# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Housecroft, Catherine' 'Constable, Edwin' 'Zampese, Jennifer' 'Zhang, Guoqi' 'Neuburger, Markus' 'Kopecky, Peter' _publ_contact_author_name 'Prof. Catherine Housecroft' _publ_contact_author_email Catherine.Housecroft@unibas.ch _publ_section_title ; Coordination polymers with divergent 4'-tert-butyl-4,2':6',4"-terpyridine linkers: from aryl-aryl to ball-and-socket packing ; # Attachment '- GQ267.CIF' data_gq267 _database_code_depnum_ccdc_archive 'CCDC 838857' #TrackingRef '- GQ267.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C40 H38 Co N8 S2), 4(C H4 O), H2 O' _chemical_formula_sum 'C164 H170 Co4 N32 O5 S8' _chemical_formula_weight 3161.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall C2y 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' _cell_length_a 27.298(4) _cell_length_b 10.7049(12) _cell_length_c 15.889(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.480(10) _cell_angle_gamma 90.00 _cell_volume 3916.8(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10247 _cell_measurement_theta_min 5.57 _cell_measurement_theta_max 57.70 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1652 _exptl_absorpt_coefficient_mu 0.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8431 _exptl_absorpt_correction_T_max 0.8913 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; The psuedo-inversion detected by addsym and checkcif is not a true inversion and C2 is the best spacegroup for this structure. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43488 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 29.00 _reflns_number_total 10372 _reflns_number_gt 10232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0527P)^2^+6.9956P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.471(11) _refine_ls_number_reflns 10372 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.002 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 Co1 Co 0.500669(12) -0.02601(3) -0.76141(2) 0.01880(7) Uani 1 1 d . . . N1 N 0.93906(9) 0.3503(2) -0.22538(16) 0.0223(4) Uani 1 1 d . . . N2 N 0.76614(8) 0.0996(2) -0.30230(14) 0.0201(4) Uani 1 1 d . . . N3 N 0.56896(8) 0.0143(2) -0.60128(15) 0.0212(4) Uani 1 1 d . . . C1 C 0.95611(11) 0.2713(3) -0.1498(2) 0.0354(7) Uani 1 1 d . . . H1A H 0.9961 0.2706 -0.0984 0.043 Uiso 1 1 calc R . . C2 C 0.91959(11) 0.1902(3) -0.1408(2) 0.0360(7) Uani 1 1 d . . . H2A H 0.9344 0.1365 -0.0847 0.043 Uiso 1 1 calc R . . C3 C 0.86072(10) 0.1887(2) -0.21573(17) 0.0208(4) Uani 1 1 d . . . C4 C 0.84225(10) 0.2747(3) -0.29199(18) 0.0250(5) Uani 1 1 d . . . H4A H 0.8022 0.2804 -0.3430 0.030 Uiso 1 1 calc R . . C5 C 0.88197(11) 0.3520(3) -0.29384(19) 0.0270(5) Uani 1 1 d . . . H5A H 0.8680 0.4102 -0.3471 0.032 Uiso 1 1 calc R . . C6 C 0.81757(10) 0.1029(2) -0.21620(16) 0.0189(4) Uani 1 1 d . . . C7 C 0.83017(10) 0.0314(2) -0.13381(17) 0.0211(4) Uani 1 1 d . . . H7A H 0.8671 0.0379 -0.0734 0.025 Uiso 1 1 calc R . . C8 C 0.78820(10) -0.0500(2) -0.14057(17) 0.0205(5) Uani 1 1 d . . . C9 C 0.73541(10) -0.0557(2) -0.23205(17) 0.0220(5) Uani 1 1 d . . . H9A H 0.7061 -0.1121 -0.2411 0.026 Uiso 1 1 calc R . . C10 C 0.72581(10) 0.0210(2) -0.30996(17) 0.0200(4) Uani 1 1 d . . . C11 C 0.57616(11) -0.0617(3) -0.52923(19) 0.0303(6) Uani 1 1 d . . . H11A H 0.5461 -0.1197 -0.5446 0.036 Uiso 1 1 calc R . . C12 C 0.62507(11) -0.0614(3) -0.43273(18) 0.0297(6) Uani 1 1 d . . . H12A H 0.6279 -0.1179 -0.3842 0.036 Uiso 1 1 calc R . . C13 C 0.66985(10) 0.0222(2) -0.40794(17) 0.0204(4) Uani 1 1 d . . . C14 C 0.66102(11) 0.1068(2) -0.48067(18) 0.0247(5) Uani 1 1 d . . . H14A H 0.6894 0.1688 -0.4662 0.030 Uiso 1 1 calc R . . C15 C 0.61086(11) 0.1005(2) -0.57423(19) 0.0251(5) Uani 1 1 d . . . H15A H 0.6055 0.1606 -0.6225 0.030 Uiso 1 1 calc R . . C16 C 0.79915(11) -0.1210(3) -0.04903(19) 0.0277(5) Uani 1 1 d . . . C17 C 0.85937(15) -0.1788(4) 0.0061(3) 0.0504(9) Uani 1 1 d . . . H17A H 0.8885 -0.1131 0.0249 0.076 Uiso 1 1 calc R . . H17B H 0.8621 -0.2396 -0.0372 0.076 Uiso 1 1 calc R . . H17C H 0.8663 -0.2209 0.0664 0.076 Uiso 1 1 calc R . . C18 C 0.7947(2) -0.0269(5) 0.0194(3) 0.0673(13) Uani 1 1 d . . . H18A H 0.8265 0.0337 0.0445 0.101 Uiso 1 1 calc R . . H18B H 0.7973 -0.0712 0.0756 0.101 Uiso 1 1 calc R . . H18C H 0.7574 0.0170 -0.0184 0.101 Uiso 1 1 calc R . . C19 C 0.7551(2) -0.2252(5) -0.0764(3) 0.0708(15) Uani 1 1 d . . . H19A H 0.7620 -0.2649 -0.0153 0.106 Uiso 1 1 calc R . . H19B H 0.7592 -0.2874 -0.1174 0.106 Uiso 1 1 calc R . . H19C H 0.7158 -0.1903 -0.1139 0.106 Uiso 1 1 calc R . . N4 N 0.43025(8) -0.0666(2) -0.91898(15) 0.0211(4) Uani 1 1 d . . . N5 N 0.22830(8) -0.1569(2) -1.19915(15) 0.0207(4) Uani 1 1 d . . . N6 N 0.05781(9) -0.3984(2) -1.25241(17) 0.0237(4) Uani 1 1 d . . . C20 C 0.39139(11) -0.1585(2) -0.94239(18) 0.0232(4) Uani 1 1 d . . . H20A H 0.4004 -0.2209 -0.8937 0.028 Uiso 1 1 calc R . . C21 C 0.33948(10) -0.1675(2) -1.03246(18) 0.0228(5) Uani 1 1 d . . . H21A H 0.3134 -0.2337 -1.0442 0.027 Uiso 1 1 calc R . . C22 C 0.32535(10) -0.0792(2) -1.10634(16) 0.0199(4) Uani 1 1 d . . . C23 C 0.36686(11) 0.0104(3) -1.08623(19) 0.0269(5) Uani 1 1 d . . . H23A H 0.3606 0.0686 -1.1362 0.032 Uiso 1 1 calc R . . C24 C 0.41782(10) 0.0145(3) -0.9922(2) 0.0268(5) Uani 1 1 d . . . H24A H 0.4453 0.0781 -0.9792 0.032 Uiso 1 1 calc R . . C25 C 0.26727(9) -0.0827(2) -1.20103(16) 0.0189(4) Uani 1 1 d . . . C26 C 0.25411(10) -0.0121(3) -1.28355(17) 0.0230(5) Uani 1 1 d . . . H26A H 0.2830 0.0396 -1.2815 0.028 Uiso 1 1 calc R . . C27 C 0.19865(9) -0.0163(3) -1.36965(15) 0.0221(4) Uani 1 1 d . . . C28 C 0.15807(10) -0.0914(3) -1.36591(18) 0.0241(5) Uani 1 1 d . . . H28A H 0.1194 -0.0962 -1.4220 0.029 Uiso 1 1 calc R . . C29 C 0.17418(10) -0.1587(2) -1.28050(17) 0.0205(4) Uani 1 1 d . . . C30 C 0.03896(11) -0.2943(3) -1.3076(2) 0.0348(7) Uani 1 1 d . . . H30A H -0.0010 -0.2739 -1.3393 0.042 Uiso 1 1 calc R . . C31 C 0.07402(11) -0.2141(3) -1.3215(2) 0.0361(7) Uani 1 1 d . . . H31A H 0.0580 -0.1432 -1.3636 0.043 Uiso 1 1 calc R . . C32 C 0.13311(10) -0.2402(2) -1.27219(18) 0.0218(4) Uani 1 1 d . . . C33 C 0.15345(10) -0.3451(3) -1.21208(18) 0.0228(5) Uani 1 1 d . . . H33A H 0.1937 -0.3645 -1.1754 0.027 Uiso 1 1 calc R . . C34 C 0.11476(10) -0.4218(3) -1.20572(19) 0.0243(5) Uani 1 1 d . . . H34A H 0.1294 -0.4951 -1.1660 0.029 Uiso 1 1 calc R . . C35 C 0.18535(11) 0.0538(3) -1.46268(19) 0.0286(5) Uani 1 1 d . . . C36 C 0.12031(14) 0.0725(5) -1.5351(3) 0.0593(12) Uani 1 1 d . . . H36A H 0.1011 -0.0090 -1.5565 0.089 Uiso 1 1 calc R . . H36B H 0.1135 0.1193 -1.5935 0.089 Uiso 1 1 calc R . . H36C H 0.1044 0.1193 -1.5020 0.089 Uiso 1 1 calc R . . C37 C 0.2090(2) -0.0208(5) -1.5140(3) 0.0595(10) Uani 1 1 d . . . H37A H 0.1917 -0.1044 -1.5297 0.089 Uiso 1 1 calc R . . H37B H 0.2513 -0.0279 -1.4697 0.089 Uiso 1 1 calc R . . H37C H 0.1995 0.0215 -1.5757 0.089 Uiso 1 1 calc R . . C38 C 0.2136(2) 0.1814(4) -1.4360(3) 0.0621(12) Uani 1 1 d . . . H38A H 0.2048 0.2248 -1.4970 0.093 Uiso 1 1 calc R . . H38B H 0.2558 0.1719 -1.3915 0.093 Uiso 1 1 calc R . . H38C H 0.1986 0.2301 -1.4024 0.093 Uiso 1 1 calc R . . N50 N 0.47005(10) -0.1691(2) -0.71580(16) 0.0255(4) Uani 1 1 d . . . C50 C 0.44187(12) -0.2380(3) -0.7035(2) 0.0271(5) Uani 1 1 d . . . S50 S 0.40007(5) -0.33675(9) -0.69191(8) 0.0471(2) Uani 1 1 d . . . N60 N 0.53084(10) 0.1204(2) -0.80442(17) 0.0269(4) Uani 1 1 d . . . C60 C 0.55705(15) 0.1986(3) -0.8127(3) 0.0347(6) Uani 1 1 d . . . S60 S 0.59763(8) 0.30631(12) -0.81710(16) 0.0944(6) Uani 1 1 d . . . O100 O 0.97328(16) 0.0121(4) 0.0866(3) 0.0834(12) Uani 1 1 d . . . H100 H 0.9979 -0.0337 0.0855 0.125 Uiso 1 1 calc R . . C100 C 0.9832(3) 0.0116(5) 0.1837(4) 0.0756(14) Uani 1 1 d . . . H10A H 1.0239 0.0328 0.2325 0.113 Uiso 1 1 calc R . . H10B H 0.9748 -0.0717 0.1985 0.113 Uiso 1 1 calc R . . H10C H 0.9579 0.0732 0.1874 0.113 Uiso 1 1 calc R . . O200 O 0.0000 0.0080(9) -1.5000 0.085(3) Uani 0.50 2 d SP . . 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 Co1 0.01140(11) 0.02084(13) 0.01889(13) -0.00005(13) 0.00465(9) 0.00027(10) N1 0.0158(9) 0.0241(10) 0.0232(9) 0.0011(8) 0.0079(8) -0.0005(7) N2 0.0150(8) 0.0265(10) 0.0169(8) -0.0027(7) 0.0073(7) -0.0022(7) N3 0.0166(8) 0.0261(9) 0.0186(9) -0.0035(7) 0.0079(7) 0.0003(7) C1 0.0139(10) 0.0445(17) 0.0297(13) 0.0119(12) -0.0004(10) -0.0039(10) C2 0.0194(12) 0.0430(17) 0.0296(13) 0.0058(12) 0.0025(10) -0.0089(11) C3 0.0171(10) 0.0233(11) 0.0172(9) -0.0025(8) 0.0060(8) -0.0033(8) C4 0.0155(10) 0.0332(13) 0.0217(10) 0.0051(9) 0.0071(8) -0.0009(9) C5 0.0196(11) 0.0340(13) 0.0226(11) 0.0068(10) 0.0081(9) -0.0022(9) C6 0.0172(9) 0.0231(11) 0.0158(9) -0.0011(8) 0.0085(8) -0.0007(8) C7 0.0177(10) 0.0260(11) 0.0167(10) 0.0025(8) 0.0073(8) 0.0017(9) C8 0.0207(10) 0.0218(13) 0.0185(9) 0.0017(7) 0.0102(8) 0.0011(8) C9 0.0183(9) 0.0278(13) 0.0195(10) -0.0016(8) 0.0099(8) -0.0027(8) C10 0.0161(9) 0.0273(10) 0.0151(9) -0.0039(8) 0.0075(8) -0.0033(8) C11 0.0205(11) 0.0412(16) 0.0240(11) -0.0016(10) 0.0085(9) -0.0118(10) C12 0.0262(12) 0.0412(15) 0.0175(10) 0.0008(9) 0.0090(9) -0.0132(10) C13 0.0142(9) 0.0264(11) 0.0185(10) -0.0032(8) 0.0074(8) -0.0011(8) C14 0.0193(10) 0.0256(12) 0.0217(11) 0.0004(9) 0.0060(9) -0.0042(9) C15 0.0207(11) 0.0223(11) 0.0228(11) 0.0015(9) 0.0053(9) -0.0017(9) C16 0.0267(12) 0.0334(13) 0.0245(11) 0.0088(10) 0.0146(10) 0.0020(10) C17 0.0403(17) 0.064(2) 0.0500(19) 0.0315(18) 0.0266(16) 0.0225(16) C18 0.126(4) 0.057(2) 0.055(2) 0.024(2) 0.072(3) 0.035(3) C19 0.065(3) 0.077(3) 0.046(2) 0.027(2) 0.0143(19) -0.030(2) N4 0.0139(8) 0.0257(9) 0.0196(9) -0.0008(7) 0.0064(7) 0.0005(7) N5 0.0161(8) 0.0253(10) 0.0196(9) -0.0003(7) 0.0088(7) 0.0003(7) N6 0.0155(9) 0.0259(10) 0.0244(10) 0.0026(8) 0.0071(8) -0.0005(8) C20 0.0229(11) 0.0233(11) 0.0184(10) 0.0022(8) 0.0079(9) 0.0008(9) C21 0.0208(10) 0.0252(12) 0.0187(10) -0.0018(9) 0.0082(9) -0.0043(9) C22 0.0151(9) 0.0270(11) 0.0162(9) -0.0017(8) 0.0074(8) 0.0012(8) C23 0.0195(10) 0.0342(13) 0.0192(10) 0.0029(8) 0.0053(9) -0.0030(9) C24 0.0159(10) 0.0312(12) 0.0256(11) 0.0021(9) 0.0061(9) -0.0049(9) C25 0.0146(9) 0.0262(11) 0.0135(9) -0.0005(8) 0.0059(8) 0.0009(8) C26 0.0189(9) 0.0288(13) 0.0214(9) 0.0012(10) 0.0107(8) -0.0020(9) C27 0.0193(9) 0.0285(12) 0.0169(8) 0.0005(10) 0.0086(7) -0.0022(10) C28 0.0176(10) 0.0295(13) 0.0212(10) 0.0003(9) 0.0077(9) -0.0020(9) C29 0.0143(9) 0.0253(11) 0.0204(10) -0.0016(8) 0.0083(8) -0.0014(8) C30 0.0141(10) 0.0303(14) 0.0467(17) 0.0157(12) 0.0075(11) 0.0015(10) C31 0.0142(11) 0.0311(14) 0.0484(17) 0.0157(12) 0.0070(11) 0.0009(10) C32 0.0147(10) 0.0274(12) 0.0204(10) 0.0000(9) 0.0076(8) 0.0003(8) C33 0.0134(9) 0.0293(12) 0.0231(10) 0.0015(9) 0.0082(8) 0.0007(9) C34 0.0169(10) 0.0274(12) 0.0244(11) 0.0037(9) 0.0083(9) 0.0003(9) C35 0.0246(12) 0.0379(14) 0.0196(11) 0.0073(10) 0.0095(9) -0.0003(10) C36 0.0288(15) 0.101(3) 0.0336(16) 0.0360(19) 0.0071(13) -0.0016(17) C37 0.094(3) 0.063(2) 0.0494(18) 0.022(2) 0.057(2) 0.022(3) C38 0.074(3) 0.0429(19) 0.0362(17) 0.0169(15) 0.0077(18) -0.0140(19) N50 0.0221(10) 0.0279(11) 0.0192(9) -0.0009(8) 0.0063(8) -0.0028(8) C50 0.0252(12) 0.0302(13) 0.0225(11) -0.0016(10) 0.0106(10) 0.0002(10) S50 0.0576(5) 0.0375(4) 0.0666(6) -0.0032(4) 0.0468(5) -0.0120(4) N60 0.0231(10) 0.0267(11) 0.0273(10) -0.0005(9) 0.0112(9) -0.0040(8) C60 0.0429(16) 0.0305(14) 0.0415(16) -0.0093(12) 0.0299(14) -0.0076(12) S60 0.1372(13) 0.0535(7) 0.1729(17) -0.0302(9) 0.1366(14) -0.0421(8) O100 0.072(2) 0.097(3) 0.0558(18) 0.0052(17) 0.0170(16) -0.0323(19) C100 0.084(3) 0.073(3) 0.066(3) -0.009(2) 0.039(3) -0.003(3) O200 0.087(7) 0.051(5) 0.077(6) 0.000 0.018(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Co1 N60 2.051(2) . ? Co1 N50 2.054(2) . ? Co1 N6 2.200(2) 4_553 ? Co1 N1 2.208(2) 4_644 ? Co1 N4 2.232(2) . ? Co1 N3 2.245(2) . ? N1 C1 1.331(4) . ? N1 C5 1.338(3) . ? N1 Co1 2.208(2) 4_654 ? N2 C6 1.335(3) . ? N2 C10 1.338(3) . ? N3 C11 1.331(4) . ? N3 C15 1.348(3) . ? C1 C2 1.387(4) . ? C1 H1A 0.9500 . ? C2 C3 1.394(3) . ? C2 H2A 0.9500 . ? C3 C4 1.384(3) . ? C3 C6 1.490(3) . ? C4 C5 1.377(3) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.391(3) . ? C7 C8 1.397(3) . ? C7 H7A 0.9500 . ? C8 C9 1.394(3) . ? C8 C16 1.522(3) . ? C9 C10 1.388(3) . ? C9 H9A 0.9500 . ? C10 C13 1.484(3) . ? C11 C12 1.391(3) . ? C11 H11A 0.9500 . ? C12 C13 1.390(3) . ? C12 H12A 0.9500 . ? C13 C14 1.383(4) . ? C14 C15 1.380(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.518(4) . ? C16 C19 1.522(5) . ? C16 C18 1.534(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N4 C24 1.341(3) . ? N4 C20 1.344(3) . ? N5 C25 1.341(3) . ? N5 C29 1.343(3) . ? N6 C34 1.338(3) . ? N6 C30 1.338(3) . ? N6 Co1 2.200(2) 4_543 ? C20 C21 1.374(3) . ? C20 H20A 0.9500 . ? C21 C22 1.391(3) . ? C21 H21A 0.9500 . ? C22 C23 1.385(3) . ? C22 C25 1.489(3) . ? C23 C24 1.392(3) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.383(3) . ? C26 C27 1.393(3) . ? C26 H26A 0.9500 . ? C27 C28 1.395(3) . ? C27 C35 1.518(3) . ? C28 C29 1.384(3) . ? C28 H28A 0.9500 . ? C29 C32 1.481(3) . ? C30 C31 1.389(4) . ? C30 H30A 0.9500 . ? C31 C32 1.392(3) . ? C31 H31A 0.9500 . ? C32 C33 1.383(4) . ? C33 C34 1.384(3) . ? C33 H33A 0.9500 . ? C34 H34A 0.9500 . ? C35 C37 1.512(5) . ? C35 C38 1.513(5) . ? C35 C36 1.524(4) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? N50 C50 1.156(4) . ? C50 S50 1.637(3) . ? N60 C60 1.154(4) . ? C60 S60 1.626(3) . ? O100 C100 1.416(6) . ? O100 H100 0.8400 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? 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 N60 Co1 N50 178.31(10) . . ? N60 Co1 N6 90.09(9) . 4_553 ? N50 Co1 N6 88.46(9) . 4_553 ? N60 Co1 N1 88.48(9) . 4_644 ? N50 Co1 N1 92.96(9) . 4_644 ? N6 Co1 N1 178.43(9) 4_553 4_644 ? N60 Co1 N4 91.90(8) . . ? N50 Co1 N4 88.97(8) . . ? N6 Co1 N4 89.93(8) 4_553 . ? N1 Co1 N4 90.78(8) 4_644 . ? N60 Co1 N3 89.60(9) . . ? N50 Co1 N3 89.49(8) . . ? N6 Co1 N3 88.44(8) 4_553 . ? N1 Co1 N3 90.88(8) 4_644 . ? N4 Co1 N3 177.79(8) . . ? C1 N1 C5 115.6(2) . . ? C1 N1 Co1 123.29(17) . 4_654 ? C5 N1 Co1 121.10(17) . 4_654 ? C6 N2 C10 118.1(2) . . ? C11 N3 C15 115.9(2) . . ? C11 N3 Co1 120.43(17) . . ? C15 N3 Co1 122.62(17) . . ? N1 C1 C2 124.6(2) . . ? N1 C1 H1A 117.7 . . ? C2 C1 H1A 117.7 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 116.8(2) . . ? C4 C3 C6 119.4(2) . . ? C2 C3 C6 123.8(2) . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? N1 C5 C4 124.1(2) . . ? N1 C5 H5A 117.9 . . ? C4 C5 H5A 117.9 . . ? N2 C6 C7 122.9(2) . . ? N2 C6 C3 114.5(2) . . ? C7 C6 C3 122.6(2) . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C9 C8 C7 117.0(2) . . ? C9 C8 C16 122.5(2) . . ? C7 C8 C16 120.4(2) . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? N2 C10 C9 122.6(2) . . ? N2 C10 C13 115.0(2) . . ? C9 C10 C13 122.4(2) . . ? N3 C11 C12 123.9(2) . . ? N3 C11 H11A 118.0 . . ? C12 C11 H11A 118.0 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C14 C13 C12 116.9(2) . . ? C14 C13 C10 120.1(2) . . ? C12 C13 C10 123.0(2) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? N3 C15 C14 123.9(2) . . ? N3 C15 H15A 118.0 . . ? C14 C15 H15A 118.0 . . ? C17 C16 C8 110.6(2) . . ? C17 C16 C19 108.1(3) . . ? C8 C16 C19 111.9(2) . . ? C17 C16 C18 109.4(3) . . ? C8 C16 C18 107.4(2) . . ? C19 C16 C18 109.4(4) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C24 N4 C20 116.0(2) . . ? C24 N4 Co1 120.75(17) . . ? C20 N4 Co1 121.95(16) . . ? C25 N5 C29 117.6(2) . . ? C34 N6 C30 116.3(2) . . ? C34 N6 Co1 121.18(18) . 4_543 ? C30 N6 Co1 122.56(17) . 4_543 ? N4 C20 C21 124.0(2) . . ? N4 C20 H20A 118.0 . . ? C21 C20 H20A 118.0 . . ? C20 C21 C22 119.7(2) . . ? C20 C21 H21A 120.2 . . ? C22 C21 H21A 120.2 . . ? C23 C22 C21 117.0(2) . . ? C23 C22 C25 123.1(2) . . ? C21 C22 C25 119.9(2) . . ? C22 C23 C24 119.5(2) . . ? C22 C23 H23A 120.3 . . ? C24 C23 H23A 120.3 . . ? N4 C24 C23 123.5(2) . . ? N4 C24 H24A 118.2 . . ? C23 C24 H24A 118.2 . . ? N5 C25 C26 122.7(2) . . ? N5 C25 C22 114.8(2) . . ? C26 C25 C22 122.5(2) . . ? C25 C26 C27 120.3(2) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C26 C27 C28 116.5(2) . . ? C26 C27 C35 120.4(2) . . ? C28 C27 C35 123.1(2) . . ? C29 C28 C27 120.0(2) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? N5 C29 C28 122.9(2) . . ? N5 C29 C32 114.6(2) . . ? C28 C29 C32 122.5(2) . . ? N6 C30 C31 124.3(2) . . ? N6 C30 H30A 117.9 . . ? C31 C30 H30A 117.9 . . ? C30 C31 C32 118.4(3) . . ? C30 C31 H31A 120.8 . . ? C32 C31 H31A 120.8 . . ? C33 C32 C31 117.7(2) . . ? C33 C32 C29 119.8(2) . . ? C31 C32 C29 122.4(2) . . ? C32 C33 C34 119.6(2) . . ? C32 C33 H33A 120.2 . . ? C34 C33 H33A 120.2 . . ? N6 C34 C33 123.6(2) . . ? N6 C34 H34A 118.2 . . ? C33 C34 H34A 118.2 . . ? C37 C35 C38 109.0(3) . . ? C37 C35 C27 108.4(3) . . ? C38 C35 C27 110.8(2) . . ? C37 C35 C36 108.9(3) . . ? C38 C35 C36 107.8(3) . . ? C27 C35 C36 111.9(2) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C50 N50 Co1 165.8(2) . . ? N50 C50 S50 177.2(3) . . ? C60 N60 Co1 167.7(3) . . ? N60 C60 S60 176.2(4) . . ? C100 O100 H100 109.5 . . ? O100 C100 H10A 109.5 . . ? O100 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O100 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.072 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.068 # Attachment '- GQ268.CIF' data_gq268 _database_code_depnum_ccdc_archive 'CCDC 838858' #TrackingRef '- GQ268.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H31 N3 O8 Zn2' _chemical_formula_sum 'C27 H31 N3 O8 Zn2' _chemical_formula_weight 656.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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 26.316(6) _cell_length_b 14.8918(19) _cell_length_c 8.0849(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.687(17) _cell_angle_gamma 90.00 _cell_volume 3050.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7535 _cell_measurement_theta_min 5.66 _cell_measurement_theta_max 61.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4977 _exptl_absorpt_correction_T_max 0.8812 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40483 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4040 _reflns_number_gt 3839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0437P)^2^+2.8283P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4040 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.000 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 Zn1 Zn 0.208773(7) 0.192559(11) 0.52791(2) 0.02013(7) Uani 1 1 d . . . N1 N 0.15470(5) 0.10941(8) 0.58458(16) 0.0194(2) Uani 1 1 d . . . N2 N 0.0000 -0.01236(11) 0.7500 0.0160(3) Uani 1 2 d S . . C1 C 0.16095(6) 0.02007(10) 0.5929(2) 0.0229(3) Uani 1 1 d . . . H1A H 0.1915 -0.0051 0.5700 0.028 Uiso 1 1 calc R . . C2 C 0.12463(6) -0.03706(10) 0.6336(2) 0.0218(3) Uani 1 1 d . . . H2A H 0.1304 -0.1001 0.6385 0.026 Uiso 1 1 calc R . . C3 C 0.07971(5) -0.00157(9) 0.66715(17) 0.0156(2) Uani 1 1 d . . . C4 C 0.07387(6) 0.09152(9) 0.6604(2) 0.0213(3) Uani 1 1 d . . . H4A H 0.0440 0.1187 0.6842 0.026 Uiso 1 1 calc R . . C5 C 0.11191(6) 0.14379(10) 0.6189(2) 0.0223(3) Uani 1 1 d . . . H5A H 0.1074 0.2071 0.6147 0.027 Uiso 1 1 calc R . . C6 C 0.03860(5) -0.05797(9) 0.71006(17) 0.0160(2) Uani 1 1 d . . . C7 C 0.04021(6) -0.15160(9) 0.7096(2) 0.0222(3) Uani 1 1 d . . . H7A H 0.0686 -0.1819 0.6820 0.027 Uiso 1 1 calc R . . C8 C 0.0000 -0.20062(14) 0.7500 0.0264(5) Uani 1 2 d S . . C9 C 0.0000 -0.30310(16) 0.7500 0.0531(10) Uani 1 2 d SD . . C10 C 0.05164(19) -0.3442(3) 0.7453(10) 0.0462(12) Uani 0.50 1 d P . . H10A H 0.0497 -0.4096 0.7561 0.069 Uiso 0.50 1 calc PR . . H10B H 0.0799 -0.3206 0.8406 0.069 Uiso 0.50 1 calc PR . . H10C H 0.0591 -0.3294 0.6361 0.069 Uiso 0.50 1 calc PR . . C11 C 0.0019(2) -0.3290(3) 0.9616(7) 0.0521(12) Uani 0.50 1 d PD . . H11A H -0.0290 -0.3029 0.9895 0.078 Uiso 0.50 1 calc PR . . H11B H 0.0342 -0.3043 1.0389 0.078 Uiso 0.50 1 calc PR . . H11C H 0.0016 -0.3944 0.9754 0.078 Uiso 0.50 1 calc PR . . C12 C -0.04634(19) -0.3410(3) 0.6535(9) 0.0498(13) Uani 0.50 1 d P . . H12A H -0.0512 -0.3266 0.5319 0.075 Uiso 0.50 1 calc PR . . H12B H -0.0761 -0.3170 0.6911 0.075 Uiso 0.50 1 calc PR . . H12C H -0.0447 -0.4063 0.6689 0.075 Uiso 0.50 1 calc PR . . O20 O 0.25280(6) 0.10129(9) 0.4426(2) 0.0373(3) Uani 1 1 d . . . O21 O 0.31797(5) 0.18713(8) 0.40810(18) 0.0303(3) Uani 1 1 d . . . C20 C 0.29502(7) 0.11305(10) 0.4047(2) 0.0240(3) Uani 1 1 d . . . C21 C 0.32077(9) 0.03258(13) 0.3493(3) 0.0431(5) Uani 1 1 d . . . H21A H 0.3070 -0.0223 0.3884 0.065 Uiso 1 1 calc R . . H21B H 0.3590 0.0357 0.3998 0.065 Uiso 1 1 calc R . . H21C H 0.3131 0.0319 0.2238 0.065 Uiso 1 1 calc R . . O30 O 0.17292(5) 0.22588(9) 0.27707(15) 0.0322(3) Uani 1 1 d . . . O31 O 0.23832(5) 0.30926(9) 0.23585(17) 0.0332(3) Uani 1 1 d . . . C30 C 0.19490(6) 0.27091(10) 0.18498(19) 0.0230(3) Uani 1 1 d . . . C31 C 0.16631(9) 0.27898(16) -0.0031(2) 0.0411(5) Uani 1 1 d . . . H31A H 0.1651 0.3422 -0.0378 0.062 Uiso 1 1 calc R . . H31B H 0.1303 0.2560 -0.0229 0.062 Uiso 1 1 calc R . . H31C H 0.1850 0.2440 -0.0710 0.062 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 Zn1 0.02213(11) 0.01890(10) 0.02199(11) -0.00011(6) 0.01046(7) -0.00671(6) N1 0.0204(5) 0.0189(5) 0.0203(6) 0.0015(4) 0.0079(4) -0.0040(4) N2 0.0157(7) 0.0153(7) 0.0184(7) 0.000 0.0071(6) 0.000 C1 0.0208(6) 0.0200(6) 0.0321(7) 0.0030(6) 0.0141(6) 0.0008(5) C2 0.0210(6) 0.0170(6) 0.0310(7) 0.0039(5) 0.0131(6) 0.0015(5) C3 0.0155(5) 0.0162(6) 0.0159(5) 0.0006(4) 0.0056(4) -0.0008(4) C4 0.0203(6) 0.0159(6) 0.0308(7) -0.0004(5) 0.0125(5) 0.0001(5) C5 0.0251(7) 0.0153(6) 0.0286(7) -0.0001(5) 0.0107(6) -0.0023(5) C6 0.0157(6) 0.0148(6) 0.0186(6) 0.0008(4) 0.0065(5) -0.0006(4) C7 0.0184(6) 0.0157(6) 0.0359(8) -0.0012(5) 0.0131(6) 0.0016(5) C8 0.0224(10) 0.0139(9) 0.0472(14) 0.000 0.0164(9) 0.000 C9 0.0310(14) 0.0125(10) 0.125(3) 0.000 0.0376(18) 0.000 C10 0.036(2) 0.0156(16) 0.093(4) 0.002(2) 0.027(3) 0.0061(13) C11 0.066(3) 0.0251(17) 0.072(3) 0.019(2) 0.029(3) 0.0017(18) C12 0.033(2) 0.0199(18) 0.088(4) -0.009(2) 0.001(2) -0.0015(15) O20 0.0398(7) 0.0267(6) 0.0549(8) -0.0081(6) 0.0290(6) -0.0053(5) O21 0.0361(7) 0.0219(5) 0.0384(7) -0.0021(5) 0.0194(5) -0.0027(4) C20 0.0313(7) 0.0206(7) 0.0223(7) -0.0007(5) 0.0108(6) 0.0015(5) C21 0.0563(12) 0.0245(8) 0.0594(13) -0.0052(8) 0.0342(10) 0.0046(8) O30 0.0401(7) 0.0342(6) 0.0219(5) 0.0018(5) 0.0075(5) -0.0158(5) O31 0.0294(6) 0.0412(7) 0.0271(6) 0.0055(5) 0.0046(5) -0.0114(5) C30 0.0298(7) 0.0199(6) 0.0190(6) -0.0009(5) 0.0060(5) -0.0031(5) C31 0.0495(11) 0.0487(11) 0.0208(8) 0.0042(8) 0.0018(7) -0.0138(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Zn1 O20 2.0244(13) . ? Zn1 N1 2.0299(12) . ? Zn1 O31 2.0369(14) 7_556 ? Zn1 O21 2.0420(12) 7_556 ? Zn1 O30 2.0530(13) . ? Zn1 Zn1 2.8928(5) 7_556 ? N1 C5 1.3329(19) . ? N1 C1 1.3400(19) . ? N2 C6 1.3322(15) 2_556 ? N2 C6 1.3322(15) . ? C1 C2 1.3840(19) . ? C1 H1A 0.9500 . ? C2 C3 1.3871(19) . ? C2 H2A 0.9500 . ? C3 C4 1.3941(18) . ? C3 C6 1.4828(18) . ? C4 C5 1.379(2) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.3950(18) . ? C7 C8 1.3949(18) . ? C7 H7A 0.9500 . ? C8 C7 1.3949(18) 2_556 ? C8 C9 1.526(3) . ? C9 C12 1.378(5) . ? C9 C12 1.378(5) 2_556 ? C9 C10 1.501(4) 2_556 ? C9 C10 1.501(4) . ? C9 C11 1.741(5) 2_556 ? C9 C11 1.741(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O20 C20 1.242(2) . ? O21 C20 1.254(2) . ? O21 Zn1 2.0420(12) 7_556 ? C20 C21 1.503(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O30 C30 1.2535(19) . ? O31 C30 1.244(2) . ? O31 Zn1 2.0369(14) 7_556 ? C30 C31 1.508(2) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? 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 O20 Zn1 N1 99.68(6) . . ? O20 Zn1 O31 90.09(6) . 7_556 ? N1 Zn1 O31 97.09(5) . 7_556 ? O20 Zn1 O21 160.67(5) . 7_556 ? N1 Zn1 O21 99.64(5) . 7_556 ? O31 Zn1 O21 88.23(6) 7_556 7_556 ? O20 Zn1 O30 88.74(6) . . ? N1 Zn1 O30 101.97(5) . . ? O31 Zn1 O30 160.83(5) 7_556 . ? O21 Zn1 O30 86.58(6) 7_556 . ? O20 Zn1 Zn1 79.70(4) . 7_556 ? N1 Zn1 Zn1 175.65(4) . 7_556 ? O31 Zn1 Zn1 78.62(4) 7_556 7_556 ? O21 Zn1 Zn1 81.09(4) 7_556 7_556 ? O30 Zn1 Zn1 82.34(4) . 7_556 ? C5 N1 C1 118.04(12) . . ? C5 N1 Zn1 119.73(10) . . ? C1 N1 Zn1 122.21(10) . . ? C6 N2 C6 118.70(17) 2_556 . ? N1 C1 C2 122.61(13) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C1 C2 C3 119.49(13) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C2 C3 C4 117.51(12) . . ? C2 C3 C6 122.97(12) . . ? C4 C3 C6 119.52(12) . . ? C5 C4 C3 119.42(13) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 122.92(13) . . ? N1 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? N2 C6 C7 122.39(13) . . ? N2 C6 C3 114.85(12) . . ? C7 C6 C3 122.76(12) . . ? C8 C7 C6 119.81(14) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C7 C8 C7 116.89(18) . 2_556 ? C7 C8 C9 121.56(9) . . ? C7 C8 C9 121.56(9) 2_556 . ? C12 C9 C12 131.7(4) . 2_556 ? C12 C9 C10 119.2(3) 2_556 2_556 ? C12 C9 C10 119.2(3) . . ? C10 C9 C10 131.8(4) 2_556 . ? C12 C9 C8 114.2(2) . . ? C12 C9 C8 114.2(2) 2_556 . ? C10 C9 C8 114.10(19) 2_556 . ? C10 C9 C8 114.10(19) . . ? C12 C9 C11 64.4(4) . 2_556 ? C12 C9 C11 104.6(4) 2_556 2_556 ? C10 C9 C11 98.6(3) 2_556 2_556 ? C10 C9 C11 70.8(3) . 2_556 ? C8 C9 C11 102.80(17) . 2_556 ? C12 C9 C11 104.6(4) . . ? C12 C9 C11 64.4(4) 2_556 . ? C10 C9 C11 70.8(3) 2_556 . ? C10 C9 C11 98.6(3) . . ? C8 C9 C11 102.80(17) . . ? C11 C9 C11 154.4(3) 2_556 . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C20 O20 Zn1 128.46(12) . . ? C20 O21 Zn1 125.48(11) . 7_556 ? O20 C20 O21 125.17(15) . . ? O20 C20 C21 117.79(16) . . ? O21 C20 C21 117.04(16) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C30 O30 Zn1 123.60(11) . . ? C30 O31 Zn1 129.64(11) . 7_556 ? O31 C30 O30 125.41(15) . . ? O31 C30 C31 117.39(15) . . ? O30 C30 C31 117.20(15) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.582 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.066 # Attachment '- GQ284.CIF' data_gq284 _database_code_depnum_ccdc_archive 'CCDC 838859' #TrackingRef '- GQ284.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 I2 N3 Zn, C6 H4 Cl2' _chemical_formula_sum 'C25 H23 Cl2 I2 N3 Zn' _chemical_formula_weight 755.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5721(9) _cell_length_b 18.1584(10) _cell_length_c 13.8460(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.258(6) _cell_angle_gamma 90.00 _cell_volume 2729.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21246 _cell_measurement_theta_min 4.25 _cell_measurement_theta_max 59.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 3.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3453 _exptl_absorpt_correction_T_max 0.6314 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 134402 _diffrn_reflns_av_R_equivalents 0.0904 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7753 _reflns_number_gt 7720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0400P)^2^+4.7361P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0127(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7753 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.268 _refine_ls_restrained_S_all 1.268 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 Zn1 Zn 0.71253(3) 0.174361(17) 0.53838(2) 0.01987(9) Uani 1 1 d . . . I1 I 0.934059(16) 0.214075(10) 0.569385(14) 0.02496(8) Uani 1 1 d . . . I2 I 0.60583(2) 0.083162(12) 0.395173(15) 0.03347(8) Uani 1 1 d . . . N1 N 0.6007(2) 0.26610(14) 0.51208(18) 0.0217(4) Uani 1 1 d . . . N2 N 0.3564(2) 0.48537(13) 0.54499(17) 0.0204(4) Uani 1 1 d . . . N3 N 0.2870(2) 0.63294(13) 0.82353(17) 0.0213(4) Uani 1 1 d . . . C1 C 0.5261(3) 0.28307(17) 0.4170(2) 0.0284(6) Uani 1 1 d . . . H1A H 0.5268 0.2527 0.3614 0.034 Uiso 1 1 calc R . . C2 C 0.4476(3) 0.34338(18) 0.3964(2) 0.0284(6) Uani 1 1 d . . . H2A H 0.3965 0.3538 0.3276 0.034 Uiso 1 1 calc R . . C3 C 0.4435(2) 0.38831(14) 0.47572(19) 0.0195(4) Uani 1 1 d . . . C4 C 0.5228(3) 0.37105(16) 0.5744(2) 0.0253(5) Uani 1 1 d . . . H4A H 0.5244 0.4008 0.6313 0.030 Uiso 1 1 calc R . . C5 C 0.5985(3) 0.31081(17) 0.5889(2) 0.0257(5) Uani 1 1 d . . . H5A H 0.6522 0.3001 0.6568 0.031 Uiso 1 1 calc R . . C6 C 0.3551(2) 0.45047(14) 0.45933(19) 0.0196(4) Uani 1 1 d . . . C7 C 0.2713(3) 0.46818(16) 0.3622(2) 0.0225(5) Uani 1 1 d . . . H7A H 0.2751 0.4434 0.3030 0.027 Uiso 1 1 calc R . . C8 C 0.1823(3) 0.52209(16) 0.3520(2) 0.0229(5) Uani 1 1 d . . . C9 C 0.1856(3) 0.55797(16) 0.4424(2) 0.0227(5) Uani 1 1 d . . . H9A H 0.1277 0.5958 0.4396 0.027 Uiso 1 1 calc R . . C10 C 0.2733(2) 0.53840(15) 0.53625(19) 0.0202(4) Uani 1 1 d . . . C11 C 0.3496(3) 0.57166(17) 0.8194(2) 0.0272(6) Uani 1 1 d . . . H11A H 0.3978 0.5487 0.8821 0.033 Uiso 1 1 calc R . . C12 C 0.3471(3) 0.54039(17) 0.7277(2) 0.0273(6) Uani 1 1 d . . . H12A H 0.3928 0.4968 0.7282 0.033 Uiso 1 1 calc R . . C13 C 0.2777(2) 0.57276(15) 0.6347(2) 0.0201(5) Uani 1 1 d . . . C14 C 0.2134(3) 0.63665(16) 0.6393(2) 0.0243(5) Uani 1 1 d . . . H14A H 0.1654 0.6610 0.5777 0.029 Uiso 1 1 calc R . . C15 C 0.2198(3) 0.66455(16) 0.7339(2) 0.0239(5) Uani 1 1 d . . . H15A H 0.1747 0.7080 0.7356 0.029 Uiso 1 1 calc R . . C16 C 0.0832(3) 0.54152(17) 0.2490(2) 0.0262(5) Uani 1 1 d . . . C17 C 0.0876(4) 0.4901(2) 0.1623(2) 0.0388(8) Uani 1 1 d . . . H17A H 0.1668 0.4959 0.1521 0.058 Uiso 1 1 calc R . . H17B H 0.0205 0.5027 0.0985 0.058 Uiso 1 1 calc R . . H17C H 0.0783 0.4390 0.1810 0.058 Uiso 1 1 calc R . . C18 C 0.1040(4) 0.62037(18) 0.2201(2) 0.0334(7) Uani 1 1 d . . . H18A H 0.0996 0.6542 0.2739 0.050 Uiso 1 1 calc R . . H18B H 0.0405 0.6334 0.1545 0.050 Uiso 1 1 calc R . . H18C H 0.1854 0.6241 0.2135 0.050 Uiso 1 1 calc R . . C19 C -0.0437(3) 0.5354(3) 0.2596(3) 0.0453(9) Uani 1 1 d . . . H19A H -0.0555 0.4853 0.2808 0.068 Uiso 1 1 calc R . . H19B H -0.1076 0.5466 0.1933 0.068 Uiso 1 1 calc R . . H19C H -0.0493 0.5705 0.3116 0.068 Uiso 1 1 calc R . . Cl1 Cl 0.38775(13) 0.17015(9) 0.62264(10) 0.0648(3) Uani 1 1 d . . . Cl2 Cl 0.30078(14) 0.32047(9) 0.68928(9) 0.0654(3) Uani 1 1 d . . . C100 C 0.2823(4) 0.2262(3) 0.5343(3) 0.0434(9) Uani 1 1 d . . . C101 C 0.2435(4) 0.2899(3) 0.5637(3) 0.0415(9) Uani 1 1 d . . . C102 C 0.1584(4) 0.3351(3) 0.4909(4) 0.0490(10) Uani 1 1 d . . . H10A H 0.1309 0.3800 0.5108 0.059 Uiso 1 1 calc R . . C103 C 0.1155(4) 0.3120(3) 0.3883(3) 0.0522(12) Uani 1 1 d . . . H10B H 0.0579 0.3416 0.3375 0.063 Uiso 1 1 calc R . . C104 C 0.1547(4) 0.2484(3) 0.3606(3) 0.0552(12) Uani 1 1 d . . . H10C H 0.1243 0.2336 0.2904 0.066 Uiso 1 1 calc R . . C105 C 0.2388(5) 0.2040(3) 0.4330(3) 0.0512(10) Uani 1 1 d . . . H10D H 0.2659 0.1590 0.4129 0.061 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 Zn1 0.02114(15) 0.02116(15) 0.01496(14) -0.00022(10) 0.00327(11) -0.00099(10) I1 0.02078(10) 0.02793(11) 0.02366(10) 0.00466(6) 0.00450(7) -0.00094(6) I2 0.03857(13) 0.03440(13) 0.02315(11) -0.01021(7) 0.00525(8) -0.00948(8) N1 0.0208(10) 0.0238(10) 0.0185(10) -0.0006(8) 0.0042(8) 0.0000(8) N2 0.0217(10) 0.0227(10) 0.0157(9) -0.0008(8) 0.0050(8) 0.0009(8) N3 0.0230(10) 0.0226(10) 0.0155(9) -0.0006(8) 0.0032(8) 0.0038(8) C1 0.0328(15) 0.0324(14) 0.0174(12) -0.0022(10) 0.0053(11) 0.0098(11) C2 0.0335(15) 0.0340(14) 0.0148(11) -0.0007(10) 0.0045(10) 0.0111(12) C3 0.0195(11) 0.0213(11) 0.0171(10) -0.0014(8) 0.0055(9) -0.0017(9) C4 0.0276(13) 0.0255(12) 0.0183(11) -0.0055(9) 0.0022(10) 0.0007(10) C5 0.0261(13) 0.0282(13) 0.0171(11) -0.0031(10) 0.0001(9) 0.0019(10) C6 0.0199(11) 0.0213(11) 0.0165(10) -0.0012(8) 0.0049(9) -0.0004(9) C7 0.0242(12) 0.0251(12) 0.0168(11) -0.0017(9) 0.0055(9) -0.0005(10) C8 0.0232(12) 0.0243(12) 0.0186(11) 0.0002(9) 0.0040(9) -0.0008(9) C9 0.0228(12) 0.0259(12) 0.0180(11) 0.0001(9) 0.0052(9) 0.0039(10) C10 0.0217(11) 0.0221(11) 0.0158(10) -0.0012(8) 0.0054(9) 0.0004(9) C11 0.0305(14) 0.0298(13) 0.0166(11) 0.0004(10) 0.0022(10) 0.0102(11) C12 0.0307(14) 0.0291(13) 0.0173(11) 0.0004(10) 0.0023(10) 0.0128(11) C13 0.0205(11) 0.0222(11) 0.0157(10) -0.0001(8) 0.0039(9) 0.0019(9) C14 0.0303(13) 0.0244(12) 0.0164(11) 0.0032(9) 0.0059(10) 0.0078(10) C15 0.0278(13) 0.0238(12) 0.0176(11) 0.0004(9) 0.0047(10) 0.0068(10) C16 0.0257(13) 0.0308(14) 0.0171(11) 0.0015(10) 0.0011(10) 0.0016(10) C17 0.047(2) 0.0383(17) 0.0199(13) -0.0065(12) -0.0023(13) 0.0017(15) C18 0.0440(18) 0.0301(14) 0.0221(13) 0.0038(11) 0.0064(12) 0.0039(13) C19 0.0228(15) 0.069(3) 0.0372(18) 0.0113(18) 0.0017(13) -0.0015(16) Cl1 0.0608(7) 0.0843(9) 0.0462(6) 0.0260(6) 0.0148(5) 0.0174(6) Cl2 0.0709(8) 0.0912(10) 0.0354(5) -0.0096(5) 0.0201(5) -0.0107(7) C100 0.0328(17) 0.063(2) 0.0302(16) 0.0140(16) 0.0062(13) -0.0061(16) C101 0.0319(17) 0.065(3) 0.0271(15) 0.0030(15) 0.0091(13) -0.0155(16) C102 0.0330(18) 0.059(2) 0.055(2) 0.010(2) 0.0146(17) -0.0100(17) C103 0.0282(17) 0.074(3) 0.044(2) 0.022(2) -0.0014(15) -0.0120(18) C104 0.043(2) 0.079(3) 0.0314(18) 0.0062(19) -0.0024(16) -0.018(2) C105 0.052(2) 0.062(3) 0.036(2) 0.0006(18) 0.0109(18) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Zn1 N3 2.053(2) 2_646 ? Zn1 N1 2.063(2) . ? Zn1 I2 2.5501(4) . ? Zn1 I1 2.5522(4) . ? N1 C1 1.336(4) . ? N1 C5 1.345(4) . ? N2 C10 1.336(3) . ? N2 C6 1.340(3) . ? N3 C11 1.340(4) . ? N3 C15 1.344(3) . ? N3 Zn1 2.053(2) 2_656 ? C1 C2 1.388(4) . ? C1 H1A 0.9500 . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.392(4) . ? C3 C6 1.487(4) . ? C4 C5 1.372(4) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.395(4) . ? C7 C8 1.393(4) . ? C7 H7A 0.9500 . ? C8 C9 1.399(4) . ? C8 C16 1.530(4) . ? C9 C10 1.390(4) . ? C9 H9A 0.9500 . ? C10 C13 1.484(4) . ? C11 C12 1.382(4) . ? C11 H11A 0.9500 . ? C12 C13 1.391(4) . ? C12 H12A 0.9500 . ? C13 C14 1.391(4) . ? C14 C15 1.382(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C18 1.528(5) . ? C16 C19 1.530(5) . ? C16 C17 1.535(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Cl1 C100 1.728(4) . ? Cl2 C101 1.724(4) . ? C100 C101 1.354(7) . ? C100 C105 1.377(6) . ? C101 C102 1.404(6) . ? C102 C103 1.397(7) . ? C102 H10A 0.9500 . ? C103 C104 1.345(8) . ? C103 H10B 0.9500 . ? C104 C105 1.388(7) . ? C104 H10C 0.9500 . ? C105 H10D 0.9500 . ? 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 N3 Zn1 N1 105.03(10) 2_646 . ? N3 Zn1 I2 109.31(7) 2_646 . ? N1 Zn1 I2 106.37(7) . . ? N3 Zn1 I1 105.57(7) 2_646 . ? N1 Zn1 I1 109.49(7) . . ? I2 Zn1 I1 120.133(15) . . ? C1 N1 C5 117.2(3) . . ? C1 N1 Zn1 120.8(2) . . ? C5 N1 Zn1 122.03(19) . . ? C10 N2 C6 118.2(2) . . ? C11 N3 C15 117.6(2) . . ? C11 N3 Zn1 121.14(18) . 2_656 ? C15 N3 Zn1 121.17(18) . 2_656 ? N1 C1 C2 122.6(3) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 117.0(3) . . ? C2 C3 C6 122.5(2) . . ? C4 C3 C6 120.4(2) . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? N1 C5 C4 123.5(3) . . ? N1 C5 H5A 118.3 . . ? C4 C5 H5A 118.3 . . ? N2 C6 C7 122.3(2) . . ? N2 C6 C3 115.3(2) . . ? C7 C6 C3 122.2(2) . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 116.5(2) . . ? C7 C8 C16 123.1(2) . . ? C9 C8 C16 120.4(3) . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? N2 C10 C9 122.6(2) . . ? N2 C10 C13 115.2(2) . . ? C9 C10 C13 122.2(2) . . ? N3 C11 C12 122.8(3) . . ? N3 C11 H11A 118.6 . . ? C12 C11 H11A 118.6 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 117.2(2) . . ? C12 C13 C10 119.9(2) . . ? C14 C13 C10 123.0(2) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? N3 C15 C14 122.9(3) . . ? N3 C15 H15A 118.6 . . ? C14 C15 H15A 118.6 . . ? C18 C16 C19 109.7(3) . . ? C18 C16 C8 108.9(2) . . ? C19 C16 C8 109.1(3) . . ? C18 C16 C17 108.3(3) . . ? C19 C16 C17 108.9(3) . . ? C8 C16 C17 111.8(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C101 C100 C105 121.0(4) . . ? C101 C100 Cl1 121.1(3) . . ? C105 C100 Cl1 117.9(4) . . ? C100 C101 C102 120.4(4) . . ? C100 C101 Cl2 121.8(3) . . ? C102 C101 Cl2 117.7(4) . . ? C103 C102 C101 118.0(5) . . ? C103 C102 H10A 121.0 . . ? C101 C102 H10A 121.0 . . ? C104 C103 C102 120.8(4) . . ? C104 C103 H10B 119.6 . . ? C102 C103 H10B 119.6 . . ? C103 C104 C105 121.0(4) . . ? C103 C104 H10C 119.5 . . ? C105 C104 H10C 119.5 . . ? C100 C105 C104 118.9(5) . . ? C100 C105 H10D 120.6 . . ? C104 C105 H10D 120.6 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.320 _refine_diff_density_min -1.636 _refine_diff_density_rms 0.128 # Attachment '- Ligand.cif' data_Ligand _database_code_depnum_ccdc_archive 'CCDC 838860' #TrackingRef '- Ligand.cif' _audit_creation_date 11-03-11 _audit_creation_method CRYSTALS_ver_14.09 _oxford_structure_analysis_title 'pka179_123k_0m in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.0269(9) _cell_length_b 10.1440(10) _cell_length_c 10.6092(11) _cell_angle_alpha 62.324(6) _cell_angle_beta 65.248(6) _cell_angle_gamma 70.093(6) _cell_volume 768.30(14) _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 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' _cell_formula_units_Z 2 # Given Formula = C19 H19 N3 # Dc = 1.25 Fooo = 308.00 Mu = 0.75 M = 289.38 # Found Formula = C19 H19 N3 # Dc = 1.25 FOOO = 308.00 Mu = 0.75 M = 289.38 _chemical_formula_sum 'C19 H19 N3' _chemical_formula_moiety 'C19 H19 N3' _chemical_compound_source ? _chemical_formula_weight 289.38 _cell_measurement_reflns_used 3909 _cell_measurement_theta_min 4 _cell_measurement_theta_max 33 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_max 0.270 _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.075 # Sheldrick geometric approximatio 0.99 1.00 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 123 _diffrn_reflns_number 15909 _reflns_number_total 4475 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 4475 # Theoretical number of reflections is about 8987 _diffrn_reflns_theta_min 2.282 _diffrn_reflns_theta_max 30.033 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.033 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -11 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 1.61 _oxford_diffrn_Wilson_scale 26.80 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.33 # 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>3.0\s(I) _refine_ls_number_reflns 2812 _refine_ls_number_restraints 0 _refine_ls_number_parameters 199 _oxford_refine_ls_R_factor_ref 0.0439 _refine_ls_wR_factor_ref 0.0621 _refine_ls_goodness_of_fit_ref 1.1032 _refine_ls_shift/su_max 0.0002998 _refine_ls_shift/su_mean 0.0000367 # The values computed from all data _oxford_reflns_number_all 4465 _refine_ls_R_factor_all 0.0723 _refine_ls_wR_factor_all 0.1785 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3640 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_gt 0.0783 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F) + ( 0.00P)^2^ + 0.02P] ,where P=(max(Fo,0) + 2Fc)/3 ; # 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. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. 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 N1 N 1.40678(18) -0.09900(16) 0.44499(17) 0.0311 1.0000 Uani . . . . . . N2 N 0.99126(15) 0.38950(13) 0.36406(13) 0.0171 1.0000 Uani . . . . . . N3 N 0.88783(16) 0.89515(14) -0.03795(14) 0.0230 1.0000 Uani . . . . . . C1 C 1.3956(2) 0.0356(2) 0.3338(2) 0.0360 1.0000 Uani . . . . . . C2 C 1.2652(2) 0.15581(18) 0.34256(19) 0.0300 1.0000 Uani . . . . . . C3 C 1.13427(18) 0.13824(16) 0.47423(16) 0.0176 1.0000 Uani . . . . . . C4 C 1.1431(2) -0.00205(17) 0.59063(18) 0.0270 1.0000 Uani . . . . . . C5 C 1.2791(2) -0.11439(19) 0.57003(19) 0.0326 1.0000 Uani . . . . . . C6 C 0.99260(17) 0.26509(16) 0.49012(16) 0.0158 1.0000 Uani . . . . . . C7 C 0.87154(17) 0.25550(16) 0.62714(16) 0.0162 1.0000 Uani . . . . . . C8 C 0.74125(17) 0.37708(15) 0.63877(15) 0.0145 1.0000 Uani . . . . . . C9 C 0.74286(17) 0.50648(16) 0.50888(16) 0.0168 1.0000 Uani . . . . . . C10 C 0.86904(18) 0.50807(15) 0.37557(16) 0.0155 1.0000 Uani . . . . . . C11 C 0.82620(19) 0.91003(16) 0.09453(17) 0.0213 1.0000 Uani . . . . . . C12 C 0.81373(18) 0.78960(16) 0.23198(16) 0.0186 1.0000 Uani . . . . . . C13 C 0.87288(17) 0.64366(15) 0.23400(16) 0.0164 1.0000 Uani . . . . . . C14 C 0.9395(2) 0.62644(17) 0.09734(16) 0.0226 1.0000 Uani . . . . . . C15 C 0.9420(2) 0.75312(17) -0.03345(17) 0.0250 1.0000 Uani . . . . . . C16 C 0.60722(18) 0.36399(16) 0.78964(16) 0.0173 1.0000 Uani . . . . . . C17 C 0.53563(19) 0.22051(17) 0.85251(18) 0.0232 1.0000 Uani . . . . . . C18 C 0.6856(2) 0.35487(18) 0.89744(17) 0.0227 1.0000 Uani . . . . . . C19 C 0.46581(19) 0.50105(17) 0.77430(17) 0.0225 1.0000 Uani . . . . . . H11 H 1.4883 0.0474 0.2404 0.0434 1.0000 Uiso R . . . . . H21 H 1.2655 0.2526 0.2569 0.0378 1.0000 Uiso R . . . . . H41 H 1.0557 -0.0216 0.6855 0.0352 1.0000 Uiso R . . . . . H51 H 1.2823 -0.2131 0.6528 0.0412 1.0000 Uiso R . . . . . H71 H 0.8771 0.1631 0.7145 0.0203 1.0000 Uiso R . . . . . H91 H 0.6563 0.5956 0.5105 0.0220 1.0000 Uiso R . . . . . H111 H 0.7871 1.0133 0.0927 0.0276 1.0000 Uiso R . . . . . H121 H 0.7640 0.8089 0.3240 0.0232 1.0000 Uiso R . . . . . H141 H 0.9847 0.5258 0.0942 0.0278 1.0000 Uiso R . . . . . H151 H 0.9864 0.7396 -0.1298 0.0311 1.0000 Uiso R . . . . . H173 H 0.4474 0.2161 0.9491 0.0356 1.0000 Uiso R . . . . . H171 H 0.6231 0.1301 0.8694 0.0349 1.0000 Uiso R . . . . . H172 H 0.4877 0.2247 0.7807 0.0363 1.0000 Uiso R . . . . . H181 H 0.5992 0.3465 0.9961 0.0359 1.0000 Uiso R . . . . . H183 H 0.7306 0.4495 0.8572 0.0357 1.0000 Uiso R . . . . . H182 H 0.7782 0.2669 0.9097 0.0352 1.0000 Uiso R . . . . . H192 H 0.3792 0.4864 0.8737 0.0348 1.0000 Uiso R . . . . . H191 H 0.5077 0.5948 0.7400 0.0359 1.0000 Uiso R . . . . . H193 H 0.4138 0.5119 0.7024 0.0356 1.0000 Uiso 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 N1 0.0250(7) 0.0279(7) 0.0350(8) -0.0170(7) -0.0086(6) 0.0077(6) N2 0.0191(6) 0.0161(6) 0.0138(6) -0.0048(5) -0.0056(5) -0.0012(5) N3 0.0259(7) 0.0185(6) 0.0189(7) -0.0008(5) -0.0082(6) -0.0049(5) C1 0.0293(9) 0.0306(9) 0.0287(9) -0.0116(8) 0.0030(8) 0.0021(7) C2 0.0276(9) 0.0210(8) 0.0253(8) -0.0067(7) -0.0010(7) 0.0016(7) C3 0.0171(7) 0.0174(7) 0.0178(7) -0.0085(6) -0.0053(6) 0.0000(6) C4 0.0251(8) 0.0197(8) 0.0191(8) -0.0039(7) -0.0009(7) 0.0028(6) C5 0.0327(9) 0.0214(8) 0.0258(9) -0.0050(7) -0.0069(8) 0.0071(7) C6 0.0169(7) 0.0152(7) 0.0146(7) -0.0046(6) -0.0062(6) -0.0020(5) C7 0.0166(7) 0.0142(7) 0.0133(7) -0.0030(6) -0.0052(6) -0.0001(5) C8 0.0150(7) 0.0135(6) 0.0137(7) -0.0040(6) -0.0049(5) -0.0024(5) C9 0.0179(7) 0.0143(7) 0.0172(7) -0.0053(6) -0.0071(6) -0.0005(5) C10 0.0197(7) 0.0123(6) 0.0147(7) -0.0038(6) -0.0075(6) -0.0025(5) C11 0.0199(8) 0.0146(7) 0.0214(8) -0.0026(6) -0.0046(6) -0.0027(6) C12 0.0183(7) 0.0169(7) 0.0169(7) -0.0047(6) -0.0051(6) -0.0018(5) C13 0.0157(7) 0.0163(7) 0.0149(7) -0.0024(6) -0.0065(6) -0.0031(5) C14 0.0296(9) 0.0179(7) 0.0175(8) -0.0050(6) -0.0088(7) -0.0018(6) C15 0.0313(9) 0.0241(8) 0.0155(7) -0.0047(6) -0.0069(7) -0.0049(7) C16 0.0170(7) 0.0172(7) 0.0140(7) -0.0060(6) -0.0039(6) 0.0000(5) C17 0.0200(8) 0.0229(8) 0.0221(8) -0.0078(6) -0.0029(6) -0.0042(6) C18 0.0237(8) 0.0240(8) 0.0195(8) -0.0085(6) -0.0064(6) -0.0032(6) C19 0.0185(7) 0.0220(8) 0.0214(8) -0.0101(7) -0.0042(6) 0.0030(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2014(5) 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 N1 . C1 . 1.333(2) yes N1 . C5 . 1.327(2) yes N2 . C6 . 1.3479(18) yes N2 . C10 . 1.3411(18) yes N3 . C11 . 1.339(2) yes N3 . C15 . 1.339(2) yes C1 . C2 . 1.385(2) yes C1 . H11 . 0.980 no C2 . C3 . 1.382(2) yes C2 . H21 . 0.980 no C3 . C4 . 1.389(2) yes C3 . C6 . 1.4900(19) yes C4 . C5 . 1.381(2) yes C4 . H41 . 0.965 no C5 . H51 . 0.979 no C6 . C7 . 1.3884(19) yes C7 . C8 . 1.3969(19) yes C7 . H71 . 0.970 no C8 . C9 . 1.3922(19) yes C8 . C16 . 1.528(2) yes C9 . C10 . 1.393(2) yes C9 . H91 . 0.975 no C10 . C13 . 1.4895(19) yes C11 . C12 . 1.390(2) yes C11 . H111 . 0.979 no C12 . C13 . 1.385(2) yes C12 . H121 . 0.972 no C13 . C14 . 1.388(2) yes C14 . C15 . 1.384(2) yes C14 . H141 . 0.972 no C15 . H151 . 0.987 no C16 . C17 . 1.536(2) yes C16 . C18 . 1.534(2) yes C16 . C19 . 1.5310(19) yes C17 . H173 . 0.992 no C17 . H171 . 0.985 no C17 . H172 . 1.001 no C18 . H181 . 0.996 no C18 . H183 . 1.004 no C18 . H182 . 0.994 no C19 . H192 . 0.994 no C19 . H191 . 0.994 no C19 . H193 . 1.000 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 C1 . N1 . C5 . 115.17(14) yes C6 . N2 . C10 . 117.35(12) yes C11 . N3 . C15 . 115.96(13) yes N1 . C1 . C2 . 124.80(15) yes N1 . C1 . H11 . 115.7 no C2 . C1 . H11 . 119.5 no C1 . C2 . C3 . 119.21(15) yes C1 . C2 . H21 . 120.7 no C3 . C2 . H21 . 120.1 no C2 . C3 . C4 . 116.68(13) yes C2 . C3 . C6 . 121.21(13) yes C4 . C3 . C6 . 122.09(12) yes C3 . C4 . C5 . 119.42(14) yes C3 . C4 . H41 . 120.8 no C5 . C4 . H41 . 119.8 no C4 . C5 . N1 . 124.70(15) yes C4 . C5 . H51 . 118.3 no N1 . C5 . H51 . 117.0 no C3 . C6 . N2 . 115.79(12) yes C3 . C6 . C7 . 121.69(12) yes N2 . C6 . C7 . 122.51(12) yes C6 . C7 . C8 . 120.34(13) yes C6 . C7 . H71 . 119.5 no C8 . C7 . H71 . 120.2 no C7 . C8 . C9 . 116.82(12) yes C7 . C8 . C16 . 119.80(12) yes C9 . C8 . C16 . 123.38(12) yes C8 . C9 . C10 . 119.58(12) yes C8 . C9 . H91 . 120.6 no C10 . C9 . H91 . 119.9 no C9 . C10 . N2 . 123.36(12) yes C9 . C10 . C13 . 120.98(12) yes N2 . C10 . C13 . 115.65(12) yes N3 . C11 . C12 . 124.42(14) yes N3 . C11 . H111 . 116.8 no C12 . C11 . H111 . 118.8 no C11 . C12 . C13 . 118.68(14) yes C11 . C12 . H121 . 119.9 no C13 . C12 . H121 . 121.4 no C10 . C13 . C12 . 122.42(13) yes C10 . C13 . C14 . 120.01(13) yes C12 . C13 . C14 . 117.57(13) yes C13 . C14 . C15 . 119.53(14) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 120.6 no C14 . C15 . N3 . 123.79(14) yes C14 . C15 . H151 . 119.0 no N3 . C15 . H151 . 117.2 no C8 . C16 . C17 . 109.35(12) yes C8 . C16 . C18 . 108.62(12) yes C17 . C16 . C18 . 109.95(12) yes C8 . C16 . C19 . 111.44(12) yes C17 . C16 . C19 . 108.65(13) yes C18 . C16 . C19 . 108.80(12) yes C16 . C17 . H173 . 107.6 no C16 . C17 . H171 . 110.2 no H173 . C17 . H171 . 109.7 no C16 . C17 . H172 . 110.1 no H173 . C17 . H172 . 109.9 no H171 . C17 . H172 . 109.4 no C16 . C18 . H181 . 109.3 no C16 . C18 . H183 . 109.9 no H181 . C18 . H183 . 108.1 no C16 . C18 . H182 . 110.7 no H181 . C18 . H182 . 110.3 no H183 . C18 . H182 . 108.5 no C16 . C19 . H192 . 109.0 no C16 . C19 . H191 . 110.2 no H192 . C19 . H191 . 108.7 no C16 . C19 . H193 . 110.8 no H192 . C19 . H193 . 108.2 no H191 . C19 . H193 . 109.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . N3 1_546 165 0.97 2.54 3.484(2) yes