# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Sadler, Peter' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Choi, Jong-Ha' ; ? # Address 2 ; ; ? # Footnote 2 ; _publ_contact_author_name 'Dr Peter Sadler' _publ_contact_author_email P.J.Sadler@warwick.ac.uk _publ_section_title ; Zinc(II) Complexes of Constrained Antiviral Macrocycles ; _publ_requested_coeditor_name S.Moggach@ed.ac.uk _publ_contact_author_address ; Department of Chemistry, Joseph Black Building, West Mains Road, University of Edinburgh, Edinburgh, EH9 3JJ, UK. ; _publ_contact_author_phone '+44 131 650 4806' _publ_contact_letter ; ; # Attachment '- ps6017_complex3.cif' data_ps6017 _database_code_depnum_ccdc_archive 'CCDC 863846' #TrackingRef '- ps6017_complex3.cif' _audit_creation_date 06-02-25 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'ps6017 in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.2392(3) _cell_length_b 10.5922(3) _cell_length_c 13.2643(4) _cell_angle_alpha 90 _cell_angle_beta 105.727(2) _cell_angle_gamma 90 _cell_volume 1249.50(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C24 H46 N4 O4 Zn1 # Dc = 1.38 Fooo = 560.00 Mu = 10.20 M = 260.02 # Found Formula = C24 H46 N4 O4 Zn1 # Dc = 1.38 FOOO = 560.00 Mu = 10.20 M = 260.02 _chemical_formula_sum 'C24 H46 N4 O4 Zn1' _chemical_formula_moiety 'C24 H46 N4 O4 Zn1' _chemical_compound_source ? _chemical_formula_weight 520.03 _cell_measurement_reflns_used 5046 _cell_measurement_theta_min 5 _cell_measurement_theta_max 60 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_max 0.55 _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 1.020 # Sheldrick geometric approximatio 0.64 0.77 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.63 _exptl_absorpt_correction_T_max 0.77 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 22930 _reflns_number_total 3647 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections with Friedels Law is 3647 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3653 _diffrn_reflns_theta_min 2.410 _diffrn_reflns_theta_max 30.025 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.025 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.51 _refine_ls_number_reflns 3636 _refine_ls_number_restraints 6 _refine_ls_number_parameters 151 #_refine_ls_R_factor_ref 0.0321 _refine_ls_wR_factor_ref 0.0685 _refine_ls_goodness_of_fit_ref 0.9120 #_reflns_number_all 3636 _refine_ls_R_factor_all 0.0321 _refine_ls_wR_factor_all 0.0685 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2932 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_gt 0.0676 _refine_ls_shift/su_max 0.000937 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.00P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; 232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O1 .. 70.14 su 232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N1 .. 9.38 su 232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N8 .. 9.55 su The Zn atom does appear to be slightly elongated along the Zn-O bond, however, theprinciple axes of the thermal elipsoids are small, and could easily account for these bonds failing the Hirshfeld test. Principal axes of the thermal ellipsoids, A**2 ZN 1. 0.0115 0.0157 0.0486 C 2. 0.0148 0.0172 0.0199 C 3. 0.0180 0.0213 0.0249 C 4. 0.0166 0.0254 0.0339 C 5. 0.0153 0.0295 0.0354 C 6. 0.0146 0.0254 0.0331 C 7. 0.0140 0.0173 0.0209 C 9. 0.0140 0.0222 0.0340 C 10. 0.0141 0.0237 0.0338 C 11. 0.0146 0.0199 0.0301 C 12. 0.0172 0.0268 0.0376 C 102. 0.0149 0.0191 0.0251 C 103. 0.0188 0.0211 0.0378 N 1. 0.0141 0.0168 0.0223 N 8. 0.0149 0.0176 0.0187 O 1. 0.0169 0.0220 0.0313 O 2. 0.0184 0.0244 0.0409 094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.32 The structure is complete, with residual electron density only left within the bonds themselves. Their also appears to be no twin domains within the crystal. 420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? 720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 No action taken. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Zn1 Zn 1.0000 0.0000 1.0000 0.0253 1.0000 Uani S . . . . . C2 C 1.02372(11) 0.16216(9) 0.82494(7) 0.0173 1.0000 Uani . . . . . . C3 C 1.10479(11) 0.25745(10) 0.77271(8) 0.0214 1.0000 Uani . . . . . . C4 C 1.06518(12) 0.23953(11) 0.65423(8) 0.0253 1.0000 Uani . . . . . . C5 C 1.09535(13) 0.10432(11) 0.62582(8) 0.0267 1.0000 Uani . . . . . . C6 C 1.01053(13) 0.01029(10) 0.67630(8) 0.0244 1.0000 Uani . . . . . . C7 C 1.05305(11) 0.02513(9) 0.79577(7) 0.0174 1.0000 Uani . . . . . . C9 C 0.99392(12) 0.19714(10) 1.15920(8) 0.0234 1.0000 Uani . . . . . . C10 C 1.08761(13) 0.28183(10) 1.10742(8) 0.0238 1.0000 Uani . . . . . . C11 C 1.03916(12) 0.29366(10) 0.98755(8) 0.0215 1.0000 Uani . . . . . . C12 C 0.87662(13) 0.33660(10) 0.94506(9) 0.0272 1.0000 Uani D . . . . . C102 C 1.35391(11) -0.03841(10) 1.11827(8) 0.0197 1.0000 Uani . . . . . . C103 C 1.50560(11) -0.09317(11) 1.11830(8) 0.0259 1.0000 Uani D . . . . . N1 N 1.06688(9) 0.17160(8) 0.94077(6) 0.0177 1.0000 Uani D . . . . . N8 N 0.97130(9) -0.06181(8) 0.84811(6) 0.0171 1.0000 Uani D . . . . . O1 O 1.25187(8) -0.04245(8) 1.03194(6) 0.0234 1.0000 Uani . . . . . . O2 O 1.33960(9) 0.00638(8) 1.20189(6) 0.0279 1.0000 Uani . . . . . . H1 H 1.1640 0.1565 0.9619 0.0269 1.0000 Uiso DR . . . . . H8 H 0.8755 -0.0509 0.8206 0.0257 1.0000 Uiso DR . . . . . H21 H 0.9155 0.1783 0.7995 0.0208 1.0000 Uiso R . . . . . H31 H 1.2135 0.2468 0.8017 0.0263 1.0000 Uiso R . . . . . H32 H 1.0759 0.3430 0.7878 0.0263 1.0000 Uiso R . . . . . H41 H 1.1262 0.2973 0.6250 0.0309 1.0000 Uiso R . . . . . H42 H 0.9584 0.2588 0.6242 0.0309 1.0000 Uiso R . . . . . H51 H 1.2035 0.0871 0.6507 0.0330 1.0000 Uiso R . . . . . H52 H 1.0621 0.0945 0.5496 0.0330 1.0000 Uiso R . . . . . H61 H 1.0352 -0.0757 0.6592 0.0295 1.0000 Uiso R . . . . . H62 H 0.9022 0.0246 0.6483 0.0295 1.0000 Uiso R . . . . . H71 H 1.1609 0.0081 0.8229 0.0210 1.0000 Uiso R . . . . . H91 H 1.0147 0.2203 1.2333 0.0295 1.0000 Uiso R . . . . . H92 H 0.8871 0.2109 1.1244 0.0295 1.0000 Uiso R . . . . . H101 H 1.1907 0.2490 1.1273 0.0290 1.0000 Uiso R . . . . . H102 H 1.0866 0.3669 1.1362 0.0290 1.0000 Uiso R . . . . . H111 H 1.1034 0.3574 0.9679 0.0266 1.0000 Uiso R . . . . . H121 H 0.8565 0.3608 0.8723 0.0404 1.0000 Uiso DR . . . . . H122 H 0.8594 0.4099 0.9850 0.0425 1.0000 Uiso DR . . . . . H123 H 0.8056 0.2708 0.9507 0.0400 1.0000 Uiso DR . . . . . H1031 H 1.5700 -0.1022 1.1896 0.0372 1.0000 Uiso DR . . . . . H1032 H 1.4916 -0.1761 1.0857 0.0417 1.0000 Uiso DR . . . . . H1033 H 1.5568 -0.0398 1.0794 0.0410 1.0000 Uiso DR . . . . . 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 Zn1 0.04794(13) 0.01591(9) 0.01411(9) -0.00245(6) 0.01206(7) -0.00467(8) C2 0.0173(4) 0.0195(5) 0.0150(4) 0.0009(3) 0.0042(3) 0.0009(3) C3 0.0223(5) 0.0207(5) 0.0224(5) 0.0025(4) 0.0082(4) 0.0004(4) C4 0.0253(5) 0.0311(6) 0.0209(5) 0.0060(4) 0.0086(4) 0.0005(4) C5 0.0319(6) 0.0327(6) 0.0179(5) -0.0002(4) 0.0106(4) -0.0031(5) C6 0.0308(5) 0.0275(5) 0.0153(4) -0.0017(4) 0.0072(4) -0.0036(4) C7 0.0174(4) 0.0208(5) 0.0144(4) -0.0010(3) 0.0048(3) -0.0004(3) C9 0.0329(6) 0.0192(5) 0.0213(5) -0.0036(4) 0.0129(4) 0.0007(4) C10 0.0320(6) 0.0192(5) 0.0210(5) -0.0059(4) 0.0083(4) -0.0049(4) C11 0.0290(5) 0.0153(5) 0.0222(5) -0.0024(4) 0.0103(4) -0.0019(4) C12 0.0337(6) 0.0210(5) 0.0288(6) 0.0014(4) 0.0116(5) 0.0075(4) C102 0.0192(4) 0.0197(4) 0.0198(5) 0.0045(4) 0.0048(4) -0.0010(4) C103 0.0211(5) 0.0325(6) 0.0245(5) 0.0081(4) 0.0069(4) 0.0046(4) N1 0.0202(4) 0.0178(4) 0.0146(4) -0.0013(3) 0.0037(3) 0.0020(3) N8 0.0175(4) 0.0178(4) 0.0164(4) -0.0014(3) 0.0054(3) 0.0002(3) O1 0.0207(4) 0.0299(4) 0.0180(3) -0.0002(3) 0.0027(3) 0.0033(3) O2 0.0224(4) 0.0400(5) 0.0197(4) -0.0033(3) 0.0030(3) 0.0012(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6082(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 . O1 2_757 2.2940(7) yes Zn1 . N1 2_757 2.1368(8) yes Zn1 . N8 2_757 2.0660(8) yes Zn1 . N1 . 2.1368(8) yes Zn1 . N8 . 2.0660(8) yes Zn1 . O1 . 2.2940(7) yes C2 . C3 . 1.5301(14) yes C2 . C7 . 1.5449(13) yes C2 . N1 . 1.4823(12) yes C2 . H21 . 0.980 no C3 . C4 . 1.5257(14) yes C3 . H31 . 0.980 no C3 . H32 . 0.980 no C4 . C5 . 1.5257(16) yes C4 . H41 . 0.980 no C4 . H42 . 0.980 no C5 . C6 . 1.5293(15) yes C5 . H51 . 0.980 no C5 . H52 . 0.980 no C6 . C7 . 1.5339(13) yes C6 . H61 . 0.980 no C6 . H62 . 0.980 no C7 . N8 . 1.4780(12) yes C7 . H71 . 0.980 no C9 . N8 2_757 1.4779(13) yes C9 . C10 . 1.5324(15) yes C9 . H91 . 0.980 no C9 . H92 . 0.980 no C10 . C11 . 1.5356(14) yes C10 . H101 . 0.980 no C10 . H102 . 0.980 no C11 . C12 . 1.5234(15) yes C11 . N1 . 1.4861(13) yes C11 . H111 . 0.980 no C12 . H121 . 0.966 no C12 . H122 . 0.977 no C12 . H123 . 0.974 no C102 . C103 . 1.5167(14) yes C102 . O1 . 1.2715(12) yes C102 . O2 . 1.2459(13) yes C103 . H1031 . 0.976 no C103 . H1032 . 0.972 no C103 . H1033 . 0.970 no N1 . H1 . 0.880 no N8 . H8 . 0.869 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 2_757 Zn1 . N1 2_757 81.64(3) yes O1 2_757 Zn1 . N8 2_757 88.49(3) yes N1 2_757 Zn1 . N8 2_757 83.36(3) yes O1 2_757 Zn1 . N1 . 98.36(3) yes N1 2_757 Zn1 . N1 . 179.995 yes N8 2_757 Zn1 . N1 . 96.64(3) yes O1 2_757 Zn1 . N8 . 91.51(3) yes N1 2_757 Zn1 . N8 . 96.64(3) yes N8 2_757 Zn1 . N8 . 179.994 yes N1 . Zn1 . N8 . 83.36(3) yes O1 2_757 Zn1 . O1 . 179.995 yes N1 2_757 Zn1 . O1 . 98.36(3) yes N8 2_757 Zn1 . O1 . 91.51(3) yes N1 . Zn1 . O1 . 81.64(3) yes N8 . Zn1 . O1 . 88.49(3) yes C3 . C2 . C7 . 111.45(8) yes C3 . C2 . N1 . 113.43(8) yes C7 . C2 . N1 . 107.86(8) yes C3 . C2 . H21 . 108.0 no C7 . C2 . H21 . 108.0 no N1 . C2 . H21 . 107.9 no C2 . C3 . C4 . 111.98(8) yes C2 . C3 . H31 . 108.8 no C4 . C3 . H31 . 108.9 no C2 . C3 . H32 . 108.9 no C4 . C3 . H32 . 108.8 no H31 . C3 . H32 . 109.4 no C3 . C4 . C5 . 111.24(9) yes C3 . C4 . H41 . 109.0 no C5 . C4 . H41 . 109.0 no C3 . C4 . H42 . 109.1 no C5 . C4 . H42 . 109.1 no H41 . C4 . H42 . 109.5 no C4 . C5 . C6 . 110.71(9) yes C4 . C5 . H51 . 109.2 no C6 . C5 . H51 . 109.1 no C4 . C5 . H52 . 109.1 no C6 . C5 . H52 . 109.2 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 111.56(8) yes C5 . C6 . H61 . 108.9 no C7 . C6 . H61 . 108.9 no C5 . C6 . H62 . 109.0 no C7 . C6 . H62 . 109.0 no H61 . C6 . H62 . 109.4 no C2 . C7 . C6 . 109.99(8) yes C2 . C7 . N8 . 108.73(8) yes C6 . C7 . N8 . 113.64(8) yes C2 . C7 . H71 . 108.1 no C6 . C7 . H71 . 108.1 no N8 . C7 . H71 . 108.1 no N8 2_757 C9 . C10 . 112.28(8) yes N8 2_757 C9 . H91 . 108.8 no C10 . C9 . H91 . 108.8 no N8 2_757 C9 . H92 . 108.8 no C10 . C9 . H92 . 108.7 no H91 . C9 . H92 . 109.5 no C9 . C10 . C11 . 118.06(9) yes C9 . C10 . H101 . 107.3 no C11 . C10 . H101 . 107.3 no C9 . C10 . H102 . 107.3 no C11 . C10 . H102 . 107.3 no H101 . C10 . H102 . 109.4 no C10 . C11 . C12 . 112.89(9) yes C10 . C11 . N1 . 109.05(8) yes C12 . C11 . N1 . 111.68(8) yes C10 . C11 . H111 . 107.7 no C12 . C11 . H111 . 107.7 no N1 . C11 . H111 . 107.7 no C11 . C12 . H121 . 110.6 no C11 . C12 . H122 . 109.0 no H121 . C12 . H122 . 108.4 no C11 . C12 . H123 . 112.0 no H121 . C12 . H123 . 108.4 no H122 . C12 . H123 . 108.4 no C103 . C102 . O1 . 116.54(9) yes C103 . C102 . O2 . 117.81(9) yes O1 . C102 . O2 . 125.65(9) yes C102 . C103 . H1031 . 111.0 no C102 . C103 . H1032 . 109.5 no H1031 . C103 . H1032 . 108.4 no C102 . C103 . H1033 . 111.1 no H1031 . C103 . H1033 . 108.4 no H1032 . C103 . H1033 . 108.4 no C11 . N1 . C2 . 117.58(8) yes C11 . N1 . Zn1 . 119.13(6) yes C2 . N1 . Zn1 . 107.48(6) yes C11 . N1 . H1 . 107.6 no C2 . N1 . H1 . 106.4 no Zn1 . N1 . H1 . 95.7 no C7 . N8 . C9 2_757 115.19(8) yes C7 . N8 . Zn1 . 108.28(6) yes C9 2_757 N8 . Zn1 . 113.49(6) yes C7 . N8 . H8 . 108.2 no C9 2_757 N8 . H8 . 108.4 no Zn1 . N8 . H8 . 102.4 no Zn1 . O1 . C102 . 128.84(7) yes # Attachment '- ps8010_complex6.cif' data_ps8010 _database_code_depnum_ccdc_archive 'CCDC 863847' #TrackingRef '- ps8010_complex6.cif' _audit_creation_date 08-08-15 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'ps8010 in C2/c' _chemical_name_systematic ? _chemical_melting_point ? _exptl_crystal_recrystallization_method ; ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; This structure is the result of performing data collection on a different crystal of the sample. The crystal, a large plate, cracked during the first data collection. It was therefore suspected that a phase transition or loss of solvent had occurred. Loss of solvent was probable as the structure from the first data collection indicated the presence of large voids with no identifiable peaks of electron density, indicating the presence of a large amount of solvent. Additionally, other crystals left on a slide for several hours became very cracked. However, a second data collection on a different crystal indicates that a different polymorph may exist. DSC did not indicate a phase transition but also suggested that the sample loses solvent readily. This data collection also exhibits large solvent voids and is the same structure as from the first crystal. Unfortunately the contents of the solvent-accessible voids - including the positions of the counter ion (assumed to be chloride) - still cannot be resolved. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; See comment for some explanation of problems encountered during data collection. One of the naphthyl ligands exhibits a high degree of motion and this has been restrained. In the absence of significant anomalous scattering, Friedel pairs were merged. The H atoms on N were located in a difference map. Those attached to carbon atoms were positioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. Checkcif alerts 230_ALERT_2_B Hirshfeld Test Diff for C1 - C22 .. 14.39 su 241_ALERT_2_B Check High Ueq as Compared to Neighbors for C22 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 213_ALERT_2_C Atom C9 has ADP max/min Ratio ............. 3.60 prola 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.87 Ratio 222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.78 Ratio 241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 245_ALERT_2_C U(iso) H221 Smaller than U(eq) C22 by ... 0.02 AngSq 245_ALERT_2_C U(iso) H222 Smaller than U(eq) C22 by ... 0.02 AngSq 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32 341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11 410_ALERT_2_C Short Intra H...H Contact H11 .. H41 .. 1.97 Ang. No action - there are problems arising from the large solvent-accessible void, whose contents are highly disordered. 602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure ! 602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure ! The solvent region was treated by the van der Sluis and Spek method, accounting for 489 e/cell. This is expected to include one Cl^-^ counterion per formula unit. However, the rest of the solvent-accessible void contents is completely unidentifiable and so the values of F(000), M, mu, D have been calculated on the basis of the identified formula unit only. See also comment above. 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 1 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/L= 0.600 1 912_ALERT_3_C # Missing FCF Reflections Above STh/L= 0.600 36 913_ALERT_3_C # Missing Very Strong Reflections in FCF ....... 2 #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 4954 4952 2 23.01 0.550 1.000 6595 6593 2 25.24 0.600 1.000 8543 8541 2 #----------------------------------------------------------- ACTA Min. Res. --- 26.48 0.627 0.996 9771 9733 38 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 78 U(IJ)'S 0.0, 0.0010000 = C(25) TO C(26) U(IJ)'S 0.0, 0.0010000 = C(23) TO C(28) U(IJ)'S 0.0, 0.0010000 = C(22) TO C(30) U(IJ)'S 0.0, 0.0010000 = C(23) TO C(24) U(IJ)'S 0.0, 0.0010000 = C(24) TO C(25) U(IJ)'S 0.0, 0.0010000 = C(24) TO C(33) U(IJ)'S 0.0, 0.0010000 = C(32) TO C(33) U(IJ)'S 0.0, 0.0010000 = C(31) TO C(32) U(IJ)'S 0.0, 0.0010000 = C(30) TO C(31) U(IJ)'S 0.0, 0.0010000 = C(29) TO C(30) U(IJ)'S 0.0, 0.0010000 = C(26) TO C(27) U(IJ)'S 0.0, 0.0010000 = C(27) TO C(28) U(IJ)'S 0.0, 0.0010000 = N(13) TO C(34) ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.000 -0.004 1468.8 244.6 2 0.000 0.500 0.022 1468.9 244.6 _platon_squeeze_details ; Summary and Remarks : N = NOTE, W = WARNING, E = ERROR #=============================================================================== N: No S.U.'s (esd) on observed/calculated parameters. #------------------------------------------------------------------------------- N: Number of Ignored Lines on INPUT ...................................... 4 of which blank in column 1 ..................................... 4 W: Number of unusual anisotropic displacement parameters ................. 9 N: Total Potential Solvent Accessible Void Vol .................. 2951.1 Ang^3^ N: Electron Count / Cell = 489 - To be included in D(calc), F000 & Mol.Wght. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 24.5797(11) _cell_length_b 29.3304(12) _cell_length_c 13.1572(6) _cell_angle_alpha 90 _cell_angle_beta 95.597(3) _cell_angle_gamma 90 _cell_volume 9440.2(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C42 H56 Cl2 N4 O2 Zn1 # Dc = 1.10 Fooo = 3064.00 Mu = 6.68 M = 785.22 # Found Formula = C42 H56 Cl1 N4 Zn1 # Dc = 1.01 FOOO = 3064.00 Mu = 6.05 M = 717.77 _chemical_formula_sum 'C42 H56 Cl1 N4 Zn1' _chemical_formula_moiety 'C42 H56 Cl1 N4 Zn1' _chemical_compound_source ? _chemical_formula_weight 717.77 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.49 _exptl_crystal_density_diffrn 1.010 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 3064 _exptl_absorpt_coefficient_mu 0.605 # Sheldrick geometric approximatio 0.88 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 33746 _reflns_number_total 9733 _diffrn_reflns_av_R_equivalents 0.088 # Number of reflections with Friedels Law is 9733 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9765 _diffrn_reflns_theta_min 1.389 _diffrn_reflns_theta_max 26.481 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.481 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -30 _reflns_limit_h_max 30 _reflns_limit_k_min 0 _reflns_limit_k_max 36 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.80 _refine_diff_density_max 1.70 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 9694 _refine_ls_number_restraints 78 _refine_ls_number_parameters 433 _oxford_refine_ls_R_factor_ref 0.1231 _refine_ls_wR_factor_ref 0.2018 _refine_ls_goodness_of_fit_ref 0.9423 _refine_ls_shift/su_max 0.000372 # The values computed from all data _oxford_reflns_number_all 9694 _refine_ls_R_factor_all 0.1231 _refine_ls_wR_factor_all 0.2018 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6280 _refine_ls_R_factor_gt 0.0881 _refine_ls_wR_factor_gt 0.1720 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.3226(3) 0.12828(19) 0.5760(4) 0.0335 1.0000 Uani . . . . . . . N2 N 0.3429(2) 0.15091(16) 0.4855(4) 0.0343 1.0000 Uani . . . . . . . C3 C 0.3970(3) 0.1326(2) 0.4650(5) 0.0411 1.0000 Uani . . . . . . . C4 C 0.3985(3) 0.0830(2) 0.4334(5) 0.0400 1.0000 Uani . . . . . . . C5 C 0.3729(3) 0.0731(2) 0.3246(5) 0.0377 1.0000 Uani . . . . . . . N6 N 0.3159(2) 0.08970(15) 0.3149(3) 0.0298 1.0000 Uani . . . . . . . C7 C 0.2891(3) 0.09240(18) 0.2070(4) 0.0310 1.0000 Uani . . . . . . . C8 C 0.3133(3) 0.1315(2) 0.1484(5) 0.0432 1.0000 Uani . . . . . . . C9 C 0.2838(4) 0.1363(2) 0.0427(4) 0.0520 1.0000 Uani . . . . . . . C10 C 0.2234(4) 0.1424(2) 0.0472(5) 0.0519 1.0000 Uani . . . . . . . C11 C 0.1985(3) 0.1031(2) 0.1023(4) 0.0420 1.0000 Uani . . . . . . . C12 C 0.2282(3) 0.09839(18) 0.2105(4) 0.0311 1.0000 Uani . . . . . . . N13 N 0.2051(2) 0.06207(15) 0.2770(3) 0.0288 1.0000 Uani . U . . . . . C14 C 0.1492(2) 0.07359(18) 0.3036(4) 0.0305 1.0000 Uani . . . . . . . C15 C 0.1444(2) 0.11776(19) 0.3631(4) 0.0312 1.0000 Uani . . . . . . . C16 C 0.1700(2) 0.11962(18) 0.4733(4) 0.0281 1.0000 Uani . . . . . . . N17 N 0.23110(19) 0.12004(14) 0.4771(3) 0.0262 1.0000 Uani . . . . . . . C18 C 0.2610(2) 0.13210(18) 0.5792(4) 0.0296 1.0000 Uani . . . . . . . C19 C 0.2434(3) 0.1011(2) 0.6634(4) 0.0360 1.0000 Uani . . . . . . . C20 C 0.2735(3) 0.1124(2) 0.7666(4) 0.0482 1.0000 Uani . . . . . . . C21 C 0.3343(3) 0.1117(2) 0.7642(4) 0.0491 1.0000 Uani . . . . . . . C22 C 0.3521(5) 0.1426(3) 0.6794(7) 0.0771 1.0000 Uani . U . . . . . C23 C 0.3464(5) 0.2011(3) 0.4978(7) 0.0772 1.0000 Uani . U . . . . . C24 C 0.3535(5) 0.2246(3) 0.3997(7) 0.0773 1.0000 Uani . U . . . . . C25 C 0.3092(5) 0.2347(3) 0.3284(7) 0.0769 1.0000 Uani . U . . . . . C26 C 0.2560(5) 0.2259(3) 0.3469(7) 0.0772 1.0000 Uani . U . . . . . C27 C 0.2101(5) 0.2354(3) 0.2776(7) 0.0783 1.0000 Uani . U . . . . . C28 C 0.2201(5) 0.2540(3) 0.1841(7) 0.0784 1.0000 Uani . U . . . . . C29 C 0.2706(5) 0.2629(3) 0.1652(7) 0.0785 1.0000 Uani . U . . . . . C30 C 0.3183(5) 0.2564(3) 0.2327(7) 0.0783 1.0000 Uani . U . . . . . C31 C 0.3676(5) 0.2677(3) 0.2125(7) 0.0793 1.0000 Uani . U . . . . . C32 C 0.4120(5) 0.2628(3) 0.2811(7) 0.0794 1.0000 Uani . U . . . . . C33 C 0.4056(5) 0.2403(3) 0.3776(7) 0.0785 1.0000 Uani . U . . . . . C34 C 0.2081(2) 0.01466(17) 0.2294(4) 0.0285 1.0000 Uani . U . . . . . C35 C 0.1630(3) -0.0184(2) 0.2437(5) 0.0466 1.0000 Uani . . . . . . . C36 C 0.1222(3) -0.0284(2) 0.1675(6) 0.0497 1.0000 Uani . . . . . . . C37 C 0.1155(3) -0.0024(3) 0.0731(5) 0.0507 1.0000 Uani . . . . . . . C38 C 0.0743(3) -0.0149(3) 0.0003(6) 0.0528 1.0000 Uani . . . . . . . C39 C 0.0410(3) -0.0519(3) 0.0111(7) 0.0638 1.0000 Uani . . . . . . . C40 C 0.0457(4) -0.0765(3) 0.0966(7) 0.0665 1.0000 Uani . . . . . . . C41 C 0.0841(3) -0.0655(2) 0.1760(5) 0.0448 1.0000 Uani . . . . . . . C42 C 0.0896(4) -0.0906(3) 0.2711(6) 0.0642 1.0000 Uani . . . . . . . C43 C 0.1269(3) -0.0793(3) 0.3471(6) 0.0555 1.0000 Uani . . . . . . . C44 C 0.1634(3) -0.0441(2) 0.3322(5) 0.0512 1.0000 Uani . . . . . . . C45 C 0.3752(3) 0.0231(2) 0.2979(5) 0.0482 1.0000 Uani . . . . . . . C46 C 0.1478(3) 0.1616(2) 0.5239(5) 0.0379 1.0000 Uani . . . . . . . Zn1 Zn 0.26026(3) 0.06413(2) 0.40629(4) 0.0247 1.0000 Uani . . . . . . . Cl1 Cl 0.27847(7) 0.00203(5) 0.49638(11) 0.0381 1.0000 Uani . . . . . . . H161 H 0.1588 0.0925 0.5082 0.0348 1.0000 Uiso . . . . . . . H151 H 0.1596 0.1423 0.3260 0.0365 1.0000 Uiso . . . . . . . H152 H 0.1059 0.1229 0.3656 0.0366 1.0000 Uiso . . . . . . . H142 H 0.1364 0.0487 0.3434 0.0366 1.0000 Uiso . . . . . . . H141 H 0.1259 0.0758 0.2407 0.0369 1.0000 Uiso . . . . . . . H121 H 0.2241 0.1278 0.2444 0.0363 1.0000 Uiso . . . . . . . H71 H 0.2960 0.0635 0.1733 0.0378 1.0000 Uiso . . . . . . . H51 H 0.3927 0.0901 0.2775 0.0467 1.0000 Uiso . . . . . . . H42 H 0.4364 0.0737 0.4372 0.0477 1.0000 Uiso . . . . . . . H41 H 0.3791 0.0649 0.4793 0.0480 1.0000 Uiso . . . . . . . H31 H 0.4217 0.1363 0.5258 0.0491 1.0000 Uiso . . . . . . . H32 H 0.4103 0.1507 0.4122 0.0490 1.0000 Uiso . . . . . . . H11 H 0.3308 0.0958 0.5689 0.0398 1.0000 Uiso . . . . . . . H181 H 0.2519 0.1637 0.5949 0.0354 1.0000 Uiso . . . . . . . H192 H 0.2523 0.0699 0.6470 0.0446 1.0000 Uiso . . . . . . . H191 H 0.2042 0.1031 0.6672 0.0448 1.0000 Uiso . . . . . . . H202 H 0.2635 0.1431 0.7851 0.0575 1.0000 Uiso . . . . . . . H201 H 0.2636 0.0910 0.8166 0.0579 1.0000 Uiso . . . . . . . H211 H 0.3515 0.1216 0.8288 0.0576 1.0000 Uiso . . . . . . . H212 H 0.3451 0.0808 0.7511 0.0577 1.0000 Uiso . . . . . . . H222 H 0.3913 0.1406 0.6772 0.0546 1.0000 Uiso . . . . . . . H221 H 0.3422 0.1737 0.6951 0.0545 1.0000 Uiso . . . . . . . H231 H 0.3779 0.2079 0.5452 0.0690 1.0000 Uiso . . . . . . . H232 H 0.3138 0.2122 0.5247 0.0688 1.0000 Uiso . . . . . . . H261 H 0.2491 0.2130 0.4084 0.0867 1.0000 Uiso . . . . . . . H271 H 0.1749 0.2295 0.2934 0.1121 1.0000 Uiso . . . . . . . H281 H 0.1895 0.2596 0.1346 0.1291 1.0000 Uiso . . . . . . . H291 H 0.2769 0.2751 0.1015 0.1219 1.0000 Uiso . . . . . . . H311 H 0.3739 0.2804 0.1500 0.1099 1.0000 Uiso . . . . . . . H331 H 0.4350 0.2352 0.4259 0.1067 1.0000 Uiso . . . . . . . H321 H 0.4482 0.2737 0.2704 0.1091 1.0000 Uiso . . . . . . . H453 H 0.4117 0.0123 0.3081 0.0727 1.0000 Uiso . . . . . . . H451 H 0.3528 0.0060 0.3401 0.0726 1.0000 Uiso . . . . . . . H452 H 0.3610 0.0185 0.2286 0.0728 1.0000 Uiso . . . . . . . H81 H 0.3518 0.1251 0.1440 0.0516 1.0000 Uiso . . . . . . . H82 H 0.3097 0.1595 0.1859 0.0520 1.0000 Uiso . . . . . . . H112 H 0.2030 0.0751 0.0657 0.0508 1.0000 Uiso . . . . . . . H111 H 0.1599 0.1088 0.1069 0.0507 1.0000 Uiso . . . . . . . H102 H 0.2160 0.1705 0.0819 0.0618 1.0000 Uiso . . . . . . . H101 H 0.2054 0.1439 -0.0208 0.0620 1.0000 Uiso . . . . . . . H92 H 0.2983 0.1627 0.0104 0.0639 1.0000 Uiso . . . . . . . H91 H 0.2906 0.1093 0.0031 0.0639 1.0000 Uiso . . . . . . . H342 H 0.2421 0.0005 0.2569 0.0349 1.0000 Uiso . . . . . . . H341 H 0.2094 0.0192 0.1568 0.0342 1.0000 Uiso . . . . . . . H421 H 0.0663 -0.1152 0.2803 0.0783 1.0000 Uiso . . . . . . . H431 H 0.1281 -0.0945 0.4090 0.0663 1.0000 Uiso . . . . . . . H441 H 0.1904 -0.0376 0.3847 0.0620 1.0000 Uiso . . . . . . . H401 H 0.0223 -0.1015 0.1034 0.0800 1.0000 Uiso . . . . . . . H391 H 0.0148 -0.0600 -0.0425 0.0772 1.0000 Uiso . . . . . . . H381 H 0.0689 0.0022 -0.0592 0.0640 1.0000 Uiso . . . . . . . H371 H 0.1382 0.0223 0.0621 0.0606 1.0000 Uiso . . . . . . . H461 H 0.1089 0.1608 0.5173 0.0556 1.0000 Uiso . . . . . . . H463 H 0.1612 0.1619 0.5949 0.0555 1.0000 Uiso . . . . . . . H462 H 0.1604 0.1887 0.4922 0.0559 1.0000 Uiso . . . . . . . H171 H 0.2379 0.1430 0.4378 0.0389 1.0000 Uiso . . . . . . . H61 H 0.3199 0.1185 0.3351 0.0461 1.0000 Uiso . . . . . . . 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 0.049(4) 0.025(3) 0.027(3) -0.004(2) 0.007(3) -0.004(3) N2 0.043(3) 0.028(2) 0.033(3) -0.005(2) 0.015(2) -0.005(2) C3 0.039(4) 0.052(4) 0.033(3) -0.003(3) 0.008(3) -0.015(3) C4 0.033(3) 0.048(4) 0.040(3) 0.002(3) 0.007(3) 0.003(3) C5 0.044(4) 0.031(3) 0.042(3) -0.001(3) 0.022(3) -0.001(3) N6 0.044(3) 0.022(2) 0.026(2) -0.0036(18) 0.016(2) -0.003(2) C7 0.055(4) 0.023(3) 0.017(2) -0.003(2) 0.011(2) -0.003(3) C8 0.063(4) 0.033(3) 0.035(3) 0.000(3) 0.014(3) -0.013(3) C9 0.097(6) 0.050(4) 0.012(3) 0.004(3) 0.017(3) -0.016(4) C10 0.096(6) 0.037(4) 0.022(3) 0.004(3) 0.004(3) -0.006(4) C11 0.071(5) 0.034(3) 0.021(3) 0.002(2) -0.001(3) -0.002(3) C12 0.061(4) 0.020(2) 0.013(2) -0.0024(19) 0.007(2) -0.003(2) N13 0.052(2) 0.0169(17) 0.0178(16) -0.0071(14) 0.0073(15) -0.0031(16) C14 0.047(3) 0.023(3) 0.022(3) -0.002(2) 0.003(2) 0.000(2) C15 0.036(3) 0.025(3) 0.032(3) -0.002(2) 0.004(2) 0.008(2) C16 0.035(3) 0.025(3) 0.024(3) -0.006(2) 0.007(2) 0.003(2) N17 0.044(3) 0.017(2) 0.018(2) 0.0016(16) 0.0096(19) 0.0012(19) C18 0.043(3) 0.023(3) 0.023(3) -0.003(2) 0.008(2) -0.001(2) C19 0.060(4) 0.035(3) 0.015(2) -0.001(2) 0.009(2) -0.007(3) C20 0.082(5) 0.047(4) 0.016(3) -0.001(3) 0.004(3) -0.014(4) C21 0.074(5) 0.051(4) 0.019(3) 0.002(3) -0.012(3) -0.004(4) C22 0.135(3) 0.0369(18) 0.063(2) -0.0038(17) 0.033(2) 0.001(2) C23 0.137(3) 0.0336(15) 0.0655(19) -0.0057(14) 0.0316(19) -0.0001(18) C24 0.137(3) 0.0339(14) 0.0660(18) -0.0056(14) 0.0328(18) 0.0002(17) C25 0.137(3) 0.0327(15) 0.0655(19) -0.0060(14) 0.0320(19) 0.0005(18) C26 0.137(3) 0.0326(15) 0.066(2) -0.0057(15) 0.0304(19) 0.0006(18) C27 0.138(3) 0.0339(15) 0.067(2) -0.0054(15) 0.029(2) 0.0005(18) C28 0.138(3) 0.0345(15) 0.0668(19) -0.0054(15) 0.0298(19) 0.0003(18) C29 0.137(3) 0.0373(18) 0.065(2) -0.0032(18) 0.033(2) 0.001(2) C30 0.137(3) 0.0373(16) 0.065(2) -0.0036(16) 0.033(2) 0.0013(19) C31 0.138(3) 0.0381(15) 0.0670(19) -0.0038(15) 0.0338(19) 0.0011(18) C32 0.137(3) 0.0378(15) 0.0680(19) -0.0042(15) 0.0343(18) 0.0007(17) C33 0.137(3) 0.0361(14) 0.0672(18) -0.0049(14) 0.0341(18) 0.0005(17) C34 0.052(2) 0.0169(17) 0.0172(16) -0.0078(14) 0.0078(16) -0.0035(17) C35 0.069(5) 0.033(3) 0.040(4) -0.010(3) 0.016(3) 0.003(3) C36 0.051(4) 0.047(4) 0.052(4) -0.018(3) 0.013(3) 0.011(3) C37 0.064(5) 0.050(4) 0.040(4) 0.001(3) 0.012(3) 0.017(4) C38 0.049(4) 0.055(4) 0.056(4) 0.003(3) 0.014(3) 0.009(4) C39 0.057(5) 0.060(5) 0.075(6) -0.004(4) 0.010(4) 0.007(4) C40 0.060(5) 0.063(5) 0.077(6) -0.012(4) 0.007(4) 0.001(4) C41 0.046(4) 0.041(4) 0.050(4) -0.009(3) 0.017(3) -0.003(3) C42 0.079(6) 0.057(5) 0.060(5) 0.003(4) 0.023(4) -0.003(4) C43 0.065(5) 0.060(5) 0.042(4) -0.008(3) 0.007(4) 0.008(4) C44 0.082(5) 0.037(4) 0.038(4) 0.008(3) 0.023(4) 0.005(4) C45 0.051(4) 0.046(4) 0.052(4) -0.006(3) 0.026(3) 0.014(3) C46 0.045(4) 0.035(3) 0.035(3) -0.005(3) 0.009(3) 0.013(3) Zn1 0.0388(3) 0.0203(3) 0.0162(3) 0.0006(2) 0.0101(2) 0.0019(3) Cl1 0.0601(10) 0.0262(7) 0.0301(7) 0.0077(6) 0.0150(6) 0.0062(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.13945(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . N2 . 1.490(7) yes C1 . C18 . 1.524(8) yes C1 . C22 . 1.536(11) yes C1 . H11 . 0.981 no N2 . C3 . 1.482(8) yes N2 . C23 . 1.484(9) yes C3 . C4 . 1.514(9) yes C3 . H31 . 0.963 no C3 . H32 . 0.958 no C4 . C5 . 1.535(9) yes C4 . H42 . 0.967 no C4 . H41 . 0.966 no C5 . N6 . 1.476(8) yes C5 . C45 . 1.511(9) yes C5 . H51 . 0.963 no N6 . C7 . 1.509(7) yes N6 . Zn1 . 2.050(4) yes N6 . H61 . 0.888 no C7 . C8 . 1.534(8) yes C7 . C12 . 1.513(9) yes C7 . H71 . 0.979 no C8 . C9 . 1.511(9) yes C8 . H81 . 0.972 no C8 . H82 . 0.966 no C9 . C10 . 1.502(11) yes C9 . H92 . 0.968 no C9 . H91 . 0.971 no C10 . C11 . 1.520(9) yes C10 . H102 . 0.969 no C10 . H101 . 0.959 no C11 . C12 . 1.541(8) yes C11 . H112 . 0.964 no C11 . H111 . 0.971 no C12 . N13 . 1.523(7) yes C12 . H121 . 0.981 no N13 . C14 . 1.490(7) yes N13 . C34 . 1.529(6) yes N13 . Zn1 . 2.070(4) yes C14 . C15 . 1.524(7) yes C14 . H142 . 0.969 no C14 . H141 . 0.962 no C15 . C16 . 1.523(8) yes C15 . H151 . 0.965 no C15 . H152 . 0.963 no C16 . N17 . 1.498(7) yes C16 . C46 . 1.524(7) yes C16 . H161 . 0.971 no N17 . C18 . 1.510(7) yes N17 . Zn1 . 2.050(4) yes N17 . H171 . 0.875 no C18 . C19 . 1.527(7) yes C18 . H181 . 0.982 no C19 . C20 . 1.519(8) yes C19 . H192 . 0.971 no C19 . H191 . 0.970 no C20 . C21 . 1.499(11) yes C20 . H202 . 0.970 no C20 . H201 . 0.957 no C21 . C22 . 1.533(10) yes C21 . H211 . 0.956 no C21 . H212 . 0.966 no C22 . H222 . 0.969 no C22 . H221 . 0.973 no C23 . C24 . 1.488(12) yes C23 . H231 . 0.967 no C23 . H232 . 0.963 no C24 . C25 . 1.397(14) yes C24 . C33 . 1.418(14) yes C25 . C26 . 1.377(14) yes C25 . C30 . 1.448(12) yes C26 . C27 . 1.408(14) yes C26 . H261 . 0.925 no C27 . C28 . 1.390(12) yes C27 . H271 . 0.926 no C28 . C29 . 1.315(14) yes C28 . H281 . 0.960 no C29 . C30 . 1.414(14) yes C29 . H291 . 0.939 no C30 . C31 . 1.307(14) yes C31 . C32 . 1.353(14) yes C31 . H311 . 0.930 no C32 . C33 . 1.453(12) yes C32 . H321 . 0.969 no C33 . H331 . 0.926 no C34 . C35 . 1.498(9) yes C34 . H342 . 0.971 no C34 . H341 . 0.968 no C35 . C36 . 1.378(10) yes C35 . C44 . 1.386(9) yes C36 . C37 . 1.454(10) yes C36 . C41 . 1.448(10) yes C37 . C38 . 1.374(10) yes C37 . H371 . 0.933 no C38 . C39 . 1.375(11) yes C38 . H381 . 0.929 no C39 . C40 . 1.332(12) yes C39 . H391 . 0.937 no C40 . C41 . 1.377(11) yes C40 . H401 . 0.940 no C41 . C42 . 1.447(10) yes C42 . C43 . 1.330(11) yes C42 . H421 . 0.938 no C43 . C44 . 1.394(10) yes C43 . H431 . 0.926 no C44 . H441 . 0.930 no C45 . H453 . 0.949 no C45 . H451 . 0.960 no C45 . H452 . 0.954 no C46 . H461 . 0.952 no C46 . H463 . 0.961 no C46 . H462 . 0.963 no Zn1 . Cl1 . 2.1952(15) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 . C1 . C18 . 113.6(5) yes N2 . C1 . C22 . 114.9(5) yes C18 . C1 . C22 . 109.8(6) yes N2 . C1 . H11 . 105.6 no C18 . C1 . H11 . 106.7 no C22 . C1 . H11 . 105.5 no C1 . N2 . C3 . 111.1(5) yes C1 . N2 . C23 . 112.1(5) yes C3 . N2 . C23 . 109.6(6) yes N2 . C3 . C4 . 116.4(5) yes N2 . C3 . H31 . 108.3 no C4 . C3 . H31 . 107.7 no N2 . C3 . H32 . 108.0 no C4 . C3 . H32 . 108.3 no H31 . C3 . H32 . 107.9 no C3 . C4 . C5 . 114.8(5) yes C3 . C4 . H42 . 107.9 no C5 . C4 . H42 . 107.4 no C3 . C4 . H41 . 109.3 no C5 . C4 . H41 . 107.2 no H42 . C4 . H41 . 110.3 no C4 . C5 . N6 . 108.5(5) yes C4 . C5 . C45 . 112.3(6) yes N6 . C5 . C45 . 110.9(5) yes C4 . C5 . H51 . 108.4 no N6 . C5 . H51 . 108.0 no C45 . C5 . H51 . 108.6 no C5 . N6 . C7 . 115.0(4) yes C5 . N6 . Zn1 . 120.7(3) yes C7 . N6 . Zn1 . 108.4(3) yes C5 . N6 . H61 . 102.2 no C7 . N6 . H61 . 104.9 no Zn1 . N6 . H61 . 103.5 no N6 . C7 . C8 . 110.9(5) yes N6 . C7 . C12 . 108.7(4) yes C8 . C7 . C12 . 111.2(5) yes N6 . C7 . H71 . 107.5 no C8 . C7 . H71 . 109.1 no C12 . C7 . H71 . 109.3 no C7 . C8 . C9 . 110.9(5) yes C7 . C8 . H81 . 108.1 no C9 . C8 . H81 . 110.2 no C7 . C8 . H82 . 108.7 no C9 . C8 . H82 . 109.4 no H81 . C8 . H82 . 109.5 no C8 . C9 . C10 . 111.2(5) yes C8 . C9 . H92 . 108.2 no C10 . C9 . H92 . 109.4 no C8 . C9 . H91 . 109.0 no C10 . C9 . H91 . 109.9 no H92 . C9 . H91 . 109.1 no C9 . C10 . C11 . 112.0(6) yes C9 . C10 . H102 . 110.5 no C11 . C10 . H102 . 108.5 no C9 . C10 . H101 . 109.6 no C11 . C10 . H101 . 108.1 no H102 . C10 . H101 . 108.0 no C10 . C11 . C12 . 109.5(5) yes C10 . C11 . H112 . 109.6 no C12 . C11 . H112 . 108.6 no C10 . C11 . H111 . 109.9 no C12 . C11 . H111 . 109.6 no H112 . C11 . H111 . 109.6 no C11 . C12 . C7 . 111.2(5) yes C11 . C12 . N13 . 115.1(5) yes C7 . C12 . N13 . 111.2(4) yes C11 . C12 . H121 . 106.3 no C7 . C12 . H121 . 105.2 no N13 . C12 . H121 . 107.1 no C12 . N13 . C14 . 112.4(4) yes C12 . N13 . C34 . 111.4(4) yes C14 . N13 . C34 . 112.7(4) yes C12 . N13 . Zn1 . 101.5(3) yes C14 . N13 . Zn1 . 110.2(3) yes C34 . N13 . Zn1 . 108.0(3) yes N13 . C14 . C15 . 115.6(5) yes N13 . C14 . H142 . 108.1 no C15 . C14 . H142 . 108.6 no N13 . C14 . H141 . 107.3 no C15 . C14 . H141 . 108.4 no H142 . C14 . H141 . 108.6 no C14 . C15 . C16 . 118.3(5) yes C14 . C15 . H151 . 108.8 no C16 . C15 . H151 . 108.1 no C14 . C15 . H152 . 106.0 no C16 . C15 . H152 . 106.2 no H151 . C15 . H152 . 109.2 no C15 . C16 . N17 . 110.5(4) yes C15 . C16 . C46 . 108.2(5) yes N17 . C16 . C46 . 112.3(5) yes C15 . C16 . H161 . 108.2 no N17 . C16 . H161 . 108.6 no C46 . C16 . H161 . 108.9 no C16 . N17 . C18 . 115.5(4) yes C16 . N17 . Zn1 . 111.8(3) yes C18 . N17 . Zn1 . 115.5(3) yes C16 . N17 . H171 . 103.7 no C18 . N17 . H171 . 104.0 no Zn1 . N17 . H171 . 104.6 no C1 . C18 . N17 . 110.9(4) yes C1 . C18 . C19 . 109.3(5) yes N17 . C18 . C19 . 111.0(4) yes C1 . C18 . H181 . 108.9 no N17 . C18 . H181 . 107.9 no C19 . C18 . H181 . 108.9 no C18 . C19 . C20 . 111.8(5) yes C18 . C19 . H192 . 108.3 no C20 . C19 . H192 . 107.6 no C18 . C19 . H191 . 110.8 no C20 . C19 . H191 . 109.8 no H192 . C19 . H191 . 108.3 no C19 . C20 . C21 . 112.2(5) yes C19 . C20 . H202 . 108.3 no C21 . C20 . H202 . 107.1 no C19 . C20 . H201 . 109.7 no C21 . C20 . H201 . 109.1 no H202 . C20 . H201 . 110.4 no C20 . C21 . C22 . 111.3(6) yes C20 . C21 . H211 . 109.3 no C22 . C21 . H211 . 109.7 no C20 . C21 . H212 . 107.9 no C22 . C21 . H212 . 108.8 no H211 . C21 . H212 . 109.8 no C1 . C22 . C21 . 109.9(7) yes C1 . C22 . H222 . 110.0 no C21 . C22 . H222 . 109.9 no C1 . C22 . H221 . 109.8 no C21 . C22 . H221 . 107.8 no H222 . C22 . H221 . 109.4 no N2 . C23 . C24 . 112.0(6) yes N2 . C23 . H231 . 108.0 no C24 . C23 . H231 . 108.1 no N2 . C23 . H232 . 109.5 no C24 . C23 . H232 . 109.6 no H231 . C23 . H232 . 109.6 no C23 . C24 . C25 . 122.1(10) yes C23 . C24 . C33 . 120.9(10) yes C25 . C24 . C33 . 117.0(9) yes C24 . C25 . C26 . 122.2(9) yes C24 . C25 . C30 . 120.0(10) yes C26 . C25 . C30 . 117.7(10) yes C25 . C26 . C27 . 124.4(9) yes C25 . C26 . H261 . 119.4 no C27 . C26 . H261 . 116.2 no C26 . C27 . C28 . 116.8(10) yes C26 . C27 . H271 . 121.7 no C28 . C27 . H271 . 121.5 no C27 . C28 . C29 . 119.8(11) yes C27 . C28 . H281 . 118.2 no C29 . C28 . H281 . 122.0 no C28 . C29 . C30 . 126.6(9) yes C28 . C29 . H291 . 119.0 no C30 . C29 . H291 . 114.4 no C25 . C30 . C29 . 114.6(10) yes C25 . C30 . C31 . 120.8(11) yes C29 . C30 . C31 . 124.6(9) yes C30 . C31 . C32 . 122.7(10) yes C30 . C31 . H311 . 121.2 no C32 . C31 . H311 . 116.1 no C31 . C32 . C33 . 118.8(10) yes C31 . C32 . H321 . 124.1 no C33 . C32 . H321 . 117.1 no C32 . C33 . C24 . 120.2(10) yes C32 . C33 . H331 . 122.0 no C24 . C33 . H331 . 117.7 no N13 . C34 . C35 . 118.1(5) yes N13 . C34 . H342 . 108.2 no C35 . C34 . H342 . 107.2 no N13 . C34 . H341 . 106.6 no C35 . C34 . H341 . 107.9 no H342 . C34 . H341 . 108.5 no C34 . C35 . C36 . 122.8(6) yes C34 . C35 . C44 . 120.9(7) yes C36 . C35 . C44 . 116.1(7) yes C35 . C36 . C37 . 121.6(7) yes C35 . C36 . C41 . 122.3(7) yes C37 . C36 . C41 . 116.1(7) yes C36 . C37 . C38 . 118.1(7) yes C36 . C37 . H371 . 121.2 no C38 . C37 . H371 . 120.7 no C37 . C38 . C39 . 123.0(8) yes C37 . C38 . H381 . 118.5 no C39 . C38 . H381 . 118.4 no C38 . C39 . C40 . 120.7(8) yes C38 . C39 . H391 . 119.6 no C40 . C39 . H391 . 119.7 no C39 . C40 . C41 . 120.7(8) yes C39 . C40 . H401 . 119.8 no C41 . C40 . H401 . 119.5 no C36 . C41 . C40 . 121.3(7) yes C36 . C41 . C42 . 116.3(7) yes C40 . C41 . C42 . 122.4(7) yes C41 . C42 . C43 . 121.5(8) yes C41 . C42 . H421 . 119.8 no C43 . C42 . H421 . 118.7 no C42 . C43 . C44 . 118.9(7) yes C42 . C43 . H431 . 120.1 no C44 . C43 . H431 . 120.9 no C43 . C44 . C35 . 124.7(7) yes C43 . C44 . H441 . 117.9 no C35 . C44 . H441 . 117.4 no C5 . C45 . H453 . 110.4 no C5 . C45 . H451 . 109.6 no H453 . C45 . H451 . 109.4 no C5 . C45 . H452 . 109.9 no H453 . C45 . H452 . 110.0 no H451 . C45 . H452 . 107.5 no C16 . C46 . H461 . 109.9 no C16 . C46 . H463 . 109.2 no H461 . C46 . H463 . 109.5 no C16 . C46 . H462 . 109.6 no H461 . C46 . H462 . 110.0 no H463 . C46 . H462 . 108.5 no N13 . Zn1 . N6 . 87.14(19) yes N13 . Zn1 . N17 . 99.60(18) yes N6 . Zn1 . N17 . 104.88(17) yes N13 . Zn1 . Cl1 . 120.14(13) yes N6 . Zn1 . Cl1 . 120.51(14) yes N17 . Zn1 . Cl1 . 118.71(12) yes