Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_CRYSTALS_cif _audit_creation_date 05-05-02 _audit_creation_method CRYSTALS_ver_12.50 _oxford_structure_analysis_title 'THIS IS THE DEFAULT SETTING FOR THE TITLE, P' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 14.7325(4) _cell_length_b 15.2366(2) _cell_length_c 19.0213(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4269.77(15) _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 2 ' _symmetry_space_group_name_Hall '?' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,-y+1/2,-z' '-x+1/2,y+1/2,-z' '-x,-y,z' 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 Cu -1.9646 0.5888 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.3639 0.7018 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' O 0.0492 0.0322 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' N 0.0311 0.0180 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' C 0.0181 0.0091 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' _cell_formula_units_Z 2 # Given Formula = C93 H82 Cl4 Cu2 N4 O8 # Dc = 1.29 Fooo = 1716.00 Mu = 22.22 M = 826.30 # Found Formula = C93 H82 Cl4 Cu2 N4 O8 # Dc = 1.29 FOOO = 1716.00 Mu = 22.22 M = 826.30 _chemical_formula_sum 'C93 H82 Cl4 Cu2 N4 O8' _chemical_formula_moiety 'C93 H82 Cl4 Cu2 N4 O8' _chemical_compound_source ? _chemical_formula_weight 1652.60 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description 'block' _exptl_crystal_colour 'red' _exptl_crystal_size_min 0.17 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.94 _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1716 _exptl_absorpt_coefficient_mu 2.222 # Sheldrick geometric approximatio 0.41 0.69 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.69 _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.1500 _diffrn_source_power 1.9320 _diffrn_source_voltage 46.0000 _diffrn_source_current 42.0000 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Copper' _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector 'RX' _diffrn_measurement_device ; RAXIS conversion ; _diffrn_detector_area_resol_mean 10.0000 _diffrn_measurement_method 'dtprofit.ref' _diffrn_reflns_number 28850 _diffrn_number_total 28850 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/detI 0.1042 _diffrn_reflns_theta_full 72.1250 _diffrn_measured_fraction_theta_max 72.1250 _diffrn_measured_fraction_theta_full 84.0000 _diffrn_reflns_theta_min 2.3229 _diffrn_reflns_theta_max 72.1250 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 18 Slice: 0.0000 - 180.0000 Image width: 10.0000 Exp time: 750.0000 Rotation axis: Omega Omega: 0.0000 Chi: 0.0000 Phi: 0.0000 XTD: 127.4000 2theta: -0.0195 scan: Number of images: 18 Slice: 0.0000 - 180.0000 Image width: 10.0000 Exp time: 750.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 127.4000 2theta: -0.0195 scan: Number of images: 18 Slice: 0.0000 - 180.0000 Image width: 10.0000 Exp time: 750.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 127.4000 2theta: -0.0195 ; _diffrn_measurement_device_details ; Crystal Goniometer ; _diffrn_orient_matrix_UB_11 -0.0667 _diffrn_orient_matrix_UB_12 -0.0037 _diffrn_orient_matrix_UB_13 -0.0122 _diffrn_orient_matrix_UB_21 0.0110 _diffrn_orient_matrix_UB_22 0.0109 _diffrn_orient_matrix_UB_23 -0.0638 _diffrn_orient_matrix_UB_31 0.0043 _diffrn_orient_matrix_UB_32 -0.0518 _diffrn_orient_matrix_UB_33 -0.0081 _diffrn_orient_matrix_type 'd*Trek' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? # Number of reflections with Friedels Law is 4566 # Number of reflections without Friedels Law is 6828 # Theoretical number of reflections is about 4187 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _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 -0.41 _refine_diff_density_max 1.08 _refine_ls_number_reflns 4566 _refine_ls_number_restraints 0 _refine_ls_number_parameters 504 #_refine_ls_R_factor_ref 0.0532 _refine_ls_wR_factor_ref 0.0750 _refine_ls_goodness_of_fit_ref 0.6013 #_reflns_number_all 6796 _refine_ls_R_factor_all 0.0658 _refine_ls_wR_factor_all 0.1033 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.50u(I) _reflns_number_gt 4566 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_gt 0.0750 _refine_ls_shift/su_max 0.001111 _refine_ls_abs_structure_Flack 0.03(13) _refine_ls_abs_structure_details 'Flack, 2262 Friedel-pairs' # 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 'ad' _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) w=1/[sigma^2^(F^2^) + 0.10 + 0.00p] ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. # 1. SUBMISSION DETAILS _publ_contact_author_name 'P. Wilson' _publ_contact_author_address ; Chemistry Department Simon Fraser University 8888 University Drive Burnaby, BC Canada, V5A 1S6 ; _publ_contact_author_phone '604-291-5654' _publ_contact_author_fax '604-291-3765' _publ_contact_author_email 'pwilson@sfu.ca' _publ_requested_journal ? _publ_requested_coeditor_name ? _publ_contact_letter ; To accompany manuscript ; #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? # Title of paper ; # 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_address 'Lyle, Mike' ; Department of Chemistry Simon Fraser University Burnaby, BC Canada, V5A 1S6 ; 'Draper, Neil D.' ; Department of Chemistry Simon Fraser University Burnaby, BC Canada, V5A 1S6 ; 'Wilson, Peter ' ; Department of Chemistry Simon Fraser University Burnaby, BC Canada, V5A 1S6 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; ? ; _publ_section_comment #Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Gabe, E. J.; Lepage, Y.; Charland, J. P.; Lee, F. L.; White, P. S. J. Appl. Cryst. 1989, 22, 384-387. International tables for X-ray crystallography, Vol. IV, Kynoch Press: Birmingham, Eng., 1974. Johnson, C. K.; (1976) ORTEP - A Fortran THermal Ellipsoid Plot Program, Technical Report ORNL-5138, Oak Ridge National Lab., U.S.A. Le Page, Y.; (1998) J. Appl. Cryst., 21, 983-984. Le Page, Y.; GBE, E. J.; (1979) J. Appl. Cryst., 12, 464-466. # CRYSTALS # Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I.; CRYSTALS Issue 11.67, Chemical Crystallography Laboratory, University of Oxford, Oxford, 2001 #Extinction correction # De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. #CAMERON # Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. #ORTEP-3 version 1.076 # Farrugia, L. J.; J. Appl. Cryst. 1997, 30, 565. #SIR92 # Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 #SHELXS 97 # Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. ; #**************************************************************************** # General computing #============================================================= _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _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)' # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 Cu1 Cu -1.0000 -0.5000 -0.74787(4) 0.0504 1.0000 Uani S T . . . . Cu2 Cu -1.5000 -0.5000 -0.76716(8) 0.1386 1.0000 Uani S T . . . . Cl1 Cl -1.4990(2) -0.3648(3) -0.76428(13) 0.1615 1.0000 Uani . . . . . . O1 O -1.0381(3) -0.7195(2) -0.86114(17) 0.0593 1.0000 Uani . . . . . . O2 O -1.0694(3) -0.5825(2) -0.90075(17) 0.0613 1.0000 Uani . . . . . . O3 O -1.0397(2) -0.4058(2) -0.59490(16) 0.0543 1.0000 Uani . . . . . . O4 O -0.9617(2) -0.2825(2) -0.62182(17) 0.0518 1.0000 Uani . . . . . . N1 N -0.9054(3) -0.5703(2) -0.80400(16) 0.0447 1.0000 Uani . . . . . . N2 N -0.8869(3) -0.4603(2) -0.69351(16) 0.0436 1.0000 Uani . . . . . . C1 C -1.0541(4) -0.2552(3) -0.6092(2) 0.0498 1.0000 Uani . . . . . . C2 C -1.1043(4) -0.3416(3) -0.6187(2) 0.0528 1.0000 Uani . . . . . . C3 C -1.1556(4) -0.6226(3) -0.8818(3) 0.0522 1.0000 Uani . . . . . . C4 C -1.1324(4) -0.7206(3) -0.8795(2) 0.0588 1.0000 Uani . . . . . . C5 C -0.8787(4) -0.4146(3) -0.6328(2) 0.0479 1.0000 Uani . . . . . . C6 C -0.9538(4) -0.3690(3) -0.5926(2) 0.0456 1.0000 Uani . . . . . . C7 C -0.9148(4) -0.3654(4) -0.5184(2) 0.0639 1.0000 Uani . . . . . . C8 C -0.8123(4) -0.3587(4) -0.5281(2) 0.0575 1.0000 Uani . . . . . . C9 C -0.7980(4) -0.4029(3) -0.5974(2) 0.0505 1.0000 Uani . . . . . . C10 C -0.7165(4) -0.4310(3) -0.6280(2) 0.0562 1.0000 Uani . . . . . . C11 C -0.7244(4) -0.4797(3) -0.6898(2) 0.0564 1.0000 Uani . . . . . . C12 C -0.8096(3) -0.4960(3) -0.71947(19) 0.0436 1.0000 Uani . . . . . . C13 C -0.8201(4) -0.5533(3) -0.7818(2) 0.0471 1.0000 Uani . . . . . . C14 C -0.7439(4) -0.5890(3) -0.8155(2) 0.0562 1.0000 Uani . . . . . . C15 C -0.7527(4) -0.6406(3) -0.8752(3) 0.0564 1.0000 Uani . . . . . . C16 C -0.8408(4) -0.6547(4) -0.8990(2) 0.0622 1.0000 Uani . . . . . . C17 C -0.8719(5) -0.7039(4) -0.9627(3) 0.0772 1.0000 Uani . . . . . . C18 C -0.9695(5) -0.6718(4) -0.9720(3) 0.0769 1.0000 Uani . . . . . . C19 C -1.0014(4) -0.6468(3) -0.8980(2) 0.0527 1.0000 Uani . . . . . . C20 C -0.9132(4) -0.6192(3) -0.8625(2) 0.0500 1.0000 Uani . . . . . . C21 C -0.6252(5) -0.4119(5) -0.5955(3) 0.0821 1.0000 Uani . . . . . . C22 C -0.6701(5) -0.6755(5) -0.9135(4) 0.0939 1.0000 Uani . . . . . . C23 C -1.0785(4) -0.1816(3) -0.6576(2) 0.0578 1.0000 Uani . . . . . . C24 C -1.1037(5) -0.1012(4) -0.6337(3) 0.0868 1.0000 Uani . . . . . . C25 C -1.1216(7) -0.0334(5) -0.6787(4) 0.1213 1.0000 Uani . . . . . . C26 C -1.1185(5) -0.0464(5) -0.7491(4) 0.0995 1.0000 Uani . . . . . . C27 C -1.0920(5) -0.1243(5) -0.7749(3) 0.0950 1.0000 Uani . . . . . . C28 C -1.0721(5) -0.1929(4) -0.7297(3) 0.0836 1.0000 Uani . . . . . . C29 C -1.1927(4) -0.3509(3) -0.5795(3) 0.0614 1.0000 Uani . . . . . . C30 C -1.2741(5) -0.3279(4) -0.6134(4) 0.0802 1.0000 Uani . . . . . . C31 C -1.3551(6) -0.3402(5) -0.5775(6) 0.1098 1.0000 Uani . . . . . . C32 C -1.3550(9) -0.3736(6) -0.5123(7) 0.1232 1.0000 Uani . . . . . . C33 C -1.2777(8) -0.3958(5) -0.4796(5) 0.1094 1.0000 Uani . . . . . . C34 C -1.1962(5) -0.3859(4) -0.5133(3) 0.0760 1.0000 Uani . . . . . . C35 C -1.2313(4) -0.5953(3) -0.9303(3) 0.0606 1.0000 Uani . . . . . . C36 C -1.2136(5) -0.5690(4) -0.9990(3) 0.0710 1.0000 Uani . . . . . . C37 C -1.2844(6) -0.5472(5) -1.0418(4) 0.0921 1.0000 Uani . . . . . . C38 C -1.3726(6) -0.5498(5) -1.0187(4) 0.0911 1.0000 Uani . . . . . . C39 C -1.3900(6) -0.5756(5) -0.9532(4) 0.0927 1.0000 Uani . . . . . . C40 C -1.3200(5) -0.5991(4) -0.9075(3) 0.0717 1.0000 Uani . . . . . . C41 C -1.1869(4) -0.7712(3) -0.8270(3) 0.0604 1.0000 Uani . . . . . . C42 C -1.2522(6) -0.8311(5) -0.8497(4) 0.0979 1.0000 Uani . . . . . . C43 C -1.3089(6) -0.8702(6) -0.7996(5) 0.1205 1.0000 Uani . . . . . . C44 C -1.2974(6) -0.8566(5) -0.7308(5) 0.1054 1.0000 Uani . . . . . . C45 C -1.2307(6) -0.8003(4) -0.7077(4) 0.0898 1.0000 Uani . . . . . . C46 C -1.1760(5) -0.7582(4) -0.7552(3) 0.0799 1.0000 Uani . . . . . . Cl5 Cl 0.4148(5) 0.1049(4) 0.1749(3) 0.158(2) 0.5000 Uiso . . . . . . Cl6 Cl 0.4107(6) 0.0982(6) 0.3254(4) 0.201(3) 0.5000 Uiso . . . . . . C47 C 0.3545(16) 0.1399(16) 0.2415(12) 0.152(8) 0.5000 Uiso . . . . . . H11 H -1.0600 -0.2360 -0.5619 0.060 1.0000 Uiso . . . . . . H21 H -1.1153 -0.3507 -0.6674 0.063 1.0000 Uiso . . . . . . H31 H -1.1705 -0.6042 -0.8355 0.063 1.0000 Uiso . . . . . . H41 H -1.1397 -0.7454 -0.9250 0.071 1.0000 Uiso . . . . . . H71 H -0.9300 -0.4166 -0.4924 0.089 1.0000 Uiso . . . . . . H72 H -0.9364 -0.3150 -0.4942 0.089 1.0000 Uiso . . . . . . H81 H -0.7929 -0.2993 -0.5303 0.084 1.0000 Uiso . . . . . . H82 H -0.7805 -0.3881 -0.4915 0.084 1.0000 Uiso . . . . . . H111 H -0.6713 -0.5021 -0.7117 0.079 1.0000 Uiso . . . . . . H141 H -0.6853 -0.5768 -0.7971 0.075 1.0000 Uiso . . . . . . H171 H -0.8695 -0.7654 -0.9546 0.108 1.0000 Uiso . . . . . . H172 H -0.8358 -0.6896 -1.0024 0.108 1.0000 Uiso . . . . . . H181 H -1.0063 -0.7176 -0.9903 0.103 1.0000 Uiso . . . . . . H182 H -0.9717 -0.6227 -1.0028 0.103 1.0000 Uiso . . . . . . H211 H -0.5788 -0.4363 -0.6242 0.109 1.0000 Uiso . . . . . . H212 H -0.6226 -0.4375 -0.5500 0.109 1.0000 Uiso . . . . . . H213 H -0.6166 -0.3503 -0.5918 0.109 1.0000 Uiso . . . . . . H221 H -0.6883 -0.7100 -0.9526 0.128 1.0000 Uiso . . . . . . H222 H -0.6350 -0.6271 -0.9294 0.128 1.0000 Uiso . . . . . . H223 H -0.6347 -0.7103 -0.8824 0.128 1.0000 Uiso . . . . . . H241 H -1.1051 -0.0911 -0.5844 0.107 1.0000 Uiso . . . . . . H251 H -1.1404 0.0215 -0.6601 0.140 1.0000 Uiso . . . . . . H261 H -1.1336 0.0000 -0.7804 0.118 1.0000 Uiso . . . . . . H271 H -1.0873 -0.1334 -0.8242 0.125 1.0000 Uiso . . . . . . H281 H -1.0532 -0.2481 -0.7477 0.110 1.0000 Uiso . . . . . . H301 H -1.2722 -0.3054 -0.6600 0.101 1.0000 Uiso . . . . . . H311 H -1.4103 -0.3240 -0.5998 0.129 1.0000 Uiso . . . . . . H321 H -1.4120 -0.3818 -0.4898 0.132 1.0000 Uiso . . . . . . H331 H -1.2820 -0.4176 -0.4329 0.118 1.0000 Uiso . . . . . . H341 H -1.1423 -0.4044 -0.4902 0.087 1.0000 Uiso . . . . . . H361 H -1.1530 -0.5678 -1.0162 0.085 1.0000 Uiso . . . . . . H371 H -1.2725 -0.5286 -1.0886 0.109 1.0000 Uiso . . . . . . H381 H -1.4211 -0.5335 -1.0489 0.120 1.0000 Uiso . . . . . . H391 H -1.4511 -0.5787 -0.9374 0.118 1.0000 Uiso . . . . . . H401 H -1.3330 -0.6168 -0.8606 0.086 1.0000 Uiso . . . . . . H421 H -1.2601 -0.8411 -0.8987 0.104 1.0000 Uiso . . . . . . H431 H -1.3514 -0.9129 -0.8154 0.144 1.0000 Uiso . . . . . . H441 H -1.3394 -0.8821 -0.6989 0.122 1.0000 Uiso . . . . . . H451 H -1.2207 -0.7920 -0.6588 0.104 1.0000 Uiso . . . . . . H461 H -1.1308 -0.7182 -0.7396 0.092 1.0000 Uiso . . . . . . H471 H 0.3522 0.2022 0.2410 0.12 0.5000 Uiso . . . . . . H472 H 0.2948 0.1170 0.2379 0.12 0.5000 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 Cu1 0.0423(6) 0.0644(5) 0.0445(4) 0.0000 0.0000 0.0022(4) Cu2 0.0638(12) 0.256(3) 0.0961(10) 0.0000 0.0000 -0.0286(14) Cl1 0.1062(19) 0.246(3) 0.1326(17) 0.0230(19) 0.0126(18) -0.024(2) O1 0.068(3) 0.0538(19) 0.0563(18) -0.0006(14) -0.0100(15) -0.0010(17) O2 0.061(3) 0.062(2) 0.061(2) -0.0001(15) -0.0151(16) -0.0023(18) O3 0.052(3) 0.0498(17) 0.0609(19) -0.0036(14) 0.0036(14) 0.0014(17) O4 0.052(3) 0.0475(17) 0.0564(18) -0.0003(13) 0.0071(14) -0.0042(15) N1 0.051(3) 0.0480(19) 0.0355(17) -0.0001(13) 0.0022(16) -0.0001(17) N2 0.050(3) 0.0432(18) 0.0373(17) 0.0026(14) -0.0009(15) -0.0046(17) C1 0.050(4) 0.053(2) 0.047(2) -0.0036(18) 0.005(2) -0.002(2) C2 0.056(4) 0.056(3) 0.047(2) -0.008(2) 0.001(2) -0.001(2) C3 0.049(4) 0.060(3) 0.048(2) -0.006(2) -0.006(2) -0.004(2) C4 0.069(4) 0.057(3) 0.051(2) -0.004(2) -0.016(2) -0.004(2) C5 0.052(4) 0.048(2) 0.044(2) -0.0012(18) -0.0062(19) -0.001(2) C6 0.037(4) 0.054(3) 0.046(2) -0.0018(18) 0.0038(19) -0.002(2) C7 0.080(5) 0.069(3) 0.042(2) -0.007(2) 0.004(2) -0.009(3) C8 0.055(5) 0.066(3) 0.051(3) -0.010(2) -0.009(2) 0.002(3) C9 0.049(4) 0.053(3) 0.050(2) -0.001(2) -0.010(2) -0.007(2) C10 0.053(4) 0.062(3) 0.054(3) 0.004(2) -0.006(2) -0.013(2) C11 0.050(4) 0.063(3) 0.056(3) 0.000(2) 0.001(2) 0.002(2) C12 0.042(3) 0.043(2) 0.0466(19) -0.0019(18) 0.0035(17) 0.001(2) C13 0.053(4) 0.045(2) 0.044(2) 0.0021(16) 0.003(2) 0.005(2) C14 0.050(4) 0.066(3) 0.052(3) -0.004(2) 0.010(2) 0.003(2) C15 0.055(4) 0.061(3) 0.053(3) -0.004(2) 0.006(2) 0.007(3) C16 0.077(5) 0.063(3) 0.047(3) -0.012(2) 0.007(2) 0.005(3) C17 0.086(6) 0.087(4) 0.058(3) -0.023(3) 0.008(3) -0.002(3) C18 0.091(6) 0.091(4) 0.049(3) -0.017(3) -0.001(2) -0.012(3) C19 0.052(4) 0.061(3) 0.045(2) -0.0045(17) -0.002(2) 0.002(3) C20 0.052(4) 0.058(3) 0.040(2) -0.0022(18) -0.0017(19) 0.001(2) C21 0.069(5) 0.103(5) 0.075(4) -0.005(3) -0.007(3) -0.010(4) C22 0.084(6) 0.106(5) 0.092(4) -0.037(4) 0.018(4) 0.009(4) C23 0.064(4) 0.059(3) 0.050(2) -0.004(2) 0.007(2) 0.009(2) C24 0.128(6) 0.067(3) 0.066(3) -0.003(3) 0.014(3) 0.024(4) C25 0.192(9) 0.080(4) 0.092(5) 0.007(4) 0.020(5) 0.059(5) C26 0.123(6) 0.096(4) 0.080(4) 0.022(4) 0.005(4) 0.037(4) C27 0.129(7) 0.098(5) 0.058(3) 0.006(3) 0.004(3) 0.023(5) C28 0.130(6) 0.070(3) 0.050(3) -0.001(2) 0.013(3) 0.024(4) C29 0.058(5) 0.058(3) 0.068(3) -0.015(2) 0.010(3) 0.004(3) C30 0.068(6) 0.070(4) 0.103(5) -0.029(3) 0.004(4) 0.003(3) C31 0.063(6) 0.084(5) 0.182(10) -0.053(6) 0.024(6) -0.002(4) C32 0.114(10) 0.087(6) 0.169(10) -0.027(6) 0.086(8) -0.015(5) C33 0.132(9) 0.080(5) 0.116(6) -0.010(4) 0.059(6) 0.000(5) C34 0.083(5) 0.073(4) 0.072(4) -0.007(3) 0.033(3) -0.003(3) C35 0.075(5) 0.051(3) 0.057(3) -0.009(2) -0.008(3) -0.002(3) C36 0.069(5) 0.085(4) 0.059(3) 0.005(3) -0.015(3) 0.001(3) C37 0.100(7) 0.100(5) 0.076(4) 0.007(3) -0.031(4) 0.006(4) C38 0.084(7) 0.089(5) 0.100(5) -0.008(4) -0.027(4) 0.029(4) C39 0.072(6) 0.092(5) 0.114(6) -0.017(4) -0.022(4) 0.009(4) C40 0.063(5) 0.080(4) 0.072(3) -0.015(3) 0.007(3) 0.000(3) C41 0.056(4) 0.054(3) 0.072(3) -0.001(2) -0.019(3) -0.004(2) C42 0.120(7) 0.091(4) 0.083(4) 0.010(3) -0.042(4) -0.038(4) C43 0.093(7) 0.122(7) 0.147(8) 0.036(6) -0.032(6) -0.056(5) C44 0.101(7) 0.104(5) 0.111(6) 0.021(4) 0.008(4) -0.031(5) C45 0.117(6) 0.079(4) 0.073(4) 0.011(3) 0.003(4) -0.009(4) C46 0.111(5) 0.068(3) 0.061(3) -0.002(3) -0.009(3) -0.021(3) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 2.663(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 Cu1 . N1 4_345 2.057(4) yes Cu1 . N2 4_345 2.052(4) yes Cu1 . C13 4_345 2.846(5) yes Cu1 . N1 . 2.057(4) yes Cu1 . N2 . 2.052(4) yes Cu1 . C13 . 2.846(5) yes Cu2 . Cl1 4_245 2.060(4) yes Cu2 . Cl1 . 2.060(4) yes O1 . C4 . 1.433(6) yes O1 . C19 . 1.418(6) yes O2 . C3 . 1.453(6) yes O2 . C19 . 1.402(6) yes O3 . C2 . 1.438(6) yes O3 . C6 . 1.384(6) yes O4 . C1 . 1.443(6) yes O4 . C6 . 1.435(6) yes N1 . C13 . 1.351(6) yes N1 . C20 . 1.344(6) yes N2 . C5 . 1.355(5) yes N2 . C12 . 1.355(6) yes C1 . C2 . 1.521(7) yes C1 . C23 . 1.494(7) yes C1 . H11 . 0.950 no C2 . C29 . 1.507(8) yes C2 . H21 . 0.950 no C3 . C4 . 1.533(7) yes C3 . C35 . 1.506(7) yes C3 . H31 . 0.950 no C4 . C41 . 1.495(8) yes C4 . H41 . 0.950 no C5 . C6 . 1.514(7) yes C5 . C9 . 1.378(7) yes C6 . C7 . 1.526(6) yes C7 . C8 . 1.525(8) yes C7 . H71 . 0.950 no C7 . H72 . 0.950 no C8 . C9 . 1.495(7) yes C8 . H81 . 0.950 no C8 . H82 . 0.950 no C9 . C10 . 1.402(8) yes C10 . C11 . 1.395(7) yes C10 . C21 . 1.508(8) yes C11 . C12 . 1.398(7) yes C11 . H111 . 0.950 no C12 . C13 . 1.480(6) yes C13 . C14 . 1.402(7) yes C14 . C15 . 1.388(7) yes C14 . H141 . 0.950 no C15 . C16 . 1.391(8) yes C15 . C22 . 1.514(8) yes C16 . C17 . 1.495(7) yes C16 . C20 . 1.383(7) yes C17 . C18 . 1.529(9) yes C17 . H171 . 0.950 no C17 . H172 . 0.950 no C18 . C19 . 1.532(6) yes C18 . H181 . 0.950 no C18 . H182 . 0.950 no C19 . C20 . 1.522(7) yes C21 . H211 . 0.950 no C21 . H212 . 0.950 no C21 . H213 . 0.950 no C22 . H221 . 0.950 no C22 . H222 . 0.950 no C22 . H223 . 0.950 no C23 . C24 . 1.359(8) yes C23 . C28 . 1.386(7) yes C24 . C25 . 1.368(9) yes C24 . H241 . 0.950 no C25 . C26 . 1.355(10) yes C25 . H251 . 0.950 no C26 . C27 . 1.342(9) yes C26 . H261 . 0.950 no C27 . C28 . 1.384(8) yes C27 . H271 . 0.950 no C28 . H281 . 0.950 no C29 . C30 . 1.407(9) yes C29 . C34 . 1.368(8) yes C30 . C31 . 1.388(11) yes C30 . H301 . 0.950 no C31 . C32 . 1.341(14) yes C31 . H311 . 0.950 no C32 . C33 . 1.342(14) yes C32 . H321 . 0.950 no C33 . C34 . 1.370(11) yes C33 . H331 . 0.950 no C34 . H341 . 0.950 no C35 . C36 . 1.391(8) yes C35 . C40 . 1.379(8) yes C36 . C37 . 1.365(9) yes C36 . H361 . 0.950 no C37 . C38 . 1.372(11) yes C37 . H371 . 0.950 no C38 . C39 . 1.332(10) yes C38 . H381 . 0.950 no C39 . C40 . 1.395(9) yes C39 . H391 . 0.950 no C40 . H401 . 0.950 no C41 . C42 . 1.395(8) yes C41 . C46 . 1.389(8) yes C42 . C43 . 1.401(11) yes C42 . H421 . 0.950 no C43 . C44 . 1.336(11) yes C43 . H431 . 0.950 no C44 . C45 . 1.376(10) yes C44 . H441 . 0.950 no C45 . C46 . 1.372(9) yes C45 . H451 . 0.950 no C46 . H461 . 0.950 no Cl5 . C47 . 1.64(2) yes Cl6 . C47 . 1.91(2) yes C47 . H471 . 0.950 no C47 . H472 . 0.950 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 N1 4_345 Cu1 . N2 4_345 82.23(15) yes N1 4_345 Cu1 . C13 4_345 26.20(14) yes N2 4_345 Cu1 . C13 4_345 56.08(14) yes N1 4_345 Cu1 . N1 . 117.46(19) yes N2 4_345 Cu1 . N1 . 131.17(14) yes C13 4_345 Cu1 . N1 . 131.46(14) yes N1 4_345 Cu1 . N2 . 131.17(14) yes N2 4_345 Cu1 . N2 . 119.49(19) yes C13 4_345 Cu1 . N2 . 141.85(13) yes N1 . Cu1 . N2 . 82.23(15) yes N1 4_345 Cu1 . C13 . 131.46(14) yes N2 4_345 Cu1 . C13 . 141.85(13) yes C13 4_345 Cu1 . C13 . 153.81(17) yes N1 . Cu1 . C13 . 26.20(14) yes N2 . Cu1 . C13 . 56.08(14) yes Cl1 4_245 Cu2 . Cl1 . 176.95(17) yes C4 . O1 . C19 . 105.0(4) yes C3 . O2 . C19 . 108.8(4) yes C2 . O3 . C6 . 109.8(4) yes C1 . O4 . C6 . 106.1(3) yes Cu1 . N1 . C13 . 111.6(3) yes Cu1 . N1 . C20 . 131.3(3) yes C13 . N1 . C20 . 116.5(4) yes Cu1 . N2 . C5 . 130.8(3) yes Cu1 . N2 . C12 . 112.4(3) yes C5 . N2 . C12 . 116.2(4) yes O4 . C1 . C2 . 100.9(4) yes O4 . C1 . C23 . 109.9(4) yes C2 . C1 . C23 . 117.3(4) yes O4 . C1 . H11 . 109.4 no C2 . C1 . H11 . 109.5 no C23 . C1 . H11 . 109.4 no C1 . C2 . O3 . 103.3(4) yes C1 . C2 . C29 . 116.3(4) yes O3 . C2 . C29 . 110.6(4) yes C1 . C2 . H21 . 109.0 no O3 . C2 . H21 . 108.7 no C29 . C2 . H21 . 108.7 no O2 . C3 . C4 . 102.8(4) yes O2 . C3 . C35 . 112.3(4) yes C4 . C3 . C35 . 116.8(4) yes O2 . C3 . H31 . 108.0 no C4 . C3 . H31 . 108.2 no C35 . C3 . H31 . 108.4 no C3 . C4 . O1 . 102.2(4) yes C3 . C4 . C41 . 113.7(5) yes O1 . C4 . C41 . 111.4(4) yes C3 . C4 . H41 . 109.7 no O1 . C4 . H41 . 109.6 no C41 . C4 . H41 . 110.0 no N2 . C5 . C6 . 127.0(4) yes N2 . C5 . C9 . 124.0(4) yes C6 . C5 . C9 . 109.0(4) yes C5 . C6 . O4 . 106.6(4) yes C5 . C6 . O3 . 117.8(4) yes O4 . C6 . O3 . 106.6(4) yes C5 . C6 . C7 . 102.0(4) yes O4 . C6 . C7 . 110.9(4) yes O3 . C6 . C7 . 112.8(4) yes C6 . C7 . C8 . 105.3(4) yes C6 . C7 . H71 . 111.3 no C8 . C7 . H71 . 110.6 no C6 . C7 . H72 . 110.4 no C8 . C7 . H72 . 109.7 no H71 . C7 . H72 . 109.466 no C7 . C8 . C9 . 102.5(4) yes C7 . C8 . H81 . 111.4 no C9 . C8 . H81 . 110.4 no C7 . C8 . H82 . 111.6 no C9 . C8 . H82 . 111.4 no H81 . C8 . H82 . 109.467 no C8 . C9 . C5 . 111.5(5) yes C8 . C9 . C10 . 128.6(5) yes C5 . C9 . C10 . 119.8(4) yes C9 . C10 . C11 . 116.1(5) yes C9 . C10 . C21 . 122.3(5) yes C11 . C10 . C21 . 121.6(5) yes C10 . C11 . C12 . 120.7(5) yes C10 . C11 . H111 . 119.5 no C12 . C11 . H111 . 119.9 no C11 . C12 . N2 . 122.4(4) yes C11 . C12 . C13 . 121.5(4) yes N2 . C12 . C13 . 116.1(4) yes C12 . C13 . N1 . 117.5(4) yes C12 . C13 . Cu1 . 75.4(3) yes N1 . C13 . Cu1 . 42.2(2) yes C12 . C13 . C14 . 120.7(4) yes N1 . C13 . C14 . 121.8(4) yes Cu1 . C13 . C14 . 163.7(4) yes C13 . C14 . C15 . 121.3(5) yes C13 . C14 . H141 . 118.9 no C15 . C14 . H141 . 119.7 no C14 . C15 . C16 . 116.1(5) yes C14 . C15 . C22 . 121.2(6) yes C16 . C15 . C22 . 122.6(5) yes C15 . C16 . C17 . 128.8(5) yes C15 . C16 . C20 . 119.8(4) yes C17 . C16 . C20 . 111.5(5) yes C16 . C17 . C18 . 102.8(5) yes C16 . C17 . H171 . 110.7 no C18 . C17 . H171 . 111.6 no C16 . C17 . H172 . 111.0 no C18 . C17 . H172 . 111.1 no H171 . C17 . H172 . 109.467 no C17 . C18 . C19 . 105.1(5) yes C17 . C18 . H181 . 110.2 no C19 . C18 . H181 . 110.1 no C17 . C18 . H182 . 110.8 no C19 . C18 . H182 . 111.0 no H181 . C18 . H182 . 109.467 no C18 . C19 . O1 . 112.2(4) yes C18 . C19 . O2 . 111.0(4) yes O1 . C19 . O2 . 106.9(4) yes C18 . C19 . C20 . 102.4(5) yes O1 . C19 . C20 . 108.7(4) yes O2 . C19 . C20 . 115.7(4) yes C19 . C20 . C16 . 109.1(4) yes C19 . C20 . N1 . 126.4(4) yes C16 . C20 . N1 . 124.5(5) yes C10 . C21 . H211 . 109.2 no C10 . C21 . H212 . 109.3 no H211 . C21 . H212 . 109.476 no C10 . C21 . H213 . 109.9 no H211 . C21 . H213 . 109.475 no H212 . C21 . H213 . 109.476 no C15 . C22 . H221 . 110.1 no C15 . C22 . H222 . 108.6 no H221 . C22 . H222 . 109.476 no C15 . C22 . H223 . 109.7 no H221 . C22 . H223 . 109.475 no H222 . C22 . H223 . 109.476 no C1 . C23 . C24 . 122.4(5) yes C1 . C23 . C28 . 120.0(4) yes C24 . C23 . C28 . 117.5(5) yes C23 . C24 . C25 . 121.6(6) yes C23 . C24 . H241 . 118.8 no C25 . C24 . H241 . 119.4 no C24 . C25 . C26 . 120.1(6) yes C24 . C25 . H251 . 119.2 no C26 . C25 . H251 . 120.5 no C25 . C26 . C27 . 120.0(6) yes C25 . C26 . H261 . 120.1 no C27 . C26 . H261 . 119.9 no C26 . C27 . C28 . 120.2(6) yes C26 . C27 . H271 . 120.7 no C28 . C27 . H271 . 119.1 no C23 . C28 . C27 . 120.4(5) yes C23 . C28 . H281 . 119.1 no C27 . C28 . H281 . 120.4 no C2 . C29 . C30 . 119.1(5) yes C2 . C29 . C34 . 121.7(6) yes C30 . C29 . C34 . 119.2(6) yes C29 . C30 . C31 . 118.3(7) yes C29 . C30 . H301 . 119.6 no C31 . C30 . H301 . 122.1 no C30 . C31 . C32 . 120.4(9) yes C30 . C31 . H311 . 118.8 no C32 . C31 . H311 . 120.8 no C31 . C32 . C33 . 121.7(9) yes C31 . C32 . H321 . 117.7 no C33 . C32 . H321 . 120.6 no C32 . C33 . C34 . 120.0(9) yes C32 . C33 . H331 . 117.7 no C34 . C33 . H331 . 122.3 no C33 . C34 . C29 . 120.5(8) yes C33 . C34 . H341 . 118.8 no C29 . C34 . H341 . 120.7 no C3 . C35 . C36 . 121.1(5) yes C3 . C35 . C40 . 119.8(5) yes C36 . C35 . C40 . 119.1(5) yes C35 . C36 . C37 . 119.2(7) yes C35 . C36 . H361 . 120.4 no C37 . C36 . H361 . 120.5 no C36 . C37 . C38 . 121.7(7) yes C36 . C37 . H371 . 119.4 no C38 . C37 . H371 . 118.9 no C37 . C38 . C39 . 119.4(6) yes C37 . C38 . H381 . 120.7 no C39 . C38 . H381 . 119.9 no C38 . C39 . C40 . 121.1(7) yes C38 . C39 . H391 . 119.4 no C40 . C39 . H391 . 119.4 no C39 . C40 . C35 . 119.6(6) yes C39 . C40 . H401 . 120.6 no C35 . C40 . H401 . 119.9 no C4 . C41 . C42 . 120.1(5) yes C4 . C41 . C46 . 121.4(5) yes C42 . C41 . C46 . 118.5(6) yes C41 . C42 . C43 . 118.6(7) yes C41 . C42 . H421 . 119.5 no C43 . C42 . H421 . 121.7 no C42 . C43 . C44 . 121.7(7) yes C42 . C43 . H431 . 118.0 no C44 . C43 . H431 . 119.9 no C43 . C44 . C45 . 120.1(7) yes C43 . C44 . H441 . 118.7 no C45 . C44 . H441 . 121.0 no C44 . C45 . C46 . 120.0(6) yes C44 . C45 . H451 . 120.4 no C46 . C45 . H451 . 119.5 no C41 . C46 . C45 . 120.9(6) yes C41 . C46 . H461 . 118.7 no C45 . C46 . H461 . 120.4 no Cl6 . C47 . Cl5 . 107.7(13) yes Cl6 . C47 . H471 . 110.9 no Cl5 . C47 . H471 . 109.8 no Cl6 . C47 . H472 . 109.9 no Cl5 . C47 . H472 . 109.1 no H471 . C47 . H472 . 109.467 no