Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2003 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _journal_volume ? _journal_year ? _journal_page_first ? loop_ _publ_author_name 'Julia Pérez-Prieto' 'Raquel E. Galian' 'Miguel A. Miranda' 'Maria C. Morant-Minana' _publ_contact_author_name 'Dr Julia Pérez-Prieto' _publ_contact_author_address ; Dr Julia Pérez-Prieto Química Orgánica/ICMOL Universidad de Valencia Av. Vicent Andrés Estellés sn Burjassot 46100 SPAIN ; _publ_contact_author_email JULIA.PEREZ@UV.ES _publ_section_title ; Steady-state and time-resolved studies on the formation of skatolyl radical photosensitized by 2-benzoylthiophene ; # CIF produced by WinGX routine CIF_UPDATE # Created on 2003-04-04 at 19:33:13 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : g:\xprogs\wingx\files\archive.dat # CIF files read : 2003va01 header sg sortav struct data_2003va01 _database_code_CSD 213672 _audit_creation_date 2003-04-04T19:33:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 2003va01jp01 _chemical_formula_moiety 'C20 H15 N O S' _chemical_formula_sum 'C20 H15 N1 O1 S1' _chemical_formula_weight 317.39 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 30.3283(5) _cell_length_b 12.9666(2) _cell_length_c 7.8988(1) _cell_angle_alpha 90 _cell_angle_beta 96.205(1) _cell_angle_gamma 90 _cell_volume 3088.04(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 6162 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 74.48 _cell_measurement_wavelength 1.54184 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.927 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_orient_matrix_type X==UH _diffrn_orient_matrix_UB_11 0.00372 _diffrn_orient_matrix_UB_12 -0.03275 _diffrn_orient_matrix_UB_13 0.00373 _diffrn_orient_matrix_UB_21 0.0546 _diffrn_orient_matrix_UB_22 0 _diffrn_orient_matrix_UB_23 -0.05447 _diffrn_orient_matrix_UB_31 0.08982 _diffrn_orient_matrix_UB_32 0.0065 _diffrn_orient_matrix_UB_33 0.09004 _diffrn_measurement_device '135mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD2000 _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.113 _diffrn_reflns_av_unetI/netI 0.1628 _diffrn_reflns_number 56768 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 72.54 _diffrn_reflns_theta_full 72.54 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 5987 _reflns_number_gt 4277 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0000P)^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 5987 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1838 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.439 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.41146(8) -0.4581(2) 0.9170(3) 0.0457(6) Uani 1 1 d . . . H1 H 0.4191(11) -0.516(3) 0.906(5) 0.053(11) Uiso 1 1 d . . . C2 C 0.43047(9) -0.3671(2) 0.8680(4) 0.0440(7) Uani 1 1 d . . . C3 C 0.40268(9) -0.2851(2) 0.8984(4) 0.0443(6) Uani 1 1 d . . . C4 C 0.36539(9) -0.3295(2) 0.9673(4) 0.0444(6) Uani 1 1 d . . . C5 C 0.32730(9) -0.2866(3) 1.0286(4) 0.0494(7) Uani 1 1 d . . . H5 H 0.3218 -0.2146 1.0216 0.059 Uiso 1 1 calc R . . C6 C 0.29845(10) -0.3519(3) 1.0986(4) 0.0519(8) Uani 1 1 d . . . H6 H 0.2731 -0.324 1.143 0.062 Uiso 1 1 calc R . . C7 C 0.30571(10) -0.4590(3) 1.1057(4) 0.0530(8) Uani 1 1 d . . . H7 H 0.2847 -0.502 1.1523 0.064 Uiso 1 1 calc R . . C8 C 0.34234(10) -0.5033(3) 1.0472(4) 0.0479(7) Uani 1 1 d . . . H8 H 0.3473 -0.5756 1.0536 0.058 Uiso 1 1 calc R . . C9 C 0.37205(9) -0.4367(2) 0.9776(4) 0.0446(7) Uani 1 1 d . . . C10 C 0.41030(10) -0.1730(2) 0.8724(4) 0.0493(7) Uani 1 1 d . . . H10A H 0.4332 -0.1482 0.9597 0.074 Uiso 1 1 calc R . . H10B H 0.3827 -0.1351 0.881 0.074 Uiso 1 1 calc R . . H10C H 0.42 -0.1621 0.7594 0.074 Uiso 1 1 calc R . . C11 C 0.47292(10) -0.3691(2) 0.8025(4) 0.0440(6) Uani 1 1 d . . . S12 S 0.49813(2) -0.25876(6) 0.73700(10) 0.0444(2) Uani 1 1 d . . . C13 C 0.54342(9) -0.3271(2) 0.6834(4) 0.0445(7) Uani 1 1 d . . . C14 C 0.53922(10) -0.4308(2) 0.7170(4) 0.0476(7) Uani 1 1 d . . . H14 H 0.5611 -0.4807 0.698 0.057 Uiso 1 1 calc R . . C15 C 0.49946(10) -0.4546(3) 0.7817(4) 0.0485(7) Uani 1 1 d . . . H15 H 0.4913 -0.5228 0.8091 0.058 Uiso 1 1 calc R . . C16 C 0.57954(10) -0.2683(2) 0.6224(4) 0.0449(7) Uani 1 1 d . . . O17 O 0.57710(7) -0.17354(17) 0.6158(3) 0.0515(5) Uani 1 1 d . . . C18 C 0.62025(9) -0.3214(2) 0.5752(4) 0.0447(7) Uani 1 1 d . . . C19 C 0.66122(10) -0.2754(3) 0.6282(4) 0.0508(7) Uani 1 1 d . . . H19 H 0.6624 -0.2134 0.6926 0.061 Uiso 1 1 calc R . . C20 C 0.69970(10) -0.3200(3) 0.5868(4) 0.0540(8) Uani 1 1 d . . . H20 H 0.7274 -0.2889 0.624 0.065 Uiso 1 1 calc R . . C21 C 0.69850(10) -0.4100(3) 0.4911(4) 0.0546(8) Uani 1 1 d . . . H21 H 0.7253 -0.4404 0.4634 0.066 Uiso 1 1 calc R . . C22 C 0.65810(11) -0.4552(3) 0.4363(4) 0.0520(7) Uani 1 1 d . . . H22 H 0.6571 -0.5161 0.3691 0.062 Uiso 1 1 calc R . . C23 C 0.61876(10) -0.4113(3) 0.4797(4) 0.0474(7) Uani 1 1 d . . . H23 H 0.5911 -0.443 0.4439 0.057 Uiso 1 1 calc R . . N51 N 0.09643(8) -0.4684(2) 0.5051(3) 0.0430(6) Uani 1 1 d . . . H51 H 0.0851(9) -0.527(3) 0.494(4) 0.041(9) Uiso 1 1 d . . . C52 C 0.07865(9) -0.3785(2) 0.4296(4) 0.0425(6) Uani 1 1 d . . . C53 C 0.10869(9) -0.2983(2) 0.4649(4) 0.0424(6) Uani 1 1 d . . . C54 C 0.14690(9) -0.3425(2) 0.5611(4) 0.0439(6) Uani 1 1 d . . . C55 C 0.18743(10) -0.3009(3) 0.6342(4) 0.0499(7) Uani 1 1 d . . . H55 H 0.194 -0.2299 0.6205 0.06 Uiso 1 1 calc R . . C56 C 0.21725(10) -0.3645(3) 0.7255(4) 0.0538(8) Uani 1 1 d . . . H56 H 0.2449 -0.3375 0.7735 0.065 Uiso 1 1 calc R . . C57 C 0.20756(10) -0.4693(3) 0.7494(4) 0.0508(7) Uani 1 1 d . . . H57 H 0.2287 -0.5113 0.8147 0.061 Uiso 1 1 calc R . . C58 C 0.16796(9) -0.5125(2) 0.6801(4) 0.0463(7) Uani 1 1 d . . . H58 H 0.1614 -0.5832 0.6966 0.056 Uiso 1 1 calc R . . C59 C 0.13804(9) -0.4475(2) 0.5847(4) 0.0422(6) Uani 1 1 d . . . C60 C 0.10230(10) -0.1864(2) 0.4251(4) 0.0476(7) Uani 1 1 d . . . H60A H 0.0891 -0.1785 0.307 0.071 Uiso 1 1 calc R . . H60B H 0.1311 -0.1512 0.4401 0.071 Uiso 1 1 calc R . . H60C H 0.0826 -0.1561 0.502 0.071 Uiso 1 1 calc R . . C61 C 0.03545(9) -0.3791(2) 0.3333(4) 0.0431(6) Uani 1 1 d . . . S62 S 0.01131(2) -0.26799(6) 0.24474(10) 0.0433(2) Uani 1 1 d . . . C63 C -0.03508(9) -0.3344(2) 0.1585(4) 0.0434(6) Uani 1 1 d . . . C64 C -0.03195(9) -0.4373(2) 0.1989(4) 0.0454(7) Uani 1 1 d . . . H64 H -0.0546 -0.4858 0.1637 0.055 Uiso 1 1 calc R . . C65 C 0.00782(9) -0.4640(3) 0.2971(4) 0.0458(7) Uani 1 1 d . . . H65 H 0.0151 -0.5322 0.3346 0.055 Uiso 1 1 calc R . . C66 C -0.07062(9) -0.2737(2) 0.0675(4) 0.0425(6) Uani 1 1 d . . . O67 O -0.06750(7) -0.17869(17) 0.0643(3) 0.0487(5) Uani 1 1 d . . . C68 C -0.11138(9) -0.3253(2) -0.0153(4) 0.0433(6) Uani 1 1 d . . . C69 C -0.15193(9) -0.2764(3) -0.0056(4) 0.0475(7) Uani 1 1 d . . . H69 H -0.1529 -0.2128 0.0536 0.057 Uiso 1 1 calc R . . C70 C -0.19078(10) -0.3201(3) -0.0818(4) 0.0530(8) Uani 1 1 d . . . H70 H -0.2184 -0.2867 -0.0749 0.064 Uiso 1 1 calc R . . C71 C -0.18909(10) -0.4136(3) -0.1691(4) 0.0530(8) Uani 1 1 d . . . H71 H -0.2157 -0.4438 -0.2214 0.064 Uiso 1 1 calc R . . C72 C -0.14924(9) -0.4621(3) -0.1798(4) 0.0470(7) Uani 1 1 d . . . H72 H -0.1483 -0.5253 -0.2401 0.056 Uiso 1 1 calc R . . C73 C -0.11015(9) -0.4188(2) -0.1024(4) 0.0443(7) Uani 1 1 d . . . H73 H -0.0826 -0.4529 -0.1088 0.053 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 N1 0.0555(14) 0.0331(14) 0.0489(15) -0.0038(12) 0.0080(10) 0.0012(11) C2 0.0558(16) 0.0347(16) 0.0408(15) 0.0010(12) 0.0024(12) -0.0003(12) C3 0.0512(14) 0.0370(16) 0.0441(16) 0.0013(13) 0.0023(11) 0.0009(12) C4 0.0526(15) 0.0387(16) 0.0410(15) -0.0005(13) 0.0011(11) 0.0023(12) C5 0.0533(15) 0.0443(18) 0.0500(18) -0.0011(15) 0.0023(12) 0.0047(13) C6 0.0484(15) 0.056(2) 0.0517(18) -0.0014(15) 0.0053(12) 0.0050(14) C7 0.0494(15) 0.057(2) 0.0527(18) 0.0021(16) 0.0046(13) -0.0068(14) C8 0.0579(16) 0.0392(17) 0.0469(17) -0.0002(14) 0.0064(12) -0.0036(13) C9 0.0497(15) 0.0403(17) 0.0437(16) -0.0025(13) 0.0042(11) -0.0014(12) C10 0.0562(16) 0.0396(18) 0.0512(18) 0.0009(14) 0.0021(13) 0.0025(13) C11 0.0548(15) 0.0372(16) 0.0398(15) 0.0009(13) 0.0042(11) -0.0001(12) S12 0.0541(4) 0.0341(4) 0.0451(4) 0.0003(3) 0.0054(3) 0.0006(3) C13 0.0575(16) 0.0351(16) 0.0410(15) 0.0006(13) 0.0055(12) 0.0001(12) C14 0.0579(16) 0.0364(17) 0.0489(17) -0.0006(14) 0.0077(12) 0.0052(12) C15 0.0647(17) 0.0331(17) 0.0488(17) 0.0010(13) 0.0119(13) -0.0001(13) C16 0.0585(16) 0.0366(17) 0.0391(16) -0.0016(12) 0.0027(12) -0.0025(12) O17 0.0627(12) 0.0340(12) 0.0576(13) 0.0006(10) 0.0049(10) -0.0028(9) C18 0.0524(15) 0.0402(17) 0.0417(15) 0.0040(13) 0.0053(11) -0.0010(12) C19 0.0631(17) 0.0423(18) 0.0470(18) 0.0053(14) 0.0057(13) -0.0045(14) C20 0.0529(16) 0.057(2) 0.0514(18) 0.0072(16) 0.0031(13) -0.0033(14) C21 0.0570(17) 0.057(2) 0.0507(18) 0.0109(16) 0.0117(13) 0.0066(15) C22 0.0710(19) 0.0429(19) 0.0437(17) 0.0032(14) 0.0129(14) 0.0048(14) C23 0.0569(16) 0.0423(18) 0.0434(16) 0.0042(13) 0.0069(12) -0.0020(13) N51 0.0498(12) 0.0330(13) 0.0463(14) 0.0011(11) 0.0059(10) -0.0021(10) C52 0.0483(14) 0.0374(16) 0.0431(15) -0.0025(13) 0.0109(11) 0.0007(11) C53 0.0499(14) 0.0344(16) 0.0442(16) 0.0004(13) 0.0108(11) -0.0032(11) C54 0.0496(14) 0.0402(17) 0.0427(15) -0.0035(13) 0.0087(11) -0.0026(12) C55 0.0536(15) 0.0454(19) 0.0510(17) -0.0010(15) 0.0073(12) -0.0068(13) C56 0.0493(15) 0.058(2) 0.0529(18) 0.0000(16) 0.0019(13) -0.0054(14) C57 0.0504(15) 0.053(2) 0.0485(17) 0.0017(15) 0.0044(12) 0.0027(13) C58 0.0554(16) 0.0402(17) 0.0436(16) 0.0036(13) 0.0075(12) 0.0023(12) C59 0.0480(14) 0.0381(16) 0.0415(15) -0.0006(12) 0.0096(11) -0.0002(11) C60 0.0533(15) 0.0394(18) 0.0512(17) -0.0031(14) 0.0106(12) -0.0045(12) C61 0.0508(15) 0.0381(17) 0.0421(15) -0.0018(13) 0.0123(11) -0.0006(11) S62 0.0491(4) 0.0357(4) 0.0457(4) 0.0007(3) 0.0073(3) -0.0009(3) C63 0.0510(15) 0.0371(16) 0.0432(15) 0.0011(13) 0.0095(11) 0.0021(12) C64 0.0501(15) 0.0381(17) 0.0485(16) 0.0001(13) 0.0072(12) -0.0044(12) C65 0.0516(15) 0.0370(17) 0.0491(17) -0.0007(14) 0.0074(12) -0.0007(12) C66 0.0475(14) 0.0396(17) 0.0421(16) 0.0028(13) 0.0122(11) 0.0031(12) O67 0.0575(11) 0.0344(12) 0.0545(13) 0.0010(10) 0.0080(9) 0.0023(9) C68 0.0501(14) 0.0396(17) 0.0409(15) 0.0026(13) 0.0081(11) -0.0001(12) C69 0.0534(15) 0.0456(19) 0.0449(17) 0.0018(14) 0.0121(12) 0.0019(13) C70 0.0485(15) 0.058(2) 0.0535(18) 0.0059(16) 0.0092(13) 0.0045(14) C71 0.0517(16) 0.057(2) 0.0506(18) 0.0031(16) 0.0066(13) -0.0059(14) C72 0.0547(15) 0.0464(18) 0.0405(15) 0.0029(14) 0.0075(11) -0.0043(13) C73 0.0495(14) 0.0409(17) 0.0433(15) 0.0025(13) 0.0092(11) 0.0032(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C9 1.363(4) . ? N1 C2 1.387(4) . ? N1 H1 0.79(4) . ? C2 C3 1.394(4) . ? C2 C11 1.439(4) . ? C3 C4 1.428(4) . ? C3 C10 1.490(4) . ? C4 C9 1.407(4) . ? C4 C5 1.414(4) . ? C5 C6 1.375(5) . ? C5 H5 0.95 . ? C6 C7 1.407(5) . ? C6 H6 0.95 . ? C7 C8 1.374(4) . ? C7 H7 0.95 . ? C8 C9 1.402(4) . ? C8 H8 0.95 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 C15 1.390(4) . ? C11 S12 1.728(3) . ? S12 C13 1.725(3) . ? C13 C14 1.379(4) . ? C13 C16 1.458(4) . ? C14 C15 1.395(4) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 O17 1.232(4) . ? C16 C18 1.495(4) . ? C18 C23 1.387(4) . ? C18 C19 1.401(4) . ? C19 C20 1.373(5) . ? C19 H19 0.95 . ? C20 C21 1.389(5) . ? C20 H20 0.95 . ? C21 C22 1.385(5) . ? C21 H21 0.95 . ? C22 C23 1.398(4) . ? C22 H22 0.95 . ? C23 H23 0.95 . ? N51 C59 1.375(4) . ? N51 C52 1.392(4) . ? N51 H51 0.83(3) . ? C52 C53 1.391(4) . ? C52 C61 1.442(4) . ? C53 C54 1.434(4) . ? C53 C60 1.493(4) . ? C54 C59 1.405(4) . ? C54 C55 1.408(4) . ? C55 C56 1.371(5) . ? C55 H55 0.95 . ? C56 C57 1.407(5) . ? C56 H56 0.95 . ? C57 C58 1.383(4) . ? C57 H57 0.95 . ? C58 C59 1.397(4) . ? C58 H58 0.95 . ? C60 H60A 0.98 . ? C60 H60B 0.98 . ? C60 H60C 0.98 . ? C61 C65 1.395(4) . ? C61 S62 1.729(3) . ? S62 C63 1.726(3) . ? C63 C64 1.372(4) . ? C63 C66 1.460(4) . ? C64 C65 1.405(4) . ? C64 H64 0.95 . ? C65 H65 0.95 . ? C66 O67 1.236(4) . ? C66 C68 1.493(4) . ? C68 C69 1.393(4) . ? C68 C73 1.397(4) . ? C69 C70 1.385(4) . ? C69 H69 0.95 . ? C70 C71 1.399(5) . ? C70 H70 0.95 . ? C71 C72 1.373(4) . ? C71 H71 0.95 . ? C72 C73 1.392(4) . ? C72 H72 0.95 . ? C73 H73 0.95 . ? 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 C9 N1 C2 109.4(3) . . ? C9 N1 H1 121(3) . . ? C2 N1 H1 130(3) . . ? N1 C2 C3 108.9(3) . . ? N1 C2 C11 120.0(3) . . ? C3 C2 C11 131.1(3) . . ? C2 C3 C4 106.1(3) . . ? C2 C3 C10 127.9(3) . . ? C4 C3 C10 125.9(3) . . ? C9 C4 C5 119.1(3) . . ? C9 C4 C3 107.8(3) . . ? C5 C4 C3 133.1(3) . . ? C6 C5 C4 118.4(3) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 121.9(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 116.8(3) . . ? C7 C8 H8 121.6 . . ? C9 C8 H8 121.6 . . ? N1 C9 C8 129.6(3) . . ? N1 C9 C4 107.9(3) . . ? C8 C9 C4 122.5(3) . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C11 C2 127.5(3) . . ? C15 C11 S12 110.1(2) . . ? C2 C11 S12 122.3(2) . . ? C13 S12 C11 92.19(15) . . ? C14 C13 C16 131.4(3) . . ? C14 C13 S12 111.1(2) . . ? C16 C13 S12 117.4(2) . . ? C13 C14 C15 112.8(3) . . ? C13 C14 H14 123.6 . . ? C15 C14 H14 123.6 . . ? C11 C15 C14 113.7(3) . . ? C11 C15 H15 123.2 . . ? C14 C15 H15 123.2 . . ? O17 C16 C13 119.4(3) . . ? O17 C16 C18 119.7(3) . . ? C13 C16 C18 120.8(3) . . ? C23 C18 C19 119.8(3) . . ? C23 C18 C16 122.9(3) . . ? C19 C18 C16 117.3(3) . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 119.8(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22 120 . . ? C23 C22 H22 120 . . ? C18 C23 C22 119.8(3) . . ? C18 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C59 N51 C52 109.0(3) . . ? C59 N51 H51 125(2) . . ? C52 N51 H51 126(2) . . ? C53 C52 N51 109.0(2) . . ? C53 C52 C61 130.4(3) . . ? N51 C52 C61 120.6(3) . . ? C52 C53 C54 106.4(3) . . ? C52 C53 C60 128.1(3) . . ? C54 C53 C60 125.4(3) . . ? C59 C54 C55 119.2(3) . . ? C59 C54 C53 107.6(2) . . ? C55 C54 C53 133.1(3) . . ? C56 C55 C54 118.8(3) . . ? C56 C55 H55 120.6 . . ? C54 C55 H55 120.6 . . ? C55 C56 C57 121.1(3) . . ? C55 C56 H56 119.5 . . ? C57 C56 H56 119.5 . . ? C58 C57 C56 121.5(3) . . ? C58 C57 H57 119.2 . . ? C56 C57 H57 119.2 . . ? C57 C58 C59 117.1(3) . . ? C57 C58 H58 121.5 . . ? C59 C58 H58 121.5 . . ? N51 C59 C58 129.7(3) . . ? N51 C59 C54 108.0(2) . . ? C58 C59 C54 122.2(3) . . ? C53 C60 H60A 109.5 . . ? C53 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C53 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C65 C61 C52 127.1(3) . . ? C65 C61 S62 110.9(2) . . ? C52 C61 S62 122.0(2) . . ? C63 S62 C61 92.03(14) . . ? C64 C63 C66 131.9(3) . . ? C64 C63 S62 111.1(2) . . ? C66 C63 S62 116.9(2) . . ? C63 C64 C65 113.7(3) . . ? C63 C64 H64 123.1 . . ? C65 C64 H64 123.1 . . ? C61 C65 C64 112.3(3) . . ? C61 C65 H65 123.9 . . ? C64 C65 H65 123.9 . . ? O67 C66 C63 119.6(3) . . ? O67 C66 C68 120.0(3) . . ? C63 C66 C68 120.4(3) . . ? C69 C68 C73 119.6(3) . . ? C69 C68 C66 117.8(3) . . ? C73 C68 C66 122.7(3) . . ? C70 C69 C68 120.3(3) . . ? C70 C69 H69 119.9 . . ? C68 C69 H69 119.9 . . ? C69 C70 C71 119.6(3) . . ? C69 C70 H70 120.2 . . ? C71 C70 H70 120.2 . . ? C72 C71 C70 120.4(3) . . ? C72 C71 H71 119.8 . . ? C70 C71 H71 119.8 . . ? C71 C72 C73 120.2(3) . . ? C71 C72 H72 119.9 . . ? C73 C72 H72 119.9 . . ? C72 C73 C68 120.0(3) . . ? C72 C73 H73 120 . . ? C68 C73 H73 120 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 C3 0.2(3) . . . . ? C9 N1 C2 C11 178.8(3) . . . . ? N1 C2 C3 C4 -0.4(3) . . . . ? C11 C2 C3 C4 -178.8(3) . . . . ? N1 C2 C3 C10 177.2(3) . . . . ? C11 C2 C3 C10 -1.1(6) . . . . ? C2 C3 C4 C9 0.5(3) . . . . ? C10 C3 C4 C9 -177.2(3) . . . . ? C2 C3 C4 C5 177.3(3) . . . . ? C10 C3 C4 C5 -0.4(5) . . . . ? C9 C4 C5 C6 0.9(4) . . . . ? C3 C4 C5 C6 -175.6(3) . . . . ? C4 C5 C6 C7 -1.6(5) . . . . ? C5 C6 C7 C8 1.6(5) . . . . ? C6 C7 C8 C9 -0.8(5) . . . . ? C2 N1 C9 C8 -177.2(3) . . . . ? C2 N1 C9 C4 0.1(3) . . . . ? C7 C8 C9 N1 177.1(3) . . . . ? C7 C8 C9 C4 0.1(5) . . . . ? C5 C4 C9 N1 -177.7(3) . . . . ? C3 C4 C9 N1 -0.4(3) . . . . ? C5 C4 C9 C8 -0.2(5) . . . . ? C3 C4 C9 C8 177.1(3) . . . . ? N1 C2 C11 C15 -0.8(5) . . . . ? C3 C2 C11 C15 177.4(3) . . . . ? N1 C2 C11 S12 179.3(2) . . . . ? C3 C2 C11 S12 -2.6(5) . . . . ? C15 C11 S12 C13 -0.1(2) . . . . ? C2 C11 S12 C13 179.9(3) . . . . ? C11 S12 C13 C14 -0.7(2) . . . . ? C11 S12 C13 C16 -177.2(2) . . . . ? C16 C13 C14 C15 177.2(3) . . . . ? S12 C13 C14 C15 1.3(4) . . . . ? C2 C11 C15 C14 -179.1(3) . . . . ? S12 C11 C15 C14 0.8(4) . . . . ? C13 C14 C15 C11 -1.4(4) . . . . ? C14 C13 C16 O17 -173.8(3) . . . . ? S12 C13 C16 O17 2.0(4) . . . . ? C14 C13 C16 C18 3.5(5) . . . . ? S12 C13 C16 C18 179.2(2) . . . . ? O17 C16 C18 C23 -138.7(3) . . . . ? C13 C16 C18 C23 44.0(4) . . . . ? O17 C16 C18 C19 39.8(4) . . . . ? C13 C16 C18 C19 -137.5(3) . . . . ? C23 C18 C19 C20 -0.7(5) . . . . ? C16 C18 C19 C20 -179.2(3) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C19 C20 C21 C22 0.2(5) . . . . ? C20 C21 C22 C23 -1.1(5) . . . . ? C19 C18 C23 C22 -0.2(5) . . . . ? C16 C18 C23 C22 178.2(3) . . . . ? C21 C22 C23 C18 1.1(5) . . . . ? C59 N51 C52 C53 -1.6(3) . . . . ? C59 N51 C52 C61 178.4(3) . . . . ? N51 C52 C53 C54 2.0(3) . . . . ? C61 C52 C53 C54 -178.0(3) . . . . ? N51 C52 C53 C60 -173.6(3) . . . . ? C61 C52 C53 C60 6.4(5) . . . . ? C52 C53 C54 C59 -1.7(3) . . . . ? C60 C53 C54 C59 174.0(3) . . . . ? C52 C53 C54 C55 -179.1(3) . . . . ? C60 C53 C54 C55 -3.4(5) . . . . ? C59 C54 C55 C56 0.5(5) . . . . ? C53 C54 C55 C56 177.7(3) . . . . ? C54 C55 C56 C57 -1.2(5) . . . . ? C55 C56 C57 C58 0.9(5) . . . . ? C56 C57 C58 C59 0.2(5) . . . . ? C52 N51 C59 C58 178.3(3) . . . . ? C52 N51 C59 C54 0.5(3) . . . . ? C57 C58 C59 N51 -178.5(3) . . . . ? C57 C58 C59 C54 -1.0(5) . . . . ? C55 C54 C59 N51 178.6(3) . . . . ? C53 C54 C59 N51 0.7(3) . . . . ? C55 C54 C59 C58 0.6(5) . . . . ? C53 C54 C59 C58 -177.2(3) . . . . ? C53 C52 C61 C65 177.1(3) . . . . ? N51 C52 C61 C65 -3.0(5) . . . . ? C53 C52 C61 S62 -2.6(5) . . . . ? N51 C52 C61 S62 177.4(2) . . . . ? C65 C61 S62 C63 -0.5(2) . . . . ? C52 C61 S62 C63 179.2(3) . . . . ? C61 S62 C63 C64 0.8(2) . . . . ? C61 S62 C63 C66 177.4(2) . . . . ? C66 C63 C64 C65 -176.8(3) . . . . ? S62 C63 C64 C65 -0.8(4) . . . . ? C52 C61 C65 C64 -179.6(3) . . . . ? S62 C61 C65 C64 0.1(3) . . . . ? C63 C64 C65 C61 0.5(4) . . . . ? C64 C63 C66 O67 171.5(3) . . . . ? S62 C63 C66 O67 -4.2(4) . . . . ? C64 C63 C66 C68 -6.0(5) . . . . ? S62 C63 C66 C68 178.3(2) . . . . ? O67 C66 C68 C69 -36.6(4) . . . . ? C63 C66 C68 C69 140.9(3) . . . . ? O67 C66 C68 C73 142.6(3) . . . . ? C63 C66 C68 C73 -39.9(4) . . . . ? C73 C68 C69 C70 0.0(5) . . . . ? C66 C68 C69 C70 179.2(3) . . . . ? C68 C69 C70 C71 -0.1(5) . . . . ? C69 C70 C71 C72 -0.1(5) . . . . ? C70 C71 C72 C73 0.5(5) . . . . ? C71 C72 C73 C68 -0.7(5) . . . . ? C69 C68 C73 C72 0.5(4) . . . . ? C66 C68 C73 C72 -178.7(3) . . . . ?