Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 X-Sun-Charset: us-ascii X-Sun-Content-Lines: 2117 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Drozdov, Andrei' 'Marchetti, Fabio' 'Martini, Domenico' 'Pettinari, Claudio' 'Pettinari, Riccardo' 'Troyanov, Sergei' _publ_contact_author_name 'Prof Claudio Pettinari' _publ_contact_author_address ; Dipartimento di Scienze Chimiche Universita degli Studi di Camerino via S. Agostino 1 60232 Camerino MC ITALY ; _publ_contact_author_email pettinar@camserv.unicam.it data_q12snph3 _database_code_CSD 158774 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C46 H36 N4 O4 Sn' _chemical_formula_weight 827.48 _chemical_melting_point ? _chemical_compound_source ? 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' 'Sn' 'Sn' -0.6537 1.4246 '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 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 16.575(3) _cell_length_b 9.972(2) _cell_length_c 23.699(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.06(3) _cell_angle_gamma 90.00 _cell_volume 3887.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method ? _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 IPDS(Stoe) _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31957 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8371 _reflns_number_observed 5592 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2042 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+8.8010P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6329 _refine_ls_number_parameters 502 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_obs 0.0361 _refine_ls_wR_factor_all 0.1257 _refine_ls_wR_factor_obs 0.0909 _refine_ls_goodness_of_fit_all 1.137 _refine_ls_goodness_of_fit_obs 1.192 _refine_ls_restrained_S_all 1.381 _refine_ls_restrained_S_obs 1.192 _refine_ls_shift/esd_max -0.014 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn Sn 0.222648(15) 0.88651(3) 0.313048(10) 0.02602(9) Uani 1 d . . O1 O 0.28109(14) 0.7022(3) 0.31906(10) 0.0286(6) Uani 1 d . . O2 O 0.3931(2) 0.8234(3) 0.31477(11) 0.0345(6) Uani 1 d . . O3 O 0.2002(2) 0.4584(3) 0.48918(10) 0.0338(6) Uani 1 d . . O4 O 0.24612(15) 0.6885(3) 0.49436(11) 0.0328(6) Uani 1 d . . H1 H 0.2188(37) 0.5745(70) 0.4929(26) 0.091(20) Uiso 1 d . . N1 N 0.1377(2) 0.3521(3) 0.40905(13) 0.0293(7) Uani 1 d . . N2 N 0.1525(2) 0.3244(3) 0.35351(12) 0.0308(7) Uani 1 d . . N3 N 0.3783(2) 0.7580(3) 0.52029(12) 0.0279(7) Uani 1 d . . N4 N 0.4558(2) 0.7412(3) 0.50421(13) 0.0303(7) Uani 1 d . . C1 C 0.3598(2) 0.7142(4) 0.31893(13) 0.0255(8) Uani 1 d . . C3 C 0.3896(2) 0.4876(4) 0.36363(13) 0.0231(7) Uani 1 d . . C2 C 0.4052(2) 0.5842(4) 0.32363(14) 0.0237(7) Uani 1 d . . C4 C 0.4318(2) 0.3660(4) 0.36576(15) 0.0297(8) Uani 1 d . . H4 H 0.4221(2) 0.3017(4) 0.39254(15) 0.036 Uiso 1 calc R . C5 C 0.4879(2) 0.3402(4) 0.3285(2) 0.0362(9) Uani 1 d . . H5 H 0.5156(2) 0.2590(4) 0.3303(2) 0.043 Uiso 1 calc R . C6 C 0.5027(2) 0.4361(5) 0.2885(2) 0.0404(10) Uani 1 d . . H6 H 0.5396(2) 0.4184(5) 0.2629(2) 0.049 Uiso 1 calc R . C7 C 0.4624(2) 0.5580(4) 0.2868(2) 0.0330(9) Uani 1 d . . H7 H 0.4738(2) 0.6230(4) 0.2608(2) 0.040 Uiso 1 calc R . C8 C 0.3329(2) 0.5155(3) 0.40675(13) 0.0221(7) Uani 1 d . . C9 C 0.2575(2) 0.4487(4) 0.39834(13) 0.0234(7) Uani 1 d . . C10 C 0.1986(2) 0.4252(4) 0.43713(15) 0.0273(8) Uani 1 d . . C11 C 0.2220(2) 0.3791(4) 0.34718(14) 0.0259(7) Uani 1 d . . C12 C 0.2499(2) 0.3700(4) 0.28962(15) 0.0354(9) Uani 1 d . . H12A H 0.3022(8) 0.3273(26) 0.2927(2) 0.053 Uiso 1 calc R . H12B H 0.2539(17) 0.4585(5) 0.2743(5) 0.053 Uiso 1 calc R . H12C H 0.2115(9) 0.3184(25) 0.2649(4) 0.053 Uiso 1 calc R . C13 C 0.0651(2) 0.3003(4) 0.4273(2) 0.0339(9) Uani 1 d . . C14 C 0.0420(3) 0.3309(6) 0.4800(2) 0.0632(15) Uani 1 d . . H14 H 0.0736(3) 0.3879(6) 0.5047(2) 0.076 Uiso 1 calc R . C15 C -0.0293(3) 0.2752(7) 0.4957(3) 0.072(2) Uani 1 d . . H15 H -0.0442(3) 0.2949(7) 0.5313(3) 0.086 Uiso 1 calc R . C16 C -0.0770(3) 0.1938(5) 0.4607(2) 0.0592(14) Uani 1 d . . H16 H -0.1243(3) 0.1576(5) 0.4719(2) 0.071 Uiso 1 calc R . C17 C -0.0546(3) 0.1656(7) 0.4085(3) 0.074(2) Uani 1 d . . H17 H -0.0871(3) 0.1093(7) 0.3840(3) 0.088 Uiso 1 calc R . C18 C 0.0155(3) 0.2189(6) 0.3911(2) 0.0577(14) Uani 1 d . . H18 H 0.0290(3) 0.1998(6) 0.3550(2) 0.069 Uiso 1 calc R . C19 C 0.3646(2) 0.6065(4) 0.44992(13) 0.0234(7) Uani 1 d . . C20 C 0.3224(2) 0.6816(4) 0.48905(14) 0.0250(7) Uani 1 d . . C21 C 0.4487(2) 0.6531(4) 0.46265(14) 0.0263(8) Uani 1 d . . C22 C 0.5248(2) 0.6140(4) 0.4405(2) 0.0326(8) Uani 1 d . . H22A H 0.5272(8) 0.6562(22) 0.4043(6) 0.049 Uiso 1 calc R . H22B H 0.5261(8) 0.5184(5) 0.4361(11) 0.049 Uiso 1 calc R . H22C H 0.5705(2) 0.6421(25) 0.4667(6) 0.049 Uiso 1 calc R . C23 C 0.3699(2) 0.8453(4) 0.56694(14) 0.0277(8) Uani 1 d . . C24 C 0.3063(3) 0.8285(5) 0.5993(2) 0.0423(10) Uani 1 d . . H24 H 0.2681(3) 0.7609(5) 0.5906(2) 0.051 Uiso 1 calc R . C25 C 0.3005(3) 0.9139(5) 0.6448(2) 0.0514(12) Uani 1 d . . H25 H 0.2577(3) 0.9038(5) 0.6664(2) 0.062 Uiso 1 calc R . C26 C 0.3573(3) 1.0140(5) 0.6586(2) 0.0453(11) Uani 1 d . . H26 H 0.3523(3) 1.0715(5) 0.6889(2) 0.054 Uiso 1 calc R . C27 C 0.4211(3) 1.0279(4) 0.6272(2) 0.0407(10) Uani 1 d . . H27 H 0.4604(3) 1.0931(4) 0.6371(2) 0.049 Uiso 1 calc R . C28 C 0.4274(2) 0.9452(4) 0.5805(2) 0.0329(8) Uani 1 d . . H28 H 0.4698(2) 0.9567(4) 0.5587(2) 0.040 Uiso 1 calc R . C29 C 0.1019(2) 0.8153(4) 0.3117(2) 0.0334(9) Uani 1 d . . C30 C 0.0836(3) 0.6885(5) 0.3320(2) 0.0456(11) Uani 1 d . . H30 H 0.1257(3) 0.6298(5) 0.3443(2) 0.055 Uiso 1 calc R . C31 C 0.0036(3) 0.6484(6) 0.3340(2) 0.0575(13) Uani 1 d . . H31 H -0.0076(3) 0.5636(6) 0.3474(2) 0.069 Uiso 1 calc R . C32 C -0.0591(3) 0.7360(6) 0.3160(2) 0.0634(15) Uani 1 d . . H32 H -0.1127(3) 0.7113(6) 0.3184(2) 0.076 Uiso 1 calc R . C33 C -0.0419(3) 0.8610(6) 0.2944(3) 0.069(2) Uani 1 d . . H33 H -0.0842(3) 0.9185(6) 0.2811(3) 0.083 Uiso 1 calc R . C34 C 0.0379(3) 0.9001(5) 0.2927(2) 0.0507(12) Uani 1 d . . H34 H 0.0487(3) 0.9844(5) 0.2786(2) 0.061 Uiso 1 calc R . C35 C 0.2563(2) 0.9894(4) 0.39078(15) 0.0281(8) Uani 1 d . . C36 C 0.1957(2) 1.0074(4) 0.4260(2) 0.0359(9) Uani 1 d . . H36 H 0.1437(2) 0.9739(4) 0.4151(2) 0.043 Uiso 1 calc R . C37 C 0.2127(3) 1.0751(5) 0.4773(2) 0.0411(10) Uani 1 d . . H37 H 0.1721(3) 1.0869(5) 0.5007(2) 0.049 Uiso 1 calc R . C38 C 0.2891(3) 1.1246(4) 0.4937(2) 0.0362(9) Uani 1 d . . H38 H 0.3002(3) 1.1704(4) 0.5280(2) 0.043 Uiso 1 calc R . C39 C 0.3495(3) 1.1065(4) 0.4592(2) 0.0389(9) Uani 1 d . . H39 H 0.4014(3) 1.1400(4) 0.4704(2) 0.047 Uiso 1 calc R . C40 C 0.3337(2) 1.0395(4) 0.4084(2) 0.0347(9) Uani 1 d . . H40 H 0.3750(2) 1.0275(4) 0.3857(2) 0.042 Uiso 1 calc R . C41 C 0.2398(2) 0.9680(4) 0.2325(2) 0.0312(8) Uani 1 d . . C42 C 0.3013(3) 1.0579(4) 0.2250(2) 0.0384(9) Uani 1 d . . H42 H 0.3375(3) 1.0844(4) 0.2561(2) 0.046 Uiso 1 calc R . C43 C 0.3094(3) 1.1086(5) 0.1717(2) 0.0501(11) Uani 1 d . . H43 H 0.3513(3) 1.1681(5) 0.1671(2) 0.060 Uiso 1 calc R . C44 C 0.2558(3) 1.0716(5) 0.1253(2) 0.0528(12) Uani 1 d . . H44 H 0.2610(3) 1.1071(5) 0.0896(2) 0.063 Uiso 1 calc R . C45 C 0.1950(3) 0.9825(5) 0.1318(2) 0.0520(12) Uani 1 d . . H45 H 0.1593(3) 0.9565(5) 0.1003(2) 0.062 Uiso 1 calc R . C46 C 0.1859(3) 0.9302(5) 0.1852(2) 0.0413(10) Uani 1 d . . H46 H 0.1440(3) 0.8702(5) 0.1893(2) 0.050 Uiso 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 Sn 0.02793(14) 0.02559(14) 0.02435(13) 0.00196(11) 0.00249(9) 0.00068(11) O1 0.0264(13) 0.0272(14) 0.0321(13) 0.0050(11) 0.0037(10) 0.0005(10) O2 0.0395(15) 0.030(2) 0.0355(14) 0.0031(12) 0.0108(12) -0.0064(12) O3 0.0407(15) 0.041(2) 0.0212(13) -0.0020(12) 0.0096(11) -0.0103(13) O4 0.0289(14) 0.037(2) 0.0331(14) -0.0098(12) 0.0076(11) -0.0044(12) N1 0.030(2) 0.031(2) 0.028(2) -0.0007(13) 0.0069(12) -0.0073(13) N2 0.034(2) 0.032(2) 0.025(2) -0.0035(14) 0.0019(13) -0.0044(14) N3 0.030(2) 0.031(2) 0.0232(15) -0.0062(13) 0.0054(12) -0.0034(13) N4 0.029(2) 0.035(2) 0.027(2) -0.0031(14) 0.0043(12) -0.0031(14) C1 0.032(2) 0.031(2) 0.015(2) 0.0022(14) 0.0062(13) -0.003(2) C3 0.024(2) 0.027(2) 0.018(2) -0.0030(14) 0.0010(13) -0.0027(14) C2 0.023(2) 0.029(2) 0.019(2) 0.0006(14) 0.0016(13) -0.0007(14) C4 0.035(2) 0.030(2) 0.024(2) 0.000(2) 0.0019(15) 0.005(2) C5 0.039(2) 0.037(2) 0.032(2) -0.008(2) 0.002(2) 0.011(2) C6 0.038(2) 0.055(3) 0.030(2) -0.008(2) 0.012(2) 0.009(2) C7 0.034(2) 0.040(2) 0.027(2) 0.002(2) 0.011(2) 0.001(2) C8 0.027(2) 0.022(2) 0.018(2) 0.0043(13) 0.0038(13) 0.0022(14) C9 0.029(2) 0.024(2) 0.017(2) 0.0012(14) 0.0031(13) -0.0002(14) C10 0.032(2) 0.026(2) 0.024(2) 0.0013(15) 0.0052(14) -0.0009(15) C11 0.029(2) 0.025(2) 0.025(2) 0.0005(15) 0.0038(14) -0.0007(15) C12 0.040(2) 0.042(2) 0.023(2) -0.010(2) 0.002(2) -0.006(2) C13 0.031(2) 0.028(2) 0.044(2) 0.003(2) 0.011(2) -0.003(2) C14 0.058(3) 0.081(4) 0.056(3) -0.015(3) 0.028(2) -0.033(3) C15 0.062(3) 0.088(4) 0.074(4) -0.012(3) 0.039(3) -0.027(3) C16 0.039(2) 0.055(3) 0.089(4) 0.004(3) 0.029(3) -0.011(2) C17 0.043(3) 0.080(4) 0.100(5) -0.023(4) 0.018(3) -0.029(3) C18 0.037(2) 0.074(4) 0.064(3) -0.020(3) 0.014(2) -0.019(2) C19 0.026(2) 0.027(2) 0.017(2) 0.0014(14) 0.0025(13) -0.0009(15) C20 0.026(2) 0.029(2) 0.020(2) -0.0011(15) 0.0036(13) -0.0024(15) C21 0.028(2) 0.027(2) 0.023(2) 0.0021(15) 0.0012(14) -0.0049(15) C22 0.032(2) 0.035(2) 0.029(2) -0.005(2) -0.0031(15) -0.003(2) C23 0.035(2) 0.027(2) 0.020(2) -0.0026(15) -0.0005(14) 0.000(2) C24 0.045(2) 0.048(3) 0.036(2) -0.014(2) 0.015(2) -0.014(2) C25 0.056(3) 0.064(3) 0.038(2) -0.019(2) 0.020(2) -0.010(2) C26 0.064(3) 0.043(3) 0.028(2) -0.014(2) 0.002(2) 0.003(2) C27 0.056(3) 0.030(2) 0.034(2) -0.008(2) -0.002(2) -0.004(2) C28 0.037(2) 0.033(2) 0.029(2) -0.002(2) 0.003(2) -0.003(2) C29 0.029(2) 0.040(2) 0.030(2) -0.004(2) -0.002(2) 0.001(2) C30 0.033(2) 0.045(3) 0.057(3) 0.012(2) -0.001(2) 0.000(2) C31 0.040(3) 0.057(3) 0.072(3) 0.015(3) -0.003(2) -0.014(2) C32 0.029(2) 0.073(4) 0.085(4) 0.004(3) -0.007(2) -0.013(2) C33 0.030(2) 0.055(3) 0.116(5) 0.005(3) -0.014(3) 0.003(2) C34 0.035(2) 0.038(3) 0.076(3) 0.003(2) -0.005(2) 0.001(2) C35 0.035(2) 0.025(2) 0.025(2) 0.0038(15) 0.0038(15) 0.000(2) C36 0.031(2) 0.043(2) 0.034(2) -0.003(2) 0.004(2) 0.001(2) C37 0.042(2) 0.047(3) 0.036(2) -0.003(2) 0.013(2) 0.009(2) C38 0.051(2) 0.030(2) 0.027(2) -0.002(2) 0.000(2) 0.002(2) C39 0.041(2) 0.038(2) 0.037(2) -0.003(2) 0.001(2) -0.012(2) C40 0.037(2) 0.036(2) 0.033(2) -0.002(2) 0.012(2) -0.005(2) C41 0.040(2) 0.027(2) 0.027(2) 0.001(2) 0.007(2) 0.011(2) C42 0.052(2) 0.032(2) 0.032(2) 0.003(2) 0.007(2) 0.000(2) C43 0.067(3) 0.040(3) 0.047(3) 0.009(2) 0.020(2) 0.000(2) C44 0.079(3) 0.052(3) 0.031(2) 0.009(2) 0.018(2) 0.012(3) C45 0.071(3) 0.058(3) 0.026(2) 0.000(2) 0.001(2) 0.018(3) C46 0.048(2) 0.044(3) 0.031(2) 0.000(2) 0.002(2) 0.003(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 Sn O1 2.075(3) . ? Sn C29 2.120(4) . ? Sn C35 2.123(4) . ? Sn C41 2.126(4) . ? O1 C1 1.311(4) . ? O2 C1 1.230(5) . ? O3 C10 1.274(4) . ? O3 H1 1.20(7) . ? O4 C20 1.288(4) . ? O4 H1 1.22(7) . ? N1 C10 1.352(5) . ? N1 N2 1.396(4) . ? N1 C13 1.424(5) . ? N2 C11 1.299(5) . ? N3 C20 1.349(5) . ? N3 N4 1.394(4) . ? N3 C23 1.427(5) . ? N4 C21 1.314(5) . ? C1 C2 1.496(5) . ? C3 C2 1.398(5) . ? C3 C4 1.398(5) . ? C3 C8 1.498(4) . ? C2 C7 1.390(5) . ? C4 C5 1.382(5) . ? C4 H4 0.93 . ? C5 C6 1.389(6) . ? C5 H5 0.93 . ? C6 C7 1.385(6) . ? C6 H6 0.93 . ? C7 H7 0.93 . ? C8 C9 1.408(5) . ? C8 C19 1.419(5) . ? C9 C10 1.440(5) . ? C9 C11 1.457(5) . ? C11 C12 1.496(5) . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 C18 1.377(6) . ? C13 C14 1.385(6) . ? C14 C15 1.397(6) . ? C14 H14 0.93 . ? C15 C16 1.345(8) . ? C15 H15 0.93 . ? C16 C17 1.365(8) . ? C16 H16 0.93 . ? C17 C18 1.385(7) . ? C17 H17 0.93 . ? C18 H18 0.93 . ? C19 C20 1.439(5) . ? C19 C21 1.465(5) . ? C21 C22 1.477(5) . ? C22 H22A 0.96 . ? C22 H22B 0.96 . ? C22 H22C 0.96 . ? C23 C24 1.388(5) . ? C23 C28 1.389(5) . ? C24 C25 1.386(6) . ? C24 H24 0.93 . ? C25 C26 1.384(7) . ? C25 H25 0.93 . ? C26 C27 1.372(6) . ? C26 H26 0.93 . ? C27 C28 1.393(6) . ? C27 H27 0.93 . ? C28 H28 0.93 . ? C29 C34 1.389(6) . ? C29 C30 1.399(6) . ? C30 C31 1.391(6) . ? C30 H30 0.93 . ? C31 C32 1.384(7) . ? C31 H31 0.93 . ? C32 C33 1.390(8) . ? C32 H32 0.93 . ? C33 C34 1.384(7) . ? C33 H33 0.93 . ? C34 H34 0.93 . ? C35 C40 1.393(5) . ? C35 C36 1.394(5) . ? C36 C37 1.389(6) . ? C36 H36 0.93 . ? C37 C38 1.369(6) . ? C37 H37 0.93 . ? C38 C39 1.381(6) . ? C38 H38 0.93 . ? C39 C40 1.372(6) . ? C39 H39 0.93 . ? C40 H40 0.93 . ? C41 C42 1.386(6) . ? C41 C46 1.397(6) . ? C42 C43 1.383(6) . ? C42 H42 0.93 . ? C43 C44 1.375(7) . ? C43 H43 0.93 . ? C44 C45 1.367(7) . ? C44 H44 0.93 . ? C45 C46 1.395(6) . ? C45 H45 0.93 . ? C46 H46 0.93 . ? 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 O1 Sn C29 97.82(13) . . ? O1 Sn C35 107.35(12) . . ? C29 Sn C35 108.75(14) . . ? O1 Sn C41 106.72(12) . . ? C29 Sn C41 110.17(15) . . ? C35 Sn C41 123.01(15) . . ? C1 O1 Sn 112.0(2) . . ? C10 O3 H1 107.3(29) . . ? C20 O4 H1 108.2(29) . . ? C10 N1 N2 111.3(3) . . ? C10 N1 C13 130.8(3) . . ? N2 N1 C13 117.9(3) . . ? C11 N2 N1 106.7(3) . . ? C20 N3 N4 112.1(3) . . ? C20 N3 C23 130.0(3) . . ? N4 N3 C23 117.8(3) . . ? C21 N4 N3 106.5(3) . . ? O2 C1 O1 122.5(3) . . ? O2 C1 C2 123.2(3) . . ? O1 C1 C2 114.3(3) . . ? C2 C3 C4 119.3(3) . . ? C2 C3 C8 121.2(3) . . ? C4 C3 C8 119.3(3) . . ? C7 C2 C3 119.6(3) . . ? C7 C2 C1 119.4(3) . . ? C3 C2 C1 121.0(3) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.6(2) . . ? C3 C4 H4 119.6(2) . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1(2) . . ? C6 C5 H5 120.1(2) . . ? C7 C6 C5 119.9(4) . . ? C7 C6 H6 120.0(2) . . ? C5 C6 H6 120.0(2) . . ? C6 C7 C2 120.7(4) . . ? C6 C7 H7 119.7(2) . . ? C2 C7 H7 119.7(2) . . ? C9 C8 C19 130.4(3) . . ? C9 C8 C3 115.9(3) . . ? C19 C8 C3 113.7(3) . . ? C8 C9 C10 130.2(3) . . ? C8 C9 C11 127.1(3) . . ? C10 C9 C11 102.6(3) . . ? O3 C10 N1 122.8(3) . . ? O3 C10 C9 129.8(3) . . ? N1 C10 C9 107.3(3) . . ? N2 C11 C9 112.1(3) . . ? N2 C11 C12 117.2(3) . . ? C9 C11 C12 130.5(3) . . ? C11 C12 H12A 109.5(2) . . ? C11 C12 H12B 109.5(2) . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5(2) . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.7(4) . . ? C18 C13 N1 119.2(4) . . ? C14 C13 N1 122.1(4) . . ? C13 C14 C15 119.3(5) . . ? C13 C14 H14 120.3(3) . . ? C15 C14 H14 120.3(3) . . ? C16 C15 C14 121.9(5) . . ? C16 C15 H15 119.0(3) . . ? C14 C15 H15 119.0(3) . . ? C15 C16 C17 118.5(4) . . ? C15 C16 H16 120.7(3) . . ? C17 C16 H16 120.7(3) . . ? C16 C17 C18 121.5(5) . . ? C16 C17 H17 119.2(3) . . ? C18 C17 H17 119.2(3) . . ? C13 C18 C17 119.9(5) . . ? C13 C18 H18 120.0(3) . . ? C17 C18 H18 120.0(3) . . ? C8 C19 C20 129.1(3) . . ? C8 C19 C21 127.6(3) . . ? C20 C19 C21 103.2(3) . . ? O4 C20 N3 122.2(3) . . ? O4 C20 C19 130.7(3) . . ? N3 C20 C19 107.0(3) . . ? N4 C21 C19 111.2(3) . . ? N4 C21 C22 116.2(3) . . ? C19 C21 C22 132.5(3) . . ? C21 C22 H22A 109.5(2) . . ? C21 C22 H22B 109.5(2) . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5(2) . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 120.3(3) . . ? C24 C23 N3 120.5(3) . . ? C28 C23 N3 119.1(3) . . ? C25 C24 C23 119.0(4) . . ? C25 C24 H24 120.5(3) . . ? C23 C24 H24 120.5(2) . . ? C26 C25 C24 121.1(4) . . ? C26 C25 H25 119.4(2) . . ? C24 C25 H25 119.4(3) . . ? C27 C26 C25 119.5(4) . . ? C27 C26 H26 120.3(2) . . ? C25 C26 H26 120.3(3) . . ? C26 C27 C28 120.6(4) . . ? C26 C27 H27 119.7(2) . . ? C28 C27 H27 119.7(2) . . ? C23 C28 C27 119.5(4) . . ? C23 C28 H28 120.3(2) . . ? C27 C28 H28 120.3(2) . . ? C34 C29 C30 118.2(4) . . ? C34 C29 Sn 118.9(3) . . ? C30 C29 Sn 122.9(3) . . ? C31 C30 C29 121.3(4) . . ? C31 C30 H30 119.3(3) . . ? C29 C30 H30 119.3(2) . . ? C32 C31 C30 119.4(5) . . ? C32 C31 H31 120.3(3) . . ? C30 C31 H31 120.3(3) . . ? C31 C32 C33 119.9(4) . . ? C31 C32 H32 120.0(3) . . ? C33 C32 H32 120.0(3) . . ? C34 C33 C32 120.2(5) . . ? C34 C33 H33 119.9(3) . . ? C32 C33 H33 119.9(3) . . ? C33 C34 C29 120.9(5) . . ? C33 C34 H34 119.5(3) . . ? C29 C34 H34 119.5(3) . . ? C40 C35 C36 118.6(3) . . ? C40 C35 Sn 124.6(3) . . ? C36 C35 Sn 116.7(3) . . ? C37 C36 C35 120.2(4) . . ? C37 C36 H36 119.9(2) . . ? C35 C36 H36 119.9(2) . . ? C38 C37 C36 120.3(4) . . ? C38 C37 H37 119.8(2) . . ? C36 C37 H37 119.8(2) . . ? C37 C38 C39 119.8(4) . . ? C37 C38 H38 120.1(2) . . ? C39 C38 H38 120.1(2) . . ? C40 C39 C38 120.6(4) . . ? C40 C39 H39 119.7(2) . . ? C38 C39 H39 119.7(2) . . ? C39 C40 C35 120.5(4) . . ? C39 C40 H40 119.8(2) . . ? C35 C40 H40 119.8(2) . . ? C42 C41 C46 118.7(4) . . ? C42 C41 Sn 123.0(3) . . ? C46 C41 Sn 118.4(3) . . ? C43 C42 C41 120.6(4) . . ? C43 C42 H42 119.7(3) . . ? C41 C42 H42 119.7(2) . . ? C44 C43 C42 120.4(5) . . ? C44 C43 H43 119.8(3) . . ? C42 C43 H43 119.8(3) . . ? C45 C44 C43 119.8(4) . . ? C45 C44 H44 120.1(3) . . ? C43 C44 H44 120.1(3) . . ? C44 C45 C46 120.6(4) . . ? C44 C45 H45 119.7(3) . . ? C46 C45 H45 119.7(3) . . ? C45 C46 C41 119.9(4) . . ? C45 C46 H46 120.1(3) . . ? C41 C46 H46 120.1(2) . . ? _refine_diff_density_max 1.189 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.075 data_snq12Ph3H2O _database_code_CSD 158775 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C47.50 H41 N4 O5.50 Sn' _chemical_formula_weight 874.53 _chemical_melting_point ? _chemical_compound_source ? 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' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.944(2) _cell_length_b 12.883(3) _cell_length_c 16.213(3) _cell_angle_alpha 84.27(3) _cell_angle_beta 75.58(3) _cell_angle_gamma 68.90(3) _cell_volume 2065.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method ? _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 IPDS(Stoe) _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11808 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.1077 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.79 _reflns_number_total 7261 _reflns_number_observed 4353 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1505 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5756 _refine_ls_number_parameters 543 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_obs 0.0485 _refine_ls_wR_factor_all 0.1239 _refine_ls_wR_factor_obs 0.1083 _refine_ls_goodness_of_fit_all 0.932 _refine_ls_goodness_of_fit_obs 1.045 _refine_ls_restrained_S_all 0.917 _refine_ls_restrained_S_obs 1.045 _refine_ls_shift/esd_max 0.017 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn Sn 0.22869(4) 0.18300(4) 0.33494(2) 0.03220(15) Uani 1 d . . O1 O 0.0865(4) 0.2545(3) 0.2571(2) 0.0349(9) Uani 1 d . . O2 O 0.0403(4) 0.1002(4) 0.3028(2) 0.0373(10) Uani 1 d . . O3 O -0.0737(5) -0.2168(4) 0.2143(3) 0.0466(11) Uani 1 d . . H1 H 0.0076(71) -0.2360(60) 0.2030(44) 0.056 Uiso 1 d . . O4 O 0.1493(4) -0.2028(4) 0.1815(2) 0.0431(10) Uani 1 d . . O5 O 0.3910(4) 0.0955(4) 0.4354(3) 0.0439(12) Uani 1 d . . H2 H 0.4593(72) 0.0536(61) 0.4244(46) 0.053 Uiso 1 d . . H3 H 0.3705(67) 0.0661(55) 0.4811(44) 0.053 Uiso 1 d . . N1 N -0.2385(5) -0.1483(4) 0.3344(3) 0.0390(12) Uani 1 d . . N2 N -0.3032(5) -0.0506(5) 0.3804(3) 0.0400(12) Uani 1 d . . N3 N 0.2408(5) -0.1151(4) 0.0625(3) 0.0393(12) Uani 1 d . . N4 N 0.2050(5) -0.0127(4) 0.0186(3) 0.0402(12) Uani 1 d . . C1 C 0.0159(6) 0.1900(5) 0.2632(3) 0.0346(14) Uani 1 d . . C2 C -0.1026(6) 0.2326(5) 0.2234(3) 0.0346(14) Uani 1 d . . C3 C -0.1500(5) 0.1558(5) 0.1974(3) 0.0333(14) Uani 1 d . . C4 C -0.2661(6) 0.1978(6) 0.1655(3) 0.041(2) Uani 1 d . . H4 H -0.3006(6) 0.1476(6) 0.1483(3) 0.049 Uiso 1 calc R . C5 C -0.3310(7) 0.3099(7) 0.1586(4) 0.052(2) Uani 1 d . . H5 H -0.4096(7) 0.3363(7) 0.1365(4) 0.063 Uiso 1 calc R . C6 C -0.2838(7) 0.3857(6) 0.1836(4) 0.052(2) Uani 1 d . . H6 H -0.3295(7) 0.4634(6) 0.1792(4) 0.063 Uiso 1 calc R . C7 C -0.1680(6) 0.3450(6) 0.2151(3) 0.042(2) Uani 1 d . . H7 H -0.1333(6) 0.3958(6) 0.2312(3) 0.051 Uiso 1 calc R . C8 C -0.0815(6) 0.0332(5) 0.1998(3) 0.0335(14) Uani 1 d . . C9 C -0.1473(5) -0.0253(5) 0.2654(3) 0.0350(14) Uani 1 d . . C10 C -0.1416(6) -0.1372(5) 0.2661(3) 0.0356(14) Uani 1 d . . C11 C -0.2500(6) 0.0228(5) 0.3408(3) 0.0375(15) Uani 1 d . . C12 C -0.2916(6) 0.1337(6) 0.3815(3) 0.045(2) Uani 1 d . . H12A H -0.3376(35) 0.1926(6) 0.3451(13) 0.067 Uiso 1 calc R . H12B H -0.2117(7) 0.1463(15) 0.3888(23) 0.067 Uiso 1 calc R . H12C H -0.3528(32) 0.1347(13) 0.4373(11) 0.067 Uiso 1 calc R . C13 C -0.2786(7) -0.2436(6) 0.3601(3) 0.041(2) Uani 1 d . . C14 C -0.1838(8) -0.3479(7) 0.3573(4) 0.056(2) Uani 1 d . . H14 H -0.0910(8) -0.3574(7) 0.3386(4) 0.068 Uiso 1 calc R . C15 C -0.2230(9) -0.4421(7) 0.3823(4) 0.064(2) Uani 1 d . . H15 H -0.1578(9) -0.5150(7) 0.3797(4) 0.077 Uiso 1 calc R . C16 C -0.3585(10) -0.4251(8) 0.4106(4) 0.065(2) Uani 1 d . . H16 H -0.3868(10) -0.4869(8) 0.4288(4) 0.078 Uiso 1 calc R . C17 C -0.4523(9) -0.3207(8) 0.4129(4) 0.063(2) Uani 1 d . . H17 H -0.5451(9) -0.3112(8) 0.4318(4) 0.076 Uiso 1 calc R . C18 C -0.4142(7) -0.2267(6) 0.3879(3) 0.050(2) Uani 1 d . . H18 H -0.4797(7) -0.1540(6) 0.3901(3) 0.060 Uiso 1 calc R . C19 C 0.0341(6) -0.0104(5) 0.1355(3) 0.0332(14) Uani 1 d . . C20 C 0.1389(6) -0.1164(6) 0.1324(3) 0.0356(15) Uani 1 d . . C21 C 0.0863(6) 0.0493(5) 0.0600(3) 0.0341(14) Uani 1 d . . C22 C 0.0248(7) 0.1601(5) 0.0226(3) 0.044(2) Uani 1 d . . H22A H 0.0230(35) 0.2182(6) 0.0581(13) 0.066 Uiso 1 calc R . H22B H -0.0673(14) 0.1702(13) 0.0200(22) 0.066 Uiso 1 calc R . H22C H 0.0780(22) 0.1653(12) -0.0350(9) 0.066 Uiso 1 calc R . C23 C 0.3702(6) -0.1917(6) 0.0347(3) 0.041(2) Uani 1 d . . C24 C 0.4016(7) -0.3042(6) 0.0557(4) 0.053(2) Uani 1 d . . H24 H 0.3335(7) -0.3308(6) 0.0883(4) 0.064 Uiso 1 calc R . C25 C 0.5342(8) -0.3786(8) 0.0286(4) 0.071(2) Uani 1 d . . H25 H 0.5559(8) -0.4546(8) 0.0456(4) 0.085 Uiso 1 calc R . C26 C 0.6329(8) -0.3428(10) -0.0224(5) 0.082(3) Uani 1 d . . H26 H 0.7216(8) -0.3935(10) -0.0423(5) 0.098 Uiso 1 calc R . C27 C 0.5986(8) -0.2294(10) -0.0439(4) 0.079(3) Uani 1 d . . H27 H 0.6658(8) -0.2035(10) -0.0787(4) 0.095 Uiso 1 calc R . C28 C 0.4708(7) -0.1545(7) -0.0163(3) 0.055(2) Uani 1 d . . H28 H 0.4506(7) -0.0781(7) -0.0316(3) 0.067 Uiso 1 calc R . C29 C 0.3629(5) 0.0372(5) 0.2670(3) 0.0302(13) Uani 1 d . . C30 C 0.3325(6) -0.0591(5) 0.2636(3) 0.0376(14) Uani 1 d . . H30 H 0.2455(6) -0.0600(5) 0.2912(3) 0.045 Uiso 1 calc R . C31 C 0.4263(6) -0.1519(6) 0.2212(3) 0.044(2) Uani 1 d . . H31 H 0.4037(6) -0.2164(6) 0.2202(3) 0.052 Uiso 1 calc R . C32 C 0.5531(7) -0.1523(6) 0.1798(4) 0.050(2) Uani 1 d . . H32 H 0.6178(7) -0.2162(6) 0.1499(4) 0.060 Uiso 1 calc R . C33 C 0.5845(6) -0.0570(6) 0.1829(3) 0.049(2) Uani 1 d . . H33 H 0.6716(6) -0.0564(6) 0.1549(3) 0.059 Uiso 1 calc R . C34 C 0.4913(6) 0.0355(6) 0.2256(3) 0.0386(15) Uani 1 d . . H34 H 0.5148(6) 0.0994(6) 0.2269(3) 0.046 Uiso 1 calc R . C35 C 0.2940(6) 0.3234(5) 0.3121(3) 0.0385(15) Uani 1 d . . C36 C 0.3705(6) 0.3435(6) 0.3626(4) 0.049(2) Uani 1 d . . H36 H 0.3963(6) 0.2927(6) 0.4071(4) 0.058 Uiso 1 calc R . C37 C 0.4083(7) 0.4361(6) 0.3482(5) 0.060(2) Uani 1 d . . H37 H 0.4607(7) 0.4478(6) 0.3827(5) 0.072 Uiso 1 calc R . C38 C 0.3723(7) 0.5111(6) 0.2856(5) 0.062(2) Uani 1 d . . H38 H 0.4006(7) 0.5737(6) 0.2756(5) 0.074 Uiso 1 calc R . C39 C 0.2948(9) 0.4953(7) 0.2373(4) 0.069(2) Uani 1 d . . H39 H 0.2655(9) 0.5488(7) 0.1951(4) 0.083 Uiso 1 calc R . C40 C 0.2584(7) 0.4005(6) 0.2498(4) 0.056(2) Uani 1 d . . H40 H 0.2076(7) 0.3891(6) 0.2141(4) 0.067 Uiso 1 calc R . C41 C 0.0884(5) 0.2039(5) 0.4538(3) 0.0312(13) Uani 1 d . . C42 C 0.0159(6) 0.3118(6) 0.4809(4) 0.044(2) Uani 1 d . . H42 H 0.0336(6) 0.3720(6) 0.4476(4) 0.053 Uiso 1 calc R . C43 C -0.0838(7) 0.3332(6) 0.5573(4) 0.055(2) Uani 1 d . . H43 H -0.1344(7) 0.4076(6) 0.5753(4) 0.066 Uiso 1 calc R . C44 C -0.1075(7) 0.2458(6) 0.6057(4) 0.049(2) Uani 1 d . . H44 H -0.1753(7) 0.2603(6) 0.6571(4) 0.059 Uiso 1 calc R . C45 C -0.0353(6) 0.1383(6) 0.5812(3) 0.047(2) Uani 1 d . . H45 H -0.0516(6) 0.0786(6) 0.6159(3) 0.056 Uiso 1 calc R . C46 C 0.0631(6) 0.1164(5) 0.5045(3) 0.0406(15) Uani 1 d . . H46 H 0.1127(6) 0.0417(5) 0.4870(3) 0.049 Uiso 1 calc R . C47 C 0.8577(14) -0.3965(10) 0.1172(8) 0.044(3) Uani 0.50 d P . C48 C 1.0173(13) -0.5452(9) -0.0331(15) 0.253(10) Uani 0.50 d P . O6 O 1.0173(13) -0.5452(9) -0.0331(15) 0.253(10) Uani 0.50 d P . C49 C 0.8764(13) -0.5830(11) -0.0567(10) 0.055(4) Uani 0.50 d P . 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 Sn 0.0333(2) 0.0512(3) 0.0170(2) 0.00099(15) -0.00230(14) -0.0231(2) O1 0.037(2) 0.050(3) 0.026(2) 0.007(2) -0.012(2) -0.023(2) O2 0.035(2) 0.056(3) 0.025(2) 0.005(2) -0.008(2) -0.021(2) O3 0.052(3) 0.061(3) 0.032(2) 0.000(2) -0.002(2) -0.031(3) O4 0.049(3) 0.053(3) 0.027(2) 0.010(2) -0.006(2) -0.021(2) O5 0.031(2) 0.073(4) 0.021(2) 0.006(2) -0.002(2) -0.015(3) N1 0.041(3) 0.063(4) 0.020(2) 0.002(2) -0.003(2) -0.029(3) N2 0.038(3) 0.067(4) 0.021(2) 0.004(2) -0.005(2) -0.028(3) N3 0.042(3) 0.057(4) 0.021(2) 0.007(2) -0.004(2) -0.024(3) N4 0.045(3) 0.056(4) 0.022(2) 0.005(2) -0.005(2) -0.024(3) C1 0.031(3) 0.050(4) 0.021(3) -0.006(3) -0.003(2) -0.013(3) C2 0.034(3) 0.052(4) 0.018(2) -0.001(2) -0.002(2) -0.018(3) C3 0.024(3) 0.061(4) 0.016(2) 0.000(2) -0.001(2) -0.020(3) C4 0.034(3) 0.068(5) 0.023(3) 0.005(3) -0.005(2) -0.023(4) C5 0.040(4) 0.084(6) 0.029(3) 0.005(3) -0.010(3) -0.017(4) C6 0.051(4) 0.062(5) 0.043(4) 0.006(3) -0.012(3) -0.019(4) C7 0.045(4) 0.052(5) 0.032(3) -0.004(3) -0.008(3) -0.019(4) C8 0.034(3) 0.060(4) 0.014(2) -0.002(2) -0.006(2) -0.025(3) C9 0.031(3) 0.058(4) 0.020(3) 0.003(2) -0.005(2) -0.022(3) C10 0.032(3) 0.058(4) 0.019(3) 0.001(3) -0.004(2) -0.021(3) C11 0.032(3) 0.066(4) 0.018(3) 0.002(3) -0.004(2) -0.024(3) C12 0.040(4) 0.067(5) 0.024(3) -0.002(3) 0.003(3) -0.024(4) C13 0.057(4) 0.062(5) 0.019(3) 0.009(3) -0.012(3) -0.039(4) C14 0.067(5) 0.082(6) 0.041(4) 0.017(4) -0.023(3) -0.047(5) C15 0.087(6) 0.078(6) 0.047(4) 0.019(4) -0.031(4) -0.047(5) C16 0.095(7) 0.082(6) 0.049(4) 0.005(4) -0.022(4) -0.065(6) C17 0.072(5) 0.108(7) 0.035(3) 0.000(4) -0.002(3) -0.069(6) C18 0.054(4) 0.088(6) 0.025(3) -0.001(3) -0.003(3) -0.047(4) C19 0.040(3) 0.047(4) 0.016(2) 0.001(2) -0.006(2) -0.020(3) C20 0.038(3) 0.062(5) 0.015(2) -0.001(3) 0.000(2) -0.029(4) C21 0.039(4) 0.048(4) 0.016(2) 0.001(2) -0.002(2) -0.020(3) C22 0.057(4) 0.057(4) 0.020(3) 0.005(3) -0.001(3) -0.027(4) C23 0.038(4) 0.068(5) 0.017(3) -0.008(3) -0.005(2) -0.016(4) C24 0.051(4) 0.068(5) 0.034(3) -0.003(3) -0.011(3) -0.012(4) C25 0.076(6) 0.088(6) 0.039(4) -0.006(4) -0.020(4) -0.012(5) C26 0.051(5) 0.127(9) 0.036(4) -0.002(5) -0.005(4) 0.004(6) C27 0.035(5) 0.149(10) 0.034(4) 0.008(5) 0.001(3) -0.018(6) C28 0.045(4) 0.099(6) 0.022(3) 0.002(3) 0.000(3) -0.030(4) C29 0.026(3) 0.048(4) 0.015(2) 0.004(2) -0.006(2) -0.011(3) C30 0.040(4) 0.050(4) 0.028(3) -0.004(3) -0.008(3) -0.020(3) C31 0.050(4) 0.053(4) 0.034(3) -0.003(3) -0.014(3) -0.022(4) C32 0.052(4) 0.065(5) 0.028(3) -0.007(3) -0.009(3) -0.012(4) C33 0.039(4) 0.081(5) 0.024(3) 0.001(3) -0.001(3) -0.021(4) C34 0.034(3) 0.063(4) 0.019(3) -0.001(3) 0.000(2) -0.022(3) C35 0.042(4) 0.055(4) 0.022(3) 0.001(3) 0.006(2) -0.030(3) C36 0.045(4) 0.053(4) 0.056(4) -0.006(3) -0.011(3) -0.026(4) C37 0.058(5) 0.061(5) 0.071(5) -0.024(4) -0.005(4) -0.033(4) C38 0.059(5) 0.054(5) 0.071(5) -0.025(4) 0.025(4) -0.038(4) C39 0.098(6) 0.066(5) 0.051(4) 0.011(4) -0.004(4) -0.050(5) C40 0.076(5) 0.071(5) 0.033(3) 0.003(3) -0.006(3) -0.045(5) C41 0.029(3) 0.049(4) 0.019(2) 0.002(2) -0.006(2) -0.017(3) C42 0.042(4) 0.049(4) 0.032(3) 0.007(3) 0.003(3) -0.014(4) C43 0.060(5) 0.059(5) 0.038(3) 0.000(3) 0.002(3) -0.020(4) C44 0.046(4) 0.065(5) 0.026(3) 0.003(3) -0.002(3) -0.014(4) C45 0.049(4) 0.068(5) 0.026(3) 0.012(3) -0.004(3) -0.030(4) C46 0.040(4) 0.053(4) 0.032(3) 0.001(3) -0.008(3) -0.022(3) C47 0.049(8) 0.020(7) 0.064(8) 0.010(6) -0.020(7) -0.011(7) C48 0.113(9) 0.104(10) 0.570(34) 0.028(15) -0.110(15) -0.057(9) O6 0.113(9) 0.104(10) 0.570(34) 0.028(15) -0.110(15) -0.057(9) C49 0.039(8) 0.034(8) 0.095(11) -0.006(7) -0.031(8) -0.003(7) _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 Sn C41 2.116(5) . ? Sn C29 2.126(6) . ? Sn O1 2.140(4) . ? Sn C35 2.141(5) . ? O1 C1 1.306(6) . ? O2 C1 1.240(7) . ? O3 C10 1.273(7) . ? O3 H1 0.81(7) . ? O4 C20 1.290(7) . ? O5 H2 0.74(7) . ? O5 H3 0.82(7) . ? N1 C10 1.366(7) . ? N1 N2 1.387(7) . ? N1 C13 1.438(7) . ? N2 C11 1.317(7) . ? N3 C20 1.381(7) . ? N3 C23 1.396(8) . ? N3 N4 1.407(7) . ? N4 C21 1.305(7) . ? C1 C2 1.494(8) . ? C2 C7 1.375(9) . ? C2 C3 1.409(7) . ? C3 C4 1.397(8) . ? C3 C8 1.485(8) . ? C4 C5 1.368(9) . ? C4 H4 0.95 . ? C5 C6 1.389(9) . ? C5 H5 0.95 . ? C6 C7 1.391(9) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C19 1.397(8) . ? C8 C9 1.438(7) . ? C9 C10 1.419(8) . ? C9 C11 1.452(7) . ? C11 C12 1.502(8) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.368(10) . ? C13 C18 1.380(9) . ? C14 C15 1.418(9) . ? C14 H14 0.95 . ? C15 C16 1.380(11) . ? C15 H15 0.95 . ? C16 C17 1.364(11) . ? C16 H16 0.95 . ? C17 C18 1.410(9) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C20 1.428(9) . ? C19 C21 1.482(7) . ? C21 C22 1.482(9) . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 C24 1.391(9) . ? C23 C28 1.404(8) . ? C24 C25 1.408(10) . ? C24 H24 0.95 . ? C25 C26 1.379(11) . ? C25 H25 0.95 . ? C26 C27 1.402(13) . ? C26 H26 0.95 . ? C27 C28 1.376(11) . ? C27 H27 0.95 . ? C28 H28 0.95 . ? C29 C34 1.392(7) . ? C29 C30 1.405(8) . ? C30 C31 1.374(9) . ? C30 H30 0.95 . ? C31 C32 1.382(8) . ? C31 H31 0.95 . ? C32 C33 1.397(9) . ? C32 H32 0.95 . ? C33 C34 1.371(9) . ? C33 H33 0.95 . ? C34 H34 0.95 . ? C35 C40 1.370(9) . ? C35 C36 1.405(8) . ? C36 C37 1.380(9) . ? C36 H36 0.95 . ? C37 C38 1.359(11) . ? C37 H37 0.95 . ? C38 C39 1.364(10) . ? C38 H38 0.95 . ? C39 C40 1.397(9) . ? C39 H39 0.95 . ? C40 H40 0.95 . ? C41 C42 1.382(8) . ? C41 C46 1.395(8) . ? C42 C43 1.408(8) . ? C42 H42 0.95 . ? C43 C44 1.372(9) . ? C43 H43 0.95 . ? C44 C45 1.366(9) . ? C44 H44 0.95 . ? C45 C46 1.404(8) . ? C45 H45 0.95 . ? C46 H46 0.95 . ? C47 O6 1.68(2) 2_745 ? C47 C48 1.68(2) 2_745 ? C48 O6 1.54(3) 2_745 ? C48 C48 1.54(3) 2_745 ? C48 C47 1.68(2) 2_745 ? C48 C49 1.91(2) . ? O6 O6 1.54(3) 2_745 ? O6 C48 1.54(3) 2_745 ? O6 C47 1.68(2) 2_745 ? O6 C49 1.91(2) . ? 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 C41 Sn C29 131.3(2) . . ? C41 Sn O1 97.3(2) . . ? C29 Sn O1 102.5(2) . . ? C41 Sn C35 108.4(2) . . ? C29 Sn C35 115.0(2) . . ? O1 Sn C35 91.2(2) . . ? C1 O1 Sn 107.5(3) . . ? C10 O3 H1 118.6(48) . . ? H2 O5 H3 93.8(76) . . ? C10 N1 N2 111.3(4) . . ? C10 N1 C13 128.4(5) . . ? N2 N1 C13 120.2(4) . . ? C11 N2 N1 107.0(4) . . ? C20 N3 C23 131.3(5) . . ? C20 N3 N4 110.5(5) . . ? C23 N3 N4 118.0(4) . . ? C21 N4 N3 107.5(4) . . ? O2 C1 O1 122.9(5) . . ? O2 C1 C2 120.6(5) . . ? O1 C1 C2 116.4(5) . . ? C7 C2 C3 120.2(5) . . ? C7 C2 C1 120.7(5) . . ? C3 C2 C1 119.0(6) . . ? C4 C3 C2 117.9(6) . . ? C4 C3 C8 118.3(5) . . ? C2 C3 C8 123.8(5) . . ? C5 C4 C3 121.2(6) . . ? C5 C4 H4 119.4(3) . . ? C3 C4 H4 119.4(4) . . ? C4 C5 C6 121.0(6) . . ? C4 C5 H5 119.5(3) . . ? C6 C5 H5 119.5(4) . . ? C7 C6 C5 118.4(7) . . ? C7 C6 H6 120.8(4) . . ? C5 C6 H6 120.8(4) . . ? C2 C7 C6 121.3(6) . . ? C2 C7 H7 119.4(3) . . ? C6 C7 H7 119.4(4) . . ? C19 C8 C9 128.6(6) . . ? C19 C8 C3 115.8(5) . . ? C9 C8 C3 115.5(5) . . ? C10 C9 C8 128.6(5) . . ? C10 C9 C11 104.4(4) . . ? C8 C9 C11 126.5(6) . . ? O3 C10 N1 120.9(5) . . ? O3 C10 C9 132.3(5) . . ? N1 C10 C9 106.6(5) . . ? N2 C11 C9 110.6(5) . . ? N2 C11 C12 118.6(5) . . ? C9 C11 C12 130.5(5) . . ? C11 C12 H12A 109.5(3) . . ? C11 C12 H12B 109.5(3) . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5(3) . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 121.4(6) . . ? C14 C13 N1 120.3(6) . . ? C18 C13 N1 118.4(7) . . ? C13 C14 C15 120.4(7) . . ? C13 C14 H14 119.8(3) . . ? C15 C14 H14 119.8(5) . . ? C16 C15 C14 118.2(8) . . ? C16 C15 H15 120.9(5) . . ? C14 C15 H15 120.9(5) . . ? C17 C16 C15 120.9(7) . . ? C17 C16 H16 119.5(4) . . ? C15 C16 H16 119.5(5) . . ? C16 C17 C18 121.2(7) . . ? C16 C17 H17 119.4(4) . . ? C18 C17 H17 119.4(5) . . ? C13 C18 C17 117.9(8) . . ? C13 C18 H18 121.1(4) . . ? C17 C18 H18 121.1(5) . . ? C8 C19 C20 128.7(5) . . ? C8 C19 C21 127.4(6) . . ? C20 C19 C21 103.4(5) . . ? O4 C20 N3 121.3(6) . . ? O4 C20 C19 131.4(5) . . ? N3 C20 C19 107.4(5) . . ? N4 C21 C19 111.2(6) . . ? N4 C21 C22 117.0(5) . . ? C19 C21 C22 131.7(5) . . ? C21 C22 H22A 109.5(3) . . ? C21 C22 H22B 109.5(3) . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5(3) . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 N3 121.5(5) . . ? C24 C23 C28 119.3(6) . . ? N3 C23 C28 119.2(6) . . ? C23 C24 C25 120.0(7) . . ? C23 C24 H24 120.0(4) . . ? C25 C24 H24 120.0(5) . . ? C26 C25 C24 121.0(8) . . ? C26 C25 H25 119.5(6) . . ? C24 C25 H25 119.5(5) . . ? C25 C26 C27 118.1(8) . . ? C25 C26 H26 121.0(6) . . ? C27 C26 H26 121.0(5) . . ? C28 C27 C26 122.1(8) . . ? C28 C27 H27 119.0(5) . . ? C26 C27 H27 119.0(5) . . ? C27 C28 C23 119.6(8) . . ? C27 C28 H28 120.2(5) . . ? C23 C28 H28 120.2(4) . . ? C34 C29 C30 117.7(5) . . ? C34 C29 Sn 117.8(4) . . ? C30 C29 Sn 124.4(4) . . ? C31 C30 C29 121.2(5) . . ? C31 C30 H30 119.4(3) . . ? C29 C30 H30 119.4(3) . . ? C30 C31 C32 120.5(6) . . ? C30 C31 H31 119.8(3) . . ? C32 C31 H31 119.8(4) . . ? C31 C32 C33 118.8(6) . . ? C31 C32 H32 120.6(4) . . ? C33 C32 H32 120.6(4) . . ? C34 C33 C32 120.8(6) . . ? C34 C33 H33 119.6(4) . . ? C32 C33 H33 119.6(4) . . ? C33 C34 C29 121.0(6) . . ? C33 C34 H34 119.5(4) . . ? C29 C34 H34 119.5(4) . . ? C40 C35 C36 116.8(5) . . ? C40 C35 Sn 121.4(4) . . ? C36 C35 Sn 121.7(5) . . ? C37 C36 C35 120.7(7) . . ? C37 C36 H36 119.7(4) . . ? C35 C36 H36 119.7(4) . . ? C38 C37 C36 121.3(6) . . ? C38 C37 H37 119.3(4) . . ? C36 C37 H37 119.3(4) . . ? C37 C38 C39 119.2(6) . . ? C37 C38 H38 120.4(4) . . ? C39 C38 H38 120.4(5) . . ? C38 C39 C40 120.1(7) . . ? C38 C39 H39 120.0(5) . . ? C40 C39 H39 120.0(4) . . ? C35 C40 C39 121.8(6) . . ? C35 C40 H40 119.1(3) . . ? C39 C40 H40 119.1(4) . . ? C42 C41 C46 118.9(5) . . ? C42 C41 Sn 116.9(4) . . ? C46 C41 Sn 124.2(4) . . ? C41 C42 C43 120.5(6) . . ? C41 C42 H42 119.7(3) . . ? C43 C42 H42 119.7(4) . . ? C44 C43 C42 119.5(7) . . ? C44 C43 H43 120.3(4) . . ? C42 C43 H43 120.3(4) . . ? C45 C44 C43 121.1(6) . . ? C45 C44 H44 119.5(3) . . ? C43 C44 H44 119.5(4) . . ? C44 C45 C46 119.7(6) . . ? C44 C45 H45 120.1(3) . . ? C46 C45 H45 120.1(4) . . ? C41 C46 C45 120.3(6) . . ? C41 C46 H46 119.9(3) . . ? C45 C46 H46 119.9(4) . . ? O6 C47 C48 0.0(11) 2_745 2_745 ? O6 C48 C48 0.0(12) 2_745 2_745 ? O6 C48 C47 137.8(12) 2_745 2_745 ? C48 C48 C47 137.8(12) 2_745 2_745 ? O6 C48 C49 119.5(13) 2_745 . ? C48 C48 C49 119.5(13) 2_745 . ? C47 C48 C49 100.0(11) 2_745 . ? O6 O6 C48 0.0(12) 2_745 2_745 ? O6 O6 C47 137.8(12) 2_745 2_745 ? C48 O6 C47 137.8(12) 2_745 2_745 ? O6 O6 C49 119.5(13) 2_745 . ? C48 O6 C49 119.5(13) 2_745 . ? C47 O6 C49 100.0(11) 2_745 . ? O6 C49 C48 0.0(13) . . ? _refine_diff_density_max 1.267 _refine_diff_density_min -0.976 _refine_diff_density_rms 0.092 data_snqme2 _database_code_CSD 158776 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C31 H26 Cl3 N4 O4 Sn' _chemical_formula_weight 743.60 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.544(2) _cell_length_b 13.143(3) _cell_length_c 13.759(3) _cell_angle_alpha 110.67(3) _cell_angle_beta 105.15(3) _cell_angle_gamma 103.15(3) _cell_volume 1610.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 933 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method ? _exptl_crystal_F_000 746 _exptl_absorpt_coefficient_mu 1.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 IPDS(Stoe) _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9112 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0874 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 26.77 _reflns_number_total 6083 _reflns_number_observed 4011 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1182 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef none _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4901 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_obs 0.0480 _refine_ls_wR_factor_all 0.1292 _refine_ls_wR_factor_obs 0.1137 _refine_ls_goodness_of_fit_all 0.967 _refine_ls_goodness_of_fit_obs 1.045 _refine_ls_restrained_S_all 0.975 _refine_ls_restrained_S_obs 1.045 _refine_ls_shift/esd_max -0.012 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn Sn 0.69219(4) 0.71247(3) 0.57234(3) 0.0198(2) Uani 1 d . . O1 O 0.3632(4) 0.3142(3) 0.2965(3) 0.0246(8) Uani 1 d . . O2 O 0.3267(5) 0.1259(3) 0.2471(3) 0.0315(9) Uani 1 d . . O3 O 0.6617(4) 0.5373(3) 0.5132(3) 0.0210(8) Uani 1 d . . O4 O 0.7457(4) 0.6790(3) 0.4162(3) 0.0229(8) Uani 1 d . . N1 N 0.8152(5) 0.4323(4) 0.5030(3) 0.0203(9) Uani 1 d . . N2 N 0.8411(5) 0.3487(4) 0.4226(4) 0.0245(10) Uani 1 d . . N3 N 0.5923(5) 0.7032(4) 0.2779(4) 0.0255(11) Uani 1 d . . N4 N 0.4752(5) 0.6382(4) 0.1796(4) 0.0264(11) Uani 1 d . . C1 C 0.3635(6) 0.2133(4) 0.2318(4) 0.0218(12) Uani 1 d . . C2 C 0.4137(6) 0.2090(5) 0.1384(4) 0.0247(12) Uani 1 d . . C3 C 0.5067(6) 0.3060(5) 0.1427(4) 0.0248(12) Uani 1 d . . C4 C 0.5439(7) 0.2975(5) 0.0503(4) 0.0291(13) Uani 1 d . . H4 H 0.6068(7) 0.3636(5) 0.0526(4) 0.035 Uiso 1 calc R . C5 C 0.4879(8) 0.1910(6) -0.0454(5) 0.039(2) Uani 1 d . . H5 H 0.5137(8) 0.1854(6) -0.1077(5) 0.047 Uiso 1 calc R . C7 C 0.3574(7) 0.1020(5) 0.0411(5) 0.0317(14) Uani 1 d . . C6 C 0.3968(8) 0.0949(5) -0.0509(5) 0.038(2) Uani 1 d . . H6 H 0.3601(8) 0.0233(5) -0.1166(5) 0.046 Uiso 1 calc R . C8 C 0.5798(6) 0.4178(4) 0.2475(4) 0.0218(12) Uani 1 d . . C9 C 0.6785(6) 0.4103(4) 0.3367(4) 0.0209(11) Uani 1 d . . C10 C 0.7177(6) 0.4718(4) 0.4556(4) 0.0177(11) Uani 1 d . . C11 C 0.7582(6) 0.3333(4) 0.3256(4) 0.0213(11) Uani 1 d . . C12 C 0.7673(7) 0.2487(5) 0.2232(5) 0.0325(14) Uani 1 d . . H12A H 0.8059(40) 0.2906(6) 0.1849(19) 0.049 Uiso 1 calc R . H12B H 0.6733(10) 0.1919(21) 0.1726(16) 0.049 Uiso 1 calc R . H12C H 0.8288(35) 0.2083(26) 0.2451(6) 0.049 Uiso 1 calc R . C13 C 0.8863(6) 0.4587(5) 0.6182(4) 0.0226(12) Uani 1 d . . C14 C 0.8497(7) 0.5240(5) 0.7040(5) 0.0321(14) Uani 1 d . . H14 H 0.7753(7) 0.5524(5) 0.6882(5) 0.039 Uiso 1 calc R . C15 C 0.9253(8) 0.5464(7) 0.8131(5) 0.043(2) Uani 1 d . . H15 H 0.9050(8) 0.5940(7) 0.8728(5) 0.051 Uiso 1 calc R . C16 C 1.0294(8) 0.5013(6) 0.8372(5) 0.042(2) Uani 1 d . . H16 H 1.0777(8) 0.5157(6) 0.9122(5) 0.051 Uiso 1 calc R . C17 C 1.0622(7) 0.4354(6) 0.7519(5) 0.038(2) Uani 1 d . . H17 H 1.1333(7) 0.4040(6) 0.7684(5) 0.045 Uiso 1 calc R . C18 C 0.9935(7) 0.4137(5) 0.6418(5) 0.0313(14) Uani 1 d . . H18 H 1.0184(7) 0.3693(5) 0.5835(5) 0.038 Uiso 1 calc R . C19 C 0.5574(6) 0.5185(5) 0.2462(4) 0.0244(12) Uani 1 d . . C20 C 0.6425(6) 0.6355(4) 0.3227(4) 0.0196(11) Uani 1 d . . C21 C 0.4530(6) 0.5283(5) 0.1589(4) 0.0242(12) Uani 1 d . . C22 C 0.3338(7) 0.4366(5) 0.0548(5) 0.0347(15) Uani 1 d . . H22A H 0.2896(29) 0.3728(18) 0.0700(11) 0.052 Uiso 1 calc R . H22B H 0.3692(9) 0.4069(26) -0.0046(12) 0.052 Uiso 1 calc R . H22C H 0.2644(22) 0.4701(11) 0.0308(20) 0.052 Uiso 1 calc R . C23 C 0.6419(7) 0.8284(5) 0.3245(4) 0.0281(14) Uani 1 d . . C24 C 0.5404(8) 0.8821(5) 0.3224(5) 0.037(2) Uani 1 d . . H24 H 0.4434(8) 0.8367(5) 0.2933(5) 0.044 Uiso 1 calc R . C25 C 0.5839(10) 1.0023(6) 0.3635(6) 0.049(2) Uani 1 d . . H25 H 0.5166(10) 1.0396(6) 0.3607(6) 0.059 Uiso 1 calc R . C26 C 0.7265(11) 1.0677(6) 0.4087(6) 0.060(2) Uani 1 d . . H26 H 0.7570(11) 1.1500(6) 0.4384(6) 0.072 Uiso 1 calc R . C27 C 0.8248(10) 1.0123(6) 0.4104(6) 0.054(2) Uani 1 d . . H27 H 0.9221(10) 1.0574(6) 0.4404(6) 0.065 Uiso 1 calc R . C28 C 0.7825(8) 0.8919(6) 0.3688(6) 0.040(2) Uani 1 d . . H28 H 0.8498(8) 0.8546(6) 0.3711(6) 0.048 Uiso 1 calc R . C29 C 0.5003(6) 0.7268(5) 0.4938(5) 0.0249(12) Uani 1 d . . H29A H 0.5196(6) 0.7957(19) 0.4797(29) 0.037 Uiso 1 calc R . H29B H 0.4467(18) 0.7340(33) 0.5427(14) 0.037 Uiso 1 calc R . H29C H 0.4458(18) 0.6572(15) 0.4226(15) 0.037 Uiso 1 calc R . C30 C 0.9100(7) 0.8051(6) 0.6615(5) 0.0368(14) Uani 1 d . . H30A H 0.9363(10) 0.8091(32) 0.7369(13) 0.055 Uiso 1 calc R . H30B H 0.9325(10) 0.8840(12) 0.6671(30) 0.055 Uiso 1 calc R . H30C H 0.9622(7) 0.7652(20) 0.6220(19) 0.055 Uiso 1 calc R . C31 C 0.1217(11) 0.8833(8) 0.1790(9) 0.075(3) Uani 1 d . . H31 H 0.1766(114) 0.9754(94) 0.2087(85) 0.090 Uiso 1 d . . Cl1 Cl 0.1652(4) 0.8988(3) 0.3193(3) 0.0974(9) Uani 1 d . . Cl2 Cl -0.0540(39) 0.8571(32) 0.1528(49) 0.166(16) Uani 0.22(4) d P . Cl2A Cl -0.0550(8) 0.8628(8) 0.1214(9) 0.118(3) Uani 0.78(4) d P . Cl3 Cl 0.1543(46) 0.7502(26) 0.1057(33) 0.073(7) Uani 0.22(4) d P . Cl3A Cl 0.1679(16) 0.7764(16) 0.0981(12) 0.123(4) Uani 0.78(4) d P . 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 Sn 0.0232(2) 0.0176(2) 0.0209(2) 0.00896(14) 0.00843(15) 0.0101(2) O1 0.033(3) 0.020(2) 0.021(2) 0.006(2) 0.010(2) 0.013(2) O2 0.040(3) 0.019(2) 0.036(2) 0.013(2) 0.017(2) 0.008(2) O3 0.021(2) 0.022(2) 0.025(2) 0.014(2) 0.009(2) 0.010(2) O4 0.024(2) 0.021(2) 0.025(2) 0.014(2) 0.006(2) 0.009(2) N1 0.024(3) 0.019(2) 0.020(2) 0.009(2) 0.007(2) 0.012(2) N2 0.028(3) 0.024(2) 0.027(2) 0.012(2) 0.011(2) 0.015(2) N3 0.034(3) 0.022(2) 0.025(2) 0.015(2) 0.009(2) 0.013(2) N4 0.038(3) 0.022(2) 0.023(2) 0.013(2) 0.010(2) 0.014(2) C1 0.023(3) 0.019(3) 0.021(3) 0.008(2) 0.006(2) 0.008(2) C2 0.035(4) 0.024(3) 0.019(3) 0.011(2) 0.010(2) 0.017(3) C3 0.035(4) 0.027(3) 0.022(3) 0.015(2) 0.011(3) 0.021(3) C4 0.044(4) 0.027(3) 0.023(3) 0.015(2) 0.013(3) 0.018(3) C5 0.069(5) 0.038(3) 0.028(3) 0.019(3) 0.026(3) 0.033(4) C7 0.045(4) 0.024(3) 0.022(3) 0.006(2) 0.009(3) 0.015(3) C6 0.062(5) 0.029(3) 0.023(3) 0.007(3) 0.017(3) 0.021(3) C8 0.034(4) 0.018(2) 0.019(2) 0.010(2) 0.013(2) 0.012(3) C9 0.032(4) 0.013(2) 0.019(2) 0.006(2) 0.010(2) 0.011(2) C10 0.024(3) 0.013(2) 0.021(2) 0.008(2) 0.010(2) 0.011(2) C11 0.024(3) 0.016(2) 0.025(3) 0.010(2) 0.009(2) 0.007(2) C12 0.037(4) 0.033(3) 0.028(3) 0.009(3) 0.010(3) 0.024(3) C13 0.022(3) 0.023(3) 0.022(3) 0.013(2) 0.003(2) 0.006(2) C14 0.038(4) 0.036(3) 0.027(3) 0.015(3) 0.011(3) 0.022(3) C15 0.048(5) 0.063(4) 0.029(3) 0.022(3) 0.017(3) 0.035(4) C16 0.047(5) 0.061(4) 0.031(3) 0.028(3) 0.012(3) 0.029(4) C17 0.041(4) 0.054(4) 0.036(3) 0.028(3) 0.016(3) 0.031(4) C18 0.031(4) 0.040(3) 0.033(3) 0.021(3) 0.016(3) 0.020(3) C19 0.036(4) 0.027(3) 0.023(3) 0.017(2) 0.016(3) 0.019(3) C20 0.024(3) 0.021(3) 0.025(3) 0.016(2) 0.015(2) 0.011(2) C21 0.025(4) 0.025(3) 0.027(3) 0.015(2) 0.010(2) 0.012(3) C22 0.038(4) 0.032(3) 0.029(3) 0.013(3) 0.003(3) 0.016(3) C23 0.044(4) 0.021(3) 0.026(3) 0.017(2) 0.014(3) 0.012(3) C24 0.061(5) 0.028(3) 0.025(3) 0.014(3) 0.013(3) 0.023(3) C25 0.083(7) 0.030(3) 0.039(4) 0.015(3) 0.017(4) 0.034(4) C26 0.102(8) 0.023(3) 0.052(4) 0.022(3) 0.023(5) 0.015(4) C27 0.063(6) 0.031(4) 0.059(5) 0.027(4) 0.013(4) -0.002(4) C28 0.052(5) 0.033(3) 0.047(4) 0.026(3) 0.021(4) 0.016(4) C29 0.017(3) 0.027(3) 0.030(3) 0.015(2) 0.005(2) 0.007(3) C30 0.027(4) 0.044(4) 0.034(3) 0.010(3) 0.013(3) 0.012(3) C31 0.062(7) 0.041(5) 0.091(7) 0.019(5) 0.013(5) -0.002(5) Cl1 0.108(3) 0.120(2) 0.088(2) 0.059(2) 0.049(2) 0.046(2) Cl2 0.105(22) 0.090(16) 0.234(34) -0.015(18) 0.126(27) -0.019(16) Cl2A 0.067(4) 0.079(4) 0.121(5) -0.008(3) -0.025(4) 0.029(4) Cl3 0.071(14) 0.043(8) 0.069(10) 0.008(8) 0.010(8) 0.006(7) Cl3A 0.083(5) 0.108(8) 0.101(6) -0.026(5) 0.020(4) 0.034(6) _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 Sn O3 2.066(3) . ? Sn C30 2.112(7) . ? Sn C29 2.114(5) . ? Sn O1 2.150(4) 2_666 ? Sn O4 2.282(4) . ? O1 C1 1.311(6) . ? O1 Sn 2.150(4) 2_666 ? O2 C1 1.235(6) . ? O3 C10 1.309(6) . ? O4 C20 1.277(7) . ? N1 C10 1.372(6) . ? N1 N2 1.393(6) . ? N1 C13 1.439(6) . ? N2 C11 1.306(7) . ? N3 C20 1.372(6) . ? N3 N4 1.384(7) . ? N3 C23 1.442(7) . ? N4 C21 1.321(7) . ? C1 C2 1.501(8) . ? C2 C3 1.393(8) . ? C2 C7 1.413(8) . ? C3 C4 1.401(8) . ? C3 C8 1.496(8) . ? C4 C5 1.399(9) . ? C5 C6 1.366(10) . ? C7 C6 1.411(9) . ? C8 C19 1.403(7) . ? C8 C9 1.437(7) . ? C9 C10 1.435(7) . ? C9 C11 1.448(7) . ? C11 C12 1.498(8) . ? C13 C14 1.398(8) . ? C13 C18 1.407(8) . ? C14 C15 1.390(8) . ? C15 C16 1.382(9) . ? C16 C17 1.370(9) . ? C17 C18 1.389(8) . ? C19 C20 1.420(8) . ? C19 C21 1.467(7) . ? C21 C22 1.494(8) . ? C23 C28 1.368(10) . ? C23 C24 1.409(9) . ? C24 C25 1.389(9) . ? C25 C26 1.390(12) . ? C26 C27 1.396(13) . ? C27 C28 1.392(9) . ? C31 Cl3A 1.72(2) . ? C31 Cl2 1.72(4) . ? C31 Cl2A 1.738(13) . ? C31 Cl1 1.787(11) . ? C31 Cl3 1.85(4) . ? 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 O3 Sn C30 107.5(2) . . ? O3 Sn C29 107.2(2) . . ? C30 Sn C29 143.7(2) . . ? O3 Sn O1 82.40(13) . 2_666 ? C30 Sn O1 99.2(2) . 2_666 ? C29 Sn O1 95.5(2) . 2_666 ? O3 Sn O4 78.88(13) . . ? C30 Sn O4 85.0(2) . . ? C29 Sn O4 91.5(2) . . ? O1 Sn O4 161.22(12) 2_666 . ? C1 O1 Sn 104.8(3) . 2_666 ? C10 O3 Sn 133.2(3) . . ? C20 O4 Sn 116.7(3) . . ? C10 N1 N2 112.2(4) . . ? C10 N1 C13 130.8(4) . . ? N2 N1 C13 117.0(4) . . ? C11 N2 N1 105.9(4) . . ? C20 N3 N4 112.5(4) . . ? C20 N3 C23 127.8(5) . . ? N4 N3 C23 119.5(4) . . ? C21 N4 N3 106.1(4) . . ? O2 C1 O1 122.3(5) . . ? O2 C1 C2 120.9(5) . . ? O1 C1 C2 116.8(4) . . ? C3 C2 C7 120.0(5) . . ? C3 C2 C1 122.7(5) . . ? C7 C2 C1 117.2(5) . . ? C2 C3 C4 119.9(5) . . ? C2 C3 C8 121.9(4) . . ? C4 C3 C8 117.9(5) . . ? C5 C4 C3 119.6(6) . . ? C6 C5 C4 121.3(5) . . ? C6 C7 C2 119.3(6) . . ? C5 C6 C7 119.9(6) . . ? C19 C8 C9 127.0(5) . . ? C19 C8 C3 118.8(4) . . ? C9 C8 C3 113.9(4) . . ? C10 C9 C8 129.2(4) . . ? C10 C9 C11 103.9(4) . . ? C8 C9 C11 126.9(4) . . ? O3 C10 N1 122.8(4) . . ? O3 C10 C9 130.5(5) . . ? N1 C10 C9 105.7(4) . . ? N2 C11 C9 112.3(5) . . ? N2 C11 C12 117.1(4) . . ? C9 C11 C12 130.4(4) . . ? C14 C13 C18 120.6(5) . . ? C14 C13 N1 122.1(5) . . ? C18 C13 N1 117.3(5) . . ? C15 C14 C13 118.1(5) . . ? C16 C15 C14 121.8(6) . . ? C17 C16 C15 119.4(5) . . ? C16 C17 C18 121.3(5) . . ? C17 C18 C13 118.8(6) . . ? C8 C19 C20 127.2(5) . . ? C8 C19 C21 128.2(5) . . ? C20 C19 C21 104.1(4) . . ? O4 C20 N3 122.3(5) . . ? O4 C20 C19 131.5(4) . . ? N3 C20 C19 106.2(5) . . ? N4 C21 C19 111.0(5) . . ? N4 C21 C22 118.2(4) . . ? C19 C21 C22 130.8(5) . . ? C28 C23 C24 121.6(6) . . ? C28 C23 N3 120.8(5) . . ? C24 C23 N3 117.6(6) . . ? C25 C24 C23 119.2(7) . . ? C26 C25 C24 119.6(7) . . ? C25 C26 C27 120.0(6) . . ? C28 C27 C26 120.9(8) . . ? C23 C28 C27 118.6(7) . . ? Cl3A C31 Cl2 117.9(14) . . ? Cl3A C31 Cl2A 112.7(8) . . ? Cl2 C31 Cl2A 15.3(19) . . ? Cl3A C31 Cl1 112.3(8) . . ? Cl2 C31 Cl1 94.8(21) . . ? Cl2A C31 Cl1 109.7(8) . . ? Cl3A C31 Cl3 12.2(14) . . ? Cl2 C31 Cl3 111.9(18) . . ? Cl2A C31 Cl3 109.9(14) . . ? Cl1 C31 Cl3 103.5(12) . . ? _refine_diff_density_max 1.338 _refine_diff_density_min -1.965 _refine_diff_density_rms 0.125 data_Cif-file structure of H2QBz _database_code_CSD 158777 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H22 N4 O4' _chemical_formula_weight 478.50 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.835(2) _cell_length_b 10.012(2) _cell_length_c 13.487(3) _cell_angle_alpha 108.97(3) _cell_angle_beta 101.97(3) _cell_angle_gamma 98.40(3) _cell_volume 1195.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 829 _cell_measurement_theta_min 5 _cell_measurement_theta_max 20 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method ? _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 IPDS(Stoe) _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4944 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.3654 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.39 _reflns_number_total 3768 _reflns_number_observed 817 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1696 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0174(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2072 _refine_ls_number_parameters 334 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2712 _refine_ls_R_factor_obs 0.0511 _refine_ls_wR_factor_all 0.1696 _refine_ls_wR_factor_obs 0.0860 _refine_ls_goodness_of_fit_all 0.722 _refine_ls_goodness_of_fit_obs 1.109 _refine_ls_restrained_S_all 0.832 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.0163(6) 0.5716(5) 0.4029(6) 0.066(2) Uani 1 d . . O2 O 0.0282(7) 0.8003(7) 0.5218(7) 0.084(3) Uani 1 d D . H1 H -0.0151(54) 0.7721(106) 0.5609(64) 0.101 Uiso 1 d D . O3 O 0.3405(6) 0.2518(5) 0.2378(5) 0.046(2) Uani 1 d D . H2 H 0.4181(44) 0.2963(70) 0.2678(43) 0.055 Uiso 1 d D . O4 O 0.1879(5) 0.2856(5) 0.4094(4) 0.045(2) Uani 1 d . . N1 N 0.1689(6) 0.2094(6) 0.0777(6) 0.041(2) Uani 1 d . . N2 N 0.0631(6) 0.2715(6) 0.0380(6) 0.047(2) Uani 1 d . . N3 N 0.3493(7) 0.4568(6) 0.5713(6) 0.038(2) Uani 1 d . . N4 N 0.4143(7) 0.6069(6) 0.6052(6) 0.042(2) Uani 1 d . . C1 C 0.0385(10) 0.6988(10) 0.4315(9) 0.056(3) Uani 1 d . . C2 C 0.1308(8) 0.7573(8) 0.3717(7) 0.037(3) Uani 1 d . . C3 C 0.2051(8) 0.6734(7) 0.3161(7) 0.040(2) Uani 1 d . . C4 C 0.2783(9) 0.7230(8) 0.2458(7) 0.053(3) Uani 1 d . . H4 H 0.3284(9) 0.6637(8) 0.2035(7) 0.063 Uiso 1 calc R . C5 C 0.2718(10) 0.8626(9) 0.2430(9) 0.062(3) Uani 1 d . . H5 H 0.3191(10) 0.8981(9) 0.1988(9) 0.074 Uiso 1 calc R . C6 C 0.1987(9) 0.9453(9) 0.3028(9) 0.067(4) Uani 1 d . . H6 H 0.1956(9) 1.0384(9) 0.2999(9) 0.080 Uiso 1 calc R . C7 C 0.1275(8) 0.8967(7) 0.3689(7) 0.041(2) Uani 1 d . . H7 H 0.0778(8) 0.9565(7) 0.4112(7) 0.050 Uiso 1 calc R . C8 C 0.2247(7) 0.5291(7) 0.3201(7) 0.035(2) Uani 1 d . . C9 C 0.1787(8) 0.4102(7) 0.2193(7) 0.037(2) Uani 1 d . . C10 C 0.2389(8) 0.2852(7) 0.1876(7) 0.036(2) Uani 1 d . . C11 C 0.0696(8) 0.3908(8) 0.1231(8) 0.045(2) Uani 1 d . . C12 C -0.0428(8) 0.4734(9) 0.1096(10) 0.060(3) Uani 1 d . . H12A H -0.0015(16) 0.5636(31) 0.1019(48) 0.090 Uiso 1 calc R . H12B H -0.0800(37) 0.4966(44) 0.1737(15) 0.090 Uiso 1 calc R . H12C H -0.1207(28) 0.4145(27) 0.0443(19) 0.090 Uiso 1 calc R . C13 C 0.1889(8) 0.0839(7) -0.0007(7) 0.037(2) Uani 1 d . . C14 C 0.2995(10) 0.0214(8) 0.0248(9) 0.065(3) Uani 1 d . . H14 H 0.3650(10) 0.0611(8) 0.0953(9) 0.078 Uiso 1 calc R . C15 C 0.3143(11) -0.1038(9) -0.0562(10) 0.078(4) Uani 1 d . . H15 H 0.3896(11) -0.1495(9) -0.0400(10) 0.093 Uiso 1 calc R . C16 C 0.2169(12) -0.1603(9) -0.1610(9) 0.074(3) Uani 1 d . . H16 H 0.2273(12) -0.2437(9) -0.2152(9) 0.089 Uiso 1 calc R . C17 C 0.1101(10) -0.0971(10) -0.1844(9) 0.065(3) Uani 1 d . . H17 H 0.0449(10) -0.1356(10) -0.2550(9) 0.078 Uiso 1 calc R . C18 C 0.0952(9) 0.0220(8) -0.1071(8) 0.052(3) Uani 1 d . . H18 H 0.0188(9) 0.0656(8) -0.1251(8) 0.062 Uiso 1 calc R . C19 C 0.2927(7) 0.5296(7) 0.4236(7) 0.035(2) Uani 1 d . . C20 C 0.2706(8) 0.4109(8) 0.4634(8) 0.043(3) Uani 1 d . . C21 C 0.3822(8) 0.6447(7) 0.5164(8) 0.041(2) Uani 1 d . . C22 C 0.4480(8) 0.7986(7) 0.5330(7) 0.055(3) Uani 1 d . . H22A H 0.3815(28) 0.8601(14) 0.5524(48) 0.082 Uiso 1 calc R . H22B H 0.4684(58) 0.8017(12) 0.4655(16) 0.082 Uiso 1 calc R . H22C H 0.5371(34) 0.8342(23) 0.5918(33) 0.082 Uiso 1 calc R . C23 C 0.3449(8) 0.3986(9) 0.6539(8) 0.047(3) Uani 1 d . . C24 C 0.3014(8) 0.2457(8) 0.6212(9) 0.060(3) Uani 1 d . . H24 H 0.2760(8) 0.1828(8) 0.5469(9) 0.071 Uiso 1 calc R . C25 C 0.2982(11) 0.1923(13) 0.7075(12) 0.085(4) Uani 1 d . . H25 H 0.2685(11) 0.0905(13) 0.6890(12) 0.102 Uiso 1 calc R . C26 C 0.3360(12) 0.2809(15) 0.8156(13) 0.101(5) Uani 1 d . . H26 H 0.3311(12) 0.2398(15) 0.8694(13) 0.121 Uiso 1 calc R . C27 C 0.3821(10) 0.4324(12) 0.8470(10) 0.083(4) Uani 1 d . . H27 H 0.4083(10) 0.4947(12) 0.9215(10) 0.099 Uiso 1 calc R . C28 C 0.3877(9) 0.4869(11) 0.7663(9) 0.058(3) Uani 1 d . . H28 H 0.4220(9) 0.5885(11) 0.7867(9) 0.069 Uiso 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 O1 0.071(4) 0.032(3) 0.095(6) 0.014(4) 0.048(4) 0.002(3) O2 0.082(5) 0.068(4) 0.089(7) 0.010(5) 0.046(5) -0.010(4) O3 0.035(3) 0.032(3) 0.058(5) 0.004(3) 0.005(4) 0.009(2) O4 0.055(3) 0.025(2) 0.045(5) 0.004(3) 0.015(3) -0.002(2) N1 0.035(4) 0.037(3) 0.049(6) 0.018(4) 0.004(4) 0.009(3) N2 0.044(4) 0.041(3) 0.053(6) 0.015(4) 0.007(4) 0.017(3) N3 0.038(4) 0.038(3) 0.039(6) 0.016(4) 0.006(4) 0.009(3) N4 0.046(4) 0.033(3) 0.039(6) 0.008(4) 0.006(4) 0.002(3) C1 0.063(6) 0.052(5) 0.055(9) 0.012(7) 0.033(6) 0.011(5) C2 0.025(4) 0.041(5) 0.048(7) 0.022(5) 0.005(5) 0.006(4) C3 0.036(5) 0.034(4) 0.056(7) 0.023(5) 0.013(5) 0.013(4) C4 0.077(7) 0.038(4) 0.050(7) 0.013(5) 0.038(6) 0.013(4) C5 0.071(7) 0.040(5) 0.082(9) 0.038(6) 0.018(6) 0.004(5) C6 0.065(7) 0.036(5) 0.101(11) 0.039(7) 0.013(7) 0.002(5) C7 0.043(5) 0.021(3) 0.053(7) 0.000(5) 0.015(5) 0.020(3) C8 0.028(4) 0.031(4) 0.050(6) 0.016(4) 0.014(5) 0.009(3) C9 0.037(5) 0.034(4) 0.051(6) 0.022(4) 0.018(5) 0.015(3) C10 0.025(5) 0.037(4) 0.045(6) 0.023(5) 0.003(5) 0.000(4) C11 0.038(5) 0.047(5) 0.059(7) 0.026(5) 0.019(5) 0.015(4) C12 0.045(6) 0.061(5) 0.087(9) 0.035(6) 0.022(6) 0.028(4) C13 0.041(5) 0.031(4) 0.038(6) 0.012(4) 0.010(5) 0.008(4) C14 0.065(6) 0.044(4) 0.079(9) 0.007(5) 0.020(6) 0.023(5) C15 0.083(8) 0.055(5) 0.100(11) 0.014(7) 0.045(8) 0.038(5) C16 0.086(9) 0.052(5) 0.053(9) -0.009(6) 0.009(7) 0.005(6) C17 0.048(6) 0.067(6) 0.060(9) 0.011(6) -0.004(6) 0.011(5) C18 0.053(6) 0.042(5) 0.050(7) 0.006(5) 0.009(6) 0.013(4) C19 0.028(5) 0.035(4) 0.049(7) 0.021(4) 0.012(5) 0.009(3) C20 0.040(5) 0.039(5) 0.065(9) 0.030(6) 0.028(6) 0.016(4) C21 0.028(4) 0.038(4) 0.054(7) 0.015(5) 0.010(5) 0.005(3) C22 0.042(5) 0.032(4) 0.077(8) 0.018(5) 0.000(5) -0.003(4) C23 0.032(5) 0.059(5) 0.059(9) 0.033(7) 0.010(5) 0.015(4) C24 0.058(6) 0.055(5) 0.066(9) 0.033(6) 0.005(6) 0.005(4) C25 0.070(8) 0.095(8) 0.118(13) 0.078(10) 0.024(8) 0.018(6) C26 0.088(9) 0.145(13) 0.117(15) 0.090(13) 0.055(10) 0.037(8) C27 0.074(8) 0.112(9) 0.069(11) 0.043(9) 0.019(7) 0.020(6) C28 0.046(6) 0.083(6) 0.049(8) 0.037(7) 0.005(5) 0.014(5) _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 O1 C1 1.207(9) . ? O2 C1 1.343(13) . ? O3 C10 1.238(8) . ? O4 C20 1.276(8) . ? N1 N2 1.390(8) . ? N1 C10 1.392(9) . ? N1 C13 1.425(10) . ? N2 C11 1.343(10) . ? N3 C20 1.387(11) . ? N3 C23 1.420(10) . ? N3 N4 1.424(7) . ? N4 C21 1.361(10) . ? C1 C2 1.507(11) . ? C2 C3 1.342(12) . ? C2 C7 1.413(10) . ? C3 C4 1.466(10) . ? C3 C8 1.502(9) . ? C4 C5 1.420(11) . ? C5 C6 1.355(13) . ? C6 C7 1.401(12) . ? C8 C19 1.415(10) . ? C8 C9 1.416(11) . ? C9 C11 1.438(10) . ? C9 C10 1.440(11) . ? C11 C12 1.490(10) . ? C13 C14 1.369(11) . ? C13 C18 1.414(11) . ? C14 C15 1.420(13) . ? C15 C16 1.412(13) . ? C16 C17 1.338(12) . ? C17 C18 1.355(13) . ? C19 C21 1.406(12) . ? C19 C20 1.461(8) . ? C21 C22 1.506(7) . ? C23 C24 1.418(11) . ? C23 C28 1.418(13) . ? C24 C25 1.434(13) . ? C25 C26 1.37(2) . ? C26 C27 1.409(14) . ? C27 C28 1.375(12) . ? 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 N2 N1 C10 113.0(7) . . ? N2 N1 C13 115.1(7) . . ? C10 N1 C13 131.8(7) . . ? C11 N2 N1 104.6(7) . . ? C20 N3 C23 132.6(6) . . ? C20 N3 N4 107.4(5) . . ? C23 N3 N4 117.4(7) . . ? C21 N4 N3 107.1(6) . . ? O1 C1 O2 123.2(8) . . ? O1 C1 C2 122.9(11) . . ? O2 C1 C2 113.8(7) . . ? C3 C2 C7 121.5(7) . . ? C3 C2 C1 120.0(7) . . ? C7 C2 C1 118.3(10) . . ? C2 C3 C4 119.7(6) . . ? C2 C3 C8 125.8(7) . . ? C4 C3 C8 114.6(8) . . ? C5 C4 C3 117.8(9) . . ? C6 C5 C4 120.5(8) . . ? C5 C6 C7 121.5(7) . . ? C6 C7 C2 119.0(9) . . ? C19 C8 C9 127.8(6) . . ? C19 C8 C3 115.9(7) . . ? C9 C8 C3 116.2(7) . . ? C8 C9 C11 128.5(7) . . ? C8 C9 C10 127.1(8) . . ? C11 C9 C10 104.2(7) . . ? O3 C10 N1 123.5(8) . . ? O3 C10 C9 130.9(8) . . ? N1 C10 C9 105.3(7) . . ? N2 C11 C9 112.9(7) . . ? N2 C11 C12 117.4(8) . . ? C9 C11 C12 129.3(9) . . ? C14 C13 C18 118.6(8) . . ? C14 C13 N1 121.0(8) . . ? C18 C13 N1 120.4(7) . . ? C13 C14 C15 118.7(10) . . ? C16 C15 C14 119.9(10) . . ? C17 C16 C15 120.5(11) . . ? C16 C17 C18 119.8(9) . . ? C17 C18 C13 122.5(8) . . ? C21 C19 C8 129.8(6) . . ? C21 C19 C20 102.9(7) . . ? C8 C19 C20 126.8(6) . . ? O4 C20 N3 124.6(6) . . ? O4 C20 C19 125.9(8) . . ? N3 C20 C19 109.5(6) . . ? N4 C21 C19 112.8(5) . . ? N4 C21 C22 115.9(7) . . ? C19 C21 C22 131.3(7) . . ? C24 C23 C28 119.8(8) . . ? C24 C23 N3 117.7(9) . . ? C28 C23 N3 122.4(7) . . ? C23 C24 C25 115.6(11) . . ? C26 C25 C24 123.2(10) . . ? C25 C26 C27 120.4(10) . . ? C28 C27 C26 117.7(12) . . ? C27 C28 C23 123.0(9) . . ? _refine_diff_density_max 0.152 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.037