# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Malcolm Chisholm' _publ_contact_author_email CHISHOLM@CHEMISTRY.OHIO-STATE.EDU _publ_section_title ; Chemistry of BDI*M(2+) Complexes (M = Mg, Zn) and Their Role in Lactide Polymerization where BDI* is the Anion Derived from Methylenebis(C-tBu, N-2,6-diisopropylphenyl)imine BDI*H. ; _publ_requested_category FO loop_ _publ_author_name 'Malcolm Chisholm' 'Carla N. Ayala' 'Judith Gallucci' 'Clemens Krempner' # Attachment 'archive_735238.cif' data_Chisholm1486a _database_code_depnum_ccdc_archive 'CCDC 735238' _audit_creation_date 2009-07-13T11:46:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1486' _chemical_formula_moiety 'C35 H54 N2' _chemical_formula_sum 'C35 H54 N2' _chemical_formula_weight 502.8 _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 16.6935(1) _cell_length_b 12.0280(1) _cell_length_c 17.8619(2) _cell_angle_alpha 90 _cell_angle_beta 117.121(1) _cell_angle_gamma 90 _cell_volume 3192.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5932 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'irregular chunk' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 4.3, which means that 90% of the reflections were measured at least 4.3 times. Phi and omega scans with a frame width of one degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.06 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.247336E-1 _diffrn_orient_matrix_ub_12 0.617492E-1 _diffrn_orient_matrix_ub_13 -0.102511E-1 _diffrn_orient_matrix_ub_21 -0.143285E-1 _diffrn_orient_matrix_ub_22 -0.189653E-1 _diffrn_orient_matrix_ub_23 -0.796691E-1 _diffrn_orient_matrix_ub_31 -0.617036E-1 _diffrn_orient_matrix_ub_32 0.80625E-2 _diffrn_orient_matrix_ub_33 0.91781E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 52317 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 5637 _reflns_number_gt 4255 _reflns_threshold_expression >2\s(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 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;One of the isopropyl groups had very elongated ellipsoids for its two carbon atoms, C(31) and C(32). This disorder was modeled with two carbon atoms for each of these carbons: C(31A), C(32A), C(31B) and C(32B). SADI restraints were used in the refinement of this model. The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-C, bond was refined for all of the ordered methyl groups. (The torsion angle was not refined for the disordered methyl carbon atoms.) The hydrogen atoms bonded to N(1) and to C(2) were refined isotropically. The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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^ > 2\s(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 'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.7295P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5637 _refine_ls_number_parameters 373 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.511 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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 0.0061 0.0033 '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 C1 C 0.26792(9) 0.42570(12) 0.28498(8) 0.0231(3) Uani 1 1 d . . . C2 C 0.34444(10) 0.48956(13) 0.31184(9) 0.0270(3) Uani 1 1 d . . . H2 H 0.3929(10) 0.4690(12) 0.3643(10) 0.026(4) Uiso 1 1 d . . . C3 C 0.36346(9) 0.57982(12) 0.26947(9) 0.0232(3) Uani 1 1 d . . . C4 C 0.45855(9) 0.63197(13) 0.31974(9) 0.0271(3) Uani 1 1 d . . . C5 C 0.48476(10) 0.72111(14) 0.27375(10) 0.0366(4) Uani 1 1 d . . . H5A H 0.5444 0.7507 0.3116 0.055 Uiso 1 1 calc R . . H5B H 0.4405 0.7815 0.2561 0.055 Uiso 1 1 calc R . . H5C H 0.4862 0.6883 0.2242 0.055 Uiso 1 1 calc R . . C6 C 0.45974(11) 0.68688(14) 0.39793(10) 0.0362(4) Uani 1 1 d . . . H6A H 0.5188 0.7208 0.4318 0.054 Uiso 1 1 calc R . . H6B H 0.4481 0.6305 0.4314 0.054 Uiso 1 1 calc R . . H6C H 0.4131 0.7443 0.3804 0.054 Uiso 1 1 calc R . . C7 C 0.53094(10) 0.54061(15) 0.34671(11) 0.0399(4) Uani 1 1 d . . . H7A H 0.5908 0.5746 0.3757 0.06 Uiso 1 1 calc R . . H7B H 0.5256 0.5006 0.2968 0.06 Uiso 1 1 calc R . . H7C H 0.5225 0.4885 0.3847 0.06 Uiso 1 1 calc R . . C8 C 0.27130(10) 0.32400(12) 0.33977(9) 0.0282(4) Uani 1 1 d . . . C9 C 0.29411(12) 0.36188(14) 0.42953(9) 0.0398(4) Uani 1 1 d . . . H9A H 0.3505 0.4041 0.4531 0.06 Uiso 1 1 calc R . . H9B H 0.3008 0.2966 0.4648 0.06 Uiso 1 1 calc R . . H9C H 0.2455 0.4091 0.428 0.06 Uiso 1 1 calc R . . C10 C 0.18591(11) 0.25365(14) 0.30816(10) 0.0385(4) Uani 1 1 d . . . H10A H 0.1371 0.2982 0.3089 0.058 Uiso 1 1 calc R . . H10B H 0.1971 0.1887 0.3448 0.058 Uiso 1 1 calc R . . H10C H 0.1688 0.2289 0.2506 0.058 Uiso 1 1 calc R . . C11 C 0.34655(12) 0.24722(14) 0.34326(12) 0.0456(5) Uani 1 1 d . . . H11A H 0.4043 0.2865 0.3701 0.068 Uiso 1 1 calc R . . H11B H 0.3339 0.2257 0.286 0.068 Uiso 1 1 calc R . . H11C H 0.3494 0.1805 0.3759 0.068 Uiso 1 1 calc R . . C12 C 0.10313(9) 0.41981(11) 0.17727(8) 0.0236(3) Uani 1 1 d . . . C13 C 0.05270(10) 0.46552(12) 0.21483(9) 0.0257(3) Uani 1 1 d . . . C14 C -0.03895(10) 0.44153(13) 0.17882(10) 0.0328(4) Uani 1 1 d . . . H14 H -0.0743 0.4715 0.2032 0.039 Uiso 1 1 calc R . . C15 C -0.07936(11) 0.37487(14) 0.10815(10) 0.0375(4) Uani 1 1 d . . . H15 H -0.1419 0.3593 0.0845 0.045 Uiso 1 1 calc R . . C16 C -0.02911(11) 0.33140(13) 0.07243(10) 0.0367(4) Uani 1 1 d . . . H16 H -0.0576 0.2858 0.0239 0.044 Uiso 1 1 calc R . . C17 C 0.06296(10) 0.35234(12) 0.10549(9) 0.0294(4) Uani 1 1 d . . . C18 C 0.11592(12) 0.30228(14) 0.06430(10) 0.0390(4) Uani 1 1 d . . . H18 H 0.1803 0.3254 0.0969 0.047 Uiso 1 1 calc R . . C19 C 0.08093(12) 0.34270(16) -0.02617(10) 0.0475(5) Uani 1 1 d . . . H19A H 0.1182 0.3117 -0.0504 0.071 Uiso 1 1 calc R . . H19B H 0.0836 0.4241 -0.0268 0.071 Uiso 1 1 calc R . . H19C H 0.0185 0.3183 -0.0594 0.071 Uiso 1 1 calc R . . C20 C 0.11130(17) 0.17348(16) 0.06384(13) 0.0648(6) Uani 1 1 d . . . H20A H 0.1485 0.1432 0.0392 0.097 Uiso 1 1 calc R . . H20B H 0.0488 0.1495 0.0304 0.097 Uiso 1 1 calc R . . H20C H 0.1337 0.1463 0.1216 0.097 Uiso 1 1 calc R . . C21 C 0.09619(10) 0.54257(13) 0.29008(9) 0.0286(4) Uani 1 1 d . . . H21 H 0.1599 0.5175 0.3236 0.034 Uiso 1 1 calc R . . C22 C 0.09904(13) 0.66061(14) 0.26038(11) 0.0449(5) Uani 1 1 d . . . H22A H 0.1345 0.7078 0.3091 0.067 Uiso 1 1 calc R . . H22B H 0.0376 0.6899 0.2306 0.067 Uiso 1 1 calc R . . H22C H 0.1267 0.66 0.2224 0.067 Uiso 1 1 calc R . . C23 C 0.05251(12) 0.54061(17) 0.34873(11) 0.0453(5) Uani 1 1 d . . . H23A H 0.0885 0.5853 0.3988 0.068 Uiso 1 1 calc R . . H23B H 0.0494 0.4638 0.3655 0.068 Uiso 1 1 calc R . . H23C H -0.0084 0.5715 0.3195 0.068 Uiso 1 1 calc R . . C24 C 0.30654(9) 0.68699(11) 0.13763(8) 0.0212(3) Uani 1 1 d . . . C25 C 0.27287(9) 0.79577(12) 0.13083(9) 0.0242(3) Uani 1 1 d . . . C26 C 0.27000(10) 0.86323(13) 0.06633(9) 0.0313(4) Uani 1 1 d . . . H26 H 0.2474 0.9368 0.0611 0.038 Uiso 1 1 calc R . . C27 C 0.29903(10) 0.82617(13) 0.00984(10) 0.0337(4) Uani 1 1 d . . . H27 H 0.2962 0.8735 -0.0339 0.04 Uiso 1 1 calc R . . C28 C 0.33236(10) 0.71921(13) 0.01751(9) 0.0301(4) Uani 1 1 d . . . H28 H 0.3528 0.6938 -0.0212 0.036 Uiso 1 1 calc R . . C29 C 0.33659(9) 0.64813(12) 0.08039(9) 0.0240(3) Uani 1 1 d . A . C30 C 0.37204(10) 0.53018(12) 0.08630(10) 0.0302(4) Uani 1 1 d D . . H30A H 0.3993 0.5099 0.1472 0.036 Uiso 0.540(18) 1 calc PR A 1 H30B H 0.3775 0.4941 0.1389 0.036 Uiso 0.460(18) 1 calc PR A 2 C31A C 0.4461(6) 0.5148(9) 0.0605(8) 0.0474(19) Uani 0.540(18) 1 d PD A 1 H31A H 0.4641 0.4364 0.0667 0.071 Uiso 0.540(18) 1 calc PR A 1 H31B H 0.4981 0.5606 0.0965 0.071 Uiso 0.540(18) 1 calc PR A 1 H31C H 0.4241 0.5374 0.0017 0.071 Uiso 0.540(18) 1 calc PR A 1 C32A C 0.2967(4) 0.4471(6) 0.0412(6) 0.0481(16) Uani 0.540(18) 1 d PD A 1 H32A H 0.3222 0.3725 0.0465 0.072 Uiso 0.540(18) 1 calc PR A 1 H32B H 0.2638 0.4671 -0.0184 0.072 Uiso 0.540(18) 1 calc PR A 1 H32C H 0.2554 0.4482 0.0664 0.072 Uiso 0.540(18) 1 calc PR A 1 C31B C 0.4632(5) 0.5314(12) 0.0870(9) 0.055(3) Uani 0.460(18) 1 d PD A 2 H31D H 0.485 0.4549 0.0905 0.083 Uiso 0.460(18) 1 calc PR A 2 H31E H 0.5059 0.5738 0.1357 0.083 Uiso 0.460(18) 1 calc PR A 2 H31F H 0.4577 0.5661 0.0352 0.083 Uiso 0.460(18) 1 calc PR A 2 C32B C 0.3049(6) 0.4652(8) 0.0095(8) 0.068(3) Uani 0.460(18) 1 d PD A 2 H32D H 0.3265 0.3889 0.012 0.102 Uiso 0.460(18) 1 calc PR A 2 H32E H 0.299 0.5012 -0.042 0.102 Uiso 0.460(18) 1 calc PR A 2 H32F H 0.2461 0.4639 0.0094 0.102 Uiso 0.460(18) 1 calc PR A 2 C33 C 0.24020(10) 0.84037(12) 0.19166(9) 0.0291(4) Uani 1 1 d . . . H33 H 0.2491 0.7808 0.2338 0.035 Uiso 1 1 calc R . . C34 C 0.29292(12) 0.94333(15) 0.23958(12) 0.0469(5) Uani 1 1 d . . . H34A H 0.2706 0.9677 0.279 0.07 Uiso 1 1 calc R . . H34B H 0.2848 1.0032 0.1996 0.07 Uiso 1 1 calc R . . H34C H 0.357 0.9248 0.2707 0.07 Uiso 1 1 calc R . . C35 C 0.13982(10) 0.86731(14) 0.14572(11) 0.0378(4) Uani 1 1 d . . . H35A H 0.1192 0.8909 0.1866 0.057 Uiso 1 1 calc R . . H35B H 0.1064 0.801 0.1159 0.057 Uiso 1 1 calc R . . H35C H 0.1295 0.9273 0.1052 0.057 Uiso 1 1 calc R . . N1 N 0.19670(8) 0.44818(10) 0.20949(7) 0.0234(3) Uani 1 1 d . . . H1N1 H 0.2098(11) 0.5074(16) 0.1822(11) 0.048(5) Uiso 1 1 d . . . N2 N 0.30088(7) 0.61064(9) 0.19582(7) 0.0219(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0259(8) 0.0219(8) 0.0214(7) 0.0012(6) 0.0108(6) 0.0036(6) C2 0.0229(8) 0.0296(8) 0.0223(8) 0.0045(7) 0.0049(7) 0.0005(7) C3 0.0223(7) 0.0240(8) 0.0241(8) -0.0021(6) 0.0112(6) 0.0018(6) C4 0.0219(8) 0.0316(8) 0.0257(8) -0.0019(7) 0.0092(6) -0.0013(6) C5 0.0241(8) 0.0453(10) 0.0363(9) -0.0013(8) 0.0102(7) -0.0109(7) C6 0.0324(9) 0.0410(10) 0.0330(9) -0.0098(8) 0.0130(7) -0.0088(7) C7 0.0243(8) 0.0457(11) 0.0442(10) -0.0014(8) 0.0108(7) 0.0036(7) C8 0.0299(8) 0.0239(8) 0.0269(8) 0.0049(6) 0.0094(6) 0.0014(6) C9 0.0510(11) 0.0355(10) 0.0268(8) 0.0090(7) 0.0126(8) -0.0010(8) C10 0.0402(10) 0.0321(9) 0.0363(9) 0.0131(7) 0.0114(8) -0.0046(8) C11 0.0476(11) 0.0281(9) 0.0621(12) 0.0120(9) 0.0259(9) 0.0083(8) C12 0.0239(8) 0.0202(8) 0.0223(7) 0.0057(6) 0.0066(6) -0.0014(6) C13 0.0263(8) 0.0239(8) 0.0246(8) 0.0072(6) 0.0098(6) -0.0015(6) C14 0.0266(8) 0.0335(9) 0.0368(9) 0.0105(7) 0.0131(7) -0.0012(7) C15 0.0259(8) 0.0360(10) 0.0377(9) 0.0111(8) 0.0034(7) -0.0088(7) C16 0.0372(10) 0.0281(9) 0.0281(8) 0.0017(7) 0.0003(7) -0.0078(7) C17 0.0352(9) 0.0219(8) 0.0226(8) 0.0034(6) 0.0057(7) -0.0002(7) C18 0.0459(10) 0.0357(10) 0.0274(8) -0.0046(8) 0.0099(8) 0.0027(8) C19 0.0515(11) 0.0531(12) 0.0363(10) 0.0051(9) 0.0185(9) -0.0098(9) C20 0.1036(18) 0.0414(12) 0.0581(13) 0.0025(10) 0.0445(13) 0.0136(12) C21 0.0272(8) 0.0305(9) 0.0288(8) -0.0003(7) 0.0134(7) 0.0004(7) C22 0.0627(12) 0.0323(10) 0.0449(10) -0.0055(8) 0.0290(9) -0.0056(8) C23 0.0452(10) 0.0589(12) 0.0389(10) -0.0041(9) 0.0254(8) -0.0050(9) C24 0.0177(7) 0.0220(8) 0.0220(7) -0.0004(6) 0.0074(6) -0.0041(6) C25 0.0207(7) 0.0218(8) 0.0279(8) -0.0015(6) 0.0092(6) -0.0024(6) C26 0.0302(8) 0.0220(8) 0.0394(9) 0.0050(7) 0.0140(7) 0.0015(7) C27 0.0365(9) 0.0326(9) 0.0322(9) 0.0088(7) 0.0158(7) -0.0023(7) C28 0.0328(9) 0.0327(9) 0.0296(8) -0.0016(7) 0.0184(7) -0.0050(7) C29 0.0221(7) 0.0234(8) 0.0262(8) -0.0014(6) 0.0108(6) -0.0039(6) C30 0.0371(9) 0.0250(8) 0.0344(8) -0.0025(7) 0.0214(7) 0.0012(7) C31A 0.049(3) 0.030(3) 0.081(5) -0.006(4) 0.046(4) -0.003(3) C32A 0.053(3) 0.028(3) 0.069(4) -0.011(2) 0.033(2) -0.0109(18) C31B 0.038(3) 0.042(5) 0.084(7) -0.014(4) 0.025(4) 0.011(3) C32B 0.044(3) 0.029(4) 0.110(6) -0.022(4) 0.018(4) 0.001(2) C33 0.0309(8) 0.0238(8) 0.0338(8) -0.0029(7) 0.0158(7) 0.0025(7) C34 0.0441(10) 0.0423(11) 0.0546(11) -0.0207(9) 0.0228(9) -0.0061(8) C35 0.0329(9) 0.0374(10) 0.0454(10) -0.0009(8) 0.0199(8) 0.0036(7) N1 0.0237(7) 0.0233(7) 0.0212(6) 0.0023(5) 0.0084(5) -0.0017(5) N2 0.0222(6) 0.0207(6) 0.0234(6) 0.0006(5) 0.0108(5) 0.0004(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.3577(18) . ? C1 C2 1.376(2) . ? C1 C8 1.551(2) . ? C2 C3 1.439(2) . ? C2 H2 0.950(15) . ? C3 N2 1.3063(17) . ? C3 C4 1.556(2) . ? C4 C5 1.531(2) . ? C4 C6 1.537(2) . ? C4 C7 1.539(2) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C10 1.527(2) . ? C8 C11 1.537(2) . ? C8 C9 1.538(2) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 C17 1.403(2) . ? C12 C13 1.406(2) . ? C12 N1 1.4379(18) . ? C13 C14 1.393(2) . ? C13 C21 1.518(2) . ? C14 C15 1.384(2) . ? C14 H14 0.95 . ? C15 C16 1.368(2) . ? C15 H15 0.95 . ? C16 C17 1.395(2) . ? C16 H16 0.95 . ? C17 C18 1.510(2) . ? C18 C19 1.526(2) . ? C18 C20 1.551(3) . ? C18 H18 1 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C22 1.524(2) . ? C21 C23 1.525(2) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C25 1.407(2) . ? C24 C29 1.4082(19) . ? C24 N2 1.4219(17) . ? C25 C26 1.392(2) . ? C25 C33 1.519(2) . ? C26 C27 1.378(2) . ? C26 H26 0.95 . ? C27 C28 1.383(2) . ? C27 H27 0.95 . ? C28 C29 1.388(2) . ? C28 H28 0.95 . ? C29 C30 1.522(2) . ? C30 C31A 1.514(5) . ? C30 C31B 1.517(5) . ? C30 C32A 1.518(5) . ? C30 C32B 1.532(5) . ? C30 H30A 1 . ? C30 H30B 1 . ? C31A H31A 0.98 . ? C31A H31B 0.98 . ? C31A H31C 0.98 . ? C32A H32A 0.98 . ? C32A H32B 0.98 . ? C32A H32C 0.98 . ? C31B H31D 0.98 . ? C31B H31E 0.98 . ? C31B H31F 0.98 . ? C32B H32D 0.98 . ? C32B H32E 0.98 . ? C32B H32F 0.98 . ? C33 C35 1.527(2) . ? C33 C34 1.534(2) . ? C33 H33 1 . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? N1 H1N1 0.944(19) . ? 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 N1 C1 C2 119.25(13) . . ? N1 C1 C8 123.16(13) . . ? C2 C1 C8 117.34(12) . . ? C1 C2 C3 129.06(14) . . ? C1 C2 H2 115.9(9) . . ? C3 C2 H2 115.0(9) . . ? N2 C3 C2 118.48(13) . . ? N2 C3 C4 127.16(13) . . ? C2 C3 C4 114.35(12) . . ? C5 C4 C6 107.35(13) . . ? C5 C4 C7 106.99(13) . . ? C6 C4 C7 109.84(12) . . ? C5 C4 C3 116.02(12) . . ? C6 C4 C3 106.55(12) . . ? C7 C4 C3 109.99(12) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C8 C11 106.84(13) . . ? C10 C8 C9 107.17(13) . . ? C11 C8 C9 109.04(13) . . ? C10 C8 C1 116.37(12) . . ? C11 C8 C1 107.05(12) . . ? C9 C8 C1 110.15(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 121.44(13) . . ? C17 C12 N1 118.85(13) . . ? C13 C12 N1 119.59(12) . . ? C14 C13 C12 117.99(14) . . ? C14 C13 C21 121.11(14) . . ? C12 C13 C21 120.85(13) . . ? C15 C14 C13 121.15(15) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 119.95(15) . . ? C16 C15 H15 120 . . ? C14 C15 H15 120 . . ? C15 C16 C17 121.66(15) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C12 117.81(15) . . ? C16 C17 C18 119.91(14) . . ? C12 C17 C18 122.27(14) . . ? C17 C18 C19 111.26(14) . . ? C17 C18 C20 111.24(15) . . ? C19 C18 C20 108.58(14) . . ? C17 C18 H18 108.6 . . ? C19 C18 H18 108.6 . . ? C20 C18 H18 108.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 C22 109.81(12) . . ? C13 C21 C23 114.42(13) . . ? C22 C21 C23 110.74(14) . . ? C13 C21 H21 107.2 . . ? C22 C21 H21 107.2 . . ? C23 C21 H21 107.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 120.41(13) . . ? C25 C24 N2 120.45(12) . . ? C29 C24 N2 118.73(12) . . ? C26 C25 C24 118.38(13) . . ? C26 C25 C33 119.88(13) . . ? C24 C25 C33 121.74(13) . . ? C27 C26 C25 121.78(14) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C26 C27 C28 119.23(14) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C27 C28 C29 121.53(14) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C24 118.67(13) . . ? C28 C29 C30 120.33(13) . . ? C24 C29 C30 121.00(13) . . ? C31A C30 C32A 110.6(4) . . ? C31A C30 C29 116.0(4) . . ? C31B C30 C29 110.4(6) . . ? C32A C30 C29 112.0(3) . . ? C31B C30 C32B 109.5(4) . . ? C29 C30 C32B 108.1(3) . . ? C31A C30 H30A 105.8 . . ? C32A C30 H30A 105.8 . . ? C29 C30 H30A 105.8 . . ? C31B C30 H30B 109.6 . . ? C29 C30 H30B 109.6 . . ? C32B C30 H30B 109.6 . . ? C30 C31A H31A 109.5 . . ? C30 C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C30 C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C30 C32A H32A 109.5 . . ? C30 C32A H32B 109.5 . . ? H32A C32A H32B 109.5 . . ? C30 C32A H32C 109.5 . . ? H32A C32A H32C 109.5 . . ? H32B C32A H32C 109.5 . . ? C30 C31B H31D 109.5 . . ? C30 C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C30 C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C30 C32B H32D 109.5 . . ? C30 C32B H32E 109.5 . . ? H32D C32B H32E 109.5 . . ? C30 C32B H32F 109.5 . . ? H32D C32B H32F 109.5 . . ? H32E C32B H32F 109.5 . . ? C25 C33 C35 110.76(12) . . ? C25 C33 C34 112.49(13) . . ? C35 C33 C34 109.78(13) . . ? C25 C33 H33 107.9 . . ? C35 C33 H33 107.9 . . ? C34 C33 H33 107.9 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C1 N1 C12 130.54(12) . . ? C1 N1 H1N1 111.1(11) . . ? C12 N1 H1N1 116.0(10) . . ? C3 N2 C24 129.08(12) . . ? 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 N1 C1 C2 C3 -2.0(2) . . . . ? C8 C1 C2 C3 172.46(14) . . . . ? C1 C2 C3 N2 1.8(2) . . . . ? C1 C2 C3 C4 -179.50(14) . . . . ? N2 C3 C4 C5 -6.8(2) . . . . ? C2 C3 C4 C5 174.67(13) . . . . ? N2 C3 C4 C6 112.66(16) . . . . ? C2 C3 C4 C6 -65.91(16) . . . . ? N2 C3 C4 C7 -128.33(15) . . . . ? C2 C3 C4 C7 53.10(17) . . . . ? N1 C1 C8 C10 -5.1(2) . . . . ? C2 C1 C8 C10 -179.34(14) . . . . ? N1 C1 C8 C11 114.26(15) . . . . ? C2 C1 C8 C11 -59.97(17) . . . . ? N1 C1 C8 C9 -127.31(15) . . . . ? C2 C1 C8 C9 58.46(18) . . . . ? C17 C12 C13 C14 0.2(2) . . . . ? N1 C12 C13 C14 176.20(12) . . . . ? C17 C12 C13 C21 -177.21(13) . . . . ? N1 C12 C13 C21 -1.3(2) . . . . ? C12 C13 C14 C15 -0.1(2) . . . . ? C21 C13 C14 C15 177.37(14) . . . . ? C13 C14 C15 C16 -0.1(2) . . . . ? C14 C15 C16 C17 0.1(2) . . . . ? C15 C16 C17 C12 0.1(2) . . . . ? C15 C16 C17 C18 179.73(14) . . . . ? C13 C12 C17 C16 -0.3(2) . . . . ? N1 C12 C17 C16 -176.24(13) . . . . ? C13 C12 C17 C18 -179.88(13) . . . . ? N1 C12 C17 C18 4.1(2) . . . . ? C16 C17 C18 C19 61.3(2) . . . . ? C12 C17 C18 C19 -119.05(16) . . . . ? C16 C17 C18 C20 -59.9(2) . . . . ? C12 C17 C18 C20 119.76(17) . . . . ? C14 C13 C21 C22 -94.21(17) . . . . ? C12 C13 C21 C22 83.17(17) . . . . ? C14 C13 C21 C23 31.0(2) . . . . ? C12 C13 C21 C23 -151.60(14) . . . . ? C29 C24 C25 C26 0.1(2) . . . . ? N2 C24 C25 C26 -172.41(12) . . . . ? C29 C24 C25 C33 -179.81(12) . . . . ? N2 C24 C25 C33 7.66(19) . . . . ? C24 C25 C26 C27 0.0(2) . . . . ? C33 C25 C26 C27 179.93(14) . . . . ? C25 C26 C27 C28 -0.3(2) . . . . ? C26 C27 C28 C29 0.5(2) . . . . ? C27 C28 C29 C24 -0.4(2) . . . . ? C27 C28 C29 C30 178.90(14) . . . . ? C25 C24 C29 C28 0.1(2) . . . . ? N2 C24 C29 C28 172.73(12) . . . . ? C25 C24 C29 C30 -179.21(13) . . . . ? N2 C24 C29 C30 -6.55(19) . . . . ? C28 C29 C30 C31A 33.8(5) . . . . ? C24 C29 C30 C31A -146.9(5) . . . . ? C28 C29 C30 C31B 52.3(6) . . . . ? C24 C29 C30 C31B -128.5(6) . . . . ? C28 C29 C30 C32A -94.5(4) . . . . ? C24 C29 C30 C32A 84.8(4) . . . . ? C28 C29 C30 C32B -67.5(8) . . . . ? C24 C29 C30 C32B 111.7(8) . . . . ? C26 C25 C33 C35 63.62(18) . . . . ? C24 C25 C33 C35 -116.46(15) . . . . ? C26 C25 C33 C34 -59.65(18) . . . . ? C24 C25 C33 C34 120.28(15) . . . . ? C2 C1 N1 C12 -159.44(14) . . . . ? C8 C1 N1 C12 26.4(2) . . . . ? C17 C12 N1 C1 -118.36(16) . . . . ? C13 C12 N1 C1 65.6(2) . . . . ? C2 C3 N2 C24 -171.59(13) . . . . ? C4 C3 N2 C24 9.9(2) . . . . ? C25 C24 N2 C3 -101.72(17) . . . . ? C29 C24 N2 C3 85.63(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N1 N2 0.944(19) 1.891(19) 2.7001(17) 142.3(15) . # END of CIF # Attachment 'archive_735239.cif' data_Chisholm1494a _database_code_depnum_ccdc_archive 'CCDC 735239' _audit_creation_date 2009-07-17T16:11:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1494a' _chemical_formula_moiety 'C35 H54 N2, 0.105(H2 O1)' _chemical_formula_sum 'C35 H54.2 N2 O0.105' _chemical_formula_weight 504.69 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 15.5478(2) _cell_length_b 9.7599(1) _cell_length_c 22.1039(3) _cell_angle_alpha 90 _cell_angle_beta 106.180(1) _cell_angle_gamma 90 _cell_volume 3221.30(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6026 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'trapezoid-shaped chunk' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.041 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116.2 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.5, which means that 90% of the reflections were measured at least 3.5 times. Phi and omega scans with a frame width of one degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.059 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.644694E-1 _diffrn_orient_matrix_ub_12 0.60434E-2 _diffrn_orient_matrix_ub_13 0.17095E-1 _diffrn_orient_matrix_ub_21 0.22828E-1 _diffrn_orient_matrix_ub_22 0.278318E-1 _diffrn_orient_matrix_ub_23 -0.959288E-1 _diffrn_orient_matrix_ub_31 0.56775E-2 _diffrn_orient_matrix_ub_32 0.445326E-1 _diffrn_orient_matrix_ub_33 0.142713E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 41657 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5671 _reflns_number_gt 4170 _reflns_threshold_expression >2\s(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 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;One of the isopropyl groups is disordered over two orientations. These two orientations are modeled with atoms C(31A) and C(32A) for one and atoms C(31B) and C(32B) for the other, with atom C(30) common to both orientations. SADI restraints were used in modeling this disorder. A difference electron density map indicated that both nitrogen atoms are bonded to hydrogen atoms. Since both hydrogen atoms cannot be simultaneously present, they were included in the model with occupancy factors of 0.4 and 0.6, and they were refined isotropically. The bond lengths in the N-C-C-C-N fragment support this disordered hydrogen model. There is also a region of electron density consisting of a single peak located within the cavity of this molecule. This was modeled as a partially occupied oxygen atom, which would presumably be part of a water molecule. This water molecule would be present only when the C(31B), C(32B) orientation of the disordered isopropyl group is also present, as it is too close to the other orientation of this group. The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). For some of these groups, the torsion angle, which defines the orientation of the methyl group about the C-C, bond was refined. The hydrogen atoms bonded to N(1) and N(2) were refined isotropically. The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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^ > 2\s(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 'w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+1.0299P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5671 _refine_ls_number_parameters 383 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.325 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 C1 C 0.36724(10) 0.38538(16) 0.20015(7) 0.0285(4) Uani 1 1 d . . . C2 C 0.40336(11) 0.44542(17) 0.25916(7) 0.0331(4) Uani 1 1 d . . . H2 H 0.4594 0.4898 0.2647 0.04 Uiso 1 1 calc R . . C3 C 0.36858(10) 0.44967(16) 0.31176(7) 0.0276(4) Uani 1 1 d . . . C4 C 0.42538(11) 0.53466(17) 0.36848(7) 0.0316(4) Uani 1 1 d . . . C5 C 0.39413(13) 0.5352(2) 0.42850(8) 0.0445(5) Uani 1 1 d . . . H9A H 0.332 0.5674 0.4184 0.067 Uiso 1 1 calc R . . H9B H 0.4326 0.5964 0.4597 0.067 Uiso 1 1 calc R . . H9C H 0.3978 0.4421 0.4457 0.067 Uiso 1 1 calc R . . C6 C 0.52234(12) 0.4827(2) 0.38743(9) 0.0471(5) Uani 1 1 d . . . H11A H 0.5479 0.4931 0.3518 0.071 Uiso 1 1 calc R . . H11B H 0.5233 0.3858 0.3992 0.071 Uiso 1 1 calc R . . H11C H 0.5578 0.5359 0.4234 0.071 Uiso 1 1 calc R . . C7 C 0.42276(13) 0.68391(18) 0.34639(8) 0.0420(5) Uani 1 1 d . . . H10A H 0.3605 0.7154 0.3326 0.063 Uiso 1 1 calc R . . H10B H 0.4494 0.6903 0.3112 0.063 Uiso 1 1 calc R . . H10C H 0.4567 0.7414 0.3812 0.063 Uiso 1 1 calc R . . C8 C 0.42599(10) 0.39398(17) 0.15397(7) 0.0316(4) Uani 1 1 d . . . C9 C 0.38301(12) 0.3437(2) 0.08673(8) 0.0445(5) Uani 1 1 d . . . H7A H 0.3644 0.248 0.0878 0.067 Uiso 1 1 calc R . . H7B H 0.4265 0.3507 0.0622 0.067 Uiso 1 1 calc R . . H7C H 0.3306 0.4003 0.0671 0.067 Uiso 1 1 calc R . . C10 C 0.50956(12) 0.3057(2) 0.18158(9) 0.0475(5) Uani 1 1 d . . . H6A H 0.4915 0.2104 0.1849 0.071 Uiso 1 1 calc R . . H6B H 0.5415 0.34 0.2235 0.071 Uiso 1 1 calc R . . H6C H 0.549 0.3103 0.1539 0.071 Uiso 1 1 calc R . . C11 C 0.45499(13) 0.54261(19) 0.14822(9) 0.0450(5) Uani 1 1 d . . . H5A H 0.4885 0.5766 0.1898 0.067 Uiso 1 1 calc R . . H5B H 0.4019 0.5998 0.1315 0.067 Uiso 1 1 calc R . . H5C H 0.4932 0.5464 0.1197 0.067 Uiso 1 1 calc R . . C12 C 0.23047(10) 0.26894(17) 0.13176(7) 0.0290(4) Uani 1 1 d . . . C13 C 0.17401(11) 0.36091(18) 0.09012(7) 0.0328(4) Uani 1 1 d . . . C14 C 0.11249(12) 0.3081(2) 0.03708(8) 0.0397(4) Uani 1 1 d . . . H14 H 0.0742 0.369 0.0082 0.048 Uiso 1 1 calc R . . C15 C 0.10576(12) 0.1691(2) 0.02540(8) 0.0427(5) Uani 1 1 d . . . H15 H 0.0631 0.135 -0.0111 0.051 Uiso 1 1 calc R . . C16 C 0.16090(11) 0.08019(19) 0.06672(8) 0.0395(4) Uani 1 1 d . . . H16 H 0.1558 -0.0154 0.0584 0.047 Uiso 1 1 calc R . . C17 C 0.22406(10) 0.12681(17) 0.12051(8) 0.0328(4) Uani 1 1 d . . . C18 C 0.28376(12) 0.02422(18) 0.16447(9) 0.0429(5) Uani 1 1 d . . . H18 H 0.3248 0.076 0.2 0.051 Uiso 1 1 calc R . . C19 C 0.22809(16) -0.0739(2) 0.19198(12) 0.0695(7) Uani 1 1 d . . . H19A H 0.2679 -0.1377 0.2209 0.104 Uiso 1 1 calc R . . H19B H 0.1872 -0.1255 0.1578 0.104 Uiso 1 1 calc R . . H19C H 0.1934 -0.0216 0.2148 0.104 Uiso 1 1 calc R . . C20 C 0.34128(15) -0.0570(2) 0.13075(11) 0.0655(6) Uani 1 1 d . . . H20A H 0.3784 -0.1231 0.1601 0.098 Uiso 1 1 calc R . . H20B H 0.3799 0.0061 0.1158 0.098 Uiso 1 1 calc R . . H20C H 0.3022 -0.106 0.0948 0.098 Uiso 1 1 calc R . . C21 C 0.17602(12) 0.51419(18) 0.10295(8) 0.0382(4) Uani 1 1 d . . . H21 H 0.2341 0.536 0.1347 0.046 Uiso 1 1 calc R . . C22 C 0.10044(16) 0.5511(2) 0.13158(11) 0.0626(6) Uani 1 1 d . . . H22A H 0.1033 0.649 0.1417 0.094 Uiso 1 1 calc R . . H22B H 0.1068 0.4977 0.1701 0.094 Uiso 1 1 calc R . . H22C H 0.0427 0.5301 0.1013 0.094 Uiso 1 1 calc R . . C23 C 0.16931(14) 0.6024(2) 0.04501(10) 0.0536(5) Uani 1 1 d . . . H23A H 0.1748 0.6992 0.0572 0.08 Uiso 1 1 calc R . . H23B H 0.1113 0.5869 0.0141 0.08 Uiso 1 1 calc R . . H23C H 0.2175 0.5778 0.0264 0.08 Uiso 1 1 calc R . . C24 C 0.24915(10) 0.36762(16) 0.35675(7) 0.0282(4) Uani 1 1 d . . . C25 C 0.17667(11) 0.44995(19) 0.35925(8) 0.0378(4) Uani 1 1 d . . . C26 C 0.13594(13) 0.4247(2) 0.40691(9) 0.0479(5) Uani 1 1 d . . . H26 H 0.0873 0.4807 0.4099 0.057 Uiso 1 1 calc R . . C27 C 0.16456(13) 0.3206(2) 0.44980(9) 0.0477(5) Uani 1 1 d . . . H27 H 0.1365 0.3062 0.4824 0.057 Uiso 1 1 calc R . . C28 C 0.23406(13) 0.23743(19) 0.44525(9) 0.0445(5) Uani 1 1 d . . . H28 H 0.2529 0.1645 0.4744 0.053 Uiso 1 1 calc R . . C29 C 0.27702(12) 0.25824(17) 0.39883(8) 0.0353(4) Uani 1 1 d . A . C30 C 0.35111(14) 0.1630(2) 0.39244(10) 0.0555(6) Uani 1 1 d D . . H30A H 0.3931 0.222 0.377 0.067 Uiso 0.46(2) 1 calc PR A 1 H30B H 0.3846 0.2032 0.3641 0.067 Uiso 0.54(2) 1 calc PR A 2 C31A C 0.3154(7) 0.0572(9) 0.3403(3) 0.065(3) Uani 0.46(2) 1 d PD A 1 H31A H 0.2775 0.103 0.3029 0.098 Uiso 0.46(2) 1 calc PR A 1 H31B H 0.2801 -0.0119 0.3551 0.098 Uiso 0.46(2) 1 calc PR A 1 H31C H 0.3658 0.0126 0.3297 0.098 Uiso 0.46(2) 1 calc PR A 1 C32A C 0.4091(10) 0.0913(16) 0.4507(4) 0.084(4) Uani 0.46(2) 1 d PD A 1 H32A H 0.4527 0.0324 0.4387 0.125 Uiso 0.46(2) 1 calc PR A 1 H32B H 0.3711 0.0353 0.4696 0.125 Uiso 0.46(2) 1 calc PR A 1 H32C H 0.4407 0.1599 0.4812 0.125 Uiso 0.46(2) 1 calc PR A 1 C31B C 0.3041(8) 0.0288(12) 0.3650(12) 0.154(6) Uani 0.54(2) 1 d PD A 2 H31D H 0.3489 -0.0381 0.3605 0.231 Uiso 0.54(2) 1 calc PR A 2 H31E H 0.2621 0.0469 0.3236 0.231 Uiso 0.54(2) 1 calc PR A 2 H31F H 0.2713 -0.008 0.3933 0.231 Uiso 0.54(2) 1 calc PR A 2 C32B C 0.4137(6) 0.1334(19) 0.4577(4) 0.075(3) Uani 0.54(2) 1 d PD A 2 H32D H 0.4616 0.0718 0.4538 0.113 Uiso 0.54(2) 1 calc PR A 2 H32E H 0.3798 0.0899 0.4838 0.113 Uiso 0.54(2) 1 calc PR A 2 H32F H 0.4398 0.2194 0.4774 0.113 Uiso 0.54(2) 1 calc PR A 2 C33 C 0.14411(14) 0.5695(2) 0.31341(9) 0.0601(6) Uani 1 1 d . . . H33 H 0.1777 0.5666 0.2808 0.072 Uiso 1 1 calc R . . C34 C 0.16089(16) 0.7086(2) 0.34612(14) 0.0749(7) Uani 1 1 d . . . H34A H 0.2252 0.7202 0.366 0.112 Uiso 1 1 calc R . . H34B H 0.1287 0.7135 0.3784 0.112 Uiso 1 1 calc R . . H34C H 0.1396 0.7814 0.315 0.112 Uiso 1 1 calc R . . C35 C 0.04445(16) 0.5513(3) 0.28005(11) 0.0749(8) Uani 1 1 d . . . H35A H 0.0348 0.4625 0.2585 0.112 Uiso 1 1 calc R . . H35B H 0.0244 0.6249 0.2491 0.112 Uiso 1 1 calc R . . H35C H 0.0102 0.555 0.3111 0.112 Uiso 1 1 calc R . . N1 N 0.28950(9) 0.31886(14) 0.18913(7) 0.0291(3) Uani 1 1 d . . . H36 H 0.2713(16) 0.315(2) 0.2207(13) 0.016(6) Uiso 0.6 1 d P . . N2 N 0.29129(9) 0.38946(13) 0.30785(6) 0.0269(3) Uani 1 1 d . . . H37 H 0.264(3) 0.356(4) 0.269(2) 0.023(10) Uiso 0.4 1 d P . . O1 O 0.2399(7) 0.1729(10) 0.2601(4) 0.032(4) Uani 0.105(4) 1 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 C1 0.0253(8) 0.0319(9) 0.0288(8) 0.0041(7) 0.0085(7) 0.0039(7) C2 0.0274(9) 0.0434(10) 0.0290(9) -0.0011(8) 0.0086(7) -0.0084(8) C3 0.0295(9) 0.0247(8) 0.0273(8) 0.0037(7) 0.0056(7) 0.0005(7) C4 0.0338(9) 0.0336(9) 0.0257(8) -0.0004(7) 0.0058(7) -0.0057(7) C5 0.0500(11) 0.0540(12) 0.0286(9) -0.0088(8) 0.0091(8) -0.0177(9) C6 0.0372(10) 0.0552(12) 0.0421(11) -0.0026(9) -0.0001(8) -0.0014(9) C7 0.0495(11) 0.0351(10) 0.0398(10) -0.0044(8) 0.0096(8) -0.0092(9) C8 0.0300(9) 0.0376(9) 0.0300(9) 0.0006(7) 0.0132(7) -0.0004(7) C9 0.0410(10) 0.0628(13) 0.0367(10) -0.0084(9) 0.0223(8) -0.0074(9) C10 0.0423(11) 0.0566(12) 0.0507(11) 0.0113(10) 0.0247(9) 0.0125(9) C11 0.0575(12) 0.0449(11) 0.0385(10) 0.0041(9) 0.0231(9) -0.0070(9) C12 0.0258(8) 0.0379(10) 0.0255(8) -0.0036(7) 0.0110(7) -0.0043(7) C13 0.0314(9) 0.0414(10) 0.0274(8) -0.0002(8) 0.0110(7) -0.0024(8) C14 0.0350(10) 0.0531(12) 0.0305(9) 0.0000(9) 0.0083(8) 0.0012(9) C15 0.0350(10) 0.0608(13) 0.0300(9) -0.0141(9) 0.0055(8) -0.0084(9) C16 0.0371(10) 0.0428(11) 0.0409(10) -0.0141(9) 0.0148(8) -0.0069(9) C17 0.0290(9) 0.0384(10) 0.0331(9) -0.0064(8) 0.0120(7) -0.0035(8) C18 0.0413(10) 0.0356(10) 0.0494(11) -0.0050(9) 0.0087(9) -0.0012(8) C19 0.0651(15) 0.0583(14) 0.0799(17) 0.0218(13) 0.0114(13) -0.0041(12) C20 0.0544(13) 0.0551(14) 0.0822(17) -0.0116(12) 0.0109(12) 0.0152(11) C21 0.0384(10) 0.0392(10) 0.0349(10) 0.0041(8) 0.0068(8) -0.0004(8) C22 0.0873(17) 0.0455(12) 0.0706(15) -0.0061(11) 0.0479(13) -0.0018(12) C23 0.0626(13) 0.0488(12) 0.0531(12) 0.0128(10) 0.0221(10) 0.0008(10) C24 0.0293(8) 0.0301(9) 0.0273(8) -0.0066(7) 0.0110(7) -0.0043(7) C25 0.0372(10) 0.0456(11) 0.0340(9) -0.0047(8) 0.0153(8) 0.0062(8) C26 0.0431(11) 0.0615(13) 0.0470(11) -0.0073(10) 0.0259(9) 0.0055(10) C27 0.0546(12) 0.0543(12) 0.0463(11) -0.0052(10) 0.0338(10) -0.0099(10) C28 0.0572(12) 0.0386(10) 0.0436(11) 0.0044(9) 0.0238(9) -0.0073(9) C29 0.0401(10) 0.0307(9) 0.0384(10) 0.0007(8) 0.0161(8) -0.0028(8) C30 0.0648(14) 0.0448(12) 0.0676(14) 0.0215(11) 0.0359(11) 0.0211(11) C31A 0.089(5) 0.042(3) 0.081(5) -0.001(3) 0.052(4) 0.013(3) C32A 0.107(8) 0.084(9) 0.075(5) 0.045(4) 0.050(5) 0.048(6) C31B 0.168(9) 0.077(6) 0.206(14) -0.062(8) 0.035(9) 0.055(6) C32B 0.044(4) 0.078(7) 0.113(6) 0.056(4) 0.038(4) 0.031(3) C33 0.0515(13) 0.0887(17) 0.0465(12) 0.0111(11) 0.0244(10) 0.0359(12) C34 0.0546(14) 0.0503(14) 0.121(2) 0.0188(14) 0.0264(14) 0.0123(11) C35 0.0750(16) 0.0886(18) 0.0517(13) -0.0175(13) 0.0023(12) 0.0385(14) N1 0.0306(8) 0.0349(8) 0.0232(7) -0.0016(6) 0.0099(6) -0.0039(6) N2 0.0275(7) 0.0296(7) 0.0252(7) -0.0029(6) 0.0101(6) 0.0004(6) O1 0.061(8) 0.027(6) 0.016(6) -0.006(4) 0.022(5) -0.027(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.333(2) . ? C1 C2 1.397(2) . ? C1 C8 1.550(2) . ? C2 C3 1.413(2) . ? C2 H2 0.95 . ? C3 N2 1.319(2) . ? C3 C4 1.557(2) . ? C4 C7 1.533(2) . ? C4 C6 1.534(2) . ? C4 C5 1.535(2) . ? C5 H9A 0.98 . ? C5 H9B 0.98 . ? C5 H9C 0.98 . ? C6 H11A 0.98 . ? C6 H11B 0.98 . ? C6 H11C 0.98 . ? C7 H10A 0.98 . ? C7 H10B 0.98 . ? C7 H10C 0.98 . ? C8 C9 1.530(2) . ? C8 C11 1.535(2) . ? C8 C10 1.537(2) . ? C9 H7A 0.98 . ? C9 H7B 0.98 . ? C9 H7C 0.98 . ? C10 H6A 0.98 . ? C10 H6B 0.98 . ? C10 H6C 0.98 . ? C11 H5A 0.98 . ? C11 H5B 0.98 . ? C11 H5C 0.98 . ? C12 C13 1.405(2) . ? C12 C17 1.408(2) . ? C12 N1 1.428(2) . ? C13 C14 1.389(2) . ? C13 C21 1.521(2) . ? C14 C15 1.380(3) . ? C14 H14 0.95 . ? C15 C16 1.373(3) . ? C15 H15 0.95 . ? C16 C17 1.391(2) . ? C16 H16 0.95 . ? C17 C18 1.518(2) . ? C18 C19 1.526(3) . ? C18 C20 1.535(3) . ? C18 H18 1 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C23 1.522(2) . ? C21 C22 1.525(3) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C25 1.398(2) . ? C24 C29 1.403(2) . ? C24 N2 1.4274(19) . ? C25 C26 1.394(2) . ? C25 C33 1.536(3) . ? C26 C27 1.376(3) . ? C26 H26 0.95 . ? C27 C28 1.378(3) . ? C27 H27 0.95 . ? C28 C29 1.386(2) . ? C28 H28 0.95 . ? C29 C30 1.517(3) . ? C30 C32A 1.521(6) . ? C30 C32B 1.526(6) . ? C30 C31A 1.532(6) . ? C30 C31B 1.541(7) . ? C30 H30A 1 . ? C30 H30B 1 . ? C31A H31A 0.98 . ? C31A H31B 0.98 . ? C31A H31C 0.98 . ? C32A H32A 0.98 . ? C32A H32B 0.98 . ? C32A H32C 0.98 . ? C31B H31D 0.98 . ? C31B H31E 0.98 . ? C31B H31F 0.98 . ? C32B H32D 0.98 . ? C32B H32E 0.98 . ? C32B H32F 0.98 . ? C33 C34 1.526(3) . ? C33 C35 1.530(3) . ? C33 H33 1 . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? N1 H36 0.82(3) . ? N2 H37 0.91(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 N1 C1 C2 118.87(14) . . ? N1 C1 C8 125.21(14) . . ? C2 C1 C8 115.77(13) . . ? C1 C2 C3 129.36(15) . . ? C1 C2 H2 115.3 . . ? C3 C2 H2 115.3 . . ? N2 C3 C2 118.92(14) . . ? N2 C3 C4 126.34(14) . . ? C2 C3 C4 114.65(13) . . ? C7 C4 C6 109.76(15) . . ? C7 C4 C5 106.57(14) . . ? C6 C4 C5 106.79(14) . . ? C7 C4 C3 106.92(13) . . ? C6 C4 C3 109.73(14) . . ? C5 C4 C3 116.92(13) . . ? C4 C5 H9A 109.5 . . ? C4 C5 H9B 109.5 . . ? H9A C5 H9B 109.5 . . ? C4 C5 H9C 109.5 . . ? H9A C5 H9C 109.5 . . ? H9B C5 H9C 109.5 . . ? C4 C6 H11A 109.5 . . ? C4 C6 H11B 109.5 . . ? H11A C6 H11B 109.5 . . ? C4 C6 H11C 109.5 . . ? H11A C6 H11C 109.5 . . ? H11B C6 H11C 109.5 . . ? C4 C7 H10A 109.5 . . ? C4 C7 H10B 109.5 . . ? H10A C7 H10B 109.5 . . ? C4 C7 H10C 109.5 . . ? H10A C7 H10C 109.5 . . ? H10B C7 H10C 109.5 . . ? C9 C8 C11 106.35(14) . . ? C9 C8 C10 107.33(15) . . ? C11 C8 C10 109.11(15) . . ? C9 C8 C1 116.36(13) . . ? C11 C8 C1 110.26(13) . . ? C10 C8 C1 107.23(13) . . ? C8 C9 H7A 109.5 . . ? C8 C9 H7B 109.5 . . ? H7A C9 H7B 109.5 . . ? C8 C9 H7C 109.5 . . ? H7A C9 H7C 109.5 . . ? H7B C9 H7C 109.5 . . ? C8 C10 H6A 109.5 . . ? C8 C10 H6B 109.5 . . ? H6A C10 H6B 109.5 . . ? C8 C10 H6C 109.5 . . ? H6A C10 H6C 109.5 . . ? H6B C10 H6C 109.5 . . ? C8 C11 H5A 109.5 . . ? C8 C11 H5B 109.5 . . ? H5A C11 H5B 109.5 . . ? C8 C11 H5C 109.5 . . ? H5A C11 H5C 109.5 . . ? H5B C11 H5C 109.5 . . ? C13 C12 C17 120.89(15) . . ? C13 C12 N1 119.57(15) . . ? C17 C12 N1 119.29(15) . . ? C14 C13 C12 118.26(16) . . ? C14 C13 C21 119.71(16) . . ? C12 C13 C21 121.98(15) . . ? C15 C14 C13 121.41(17) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 119.75(16) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.54(17) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C12 118.14(16) . . ? C16 C17 C18 119.43(16) . . ? C12 C17 C18 122.43(15) . . ? C17 C18 C19 110.81(15) . . ? C17 C18 C20 111.41(16) . . ? C19 C18 C20 109.93(18) . . ? C17 C18 H18 108.2 . . ? C19 C18 H18 108.2 . . ? C20 C18 H18 108.2 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 C23 113.97(15) . . ? C13 C21 C22 109.34(15) . . ? C23 C21 C22 109.61(16) . . ? C13 C21 H21 107.9 . . ? C23 C21 H21 107.9 . . ? C22 C21 H21 107.9 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 120.98(14) . . ? C25 C24 N2 119.30(14) . . ? C29 C24 N2 119.57(14) . . ? C26 C25 C24 118.00(16) . . ? C26 C25 C33 119.82(16) . . ? C24 C25 C33 122.12(15) . . ? C27 C26 C25 121.55(17) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C28 119.63(16) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C29 121.15(17) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C24 118.59(16) . . ? C28 C29 C30 120.94(16) . . ? C24 C29 C30 120.45(15) . . ? C29 C30 C32A 119.3(6) . . ? C29 C30 C32B 109.2(6) . . ? C29 C30 C31A 111.0(4) . . ? C32A C30 C31A 109.3(5) . . ? C29 C30 C31B 105.6(5) . . ? C32B C30 C31B 108.6(5) . . ? C29 C30 H30A 105.4 . . ? C32A C30 H30A 105.4 . . ? C31A C30 H30A 105.4 . . ? C29 C30 H30B 111.1 . . ? C32B C30 H30B 111.1 . . ? C31B C30 H30B 111.1 . . ? C30 C31A H31A 109.5 . . ? C30 C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C30 C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C30 C32A H32A 109.5 . . ? C30 C32A H32B 109.5 . . ? H32A C32A H32B 109.5 . . ? C30 C32A H32C 109.5 . . ? H32A C32A H32C 109.5 . . ? H32B C32A H32C 109.5 . . ? C30 C31B H31D 109.5 . . ? C30 C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C30 C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C30 C32B H32D 109.5 . . ? C30 C32B H32E 109.5 . . ? H32D C32B H32E 109.5 . . ? C30 C32B H32F 109.5 . . ? H32D C32B H32F 109.5 . . ? H32E C32B H32F 109.5 . . ? C34 C33 C35 110.35(17) . . ? C34 C33 C25 112.45(17) . . ? C35 C33 C25 109.5(2) . . ? C34 C33 H33 108.1 . . ? C35 C33 H33 108.1 . . ? C25 C33 H33 108.1 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C1 N1 C12 130.84(14) . . ? C1 N1 H36 112.0(17) . . ? C12 N1 H36 116.7(17) . . ? C3 N2 C24 128.24(14) . . ? C3 N2 H37 114(2) . . ? C24 N2 H37 118(2) . . ? 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 N1 C1 C2 C3 -1.3(3) . . . . ? C8 C1 C2 C3 -177.12(16) . . . . ? C1 C2 C3 N2 0.5(3) . . . . ? C1 C2 C3 C4 -176.27(16) . . . . ? N2 C3 C4 C7 -111.87(17) . . . . ? C2 C3 C4 C7 64.58(18) . . . . ? N2 C3 C4 C6 129.15(17) . . . . ? C2 C3 C4 C6 -54.40(18) . . . . ? N2 C3 C4 C5 7.4(2) . . . . ? C2 C3 C4 C5 -176.15(15) . . . . ? N1 C1 C8 C9 11.3(2) . . . . ? C2 C1 C8 C9 -173.15(15) . . . . ? N1 C1 C8 C11 132.49(17) . . . . ? C2 C1 C8 C11 -51.96(19) . . . . ? N1 C1 C8 C10 -108.83(18) . . . . ? C2 C1 C8 C10 66.73(19) . . . . ? C17 C12 C13 C14 -0.9(2) . . . . ? N1 C12 C13 C14 -175.14(14) . . . . ? C17 C12 C13 C21 176.61(14) . . . . ? N1 C12 C13 C21 2.3(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C21 C13 C14 C15 -176.91(16) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C15 C16 C17 C18 -179.64(16) . . . . ? C13 C12 C17 C16 0.6(2) . . . . ? N1 C12 C17 C16 174.91(14) . . . . ? C13 C12 C17 C18 -179.89(15) . . . . ? N1 C12 C17 C18 -5.6(2) . . . . ? C16 C17 C18 C19 -61.9(2) . . . . ? C12 C17 C18 C19 118.60(19) . . . . ? C16 C17 C18 C20 60.8(2) . . . . ? C12 C17 C18 C20 -118.66(18) . . . . ? C14 C13 C21 C23 -44.0(2) . . . . ? C12 C13 C21 C23 138.58(17) . . . . ? C14 C13 C21 C22 79.1(2) . . . . ? C12 C13 C21 C22 -98.38(19) . . . . ? C29 C24 C25 C26 3.4(3) . . . . ? N2 C24 C25 C26 178.96(16) . . . . ? C29 C24 C25 C33 -179.40(17) . . . . ? N2 C24 C25 C33 -3.8(3) . . . . ? C24 C25 C26 C27 -1.2(3) . . . . ? C33 C25 C26 C27 -178.47(19) . . . . ? C25 C26 C27 C28 -1.1(3) . . . . ? C26 C27 C28 C29 1.2(3) . . . . ? C27 C28 C29 C24 0.9(3) . . . . ? C27 C28 C29 C30 -177.62(18) . . . . ? C25 C24 C29 C28 -3.2(2) . . . . ? N2 C24 C29 C28 -178.84(15) . . . . ? C25 C24 C29 C30 175.29(17) . . . . ? N2 C24 C29 C30 -0.3(2) . . . . ? C28 C29 C30 C32A -29.4(8) . . . . ? C24 C29 C30 C32A 152.1(8) . . . . ? C28 C29 C30 C32B -43.8(7) . . . . ? C24 C29 C30 C32B 137.7(7) . . . . ? C28 C29 C30 C31A 99.0(4) . . . . ? C24 C29 C30 C31A -79.5(4) . . . . ? C28 C29 C30 C31B 72.8(12) . . . . ? C24 C29 C30 C31B -105.7(11) . . . . ? C26 C25 C33 C34 65.1(2) . . . . ? C24 C25 C33 C34 -112.1(2) . . . . ? C26 C25 C33 C35 -57.9(2) . . . . ? C24 C25 C33 C35 124.89(19) . . . . ? C2 C1 N1 C12 168.03(16) . . . . ? C8 C1 N1 C12 -16.5(3) . . . . ? C13 C12 N1 C1 -77.3(2) . . . . ? C17 C12 N1 C1 108.37(19) . . . . ? C2 C3 N2 C24 172.15(15) . . . . ? C4 C3 N2 C24 -11.5(3) . . . . ? C25 C24 N2 C3 104.23(19) . . . . ? C29 C24 N2 C3 -80.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H36 N2 0.82(3) 2.00(3) 2.7058(18) 143(2) . N2 H37 N1 0.91(4) 1.95(4) 2.7058(18) 140(3) . #===END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-10-20 at 13:33:11 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1503 _database_code_depnum_ccdc_archive 'CCDC 735240' _audit_creation_date 2008-10-20T13:33:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1503' _chemical_formula_moiety 'C35 H54 N2' _chemical_formula_sum 'C35 H54 N2' _chemical_formula_weight 502.8 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.9388(1) _cell_length_b 13.0230(1) _cell_length_c 50.4676(5) _cell_angle_alpha 90 _cell_angle_beta 90.194(1) _cell_angle_gamma 90 _cell_volume 9818.31(14) _cell_formula_units_Z 12 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 8649 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'approximately cubic' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.02 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3336 _exptl_special_details ;All work was done at 230 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 2.7, which means that 90% of the reflections were measured at least 2.7 times. Phi and omega scans with a frame width of 0.5 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. There are 1.5 molecules in the asymmetric unit, with the half molecule located on a two-fold rotation axis. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.058 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.195462E-1 _diffrn_orient_matrix_ub_12 -0.697327E-1 _diffrn_orient_matrix_ub_13 0.59653E-2 _diffrn_orient_matrix_ub_21 0.423468E-1 _diffrn_orient_matrix_ub_22 -0.3987E-2 _diffrn_orient_matrix_ub_23 -0.15269E-1 _diffrn_orient_matrix_ub_31 0.480175E-1 _diffrn_orient_matrix_ub_32 0.319018E-1 _diffrn_orient_matrix_ub_33 0.11131E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 39200 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_limit_l_max 60 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 8612 _reflns_number_gt 4963 _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 'SHELXS-97 (Sheldrick, 1986)' _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 ;The two t-butyl groups on the molecule in the general position are disordered and were modeled with two orientations each. For the t-butyl group involving atom C(4), the two orientations are composed of the set of atoms C(5), C(6), C(7) and C(5A), C(6A), C(7A). These two orientations are related to each other by rotation about the C(3)-C(4) bond. For the other disordered t-butyl group, the whole group is disordered such that C(8), C(9), C(10), C(11) represent one orientation and C(8A), C(9A), C(10A), C(11A) represent a second orientation. Various restraints (SADI, SIMU, DELU) were used in refining these disordered groups along with EADP constraints. A difference electron density map indicated that both nitrogen atoms, N(1) and N(2), in the molecule on a general position are bonded to hydrogen atoms. Since both hydrogen atoms cannot be simultaneously present, they were included in the model with occupancy factors of 0.7 and 0.3, and were refined isotropically. Their refined Uiso values were comparable in value. For the molecule on the two-fold rotation axis, the hydrogen atom bonded to N(3) was assigned an occupancy factor of 0.5, since it is disordered because of the two-fold rotation axis. The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The hydrogen atoms bonded to C(2) and C(37) were refined isotropically. The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.0229P] 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_number_reflns 8612 _refine_ls_number_parameters 560 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.195 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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 0.0061 0.0033 '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 C1 C 0.47075(13) 0.38118(14) 0.42259(4) 0.0490(5) Uani 1 1 d D . . C2 C 0.48774(14) 0.33731(16) 0.44702(4) 0.0508(5) Uani 1 1 d . B . H2 H 0.5015(10) 0.3834(12) 0.4603(3) 0.036(5) Uiso 1 1 d . . . C3 C 0.48688(12) 0.23072(15) 0.45407(4) 0.0436(5) Uani 1 1 d . . . C4 C 0.53864(13) 0.19971(15) 0.47951(4) 0.0510(5) Uani 1 1 d DU A . C5 C 0.5932(5) 0.2878(4) 0.49170(14) 0.127(4) Uani 0.616(7) 1 d PDU A 1 H5A H 0.5535 0.3442 0.4961 0.191 Uiso 0.616(7) 1 calc PR A 1 H5B H 0.6376 0.311 0.4791 0.191 Uiso 0.616(7) 1 calc PR A 1 H5C H 0.6229 0.2639 0.5077 0.191 Uiso 0.616(7) 1 calc PR A 1 C6 C 0.4778(3) 0.1613(5) 0.50181(8) 0.086(2) Uani 0.616(7) 1 d PDU A 1 H6A H 0.4404 0.106 0.4952 0.128 Uiso 0.616(7) 1 calc PR A 1 H6B H 0.4403 0.2173 0.5079 0.128 Uiso 0.616(7) 1 calc PR A 1 H6C H 0.5143 0.1365 0.5164 0.128 Uiso 0.616(7) 1 calc PR A 1 C7 C 0.6038(3) 0.1148(4) 0.47302(8) 0.087(2) Uani 0.616(7) 1 d PDU A 1 H7A H 0.5716 0.057 0.4655 0.13 Uiso 0.616(7) 1 calc PR A 1 H7B H 0.6344 0.0932 0.4891 0.13 Uiso 0.616(7) 1 calc PR A 1 H7C H 0.6474 0.1396 0.4603 0.13 Uiso 0.616(7) 1 calc PR A 1 C5A C 0.5136(8) 0.2706(8) 0.50173(13) 0.117(5) Uani 0.384(7) 1 d PDU A 2 H5A1 H 0.5207 0.3413 0.496 0.175 Uiso 0.384(7) 1 calc PR A 2 H5A2 H 0.5522 0.2578 0.5169 0.175 Uiso 0.384(7) 1 calc PR A 2 H5A3 H 0.4518 0.2587 0.5067 0.175 Uiso 0.384(7) 1 calc PR A 2 C6A C 0.5306(7) 0.0876(5) 0.48627(18) 0.107(5) Uani 0.384(7) 1 d PDU A 2 H6A1 H 0.5468 0.0466 0.471 0.161 Uiso 0.384(7) 1 calc PR A 2 H6A2 H 0.4694 0.0724 0.4913 0.161 Uiso 0.384(7) 1 calc PR A 2 H6A3 H 0.5704 0.0715 0.5009 0.161 Uiso 0.384(7) 1 calc PR A 2 C7A C 0.6366(3) 0.2191(8) 0.47229(18) 0.095(3) Uani 0.384(7) 1 d PDU A 2 H7A1 H 0.6541 0.1729 0.4581 0.142 Uiso 0.384(7) 1 calc PR A 2 H7A2 H 0.6742 0.207 0.4877 0.142 Uiso 0.384(7) 1 calc PR A 2 H7A3 H 0.6437 0.2896 0.4665 0.142 Uiso 0.384(7) 1 calc PR A 2 C8 C 0.4712(3) 0.4994(3) 0.41857(13) 0.0540(11) Uani 0.620(3) 1 d PD B 1 C9 C 0.3856(4) 0.5282(9) 0.4030(2) 0.100(3) Uani 0.620(3) 1 d PD B 1 H9A H 0.3833 0.6021 0.4007 0.15 Uiso 0.620(3) 1 calc PR B 1 H9B H 0.3334 0.5057 0.4128 0.15 Uiso 0.620(3) 1 calc PR B 1 H9C H 0.3865 0.495 0.3858 0.15 Uiso 0.620(3) 1 calc PR B 1 C10 C 0.5529(3) 0.5412(3) 0.40357(8) 0.0805(11) Uani 0.620(3) 1 d PD B 1 H10A H 0.5486 0.6154 0.4023 0.121 Uiso 0.620(3) 1 calc PR B 1 H10B H 0.5545 0.5118 0.3859 0.121 Uiso 0.620(3) 1 calc PR B 1 H10C H 0.6072 0.523 0.4131 0.121 Uiso 0.620(3) 1 calc PR B 1 C11 C 0.4736(3) 0.5510(3) 0.44615(8) 0.0778(10) Uani 0.620(3) 1 d PD B 1 H11A H 0.4732 0.625 0.444 0.117 Uiso 0.620(3) 1 calc PR B 1 H11B H 0.5275 0.5303 0.4555 0.117 Uiso 0.620(3) 1 calc PR B 1 H11C H 0.4215 0.53 0.4562 0.117 Uiso 0.620(3) 1 calc PR B 1 C8A C 0.4472(5) 0.4974(5) 0.4236(3) 0.0540(11) Uani 0.380(3) 1 d PD B 2 C9A C 0.4270(9) 0.5403(15) 0.3966(4) 0.100(3) Uani 0.380(3) 1 d PD B 2 H9A1 H 0.3768 0.5036 0.3889 0.15 Uiso 0.380(3) 1 calc PR B 2 H9A2 H 0.479 0.5325 0.3853 0.15 Uiso 0.380(3) 1 calc PR B 2 H9A3 H 0.4121 0.6126 0.3981 0.15 Uiso 0.380(3) 1 calc PR B 2 C10A C 0.5276(5) 0.5558(5) 0.43381(17) 0.0805(11) Uani 0.380(3) 1 d PD B 2 H10D H 0.5148 0.6288 0.4336 0.121 Uiso 0.380(3) 1 calc PR B 2 H10E H 0.5787 0.542 0.4226 0.121 Uiso 0.380(3) 1 calc PR B 2 H10F H 0.541 0.5342 0.4518 0.121 Uiso 0.380(3) 1 calc PR B 2 C11A C 0.3663(5) 0.5236(4) 0.44021(13) 0.0778(10) Uani 0.380(3) 1 d PD B 2 H11D H 0.314 0.4889 0.4331 0.117 Uiso 0.380(3) 1 calc PR B 2 H11E H 0.3565 0.5972 0.4399 0.117 Uiso 0.380(3) 1 calc PR B 2 H11F H 0.3764 0.5015 0.4583 0.117 Uiso 0.380(3) 1 calc PR B 2 C12 C 0.46916(13) 0.33369(13) 0.37395(4) 0.0431(5) Uani 1 1 d . . . C13 C 0.55661(13) 0.34138(14) 0.36383(4) 0.0522(5) Uani 1 1 d . B . C14 C 0.56657(15) 0.34774(16) 0.33652(5) 0.0611(6) Uani 1 1 d . . . H14 H 0.6244 0.3527 0.3294 0.073 Uiso 1 1 calc R B . C15 C 0.49416(15) 0.34691(15) 0.31974(4) 0.0564(6) Uani 1 1 d . B . H15 H 0.5027 0.3528 0.3014 0.068 Uiso 1 1 calc R . . C16 C 0.40888(14) 0.33743(14) 0.32979(4) 0.0490(5) Uani 1 1 d . . . H16 H 0.3597 0.3364 0.3181 0.059 Uiso 1 1 calc R B . C17 C 0.39463(12) 0.32946(13) 0.35687(4) 0.0410(5) Uani 1 1 d . B . C18 C 0.30125(12) 0.31259(14) 0.36763(4) 0.0478(5) Uani 1 1 d . . . H18 H 0.2997 0.3418 0.3857 0.057 Uiso 1 1 calc R B . C19 C 0.28104(14) 0.19759(16) 0.36999(5) 0.0709(7) Uani 1 1 d . B . H19A H 0.2214 0.1882 0.3771 0.106 Uiso 1 1 calc R . . H19B H 0.3245 0.1658 0.3817 0.106 Uiso 1 1 calc R . . H19C H 0.2844 0.166 0.3526 0.106 Uiso 1 1 calc R . . C20 C 0.22848(14) 0.3658(2) 0.35152(5) 0.0801(8) Uani 1 1 d . B . H20A H 0.1707 0.3533 0.3596 0.12 Uiso 1 1 calc R . . H20B H 0.2283 0.3389 0.3336 0.12 Uiso 1 1 calc R . . H20C H 0.24 0.4391 0.3511 0.12 Uiso 1 1 calc R . . C21 C 0.63988(14) 0.3362(2) 0.38152(5) 0.0757(7) Uani 1 1 d . . . H21 H 0.6222 0.3545 0.3998 0.091 Uiso 1 1 calc R B . C22 C 0.67788(19) 0.2285(3) 0.38180(7) 0.1234(12) Uani 1 1 d . B . H22A H 0.7296 0.226 0.3935 0.185 Uiso 1 1 calc R . . H22B H 0.6957 0.2093 0.364 0.185 Uiso 1 1 calc R . . H22C H 0.6327 0.1809 0.3881 0.185 Uiso 1 1 calc R . . C23 C 0.7133(2) 0.4109(3) 0.37258(7) 0.1569(17) Uani 1 1 d . B . H23A H 0.7636 0.4069 0.3847 0.235 Uiso 1 1 calc R . . H23B H 0.6897 0.4803 0.3724 0.235 Uiso 1 1 calc R . . H23C H 0.7329 0.3925 0.3549 0.235 Uiso 1 1 calc R . . C24 C 0.41510(12) 0.06536(14) 0.44107(4) 0.0406(5) Uani 1 1 d . . . C25 C 0.33401(12) 0.04982(14) 0.45471(4) 0.0433(5) Uani 1 1 d . B . C26 C 0.29742(14) -0.04789(17) 0.45471(4) 0.0564(6) Uani 1 1 d . . . H26 H 0.2436 -0.0595 0.4638 0.068 Uiso 1 1 calc R B . C27 C 0.33756(17) -0.12802(17) 0.44178(5) 0.0679(7) Uani 1 1 d . B . H27 H 0.3115 -0.1937 0.4421 0.081 Uiso 1 1 calc R . . C28 C 0.41578(17) -0.11200(16) 0.42834(4) 0.0625(6) Uani 1 1 d . . . H28 H 0.4429 -0.1673 0.4195 0.075 Uiso 1 1 calc R B . C29 C 0.45607(13) -0.01549(15) 0.42748(4) 0.0483(5) Uani 1 1 d . B . C30 C 0.53930(14) 0.00078(18) 0.41127(4) 0.0623(6) Uani 1 1 d . . . H30 H 0.5637 0.0691 0.416 0.075 Uiso 1 1 calc R B . C31 C 0.51552(17) 0.0029(2) 0.38165(5) 0.0860(8) Uani 1 1 d . B . H31A H 0.5693 0.0146 0.3714 0.129 Uiso 1 1 calc R . . H31B H 0.4731 0.0577 0.3783 0.129 Uiso 1 1 calc R . . H31C H 0.4891 -0.0623 0.3766 0.129 Uiso 1 1 calc R . . C32 C 0.61231(17) -0.0784(2) 0.41693(5) 0.1002(9) Uani 1 1 d . B . H32A H 0.6643 -0.0637 0.4061 0.15 Uiso 1 1 calc R . . H32B H 0.5901 -0.1465 0.4128 0.15 Uiso 1 1 calc R . . H32C H 0.6289 -0.0753 0.4355 0.15 Uiso 1 1 calc R . . C33 C 0.28568(13) 0.13826(15) 0.46776(4) 0.0526(5) Uani 1 1 d . . . H33 H 0.3322 0.1839 0.4753 0.063 Uiso 1 1 calc R B . C34 C 0.22543(15) 0.10544(19) 0.49071(5) 0.0806(7) Uani 1 1 d . B . H34A H 0.1971 0.1656 0.4983 0.121 Uiso 1 1 calc R . . H34B H 0.2612 0.0713 0.5041 0.121 Uiso 1 1 calc R . . H34C H 0.1798 0.0587 0.4842 0.121 Uiso 1 1 calc R . . C35 C 0.23368(15) 0.20153(18) 0.44747(5) 0.0784(7) Uani 1 1 d . B . H35A H 0.204 0.2581 0.4563 0.118 Uiso 1 1 calc R . . H35B H 0.1893 0.1584 0.4389 0.118 Uiso 1 1 calc R . . H35C H 0.2746 0.2283 0.4343 0.118 Uiso 1 1 calc R . . C36 C 0.04675(10) 0.44615(13) 0.22920(3) 0.0336(4) Uani 1 1 d . . . C37 C 0 0.4932(2) 0.25 0.0384(7) Uani 1 2 d S . . H37 H 0 0.5637(17) 0.25 0.030(6) Uiso 1 2 d S . . C38 C 0.07621(12) 0.51494(13) 0.20578(4) 0.0407(5) Uani 1 1 d . . . C39 C -0.01110(13) 0.55109(15) 0.19233(4) 0.0575(6) Uani 1 1 d . . . H39A H 0.0032 0.5951 0.1774 0.086 Uiso 1 1 calc R . . H39B H -0.0469 0.589 0.205 0.086 Uiso 1 1 calc R . . H39C H -0.0445 0.4919 0.1861 0.086 Uiso 1 1 calc R . . C40 C 0.12797(14) 0.60919(15) 0.21564(4) 0.0629(6) Uani 1 1 d . . . H40A H 0.1455 0.651 0.2006 0.094 Uiso 1 1 calc R . . H40B H 0.181 0.587 0.2252 0.094 Uiso 1 1 calc R . . H40C H 0.0902 0.6492 0.2273 0.094 Uiso 1 1 calc R . . C41 C 0.13204(14) 0.46164(15) 0.18469(4) 0.0629(6) Uani 1 1 d . . . H41A H 0.1474 0.5105 0.1709 0.094 Uiso 1 1 calc R . . H41B H 0.0979 0.4055 0.177 0.094 Uiso 1 1 calc R . . H41C H 0.1864 0.4349 0.1927 0.094 Uiso 1 1 calc R . . C42 C 0.12055(11) 0.27934(13) 0.21787(4) 0.0366(4) Uani 1 1 d . . . C43 C 0.09122(12) 0.20249(13) 0.20052(4) 0.0432(5) Uani 1 1 d . . . C44 C 0.15395(14) 0.13241(15) 0.19138(4) 0.0566(6) Uani 1 1 d . . . H44 H 0.1356 0.08 0.1798 0.068 Uiso 1 1 calc R . . C45 C 0.24164(14) 0.13784(16) 0.19890(5) 0.0645(6) Uani 1 1 d . . . H45 H 0.2829 0.0895 0.1925 0.077 Uiso 1 1 calc R . . C46 C 0.26982(13) 0.21411(16) 0.21590(4) 0.0551(6) Uani 1 1 d . . . H46 H 0.3306 0.2175 0.2207 0.066 Uiso 1 1 calc R . . C47 C 0.21052(12) 0.28638(13) 0.22612(4) 0.0406(5) Uani 1 1 d . . . C48 C 0.24026(12) 0.36801(14) 0.24564(4) 0.0458(5) Uani 1 1 d . . . H48 H 0.209 0.4322 0.2407 0.055 Uiso 1 1 calc R . . C49 C 0.21185(14) 0.34218(16) 0.27381(4) 0.0580(6) Uani 1 1 d . . . H49A H 0.2317 0.396 0.2857 0.087 Uiso 1 1 calc R . . H49B H 0.2386 0.2774 0.2791 0.087 Uiso 1 1 calc R . . H49C H 0.1472 0.3366 0.2746 0.087 Uiso 1 1 calc R . . C50 C 0.34099(13) 0.39119(18) 0.24501(5) 0.0706(7) Uani 1 1 d . . . H50A H 0.3549 0.4441 0.2579 0.106 Uiso 1 1 calc R . . H50B H 0.3575 0.4148 0.2275 0.106 Uiso 1 1 calc R . . H50C H 0.3742 0.3293 0.2492 0.106 Uiso 1 1 calc R . . C51 C -0.00598(13) 0.19559(15) 0.19228(4) 0.0559(6) Uani 1 1 d . . . H51 H -0.0324 0.2649 0.1943 0.067 Uiso 1 1 calc R . . C52 C -0.01873(17) 0.1632(2) 0.16340(5) 0.0957(9) Uani 1 1 d . . . H52A H -0.0821 0.1616 0.1592 0.144 Uiso 1 1 calc R . . H52B H 0.0067 0.0954 0.1608 0.144 Uiso 1 1 calc R . . H52C H 0.0111 0.212 0.1519 0.144 Uiso 1 1 calc R . . C53 C -0.05753(15) 0.12299(18) 0.21059(6) 0.0847(8) Uani 1 1 d . . . H53A H -0.1197 0.1201 0.2051 0.127 Uiso 1 1 calc R . . H53B H -0.0539 0.148 0.2287 0.127 Uiso 1 1 calc R . . H53C H -0.0316 0.0548 0.2096 0.127 Uiso 1 1 calc R . . N1 N 0.45464(11) 0.31869(15) 0.40167(3) 0.0484(5) Uani 1 1 d . B . H1N1 H 0.4470(15) 0.253(2) 0.4066(5) 0.040(8) Uiso 0.7 1 d P . . N2 N 0.44704(11) 0.16714(12) 0.43791(4) 0.0446(4) Uani 1 1 d . B . H1N2 H 0.446(4) 0.182(5) 0.4220(15) 0.05(2) Uiso 0.3 1 d P . . N3 N 0.05531(10) 0.34500(11) 0.22944(3) 0.0408(4) Uani 1 1 d . . . H1N3 H 0.011(2) 0.3220(18) 0.2407(5) 0.016(8) Uiso 0.5 1 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 C1 0.0632(13) 0.0408(12) 0.0429(13) 0.0041(10) -0.0112(10) -0.0092(10) C2 0.0662(14) 0.0472(13) 0.0390(13) 0.0007(11) -0.0132(10) -0.0124(11) C3 0.0446(11) 0.0473(13) 0.0389(12) 0.0065(10) -0.0032(9) -0.0068(9) C4 0.0523(13) 0.0555(13) 0.0452(13) 0.0109(10) -0.0132(10) -0.0094(10) C5 0.163(7) 0.097(4) 0.122(6) 0.030(4) -0.099(6) -0.044(5) C6 0.068(3) 0.144(6) 0.044(3) 0.027(3) -0.004(2) 0.021(3) C7 0.067(3) 0.140(6) 0.053(3) 0.014(3) -0.013(2) 0.029(4) C5A 0.164(9) 0.150(10) 0.036(4) -0.016(5) -0.036(5) 0.063(10) C6A 0.135(10) 0.085(5) 0.102(8) 0.058(5) -0.079(8) -0.033(6) C7A 0.047(4) 0.119(9) 0.117(7) 0.045(6) -0.029(4) -0.013(4) C8 0.084(3) 0.0397(13) 0.038(3) 0.0049(13) -0.008(2) -0.0104(16) C9 0.109(7) 0.049(3) 0.142(7) -0.018(3) -0.060(6) 0.025(6) C10 0.109(3) 0.050(2) 0.082(3) 0.0107(19) -0.008(2) -0.0261(19) C11 0.118(3) 0.047(2) 0.069(3) -0.0006(17) 0.005(2) -0.004(2) C8A 0.084(3) 0.0397(13) 0.038(3) 0.0049(13) -0.008(2) -0.0104(16) C9A 0.109(7) 0.049(3) 0.142(7) -0.018(3) -0.060(6) 0.025(6) C10A 0.109(3) 0.050(2) 0.082(3) 0.0107(19) -0.008(2) -0.0261(19) C11A 0.118(3) 0.047(2) 0.069(3) -0.0006(17) 0.005(2) -0.004(2) C12 0.0575(13) 0.0344(11) 0.0374(12) 0.0061(9) -0.0038(10) -0.0036(9) C13 0.0570(13) 0.0504(13) 0.0491(14) 0.0122(10) -0.0023(10) -0.0108(10) C14 0.0603(14) 0.0629(15) 0.0600(16) 0.0086(12) 0.0087(12) -0.0142(11) C15 0.0698(15) 0.0577(14) 0.0418(13) 0.0010(11) 0.0046(12) -0.0111(11) C16 0.0614(14) 0.0456(12) 0.0398(13) -0.0037(10) -0.0043(10) -0.0010(10) C17 0.0520(12) 0.0333(11) 0.0378(12) -0.0014(9) -0.0018(9) 0.0009(9) C18 0.0508(12) 0.0521(13) 0.0405(12) -0.0063(10) -0.0018(9) 0.0033(10) C19 0.0601(14) 0.0664(16) 0.0862(19) -0.0112(13) 0.0107(12) -0.0147(12) C20 0.0630(15) 0.112(2) 0.0654(17) 0.0014(14) -0.0007(12) 0.0257(14) C21 0.0554(14) 0.100(2) 0.0715(17) 0.0321(15) -0.0113(12) -0.0223(14) C22 0.085(2) 0.159(3) 0.126(3) 0.046(2) -0.0114(18) 0.030(2) C23 0.103(2) 0.232(4) 0.135(3) 0.094(3) -0.055(2) -0.105(3) C24 0.0474(12) 0.0377(12) 0.0368(12) 0.0078(9) -0.0056(9) -0.0006(9) C25 0.0460(12) 0.0439(12) 0.0399(12) 0.0048(9) -0.0060(9) -0.0050(10) C26 0.0593(13) 0.0557(14) 0.0542(15) 0.0060(11) -0.0009(11) -0.0159(11) C27 0.0897(19) 0.0473(14) 0.0667(17) 0.0033(12) -0.0108(14) -0.0152(13) C28 0.0883(18) 0.0437(14) 0.0553(15) -0.0060(11) -0.0093(13) 0.0095(12) C29 0.0582(13) 0.0468(13) 0.0398(13) 0.0037(10) -0.0053(10) 0.0067(10) C30 0.0656(15) 0.0732(15) 0.0483(14) -0.0007(12) 0.0028(11) 0.0166(12) C31 0.0892(18) 0.118(2) 0.0509(16) 0.0084(15) 0.0051(13) 0.0257(16) C32 0.0808(18) 0.140(2) 0.080(2) 0.0034(18) 0.0004(15) 0.0516(18) C33 0.0414(11) 0.0601(13) 0.0562(14) -0.0039(11) 0.0000(10) -0.0015(10) C34 0.0637(15) 0.0965(19) 0.0817(19) -0.0014(15) 0.0200(13) 0.0033(14) C35 0.0673(16) 0.0755(17) 0.092(2) 0.0044(14) -0.0114(14) 0.0165(13) C36 0.0320(10) 0.0340(11) 0.0348(11) 0.0015(8) 0.0006(8) -0.0013(8) C37 0.0500(17) 0.0233(15) 0.0421(18) 0 0.0077(13) 0 C38 0.0476(11) 0.0378(11) 0.0366(12) 0.0070(9) 0.0062(9) 0.0031(9) C39 0.0650(14) 0.0628(14) 0.0446(13) 0.0104(11) -0.0021(10) 0.0130(11) C40 0.0756(15) 0.0520(13) 0.0612(15) 0.0188(11) 0.0017(11) -0.0173(12) C41 0.0792(15) 0.0621(14) 0.0475(14) 0.0197(11) 0.0249(11) 0.0127(12) C42 0.0429(11) 0.0312(10) 0.0358(11) 0.0036(9) 0.0094(9) 0.0058(8) C43 0.0468(12) 0.0358(11) 0.0471(13) -0.0044(9) 0.0047(9) 0.0053(9) C44 0.0582(14) 0.0475(13) 0.0642(15) -0.0171(11) 0.0029(11) 0.0093(11) C45 0.0570(15) 0.0569(14) 0.0795(18) -0.0155(13) 0.0048(12) 0.0209(11) C46 0.0409(12) 0.0588(14) 0.0656(15) -0.0015(12) 0.0030(10) 0.0119(10) C47 0.0415(11) 0.0400(11) 0.0403(12) 0.0035(9) 0.0045(9) 0.0040(9) C48 0.0452(12) 0.0435(12) 0.0488(13) 0.0033(10) 0.0002(9) 0.0019(9) C49 0.0633(14) 0.0608(14) 0.0501(14) -0.0007(11) -0.0036(11) 0.0016(11) C50 0.0526(14) 0.0740(16) 0.0853(18) -0.0051(13) -0.0008(12) -0.0116(12) C51 0.0536(13) 0.0476(12) 0.0665(16) -0.0160(11) -0.0037(11) 0.0063(10) C52 0.0834(19) 0.117(2) 0.086(2) -0.0359(17) -0.0257(15) 0.0136(16) C53 0.0649(16) 0.0633(16) 0.126(2) -0.0074(15) 0.0151(15) -0.0152(12) N1 0.0679(12) 0.0390(11) 0.0383(11) 0.0076(9) -0.0066(8) -0.0096(9) N2 0.0555(11) 0.0411(11) 0.0373(11) 0.0079(9) -0.0045(8) -0.0069(8) N3 0.0441(10) 0.0288(9) 0.0496(11) 0.0003(8) 0.0169(8) 0.0018(7) #----------------------------------------------------------------------------# # 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 C1 N1 1.354(2) . ? C1 C2 1.382(3) . ? C1 C8 1.552(5) . ? C1 C8A 1.555(7) . ? C2 C3 1.433(3) . ? C2 H2 0.923(17) . ? C3 N2 1.305(2) . ? C3 C4 1.550(3) . ? C4 C5A 1.501(6) . ? C4 C6A 1.504(5) . ? C4 C7 1.510(4) . ? C4 C7A 1.530(5) . ? C4 C6 1.532(4) . ? C4 C5 1.535(4) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C5 H5C 0.97 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C6 H6C 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C7 H7C 0.97 . ? C5A H5A1 0.97 . ? C5A H5A2 0.97 . ? C5A H5A3 0.97 . ? C6A H6A1 0.97 . ? C6A H6A2 0.97 . ? C6A H6A3 0.97 . ? C7A H7A1 0.97 . ? C7A H7A2 0.97 . ? C7A H7A3 0.97 . ? C8 C10 1.539(5) . ? C8 C9 1.544(6) . ? C8 C11 1.546(6) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C9 H9C 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C10 H10C 0.97 . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C11 H11C 0.97 . ? C8A C9A 1.504(10) . ? C8A C10A 1.511(9) . ? C8A C11A 1.512(8) . ? C9A H9A1 0.97 . ? C9A H9A2 0.97 . ? C9A H9A3 0.97 . ? C10A H10D 0.97 . ? C10A H10E 0.97 . ? C10A H10F 0.97 . ? C11A H11D 0.97 . ? C11A H11E 0.97 . ? C11A H11F 0.97 . ? C12 C17 1.407(2) . ? C12 C13 1.408(3) . ? C12 N1 1.430(2) . ? C13 C14 1.390(3) . ? C13 C21 1.530(3) . ? C14 C15 1.371(3) . ? C14 H14 0.94 . ? C15 C16 1.378(3) . ? C15 H15 0.94 . ? C16 C17 1.388(2) . ? C16 H16 0.94 . ? C17 C18 1.515(3) . ? C18 C20 1.522(3) . ? C18 C19 1.533(3) . ? C18 H18 0.99 . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C19 H19C 0.97 . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C20 H20C 0.97 . ? C21 C22 1.514(4) . ? C21 C23 1.534(3) . ? C21 H21 0.99 . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C22 H22C 0.97 . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C23 H23C 0.97 . ? C24 C29 1.399(3) . ? C24 C25 1.410(3) . ? C24 N2 1.418(2) . ? C25 C26 1.385(3) . ? C25 C33 1.511(3) . ? C26 C27 1.370(3) . ? C26 H26 0.94 . ? C27 C28 1.369(3) . ? C27 H27 0.94 . ? C28 C29 1.394(3) . ? C28 H28 0.94 . ? C29 C30 1.506(3) . ? C30 C32 1.527(3) . ? C30 C31 1.536(3) . ? C30 H30 0.99 . ? C31 H31A 0.97 . ? C31 H31B 0.97 . ? C31 H31C 0.97 . ? C32 H32A 0.97 . ? C32 H32B 0.97 . ? C32 H32C 0.97 . ? C33 C35 1.525(3) . ? C33 C34 1.530(3) . ? C33 H33 0.99 . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? C34 H34C 0.97 . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C35 H35C 0.97 . ? C36 N3 1.323(2) . ? C36 C37 1.404(2) . ? C36 C38 1.548(2) . ? C37 C36 1.404(2) 2 ? C37 H37 0.92(2) . ? C38 C41 1.522(3) . ? C38 C40 1.533(3) . ? C38 C39 1.542(2) . ? C39 H39A 0.97 . ? C39 H39B 0.97 . ? C39 H39C 0.97 . ? C40 H40A 0.97 . ? C40 H40B 0.97 . ? C40 H40C 0.97 . ? C41 H41A 0.97 . ? C41 H41B 0.97 . ? C41 H41C 0.97 . ? C42 C43 1.399(2) . ? C42 C47 1.409(2) . ? C42 N3 1.423(2) . ? C43 C44 1.388(3) . ? C43 C51 1.512(3) . ? C44 C45 1.365(3) . ? C44 H44 0.94 . ? C45 C46 1.378(3) . ? C45 H45 0.94 . ? C46 C47 1.393(2) . ? C46 H46 0.94 . ? C47 C48 1.515(3) . ? C48 C49 1.523(3) . ? C48 C50 1.535(3) . ? C48 H48 0.99 . ? C49 H49A 0.97 . ? C49 H49B 0.97 . ? C49 H49C 0.97 . ? C50 H50A 0.97 . ? C50 H50B 0.97 . ? C50 H50C 0.97 . ? C51 C52 1.529(3) . ? C51 C53 1.532(3) . ? C51 H51 0.99 . ? C52 H52A 0.97 . ? C52 H52B 0.97 . ? C52 H52C 0.97 . ? C53 H53A 0.97 . ? C53 H53B 0.97 . ? C53 H53C 0.97 . ? N1 H1N1 0.90(3) . ? N2 H1N2 0.83(8) . ? N3 H1N3 0.93(3) . ? 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 N1 C1 C2 118.63(18) . . ? N1 C1 C8 119.6(3) . . ? C2 C1 C8 121.7(3) . . ? N1 C1 C8A 124.8(5) . . ? C2 C1 C8A 114.4(5) . . ? C1 C2 C3 128.3(2) . . ? C1 C2 H2 114.8(10) . . ? C3 C2 H2 116.8(10) . . ? N2 C3 C2 117.65(17) . . ? N2 C3 C4 125.29(17) . . ? C2 C3 C4 116.94(17) . . ? C5A C4 C6A 114.0(6) . . ? C5A C4 C7A 108.5(6) . . ? C6A C4 C7A 106.9(5) . . ? C7 C4 C6 107.7(3) . . ? C7 C4 C5 107.0(4) . . ? C6 C4 C5 105.3(4) . . ? C5A C4 C3 109.5(3) . . ? C6A C4 C3 113.6(3) . . ? C7 C4 C3 109.4(2) . . ? C7A C4 C3 103.6(3) . . ? C6 C4 C3 113.44(19) . . ? C5 C4 C3 113.6(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C5A H5A1 109.5 . . ? C4 C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? C4 C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? C4 C6A H6A1 109.5 . . ? C4 C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C4 C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C4 C7A H7A1 109.5 . . ? C4 C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C4 C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C10 C8 C9 108.7(4) . . ? C10 C8 C11 105.8(4) . . ? C9 C8 C11 111.6(6) . . ? C10 C8 C1 114.8(3) . . ? C9 C8 C1 107.7(6) . . ? C11 C8 C1 108.3(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9A C8A C10A 106.2(8) . . ? C9A C8A C11A 105.1(8) . . ? C10A C8A C11A 109.5(8) . . ? C9A C8A C1 112.1(10) . . ? C10A C8A C1 108.8(6) . . ? C11A C8A C1 114.8(5) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C8A C10A H10D 109.5 . . ? C8A C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? C8A C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C8A C11A H11D 109.5 . . ? C8A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? C8A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? C17 C12 C13 120.93(18) . . ? C17 C12 N1 118.15(17) . . ? C13 C12 N1 120.58(17) . . ? C14 C13 C12 117.82(19) . . ? C14 C13 C21 119.5(2) . . ? C12 C13 C21 122.61(19) . . ? C15 C14 C13 121.7(2) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.94(19) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C12 118.48(17) . . ? C16 C17 C18 120.56(17) . . ? C12 C17 C18 120.92(17) . . ? C17 C18 C20 113.54(17) . . ? C17 C18 C19 110.58(15) . . ? C20 C18 C19 110.23(18) . . ? C17 C18 H18 107.4 . . ? C20 C18 H18 107.4 . . ? C19 C18 H18 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C13 110.5(2) . . ? C22 C21 C23 108.8(3) . . ? C13 C21 C23 112.4(2) . . ? C22 C21 H21 108.4 . . ? C13 C21 H21 108.4 . . ? C23 C21 H21 108.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 C25 120.63(17) . . ? C29 C24 N2 120.03(17) . . ? C25 C24 N2 118.63(17) . . ? C26 C25 C24 118.13(18) . . ? C26 C25 C33 120.74(18) . . ? C24 C25 C33 121.05(16) . . ? C27 C26 C25 121.8(2) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C28 C27 C26 119.7(2) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 121.5(2) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C28 C29 C24 118.26(19) . . ? C28 C29 C30 120.08(19) . . ? C24 C29 C30 121.61(18) . . ? C29 C30 C32 113.20(19) . . ? C29 C30 C31 110.04(18) . . ? C32 C30 C31 110.91(19) . . ? C29 C30 H30 107.5 . . ? C32 C30 H30 107.5 . . ? C31 C30 H30 107.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C25 C33 C35 111.25(18) . . ? C25 C33 C34 113.58(17) . . ? C35 C33 C34 111.07(18) . . ? C25 C33 H33 106.8 . . ? C35 C33 H33 106.8 . . ? C34 C33 H33 106.8 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N3 C36 C37 118.41(17) . . ? N3 C36 C38 123.73(16) . . ? C37 C36 C38 117.51(16) . . ? C36 C37 C36 128.2(2) 2 . ? C36 C37 H37 115.88(12) 2 . ? C36 C37 H37 115.88(13) . . ? C41 C38 C40 108.37(16) . . ? C41 C38 C39 107.24(16) . . ? C40 C38 C39 108.87(15) . . ? C41 C38 C36 115.33(15) . . ? C40 C38 C36 111.09(15) . . ? C39 C38 C36 105.69(14) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C41 H41A 109.5 . . ? C38 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C38 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C47 121.86(16) . . ? C43 C42 N3 118.23(16) . . ? C47 C42 N3 119.59(16) . . ? C44 C43 C42 117.90(17) . . ? C44 C43 C51 121.23(17) . . ? C42 C43 C51 120.86(16) . . ? C45 C44 C43 121.48(19) . . ? C45 C44 H44 119.3 . . ? C43 C44 H44 119.3 . . ? C44 C45 C46 120.10(19) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C47 121.64(19) . . ? C45 C46 H46 119.2 . . ? C47 C46 H46 119.2 . . ? C46 C47 C42 117.00(17) . . ? C46 C47 C48 121.98(17) . . ? C42 C47 C48 121.01(16) . . ? C47 C48 C49 111.72(15) . . ? C47 C48 C50 114.19(16) . . ? C49 C48 C50 109.82(17) . . ? C47 C48 H48 106.9 . . ? C49 C48 H48 106.9 . . ? C50 C48 H48 106.9 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C43 C51 C52 113.26(18) . . ? C43 C51 C53 110.81(18) . . ? C52 C51 C53 110.10(19) . . ? C43 C51 H51 107.5 . . ? C52 C51 H51 107.5 . . ? C53 C51 H51 107.5 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C1 N1 C12 130.83(18) . . ? C1 N1 H1N1 112.1(16) . . ? C12 N1 H1N1 115.0(16) . . ? C3 N2 C24 132.52(18) . . ? C3 N2 H1N2 118(5) . . ? C24 N2 H1N2 109(5) . . ? C36 N3 C42 131.34(16) . . ? C36 N3 H1N3 105.0(15) . . ? C42 N3 H1N3 123.4(15) . . ? 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 N1 C1 C2 C3 -3.2(3) . . . . ? C8 C1 C2 C3 177.7(3) . . . . ? C8A C1 C2 C3 161.2(4) . . . . ? C1 C2 C3 N2 -16.7(3) . . . . ? C1 C2 C3 C4 159.6(2) . . . . ? N2 C3 C4 C5A -135.7(6) . . . . ? C2 C3 C4 C5A 48.3(6) . . . . ? N2 C3 C4 C6A -6.9(6) . . . . ? C2 C3 C4 C6A 177.1(5) . . . . ? N2 C3 C4 C7 49.6(3) . . . . ? C2 C3 C4 C7 -126.4(3) . . . . ? N2 C3 C4 C7A 108.7(5) . . . . ? C2 C3 C4 C7A -67.3(5) . . . . ? N2 C3 C4 C6 -70.7(4) . . . . ? C2 C3 C4 C6 113.3(3) . . . . ? N2 C3 C4 C5 169.1(4) . . . . ? C2 C3 C4 C5 -6.9(5) . . . . ? N1 C1 C8 C10 -72.4(5) . . . . ? C2 C1 C8 C10 106.7(4) . . . . ? C8A C1 C8 C10 174(3) . . . . ? N1 C1 C8 C9 48.8(5) . . . . ? C2 C1 C8 C9 -132.1(4) . . . . ? C8A C1 C8 C9 -65(3) . . . . ? N1 C1 C8 C11 169.7(3) . . . . ? C2 C1 C8 C11 -11.3(5) . . . . ? C8A C1 C8 C11 56(2) . . . . ? N1 C1 C8A C9A -15.2(8) . . . . ? C2 C1 C8A C9A -178.4(6) . . . . ? C8 C1 C8A C9A 61(2) . . . . ? N1 C1 C8A C10A -132.3(7) . . . . ? C2 C1 C8A C10A 64.4(8) . . . . ? C8 C1 C8A C10A -56(2) . . . . ? N1 C1 C8A C11A 104.6(8) . . . . ? C2 C1 C8A C11A -58.7(8) . . . . ? C8 C1 C8A C11A -18E1(10) . . . . ? C17 C12 C13 C14 1.9(3) . . . . ? N1 C12 C13 C14 175.00(17) . . . . ? C17 C12 C13 C21 -174.21(19) . . . . ? N1 C12 C13 C21 -1.1(3) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C21 C13 C14 C15 176.4(2) . . . . ? C13 C14 C15 C16 -1.4(3) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C15 C16 C17 C12 1.5(3) . . . . ? C15 C16 C17 C18 -176.27(17) . . . . ? C13 C12 C17 C16 -2.7(3) . . . . ? N1 C12 C17 C16 -175.97(16) . . . . ? C13 C12 C17 C18 175.04(16) . . . . ? N1 C12 C17 C18 1.8(3) . . . . ? C16 C17 C18 C20 -34.4(2) . . . . ? C12 C17 C18 C20 147.94(18) . . . . ? C16 C17 C18 C19 90.1(2) . . . . ? C12 C17 C18 C19 -87.6(2) . . . . ? C14 C13 C21 C22 -79.5(3) . . . . ? C12 C13 C21 C22 96.6(3) . . . . ? C14 C13 C21 C23 42.2(3) . . . . ? C12 C13 C21 C23 -141.7(3) . . . . ? C29 C24 C25 C26 1.4(3) . . . . ? N2 C24 C25 C26 171.69(17) . . . . ? C29 C24 C25 C33 -175.45(17) . . . . ? N2 C24 C25 C33 -5.1(3) . . . . ? C24 C25 C26 C27 -0.4(3) . . . . ? C33 C25 C26 C27 176.39(19) . . . . ? C25 C26 C27 C28 -0.3(3) . . . . ? C26 C27 C28 C29 0.1(3) . . . . ? C27 C28 C29 C24 0.8(3) . . . . ? C27 C28 C29 C30 -176.6(2) . . . . ? C25 C24 C29 C28 -1.5(3) . . . . ? N2 C24 C29 C28 -171.75(18) . . . . ? C25 C24 C29 C30 175.84(17) . . . . ? N2 C24 C29 C30 5.6(3) . . . . ? C28 C29 C30 C32 -50.7(3) . . . . ? C24 C29 C30 C32 132.0(2) . . . . ? C28 C29 C30 C31 74.0(2) . . . . ? C24 C29 C30 C31 -103.3(2) . . . . ? C26 C25 C33 C35 -98.0(2) . . . . ? C24 C25 C33 C35 78.8(2) . . . . ? C26 C25 C33 C34 28.2(3) . . . . ? C24 C25 C33 C34 -155.05(18) . . . . ? N3 C36 C37 C36 -5.57(11) . . . 2 ? C38 C36 C37 C36 167.90(15) . . . 2 ? N3 C36 C38 C41 -10.9(2) . . . . ? C37 C36 C38 C41 176.04(15) . . . . ? N3 C36 C38 C40 -134.67(18) . . . . ? C37 C36 C38 C40 52.23(19) . . . . ? N3 C36 C38 C39 107.39(18) . . . . ? C37 C36 C38 C39 -65.71(18) . . . . ? C47 C42 C43 C44 -0.2(3) . . . . ? N3 C42 C43 C44 -173.72(17) . . . . ? C47 C42 C43 C51 179.07(17) . . . . ? N3 C42 C43 C51 5.6(3) . . . . ? C42 C43 C44 C45 -0.2(3) . . . . ? C51 C43 C44 C45 -179.5(2) . . . . ? C43 C44 C45 C46 -0.1(3) . . . . ? C44 C45 C46 C47 0.8(3) . . . . ? C45 C46 C47 C42 -1.2(3) . . . . ? C45 C46 C47 C48 177.63(19) . . . . ? C43 C42 C47 C46 1.0(3) . . . . ? N3 C42 C47 C46 174.34(16) . . . . ? C43 C42 C47 C48 -177.93(17) . . . . ? N3 C42 C47 C48 -4.5(3) . . . . ? C46 C47 C48 C49 -103.2(2) . . . . ? C42 C47 C48 C49 75.6(2) . . . . ? C46 C47 C48 C50 22.2(3) . . . . ? C42 C47 C48 C50 -159.00(17) . . . . ? C44 C43 C51 C52 -37.8(3) . . . . ? C42 C43 C51 C52 142.9(2) . . . . ? C44 C43 C51 C53 86.5(2) . . . . ? C42 C43 C51 C53 -92.8(2) . . . . ? C2 C1 N1 C12 -152.4(2) . . . . ? C8 C1 N1 C12 26.7(4) . . . . ? C8A C1 N1 C12 45.0(5) . . . . ? C17 C12 N1 C1 -119.8(2) . . . . ? C13 C12 N1 C1 66.9(3) . . . . ? C2 C3 N2 C24 -162.63(19) . . . . ? C4 C3 N2 C24 21.4(3) . . . . ? C29 C24 N2 C3 -112.7(2) . . . . ? C25 C24 N2 C3 76.9(3) . . . . ? C37 C36 N3 C42 -154.86(16) . . . . ? C38 C36 N3 C42 32.1(3) . . . . ? C43 C42 N3 C36 -123.3(2) . . . . ? C47 C42 N3 C36 63.0(3) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_shelxl _database_code_depnum_ccdc_archive 'CCDC 735241' _audit_creation_date 2009-07-15T15:33:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common '(BDI)Mg n-butyl THF' _chemical_formula_moiety 'C43 H70 Mg1 N2 O1' _chemical_formula_sum 'C43 H70 Mg N2 O' _chemical_formula_weight 655.32 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1942(1) _cell_length_b 26.3031(2) _cell_length_c 13.3982(1) _cell_angle_alpha 90 _cell_angle_beta 107.503(4) _cell_angle_gamma 90 _cell_volume 4098.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7405 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'triangular plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.062 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.7, which means that 90% of the reflections were measured at least 3.7 times. Phi and omega scans with a frame width of one degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.647053E-1 _diffrn_orient_matrix_ub_12 0.153717E-1 _diffrn_orient_matrix_ub_13 0.565135E-1 _diffrn_orient_matrix_ub_21 0.505961E-1 _diffrn_orient_matrix_ub_22 -0.22115E-2 _diffrn_orient_matrix_ub_23 -0.463424E-1 _diffrn_orient_matrix_ub_31 -0.254378E-1 _diffrn_orient_matrix_ub_32 0.347018E-1 _diffrn_orient_matrix_ub_33 -0.27987E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 54911 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 7242 _reflns_number_gt 5019 _reflns_threshold_expression >2\s(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 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;There is some disorder in this structure. One atom of the THF ligand is disordered over two sites: C(37A) and C(37B). The n-butyl ligand also is disordered with two positions each for atoms C(41), C(42) and C(43). SADI restraints were applied to the refinement of the disordered models for the THF and the n-butyl group. The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-C bond, was refined for each methyl group with the exception of methyl carbon atoms C(43A) and C(43B). The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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^ > 2\s(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 'w=1/[\s^2^(Fo^2^)+(0.0853P)^2^+0.6019P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7242 _refine_ls_number_parameters 476 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.082 _refine_ls_R_factor_gt 0.052 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.225 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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' Mg Mg 0.0486 0.0363 '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 0.006 '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 C1 C 0.64805(15) 0.08105(7) 0.78084(14) 0.0295(4) Uani 1 1 d . C . C2 C 0.68423(16) 0.05066(7) 0.71085(14) 0.0317(4) Uani 1 1 d . . . H2 H 0.6412 0.0202 0.6922 0.038 Uiso 1 1 calc R . . C3 C 0.77261(15) 0.05608(7) 0.66166(13) 0.0300(4) Uani 1 1 d . C . C4 C 0.81052(17) 0.00368(7) 0.62761(15) 0.0381(5) Uani 1 1 d . . . C5 C 0.8414(2) -0.03286(8) 0.72202(19) 0.0548(6) Uani 1 1 d . . . H5A H 0.9021 -0.0177 0.7797 0.082 Uiso 1 1 calc R . . H5B H 0.8684 -0.0652 0.7018 0.082 Uiso 1 1 calc R . . H5C H 0.7731 -0.0389 0.7446 0.082 Uiso 1 1 calc R . . C6 C 0.70873(19) -0.01830(8) 0.54090(17) 0.0512(6) Uani 1 1 d . . . H6A H 0.6446 -0.0249 0.569 0.077 Uiso 1 1 calc R . . H6B H 0.7321 -0.0501 0.5152 0.077 Uiso 1 1 calc R . . H6C H 0.6846 0.0061 0.4832 0.077 Uiso 1 1 calc R . . C7 C 0.91487(19) 0.00372(8) 0.58599(19) 0.0502(6) Uani 1 1 d . . . H7A H 0.8969 0.0236 0.5213 0.075 Uiso 1 1 calc R . . H7B H 0.9333 -0.0313 0.5718 0.075 Uiso 1 1 calc R . . H7C H 0.981 0.0188 0.6384 0.075 Uiso 1 1 calc R . . C8 C 0.55437(17) 0.05542(8) 0.82267(15) 0.0406(5) Uani 1 1 d . . . C9 C 0.53578(19) 0.07705(9) 0.92294(16) 0.0453(5) Uani 1 1 d . . . H9A H 0.5167 0.1133 0.9131 0.068 Uiso 1 1 calc R . . H9B H 0.6063 0.0729 0.9815 0.068 Uiso 1 1 calc R . . H9C H 0.4726 0.0588 0.9382 0.068 Uiso 1 1 calc R . . C10 C 0.5731(3) -0.00200(9) 0.8411(2) 0.0766(9) Uani 1 1 d . . . H10A H 0.5169 -0.0153 0.8735 0.115 Uiso 1 1 calc R . . H10B H 0.651 -0.0082 0.8875 0.115 Uiso 1 1 calc R . . H10C H 0.5633 -0.0191 0.774 0.115 Uiso 1 1 calc R . . C11 C 0.44015(19) 0.06291(12) 0.73462(19) 0.0710(8) Uani 1 1 d . . . H11A H 0.4462 0.0476 0.6698 0.107 Uiso 1 1 calc R . . H11B H 0.4241 0.0993 0.7236 0.107 Uiso 1 1 calc R . . H11C H 0.3776 0.0466 0.7545 0.107 Uiso 1 1 calc R . . C12 C 0.68771(16) 0.15520(7) 0.89586(14) 0.0302(4) Uani 1 1 d . C . C13 C 0.61383(16) 0.19612(7) 0.89640(14) 0.0327(4) Uani 1 1 d . . . C14 C 0.61975(17) 0.21900(8) 0.99186(15) 0.0392(5) Uani 1 1 d . . . H14 H 0.5699 0.2466 0.993 0.047 Uiso 1 1 calc R . . C15 C 0.69586(18) 0.20265(8) 1.08428(16) 0.0415(5) Uani 1 1 d . . . H15 H 0.6955 0.2174 1.1489 0.05 Uiso 1 1 calc R . . C16 C 0.77239(17) 0.16468(8) 1.08209(15) 0.0384(5) Uani 1 1 d . . . H16 H 0.8267 0.1542 1.1458 0.046 Uiso 1 1 calc R . . C17 C 0.77255(16) 0.14097(7) 0.98886(14) 0.0338(5) Uani 1 1 d . . . C18 C 0.86555(17) 0.10208(8) 0.99062(16) 0.0424(5) Uani 1 1 d . . . H18 H 0.8594 0.0937 0.9163 0.051 Uiso 1 1 calc R . . C19 C 0.9847(2) 0.12382(10) 1.0410(2) 0.0674(7) Uani 1 1 d . . . H19A H 0.9926 0.156 1.0069 0.101 Uiso 1 1 calc R . . H19B H 1.0427 0.0997 1.033 0.101 Uiso 1 1 calc R . . H19C H 0.9957 0.1298 1.1156 0.101 Uiso 1 1 calc R . . C20 C 0.8535(2) 0.05280(10) 1.0448(3) 0.0876(10) Uani 1 1 d . . . H20A H 0.8587 0.0597 1.1179 0.131 Uiso 1 1 calc R . . H20B H 0.9151 0.0294 1.0421 0.131 Uiso 1 1 calc R . . H20C H 0.7787 0.0373 1.0093 0.131 Uiso 1 1 calc R . . C21 C 0.52458(17) 0.21502(8) 0.79825(15) 0.0402(5) Uani 1 1 d . . . H21 H 0.5312 0.1941 0.7381 0.048 Uiso 1 1 calc R . . C22 C 0.40240(19) 0.20886(11) 0.8051(2) 0.0628(7) Uani 1 1 d . . . H22A H 0.3919 0.2311 0.8603 0.094 Uiso 1 1 calc R . . H22B H 0.39 0.1734 0.8216 0.094 Uiso 1 1 calc R . . H22C H 0.347 0.2182 0.738 0.094 Uiso 1 1 calc R . . C23 C 0.5469(2) 0.27046(9) 0.77621(18) 0.0576(6) Uani 1 1 d . . . H23A H 0.5401 0.2919 0.8339 0.086 Uiso 1 1 calc R . . H23B H 0.4904 0.2814 0.7109 0.086 Uiso 1 1 calc R . . H23C H 0.6245 0.2737 0.7697 0.086 Uiso 1 1 calc R . . C24 C 0.90342(16) 0.11161(7) 0.60203(14) 0.0319(4) Uani 1 1 d . C . C25 C 0.87672(16) 0.11771(7) 0.49289(15) 0.0355(5) Uani 1 1 d . . . C26 C 0.96511(18) 0.13002(8) 0.45115(17) 0.0418(5) Uani 1 1 d . . . H26 H 0.9482 0.1335 0.3775 0.05 Uiso 1 1 calc R . . C27 C 1.07606(18) 0.13731(8) 0.51374(18) 0.0465(6) Uani 1 1 d . . . H27 H 1.1353 0.1452 0.4837 0.056 Uiso 1 1 calc R . . C28 C 1.10000(18) 0.13299(8) 0.62034(18) 0.0455(5) Uani 1 1 d . . . H28 H 1.1766 0.1383 0.6635 0.055 Uiso 1 1 calc R . . C29 C 1.01573(16) 0.12111(8) 0.66707(16) 0.0376(5) Uani 1 1 d . . . C30 C 1.04882(17) 0.11871(9) 0.78569(17) 0.0484(6) Uani 1 1 d . . . H30 H 0.9768 0.1151 0.8062 0.058 Uiso 1 1 calc R . . C31 C 1.1254(3) 0.07338(11) 0.8286(2) 0.0898(10) Uani 1 1 d . . . H31A H 1.0821 0.0419 0.8057 0.135 Uiso 1 1 calc R . . H31B H 1.1512 0.0748 0.9052 0.135 Uiso 1 1 calc R . . H31C H 1.1924 0.0741 0.8025 0.135 Uiso 1 1 calc R . . C32 C 1.1099(2) 0.16725(10) 0.8353(2) 0.0707(8) Uani 1 1 d . . . H32A H 1.1186 0.1672 0.9105 0.106 Uiso 1 1 calc R . . H32B H 1.0645 0.1969 0.8026 0.106 Uiso 1 1 calc R . . H32C H 1.186 0.1689 0.8249 0.106 Uiso 1 1 calc R . . C33 C 0.75598(18) 0.11283(9) 0.41850(16) 0.0452(5) Uani 1 1 d . . . H33 H 0.7049 0.1008 0.4597 0.054 Uiso 1 1 calc R . . C34 C 0.7460(2) 0.07478(10) 0.32905(18) 0.0643(7) Uani 1 1 d . . . H34A H 0.7917 0.0869 0.2849 0.096 Uiso 1 1 calc R . . H34B H 0.6652 0.0717 0.2869 0.096 Uiso 1 1 calc R . . H34C H 0.7746 0.0415 0.3584 0.096 Uiso 1 1 calc R . . C35 C 0.7130(2) 0.16539(10) 0.37338(18) 0.0560(6) Uani 1 1 d . . . H35A H 0.7195 0.1894 0.4308 0.084 Uiso 1 1 calc R . . H35B H 0.6324 0.1629 0.3305 0.084 Uiso 1 1 calc R . . H35C H 0.7597 0.1774 0.3301 0.084 Uiso 1 1 calc R . . C36 C 0.50014(18) 0.13478(8) 0.50951(18) 0.0476(6) Uani 1 1 d D . . H36A H 0.5107 0.1038 0.5534 0.057 Uiso 0.7 1 calc PR A 1 H36B H 0.5086 0.1256 0.4405 0.057 Uiso 0.7 1 calc PR A 1 H36C H 0.4904 0.1101 0.5619 0.057 Uiso 0.3 1 calc PR A 2 H36D H 0.5269 0.1163 0.4569 0.057 Uiso 0.3 1 calc PR A 2 C37A C 0.3843(5) 0.15822(17) 0.4969(8) 0.0487(17) Uani 0.68(3) 1 d PD B 1 H37A H 0.3546 0.1479 0.555 0.058 Uiso 0.68(3) 1 calc PR B 1 H37B H 0.3285 0.1477 0.4298 0.058 Uiso 0.68(3) 1 calc PR B 1 C37B C 0.3884(12) 0.1611(4) 0.458(2) 0.070(6) Uani 0.32(3) 1 d PD B 2 H37C H 0.3245 0.1443 0.4761 0.084 Uiso 0.32(3) 1 calc PR B 2 H37D H 0.3715 0.1606 0.3807 0.084 Uiso 0.32(3) 1 calc PR B 2 C38 C 0.40420(19) 0.21532(9) 0.49877(19) 0.0543(6) Uani 1 1 d D . . H38A H 0.3598 0.2309 0.4315 0.065 Uiso 0.7 1 calc PR B 1 H38B H 0.3806 0.2314 0.5559 0.065 Uiso 0.7 1 calc PR B 1 H38C H 0.3586 0.2398 0.4464 0.065 Uiso 0.3 1 calc PR B 2 H38D H 0.3838 0.2188 0.5646 0.065 Uiso 0.3 1 calc PR B 2 C39 C 0.53191(17) 0.22192(8) 0.51673(16) 0.0441(5) Uani 1 1 d . B . H39A H 0.5481 0.2294 0.4501 0.053 Uiso 1 1 calc R . . H39B H 0.5625 0.25 0.5665 0.053 Uiso 1 1 calc R . . C40 C 0.82235(19) 0.23681(8) 0.70160(18) 0.0482(6) Uani 1 1 d D . . H40A H 0.777 0.2615 0.7288 0.058 Uiso 0.631(7) 1 calc PR C 1 H40B H 0.8963 0.2322 0.7573 0.058 Uiso 0.631(7) 1 calc PR C 1 H40C H 0.8188 0.2504 0.7695 0.058 Uiso 0.369(7) 1 calc PR C 2 H40D H 0.9038 0.2275 0.7126 0.058 Uiso 0.369(7) 1 calc PR C 2 C41A C 0.8492(5) 0.26181(17) 0.6116(3) 0.0570(14) Uani 0.631(7) 1 d PD C 1 H41A H 0.7767 0.2648 0.5535 0.068 Uiso 0.631(7) 1 calc PR C 1 H41B H 0.9007 0.239 0.5876 0.068 Uiso 0.631(7) 1 calc PR C 1 C42A C 0.9044(8) 0.3136(3) 0.6307(10) 0.092(4) Uani 0.631(7) 1 d PD C 1 H42A H 0.9773 0.3103 0.6883 0.111 Uiso 0.631(7) 1 calc PR C 1 H42B H 0.9247 0.3234 0.5672 0.111 Uiso 0.631(7) 1 calc PR C 1 C43A C 0.8392(6) 0.3550(2) 0.6567(6) 0.111(3) Uani 0.631(7) 1 d PD C 1 H43A H 0.886 0.386 0.6694 0.167 Uiso 0.631(7) 1 calc PR C 1 H43B H 0.8184 0.3463 0.7198 0.167 Uiso 0.631(7) 1 calc PR C 1 H43C H 0.7692 0.3607 0.5984 0.167 Uiso 0.631(7) 1 calc PR C 1 C41B C 0.8027(6) 0.2815(3) 0.6314(6) 0.053(2) Uani 0.369(7) 1 d PD C 2 H41C H 0.7314 0.2986 0.6342 0.064 Uiso 0.369(7) 1 calc PR C 2 H41D H 0.7892 0.2692 0.5588 0.064 Uiso 0.369(7) 1 calc PR C 2 C42B C 0.8987(10) 0.3208(5) 0.6547(17) 0.077(6) Uani 0.369(7) 1 d PD C 2 H42C H 0.9154 0.3315 0.7286 0.092 Uiso 0.369(7) 1 calc PR C 2 H42D H 0.9688 0.3042 0.6475 0.092 Uiso 0.369(7) 1 calc PR C 2 C43B C 0.8769(8) 0.3662(3) 0.5895(7) 0.087(3) Uani 0.369(7) 1 d PD C 2 H43D H 0.94 0.3904 0.6161 0.13 Uiso 0.369(7) 1 calc PR C 2 H43E H 0.8045 0.3819 0.5913 0.13 Uiso 0.369(7) 1 calc PR C 2 H43F H 0.8713 0.357 0.5173 0.13 Uiso 0.369(7) 1 calc PR C 2 Mg Mg 0.73416(5) 0.16628(2) 0.68449(5) 0.03025(18) Uani 1 1 d . B . N1 N 0.68328(12) 0.12966(5) 0.79971(11) 0.0286(4) Uani 1 1 d . . . N2 N 0.81292(12) 0.10138(6) 0.64816(11) 0.0294(4) Uani 1 1 d . . . O O 0.58288(11) 0.17355(5) 0.55998(10) 0.0367(3) Uani 1 1 d . B . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0279(10) 0.0312(11) 0.0278(10) 0.0024(8) 0.0057(8) -0.0019(8) C2 0.0339(10) 0.0281(10) 0.0321(10) -0.0019(8) 0.0087(8) -0.0058(8) C3 0.0312(10) 0.0300(11) 0.0263(10) -0.0025(8) 0.0047(8) -0.0024(8) C4 0.0435(11) 0.0297(11) 0.0440(12) -0.0051(9) 0.0175(10) -0.0011(9) C5 0.0628(15) 0.0391(13) 0.0656(16) 0.0094(11) 0.0238(12) 0.0131(11) C6 0.0591(14) 0.0404(13) 0.0567(14) -0.0160(11) 0.0217(12) -0.0086(11) C7 0.0569(14) 0.0332(12) 0.0704(16) -0.0066(11) 0.0339(12) 0.0059(10) C8 0.0441(12) 0.0425(12) 0.0401(12) -0.0027(10) 0.0200(10) -0.0120(10) C9 0.0483(13) 0.0503(14) 0.0443(13) -0.0005(10) 0.0245(10) -0.0115(10) C10 0.121(2) 0.0440(15) 0.094(2) -0.0032(14) 0.0771(19) -0.0181(15) C11 0.0403(13) 0.124(2) 0.0519(15) -0.0117(15) 0.0180(11) -0.0317(15) C12 0.0321(10) 0.0317(11) 0.0277(10) 0.0006(8) 0.0103(8) -0.0036(8) C13 0.0349(10) 0.0336(11) 0.0316(11) -0.0005(8) 0.0130(8) -0.0016(9) C14 0.0428(12) 0.0388(12) 0.0386(12) -0.0046(9) 0.0163(10) -0.0004(9) C15 0.0475(12) 0.0488(13) 0.0311(11) -0.0098(10) 0.0163(10) -0.0100(11) C16 0.0396(11) 0.0459(13) 0.0263(10) 0.0012(9) 0.0049(9) -0.0076(10) C17 0.0339(10) 0.0358(11) 0.0301(10) 0.0032(8) 0.0072(9) -0.0047(9) C18 0.0436(12) 0.0449(13) 0.0347(11) 0.0039(9) 0.0057(9) 0.0067(10) C19 0.0445(14) 0.0731(19) 0.0834(19) -0.0120(15) 0.0174(13) 0.0013(13) C20 0.0662(18) 0.0583(18) 0.133(3) 0.0372(18) 0.0212(18) 0.0165(14) C21 0.0410(11) 0.0448(13) 0.0347(11) -0.0001(9) 0.0113(9) 0.0125(10) C22 0.0429(13) 0.086(2) 0.0572(15) 0.0105(14) 0.0122(11) 0.0182(13) C23 0.0810(18) 0.0436(14) 0.0460(14) 0.0044(11) 0.0156(13) 0.0134(13) C24 0.0343(10) 0.0265(10) 0.0385(11) -0.0021(8) 0.0165(9) -0.0009(8) C25 0.0397(11) 0.0307(11) 0.0396(12) -0.0020(9) 0.0173(9) -0.0029(9) C26 0.0506(13) 0.0356(12) 0.0469(13) 0.0008(10) 0.0263(11) 0.0000(10) C27 0.0410(13) 0.0444(13) 0.0642(15) 0.0024(11) 0.0310(12) 0.0004(10) C28 0.0341(11) 0.0443(13) 0.0600(15) -0.0019(11) 0.0172(10) -0.0040(10) C29 0.0331(11) 0.0362(11) 0.0448(12) -0.0029(9) 0.0135(9) 0.0005(9) C30 0.0311(11) 0.0670(16) 0.0459(13) -0.0031(11) 0.0097(10) -0.0061(11) C31 0.128(3) 0.0683(19) 0.0578(17) 0.0095(15) 0.0043(18) 0.0145(19) C32 0.0658(17) 0.0755(19) 0.0630(17) -0.0179(14) 0.0076(14) -0.0025(15) C33 0.0472(12) 0.0585(15) 0.0316(11) 0.0015(10) 0.0146(9) -0.0086(11) C34 0.0788(18) 0.0745(18) 0.0427(14) -0.0131(12) 0.0230(13) -0.0243(14) C35 0.0492(13) 0.0764(18) 0.0420(13) 0.0143(12) 0.0130(11) 0.0022(12) C36 0.0401(12) 0.0478(14) 0.0497(13) 0.0013(11) 0.0057(10) -0.0063(10) C37A 0.033(2) 0.066(3) 0.047(3) 0.005(2) 0.0117(19) 0.0012(19) C37B 0.049(7) 0.069(8) 0.075(11) -0.001(6) -0.005(6) 0.005(5) C38 0.0450(13) 0.0638(16) 0.0517(14) 0.0077(12) 0.0110(11) 0.0156(12) C39 0.0477(13) 0.0411(13) 0.0407(12) 0.0101(10) 0.0093(10) 0.0102(10) C40 0.0492(13) 0.0397(13) 0.0527(14) 0.0028(11) 0.0109(11) -0.0036(11) C41A 0.069(3) 0.043(3) 0.063(3) 0.002(2) 0.025(2) -0.018(2) C42A 0.092(7) 0.075(6) 0.116(7) 0.010(4) 0.041(6) -0.028(4) C43A 0.149(6) 0.041(3) 0.166(7) 0.006(4) 0.083(5) -0.007(4) C41B 0.055(5) 0.038(4) 0.072(5) -0.006(4) 0.028(4) -0.008(3) C42B 0.050(7) 0.037(7) 0.114(11) 0.029(7) -0.021(7) -0.019(5) C43B 0.114(7) 0.058(5) 0.085(6) 0.011(4) 0.025(5) -0.038(5) Mg 0.0311(4) 0.0286(4) 0.0318(4) 0.0012(3) 0.0105(3) -0.0003(3) N1 0.0282(8) 0.0298(9) 0.0271(8) 0.0002(7) 0.0075(7) 0.0006(7) N2 0.0287(8) 0.0299(9) 0.0307(9) -0.0009(7) 0.0107(7) -0.0031(7) O 0.0356(7) 0.0357(8) 0.0360(7) 0.0041(6) 0.0064(6) 0.0015(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.348(2) . ? C1 C2 1.401(3) . ? C1 C8 1.568(3) . ? C2 C3 1.429(3) . ? C2 H2 0.95 . ? C3 N2 1.322(2) . ? C3 C4 1.565(3) . ? C4 C7 1.535(3) . ? C4 C6 1.535(3) . ? C4 C5 1.542(3) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C10 1.536(3) . ? C8 C9 1.537(3) . ? C8 C11 1.544(3) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 C13 1.405(3) . ? C12 C17 1.410(3) . ? C12 N1 1.439(2) . ? C13 C14 1.396(3) . ? C13 C21 1.517(3) . ? C14 C15 1.374(3) . ? C14 H14 0.95 . ? C15 C16 1.373(3) . ? C15 H15 0.95 . ? C16 C17 1.397(3) . ? C16 H16 0.95 . ? C17 C18 1.522(3) . ? C18 C20 1.514(3) . ? C18 C19 1.518(3) . ? C18 H18 1 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C23 1.528(3) . ? C21 C22 1.529(3) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C29 1.407(3) . ? C24 C25 1.408(3) . ? C24 N2 1.443(2) . ? C25 C26 1.394(3) . ? C25 C33 1.515(3) . ? C26 C27 1.374(3) . ? C26 H26 0.95 . ? C27 C28 1.374(3) . ? C27 H27 0.95 . ? C28 C29 1.390(3) . ? C28 H28 0.95 . ? C29 C30 1.519(3) . ? C30 C31 1.517(3) . ? C30 C32 1.526(3) . ? C30 H30 1 . ? C31 H31A 0.98 . ? C31 H31B 0.98 . ? C31 H31C 0.98 . ? C32 H32A 0.98 . ? C32 H32B 0.98 . ? C32 H32C 0.98 . ? C33 C35 1.537(3) . ? C33 C34 1.538(3) . ? C33 H33 1 . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C36 O 1.451(2) . ? C36 C37B 1.499(8) . ? C36 C37A 1.503(5) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C36 H36C 0.99 . ? C36 H36D 0.99 . ? C37A C38 1.520(5) . ? C37A H37A 0.99 . ? C37A H37B 0.99 . ? C37B C38 1.520(8) . ? C37B H37C 0.99 . ? C37B H37D 0.99 . ? C38 C39 1.513(3) . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C38 H38C 0.99 . ? C38 H38D 0.99 . ? C39 O 1.457(2) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C40 C41B 1.479(6) . ? C40 C41A 1.494(4) . ? C40 Mg 2.122(2) . ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? C40 H40C 0.99 . ? C40 H40D 0.99 . ? C41A C42A 1.506(6) . ? C41A H41A 0.99 . ? C41A H41B 0.99 . ? C42A C43A 1.452(10) . ? C42A H42A 0.99 . ? C42A H42B 0.99 . ? C43A H43A 0.98 . ? C43A H43B 0.98 . ? C43A H43C 0.98 . ? C41B C42B 1.523(7) . ? C41B H41C 0.99 . ? C41B H41D 0.99 . ? C42B C43B 1.456(9) . ? C42B H42C 0.99 . ? C42B H42D 0.99 . ? C43B H43D 0.98 . ? C43B H43E 0.98 . ? C43B H43F 0.98 . ? Mg N1 2.0669(15) . ? Mg N2 2.0868(16) . ? Mg O 2.0908(14) . ? 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 N1 C1 C2 121.33(16) . . ? N1 C1 C8 124.48(16) . . ? C2 C1 C8 113.82(16) . . ? C1 C2 C3 133.21(17) . . ? C1 C2 H2 113.4 . . ? C3 C2 H2 113.4 . . ? N2 C3 C2 121.06(16) . . ? N2 C3 C4 126.83(16) . . ? C2 C3 C4 112.11(16) . . ? C7 C4 C6 107.17(17) . . ? C7 C4 C5 105.91(17) . . ? C6 C4 C5 109.16(18) . . ? C7 C4 C3 117.07(16) . . ? C6 C4 C3 108.04(16) . . ? C5 C4 C3 109.29(16) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C8 C9 106.10(17) . . ? C10 C8 C11 107.7(2) . . ? C9 C8 C11 106.52(18) . . ? C10 C8 C1 113.03(17) . . ? C9 C8 C1 117.90(16) . . ? C11 C8 C1 105.00(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 120.00(17) . . ? C13 C12 N1 120.71(16) . . ? C17 C12 N1 119.15(16) . . ? C14 C13 C12 118.59(17) . . ? C14 C13 C21 118.62(17) . . ? C12 C13 C21 122.73(16) . . ? C15 C14 C13 121.71(19) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 C15 C14 119.17(18) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 121.85(18) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C12 118.28(18) . . ? C16 C17 C18 119.19(17) . . ? C12 C17 C18 122.50(17) . . ? C20 C18 C19 109.1(2) . . ? C20 C18 C17 113.78(19) . . ? C19 C18 C17 111.27(18) . . ? C20 C18 H18 107.5 . . ? C19 C18 H18 107.5 . . ? C17 C18 H18 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 C23 110.93(18) . . ? C13 C21 C22 111.79(17) . . ? C23 C21 C22 110.26(18) . . ? C13 C21 H21 107.9 . . ? C23 C21 H21 107.9 . . ? C22 C21 H21 107.9 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 C25 120.06(17) . . ? C29 C24 N2 119.68(16) . . ? C25 C24 N2 119.87(16) . . ? C26 C25 C24 118.54(18) . . ? C26 C25 C33 118.14(18) . . ? C24 C25 C33 123.30(17) . . ? C27 C26 C25 121.7(2) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C28 C27 C26 119.03(19) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 120.5 . . ? C27 C28 C29 122.1(2) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C28 C29 C24 118.33(19) . . ? C28 C29 C30 118.74(18) . . ? C24 C29 C30 122.92(17) . . ? C31 C30 C29 111.6(2) . . ? C31 C30 C32 109.1(2) . . ? C29 C30 C32 111.3(2) . . ? C31 C30 H30 108.2 . . ? C29 C30 H30 108.2 . . ? C32 C30 H30 108.2 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C25 C33 C35 109.37(18) . . ? C25 C33 C34 113.68(19) . . ? C35 C33 C34 109.95(18) . . ? C25 C33 H33 107.9 . . ? C35 C33 H33 107.9 . . ? C34 C33 H33 107.9 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O C36 C37B 107.4(4) . . ? O C36 C37A 105.2(3) . . ? O C36 H36A 110.7 . . ? C37A C36 H36A 110.7 . . ? O C36 H36B 110.7 . . ? C37A C36 H36B 110.7 . . ? H36A C36 H36B 108.8 . . ? O C36 H36C 110.2 . . ? C37B C36 H36C 110.2 . . ? O C36 H36D 110.2 . . ? C37B C36 H36D 110.2 . . ? H36C C36 H36D 108.5 . . ? C36 C37A C38 105.3(3) . . ? C36 C37A H37A 110.7 . . ? C38 C37A H37A 110.7 . . ? C36 C37A H37B 110.7 . . ? C38 C37A H37B 110.7 . . ? H37A C37A H37B 108.8 . . ? C36 C37B C38 105.5(5) . . ? C36 C37B H37C 110.6 . . ? C38 C37B H37C 110.6 . . ? C36 C37B H37D 110.6 . . ? C38 C37B H37D 110.6 . . ? H37C C37B H37D 108.8 . . ? C39 C38 C37B 100.2(7) . . ? C39 C38 C37A 105.5(2) . . ? C39 C38 H38A 110.6 . . ? C37A C38 H38A 110.6 . . ? C39 C38 H38B 110.6 . . ? C37A C38 H38B 110.6 . . ? H38A C38 H38B 108.8 . . ? C39 C38 H38C 111.7 . . ? C37B C38 H38C 111.7 . . ? C39 C38 H38D 111.7 . . ? C37B C38 H38D 111.7 . . ? H38C C38 H38D 109.5 . . ? O C39 C38 104.99(17) . . ? O C39 H39A 110.7 . . ? C38 C39 H39A 110.7 . . ? O C39 H39B 110.7 . . ? C38 C39 H39B 110.7 . . ? H39A C39 H39B 108.8 . . ? C41B C40 Mg 130.2(3) . . ? C41A C40 Mg 121.6(2) . . ? C41A C40 H40A 106.9 . . ? Mg C40 H40A 106.9 . . ? C41A C40 H40B 106.9 . . ? Mg C40 H40B 106.9 . . ? H40A C40 H40B 106.7 . . ? C41B C40 H40C 104.7 . . ? Mg C40 H40C 104.7 . . ? C41B C40 H40D 104.7 . . ? Mg C40 H40D 104.7 . . ? H40C C40 H40D 105.7 . . ? C40 C41A C42A 117.1(5) . . ? C40 C41A H41A 108 . . ? C42A C41A H41A 108 . . ? C40 C41A H41B 108 . . ? C42A C41A H41B 108 . . ? H41A C41A H41B 107.3 . . ? C43A C42A C41A 118.1(6) . . ? C43A C42A H42A 107.8 . . ? C41A C42A H42A 107.8 . . ? C43A C42A H42B 107.8 . . ? C41A C42A H42B 107.8 . . ? H42A C42A H42B 107.1 . . ? C42A C43A H43A 109.5 . . ? C42A C43A H43B 109.5 . . ? H43A C43A H43B 109.5 . . ? C42A C43A H43C 109.5 . . ? H43A C43A H43C 109.5 . . ? H43B C43A H43C 109.5 . . ? C40 C41B C42B 116.2(6) . . ? C40 C41B H41C 108.2 . . ? C42B C41B H41C 108.2 . . ? C40 C41B H41D 108.2 . . ? C42B C41B H41D 108.2 . . ? H41C C41B H41D 107.4 . . ? C43B C42B C41B 116.3(8) . . ? C43B C42B H42C 108.2 . . ? C41B C42B H42C 108.2 . . ? C43B C42B H42D 108.2 . . ? C41B C42B H42D 108.2 . . ? H42C C42B H42D 107.4 . . ? C42B C43B H43D 109.5 . . ? C42B C43B H43E 109.5 . . ? H43D C43B H43E 109.5 . . ? C42B C43B H43F 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? N1 Mg N2 93.19(6) . . ? N1 Mg O 104.33(6) . . ? N2 Mg O 104.25(6) . . ? N1 Mg C40 125.66(8) . . ? N2 Mg C40 119.12(8) . . ? O Mg C40 107.65(7) . . ? C1 N1 C12 122.31(14) . . ? C1 N1 Mg 116.88(11) . . ? C12 N1 Mg 120.80(11) . . ? C3 N2 C24 126.19(15) . . ? C3 N2 Mg 119.29(12) . . ? C24 N2 Mg 114.34(11) . . ? C36 O C39 105.93(15) . . ? C36 O Mg 129.11(12) . . ? C39 O Mg 124.44(12) . . ? 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 N1 C1 C2 C3 13.2(3) . . . . ? C8 C1 C2 C3 -173.49(19) . . . . ? C1 C2 C3 N2 -23.8(3) . . . . ? C1 C2 C3 C4 156.7(2) . . . . ? N2 C3 C4 C7 7.8(3) . . . . ? C2 C3 C4 C7 -172.78(17) . . . . ? N2 C3 C4 C6 -113.2(2) . . . . ? C2 C3 C4 C6 66.2(2) . . . . ? N2 C3 C4 C5 128.2(2) . . . . ? C2 C3 C4 C5 -52.4(2) . . . . ? N1 C1 C8 C10 -150.0(2) . . . . ? C2 C1 C8 C10 36.9(2) . . . . ? N1 C1 C8 C9 -25.5(3) . . . . ? C2 C1 C8 C9 161.41(18) . . . . ? N1 C1 C8 C11 92.8(2) . . . . ? C2 C1 C8 C11 -80.2(2) . . . . ? C17 C12 C13 C14 -5.6(3) . . . . ? N1 C12 C13 C14 178.71(16) . . . . ? C17 C12 C13 C21 177.00(17) . . . . ? N1 C12 C13 C21 1.3(3) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C21 C13 C14 C15 177.78(18) . . . . ? C13 C14 C15 C16 3.6(3) . . . . ? C14 C15 C16 C17 -2.2(3) . . . . ? C15 C16 C17 C12 -3.0(3) . . . . ? C15 C16 C17 C18 175.25(18) . . . . ? C13 C12 C17 C16 6.9(3) . . . . ? N1 C12 C17 C16 -177.32(16) . . . . ? C13 C12 C17 C18 -171.29(18) . . . . ? N1 C12 C17 C18 4.5(3) . . . . ? C16 C17 C18 C20 70.3(3) . . . . ? C12 C17 C18 C20 -111.5(2) . . . . ? C16 C17 C18 C19 -53.5(3) . . . . ? C12 C17 C18 C19 124.8(2) . . . . ? C14 C13 C21 C23 63.3(2) . . . . ? C12 C13 C21 C23 -119.3(2) . . . . ? C14 C13 C21 C22 -60.2(3) . . . . ? C12 C13 C21 C22 117.1(2) . . . . ? C29 C24 C25 C26 4.1(3) . . . . ? N2 C24 C25 C26 176.91(17) . . . . ? C29 C24 C25 C33 -174.37(18) . . . . ? N2 C24 C25 C33 -1.5(3) . . . . ? C24 C25 C26 C27 -1.4(3) . . . . ? C33 C25 C26 C27 177.13(19) . . . . ? C25 C26 C27 C28 -0.9(3) . . . . ? C26 C27 C28 C29 0.5(3) . . . . ? C27 C28 C29 C24 2.2(3) . . . . ? C27 C28 C29 C30 -178.1(2) . . . . ? C25 C24 C29 C28 -4.4(3) . . . . ? N2 C24 C29 C28 -177.29(17) . . . . ? C25 C24 C29 C30 175.85(18) . . . . ? N2 C24 C29 C30 3.0(3) . . . . ? C28 C29 C30 C31 -69.6(3) . . . . ? C24 C29 C30 C31 110.1(2) . . . . ? C28 C29 C30 C32 52.6(3) . . . . ? C24 C29 C30 C32 -127.7(2) . . . . ? C26 C25 C33 C35 -68.1(2) . . . . ? C24 C25 C33 C35 110.3(2) . . . . ? C26 C25 C33 C34 55.2(3) . . . . ? C24 C25 C33 C34 -126.4(2) . . . . ? O C36 C37A C38 23.1(6) . . . . ? C37B C36 C37A C38 -75.9(13) . . . . ? O C36 C37B C38 -11(2) . . . . ? C37A C36 C37B C38 76.2(13) . . . . ? C36 C37B C38 C39 31(2) . . . . ? C36 C37B C38 C37A -76.4(13) . . . . ? C36 C37A C38 C39 -2.2(6) . . . . ? C36 C37A C38 C37B 75.5(13) . . . . ? C37B C38 C39 O -40.0(13) . . . . ? C37A C38 C39 O -19.4(4) . . . . ? C41B C40 C41A C42A 59.4(7) . . . . ? Mg C40 C41A C42A 175.7(5) . . . . ? C40 C41A C42A C43A -63.8(11) . . . . ? C41A C40 C41B C42B -77.5(14) . . . . ? Mg C40 C41B C42B -165.9(11) . . . . ? C40 C41B C42B C43B -176.5(15) . . . . ? C41B C40 Mg N1 -135.3(5) . . . . ? C41A C40 Mg N1 -176.2(3) . . . . ? C41B C40 Mg N2 106.1(5) . . . . ? C41A C40 Mg N2 65.2(3) . . . . ? C41B C40 Mg O -12.1(5) . . . . ? C41A C40 Mg O -53.0(3) . . . . ? C2 C1 N1 C12 -154.77(17) . . . . ? C8 C1 N1 C12 32.7(3) . . . . ? C2 C1 N1 Mg 24.2(2) . . . . ? C8 C1 N1 Mg -148.36(14) . . . . ? C13 C12 N1 C1 -113.2(2) . . . . ? C17 C12 N1 C1 71.1(2) . . . . ? C13 C12 N1 Mg 67.9(2) . . . . ? C17 C12 N1 Mg -107.79(17) . . . . ? N2 Mg N1 C1 -38.02(13) . . . . ? O Mg N1 C1 67.57(13) . . . . ? C40 Mg N1 C1 -167.79(13) . . . . ? N2 Mg N1 C12 140.95(13) . . . . ? O Mg N1 C12 -113.46(13) . . . . ? C40 Mg N1 C12 11.18(17) . . . . ? C2 C3 N2 C24 178.46(16) . . . . ? C4 C3 N2 C24 -2.2(3) . . . . ? C2 C3 N2 Mg -6.7(2) . . . . ? C4 C3 N2 Mg 172.66(13) . . . . ? C29 C24 N2 C3 -99.5(2) . . . . ? C25 C24 N2 C3 87.6(2) . . . . ? C29 C24 N2 Mg 85.41(18) . . . . ? C25 C24 N2 Mg -87.45(18) . . . . ? N1 Mg N2 C3 29.63(14) . . . . ? O Mg N2 C3 -76.03(14) . . . . ? C40 Mg N2 C3 164.00(13) . . . . ? N1 Mg N2 C24 -154.91(12) . . . . ? O Mg N2 C24 99.43(12) . . . . ? C40 Mg N2 C24 -20.54(15) . . . . ? C37B C36 O C39 -14.4(15) . . . . ? C37A C36 O C39 -36.2(4) . . . . ? C37B C36 O Mg 157.4(15) . . . . ? C37A C36 O Mg 135.6(4) . . . . ? C38 C39 O C36 34.6(2) . . . . ? C38 C39 O Mg -137.70(14) . . . . ? N1 Mg O C36 -52.44(16) . . . . ? N2 Mg O C36 44.69(16) . . . . ? C40 Mg O C36 172.12(16) . . . . ? N1 Mg O C39 118.06(14) . . . . ? N2 Mg O C39 -144.81(14) . . . . ? C40 Mg O C39 -17.39(16) . . . . ? # END of CIF #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-26 at 14:27:01 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1405 _database_code_depnum_ccdc_archive 'CCDC 735242' _audit_creation_date 2008-02-26T14:27:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common (BDI)ZnEt _chemical_formula_moiety 'C37 H58 N2 Zn1' _chemical_formula_sum 'C37 H58 N2 Zn' _chemical_formula_weight 596.22 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 16.7410(2) _cell_length_b 17.8475(2) _cell_length_c 24.4862(3) _cell_angle_alpha 90 _cell_angle_beta 108.584(1) _cell_angle_gamma 90 _cell_volume 6934.63(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12605 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'rectangular chunk' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.3, which means that 90% of the reflections were measured at least 3.3 times. Phi and omega scans with a frame width of one degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. There are two molecules in the asymmetric unit and they are labeled as A and B. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.78585E-2 _diffrn_orient_matrix_ub_12 0.37919E-2 _diffrn_orient_matrix_ub_13 0.624127E-1 _diffrn_orient_matrix_ub_21 0.300245E-1 _diffrn_orient_matrix_ub_22 0.472979E-1 _diffrn_orient_matrix_ub_23 0.9068E-3 _diffrn_orient_matrix_ub_31 -0.35815E-1 _diffrn_orient_matrix_ub_32 0.225822E-1 _diffrn_orient_matrix_ub_33 0.79834E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 81289 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 12236 _reflns_number_gt 8945 _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 'SHELXS-97 (Sheldrick, 1997)' _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 ;The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+2.1487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 12236 _refine_ls_number_parameters 721 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.443 _refine_diff_density_min -0.54 _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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Zn1A Zn 0.365577(19) 0.639668(17) 0.091421(13) 0.02862(10) Uani 1 1 d . . . N1A N 0.37968(12) 0.71810(11) 0.03914(9) 0.0255(5) Uani 1 1 d . . . N2A N 0.36343(13) 0.70493(11) 0.15572(9) 0.0269(5) Uani 1 1 d . . . C1A C 0.38407(15) 0.79111(14) 0.05234(11) 0.0250(6) Uani 1 1 d . . . C2A C 0.37637(15) 0.81624(15) 0.10463(10) 0.0269(6) Uani 1 1 d . . . H2A H 0.3784 0.8693 0.1083 0.032 Uiso 1 1 calc R . . C3A C 0.36619(15) 0.77954(14) 0.15313(11) 0.0262(6) Uani 1 1 d . . . C4A C 0.36031(17) 0.83523(15) 0.20101(11) 0.0317(6) Uani 1 1 d . . . C5A C 0.44505(18) 0.87635(15) 0.22491(13) 0.0405(7) Uani 1 1 d . . . H5A H 0.4606 0.8982 0.193 0.061 Uiso 1 1 calc R . . H5B H 0.4887 0.8408 0.2459 0.061 Uiso 1 1 calc R . . H5C H 0.4399 0.9163 0.2511 0.061 Uiso 1 1 calc R . . C6A C 0.3397(2) 0.80271(16) 0.25307(12) 0.0447(8) Uani 1 1 d . . . H6A H 0.3824 0.7655 0.2724 0.067 Uiso 1 1 calc R . . H6B H 0.2842 0.7787 0.2399 0.067 Uiso 1 1 calc R . . H6C H 0.3393 0.8431 0.2801 0.067 Uiso 1 1 calc R . . C7A C 0.28989(17) 0.89224(16) 0.17363(12) 0.0381(7) Uani 1 1 d . . . H7A H 0.2994 0.915 0.1398 0.057 Uiso 1 1 calc R . . H7B H 0.2902 0.9314 0.2018 0.057 Uiso 1 1 calc R . . H7C H 0.2352 0.8667 0.1619 0.057 Uiso 1 1 calc R . . C8A C 0.39646(16) 0.85427(14) 0.01134(11) 0.0276(6) Uani 1 1 d . . . C9A C 0.4074(2) 0.93292(16) 0.03811(13) 0.0479(8) Uani 1 1 d . . . H9A H 0.4563 0.9333 0.0732 0.072 Uiso 1 1 calc R . . H9B H 0.3567 0.9464 0.0477 0.072 Uiso 1 1 calc R . . H9C H 0.4161 0.9692 0.0105 0.072 Uiso 1 1 calc R . . C10A C 0.31895(19) 0.85947(17) -0.04304(13) 0.0448(8) Uani 1 1 d . . . H10A H 0.2685 0.8684 -0.0319 0.067 Uiso 1 1 calc R . . H10B H 0.3125 0.8124 -0.0646 0.067 Uiso 1 1 calc R . . H10C H 0.3265 0.9009 -0.0672 0.067 Uiso 1 1 calc R . . C11A C 0.47438(19) 0.84052(17) -0.00726(14) 0.0473(8) Uani 1 1 d . . . H11A H 0.5245 0.8376 0.0269 0.071 Uiso 1 1 calc R . . H11B H 0.4808 0.8818 -0.0319 0.071 Uiso 1 1 calc R . . H11C H 0.4676 0.7933 -0.0287 0.071 Uiso 1 1 calc R . . C12A C 0.38375(16) 0.68577(13) -0.01417(11) 0.0260(6) Uani 1 1 d . . . C13A C 0.30871(16) 0.67345(14) -0.05997(11) 0.0292(6) Uani 1 1 d . . . C14A C 0.31432(19) 0.63646(15) -0.10891(12) 0.0371(7) Uani 1 1 d . . . H14A H 0.2645 0.6287 -0.1405 0.045 Uiso 1 1 calc R . . C15A C 0.3896(2) 0.61123(16) -0.11242(13) 0.0441(8) Uani 1 1 d . . . H15A H 0.3919 0.5873 -0.1466 0.053 Uiso 1 1 calc R . . C16A C 0.46207(19) 0.62042(15) -0.06667(12) 0.0386(7) Uani 1 1 d . . . H16A H 0.5139 0.602 -0.0694 0.046 Uiso 1 1 calc R . . C17A C 0.46089(16) 0.65626(14) -0.01629(11) 0.0304(6) Uani 1 1 d . . . C18A C 0.54108(16) 0.65905(16) 0.03540(12) 0.0356(7) Uani 1 1 d . . . H18A H 0.5319 0.6948 0.0643 0.043 Uiso 1 1 calc R . . C19A C 0.55800(18) 0.58101(16) 0.06307(13) 0.0460(8) Uani 1 1 d . . . H19A H 0.6093 0.5825 0.0965 0.069 Uiso 1 1 calc R . . H19B H 0.5652 0.5449 0.0349 0.069 Uiso 1 1 calc R . . H19C H 0.5102 0.5659 0.0755 0.069 Uiso 1 1 calc R . . C20A C 0.61842(18) 0.68488(18) 0.02009(15) 0.0518(9) Uani 1 1 d . . . H20A H 0.6677 0.6854 0.0549 0.078 Uiso 1 1 calc R . . H20B H 0.6086 0.7354 0.0036 0.078 Uiso 1 1 calc R . . H20C H 0.6285 0.6503 -0.0081 0.078 Uiso 1 1 calc R . . C21A C 0.22287(16) 0.69460(15) -0.05542(11) 0.0327(6) Uani 1 1 d . . . H21A H 0.232 0.7318 -0.0235 0.039 Uiso 1 1 calc R . . C22A C 0.18263(18) 0.62441(16) -0.03912(13) 0.0435(8) Uani 1 1 d . . . H22A H 0.1274 0.6373 -0.0359 0.065 Uiso 1 1 calc R . . H22B H 0.2191 0.605 -0.0021 0.065 Uiso 1 1 calc R . . H22C H 0.1757 0.5861 -0.0689 0.065 Uiso 1 1 calc R . . C23A C 0.16256(18) 0.72969(17) -0.11040(12) 0.0416(7) Uani 1 1 d . . . H23A H 0.109 0.7419 -0.1042 0.062 Uiso 1 1 calc R . . H23B H 0.1524 0.694 -0.1423 0.062 Uiso 1 1 calc R . . H23C H 0.1878 0.7755 -0.1198 0.062 Uiso 1 1 calc R . . C24A C 0.36247(17) 0.66265(14) 0.20550(11) 0.0302(6) Uani 1 1 d . . . C25A C 0.28659(18) 0.63005(15) 0.20644(12) 0.0345(7) Uani 1 1 d . . . C26A C 0.2878(2) 0.58896(18) 0.25491(14) 0.0500(8) Uani 1 1 d . . . H26A H 0.2367 0.5683 0.2573 0.06 Uiso 1 1 calc R . . C27A C 0.3608(2) 0.5776(2) 0.29924(15) 0.0599(10) Uani 1 1 d . . . H27A H 0.3599 0.5498 0.3321 0.072 Uiso 1 1 calc R . . C28A C 0.4359(2) 0.60643(19) 0.29644(13) 0.0531(9) Uani 1 1 d . . . H28A H 0.4865 0.5972 0.3271 0.064 Uiso 1 1 calc R . . C29A C 0.43851(18) 0.64886(16) 0.24941(12) 0.0357(7) Uani 1 1 d . . . C30A C 0.52303(17) 0.67807(16) 0.24692(12) 0.0405(7) Uani 1 1 d . . . H30A H 0.511 0.7185 0.2171 0.049 Uiso 1 1 calc R . . C31A C 0.5785(2) 0.71190(18) 0.30381(13) 0.0559(9) Uani 1 1 d . . . H31A H 0.6313 0.7299 0.2993 0.084 Uiso 1 1 calc R . . H31B H 0.5908 0.6736 0.334 0.084 Uiso 1 1 calc R . . H31C H 0.5487 0.7539 0.3145 0.084 Uiso 1 1 calc R . . C32A C 0.5704(2) 0.61565(18) 0.22736(16) 0.0563(9) Uani 1 1 d . . . H32A H 0.6242 0.635 0.2255 0.084 Uiso 1 1 calc R . . H32B H 0.5364 0.5979 0.1892 0.084 Uiso 1 1 calc R . . H32C H 0.5809 0.5741 0.2549 0.084 Uiso 1 1 calc R . . C33A C 0.20439(17) 0.63759(16) 0.15676(13) 0.0393(7) Uani 1 1 d . . . H33A H 0.2179 0.6597 0.1232 0.047 Uiso 1 1 calc R . . C34A C 0.1415(2) 0.6890(2) 0.17123(17) 0.0666(10) Uani 1 1 d . . . H34A H 0.1674 0.7382 0.1829 0.1 Uiso 1 1 calc R . . H34B H 0.1251 0.6673 0.2028 0.1 Uiso 1 1 calc R . . H34C H 0.0915 0.6948 0.1373 0.1 Uiso 1 1 calc R . . C35A C 0.1634(2) 0.56138(19) 0.13828(17) 0.0632(10) Uani 1 1 d . . . H35A H 0.1111 0.568 0.1061 0.095 Uiso 1 1 calc R . . H35B H 0.1507 0.538 0.1708 0.095 Uiso 1 1 calc R . . H35C H 0.2021 0.5293 0.1261 0.095 Uiso 1 1 calc R . . C36A C 0.34959(18) 0.53073(15) 0.08308(12) 0.0378(7) Uani 1 1 d . . . H36A H 0.2882 0.5207 0.0704 0.045 Uiso 1 1 calc R . . H36B H 0.3707 0.5143 0.0516 0.045 Uiso 1 1 calc R . . C37A C 0.39093(19) 0.48102(16) 0.13558(13) 0.0431(7) Uani 1 1 d . . . H37A H 0.3777 0.4284 0.1252 0.065 Uiso 1 1 calc R . . H37B H 0.3693 0.4947 0.167 0.065 Uiso 1 1 calc R . . H37C H 0.4521 0.4882 0.1481 0.065 Uiso 1 1 calc R . . Zn1B Zn 0.861754(18) 0.616298(17) 0.607492(13) 0.02846(10) Uani 1 1 d . . . N1B N 0.91531(12) 0.69212(11) 0.66562(8) 0.0252(5) Uani 1 1 d . . . N2B N 0.79643(12) 0.68446(12) 0.54713(9) 0.0270(5) Uani 1 1 d . . . C1B C 0.90284(15) 0.76561(14) 0.65686(10) 0.0260(6) Uani 1 1 d . . . C2B C 0.84922(15) 0.79327(14) 0.60409(11) 0.0275(6) Uani 1 1 d . . . H2B H 0.8464 0.8464 0.6026 0.033 Uiso 1 1 calc R . . C3B C 0.79885(15) 0.75888(14) 0.55299(11) 0.0269(6) Uani 1 1 d . . . C4B C 0.74867(16) 0.81586(15) 0.50632(11) 0.0307(6) Uani 1 1 d . . . C5B C 0.69372(17) 0.86447(16) 0.53240(13) 0.0404(7) Uani 1 1 d . . . H5D H 0.6534 0.8325 0.543 0.061 Uiso 1 1 calc R . . H5E H 0.6631 0.9017 0.504 0.061 Uiso 1 1 calc R . . H5F H 0.7298 0.8902 0.5668 0.061 Uiso 1 1 calc R . . C6B C 0.81186(17) 0.86640(15) 0.48974(13) 0.0382(7) Uani 1 1 d . . . H6D H 0.8515 0.8882 0.5246 0.057 Uiso 1 1 calc R . . H6E H 0.7813 0.9067 0.4644 0.057 Uiso 1 1 calc R . . H6F H 0.8429 0.8365 0.4696 0.057 Uiso 1 1 calc R . . C7B C 0.68924(18) 0.78434(16) 0.44932(12) 0.0429(7) Uani 1 1 d . . . H7D H 0.6475 0.7514 0.4574 0.064 Uiso 1 1 calc R . . H7E H 0.722 0.7557 0.4297 0.064 Uiso 1 1 calc R . . H7F H 0.6604 0.8258 0.4246 0.064 Uiso 1 1 calc R . . C8B C 0.94675(16) 0.82889(14) 0.70084(11) 0.0302(6) Uani 1 1 d . . . C9B C 0.87997(18) 0.87806(15) 0.71406(13) 0.0383(7) Uani 1 1 d . . . H9D H 0.8393 0.8954 0.6779 0.057 Uiso 1 1 calc R . . H9E H 0.9074 0.9214 0.737 0.057 Uiso 1 1 calc R . . H9F H 0.8506 0.8488 0.7357 0.057 Uiso 1 1 calc R . . C10B C 0.99824(17) 0.87777(15) 0.67208(13) 0.0378(7) Uani 1 1 d . . . H10D H 0.9615 0.8953 0.6345 0.057 Uiso 1 1 calc R . . H10E H 1.0444 0.848 0.6667 0.057 Uiso 1 1 calc R . . H10F H 1.0215 0.921 0.6967 0.057 Uiso 1 1 calc R . . C11B C 1.00779(19) 0.80367(15) 0.75926(12) 0.0415(7) Uani 1 1 d . . . H11D H 1.0518 0.7719 0.753 0.062 Uiso 1 1 calc R . . H11E H 0.9768 0.7753 0.7802 0.062 Uiso 1 1 calc R . . H11F H 1.0337 0.8478 0.7818 0.062 Uiso 1 1 calc R . . C12B C 0.95995(17) 0.65453(14) 0.71799(11) 0.0289(6) Uani 1 1 d . . . C13B C 0.91986(18) 0.64276(14) 0.75993(11) 0.0322(6) Uani 1 1 d . . . C14B C 0.9608(2) 0.59942(16) 0.80782(12) 0.0411(7) Uani 1 1 d . . . H14B H 0.935 0.5915 0.8368 0.049 Uiso 1 1 calc R . . C15B C 1.0382(2) 0.56777(16) 0.81386(13) 0.0467(8) Uani 1 1 d . . . H15B H 1.0657 0.5389 0.8472 0.056 Uiso 1 1 calc R . . C16B C 1.07611(19) 0.57754(15) 0.77209(13) 0.0420(7) Uani 1 1 d . . . H16B H 1.1292 0.5548 0.7768 0.05 Uiso 1 1 calc R . . C17B C 1.03783(16) 0.62034(14) 0.72275(11) 0.0310(6) Uani 1 1 d . . . C18B C 1.07963(17) 0.62798(15) 0.67633(13) 0.0397(7) Uani 1 1 d . . . H18B H 1.0353 0.6442 0.6402 0.048 Uiso 1 1 calc R . . C19B C 1.1163(2) 0.55461(18) 0.66335(17) 0.0632(10) Uani 1 1 d . . . H19D H 1.1416 0.5627 0.6329 0.095 Uiso 1 1 calc R . . H19E H 1.0713 0.5172 0.6506 0.095 Uiso 1 1 calc R . . H19F H 1.1595 0.5367 0.6982 0.095 Uiso 1 1 calc R . . C20B C 1.1476(2) 0.6875(2) 0.6912(2) 0.0772(12) Uani 1 1 d . . . H20D H 1.1727 0.691 0.6602 0.116 Uiso 1 1 calc R . . H20E H 1.1913 0.6742 0.7273 0.116 Uiso 1 1 calc R . . H20F H 1.1228 0.7359 0.6957 0.116 Uiso 1 1 calc R . . C21B C 0.83273(19) 0.67458(16) 0.75221(12) 0.0397(7) Uani 1 1 d . . . H21B H 0.8264 0.7209 0.7282 0.048 Uiso 1 1 calc R . . C22B C 0.7648(2) 0.61992(18) 0.71958(16) 0.0567(9) Uani 1 1 d . . . H22D H 0.7092 0.6415 0.7149 0.085 Uiso 1 1 calc R . . H22E H 0.771 0.5729 0.7412 0.085 Uiso 1 1 calc R . . H22F H 0.7703 0.6101 0.6816 0.085 Uiso 1 1 calc R . . C23B C 0.8193(3) 0.6967(2) 0.80877(15) 0.0728(11) Uani 1 1 d . . . H23D H 0.8633 0.732 0.8295 0.109 Uiso 1 1 calc R . . H23E H 0.8221 0.6519 0.8324 0.109 Uiso 1 1 calc R . . H23F H 0.7639 0.7203 0.8007 0.109 Uiso 1 1 calc R . . C24B C 0.75160(16) 0.64235(14) 0.49651(11) 0.0278(6) Uani 1 1 d . . . C25B C 0.67218(16) 0.61143(14) 0.49218(11) 0.0297(6) Uani 1 1 d . . . C26B C 0.63461(17) 0.56447(15) 0.44569(12) 0.0367(7) Uani 1 1 d . . . H26B H 0.5811 0.5431 0.4419 0.044 Uiso 1 1 calc R . . C27B C 0.67280(18) 0.54816(15) 0.40512(12) 0.0389(7) Uani 1 1 d . . . H27B H 0.6454 0.5167 0.3734 0.047 Uiso 1 1 calc R . . C28B C 0.75144(18) 0.57783(15) 0.41077(11) 0.0368(7) Uani 1 1 d . . . H28B H 0.778 0.5657 0.3829 0.044 Uiso 1 1 calc R . . C29B C 0.79204(16) 0.62457(15) 0.45591(11) 0.0309(6) Uani 1 1 d . . . C30B C 0.87993(17) 0.65475(17) 0.46233(12) 0.0403(7) Uani 1 1 d . . . H30B H 0.8918 0.6971 0.4905 0.048 Uiso 1 1 calc R . . C31B C 0.8879(2) 0.6841(2) 0.40579(14) 0.0618(10) Uani 1 1 d . . . H31D H 0.9452 0.7028 0.4123 0.093 Uiso 1 1 calc R . . H31E H 0.8475 0.725 0.3913 0.093 Uiso 1 1 calc R . . H31F H 0.8761 0.6435 0.3774 0.093 Uiso 1 1 calc R . . C32B C 0.94580(19) 0.5935(2) 0.48661(15) 0.0610(10) Uani 1 1 d . . . H32D H 1.0021 0.6132 0.4907 0.091 Uiso 1 1 calc R . . H32E H 0.934 0.5506 0.4603 0.091 Uiso 1 1 calc R . . H32F H 0.9435 0.5776 0.5244 0.091 Uiso 1 1 calc R . . C33B C 0.62962(16) 0.62568(15) 0.53746(13) 0.0347(7) Uani 1 1 d . . . H33B H 0.6649 0.6624 0.5658 0.042 Uiso 1 1 calc R . . C34B C 0.54160(19) 0.6596(2) 0.51166(16) 0.0584(9) Uani 1 1 d . . . H34D H 0.5166 0.6679 0.5423 0.088 Uiso 1 1 calc R . . H34E H 0.506 0.6252 0.4829 0.088 Uiso 1 1 calc R . . H34F H 0.5459 0.7075 0.4932 0.088 Uiso 1 1 calc R . . C35B C 0.6247(2) 0.55414(17) 0.57000(14) 0.0505(8) Uani 1 1 d . . . H35D H 0.5972 0.5648 0.599 0.076 Uiso 1 1 calc R . . H35E H 0.6817 0.5351 0.5891 0.076 Uiso 1 1 calc R . . H35F H 0.5921 0.5164 0.5429 0.076 Uiso 1 1 calc R . . C36B C 0.87353(18) 0.50710(15) 0.60825(12) 0.0384(7) Uani 1 1 d . . . H36C H 0.8296 0.487 0.574 0.046 Uiso 1 1 calc R . . H36D H 0.9288 0.4952 0.6037 0.046 Uiso 1 1 calc R . . C37B C 0.8674(2) 0.46509(16) 0.66101(13) 0.0478(8) Uani 1 1 d . . . H37D H 0.8742 0.4113 0.656 0.072 Uiso 1 1 calc R . . H37E H 0.8121 0.4744 0.6655 0.072 Uiso 1 1 calc R . . H37F H 0.9118 0.4826 0.6954 0.072 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 Zn1A 0.03485(19) 0.02313(18) 0.02904(18) 0.00063(13) 0.01182(14) -0.00085(13) N1A 0.0262(11) 0.0251(12) 0.0262(12) -0.0020(9) 0.0098(9) 0.0007(9) N2A 0.0287(12) 0.0252(13) 0.0275(12) 0.0038(9) 0.0098(10) -0.0004(10) C1A 0.0234(13) 0.0251(15) 0.0260(14) 0.0004(11) 0.0070(11) -0.0022(11) C2A 0.0289(14) 0.0217(14) 0.0297(15) -0.0004(11) 0.0090(12) -0.0025(11) C3A 0.0254(14) 0.0258(15) 0.0257(14) 0.0003(11) 0.0059(11) 0.0000(11) C4A 0.0412(16) 0.0290(15) 0.0253(14) -0.0026(12) 0.0111(12) 0.0005(13) C5A 0.0476(18) 0.0327(17) 0.0351(17) -0.0075(13) 0.0045(14) -0.0020(14) C6A 0.073(2) 0.0362(17) 0.0315(16) -0.0045(13) 0.0266(16) 0.0020(16) C7A 0.0432(17) 0.0374(17) 0.0348(16) -0.0024(13) 0.0138(14) 0.0082(14) C8A 0.0299(14) 0.0262(14) 0.0279(14) 0.0037(11) 0.0109(12) 0.0001(11) C9A 0.071(2) 0.0295(17) 0.0478(19) -0.0013(14) 0.0262(17) -0.0097(15) C10A 0.0512(19) 0.0377(18) 0.0421(18) 0.0132(14) 0.0101(15) 0.0005(14) C11A 0.0497(19) 0.0380(18) 0.063(2) 0.0115(15) 0.0310(17) 0.0006(15) C12A 0.0332(15) 0.0202(14) 0.0265(14) 0.0018(11) 0.0120(12) -0.0003(11) C13A 0.0374(15) 0.0246(14) 0.0269(14) 0.0017(11) 0.0120(12) 0.0010(12) C14A 0.0491(18) 0.0317(16) 0.0278(15) 0.0001(12) 0.0083(14) 0.0028(14) C15A 0.066(2) 0.0373(18) 0.0338(17) -0.0014(13) 0.0233(16) 0.0097(16) C16A 0.0479(18) 0.0359(17) 0.0382(17) 0.0017(13) 0.0227(15) 0.0104(14) C17A 0.0361(15) 0.0268(15) 0.0331(15) 0.0029(12) 0.0180(13) 0.0032(12) C18A 0.0280(15) 0.0378(17) 0.0432(17) 0.0007(13) 0.0146(13) 0.0022(13) C19A 0.0396(17) 0.0436(19) 0.0512(19) 0.0132(15) 0.0095(15) 0.0026(15) C20A 0.0374(17) 0.050(2) 0.073(2) 0.0124(17) 0.0241(17) 0.0034(15) C21A 0.0324(15) 0.0331(16) 0.0298(15) 0.0015(12) 0.0061(12) 0.0016(12) C22A 0.0368(17) 0.049(2) 0.0423(18) 0.0068(14) 0.0087(14) -0.0049(14) C23A 0.0430(17) 0.0390(18) 0.0358(17) 0.0018(13) 0.0027(14) 0.0004(14) C24A 0.0427(16) 0.0240(14) 0.0269(14) 0.0038(11) 0.0153(13) 0.0017(12) C25A 0.0429(16) 0.0301(16) 0.0367(16) 0.0026(12) 0.0212(14) -0.0013(13) C26A 0.057(2) 0.047(2) 0.056(2) 0.0134(16) 0.0315(18) -0.0005(16) C27A 0.075(3) 0.062(2) 0.050(2) 0.0276(18) 0.030(2) 0.0040(19) C28A 0.061(2) 0.060(2) 0.0355(18) 0.0174(16) 0.0108(16) 0.0033(18) C29A 0.0438(17) 0.0344(17) 0.0281(15) 0.0035(12) 0.0102(13) 0.0004(13) C30A 0.0406(17) 0.0382(18) 0.0363(17) 0.0038(13) 0.0033(14) -0.0027(14) C31A 0.058(2) 0.050(2) 0.0437(19) 0.0073(16) -0.0058(16) -0.0030(17) C32A 0.050(2) 0.054(2) 0.068(2) -0.0054(18) 0.0228(18) -0.0039(17) C33A 0.0363(16) 0.0389(18) 0.0472(18) 0.0019(14) 0.0196(14) -0.0041(13) C34A 0.051(2) 0.061(2) 0.083(3) -0.015(2) 0.015(2) 0.0095(18) C35A 0.050(2) 0.046(2) 0.087(3) -0.0122(19) 0.014(2) -0.0071(17) C36A 0.0476(18) 0.0253(16) 0.0416(17) 0.0027(13) 0.0156(14) -0.0030(13) C37A 0.060(2) 0.0267(16) 0.0452(18) 0.0044(13) 0.0206(16) 0.0030(14) Zn1B 0.03328(18) 0.02396(18) 0.02525(17) -0.00009(12) 0.00526(13) -0.00028(13) N1B 0.0293(11) 0.0227(12) 0.0225(11) 0.0030(9) 0.0068(9) -0.0003(9) N2B 0.0276(12) 0.0266(13) 0.0258(12) -0.0005(9) 0.0071(9) -0.0011(9) C1B 0.0284(14) 0.0234(15) 0.0267(14) -0.0012(11) 0.0095(12) -0.0015(11) C2B 0.0318(14) 0.0189(14) 0.0311(15) 0.0004(11) 0.0093(12) -0.0011(11) C3B 0.0271(14) 0.0259(15) 0.0286(14) 0.0041(11) 0.0102(12) 0.0016(11) C4B 0.0300(14) 0.0302(15) 0.0294(15) 0.0069(12) 0.0059(12) 0.0007(12) C5B 0.0346(16) 0.0422(18) 0.0427(18) 0.0094(14) 0.0099(14) 0.0081(14) C6B 0.0375(16) 0.0352(17) 0.0401(17) 0.0118(13) 0.0098(14) 0.0024(13) C7B 0.0434(17) 0.0366(17) 0.0378(17) 0.0096(13) -0.0025(14) 0.0014(14) C8B 0.0337(15) 0.0249(15) 0.0299(15) -0.0008(11) 0.0071(12) -0.0028(12) C9B 0.0455(17) 0.0332(17) 0.0392(17) -0.0042(13) 0.0176(14) -0.0026(13) C10B 0.0382(16) 0.0320(16) 0.0406(17) 0.0000(13) 0.0087(14) -0.0075(13) C11B 0.0541(18) 0.0278(16) 0.0325(16) -0.0068(12) -0.0005(14) -0.0061(14) C12B 0.0385(16) 0.0201(14) 0.0258(14) -0.0022(11) 0.0071(12) -0.0050(12) C13B 0.0447(17) 0.0209(14) 0.0290(15) -0.0030(11) 0.0090(13) -0.0031(12) C14B 0.063(2) 0.0295(16) 0.0266(16) -0.0023(12) 0.0089(14) -0.0069(15) C15B 0.068(2) 0.0283(17) 0.0278(16) 0.0027(13) -0.0068(16) -0.0056(16) C16B 0.0422(17) 0.0279(16) 0.0435(18) 0.0000(14) -0.0036(15) 0.0007(13) C17B 0.0313(15) 0.0227(14) 0.0317(15) -0.0037(11) -0.0003(12) -0.0034(12) C18B 0.0296(15) 0.0387(18) 0.0497(19) 0.0028(14) 0.0109(14) 0.0033(13) C19B 0.078(2) 0.043(2) 0.082(3) -0.0122(18) 0.044(2) -0.0028(18) C20B 0.070(2) 0.054(2) 0.129(4) -0.024(2) 0.061(3) -0.021(2) C21B 0.0573(19) 0.0310(16) 0.0383(17) 0.0014(13) 0.0256(15) 0.0018(14) C22B 0.047(2) 0.048(2) 0.079(3) -0.0083(18) 0.0263(19) -0.0014(16) C23B 0.107(3) 0.073(3) 0.057(2) -0.003(2) 0.054(2) 0.017(2) C24B 0.0277(14) 0.0236(14) 0.0272(14) 0.0025(11) 0.0017(11) 0.0027(11) C25B 0.0279(14) 0.0250(15) 0.0316(15) 0.0068(12) 0.0031(12) 0.0046(12) C26B 0.0303(15) 0.0303(16) 0.0405(17) 0.0042(13) -0.0014(13) -0.0033(12) C27B 0.0467(18) 0.0291(16) 0.0312(16) -0.0053(12) -0.0014(14) -0.0020(14) C28B 0.0456(18) 0.0359(17) 0.0250(15) -0.0005(12) 0.0057(13) 0.0054(14) C29B 0.0344(15) 0.0331(16) 0.0224(14) 0.0032(11) 0.0051(12) 0.0035(12) C30B 0.0405(17) 0.052(2) 0.0305(16) -0.0039(14) 0.0137(14) -0.0048(14) C31B 0.065(2) 0.082(3) 0.044(2) 0.0013(18) 0.0248(18) -0.017(2) C32B 0.0365(18) 0.092(3) 0.056(2) 0.005(2) 0.0161(16) 0.0069(18) C33B 0.0288(15) 0.0306(16) 0.0443(17) 0.0009(13) 0.0108(13) 0.0005(12) C34B 0.0424(19) 0.065(2) 0.073(2) 0.0188(19) 0.0250(18) 0.0131(17) C35B 0.061(2) 0.046(2) 0.052(2) 0.0089(16) 0.0285(17) 0.0068(16) C36B 0.0488(18) 0.0287(16) 0.0352(16) -0.0033(12) 0.0101(14) -0.0002(13) C37B 0.069(2) 0.0279(17) 0.0421(18) 0.0025(14) 0.0118(16) 0.0034(15) #----------------------------------------------------------------------------# # 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 Zn1A N1A 1.961(2) . ? Zn1A C36A 1.964(3) . ? Zn1A N2A 1.968(2) . ? N1A C1A 1.339(3) . ? N1A C12A 1.448(3) . ? N2A C3A 1.335(3) . ? N2A C24A 1.438(3) . ? C1A C2A 1.401(3) . ? C1A C8A 1.567(3) . ? C2A C3A 1.413(3) . ? C2A H2A 0.95 . ? C3A C4A 1.564(3) . ? C4A C6A 1.537(4) . ? C4A C5A 1.538(4) . ? C4A C7A 1.540(4) . ? C5A H5A 0.98 . ? C5A H5B 0.98 . ? C5A H5C 0.98 . ? C6A H6A 0.98 . ? C6A H6B 0.98 . ? C6A H6C 0.98 . ? C7A H7A 0.98 . ? C7A H7B 0.98 . ? C7A H7C 0.98 . ? C8A C11A 1.532(4) . ? C8A C9A 1.535(4) . ? C8A C10A 1.538(4) . ? C9A H9A 0.98 . ? C9A H9B 0.98 . ? C9A H9C 0.98 . ? C10A H10A 0.98 . ? C10A H10B 0.98 . ? C10A H10C 0.98 . ? C11A H11A 0.98 . ? C11A H11B 0.98 . ? C11A H11C 0.98 . ? C12A C13A 1.409(3) . ? C12A C17A 1.411(3) . ? C13A C14A 1.397(4) . ? C13A C21A 1.524(4) . ? C14A C15A 1.367(4) . ? C14A H14A 0.95 . ? C15A C16A 1.373(4) . ? C15A H15A 0.95 . ? C16A C17A 1.395(4) . ? C16A H16A 0.95 . ? C17A C18A 1.524(4) . ? C18A C20A 1.529(4) . ? C18A C19A 1.535(4) . ? C18A H18A 1 . ? C19A H19A 0.98 . ? C19A H19B 0.98 . ? C19A H19C 0.98 . ? C20A H20A 0.98 . ? C20A H20B 0.98 . ? C20A H20C 0.98 . ? C21A C22A 1.534(4) . ? C21A C23A 1.535(4) . ? C21A H21A 1 . ? C22A H22A 0.98 . ? C22A H22B 0.98 . ? C22A H22C 0.98 . ? C23A H23A 0.98 . ? C23A H23B 0.98 . ? C23A H23C 0.98 . ? C24A C29A 1.402(4) . ? C24A C25A 1.404(4) . ? C25A C26A 1.390(4) . ? C25A C33A 1.525(4) . ? C26A C27A 1.367(5) . ? C26A H26A 0.95 . ? C27A C28A 1.380(4) . ? C27A H27A 0.95 . ? C28A C29A 1.391(4) . ? C28A H28A 0.95 . ? C29A C30A 1.527(4) . ? C30A C32A 1.530(4) . ? C30A C31A 1.530(4) . ? C30A H30A 1 . ? C31A H31A 0.98 . ? C31A H31B 0.98 . ? C31A H31C 0.98 . ? C32A H32A 0.98 . ? C32A H32B 0.98 . ? C32A H32C 0.98 . ? C33A C34A 1.522(4) . ? C33A C35A 1.526(4) . ? C33A H33A 1 . ? C34A H34A 0.98 . ? C34A H34B 0.98 . ? C34A H34C 0.98 . ? C35A H35A 0.98 . ? C35A H35B 0.98 . ? C35A H35C 0.98 . ? C36A C37A 1.534(4) . ? C36A H36A 0.99 . ? C36A H36B 0.99 . ? C37A H37A 0.98 . ? C37A H37B 0.98 . ? C37A H37C 0.98 . ? Zn1B N2B 1.957(2) . ? Zn1B C36B 1.958(3) . ? Zn1B N1B 1.962(2) . ? N1B C1B 1.335(3) . ? N1B C12B 1.429(3) . ? N2B C3B 1.335(3) . ? N2B C24B 1.439(3) . ? C1B C2B 1.407(3) . ? C1B C8B 1.572(3) . ? C2B C3B 1.408(3) . ? C2B H2B 0.95 . ? C3B C4B 1.560(3) . ? C4B C7B 1.539(4) . ? C4B C6B 1.540(4) . ? C4B C5B 1.543(4) . ? C5B H5D 0.98 . ? C5B H5E 0.98 . ? C5B H5F 0.98 . ? C6B H6D 0.98 . ? C6B H6E 0.98 . ? C6B H6F 0.98 . ? C7B H7D 0.98 . ? C7B H7E 0.98 . ? C7B H7F 0.98 . ? C8B C9B 1.535(4) . ? C8B C11B 1.537(4) . ? C8B C10B 1.545(4) . ? C9B H9D 0.98 . ? C9B H9E 0.98 . ? C9B H9F 0.98 . ? C10B H10D 0.98 . ? C10B H10E 0.98 . ? C10B H10F 0.98 . ? C11B H11D 0.98 . ? C11B H11E 0.98 . ? C11B H11F 0.98 . ? C12B C17B 1.410(4) . ? C12B C13B 1.410(4) . ? C13B C14B 1.389(4) . ? C13B C21B 1.520(4) . ? C14B C15B 1.379(4) . ? C14B H14B 0.95 . ? C15B C16B 1.375(4) . ? C15B H15B 0.95 . ? C16B C17B 1.400(4) . ? C16B H16B 0.95 . ? C17B C18B 1.519(4) . ? C18B C20B 1.514(4) . ? C18B C19B 1.522(4) . ? C18B H18B 1 . ? C19B H19D 0.98 . ? C19B H19E 0.98 . ? C19B H19F 0.98 . ? C20B H20D 0.98 . ? C20B H20E 0.98 . ? C20B H20F 0.98 . ? C21B C22B 1.518(4) . ? C21B C23B 1.524(4) . ? C21B H21B 1 . ? C22B H22D 0.98 . ? C22B H22E 0.98 . ? C22B H22F 0.98 . ? C23B H23D 0.98 . ? C23B H23E 0.98 . ? C23B H23F 0.98 . ? C24B C29B 1.406(4) . ? C24B C25B 1.412(4) . ? C25B C26B 1.392(4) . ? C25B C33B 1.518(4) . ? C26B C27B 1.373(4) . ? C26B H26B 0.95 . ? C27B C28B 1.384(4) . ? C27B H27B 0.95 . ? C28B C29B 1.379(4) . ? C28B H28B 0.95 . ? C29B C30B 1.527(4) . ? C30B C31B 1.526(4) . ? C30B C32B 1.532(4) . ? C30B H30B 1 . ? C31B H31D 0.98 . ? C31B H31E 0.98 . ? C31B H31F 0.98 . ? C32B H32D 0.98 . ? C32B H32E 0.98 . ? C32B H32F 0.98 . ? C33B C35B 1.521(4) . ? C33B C34B 1.531(4) . ? C33B H33B 1 . ? C34B H34D 0.98 . ? C34B H34E 0.98 . ? C34B H34F 0.98 . ? C35B H35D 0.98 . ? C35B H35E 0.98 . ? C35B H35F 0.98 . ? C36B C37B 1.525(4) . ? C36B H36C 0.99 . ? C36B H36D 0.99 . ? C37B H37D 0.98 . ? C37B H37E 0.98 . ? C37B H37F 0.98 . ? 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 N1A Zn1A C36A 132.79(10) . . ? N1A Zn1A N2A 97.85(8) . . ? C36A Zn1A N2A 129.23(10) . . ? C1A N1A C12A 126.2(2) . . ? C1A N1A Zn1A 123.07(17) . . ? C12A N1A Zn1A 110.73(15) . . ? C3A N2A C24A 125.0(2) . . ? C3A N2A Zn1A 122.87(17) . . ? C24A N2A Zn1A 112.07(16) . . ? N1A C1A C2A 121.2(2) . . ? N1A C1A C8A 123.6(2) . . ? C2A C1A C8A 115.1(2) . . ? C1A C2A C3A 133.7(2) . . ? C1A C2A H2A 113.2 . . ? C3A C2A H2A 113.2 . . ? N2A C3A C2A 121.2(2) . . ? N2A C3A C4A 126.0(2) . . ? C2A C3A C4A 112.9(2) . . ? C6A C4A C5A 106.8(2) . . ? C6A C4A C7A 105.5(2) . . ? C5A C4A C7A 109.6(2) . . ? C6A C4A C3A 117.8(2) . . ? C5A C4A C3A 108.5(2) . . ? C7A C4A C3A 108.4(2) . . ? C4A C5A H5A 109.5 . . ? C4A C5A H5B 109.5 . . ? H5A C5A H5B 109.5 . . ? C4A C5A H5C 109.5 . . ? H5A C5A H5C 109.5 . . ? H5B C5A H5C 109.5 . . ? C4A C6A H6A 109.5 . . ? C4A C6A H6B 109.5 . . ? H6A C6A H6B 109.5 . . ? C4A C6A H6C 109.5 . . ? H6A C6A H6C 109.5 . . ? H6B C6A H6C 109.5 . . ? C4A C7A H7A 109.5 . . ? C4A C7A H7B 109.5 . . ? H7A C7A H7B 109.5 . . ? C4A C7A H7C 109.5 . . ? H7A C7A H7C 109.5 . . ? H7B C7A H7C 109.5 . . ? C11A C8A C9A 106.1(2) . . ? C11A C8A C10A 108.4(2) . . ? C9A C8A C10A 105.5(2) . . ? C11A C8A C1A 112.0(2) . . ? C9A C8A C1A 114.0(2) . . ? C10A C8A C1A 110.5(2) . . ? C8A C9A H9A 109.5 . . ? C8A C9A H9B 109.5 . . ? H9A C9A H9B 109.5 . . ? C8A C9A H9C 109.5 . . ? H9A C9A H9C 109.5 . . ? H9B C9A H9C 109.5 . . ? C8A C10A H10A 109.5 . . ? C8A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C8A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8A C11A H11A 109.5 . . ? C8A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C13A C12A C17A 120.4(2) . . ? C13A C12A N1A 119.6(2) . . ? C17A C12A N1A 119.2(2) . . ? C14A C13A C12A 118.0(2) . . ? C14A C13A C21A 120.2(2) . . ? C12A C13A C21A 121.7(2) . . ? C15A C14A C13A 121.7(3) . . ? C15A C14A H14A 119.2 . . ? C13A C14A H14A 119.2 . . ? C14A C15A C16A 120.1(3) . . ? C14A C15A H15A 120 . . ? C16A C15A H15A 120 . . ? C15A C16A C17A 121.2(3) . . ? C15A C16A H16A 119.4 . . ? C17A C16A H16A 119.4 . . ? C16A C17A C12A 118.3(3) . . ? C16A C17A C18A 119.5(2) . . ? C12A C17A C18A 122.1(2) . . ? C17A C18A C20A 113.4(2) . . ? C17A C18A C19A 109.1(2) . . ? C20A C18A C19A 109.3(2) . . ? C17A C18A H18A 108.3 . . ? C20A C18A H18A 108.3 . . ? C19A C18A H18A 108.3 . . ? C18A C19A H19A 109.5 . . ? C18A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C18A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C18A C20A H20A 109.5 . . ? C18A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C18A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C13A C21A C22A 108.6(2) . . ? C13A C21A C23A 114.1(2) . . ? C22A C21A C23A 109.9(2) . . ? C13A C21A H21A 108 . . ? C22A C21A H21A 108 . . ? C23A C21A H21A 108 . . ? C21A C22A H22A 109.5 . . ? C21A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C21A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C21A C23A H23A 109.5 . . ? C21A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C21A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C29A C24A C25A 121.3(2) . . ? C29A C24A N2A 119.3(2) . . ? C25A C24A N2A 119.1(2) . . ? C26A C25A C24A 117.8(3) . . ? C26A C25A C33A 119.5(3) . . ? C24A C25A C33A 122.8(2) . . ? C27A C26A C25A 121.5(3) . . ? C27A C26A H26A 119.2 . . ? C25A C26A H26A 119.2 . . ? C26A C27A C28A 120.2(3) . . ? C26A C27A H27A 119.9 . . ? C28A C27A H27A 119.9 . . ? C27A C28A C29A 120.9(3) . . ? C27A C28A H28A 119.5 . . ? C29A C28A H28A 119.5 . . ? C28A C29A C24A 118.0(3) . . ? C28A C29A C30A 119.6(3) . . ? C24A C29A C30A 122.4(2) . . ? C29A C30A C32A 110.1(2) . . ? C29A C30A C31A 113.5(3) . . ? C32A C30A C31A 110.4(3) . . ? C29A C30A H30A 107.6 . . ? C32A C30A H30A 107.6 . . ? C31A C30A H30A 107.6 . . ? C30A C31A H31A 109.5 . . ? C30A C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C30A C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C30A C32A H32A 109.5 . . ? C30A C32A H32B 109.5 . . ? H32A C32A H32B 109.5 . . ? C30A C32A H32C 109.5 . . ? H32A C32A H32C 109.5 . . ? H32B C32A H32C 109.5 . . ? C34A C33A C25A 112.5(3) . . ? C34A C33A C35A 109.2(3) . . ? C25A C33A C35A 111.3(2) . . ? C34A C33A H33A 107.9 . . ? C25A C33A H33A 107.9 . . ? C35A C33A H33A 107.9 . . ? C33A C34A H34A 109.5 . . ? C33A C34A H34B 109.5 . . ? H34A C34A H34B 109.5 . . ? C33A C34A H34C 109.5 . . ? H34A C34A H34C 109.5 . . ? H34B C34A H34C 109.5 . . ? C33A C35A H35A 109.5 . . ? C33A C35A H35B 109.5 . . ? H35A C35A H35B 109.5 . . ? C33A C35A H35C 109.5 . . ? H35A C35A H35C 109.5 . . ? H35B C35A H35C 109.5 . . ? C37A C36A Zn1A 118.4(2) . . ? C37A C36A H36A 107.7 . . ? Zn1A C36A H36A 107.7 . . ? C37A C36A H36B 107.7 . . ? Zn1A C36A H36B 107.7 . . ? H36A C36A H36B 107.1 . . ? C36A C37A H37A 109.5 . . ? C36A C37A H37B 109.5 . . ? H37A C37A H37B 109.5 . . ? C36A C37A H37C 109.5 . . ? H37A C37A H37C 109.5 . . ? H37B C37A H37C 109.5 . . ? N2B Zn1B C36B 131.00(10) . . ? N2B Zn1B N1B 97.78(9) . . ? C36B Zn1B N1B 131.17(10) . . ? C1B N1B C12B 128.0(2) . . ? C1B N1B Zn1B 123.33(16) . . ? C12B N1B Zn1B 108.34(15) . . ? C3B N2B C24B 127.0(2) . . ? C3B N2B Zn1B 123.14(17) . . ? C24B N2B Zn1B 109.78(15) . . ? N1B C1B C2B 120.9(2) . . ? N1B C1B C8B 125.5(2) . . ? C2B C1B C8B 113.5(2) . . ? C1B C2B C3B 133.6(2) . . ? C1B C2B H2B 113.2 . . ? C3B C2B H2B 113.2 . . ? N2B C3B C2B 121.2(2) . . ? N2B C3B C4B 125.4(2) . . ? C2B C3B C4B 113.4(2) . . ? C7B C4B C6B 105.9(2) . . ? C7B C4B C5B 106.4(2) . . ? C6B C4B C5B 109.3(2) . . ? C7B C4B C3B 117.9(2) . . ? C6B C4B C3B 108.7(2) . . ? C5B C4B C3B 108.4(2) . . ? C4B C5B H5D 109.5 . . ? C4B C5B H5E 109.5 . . ? H5D C5B H5E 109.5 . . ? C4B C5B H5F 109.5 . . ? H5D C5B H5F 109.5 . . ? H5E C5B H5F 109.5 . . ? C4B C6B H6D 109.5 . . ? C4B C6B H6E 109.5 . . ? H6D C6B H6E 109.5 . . ? C4B C6B H6F 109.5 . . ? H6D C6B H6F 109.5 . . ? H6E C6B H6F 109.5 . . ? C4B C7B H7D 109.5 . . ? C4B C7B H7E 109.5 . . ? H7D C7B H7E 109.5 . . ? C4B C7B H7F 109.5 . . ? H7D C7B H7F 109.5 . . ? H7E C7B H7F 109.5 . . ? C9B C8B C11B 106.5(2) . . ? C9B C8B C10B 108.8(2) . . ? C11B C8B C10B 106.7(2) . . ? C9B C8B C1B 110.0(2) . . ? C11B C8B C1B 117.0(2) . . ? C10B C8B C1B 107.5(2) . . ? C8B C9B H9D 109.5 . . ? C8B C9B H9E 109.5 . . ? H9D C9B H9E 109.5 . . ? C8B C9B H9F 109.5 . . ? H9D C9B H9F 109.5 . . ? H9E C9B H9F 109.5 . . ? C8B C10B H10D 109.5 . . ? C8B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C8B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C8B C11B H11D 109.5 . . ? C8B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C8B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C17B C12B C13B 121.2(2) . . ? C17B C12B N1B 118.9(2) . . ? C13B C12B N1B 119.3(2) . . ? C14B C13B C12B 118.5(3) . . ? C14B C13B C21B 120.5(3) . . ? C12B C13B C21B 121.0(2) . . ? C15B C14B C13B 120.8(3) . . ? C15B C14B H14B 119.6 . . ? C13B C14B H14B 119.6 . . ? C16B C15B C14B 120.6(3) . . ? C16B C15B H15B 119.7 . . ? C14B C15B H15B 119.7 . . ? C15B C16B C17B 121.2(3) . . ? C15B C16B H16B 119.4 . . ? C17B C16B H16B 119.4 . . ? C16B C17B C12B 117.7(3) . . ? C16B C17B C18B 120.1(3) . . ? C12B C17B C18B 122.3(2) . . ? C20B C18B C17B 111.9(3) . . ? C20B C18B C19B 109.4(3) . . ? C17B C18B C19B 113.1(2) . . ? C20B C18B H18B 107.4 . . ? C17B C18B H18B 107.4 . . ? C19B C18B H18B 107.4 . . ? C18B C19B H19D 109.5 . . ? C18B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C18B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C18B C20B H20D 109.5 . . ? C18B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C18B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C22B C21B C13B 110.7(2) . . ? C22B C21B C23B 110.0(3) . . ? C13B C21B C23B 113.4(3) . . ? C22B C21B H21B 107.5 . . ? C13B C21B H21B 107.5 . . ? C23B C21B H21B 107.5 . . ? C21B C22B H22D 109.5 . . ? C21B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C21B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C21B C23B H23D 109.5 . . ? C21B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C21B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C29B C24B C25B 120.8(2) . . ? C29B C24B N2B 119.4(2) . . ? C25B C24B N2B 119.3(2) . . ? C26B C25B C24B 117.8(2) . . ? C26B C25B C33B 120.2(2) . . ? C24B C25B C33B 122.0(2) . . ? C27B C26B C25B 121.7(3) . . ? C27B C26B H26B 119.1 . . ? C25B C26B H26B 119.1 . . ? C26B C27B C28B 119.6(3) . . ? C26B C27B H27B 120.2 . . ? C28B C27B H27B 120.2 . . ? C29B C28B C27B 121.4(3) . . ? C29B C28B H28B 119.3 . . ? C27B C28B H28B 119.3 . . ? C28B C29B C24B 118.6(2) . . ? C28B C29B C30B 120.6(2) . . ? C24B C29B C30B 120.9(2) . . ? C31B C30B C29B 112.8(2) . . ? C31B C30B C32B 109.7(3) . . ? C29B C30B C32B 109.8(3) . . ? C31B C30B H30B 108.1 . . ? C29B C30B H30B 108.1 . . ? C32B C30B H30B 108.1 . . ? C30B C31B H31D 109.5 . . ? C30B C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C30B C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C30B C32B H32D 109.5 . . ? C30B C32B H32E 109.5 . . ? H32D C32B H32E 109.5 . . ? C30B C32B H32F 109.5 . . ? H32D C32B H32F 109.5 . . ? H32E C32B H32F 109.5 . . ? C25B C33B C35B 111.0(2) . . ? C25B C33B C34B 112.3(2) . . ? C35B C33B C34B 110.0(2) . . ? C25B C33B H33B 107.8 . . ? C35B C33B H33B 107.8 . . ? C34B C33B H33B 107.8 . . ? C33B C34B H34D 109.5 . . ? C33B C34B H34E 109.5 . . ? H34D C34B H34E 109.5 . . ? C33B C34B H34F 109.5 . . ? H34D C34B H34F 109.5 . . ? H34E C34B H34F 109.5 . . ? C33B C35B H35D 109.5 . . ? C33B C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? C33B C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? C37B C36B Zn1B 117.61(19) . . ? C37B C36B H36C 107.9 . . ? Zn1B C36B H36C 107.9 . . ? C37B C36B H36D 107.9 . . ? Zn1B C36B H36D 107.9 . . ? H36C C36B H36D 107.2 . . ? C36B C37B H37D 109.5 . . ? C36B C37B H37E 109.5 . . ? H37D C37B H37E 109.5 . . ? C36B C37B H37F 109.5 . . ? H37D C37B H37F 109.5 . . ? H37E C37B H37F 109.5 . . ? 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 C36A Zn1A N1A C1A 175.24(19) . . . . ? N2A Zn1A N1A C1A -0.6(2) . . . . ? C36A Zn1A N1A C12A -4.3(2) . . . . ? N2A Zn1A N1A C12A 179.84(16) . . . . ? N1A Zn1A N2A C3A 3.6(2) . . . . ? C36A Zn1A N2A C3A -172.46(19) . . . . ? N1A Zn1A N2A C24A -173.78(17) . . . . ? C36A Zn1A N2A C24A 10.2(2) . . . . ? C12A N1A C1A C2A 177.7(2) . . . . ? Zn1A N1A C1A C2A -1.8(3) . . . . ? C12A N1A C1A C8A -1.3(4) . . . . ? Zn1A N1A C1A C8A 179.20(17) . . . . ? N1A C1A C2A C3A 2.2(4) . . . . ? C8A C1A C2A C3A -178.7(3) . . . . ? C24A N2A C3A C2A 172.9(2) . . . . ? Zn1A N2A C3A C2A -4.1(3) . . . . ? C24A N2A C3A C4A -6.2(4) . . . . ? Zn1A N2A C3A C4A 176.81(18) . . . . ? C1A C2A C3A N2A 1.1(4) . . . . ? C1A C2A C3A C4A -179.7(3) . . . . ? N2A C3A C4A C6A -7.3(4) . . . . ? C2A C3A C4A C6A 173.6(2) . . . . ? N2A C3A C4A C5A 114.1(3) . . . . ? C2A C3A C4A C5A -65.0(3) . . . . ? N2A C3A C4A C7A -126.9(3) . . . . ? C2A C3A C4A C7A 54.0(3) . . . . ? N1A C1A C8A C11A -54.5(3) . . . . ? C2A C1A C8A C11A 126.5(2) . . . . ? N1A C1A C8A C9A -174.9(2) . . . . ? C2A C1A C8A C9A 6.1(3) . . . . ? N1A C1A C8A C10A 66.5(3) . . . . ? C2A C1A C8A C10A -112.6(3) . . . . ? C1A N1A C12A C13A -91.6(3) . . . . ? Zn1A N1A C12A C13A 88.0(2) . . . . ? C1A N1A C12A C17A 98.4(3) . . . . ? Zn1A N1A C12A C17A -82.0(2) . . . . ? C17A C12A C13A C14A -4.8(4) . . . . ? N1A C12A C13A C14A -174.7(2) . . . . ? C17A C12A C13A C21A 171.0(2) . . . . ? N1A C12A C13A C21A 1.1(4) . . . . ? C12A C13A C14A C15A 1.4(4) . . . . ? C21A C13A C14A C15A -174.5(3) . . . . ? C13A C14A C15A C16A 1.5(4) . . . . ? C14A C15A C16A C17A -0.9(4) . . . . ? C15A C16A C17A C12A -2.5(4) . . . . ? C15A C16A C17A C18A 174.5(3) . . . . ? C13A C12A C17A C16A 5.4(4) . . . . ? N1A C12A C17A C16A 175.3(2) . . . . ? C13A C12A C17A C18A -171.5(2) . . . . ? N1A C12A C17A C18A -1.6(4) . . . . ? C16A C17A C18A C20A 48.9(3) . . . . ? C12A C17A C18A C20A -134.2(3) . . . . ? C16A C17A C18A C19A -73.1(3) . . . . ? C12A C17A C18A C19A 103.8(3) . . . . ? C14A C13A C21A C22A 78.2(3) . . . . ? C12A C13A C21A C22A -97.6(3) . . . . ? C14A C13A C21A C23A -44.8(3) . . . . ? C12A C13A C21A C23A 139.4(3) . . . . ? C3A N2A C24A C29A -81.5(3) . . . . ? Zn1A N2A C24A C29A 95.8(2) . . . . ? C3A N2A C24A C25A 104.6(3) . . . . ? Zn1A N2A C24A C25A -78.1(3) . . . . ? C29A C24A C25A C26A 5.7(4) . . . . ? N2A C24A C25A C26A 179.4(2) . . . . ? C29A C24A C25A C33A -173.9(3) . . . . ? N2A C24A C25A C33A -0.2(4) . . . . ? C24A C25A C26A C27A -2.9(5) . . . . ? C33A C25A C26A C27A 176.7(3) . . . . ? C25A C26A C27A C28A -0.7(5) . . . . ? C26A C27A C28A C29A 1.5(5) . . . . ? C27A C28A C29A C24A 1.2(5) . . . . ? C27A C28A C29A C30A -178.3(3) . . . . ? C25A C24A C29A C28A -4.8(4) . . . . ? N2A C24A C29A C28A -178.6(3) . . . . ? C25A C24A C29A C30A 174.6(3) . . . . ? N2A C24A C29A C30A 0.9(4) . . . . ? C28A C29A C30A C32A 79.4(4) . . . . ? C24A C29A C30A C32A -100.1(3) . . . . ? C28A C29A C30A C31A -44.8(4) . . . . ? C24A C29A C30A C31A 135.7(3) . . . . ? C26A C25A C33A C34A 72.2(4) . . . . ? C24A C25A C33A C34A -108.2(3) . . . . ? C26A C25A C33A C35A -50.7(4) . . . . ? C24A C25A C33A C35A 128.8(3) . . . . ? N1A Zn1A C36A C37A 143.83(19) . . . . ? N2A Zn1A C36A C37A -41.5(3) . . . . ? N2B Zn1B N1B C1B -1.0(2) . . . . ? C36B Zn1B N1B C1B 176.74(19) . . . . ? N2B Zn1B N1B C12B 173.01(16) . . . . ? C36B Zn1B N1B C12B -9.3(2) . . . . ? C36B Zn1B N2B C3B -176.56(19) . . . . ? N1B Zn1B N2B C3B 1.1(2) . . . . ? C36B Zn1B N2B C24B 0.1(2) . . . . ? N1B Zn1B N2B C24B 177.77(16) . . . . ? C12B N1B C1B C2B -172.7(2) . . . . ? Zn1B N1B C1B C2B 0.0(3) . . . . ? C12B N1B C1B C8B 9.9(4) . . . . ? Zn1B N1B C1B C8B -177.40(17) . . . . ? N1B C1B C2B C3B 1.4(4) . . . . ? C8B C1B C2B C3B 179.1(3) . . . . ? C24B N2B C3B C2B -176.4(2) . . . . ? Zn1B N2B C3B C2B -0.4(3) . . . . ? C24B N2B C3B C4B 3.6(4) . . . . ? Zn1B N2B C3B C4B 179.64(18) . . . . ? C1B C2B C3B N2B -1.2(4) . . . . ? C1B C2B C3B C4B 178.8(3) . . . . ? N2B C3B C4B C7B 1.9(4) . . . . ? C2B C3B C4B C7B -178.1(2) . . . . ? N2B C3B C4B C6B -118.5(3) . . . . ? C2B C3B C4B C6B 61.5(3) . . . . ? N2B C3B C4B C5B 122.8(3) . . . . ? C2B C3B C4B C5B -57.2(3) . . . . ? N1B C1B C8B C9B -123.0(3) . . . . ? C2B C1B C8B C9B 59.4(3) . . . . ? N1B C1B C8B C11B -1.3(4) . . . . ? C2B C1B C8B C11B -178.9(2) . . . . ? N1B C1B C8B C10B 118.6(3) . . . . ? C2B C1B C8B C10B -58.9(3) . . . . ? C1B N1B C12B C17B -109.9(3) . . . . ? Zn1B N1B C12B C17B 76.5(2) . . . . ? C1B N1B C12B C13B 79.6(3) . . . . ? Zn1B N1B C12B C13B -94.0(2) . . . . ? C17B C12B C13B C14B 3.1(4) . . . . ? N1B C12B C13B C14B 173.4(2) . . . . ? C17B C12B C13B C21B -175.0(2) . . . . ? N1B C12B C13B C21B -4.7(4) . . . . ? C12B C13B C14B C15B -0.9(4) . . . . ? C21B C13B C14B C15B 177.2(3) . . . . ? C13B C14B C15B C16B -1.0(4) . . . . ? C14B C15B C16B C17B 0.7(4) . . . . ? C15B C16B C17B C12B 1.4(4) . . . . ? C15B C16B C17B C18B -177.9(3) . . . . ? C13B C12B C17B C16B -3.3(4) . . . . ? N1B C12B C17B C16B -173.7(2) . . . . ? C13B C12B C17B C18B 176.0(2) . . . . ? N1B C12B C17B C18B 5.6(4) . . . . ? C16B C17B C18B C20B -81.8(3) . . . . ? C12B C17B C18B C20B 98.9(3) . . . . ? C16B C17B C18B C19B 42.2(4) . . . . ? C12B C17B C18B C19B -137.1(3) . . . . ? C14B C13B C21B C22B -89.4(3) . . . . ? C12B C13B C21B C22B 88.7(3) . . . . ? C14B C13B C21B C23B 34.8(4) . . . . ? C12B C13B C21B C23B -147.2(3) . . . . ? C3B N2B C24B C29B 90.0(3) . . . . ? Zn1B N2B C24B C29B -86.4(2) . . . . ? C3B N2B C24B C25B -98.1(3) . . . . ? Zn1B N2B C24B C25B 85.4(2) . . . . ? C29B C24B C25B C26B -1.6(4) . . . . ? N2B C24B C25B C26B -173.3(2) . . . . ? C29B C24B C25B C33B 176.0(2) . . . . ? N2B C24B C25B C33B 4.3(4) . . . . ? C24B C25B C26B C27B 0.1(4) . . . . ? C33B C25B C26B C27B -177.6(2) . . . . ? C25B C26B C27B C28B 1.2(4) . . . . ? C26B C27B C28B C29B -1.0(4) . . . . ? C27B C28B C29B C24B -0.4(4) . . . . ? C27B C28B C29B C30B 178.1(3) . . . . ? C25B C24B C29B C28B 1.8(4) . . . . ? N2B C24B C29B C28B 173.5(2) . . . . ? C25B C24B C29B C30B -176.8(2) . . . . ? N2B C24B C29B C30B -5.1(4) . . . . ? C28B C29B C30B C31B 45.8(4) . . . . ? C24B C29B C30B C31B -135.7(3) . . . . ? C28B C29B C30B C32B -76.9(3) . . . . ? C24B C29B C30B C32B 101.6(3) . . . . ? C26B C25B C33B C35B 64.8(3) . . . . ? C24B C25B C33B C35B -112.7(3) . . . . ? C26B C25B C33B C34B -58.8(3) . . . . ? C24B C25B C33B C34B 123.7(3) . . . . ? N2B Zn1B C36B C37B -134.5(2) . . . . ? N1B Zn1B C36B C37B 48.5(3) . . . . ? #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-25 at 17:21:19 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1446 _database_code_depnum_ccdc_archive 'CCDC 735243' _audit_creation_date 2008-02-25T17:21:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common (BDI)ZnCl _chemical_formula_moiety 'C35 H53 Cl1 N2 Zn1' _chemical_formula_sum 'C35 H53 Cl N2 Zn' _chemical_formula_weight 602.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.8648(1) _cell_length_b 9.2141(1) _cell_length_c 22.8397(2) _cell_angle_alpha 90 _cell_angle_beta 106.180(1) _cell_angle_gamma 90 _cell_volume 3408.57(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4123 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 4.5, which means that 90% of the reflections were measured at least 4.5 times. Phi and omega scans with a frame width of one degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. The Zn complex contains a crystallographic two-fold axis. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.906 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.497124E-1 _diffrn_orient_matrix_ub_12 -0.36195E-1 _diffrn_orient_matrix_ub_13 -0.55219E-2 _diffrn_orient_matrix_ub_21 -0.189911E-1 _diffrn_orient_matrix_ub_22 -0.98513E-2 _diffrn_orient_matrix_ub_23 -0.1064 _diffrn_orient_matrix_ub_31 0.350374E-1 _diffrn_orient_matrix_ub_32 0.277997E-1 _diffrn_orient_matrix_ub_33 -0.88277E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 32613 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3906 _reflns_number_gt 3273 _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 'SHELXS-97 (Sheldrick, 199)' _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 ;The methyl group hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The other hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded carbon atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+3.6521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3906 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.082 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.549 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Zn Zn 0 0.17395(3) 0.25 0.02731(9) Uani 1 2 d S . . Cl Cl 0 -0.05723(7) 0.25 0.0544(2) Uani 1 2 d S . . N1 N 0.05226(8) 0.30181(14) 0.31516(5) 0.0207(3) Uani 1 1 d . . . C1 C 0.04488(9) 0.44488(16) 0.30656(6) 0.0190(3) Uani 1 1 d . . . C2 C 0 0.5037(2) 0.25 0.0186(4) Uani 1 2 d S . . H2 H 0 0.6068 0.25 0.022 Uiso 1 2 calc SR . . C8 C 0.08458(9) 0.56179(16) 0.35532(7) 0.0219(3) Uani 1 1 d . . . C9 C 0.01604(11) 0.66020(18) 0.36618(7) 0.0289(4) Uani 1 1 d . . . H9A H -0.0176 0.6982 0.3271 0.043 Uiso 1 1 calc R . . H9B H 0.0411 0.7411 0.3928 0.043 Uiso 1 1 calc R . . H9C H -0.0189 0.6038 0.3856 0.043 Uiso 1 1 calc R . . C10 C 0.14469(11) 0.65309(19) 0.33030(8) 0.0321(4) Uani 1 1 d . . . H10A H 0.1156 0.6905 0.2898 0.048 Uiso 1 1 calc R . . H10B H 0.191 0.5922 0.3273 0.048 Uiso 1 1 calc R . . H10C H 0.1655 0.7345 0.3579 0.048 Uiso 1 1 calc R . . C11 C 0.13445(11) 0.50698(19) 0.41853(7) 0.0297(4) Uani 1 1 d . . . H11A H 0.179 0.4435 0.4141 0.045 Uiso 1 1 calc R . . H11B H 0.098 0.4526 0.4373 0.045 Uiso 1 1 calc R . . H11C H 0.1581 0.5899 0.4444 0.045 Uiso 1 1 calc R . . C12 C 0.09047(9) 0.22390(17) 0.37047(7) 0.0217(3) Uani 1 1 d . . . C13 C 0.16867(10) 0.16193(18) 0.37835(8) 0.0277(3) Uani 1 1 d . . . C14 C 0.20123(11) 0.0770(2) 0.43016(9) 0.0371(4) Uani 1 1 d . . . H14 H 0.2544 0.0351 0.4366 0.045 Uiso 1 1 calc R . . C15 C 0.15757(12) 0.0530(2) 0.47210(8) 0.0401(5) Uani 1 1 d . . . H15 H 0.1811 -0.0036 0.5074 0.048 Uiso 1 1 calc R . . C16 C 0.07963(11) 0.1113(2) 0.46263(8) 0.0343(4) Uani 1 1 d . . . H16 H 0.0496 0.093 0.4914 0.041 Uiso 1 1 calc R . . C17 C 0.04421(10) 0.19618(17) 0.41188(7) 0.0251(3) Uani 1 1 d . . . C18 C -0.04342(10) 0.2533(2) 0.40035(8) 0.0302(4) Uani 1 1 d . . . H18 H -0.05 0.3374 0.3717 0.036 Uiso 1 1 calc R . . C19 C -0.10527(12) 0.1368(3) 0.36949(10) 0.0496(5) Uani 1 1 d . . . H19A H -0.1615 0.1747 0.3622 0.074 Uiso 1 1 calc R . . H19B H -0.0984 0.0513 0.3959 0.074 Uiso 1 1 calc R . . H19C H -0.0956 0.1097 0.3306 0.074 Uiso 1 1 calc R . . C20 C -0.06338(13) 0.3064(2) 0.45807(9) 0.0445(5) Uani 1 1 d . . . H20A H -0.1205 0.3415 0.4476 0.067 Uiso 1 1 calc R . . H20B H -0.0258 0.3855 0.4763 0.067 Uiso 1 1 calc R . . H20C H -0.0567 0.2262 0.4872 0.067 Uiso 1 1 calc R . . C21 C 0.21806(11) 0.1823(2) 0.33255(9) 0.0355(4) Uani 1 1 d . . . H21 H 0.183 0.2387 0.2974 0.043 Uiso 1 1 calc R . . C22 C 0.23937(16) 0.0381(3) 0.30759(11) 0.0553(6) Uani 1 1 d . . . H22A H 0.2708 0.0566 0.2782 0.083 Uiso 1 1 calc R . . H22B H 0.1884 -0.0138 0.2874 0.083 Uiso 1 1 calc R . . H22C H 0.2726 -0.021 0.3412 0.083 Uiso 1 1 calc R . . C23 C 0.29626(14) 0.2701(3) 0.35964(13) 0.0597(7) Uani 1 1 d . . . H23A H 0.3266 0.2817 0.3291 0.09 Uiso 1 1 calc R . . H23B H 0.331 0.2193 0.3953 0.09 Uiso 1 1 calc R . . H23C H 0.2814 0.3659 0.372 0.09 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 Zn 0.04027(17) 0.01661(14) 0.02081(14) 0 0.00149(11) 0 Cl 0.0900(6) 0.0152(3) 0.0472(4) 0 0.0012(4) 0 N1 0.0244(6) 0.0199(7) 0.0164(6) 0.0006(5) 0.0033(5) -0.0001(5) C1 0.0188(7) 0.0199(8) 0.0185(7) -0.0012(6) 0.0055(5) -0.0015(6) C2 0.0231(10) 0.0143(10) 0.0174(9) 0 0.0039(8) 0 C8 0.0243(8) 0.0196(8) 0.0205(7) -0.0028(6) 0.0038(6) -0.0017(6) C9 0.0345(9) 0.0268(9) 0.0246(8) -0.0050(7) 0.0069(7) 0.0045(7) C10 0.0311(9) 0.0324(10) 0.0315(9) -0.0044(7) 0.0066(7) -0.0113(7) C11 0.0336(9) 0.0268(9) 0.0232(8) -0.0048(7) -0.0010(7) -0.0014(7) C12 0.0244(8) 0.0184(7) 0.0196(7) 0.0009(6) 0.0017(6) -0.0017(6) C13 0.0255(8) 0.0264(9) 0.0298(8) 0.0044(7) 0.0051(6) 0.0009(7) C14 0.0276(9) 0.0399(11) 0.0397(10) 0.0114(8) 0.0025(7) 0.0070(8) C15 0.0374(10) 0.0451(12) 0.0311(9) 0.0176(8) -0.0013(8) 0.0019(9) C16 0.0343(9) 0.0413(10) 0.0251(8) 0.0099(8) 0.0046(7) -0.0047(8) C17 0.0265(8) 0.0256(9) 0.0214(7) 0.0010(6) 0.0037(6) -0.0036(7) C18 0.0284(9) 0.0334(10) 0.0296(9) 0.0040(7) 0.0094(7) -0.0004(7) C19 0.0296(10) 0.0660(15) 0.0508(12) -0.0123(11) 0.0072(9) -0.0091(10) C20 0.0469(11) 0.0492(12) 0.0432(11) -0.0051(9) 0.0222(9) 0.0005(10) C21 0.0300(9) 0.0369(10) 0.0425(10) 0.0107(8) 0.0149(8) 0.0072(8) C22 0.0676(15) 0.0488(13) 0.0590(14) -0.0079(11) 0.0335(12) -0.0028(11) C23 0.0460(13) 0.0524(14) 0.0929(19) -0.0134(13) 0.0397(13) -0.0103(11) #----------------------------------------------------------------------------# # 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 Zn N1 1.9102(12) . ? Zn N1 1.9102(12) 2 ? Zn Cl 2.1301(7) . ? N1 C1 1.3335(19) . ? N1 C12 1.4397(18) . ? C1 C2 1.4106(16) . ? C1 C8 1.560(2) . ? C2 C1 1.4106(16) 2 ? C2 H2 0.95 . ? C8 C11 1.539(2) . ? C8 C9 1.543(2) . ? C8 C10 1.544(2) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 C13 1.402(2) . ? C12 C17 1.407(2) . ? C13 C14 1.397(2) . ? C13 C21 1.520(2) . ? C14 C15 1.379(3) . ? C14 H14 0.95 . ? C15 C16 1.380(3) . ? C15 H15 0.95 . ? C16 C17 1.388(2) . ? C16 H16 0.95 . ? C17 C18 1.521(2) . ? C18 C19 1.525(3) . ? C18 C20 1.529(2) . ? C18 H18 1 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C23 1.524(3) . ? C21 C22 1.527(3) . ? C21 H21 1 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? 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 N1 Zn N1 103.84(8) . 2 ? N1 Zn Cl 128.08(4) . . ? N1 Zn Cl 128.08(4) 2 . ? C1 N1 C12 128.52(13) . . ? C1 N1 Zn 119.41(10) . . ? C12 N1 Zn 111.88(9) . . ? N1 C1 C2 121.25(14) . . ? N1 C1 C8 125.00(13) . . ? C2 C1 C8 113.75(13) . . ? C1 C2 C1 134.84(19) 2 . ? C1 C2 H2 112.6 2 . ? C1 C2 H2 112.6 . . ? C11 C8 C9 106.26(13) . . ? C11 C8 C10 106.40(13) . . ? C9 C8 C10 109.75(13) . . ? C11 C8 C1 117.17(13) . . ? C9 C8 C1 109.20(12) . . ? C10 C8 C1 107.91(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 121.18(14) . . ? C13 C12 N1 119.38(13) . . ? C17 C12 N1 118.95(14) . . ? C14 C13 C12 118.06(15) . . ? C14 C13 C21 119.39(15) . . ? C12 C13 C21 122.54(14) . . ? C15 C14 C13 121.22(16) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 119.88(16) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 121.32(16) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C12 118.26(15) . . ? C16 C17 C18 120.72(15) . . ? C12 C17 C18 120.98(14) . . ? C17 C18 C19 110.04(15) . . ? C17 C18 C20 113.47(15) . . ? C19 C18 C20 109.70(15) . . ? C17 C18 H18 107.8 . . ? C19 C18 H18 107.8 . . ? C20 C18 H18 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 C23 111.36(17) . . ? C13 C21 C22 112.38(16) . . ? C23 C21 C22 110.28(17) . . ? C13 C21 H21 107.5 . . ? C23 C21 H21 107.5 . . ? C22 C21 H21 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 N1 Zn N1 C1 0.38(9) 2 . . . ? Cl Zn N1 C1 -179.62(9) . . . . ? N1 Zn N1 C12 175.76(12) 2 . . . ? Cl Zn N1 C12 -4.24(12) . . . . ? C12 N1 C1 C2 -175.27(12) . . . . ? Zn N1 C1 C2 -0.76(18) . . . . ? C12 N1 C1 C8 6.0(2) . . . . ? Zn N1 C1 C8 -179.53(10) . . . . ? N1 C1 C2 C1 0.45(11) . . . 2 ? C8 C1 C2 C1 179.35(12) . . . 2 ? N1 C1 C8 C11 -1.4(2) . . . . ? C2 C1 C8 C11 179.76(12) . . . . ? N1 C1 C8 C9 -122.19(16) . . . . ? C2 C1 C8 C9 58.96(15) . . . . ? N1 C1 C8 C10 118.57(16) . . . . ? C2 C1 C8 C10 -60.28(15) . . . . ? C1 N1 C12 C13 -103.73(19) . . . . ? Zn N1 C12 C13 81.42(15) . . . . ? C1 N1 C12 C17 84.2(2) . . . . ? Zn N1 C12 C17 -90.67(15) . . . . ? C17 C12 C13 C14 -2.9(2) . . . . ? N1 C12 C13 C14 -174.85(15) . . . . ? C17 C12 C13 C21 176.26(16) . . . . ? N1 C12 C13 C21 4.4(2) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C21 C13 C14 C15 -178.44(18) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C12 -1.1(3) . . . . ? C15 C16 C17 C18 176.84(17) . . . . ? C13 C12 C17 C16 3.1(2) . . . . ? N1 C12 C17 C16 175.06(15) . . . . ? C13 C12 C17 C18 -174.86(15) . . . . ? N1 C12 C17 C18 -2.9(2) . . . . ? C16 C17 C18 C19 -82.5(2) . . . . ? C12 C17 C18 C19 95.45(19) . . . . ? C16 C17 C18 C20 40.9(2) . . . . ? C12 C17 C18 C20 -141.22(17) . . . . ? C14 C13 C21 C23 -67.0(2) . . . . ? C12 C13 C21 C23 113.8(2) . . . . ? C14 C13 C21 C22 57.3(2) . . . . ? C12 C13 C21 C22 -121.93(19) . . . . ? #END OF CIF