d . . . H76 H 1.2965 0.5718 0.331 0.091 Uiso 1 1 calc R . . H77 H 1.4164 0.6903 0.4037 0.091 Uiso 1 1 calc R . . C57 C 1.2230(7) 0.6766(6) 0.6285(5) 0.084(2) Uani 1 1 d . . . H78 H 1.1766 0.6729 0.6704 0.127 Uiso 1 1 calc R . . H79 H 1.2313 0.7435 0.608 0.127 Uiso 1 1 calc R . . H80 H 1.3012 0.6834 0.6685 0.127 Uiso 1 1 calc R . . N1 N 1.0105(3) 0.2582(3) 0.1905(3) 0.0326(8) Uani 1 1 d . . . N2 N 1.3178(3) 0.3747(3) 0.5427(2) 0.0320(8) Uani 1 1 d . . . N52 N 1.1632(4) 0.5724(4) 0.5372(3) 0.0550(11) Uani 1 1 d . . . O1 O 0.9606(3) 0.0836(3) 0.0744(2) 0.0388(7) Uani 1 1 d . . . O2 O 1.3747(3) 0.2364(3) 0.5714(2) 0.0396(7) Uani 1 1 d . . . O56 O 1.1484(3) 0.4582(3) 0.3897(3) 0.0577(9) Uani 1 1 d . . . Cl1 Cl 0.8032(2) 0.03319(17) 0.38757(13) 0.0984(6) Uani 1 1 d . . . Cl2 Cl 0.90903(14) 0.02529(15) 0.58593(13) 0.0820(5) Uani 1 1 d . . . Cl3 Cl 0.7484(2) 0.13087(19) 0.55250(17) 0.1117(8) Uani 1 1 d . . . Cl4 Cl 1.16430(15) 0.14215(14) 0.82523(11) 0.0729(5) Uani 1 1 d . . . Cl5 Cl 1.03129(12) 0.26395(13) 0.87640(12) 0.0680(4) Uani 1 1 d . . . Cl6 Cl 1.21786(11) 0.25851(12) 1.03702(10) 0.0580(4) Uani 1 1 d . . . H811 H 1.072(4) 0.315(5) 0.242(4) 0.05 Uiso 1 1 d . . . H812 H 1.296(4) 0.406(4) 0.497(4) 0.046(13) Uiso 1 1 d . . . 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 C1 0.038(2) 0.028(2) 0.0257(19) 0.0097(16) 0.0143(16) 0.0215(18) C2 0.033(2) 0.027(2) 0.0273(19) 0.0112(16) 0.0136(16) 0.0197(17) C3 0.035(2) 0.025(2) 0.0231(18) 0.0054(16) 0.0122(16) 0.0149(17) C4 0.037(2) 0.024(2) 0.028(2) 0.0100(16) 0.0169(17) 0.0175(17) C5 0.0303(19) 0.028(2) 0.029(2) 0.0126(17) 0.0104(16) 0.0184(17) C6 0.035(2) 0.027(2) 0.0237(19) 0.0088(16) 0.0141(16) 0.0178(17) C7 0.039(2) 0.031(2) 0.0212(19) 0.0079(18) 0.0124(17) 0.0231(19) C8 0.035(2) 0.030(2) 0.026(2) 0.0098(17) 0.0132(17) 0.0192(18) C9 0.039(2) 0.035(2) 0.028(2) 0.0065(17) 0.0153(17) 0.0255(19) C10 0.059(3) 0.069(4) 0.049(3) 0.006(3) 0.016(2) 0.047(3) C11 0.070(3) 0.058(3) 0.063(3) 0.026(3) 0.047(3) 0.040(3) C12 0.050(3) 0.038(3) 0.060(3) 0.003(2) 0.023(2) 0.024(2) C21 0.041(2) 0.030(2) 0.0222(18) 0.0075(16) 0.0106(16) 0.0245(19) C22 0.042(2) 0.029(2) 0.0250(19) 0.0085(16) 0.0156(17) 0.0239(19) C23 0.037(2) 0.033(2) 0.0258(19) 0.0118(17) 0.0139(16) 0.0213(18) C24 0.040(2) 0.029(2) 0.0191(17) 0.0083(16) 0.0138(16) 0.0236(18) C25 0.044(2) 0.026(2) 0.029(2) 0.0128(17) 0.0175(17) 0.0244(18) C26 0.037(2) 0.033(2) 0.028(2) 0.0078(17) 0.0147(17) 0.0212(19) C27 0.040(2) 0.032(2) 0.0247(19) 0.0111(17) 0.0157(17) 0.0261(19) C28 0.037(2) 0.036(2) 0.028(2) 0.0077(17) 0.0123(17) 0.0256(19) C29 0.042(2) 0.046(3) 0.029(2) 0.0024(19) 0.0106(18) 0.028(2) C30 0.062(3) 0.070(4) 0.023(2) 0.013(2) 0.016(2) 0.046(3) C31 0.058(3) 0.058(3) 0.030(2) 0.024(2) 0.022(2) 0.041(3) C32 0.042(2) 0.039(2) 0.035(2) 0.0201(19) 0.0197(18) 0.032(2) C33 0.052(3) 0.038(3) 0.046(3) 0.024(2) 0.023(2) 0.030(2) C34 0.041(2) 0.044(3) 0.054(3) 0.024(2) 0.023(2) 0.025(2) C41 0.044(2) 0.033(2) 0.0244(19) 0.0105(17) 0.0145(17) 0.026(2) C42 0.039(2) 0.031(2) 0.0269(19) 0.0114(17) 0.0154(17) 0.0211(19) C43 0.0314(19) 0.023(2) 0.0283(19) 0.0058(16) 0.0101(16) 0.0157(17) C44 0.038(2) 0.029(2) 0.0247(19) 0.0090(16) 0.0112(16) 0.0244(18) C45 0.036(2) 0.030(2) 0.033(2) 0.0102(18) 0.0181(18) 0.0161(18) C46 0.039(2) 0.026(2) 0.031(2) 0.0080(17) 0.0143(17) 0.0184(18) C47 0.055(3) 0.042(3) 0.037(2) 0.011(2) 0.026(2) 0.019(2) C48 0.048(3) 0.033(2) 0.036(2) 0.0031(19) 0.013(2) 0.011(2) C49 0.088(4) 0.047(3) 0.060(3) 0.025(3) 0.034(3) 0.032(3) C50 0.048(3) 0.042(3) 0.068(3) 0.026(3) 0.026(2) 0.020(2) C51 0.099(4) 0.065(4) 0.051(3) 0.029(3) 0.038(3) 0.056(4) C53 0.070(3) 0.043(3) 0.041(3) 0.013(2) 0.014(2) 0.041(3) C54 0.057(3) 0.051(3) 0.060(3) 0.000(3) 0.008(3) 0.028(3) C55 0.054(3) 0.085(5) 0.084(4) 0.018(4) 0.022(3) 0.036(3) C57 0.121(6) 0.073(5) 0.054(4) 0.002(3) 0.029(4) 0.054(4) N1 0.0404(19) 0.033(2) 0.0286(17) 0.0070(15) 0.0092(15) 0.0267(17) N2 0.053(2) 0.0292(19) 0.0212(16) 0.0093(15) 0.0143(15) 0.0266(17) N52 0.083(3) 0.050(3) 0.040(2) 0.014(2) 0.023(2) 0.042(3) O1 0.0445(16) 0.0391(17) 0.0281(15) 0.0008(13) 0.0053(13) 0.0282(14) O2 0.0574(18) 0.0409(18) 0.0264(14) 0.0107(13) 0.0116(13) 0.0334(16) O56 0.078(2) 0.043(2) 0.0446(19) 0.0034(17) 0.0167(17) 0.0327(19) Cl1 0.1699(19) 0.0942(14) 0.0704(10) 0.0459(10) 0.0684(12) 0.0726(14) Cl2 0.0700(9) 0.0693(10) 0.0892(11) 0.0428(9) 0.0166(8) 0.0125(8) Cl3 0.191(2) 0.0968(15) 0.1143(15) 0.0522(13) 0.0945(16) 0.1001(17) Cl4 0.1058(12) 0.0772(11) 0.0645(9) 0.0294(8) 0.0389(8) 0.0656(10) Cl5 0.0533(7) 0.0678(9) 0.0871(10) 0.0269(8) 0.0209(7) 0.0376(7) Cl6 0.0610(8) 0.0659(9) 0.0544(7) 0.0319(7) 0.0246(6) 0.0268(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 C6 1.383(5) . ? C1 C2 1.393(5) . ? C1 H14 0.95 . ? C2 C3 1.394(5) . ? C2 C7 1.510(5) . ? C3 C4 1.381(5) . ? C3 H25 0.95 . ? C4 C5 1.402(5) . ? C4 C9 1.541(5) . ? C5 C6 1.389(5) . ? C5 H12 0.95 . ? C6 C8 1.500(5) . ? C7 O1 1.217(5) . ? C7 N1 1.368(5) . ? C8 O2 1.222(4) . ? C8 N2 1.352(5) . ? C9 C10 1.520(6) . ? C9 C11 1.523(6) . ? C9 C12 1.538(6) . ? C10 H41 0.98 . ? C10 H42 0.98 . ? C10 H43 0.98 . ? C11 H44 0.98 . ? C11 H45 0.98 . ? C11 H46 0.98 . ? C12 H47 0.98 . ? C12 H48 0.98 . ? C12 H49 0.98 . ? C21 C22 1.387(6) . ? C21 C26 1.405(6) . ? C21 N1 1.434(5) . ? C22 C23 1.397(5) . ? C22 C33 1.509(5) . ? C23 C24 1.407(5) . ? C23 H27 0.95 . ? C24 C25 1.383(6) . ? C24 C27 1.543(5) . ? C25 C26 1.392(5) . ? C25 H28 0.95 . ? C26 C34 1.501(6) . ? C27 C32 1.537(5) . ? C27 C44 1.542(5) 2_766 ? C27 C28 1.547(6) . ? C28 C29 1.528(5) . ? C28 H131 0.99 . ? C28 H132 0.99 . ? C29 C30 1.522(7) . ? C29 H50 0.99 . ? C29 H51 0.99 . ? C30 C31 1.525(7) . ? C30 H52 0.99 . ? C30 H53 0.99 . ? C31 C32 1.534(6) . ? C31 H311 0.99 . ? C31 H312 0.99 . ? C32 H56 0.99 . ? C32 H57 0.99 . ? C33 H58 0.98 . ? C33 H59 0.98 . ? C33 H60 0.98 . ? C34 H61 0.98 . ? C34 H62 0.98 . ? C34 H63 0.98 . ? C41 C42 1.380(6) . ? C41 C46 1.397(6) . ? C41 N2 1.439(5) . ? C42 C43 1.395(5) . ? C42 C47 1.501(6) . ? C43 C44 1.389(5) . ? C43 H64 0.95 . ? C44 C45 1.392(6) . ? C44 C27 1.542(5) 2_766 ? C45 C46 1.389(5) . ? C45 H65 0.95 . ? C46 C48 1.511(6) . ? C47 H66 0.98 . ? C47 H67 0.98 . ? C47 H68 0.98 . ? C48 H69 0.98 . ? C48 H70 0.98 . ? C48 H71 0.98 . ? C49 Cl3 1.732(6) . ? C49 Cl1 1.751(6) . ? C49 Cl2 1.764(6) . ? C49 H72 1 . ? C50 Cl4 1.756(5) . ? C50 Cl5 1.762(5) . ? C50 Cl6 1.764(5) . ? C50 H73 1 . ? C51 N52 1.470(8) . ? C51 C51 1.511(10) 2_766 ? C51 H74 0.99 . ? C51 H75 0.99 . ? C53 O56 1.238(6) . ? C53 N52 1.332(6) . ? C53 C54 1.475(8) . ? C54 C55 1.311(8) . ? C54 H54 0.95 . ? C55 H76 0.95 . ? C55 H77 0.95 . ? C57 N52 1.461(7) . ? C57 H78 0.98 . ? C57 H79 0.98 . ? C57 H80 0.98 . ? N1 H811 0.88(5) . ? N2 H812 0.88(5) . ? 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 C6 C1 C2 119.6(3) . . ? C6 C1 H14 120.2 . . ? C2 C1 H14 120.2 . . ? C1 C2 C3 119.4(3) . . ? C1 C2 C7 120.9(3) . . ? C3 C2 C7 119.7(3) . . ? C4 C3 C2 121.8(3) . . ? C4 C3 H25 119.1 . . ? C2 C3 H25 119.1 . . ? C3 C4 C5 117.9(3) . . ? C3 C4 C9 121.1(3) . . ? C5 C4 C9 121.0(3) . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H12 119.6 . . ? C4 C5 H12 119.6 . . ? C1 C6 C5 120.4(3) . . ? C1 C6 C8 121.0(3) . . ? C5 C6 C8 118.6(3) . . ? O1 C7 N1 123.6(3) . . ? O1 C7 C2 122.2(3) . . ? N1 C7 C2 114.2(3) . . ? O2 C8 N2 122.6(3) . . ? O2 C8 C6 121.5(3) . . ? N2 C8 C6 115.9(3) . . ? C10 C9 C11 108.9(4) . . ? C10 C9 C12 107.2(4) . . ? C11 C9 C12 109.6(4) . . ? C10 C9 C4 113.1(3) . . ? C11 C9 C4 109.1(3) . . ? C12 C9 C4 108.9(3) . . ? C9 C10 H41 109.5 . . ? C9 C10 H42 109.5 . . ? H41 C10 H42 109.5 . . ? C9 C10 H43 109.5 . . ? H41 C10 H43 109.5 . . ? H42 C10 H43 109.5 . . ? C9 C11 H44 109.5 . . ? C9 C11 H45 109.5 . . ? H44 C11 H45 109.5 . . ? C9 C11 H46 109.5 . . ? H44 C11 H46 109.5 . . ? H45 C11 H46 109.5 . . ? C9 C12 H47 109.5 . . ? C9 C12 H48 109.5 . . ? H47 C12 H48 109.5 . . ? C9 C12 H49 109.5 . . ? H47 C12 H49 109.5 . . ? H48 C12 H49 109.5 . . ? C22 C21 C26 121.1(3) . . ? C22 C21 N1 121.1(3) . . ? C26 C21 N1 117.5(4) . . ? C21 C22 C23 118.8(4) . . ? C21 C22 C33 122.2(3) . . ? C23 C22 C33 119.0(4) . . ? C22 C23 C24 121.9(4) . . ? C22 C23 H27 119 . . ? C24 C23 H27 119 . . ? C25 C24 C23 117.0(3) . . ? C25 C24 C27 122.2(3) . . ? C23 C24 C27 120.5(3) . . ? C24 C25 C26 123.1(4) . . ? C24 C25 H28 118.4 . . ? C26 C25 H28 118.4 . . ? C25 C26 C21 118.0(4) . . ? C25 C26 C34 120.4(4) . . ? C21 C26 C34 121.6(3) . . ? C32 C27 C44 109.8(3) . 2_766 ? C32 C27 C24 112.2(3) . . ? C44 C27 C24 105.2(3) 2_766 . ? C32 C27 C28 106.7(3) . . ? C44 C27 C28 111.1(3) 2_766 . ? C24 C27 C28 111.9(3) . . ? C29 C28 C27 112.2(3) . . ? C29 C28 H131 109.2 . . ? C27 C28 H131 109.2 . . ? C29 C28 H132 109.2 . . ? C27 C28 H132 109.2 . . ? H131 C28 H132 107.9 . . ? C30 C29 C28 111.6(4) . . ? C30 C29 H50 109.3 . . ? C28 C29 H50 109.3 . . ? C30 C29 H51 109.3 . . ? C28 C29 H51 109.3 . . ? H50 C29 H51 108 . . ? C29 C30 C31 110.6(3) . . ? C29 C30 H52 109.5 . . ? C31 C30 H52 109.5 . . ? C29 C30 H53 109.5 . . ? C31 C30 H53 109.5 . . ? H52 C30 H53 108.1 . . ? C30 C31 C32 111.2(4) . . ? C30 C31 H311 109.4 . . ? C32 C31 H311 109.4 . . ? C30 C31 H312 109.4 . . ? C32 C31 H312 109.4 . . ? H311 C31 H312 108 . . ? C31 C32 C27 113.5(3) . . ? C31 C32 H56 108.9 . . ? C27 C32 H56 108.9 . . ? C31 C32 H57 108.9 . . ? C27 C32 H57 108.9 . . ? H56 C32 H57 107.7 . . ? C22 C33 H58 109.5 . . ? C22 C33 H59 109.5 . . ? H58 C33 H59 109.5 . . ? C22 C33 H60 109.5 . . ? H58 C33 H60 109.5 . . ? H59 C33 H60 109.5 . . ? C26 C34 H61 109.5 . . ? C26 C34 H62 109.5 . . ? H61 C34 H62 109.5 . . ? C26 C34 H63 109.5 . . ? H61 C34 H63 109.5 . . ? H62 C34 H63 109.5 . . ? C42 C41 C46 121.2(3) . . ? C42 C41 N2 120.1(4) . . ? C46 C41 N2 118.7(4) . . ? C41 C42 C43 118.3(4) . . ? C41 C42 C47 121.4(3) . . ? C43 C42 C47 120.3(4) . . ? C44 C43 C42 122.7(4) . . ? C44 C43 H64 118.7 . . ? C42 C43 H64 118.7 . . ? C43 C44 C45 116.9(3) . . ? C43 C44 C27 123.5(4) . 2_766 ? C45 C44 C27 119.5(3) . 2_766 ? C46 C45 C44 122.4(4) . . ? C46 C45 H65 118.8 . . ? C44 C45 H65 118.8 . . ? C45 C46 C41 118.4(4) . . ? C45 C46 C48 119.7(4) . . ? C41 C46 C48 121.9(4) . . ? C42 C47 H66 109.5 . . ? C42 C47 H67 109.5 . . ? H66 C47 H67 109.5 . . ? C42 C47 H68 109.5 . . ? H66 C47 H68 109.5 . . ? H67 C47 H68 109.5 . . ? C46 C48 H69 109.5 . . ? C46 C48 H70 109.5 . . ? H69 C48 H70 109.5 . . ? C46 C48 H71 109.5 . . ? H69 C48 H71 109.5 . . ? H70 C48 H71 109.5 . . ? Cl3 C49 Cl1 110.4(3) . . ? Cl3 C49 Cl2 109.8(3) . . ? Cl1 C49 Cl2 109.1(3) . . ? Cl3 C49 H72 109.2 . . ? Cl1 C49 H72 109.2 . . ? Cl2 C49 H72 109.2 . . ? Cl4 C50 Cl5 108.9(3) . . ? Cl4 C50 Cl6 109.7(3) . . ? Cl5 C50 Cl6 109.4(3) . . ? Cl4 C50 H73 109.6 . . ? Cl5 C50 H73 109.6 . . ? Cl6 C50 H73 109.6 . . ? N52 C51 C51 111.0(6) . 2_766 ? N52 C51 H74 109.4 . . ? C51 C51 H74 109.4 2_766 . ? N52 C51 H75 109.4 . . ? C51 C51 H75 109.4 2_766 . ? H74 C51 H75 108 . . ? O56 C53 N52 121.6(5) . . ? O56 C53 C54 119.8(5) . . ? N52 C53 C54 118.6(5) . . ? C55 C54 C53 122.5(5) . . ? C55 C54 H54 118.8 . . ? C53 C54 H54 118.8 . . ? C54 C55 H76 120 . . ? C54 C55 H77 120 . . ? H76 C55 H77 120 . . ? N52 C57 H78 109.5 . . ? N52 C57 H79 109.5 . . ? H78 C57 H79 109.5 . . ? N52 C57 H80 109.5 . . ? H78 C57 H80 109.5 . . ? H79 C57 H80 109.5 . . ? C7 N1 C21 126.0(3) . . ? C7 N1 H811 115(3) . . ? C21 N1 H811 118(3) . . ? C8 N2 C41 123.9(3) . . ? C8 N2 H812 119(3) . . ? C41 N2 H812 117(3) . . ? C53 N52 C57 125.1(6) . . ? C53 N52 C51 118.6(5) . . ? C57 N52 C51 116.4(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H811 O56 0.88(5) 2.20(5) 3.000(5) 151(4) . N2 H812 O56 0.88(5) 2.50(5) 3.301(5) 152(4) . data_8@1b _database_code_depnum_ccdc_archive 'CCDC 853880' _audit_creation_date 2011-11-03T08:35:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C68 H80 N4 O4, C18 H20 N2 O2, 2(C H Cl3)' _chemical_formula_sum 'C88 H102 Cl6 N6 O6' _chemical_formula_weight 1552.46 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 25.976(5) _cell_length_b 19.610(4) _cell_length_c 19.930(4) _cell_angle_alpha 90 _cell_angle_beta 126.21(3) _cell_angle_gamma 90 _cell_volume 8191(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 20775 _cell_measurement_theta_min 3.94 _cell_measurement_theta_max 27.45 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3288 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.004048 _diffrn_orient_matrix_ub_12 -0.0577389 _diffrn_orient_matrix_ub_13 0.0072101 _diffrn_orient_matrix_ub_21 -0.0633976 _diffrn_orient_matrix_ub_22 -0.0170981 _diffrn_orient_matrix_ub_23 0.0008935 _diffrn_orient_matrix_ub_31 -0.034676 _diffrn_orient_matrix_ub_32 -0.0353644 _diffrn_orient_matrix_ub_33 -0.0617634 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.1122 _diffrn_reflns_av_unetI/netI 0.0712 _diffrn_reflns_number 54437 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 7156 _reflns_number_gt 4611 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+16.6562P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7156 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1742 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.38 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl3 Cl -0.41535(6) 0.71322(6) -0.37971(7) 0.0667(4) Uani 1 1 d . . . Cl1 Cl -0.38872(6) 0.59502(6) -0.27901(8) 0.0688(4) Uani 1 1 d . . . Cl2 Cl -0.43767(8) 0.71767(12) -0.25496(10) 0.1190(7) Uani 1 1 d . . . O2 O -0.26662(12) 0.68061(12) -0.09818(17) 0.0417(6) Uani 1 1 d . . . O48 O -0.14715(14) 0.46694(14) -0.09792(18) 0.0524(7) Uani 1 1 d . . . O1 O -0.19597(13) 0.36018(14) 0.09567(18) 0.0520(7) Uani 1 1 d . . . N8 N -0.20335(14) 0.60722(15) -0.10689(19) 0.0372(7) Uani 1 1 d . . . H8 H -0.1937 0.5639 -0.1049 0.045 Uiso 1 1 calc R . . C11 C -0.15040(16) 0.69354(17) -0.2212(2) 0.0337(8) Uani 1 1 d . . . H11 H -0.158 0.6909 -0.2739 0.04 Uiso 1 1 calc R . . C5 C -0.33660(16) 0.51728(17) -0.0325(2) 0.0309(8) Uani 1 1 d . . . N22 N -0.16944(14) 0.37579(15) 0.00716(19) 0.0368(7) Uani 1 1 d . . . H22 H -0.1837 0.3913 -0.0424 0.044 Uiso 1 1 calc R . . C14 C -0.13051(16) 0.70284(17) -0.0677(2) 0.0329(8) Uani 1 1 d . . . C6 C -0.29773(17) 0.46060(18) 0.0004(2) 0.0340(8) Uani 1 1 d . . . H6 H -0.3081 0.425 0.0228 0.041 Uiso 1 1 calc R . . C17 C -0.05884(16) 0.22974(17) 0.0690(2) 0.0338(8) Uani 1 1 d . . . H17 H -0.0601 0.1838 0.0529 0.041 Uiso 1 1 calc R . . C10 C -0.18410(16) 0.65017(17) -0.2039(2) 0.0341(8) Uani 1 1 d . . . C19 C -0.11323(17) 0.33388(18) 0.0513(2) 0.0358(8) Uani 1 1 d . . . C34 C 0.09132(17) 0.21136(18) 0.2706(2) 0.0351(8) Uani 1 1 d . . . H34A H 0.1008 0.2575 0.2955 0.042 Uiso 1 1 calc R . . H34B H 0.0589 0.1905 0.2755 0.042 Uiso 1 1 calc R . . C4 C -0.31840(16) 0.57000(17) -0.0624(2) 0.0329(8) Uani 1 1 d . . . H4 H -0.3439 0.61 -0.0848 0.039 Uiso 1 1 calc R . . C38 C -0.15647(17) 0.40546(18) -0.2070(2) 0.0390(9) Uani 1 1 d . . . C13 C -0.09762(16) 0.74439(17) -0.0870(2) 0.0321(8) Uani 1 1 d . . . H13 H -0.0682 0.7768 -0.0471 0.039 Uiso 1 1 calc R . . C16 C -0.00047(16) 0.25762(17) 0.1327(2) 0.0310(8) Uani 1 1 d . . . C30 C 0.05309(16) 0.14463(16) 0.1433(2) 0.0322(8) Uani 1 1 d . . . H30A H 0.0209 0.1213 0.1466 0.039 Uiso 1 1 calc R . . H30B H 0.0362 0.1469 0.084 0.039 Uiso 1 1 calc R . . C26 C -0.4101(2) 0.59578(19) -0.0236(3) 0.0472(10) Uani 1 1 d . . . H26A H -0.3758 0.6083 0.0338 0.071 Uiso 1 1 calc R . . H26B H -0.4511 0.5978 -0.0318 0.071 Uiso 1 1 calc R . . H26C H -0.4106 0.6276 -0.0619 0.071 Uiso 1 1 calc R . . C9 C -0.17311(16) 0.65509(17) -0.1270(2) 0.0320(8) Uani 1 1 d . . . C12 C -0.10611(16) 0.74036(16) -0.1629(2) 0.0309(8) Uani 1 1 d . . . N45 N -0.05472(15) 0.43371(17) -0.0766(2) 0.0464(8) Uani 1 1 d . . . C31 C 0.11448(18) 0.10300(18) 0.1907(2) 0.0384(8) Uani 1 1 d . . . H31A H 0.1459 0.1246 0.1845 0.046 Uiso 1 1 calc R . . H31B H 0.1055 0.0566 0.1667 0.046 Uiso 1 1 calc R . . C18 C -0.11577(17) 0.26703(18) 0.0277(2) 0.0359(8) Uani 1 1 d . . . C20 C -0.05623(18) 0.36351(18) 0.1160(2) 0.0368(8) Uani 1 1 d . . . C36 C -0.05498(19) 0.4358(2) 0.1424(3) 0.0469(10) Uani 1 1 d . . . H36A H -0.0831 0.4641 0.093 0.07 Uiso 1 1 calc R . . H36B H -0.0113 0.4535 0.1736 0.07 Uiso 1 1 calc R . . H36C H -0.0697 0.4369 0.1777 0.07 Uiso 1 1 calc R . . C15 C 0.06301(16) 0.21818(17) 0.1777(2) 0.0319(8) Uani 1 1 d . . . C3 C -0.26391(16) 0.56479(17) -0.0599(2) 0.0324(8) Uani 1 1 d . . . C35 C -0.17783(18) 0.2350(2) -0.0395(3) 0.0469(10) Uani 1 1 d . . . H35A H -0.1705 0.1877 -0.0476 0.07 Uiso 1 1 calc R . . H35B H -0.1967 0.2604 -0.0914 0.07 Uiso 1 1 calc R . . H35C H -0.207 0.2359 -0.0236 0.07 Uiso 1 1 calc R . . C1 C -0.24368(16) 0.45401(17) 0.0019(2) 0.0328(8) Uani 1 1 d . . . C44 C -0.11904(19) 0.43755(18) -0.1231(2) 0.0399(9) Uani 1 1 d . . . C28 C -0.11964(18) 0.70964(19) 0.0150(2) 0.0397(9) Uani 1 1 d . . . H28A H -0.0883 0.7457 0.0476 0.06 Uiso 1 1 calc R . . H28B H -0.1036 0.6664 0.0453 0.06 Uiso 1 1 calc R . . H28C H -0.16 0.7213 0.0061 0.06 Uiso 1 1 calc R . . C7 C -0.24562(16) 0.62300(18) -0.0906(2) 0.0335(8) Uani 1 1 d . . . C47 C -0.0166(2) 0.4703(2) 0.0022(3) 0.0576(11) Uani 1 1 d . . . H47A H 0.0155 0.4388 0.0463 0.069 Uiso 1 1 calc R . . H47B H -0.0446 0.4861 0.0175 0.069 Uiso 1 1 calc R . . C32 C 0.14279(19) 0.09802(19) 0.2828(2) 0.0432(9) Uani 1 1 d . . . H32A H 0.1139 0.0711 0.2896 0.052 Uiso 1 1 calc R . . H32B H 0.1843 0.0741 0.3127 0.052 Uiso 1 1 calc R . . C25 C -0.4002(2) 0.4740(2) 0.0188(3) 0.0480(10) Uani 1 1 d . . . H25A H -0.3655 0.4856 0.0765 0.072 Uiso 1 1 calc R . . H25B H -0.3947 0.427 0.0073 0.072 Uiso 1 1 calc R . . H25C H -0.4412 0.4782 0.0105 0.072 Uiso 1 1 calc R . . C29 C -0.23046(19) 0.59874(19) -0.2680(2) 0.0423(9) Uani 1 1 d . . . H29A H -0.2319 0.6032 -0.3181 0.063 Uiso 1 1 calc R . . H29B H -0.273 0.607 -0.2822 0.063 Uiso 1 1 calc R . . H29C H -0.2165 0.5526 -0.2454 0.063 Uiso 1 1 calc R . . C2 C -0.22657(17) 0.50670(17) -0.0274(2) 0.0335(8) Uani 1 1 d . . . H2 H -0.1891 0.503 -0.0251 0.04 Uiso 1 1 calc R . . C23 C -0.20134(17) 0.39217(18) 0.0400(2) 0.0352(8) Uani 1 1 d . . . C21 C -0.00034(17) 0.32501(18) 0.1559(2) 0.0371(8) Uani 1 1 d . . . H21 H 0.0388 0.345 0.1998 0.045 Uiso 1 1 calc R . . C33 C 0.15230(17) 0.16831(18) 0.3204(2) 0.0381(9) Uani 1 1 d . . . H33A H 0.1867 0.1922 0.3223 0.046 Uiso 1 1 calc R . . H33B H 0.1659 0.1634 0.3782 0.046 Uiso 1 1 calc R . . C43 C -0.1470(2) 0.4242(2) -0.2660(3) 0.0581(12) Uani 1 1 d . . . H43 H -0.1167 0.4585 -0.2537 0.07 Uiso 1 1 calc R . . C27 C -0.45330(19) 0.5049(2) -0.1310(3) 0.0540(11) Uani 1 1 d . . . H27A H -0.4941 0.5082 -0.1387 0.081 Uiso 1 1 calc R . . H27B H -0.4474 0.4583 -0.1429 0.081 Uiso 1 1 calc R . . H27C H -0.4532 0.5367 -0.1689 0.081 Uiso 1 1 calc R . . C24 C -0.39884(17) 0.52323(18) -0.0409(2) 0.0368(8) Uani 1 1 d . . . C46 C -0.0191(2) 0.3901(2) -0.0949(3) 0.0591(12) Uani 1 1 d . . . H46A H -0.0485 0.3585 -0.1399 0.089 Uiso 1 1 calc R . . H46B H 0.0128 0.364 -0.0451 0.089 Uiso 1 1 calc R . . H46C H 0.0024 0.4183 -0.1121 0.089 Uiso 1 1 calc R . . C39 C -0.2021(2) 0.3564(2) -0.2267(3) 0.0545(11) Uani 1 1 d . . . H39 H -0.2101 0.3443 -0.1875 0.065 Uiso 1 1 calc R . . C41 C -0.2259(3) 0.3427(2) -0.3614(3) 0.0717(15) Uani 1 1 d . . . H41 H -0.249 0.3209 -0.4141 0.086 Uiso 1 1 calc R . . C40 C -0.2358(2) 0.3252(2) -0.3044(3) 0.0631(13) Uani 1 1 d . . . H40 H -0.2663 0.2909 -0.3175 0.076 Uiso 1 1 calc R . . C42 C -0.1818(3) 0.3929(3) -0.3424(3) 0.0792(16) Uani 1 1 d . . . H42 H -0.1754 0.4059 -0.3829 0.095 Uiso 1 1 calc R . . C37 C -0.3894(2) 0.6852(2) -0.2806(3) 0.0522(10) Uani 1 1 d . . . H37 H -0.3448 0.7019 -0.2389 0.063 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 Cl3 0.0702(8) 0.0693(8) 0.0515(7) 0.0064(6) 0.0309(6) 0.0004(6) Cl1 0.0623(8) 0.0620(7) 0.0613(7) 0.0018(6) 0.0250(6) -0.0168(6) Cl2 0.0979(12) 0.192(2) 0.0851(11) 0.0195(11) 0.0640(10) 0.0655(13) O2 0.0390(15) 0.0315(14) 0.0566(17) 0.0070(12) 0.0293(14) 0.0064(12) O48 0.0674(19) 0.0441(16) 0.0619(18) 0.0014(13) 0.0470(17) 0.0050(14) O1 0.0519(18) 0.0552(17) 0.0615(18) 0.0254(15) 0.0405(16) 0.0200(14) N8 0.0392(18) 0.0293(15) 0.0475(19) 0.0025(14) 0.0281(16) 0.0003(13) C11 0.033(2) 0.0341(19) 0.036(2) 0.0019(16) 0.0214(18) 0.0008(16) C5 0.0293(19) 0.0344(19) 0.0296(18) -0.0025(15) 0.0177(17) -0.0009(15) N22 0.0346(17) 0.0374(17) 0.0382(17) 0.0082(13) 0.0214(15) 0.0096(14) C14 0.0282(19) 0.0314(19) 0.036(2) 0.0057(15) 0.0174(17) 0.0051(15) C6 0.035(2) 0.0323(19) 0.0336(19) 0.0024(15) 0.0194(17) -0.0022(16) C17 0.033(2) 0.0283(18) 0.038(2) 0.0017(15) 0.0198(18) 0.0014(15) C10 0.0306(19) 0.0293(18) 0.040(2) 0.0000(16) 0.0196(18) 0.0003(15) C19 0.034(2) 0.036(2) 0.039(2) 0.0072(16) 0.0225(19) 0.0071(16) C34 0.035(2) 0.0355(19) 0.037(2) 0.0003(16) 0.0229(18) 0.0007(16) C4 0.0293(19) 0.0308(18) 0.036(2) -0.0005(15) 0.0182(17) 0.0021(15) C38 0.033(2) 0.0344(19) 0.042(2) -0.0004(17) 0.0177(18) 0.0018(16) C13 0.0300(19) 0.0262(17) 0.037(2) 0.0005(15) 0.0184(17) 0.0013(15) C16 0.0284(19) 0.0294(18) 0.0350(19) 0.0045(15) 0.0187(17) 0.0034(15) C30 0.0313(19) 0.0283(18) 0.037(2) 0.0039(15) 0.0206(17) 0.0009(15) C26 0.049(2) 0.034(2) 0.076(3) 0.0005(19) 0.046(2) 0.0056(18) C9 0.0295(19) 0.0278(17) 0.039(2) 0.0063(15) 0.0205(17) 0.0018(15) C12 0.0297(19) 0.0258(17) 0.037(2) 0.0032(15) 0.0198(17) 0.0025(15) N45 0.040(2) 0.0469(19) 0.0436(19) -0.0112(15) 0.0201(17) -0.0057(15) C31 0.041(2) 0.0329(19) 0.041(2) 0.0021(16) 0.0243(19) 0.0023(17) C18 0.034(2) 0.035(2) 0.039(2) 0.0057(16) 0.0217(18) 0.0019(16) C20 0.041(2) 0.0331(19) 0.039(2) 0.0019(16) 0.0247(19) 0.0050(17) C36 0.042(2) 0.042(2) 0.050(2) -0.0010(18) 0.023(2) 0.0050(18) C15 0.0290(19) 0.0297(18) 0.0323(19) 0.0014(15) 0.0156(17) -0.0025(15) C3 0.0285(19) 0.0311(18) 0.0337(19) -0.0016(15) 0.0163(17) -0.0028(15) C35 0.033(2) 0.040(2) 0.054(2) 0.0037(19) 0.019(2) 0.0014(17) C1 0.0307(19) 0.0306(18) 0.0343(19) 0.0009(15) 0.0176(17) 0.0018(15) C44 0.046(2) 0.0304(19) 0.048(2) -0.0002(17) 0.030(2) -0.0018(17) C28 0.041(2) 0.038(2) 0.039(2) 0.0008(17) 0.0227(19) -0.0028(17) C7 0.0295(19) 0.0312(19) 0.036(2) 0.0021(15) 0.0170(17) -0.0023(16) C47 0.056(3) 0.058(3) 0.041(2) -0.014(2) 0.019(2) -0.015(2) C32 0.039(2) 0.042(2) 0.043(2) 0.0083(18) 0.0210(19) 0.0069(18) C25 0.045(2) 0.048(2) 0.061(3) 0.006(2) 0.037(2) 0.0078(19) C29 0.044(2) 0.037(2) 0.043(2) -0.0056(17) 0.025(2) -0.0107(18) C2 0.0308(19) 0.0309(18) 0.038(2) 0.0017(16) 0.0202(17) 0.0030(15) C23 0.033(2) 0.0330(19) 0.039(2) 0.0056(16) 0.0210(18) 0.0009(16) C21 0.033(2) 0.0343(19) 0.041(2) -0.0012(16) 0.0198(18) -0.0019(16) C33 0.037(2) 0.041(2) 0.031(2) 0.0039(16) 0.0175(18) 0.0012(17) C43 0.065(3) 0.052(3) 0.041(2) -0.004(2) 0.022(2) -0.015(2) C27 0.034(2) 0.067(3) 0.054(3) -0.006(2) 0.022(2) -0.007(2) C24 0.036(2) 0.0318(19) 0.047(2) 0.0023(16) 0.0265(19) 0.0037(16) C46 0.039(2) 0.061(3) 0.064(3) -0.010(2) 0.024(2) 0.002(2) C39 0.048(3) 0.041(2) 0.074(3) -0.005(2) 0.036(3) -0.007(2) C41 0.074(4) 0.050(3) 0.045(3) -0.007(2) 0.010(3) 0.001(3) C40 0.038(3) 0.038(2) 0.081(4) -0.013(2) 0.018(3) -0.0056(19) C42 0.114(5) 0.060(3) 0.046(3) 0.003(2) 0.037(3) -0.010(3) C37 0.047(3) 0.062(3) 0.047(2) 0.003(2) 0.027(2) 0.002(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 Cl3 C37 1.756(4) . ? Cl1 C37 1.768(5) . ? Cl2 C37 1.732(4) . ? O2 C7 1.224(4) . ? O48 C44 1.245(4) . ? O1 C23 1.210(4) . ? N8 C7 1.353(4) . ? N8 C9 1.426(4) . ? N8 H8 0.88 . ? C11 C12 1.392(5) . ? C11 C10 1.402(5) . ? C11 H11 0.95 . ? C5 C6 1.379(5) . ? C5 C4 1.407(5) . ? C5 C24 1.529(5) . ? N22 C23 1.363(4) . ? N22 C19 1.437(4) . ? N22 H22 0.88 . ? C14 C13 1.390(5) . ? C14 C9 1.398(5) . ? C14 C28 1.505(5) . ? C6 C1 1.393(5) . ? C6 H6 0.95 . ? C17 C16 1.391(5) . ? C17 C18 1.400(5) . ? C17 H17 0.95 . ? C10 C9 1.386(5) . ? C10 C29 1.511(5) . ? C19 C18 1.381(5) . ? C19 C20 1.392(5) . ? C34 C33 1.533(5) . ? C34 C15 1.542(5) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C4 C3 1.390(5) . ? C4 H4 0.95 . ? C38 C43 1.386(6) . ? C38 C39 1.390(5) . ? C38 C44 1.488(5) . ? C13 C12 1.395(5) . ? C13 H13 0.95 . ? C16 C21 1.400(5) . ? C16 C15 1.541(5) . ? C30 C31 1.524(5) . ? C30 C15 1.552(5) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C26 C24 1.532(5) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C12 C15 1.547(5) 5_565 ? N45 C44 1.352(5) . ? N45 C46 1.457(5) . ? N45 C47 1.457(5) . ? C31 C32 1.525(5) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C18 C35 1.495(5) . ? C20 C21 1.395(5) . ? C20 C36 1.506(5) . ? C36 H36A 0.98 . ? C36 H36B 0.98 . ? C36 H36C 0.98 . ? C15 C12 1.547(5) 5_565 ? C3 C2 1.384(5) . ? C3 C7 1.498(5) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C1 C2 1.383(5) . ? C1 C23 1.507(5) . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C47 C47 1.482(9) 5_565 ? C47 H47A 0.99 . ? C47 H47B 0.99 . ? C32 C33 1.518(5) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C25 C24 1.549(5) . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? C29 H29A 0.98 . ? C29 H29B 0.98 . ? C29 H29C 0.98 . ? C2 H2 0.95 . ? C21 H21 0.95 . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C43 C42 1.374(6) . ? C43 H43 0.95 . ? C27 C24 1.534(6) . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C46 H46A 0.98 . ? C46 H46B 0.98 . ? C46 H46C 0.98 . ? C39 C40 1.392(6) . ? C39 H39 0.95 . ? C41 C40 1.350(7) . ? C41 C42 1.383(7) . ? C41 H41 0.95 . ? C40 H40 0.95 . ? C42 H42 0.95 . ? C37 H37 1 . ? 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 C7 N8 C9 125.3(3) . . ? C7 N8 H8 117.3 . . ? C9 N8 H8 117.3 . . ? C12 C11 C10 121.6(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C6 C5 C4 117.4(3) . . ? C6 C5 C24 122.9(3) . . ? C4 C5 C24 119.7(3) . . ? C23 N22 C19 121.8(3) . . ? C23 N22 H22 119.1 . . ? C19 N22 H22 119.1 . . ? C13 C14 C9 117.8(3) . . ? C13 C14 C28 120.3(3) . . ? C9 C14 C28 121.9(3) . . ? C5 C6 C1 122.0(3) . . ? C5 C6 H6 119 . . ? C1 C6 H6 119 . . ? C16 C17 C18 122.3(3) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C9 C10 C11 118.6(3) . . ? C9 C10 C29 121.5(3) . . ? C11 C10 C29 119.9(3) . . ? C18 C19 C20 121.5(3) . . ? C18 C19 N22 120.5(3) . . ? C20 C19 N22 117.9(3) . . ? C33 C34 C15 113.7(3) . . ? C33 C34 H34A 108.8 . . ? C15 C34 H34A 108.8 . . ? C33 C34 H34B 108.8 . . ? C15 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C3 C4 C5 121.3(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C43 C38 C39 119.5(4) . . ? C43 C38 C44 121.0(3) . . ? C39 C38 C44 119.5(4) . . ? C14 C13 C12 122.5(3) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C17 C16 C21 117.5(3) . . ? C17 C16 C15 123.3(3) . . ? C21 C16 C15 119.2(3) . . ? C31 C30 C15 112.6(3) . . ? C31 C30 H30A 109.1 . . ? C15 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C15 C30 H30B 109.1 . . ? H30A C30 H30B 107.8 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C10 C9 C14 121.7(3) . . ? C10 C9 N8 118.5(3) . . ? C14 C9 N8 119.7(3) . . ? C11 C12 C13 117.7(3) . . ? C11 C12 C15 121.4(3) . 5_565 ? C13 C12 C15 120.6(3) . 5_565 ? C44 N45 C46 124.9(3) . . ? C44 N45 C47 119.4(3) . . ? C46 N45 C47 115.5(3) . . ? C30 C31 C32 111.4(3) . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31B 109.4 . . ? C32 C31 H31B 109.4 . . ? H31A C31 H31B 108 . . ? C19 C18 C17 118.3(3) . . ? C19 C18 C35 120.9(3) . . ? C17 C18 C35 120.8(3) . . ? C19 C20 C21 118.8(3) . . ? C19 C20 C36 120.5(3) . . ? C21 C20 C36 120.7(3) . . ? C20 C36 H36A 109.5 . . ? C20 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C20 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C16 C15 C34 109.3(3) . . ? C16 C15 C12 105.7(3) . 5_565 ? C34 C15 C12 112.9(3) . 5_565 ? C16 C15 C30 111.6(3) . . ? C34 C15 C30 106.7(3) . . ? C12 C15 C30 110.7(3) 5_565 . ? C2 C3 C4 119.6(3) . . ? C2 C3 C7 121.0(3) . . ? C4 C3 C7 119.4(3) . . ? C18 C35 H35A 109.5 . . ? C18 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C18 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C2 C1 C6 119.5(3) . . ? C2 C1 C23 119.5(3) . . ? C6 C1 C23 120.8(3) . . ? O48 C44 N45 122.1(4) . . ? O48 C44 C38 119.9(3) . . ? N45 C44 C38 118.0(3) . . ? C14 C28 H28A 109.5 . . ? C14 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C14 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2 C7 N8 123.1(3) . . ? O2 C7 C3 121.9(3) . . ? N8 C7 C3 114.9(3) . . ? N45 C47 C47 111.8(4) . 5_565 ? N45 C47 H47A 109.2 . . ? C47 C47 H47A 109.2 5_565 . ? N45 C47 H47B 109.2 . . ? C47 C47 H47B 109.2 5_565 . ? H47A C47 H47B 107.9 . . ? C33 C32 C31 111.0(3) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C10 C29 H29A 109.5 . . ? C10 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C10 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? O1 C23 N22 123.0(3) . . ? O1 C23 C1 122.2(3) . . ? N22 C23 C1 114.7(3) . . ? C20 C21 C16 121.6(3) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? C32 C33 C34 112.1(3) . . ? C32 C33 H33A 109.2 . . ? C34 C33 H33A 109.2 . . ? C32 C33 H33B 109.2 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C42 C43 C38 119.4(4) . . ? C42 C43 H43 120.3 . . ? C38 C43 H43 120.3 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C5 C24 C26 112.1(3) . . ? C5 C24 C27 107.1(3) . . ? C26 C24 C27 108.3(3) . . ? C5 C24 C25 111.8(3) . . ? C26 C24 C25 108.2(3) . . ? C27 C24 C25 109.3(3) . . ? N45 C46 H46A 109.5 . . ? N45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? N45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C38 C39 C40 119.4(4) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C40 C41 C42 119.3(4) . . ? C40 C41 H41 120.3 . . ? C42 C41 H41 120.3 . . ? C41 C40 C39 121.1(4) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C43 C42 C41 121.2(5) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? Cl2 C37 Cl3 110.7(2) . . ? Cl2 C37 Cl1 111.3(2) . . ? Cl3 C37 Cl1 109.0(2) . . ? Cl2 C37 H37 108.6 . . ? Cl3 C37 H37 108.6 . . ? Cl1 C37 H37 108.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 O48 0.88 2.21 3.070(4) 164.2 . N22 H22 O48 0.88 2.36 3.057(4) 136.6 . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF