# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_DACBr2 _database_code_depnum_ccdc_archive 'CCDC 882670' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DACBr2 _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Br2 N2 O2; CHCl3' _chemical_formula_sum 'C25 H29 Br2 Cl3 N2 O2' _chemical_formula_weight 655.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 8.6872(8) _cell_length_b 24.892(2) _cell_length_c 12.6503(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.440(2) _cell_angle_gamma 90.00 _cell_volume 2733.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 3.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.617 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37485 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4800 _reflns_number_gt 4200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+7.1133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4800 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.79032(4) 0.198278(14) 0.13988(3) 0.02360(11) Uani 1 1 d . . . Cl1 Cl 0.84283(17) 0.00143(7) 0.09421(15) 0.0789(5) Uani 1 1 d . . . N1 N 0.6770(3) 0.32749(11) -0.2272(2) 0.0183(6) Uani 1 1 d . . . O1 O 0.6138(3) 0.40048(10) -0.3290(2) 0.0320(6) Uani 1 1 d . . . C1 C 0.6902(4) 0.27442(14) -0.2200(3) 0.0172(7) Uani 1 1 d . . . Br2 Br 0.72236(4) 0.244147(13) -0.08423(3) 0.02033(10) Uani 1 1 d . . . Cl2 Cl 0.54347(15) 0.03795(5) 0.14845(10) 0.0529(3) Uani 1 1 d . . . O2 O 0.6292(3) 0.23073(10) -0.4803(2) 0.0289(6) Uani 1 1 d . . . N2 N 0.6812(3) 0.24205(11) -0.3040(2) 0.0176(6) Uani 1 1 d . . . C2 C 0.6473(4) 0.35440(14) -0.3292(3) 0.0217(8) Uani 1 1 d . . . Cl3 Cl 0.68194(16) 0.08022(5) -0.03610(9) 0.0511(3) Uani 1 1 d . . . C3 C 0.6803(4) 0.32186(14) -0.4261(3) 0.0215(8) Uani 1 1 d . . . C4 C 0.6539(4) 0.26221(15) -0.4107(3) 0.0217(8) Uani 1 1 d . . . C5 C 0.5907(4) 0.34316(15) -0.5234(3) 0.0266(8) Uani 1 1 d . . . H5A H 0.4822 0.3397 -0.5134 0.040 Uiso 1 1 calc R . . H5B H 0.6176 0.3229 -0.5845 0.040 Uiso 1 1 calc R . . H5C H 0.6158 0.3803 -0.5337 0.040 Uiso 1 1 calc R . . C6 C 0.8560(4) 0.32790(17) -0.4427(3) 0.0301(9) Uani 1 1 d . . . H6A H 0.9130 0.3144 -0.3817 0.045 Uiso 1 1 calc R . . H6B H 0.8803 0.3651 -0.4525 0.045 Uiso 1 1 calc R . . H6C H 0.8829 0.3079 -0.5041 0.045 Uiso 1 1 calc R . . C7 C 0.7085(4) 0.18405(13) -0.2936(3) 0.0191(7) Uani 1 1 d . . . C8 C 0.8604(4) 0.16615(14) -0.2966(3) 0.0219(8) Uani 1 1 d . . . C9 C 0.8858(4) 0.11110(14) -0.2877(3) 0.0241(8) Uani 1 1 d . . . H9A H 0.9865 0.0983 -0.2864 0.029 Uiso 1 1 calc R . . C10 C 0.7664(4) 0.07495(14) -0.2807(3) 0.0243(8) Uani 1 1 d . . . C11 C 0.6171(4) 0.09481(14) -0.2801(3) 0.0248(8) Uani 1 1 d . . . H11A H 0.5361 0.0706 -0.2759 0.030 Uiso 1 1 calc R . . C12 C 0.5838(4) 0.14938(14) -0.2855(3) 0.0208(8) Uani 1 1 d . . . C13 C 0.4208(4) 0.16873(15) -0.2816(3) 0.0313(9) Uani 1 1 d . . . H13A H 0.4151 0.1969 -0.2301 0.047 Uiso 1 1 calc R . . H13B H 0.3556 0.1395 -0.2623 0.047 Uiso 1 1 calc R . . H13C H 0.3873 0.1822 -0.3499 0.047 Uiso 1 1 calc R . . C14 C 0.7973(5) 0.01561(15) -0.2711(3) 0.0341(10) Uani 1 1 d . . . H14A H 0.8912 0.0071 -0.3048 0.051 Uiso 1 1 calc R . . H14B H 0.7136 -0.0040 -0.3047 0.051 Uiso 1 1 calc R . . H14C H 0.8070 0.0059 -0.1977 0.051 Uiso 1 1 calc R . . C15 C 0.9931(4) 0.20377(16) -0.3103(3) 0.0308(9) Uani 1 1 d . . . H15A H 0.9905 0.2318 -0.2583 0.046 Uiso 1 1 calc R . . H15B H 0.9854 0.2193 -0.3799 0.046 Uiso 1 1 calc R . . H15C H 1.0882 0.1843 -0.3016 0.046 Uiso 1 1 calc R . . C16 C 0.6983(4) 0.36322(13) -0.1353(3) 0.0189(7) Uani 1 1 d . . . C17 C 0.8484(4) 0.37889(14) -0.1065(3) 0.0211(8) Uani 1 1 d . . . C18 C 0.8659(4) 0.41694(15) -0.0263(3) 0.0257(8) Uani 1 1 d . . . H18A H 0.9647 0.4277 -0.0045 0.031 Uiso 1 1 calc R . . C19 C 0.7415(4) 0.43918(15) 0.0220(3) 0.0264(8) Uani 1 1 d . . . C20 C 0.5952(4) 0.42093(15) -0.0079(3) 0.0247(8) Uani 1 1 d . . . H20A H 0.5110 0.4351 0.0256 0.030 Uiso 1 1 calc R . . C21 C 0.5699(4) 0.38251(14) -0.0857(3) 0.0214(8) Uani 1 1 d . . . C22 C 0.4092(4) 0.36312(18) -0.1123(3) 0.0338(10) Uani 1 1 d . . . H22A H 0.4100 0.3248 -0.1206 0.051 Uiso 1 1 calc R . . H22B H 0.3718 0.3795 -0.1771 0.051 Uiso 1 1 calc R . . H22C H 0.3432 0.3727 -0.0563 0.051 Uiso 1 1 calc R . . C23 C 0.7629(5) 0.48252(18) 0.1053(4) 0.0423(11) Uani 1 1 d . . . H23A H 0.6876 0.5103 0.0926 0.063 Uiso 1 1 calc R . . H23B H 0.8644 0.4975 0.1021 0.063 Uiso 1 1 calc R . . H23C H 0.7503 0.4673 0.1741 0.063 Uiso 1 1 calc R . . C24 C 0.9870(4) 0.35613(16) -0.1579(3) 0.0291(9) Uani 1 1 d . . . H24A H 1.0786 0.3728 -0.1280 0.044 Uiso 1 1 calc R . . H24B H 0.9792 0.3630 -0.2326 0.044 Uiso 1 1 calc R . . H24C H 0.9918 0.3181 -0.1458 0.044 Uiso 1 1 calc R . . C25 C 0.7175(5) 0.05683(18) 0.0931(3) 0.0397(11) Uani 1 1 d . . . H25A H 0.7650 0.0857 0.1358 0.048 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 Br1 0.02500(19) 0.0223(2) 0.0233(2) 0.00100(14) -0.00114(15) 0.00151(15) Cl1 0.0553(8) 0.0768(11) 0.1047(13) 0.0082(9) 0.0033(8) 0.0178(8) N1 0.0175(14) 0.0171(15) 0.0201(15) 0.0007(12) -0.0011(12) -0.0007(12) O1 0.0498(17) 0.0159(14) 0.0298(15) 0.0024(11) -0.0052(13) 0.0000(12) C1 0.0104(15) 0.0231(19) 0.0182(18) 0.0037(14) 0.0009(14) -0.0020(14) Br2 0.02304(19) 0.01917(19) 0.01870(19) 0.00223(14) 0.00000(14) 0.00123(14) Cl2 0.0627(8) 0.0448(7) 0.0525(7) 0.0128(6) 0.0169(6) 0.0034(6) O2 0.0403(16) 0.0257(14) 0.0203(14) -0.0049(11) -0.0033(12) 0.0001(12) N2 0.0171(14) 0.0182(15) 0.0175(15) -0.0008(12) 0.0001(12) 0.0001(12) C2 0.0222(18) 0.020(2) 0.0223(19) 0.0031(15) -0.0005(15) -0.0037(15) Cl3 0.0802(9) 0.0455(7) 0.0278(6) -0.0014(5) 0.0044(6) -0.0172(6) C3 0.0239(19) 0.0206(18) 0.0198(18) 0.0026(15) -0.0011(15) -0.0010(15) C4 0.0181(17) 0.026(2) 0.0213(19) -0.0002(16) 0.0039(15) 0.0004(15) C5 0.033(2) 0.025(2) 0.0217(19) 0.0043(16) -0.0012(16) -0.0049(17) C6 0.024(2) 0.036(2) 0.030(2) 0.0036(18) 0.0033(17) -0.0057(17) C7 0.0241(18) 0.0148(17) 0.0183(18) -0.0001(14) 0.0011(15) 0.0013(15) C8 0.0221(18) 0.0242(19) 0.0196(18) -0.0017(15) 0.0035(15) 0.0007(15) C9 0.0213(18) 0.025(2) 0.026(2) -0.0004(16) 0.0011(16) 0.0076(16) C10 0.033(2) 0.0187(19) 0.0214(19) -0.0026(15) 0.0015(16) 0.0041(16) C11 0.027(2) 0.0212(19) 0.026(2) 0.0018(15) -0.0036(16) -0.0047(16) C12 0.0209(18) 0.0192(18) 0.0219(19) 0.0018(15) -0.0019(15) 0.0012(15) C13 0.0216(19) 0.024(2) 0.049(3) 0.0040(18) 0.0008(18) 0.0000(16) C14 0.039(2) 0.023(2) 0.040(2) -0.0020(18) 0.000(2) 0.0060(18) C15 0.0202(19) 0.030(2) 0.042(2) 0.0026(18) 0.0042(18) 0.0028(16) C16 0.0228(18) 0.0143(17) 0.0194(18) 0.0007(14) -0.0009(15) -0.0025(14) C17 0.0213(18) 0.0221(19) 0.0197(18) 0.0035(15) -0.0033(15) 0.0018(15) C18 0.0242(19) 0.027(2) 0.025(2) 0.0015(16) -0.0066(16) -0.0063(16) C19 0.033(2) 0.0206(19) 0.025(2) -0.0014(16) -0.0051(17) -0.0007(17) C20 0.027(2) 0.026(2) 0.0204(19) -0.0029(15) -0.0004(16) 0.0046(16) C21 0.0205(18) 0.0211(18) 0.0226(19) 0.0010(15) -0.0011(15) 0.0000(15) C22 0.022(2) 0.045(3) 0.034(2) -0.0112(19) 0.0045(17) -0.0022(18) C23 0.045(3) 0.040(3) 0.041(3) -0.017(2) -0.011(2) 0.004(2) C24 0.0196(18) 0.034(2) 0.033(2) -0.0021(18) -0.0016(16) -0.0035(17) C25 0.054(3) 0.034(2) 0.030(2) -0.0028(18) -0.003(2) -0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C25 1.757(5) . ? N1 C1 1.329(5) . ? N1 C2 1.467(4) . ? N1 C16 1.469(4) . ? O1 C2 1.183(4) . ? C1 N2 1.333(4) . ? C1 Br2 1.885(3) . ? Cl2 C25 1.757(5) . ? O2 C4 1.191(4) . ? N2 C4 1.450(4) . ? N2 C7 1.468(4) . ? C2 C3 1.507(5) . ? Cl3 C25 1.750(4) . ? C3 C4 1.516(5) . ? C3 C5 1.523(5) . ? C3 C6 1.556(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.392(5) . ? C7 C8 1.395(5) . ? C8 C9 1.392(5) . ? C8 C15 1.501(5) . ? C9 C10 1.379(5) . ? C9 H9A 0.9300 . ? C10 C11 1.388(5) . ? C10 C14 1.505(5) . ? C11 C12 1.390(5) . ? C11 H11A 0.9300 . ? C12 C13 1.499(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C21 1.389(5) . ? C16 C17 1.395(5) . ? C17 C18 1.392(5) . ? C17 C24 1.503(5) . ? C18 C19 1.380(5) . ? C18 H18A 0.9300 . ? C19 C20 1.387(5) . ? C19 C23 1.514(5) . ? C20 C21 1.383(5) . ? C20 H20A 0.9300 . ? C21 C22 1.501(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 121.7(3) . . ? C1 N1 C16 122.7(3) . . ? C2 N1 C16 115.5(3) . . ? N1 C1 N2 123.0(3) . . ? N1 C1 Br2 118.0(2) . . ? N2 C1 Br2 119.1(3) . . ? C1 N2 C4 122.3(3) . . ? C1 N2 C7 121.3(3) . . ? C4 N2 C7 116.3(3) . . ? O1 C2 N1 118.4(3) . . ? O1 C2 C3 125.3(3) . . ? N1 C2 C3 116.0(3) . . ? C2 C3 C4 112.7(3) . . ? C2 C3 C5 111.2(3) . . ? C4 C3 C5 111.7(3) . . ? C2 C3 C6 106.2(3) . . ? C4 C3 C6 105.5(3) . . ? C5 C3 C6 109.1(3) . . ? O2 C4 N2 118.5(3) . . ? O2 C4 C3 124.9(3) . . ? N2 C4 C3 116.1(3) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 123.0(3) . . ? C12 C7 N2 119.5(3) . . ? C8 C7 N2 117.5(3) . . ? C9 C8 C7 117.4(3) . . ? C9 C8 C15 120.2(3) . . ? C7 C8 C15 122.4(3) . . ? C10 C9 C8 122.0(3) . . ? C10 C9 H9A 119.0 . . ? C8 C9 H9A 119.0 . . ? C9 C10 C11 118.3(3) . . ? C9 C10 C14 120.9(3) . . ? C11 C10 C14 120.9(3) . . ? C10 C11 C12 122.7(3) . . ? C10 C11 H11A 118.6 . . ? C12 C11 H11A 118.6 . . ? C11 C12 C7 116.6(3) . . ? C11 C12 C13 120.5(3) . . ? C7 C12 C13 122.9(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 123.0(3) . . ? C21 C16 N1 119.4(3) . . ? C17 C16 N1 117.4(3) . . ? C18 C17 C16 116.9(3) . . ? C18 C17 C24 120.4(3) . . ? C16 C17 C24 122.6(3) . . ? C19 C18 C17 122.2(3) . . ? C19 C18 H18A 118.9 . . ? C17 C18 H18A 118.9 . . ? C18 C19 C20 118.3(3) . . ? C18 C19 C23 121.2(4) . . ? C20 C19 C23 120.5(4) . . ? C21 C20 C19 122.5(3) . . ? C21 C20 H20A 118.8 . . ? C19 C20 H20A 118.8 . . ? C20 C21 C16 117.0(3) . . ? C20 C21 C22 120.0(3) . . ? C16 C21 C22 123.0(3) . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 H24A 109.5 . . ? C17 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl3 C25 Cl1 110.7(3) . . ? Cl3 C25 Cl2 109.9(2) . . ? Cl1 C25 Cl2 109.3(2) . . ? Cl3 C25 H25A 109.0 . . ? Cl1 C25 H25A 109.0 . . ? Cl2 C25 H25A 109.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.771 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.079 data_6MesBr2 _database_code_depnum_ccdc_archive 'CCDC 882671' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6satMesBr2 _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Br2 N2; CHCl3' _chemical_formula_sum 'C23 H29 Br2 Cl3 N2' _chemical_formula_weight 599.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.893(2) _cell_length_b 8.2648(9) _cell_length_c 17.927(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.099(2) _cell_angle_gamma 90.00 _cell_volume 2660.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 3.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37561 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4684 _reflns_number_gt 4010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+13.7292P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4684 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.30897(3) 0.66912(6) 0.47236(3) 0.02575(17) Uani 1 1 d . . . Cl1 Cl -0.14510(13) 1.0707(3) 0.20718(15) 0.0829(7) Uani 1 1 d . . . N1 N 0.3687(2) 0.6836(5) 0.6347(2) 0.0178(8) Uani 1 1 d . . . C1 C 0.3072(3) 0.6497(6) 0.5782(3) 0.0180(10) Uani 1 1 d . . . Br2 Br 0.33012(3) 0.72569(7) 0.29911(3) 0.03502(18) Uani 1 1 d . . . Cl2 Cl -0.10979(16) 0.7279(4) 0.20523(15) 0.0987(10) Uani 1 1 d . . . N2 N 0.2438(2) 0.6093(5) 0.5899(2) 0.0207(9) Uani 1 1 d . . . C2 C 0.3708(3) 0.6693(7) 0.7177(3) 0.0245(11) Uani 1 1 d . . . H2A H 0.4088 0.7403 0.7503 0.029 Uiso 1 1 calc R . . H2B H 0.3829 0.5591 0.7358 0.029 Uiso 1 1 calc R . . Cl3 Cl -0.11113(12) 0.8784(3) 0.34852(11) 0.0705(6) Uani 1 1 d . . . C3 C 0.2950(3) 0.7155(7) 0.7247(3) 0.0312(12) Uani 1 1 d . . . H3A H 0.2948 0.7002 0.7783 0.037 Uiso 1 1 calc R . . H3B H 0.2847 0.8286 0.7110 0.037 Uiso 1 1 calc R . . C4 C 0.2358(3) 0.6106(7) 0.6699(3) 0.0283(12) Uani 1 1 d . . . H4A H 0.2401 0.5011 0.6902 0.034 Uiso 1 1 calc R . . H4B H 0.1869 0.6514 0.6672 0.034 Uiso 1 1 calc R . . C5 C 0.1809(2) 0.5437(6) 0.5288(3) 0.0198(10) Uani 1 1 d . . . C6 C 0.1220(3) 0.6453(6) 0.4909(3) 0.0242(11) Uani 1 1 d . . . C7 C 0.0599(3) 0.5748(7) 0.4377(3) 0.0292(12) Uani 1 1 d . . . H7A H 0.0195 0.6401 0.4123 0.035 Uiso 1 1 calc R . . C8 C 0.0560(3) 0.4116(7) 0.4212(3) 0.0291(12) Uani 1 1 d . . . C9 C 0.1164(3) 0.3159(7) 0.4592(3) 0.0297(12) Uani 1 1 d . . . H9A H 0.1147 0.2062 0.4472 0.036 Uiso 1 1 calc R . . C10 C 0.1796(3) 0.3771(6) 0.5148(3) 0.0232(11) Uani 1 1 d . . . C11 C 0.2445(3) 0.2699(7) 0.5560(4) 0.0357(13) Uani 1 1 d . . . H11A H 0.2340 0.1609 0.5373 0.054 Uiso 1 1 calc R . . H11B H 0.2523 0.2727 0.6115 0.054 Uiso 1 1 calc R . . H11C H 0.2884 0.3077 0.5454 0.054 Uiso 1 1 calc R . . C12 C -0.0119(3) 0.3390(10) 0.3617(4) 0.0509(18) Uani 1 1 d . . . H12A H -0.0386 0.4222 0.3269 0.076 Uiso 1 1 calc R . . H12B H -0.0436 0.2916 0.3885 0.076 Uiso 1 1 calc R . . H12C H 0.0035 0.2571 0.3320 0.076 Uiso 1 1 calc R . . C13 C 0.1265(4) 0.8243(7) 0.5042(4) 0.0388(14) Uani 1 1 d . . . H13A H 0.0773 0.8698 0.4868 0.058 Uiso 1 1 calc R . . H13B H 0.1562 0.8719 0.4751 0.058 Uiso 1 1 calc R . . H13C H 0.1489 0.8461 0.5591 0.058 Uiso 1 1 calc R . . C14 C 0.4374(3) 0.7305(6) 0.6203(3) 0.0170(10) Uani 1 1 d . . . C15 C 0.4556(3) 0.8947(6) 0.6245(3) 0.0198(10) Uani 1 1 d . . . C16 C 0.5212(3) 0.9374(6) 0.6093(3) 0.0232(11) Uani 1 1 d . . . H16A H 0.5343 1.0460 0.6107 0.028 Uiso 1 1 calc R . . C17 C 0.5673(3) 0.8223(6) 0.5922(3) 0.0229(11) Uani 1 1 d . . . C18 C 0.5480(3) 0.6593(6) 0.5916(3) 0.0230(11) Uani 1 1 d . . . H18A H 0.5792 0.5816 0.5810 0.028 Uiso 1 1 calc R . . C19 C 0.4834(3) 0.6101(6) 0.6064(3) 0.0199(10) Uani 1 1 d . . . C20 C 0.4649(3) 0.4328(6) 0.6094(3) 0.0262(11) Uani 1 1 d . . . H20A H 0.4459 0.4140 0.6525 0.039 Uiso 1 1 calc R . . H20B H 0.5090 0.3694 0.6163 0.039 Uiso 1 1 calc R . . H20C H 0.4280 0.4025 0.5612 0.039 Uiso 1 1 calc R . . C21 C 0.6369(3) 0.8733(7) 0.5743(3) 0.0308(12) Uani 1 1 d . . . H21A H 0.6637 0.9507 0.6127 0.046 Uiso 1 1 calc R . . H21B H 0.6237 0.9213 0.5231 0.046 Uiso 1 1 calc R . . H21C H 0.6678 0.7803 0.5758 0.046 Uiso 1 1 calc R . . C22 C 0.4072(3) 1.0204(6) 0.6450(3) 0.0304(12) Uani 1 1 d . . . H22A H 0.4218 1.1260 0.6329 0.046 Uiso 1 1 calc R . . H22B H 0.4127 1.0141 0.7000 0.046 Uiso 1 1 calc R . . H22C H 0.3561 1.0013 0.6152 0.046 Uiso 1 1 calc R . . C23 C -0.1500(4) 0.8769(9) 0.2462(4) 0.0457(16) Uani 1 1 d . . . H23A H -0.2028 0.8497 0.2343 0.055 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 Br1 0.0234(3) 0.0311(3) 0.0223(3) 0.0005(2) 0.0063(2) -0.0013(2) Cl1 0.0663(13) 0.0867(16) 0.0923(17) 0.0188(13) 0.0196(12) -0.0187(12) N1 0.018(2) 0.017(2) 0.018(2) 0.0015(16) 0.0050(16) -0.0015(16) C1 0.018(2) 0.017(2) 0.017(2) -0.0007(19) 0.0030(19) 0.0012(19) Br2 0.0308(3) 0.0371(3) 0.0336(3) -0.0085(2) 0.0048(2) 0.0040(2) Cl2 0.0894(17) 0.138(2) 0.0710(15) -0.0372(15) 0.0278(13) 0.0419(17) N2 0.017(2) 0.022(2) 0.022(2) -0.0009(17) 0.0062(17) -0.0026(17) C2 0.021(3) 0.036(3) 0.016(2) 0.003(2) 0.005(2) -0.007(2) Cl3 0.0700(13) 0.1021(17) 0.0394(10) -0.0152(10) 0.0173(9) 0.0039(12) C3 0.030(3) 0.043(3) 0.020(3) -0.008(2) 0.008(2) -0.007(3) C4 0.020(3) 0.042(3) 0.025(3) -0.005(2) 0.009(2) -0.007(2) C5 0.012(2) 0.027(3) 0.020(2) 0.000(2) 0.0056(18) -0.0041(19) C6 0.019(2) 0.030(3) 0.026(3) 0.000(2) 0.010(2) 0.001(2) C7 0.018(3) 0.045(3) 0.025(3) 0.008(2) 0.005(2) 0.005(2) C8 0.021(3) 0.045(4) 0.021(3) -0.003(2) 0.006(2) -0.010(2) C9 0.028(3) 0.031(3) 0.032(3) -0.005(2) 0.013(2) -0.010(2) C10 0.019(2) 0.026(3) 0.026(3) 0.001(2) 0.009(2) -0.002(2) C11 0.037(3) 0.024(3) 0.047(4) 0.005(3) 0.014(3) 0.006(2) C12 0.029(3) 0.077(5) 0.043(4) -0.014(4) 0.006(3) -0.020(3) C13 0.039(3) 0.026(3) 0.048(4) 0.001(3) 0.009(3) 0.008(3) C14 0.014(2) 0.020(2) 0.015(2) 0.0008(19) 0.0022(18) -0.0035(18) C15 0.022(2) 0.017(2) 0.019(2) 0.0017(19) 0.0050(19) 0.0016(19) C16 0.024(3) 0.022(3) 0.022(3) 0.002(2) 0.006(2) -0.007(2) C17 0.021(2) 0.029(3) 0.018(2) 0.002(2) 0.004(2) -0.003(2) C18 0.024(3) 0.025(3) 0.021(2) 0.000(2) 0.007(2) 0.002(2) C19 0.023(2) 0.018(2) 0.016(2) -0.0005(19) 0.0007(19) 0.000(2) C20 0.030(3) 0.019(3) 0.028(3) -0.003(2) 0.008(2) -0.002(2) C21 0.026(3) 0.042(3) 0.027(3) 0.003(2) 0.012(2) -0.007(2) C22 0.031(3) 0.018(3) 0.044(3) 0.001(2) 0.013(2) 0.001(2) C23 0.036(3) 0.060(4) 0.042(4) -0.013(3) 0.014(3) -0.002(3) _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 Br1 C1 1.916(5) . ? Cl1 C23 1.762(8) . ? N1 C1 1.313(6) . ? N1 C14 1.453(6) . ? N1 C2 1.481(6) . ? C1 N2 1.321(6) . ? Cl2 C23 1.726(7) . ? N2 C5 1.447(6) . ? N2 C4 1.488(6) . ? C2 C3 1.524(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? Cl3 C23 1.752(7) . ? C3 C4 1.511(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.392(7) . ? C5 C10 1.398(7) . ? C6 C7 1.389(7) . ? C6 C13 1.497(8) . ? C7 C8 1.378(8) . ? C7 H7A 0.9300 . ? C8 C9 1.381(8) . ? C8 C12 1.515(8) . ? C9 C10 1.392(7) . ? C9 H9A 0.9300 . ? C10 C11 1.507(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.393(7) . ? C14 C15 1.396(7) . ? C15 C16 1.393(7) . ? C15 C22 1.504(7) . ? C16 C17 1.387(7) . ? C16 H16A 0.9300 . ? C17 C18 1.395(7) . ? C17 C21 1.508(7) . ? C18 C19 1.389(7) . ? C18 H18A 0.9300 . ? C19 C20 1.511(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C14 123.0(4) . . ? C1 N1 C2 119.9(4) . . ? C14 N1 C2 117.0(4) . . ? N1 C1 N2 124.1(4) . . ? N1 C1 Br1 117.5(3) . . ? N2 C1 Br1 118.3(3) . . ? C1 N2 C5 123.1(4) . . ? C1 N2 C4 121.2(4) . . ? C5 N2 C4 115.3(4) . . ? N1 C2 C3 109.3(4) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C2 109.1(4) . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N2 C4 C3 110.8(4) . . ? N2 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C10 122.7(5) . . ? C6 C5 N2 119.2(4) . . ? C10 C5 N2 118.0(4) . . ? C7 C6 C5 117.3(5) . . ? C7 C6 C13 121.2(5) . . ? C5 C6 C13 121.4(5) . . ? C8 C7 C6 122.3(5) . . ? C8 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? C7 C8 C9 118.3(5) . . ? C7 C8 C12 121.0(6) . . ? C9 C8 C12 120.6(6) . . ? C8 C9 C10 122.6(5) . . ? C8 C9 H9A 118.7 . . ? C10 C9 H9A 118.7 . . ? C9 C10 C5 116.8(5) . . ? C9 C10 C11 121.5(5) . . ? C5 C10 C11 121.7(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C6 C13 H13A 109.5 . . ? C6 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C6 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 123.2(4) . . ? C19 C14 N1 118.8(4) . . ? C15 C14 N1 118.0(4) . . ? C16 C15 C14 117.1(4) . . ? C16 C15 C22 121.2(5) . . ? C14 C15 C22 121.7(4) . . ? C17 C16 C15 121.8(5) . . ? C17 C16 H16A 119.1 . . ? C15 C16 H16A 119.1 . . ? C16 C17 C18 118.9(5) . . ? C16 C17 C21 120.3(5) . . ? C18 C17 C21 120.7(5) . . ? C19 C18 C17 121.6(5) . . ? C19 C18 H18A 119.2 . . ? C17 C18 H18A 119.2 . . ? C18 C19 C14 117.3(4) . . ? C18 C19 C20 121.1(4) . . ? C14 C19 C20 121.5(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C22 H22A 109.5 . . ? C15 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C15 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Cl2 C23 Cl3 110.7(4) . . ? Cl2 C23 Cl1 113.3(4) . . ? Cl3 C23 Cl1 110.6(4) . . ? Cl2 C23 H23A 107.3 . . ? Cl3 C23 H23A 107.3 . . ? Cl1 C23 H23A 107.3 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.846 _refine_diff_density_min -0.917 _refine_diff_density_rms 0.112 data_SIMesBr2 _database_code_depnum_ccdc_archive 'CCDC 882672' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SIMesBr2 _chemical_melting_point ? _chemical_formula_moiety '2C21H23N2Br2; 3CHCl3' _chemical_formula_sum 'C45 H55 Br4 Cl9 N4' _chemical_formula_weight 1290.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 28.784(3) _cell_length_b 28.621(3) _cell_length_c 13.8010(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 11369.5(19) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5168 _exptl_absorpt_coefficient_mu 3.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.583 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 122939 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9902 _reflns_number_gt 7138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+63.9088P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9902 _refine_ls_number_parameters 571 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.23995(2) 0.21126(2) 0.24926(5) 0.03120(17) Uani 1 1 d . . . N1 N 0.21900(17) 0.29839(17) 0.3308(4) 0.0308(12) Uani 1 1 d . . . C1 C 0.2510(2) 0.2657(2) 0.3209(4) 0.0272(14) Uani 1 1 d . . . Cl1 Cl 0.08870(8) 0.53495(9) 0.58201(16) 0.0734(7) Uani 1 1 d . . . Br2 Br 0.22047(2) 0.12338(2) 0.12143(5) 0.03730(18) Uani 1 1 d . . . N2 N 0.29057(17) 0.27522(16) 0.3631(3) 0.0257(11) Uani 1 1 d . . . C2 C 0.2391(2) 0.3379(2) 0.3863(5) 0.0355(16) Uani 1 1 d . . . H2A H 0.2206 0.3448 0.4432 0.043 Uiso 1 1 calc R . . H2B H 0.2412 0.3657 0.3464 0.043 Uiso 1 1 calc R . . Cl2 Cl 0.07933(6) 0.52836(7) 0.79094(14) 0.0513(5) Uani 1 1 d . . . Br3 Br 0.22811(2) 0.55917(2) 0.51235(4) 0.03236(17) Uani 1 1 d . . . N3 N 0.29206(16) 0.53236(17) 0.3704(4) 0.0279(12) Uani 1 1 d . . . C3 C 0.2871(2) 0.3205(2) 0.4148(5) 0.0335(15) Uani 1 1 d . . . H3A H 0.3111 0.3420 0.3935 0.040 Uiso 1 1 calc R . . H3B H 0.2895 0.3163 0.4843 0.040 Uiso 1 1 calc R . . Cl3 Cl 0.02968(9) 0.59908(9) 0.68474(18) 0.0780(7) Uani 1 1 d . . . Br4 Br 0.30555(2) 0.39490(2) 0.20572(5) 0.03679(18) Uani 1 1 d . . . N4 N 0.21982(16) 0.52684(18) 0.3216(4) 0.0294(12) Uani 1 1 d . . . C4 C 0.1706(2) 0.2956(2) 0.3075(5) 0.0322(15) Uani 1 1 d . . . Cl4 Cl 0.06875(13) 0.64007(14) 0.9241(3) 0.1331(13) Uani 1 1 d . . . C5 C 0.1410(2) 0.2741(2) 0.3745(5) 0.0421(17) Uani 1 1 d . . . Cl5 Cl 0.11119(15) 0.66911(15) 1.0968(3) 0.1368(13) Uani 1 1 d . . . C6 C 0.0941(3) 0.2731(3) 0.3516(6) 0.052(2) Uani 1 1 d . . . H6A H 0.0738 0.2587 0.3945 0.062 Uiso 1 1 calc R . . Cl6 Cl 0.0180(2) 0.6945(3) 1.0585(5) 0.248(3) Uani 1 1 d . . . C7 C 0.0763(2) 0.2925(3) 0.2682(6) 0.050(2) Uani 1 1 d . . . Cl7 Cl 0.06978(10) 0.12695(11) 0.0068(2) 0.1016(10) Uani 1 1 d . . . C8 C 0.1067(2) 0.3144(2) 0.2052(6) 0.0449(18) Uani 1 1 d . . . H8A H 0.0950 0.3281 0.1491 0.054 Uiso 1 1 calc R . . Cl8 Cl 0.08722(11) 0.08653(12) 0.1910(3) 0.1356(16) Uani 1 1 d . . . C9 C 0.1547(2) 0.3166(2) 0.2237(5) 0.0348(15) Uani 1 1 d . . . Cl9 Cl 0.08857(11) 0.18690(10) 0.1671(3) 0.1077(10) Uani 1 1 d . . . C10 C 0.1863(2) 0.3408(3) 0.1538(5) 0.0459(18) Uani 1 1 d . . . H10A H 0.2065 0.3183 0.1239 0.069 Uiso 1 1 calc R . . H10B H 0.2047 0.3636 0.1878 0.069 Uiso 1 1 calc R . . H10C H 0.1682 0.3562 0.1049 0.069 Uiso 1 1 calc R . . C11 C 0.0252(3) 0.2897(3) 0.2462(8) 0.080(3) Uani 1 1 d . . . H11A H 0.0078 0.2981 0.3028 0.120 Uiso 1 1 calc R . . H11B H 0.0174 0.2584 0.2273 0.120 Uiso 1 1 calc R . . H11C H 0.0178 0.3108 0.1943 0.120 Uiso 1 1 calc R . . C12 C 0.1592(3) 0.2535(3) 0.4675(6) 0.057(2) Uani 1 1 d . . . H12A H 0.1336 0.2427 0.5062 0.085 Uiso 1 1 calc R . . H12B H 0.1761 0.2768 0.5027 0.085 Uiso 1 1 calc R . . H12C H 0.1793 0.2277 0.4530 0.085 Uiso 1 1 calc R . . C13 C 0.3296(2) 0.2444(2) 0.3781(4) 0.0278(14) Uani 1 1 d . . . C14 C 0.3286(2) 0.2137(2) 0.4550(5) 0.0309(14) Uani 1 1 d . . . C15 C 0.3686(2) 0.1879(2) 0.4750(5) 0.0357(16) Uani 1 1 d . . . H15A H 0.3685 0.1670 0.5266 0.043 Uiso 1 1 calc R . . C16 C 0.4085(2) 0.1927(2) 0.4194(5) 0.0388(16) Uani 1 1 d . . . C17 C 0.4075(2) 0.2228(2) 0.3416(5) 0.0366(16) Uani 1 1 d . . . H17A H 0.4339 0.2254 0.3030 0.044 Uiso 1 1 calc R . . C18 C 0.3687(2) 0.2494(2) 0.3186(5) 0.0330(15) Uani 1 1 d . . . C19 C 0.3691(2) 0.2815(3) 0.2318(5) 0.0463(19) Uani 1 1 d . . . H19A H 0.3552 0.3108 0.2489 0.069 Uiso 1 1 calc R . . H19B H 0.3519 0.2674 0.1799 0.069 Uiso 1 1 calc R . . H19C H 0.4006 0.2866 0.2115 0.069 Uiso 1 1 calc R . . C20 C 0.4519(2) 0.1660(3) 0.4463(6) 0.053(2) Uani 1 1 d . . . H20A H 0.4710 0.1620 0.3898 0.080 Uiso 1 1 calc R . . H20B H 0.4435 0.1360 0.4716 0.080 Uiso 1 1 calc R . . H20C H 0.4689 0.1831 0.4946 0.080 Uiso 1 1 calc R . . C21 C 0.2853(2) 0.2060(2) 0.5152(5) 0.0412(17) Uani 1 1 d . . . H21A H 0.2750 0.2354 0.5411 0.062 Uiso 1 1 calc R . . H21B H 0.2922 0.1850 0.5673 0.062 Uiso 1 1 calc R . . H21C H 0.2613 0.1929 0.4752 0.062 Uiso 1 1 calc R . . C22 C 0.2482(2) 0.5370(2) 0.3922(4) 0.0268(14) Uani 1 1 d . . . C23 C 0.2970(2) 0.5173(2) 0.2673(4) 0.0294(14) Uani 1 1 d . . . H23A H 0.3132 0.4877 0.2626 0.035 Uiso 1 1 calc R . . H23B H 0.3136 0.5405 0.2294 0.035 Uiso 1 1 calc R . . C24 C 0.2464(2) 0.5127(2) 0.2336(4) 0.0302(14) Uani 1 1 d . . . H24A H 0.2399 0.5334 0.1795 0.036 Uiso 1 1 calc R . . H24B H 0.2392 0.4809 0.2149 0.036 Uiso 1 1 calc R . . C25 C 0.17002(19) 0.5289(2) 0.3249(4) 0.0273(14) Uani 1 1 d . . . C26 C 0.1458(2) 0.4878(2) 0.3486(5) 0.0355(15) Uani 1 1 d . . . C27 C 0.0979(2) 0.4907(2) 0.3518(5) 0.0448(18) Uani 1 1 d . . . H27A H 0.0809 0.4643 0.3689 0.054 Uiso 1 1 calc R . . C28 C 0.0743(2) 0.5317(2) 0.3304(5) 0.0409(17) Uani 1 1 d . . . C29 C 0.0999(2) 0.5708(2) 0.3071(5) 0.0388(16) Uani 1 1 d . . . H29A H 0.0843 0.5984 0.2930 0.047 Uiso 1 1 calc R . . C30 C 0.1479(2) 0.5707(2) 0.3040(4) 0.0309(14) Uani 1 1 d . . . C31 C 0.1748(3) 0.6142(2) 0.2814(6) 0.0488(19) Uani 1 1 d . . . H31A H 0.1537 0.6398 0.2722 0.073 Uiso 1 1 calc R . . H31B H 0.1926 0.6095 0.2234 0.073 Uiso 1 1 calc R . . H31C H 0.1954 0.6212 0.3343 0.073 Uiso 1 1 calc R . . C32 C 0.0222(2) 0.5332(3) 0.3370(7) 0.066(2) Uani 1 1 d . . . H32A H 0.0098 0.5484 0.2806 0.099 Uiso 1 1 calc R . . H32B H 0.0132 0.5503 0.3939 0.099 Uiso 1 1 calc R . . H32C H 0.0102 0.5020 0.3408 0.099 Uiso 1 1 calc R . . C33 C 0.1710(3) 0.4430(3) 0.3734(6) 0.058(2) Uani 1 1 d . . . H33A H 0.1490 0.4178 0.3775 0.087 Uiso 1 1 calc R . . H33B H 0.1865 0.4465 0.4346 0.087 Uiso 1 1 calc R . . H33C H 0.1934 0.4362 0.3240 0.087 Uiso 1 1 calc R . . C34 C 0.3318(2) 0.5375(2) 0.4337(4) 0.0285(14) Uani 1 1 d . . . C35 C 0.3464(2) 0.4987(2) 0.4865(5) 0.0352(15) Uani 1 1 d . . . C36 C 0.3863(2) 0.5045(3) 0.5436(5) 0.0477(19) Uani 1 1 d . . . H36A H 0.3965 0.4798 0.5817 0.057 Uiso 1 1 calc R . . C37 C 0.4107(2) 0.5455(3) 0.5447(5) 0.053(2) Uani 1 1 d . . . C38 C 0.3948(2) 0.5830(3) 0.4926(5) 0.0448(18) Uani 1 1 d . . . H38A H 0.4111 0.6110 0.4955 0.054 Uiso 1 1 calc R . . C39 C 0.3546(2) 0.5804(2) 0.4351(5) 0.0357(15) Uani 1 1 d . . . C40 C 0.3359(3) 0.6220(2) 0.3819(5) 0.0444(18) Uani 1 1 d . . . H40A H 0.3288 0.6134 0.3163 0.067 Uiso 1 1 calc R . . H40B H 0.3587 0.6465 0.3820 0.067 Uiso 1 1 calc R . . H40C H 0.3081 0.6328 0.4134 0.067 Uiso 1 1 calc R . . C41 C 0.4542(3) 0.5502(4) 0.6063(7) 0.088(3) Uani 1 1 d . . . H41A H 0.4783 0.5648 0.5689 0.132 Uiso 1 1 calc R . . H41B H 0.4643 0.5198 0.6265 0.132 Uiso 1 1 calc R . . H41C H 0.4475 0.5689 0.6622 0.132 Uiso 1 1 calc R . . C42 C 0.3209(3) 0.4527(3) 0.4816(5) 0.0481(19) Uani 1 1 d . . . H42A H 0.3333 0.4317 0.5292 0.072 Uiso 1 1 calc R . . H42B H 0.3246 0.4394 0.4182 0.072 Uiso 1 1 calc R . . H42C H 0.2884 0.4578 0.4941 0.072 Uiso 1 1 calc R . . C43 C 0.0816(3) 0.5657(3) 0.6895(6) 0.052(2) Uani 1 1 d . . . H43A H 0.1079 0.5871 0.6973 0.062 Uiso 1 1 calc R . . C44 C 0.0722(4) 0.6854(4) 1.0133(8) 0.102(4) Uani 1 1 d . . . H44A H 0.0830 0.7142 0.9821 0.123 Uiso 1 1 calc R . . C45 C 0.0997(3) 0.1330(3) 0.1173(7) 0.069(3) Uani 1 1 d . . . H45A H 0.1330 0.1317 0.1027 0.083 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 Br1 0.0311(3) 0.0273(3) 0.0352(4) -0.0021(3) -0.0001(3) 0.0024(3) N1 0.031(3) 0.030(3) 0.031(3) -0.003(2) 0.002(2) 0.006(2) C1 0.034(4) 0.023(3) 0.025(3) 0.004(3) 0.002(3) 0.004(3) Cl1 0.0649(14) 0.1035(18) 0.0518(14) -0.0170(12) 0.0141(11) -0.0107(13) Br2 0.0420(4) 0.0383(4) 0.0315(4) 0.0007(3) -0.0023(3) -0.0019(3) N2 0.030(3) 0.023(3) 0.025(3) -0.005(2) -0.005(2) 0.003(2) C2 0.045(4) 0.027(3) 0.035(4) -0.003(3) 0.001(3) 0.006(3) Cl2 0.0415(10) 0.0639(12) 0.0485(11) 0.0016(9) -0.0028(8) 0.0027(9) Br3 0.0280(3) 0.0435(4) 0.0256(4) -0.0042(3) 0.0015(2) 0.0036(3) N3 0.020(3) 0.037(3) 0.027(3) -0.006(2) -0.001(2) 0.003(2) C3 0.036(4) 0.026(3) 0.039(4) -0.005(3) -0.007(3) 0.003(3) Cl3 0.0780(16) 0.0781(16) 0.0780(17) 0.0213(13) 0.0121(13) 0.0231(13) Br4 0.0436(4) 0.0309(3) 0.0359(4) 0.0044(3) -0.0096(3) -0.0055(3) N4 0.023(3) 0.040(3) 0.025(3) -0.006(2) -0.002(2) 0.002(2) C4 0.030(4) 0.029(3) 0.038(4) -0.006(3) -0.003(3) 0.009(3) Cl4 0.128(3) 0.154(3) 0.118(3) -0.064(2) -0.017(2) 0.006(2) C5 0.036(4) 0.035(4) 0.054(5) 0.003(3) 0.007(3) 0.009(3) Cl5 0.164(4) 0.159(3) 0.087(2) -0.015(2) -0.015(2) -0.014(3) C6 0.041(4) 0.046(4) 0.069(6) 0.006(4) 0.016(4) -0.003(3) Cl6 0.171(5) 0.334(8) 0.238(6) -0.091(6) 0.033(4) 0.126(5) C7 0.030(4) 0.044(4) 0.075(6) -0.008(4) 0.001(4) 0.006(3) Cl7 0.0809(19) 0.129(2) 0.095(2) -0.0236(18) -0.0003(15) 0.0437(17) C8 0.034(4) 0.045(4) 0.056(5) -0.006(4) -0.009(3) 0.015(3) Cl8 0.089(2) 0.110(2) 0.208(4) 0.079(3) -0.064(2) -0.0573(19) C9 0.032(4) 0.034(4) 0.038(4) -0.008(3) 0.001(3) 0.008(3) Cl9 0.108(2) 0.0785(19) 0.137(3) -0.0265(18) 0.002(2) 0.0099(16) C10 0.039(4) 0.058(5) 0.040(4) 0.006(4) 0.000(3) 0.003(3) C11 0.031(4) 0.079(6) 0.130(9) 0.008(6) 0.002(5) 0.001(4) C12 0.058(5) 0.060(5) 0.053(5) 0.020(4) 0.014(4) 0.006(4) C13 0.030(3) 0.024(3) 0.029(4) -0.003(3) -0.008(3) 0.004(3) C14 0.033(4) 0.028(3) 0.032(4) -0.001(3) -0.004(3) 0.003(3) C15 0.046(4) 0.034(4) 0.028(4) 0.004(3) -0.010(3) 0.007(3) C16 0.033(4) 0.034(4) 0.050(5) -0.008(3) -0.007(3) 0.005(3) C17 0.032(4) 0.035(4) 0.043(4) 0.000(3) 0.003(3) 0.003(3) C18 0.035(4) 0.027(3) 0.036(4) -0.002(3) -0.001(3) 0.000(3) C19 0.042(4) 0.053(5) 0.044(5) 0.017(4) 0.014(3) 0.011(3) C20 0.039(4) 0.059(5) 0.062(5) 0.003(4) -0.012(4) 0.015(4) C21 0.039(4) 0.042(4) 0.043(4) 0.008(3) 0.006(3) 0.007(3) C22 0.028(3) 0.027(3) 0.024(3) 0.000(3) 0.005(3) 0.002(3) C23 0.022(3) 0.033(3) 0.033(4) -0.009(3) 0.000(3) 0.003(3) C24 0.029(3) 0.044(4) 0.018(3) -0.005(3) 0.003(3) 0.004(3) C25 0.019(3) 0.036(4) 0.026(3) -0.008(3) -0.003(2) 0.002(3) C26 0.032(4) 0.032(4) 0.042(4) -0.002(3) 0.005(3) -0.002(3) C27 0.034(4) 0.043(4) 0.058(5) -0.006(4) 0.009(3) -0.010(3) C28 0.025(4) 0.049(4) 0.048(4) -0.012(4) -0.005(3) 0.000(3) C29 0.034(4) 0.035(4) 0.047(4) -0.005(3) -0.006(3) 0.007(3) C30 0.027(3) 0.036(4) 0.030(4) -0.004(3) 0.000(3) 0.000(3) C31 0.044(4) 0.037(4) 0.065(5) 0.000(4) 0.012(4) 0.003(3) C32 0.028(4) 0.070(6) 0.100(7) -0.020(5) -0.001(4) -0.001(4) C33 0.053(5) 0.042(4) 0.078(6) 0.013(4) 0.013(4) 0.007(4) C34 0.020(3) 0.042(4) 0.024(3) -0.001(3) 0.001(3) 0.005(3) C35 0.027(3) 0.048(4) 0.031(4) 0.002(3) 0.004(3) 0.004(3) C36 0.039(4) 0.064(5) 0.040(4) 0.015(4) -0.007(3) 0.006(4) C37 0.030(4) 0.088(6) 0.041(5) 0.008(4) -0.011(3) -0.002(4) C38 0.037(4) 0.060(5) 0.038(4) -0.005(4) -0.004(3) -0.014(4) C39 0.028(3) 0.049(4) 0.031(4) -0.007(3) -0.001(3) 0.003(3) C40 0.053(5) 0.040(4) 0.041(4) -0.004(3) -0.005(3) 0.000(3) C41 0.048(5) 0.128(9) 0.087(7) 0.012(6) -0.026(5) -0.012(6) C42 0.047(4) 0.054(5) 0.044(5) 0.018(4) 0.002(3) -0.002(4) C43 0.039(4) 0.063(5) 0.052(5) 0.004(4) 0.005(4) -0.010(4) C44 0.119(10) 0.114(9) 0.074(8) 0.031(7) 0.017(7) 0.026(8) C45 0.044(5) 0.048(5) 0.116(8) 0.007(5) -0.011(5) 0.002(4) _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 Br1 C1 1.872(6) . ? N1 C1 1.320(7) . ? N1 C4 1.431(8) . ? N1 C2 1.483(8) . ? C1 N2 1.309(8) . ? Cl1 C43 1.737(8) . ? N2 C13 1.444(7) . ? N2 C3 1.483(7) . ? C2 C3 1.519(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? Cl2 C43 1.763(8) . ? Br3 C22 1.868(6) . ? N3 C22 1.304(7) . ? N3 C34 1.447(7) . ? N3 C23 1.494(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? Cl3 C43 1.775(8) . ? N4 C22 1.305(8) . ? N4 C25 1.435(7) . ? N4 C24 1.491(7) . ? C4 C9 1.383(9) . ? C4 C5 1.399(9) . ? Cl4 C44 1.792(13) . ? C5 C6 1.387(10) . ? C5 C12 1.507(10) . ? Cl5 C44 1.675(12) . ? C6 C7 1.376(11) . ? C6 H6A 0.9300 . ? Cl6 C44 1.699(12) . ? C7 C8 1.384(10) . ? C7 C11 1.506(10) . ? Cl7 C45 1.759(10) . ? C8 C9 1.406(9) . ? C8 H8A 0.9300 . ? Cl8 C45 1.712(9) . ? C9 C10 1.497(9) . ? Cl9 C45 1.719(9) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.379(9) . ? C13 C18 1.399(9) . ? C14 C15 1.396(9) . ? C14 C21 1.512(9) . ? C15 C16 1.388(9) . ? C15 H15A 0.9300 . ? C16 C17 1.376(9) . ? C16 C20 1.512(9) . ? C17 C18 1.389(9) . ? C17 H17A 0.9300 . ? C18 C19 1.510(9) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C23 C24 1.535(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C30 1.387(8) . ? C25 C26 1.406(8) . ? C26 C27 1.383(9) . ? C26 C33 1.511(9) . ? C27 C28 1.387(10) . ? C27 H27A 0.9300 . ? C28 C29 1.380(9) . ? C28 C32 1.504(9) . ? C29 C30 1.381(9) . ? C29 H29A 0.9300 . ? C30 C31 1.500(9) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C39 1.393(9) . ? C34 C35 1.394(9) . ? C35 C36 1.404(9) . ? C35 C42 1.507(10) . ? C36 C37 1.367(11) . ? C36 H36A 0.9300 . ? C37 C38 1.368(11) . ? C37 C41 1.519(10) . ? C38 C39 1.406(9) . ? C38 H38A 0.9300 . ? C39 C40 1.498(9) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 H43A 0.9800 . ? C44 H44A 0.9800 . ? C45 H45A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 127.9(5) . . ? C1 N1 C2 108.8(5) . . ? C4 N1 C2 122.6(5) . . ? N2 C1 N1 114.4(5) . . ? N2 C1 Br1 123.8(4) . . ? N1 C1 Br1 121.8(5) . . ? C1 N2 C13 127.9(5) . . ? C1 N2 C3 109.7(5) . . ? C13 N2 C3 121.2(5) . . ? N1 C2 C3 103.9(5) . . ? N1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? N1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C22 N3 C34 128.0(5) . . ? C22 N3 C23 110.0(5) . . ? C34 N3 C23 121.9(5) . . ? N2 C3 C2 102.9(5) . . ? N2 C3 H3A 111.2 . . ? C2 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? C22 N4 C25 126.4(5) . . ? C22 N4 C24 110.3(5) . . ? C25 N4 C24 123.3(5) . . ? C9 C4 C5 122.8(6) . . ? C9 C4 N1 119.1(6) . . ? C5 C4 N1 117.9(6) . . ? C6 C5 C4 116.8(7) . . ? C6 C5 C12 121.5(7) . . ? C4 C5 C12 121.6(6) . . ? C7 C6 C5 123.0(7) . . ? C7 C6 H6A 118.5 . . ? C5 C6 H6A 118.5 . . ? C6 C7 C8 118.3(7) . . ? C6 C7 C11 120.8(8) . . ? C8 C7 C11 120.9(8) . . ? C7 C8 C9 121.8(7) . . ? C7 C8 H8A 119.1 . . ? C9 C8 H8A 119.1 . . ? C4 C9 C8 117.3(6) . . ? C4 C9 C10 122.6(6) . . ? C8 C9 C10 120.1(6) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 122.3(6) . . ? C14 C13 N2 118.8(5) . . ? C18 C13 N2 118.6(5) . . ? C13 C14 C15 118.1(6) . . ? C13 C14 C21 122.2(6) . . ? C15 C14 C21 119.7(6) . . ? C16 C15 C14 121.4(6) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C17 C16 C15 118.5(6) . . ? C17 C16 C20 121.6(6) . . ? C15 C16 C20 119.9(6) . . ? C16 C17 C18 122.5(6) . . ? C16 C17 H17A 118.8 . . ? C18 C17 H17A 118.8 . . ? C17 C18 C13 117.2(6) . . ? C17 C18 C19 120.5(6) . . ? C13 C18 C19 122.3(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 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 N4 114.3(5) . . ? N3 C22 Br3 122.7(5) . . ? N4 C22 Br3 123.0(4) . . ? N3 C23 C24 102.8(4) . . ? N3 C23 H23A 111.2 . . ? C24 C23 H23A 111.2 . . ? N3 C23 H23B 111.2 . . ? C24 C23 H23B 111.2 . . ? H23A C23 H23B 109.1 . . ? N4 C24 C23 102.5(4) . . ? N4 C24 H24A 111.3 . . ? C23 C24 H24A 111.3 . . ? N4 C24 H24B 111.3 . . ? C23 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? C30 C25 C26 122.9(5) . . ? C30 C25 N4 119.1(5) . . ? C26 C25 N4 117.9(5) . . ? C27 C26 C25 116.8(6) . . ? C27 C26 C33 121.4(6) . . ? C25 C26 C33 121.7(6) . . ? C26 C27 C28 122.2(6) . . ? C26 C27 H27A 118.9 . . ? C28 C27 H27A 118.9 . . ? C29 C28 C27 118.4(6) . . ? C29 C28 C32 121.5(7) . . ? C27 C28 C32 120.1(7) . . ? C28 C29 C30 122.6(6) . . ? C28 C29 H29A 118.7 . . ? C30 C29 H29A 118.7 . . ? C29 C30 C25 117.1(6) . . ? C29 C30 C31 121.4(6) . . ? C25 C30 C31 121.5(6) . . ? 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 . . ? C28 C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C28 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C26 C33 H33A 109.5 . . ? C26 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C26 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C39 C34 C35 123.7(6) . . ? C39 C34 N3 118.0(5) . . ? C35 C34 N3 118.2(6) . . ? C34 C35 C36 116.4(6) . . ? C34 C35 C42 121.7(6) . . ? C36 C35 C42 122.0(6) . . ? C37 C36 C35 122.0(7) . . ? C37 C36 H36A 119.0 . . ? C35 C36 H36A 119.0 . . ? C36 C37 C38 119.6(7) . . ? C36 C37 C41 120.3(8) . . ? C38 C37 C41 120.1(8) . . ? C37 C38 C39 122.1(7) . . ? C37 C38 H38A 119.0 . . ? C39 C38 H38A 119.0 . . ? C34 C39 C38 116.2(6) . . ? C34 C39 C40 121.7(6) . . ? C38 C39 C40 122.1(6) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C37 C41 H41A 109.5 . . ? C37 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C37 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C35 C42 H42A 109.5 . . ? C35 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C35 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? Cl1 C43 Cl2 112.1(4) . . ? Cl1 C43 Cl3 109.9(4) . . ? Cl2 C43 Cl3 108.9(4) . . ? Cl1 C43 H43A 108.6 . . ? Cl2 C43 H43A 108.6 . . ? Cl3 C43 H43A 108.6 . . ? Cl5 C44 Cl6 113.9(7) . . ? Cl5 C44 Cl4 107.9(6) . . ? Cl6 C44 Cl4 108.2(8) . . ? Cl5 C44 H44A 108.9 . . ? Cl6 C44 H44A 108.9 . . ? Cl4 C44 H44A 108.9 . . ? Cl8 C45 Cl9 114.9(6) . . ? Cl8 C45 Cl7 109.6(5) . . ? Cl9 C45 Cl7 110.1(5) . . ? Cl8 C45 H45A 107.3 . . ? Cl9 C45 H45A 107.3 . . ? Cl7 C45 H45A 107.3 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.590 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.108 data_DACUrea _database_code_depnum_ccdc_archive 'CCDC 882673' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DACUrea _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O3' _chemical_formula_sum 'C24 H28 N2 O3' _chemical_formula_weight 392.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.005(6) _cell_length_b 8.772(6) _cell_length_c 16.048(11) _cell_angle_alpha 91.431(9) _cell_angle_beta 103.924(9) _cell_angle_gamma 98.836(7) _cell_volume 1078.6(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15923 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3779 _reflns_number_gt 2980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1174P)^2^+0.5338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3779 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7749(2) 0.2291(2) 0.34031(11) 0.0234(4) Uani 1 1 d . . . O1 O 1.0679(2) 0.2558(2) 0.38997(10) 0.0378(5) Uani 1 1 d . . . C1 C 0.6245(3) 0.2257(2) 0.27492(13) 0.0233(5) Uani 1 1 d . . . N2 N 0.6454(2) 0.2463(2) 0.19157(11) 0.0237(4) Uani 1 1 d . . . O2 O 0.8076(2) 0.2757(2) 0.09381(10) 0.0397(5) Uani 1 1 d . . . C2 C 0.9441(3) 0.2462(2) 0.32872(14) 0.0253(5) Uani 1 1 d . . . O3 O 0.4809(2) 0.2081(2) 0.28900(10) 0.0336(4) Uani 1 1 d . . . C3 C 0.9662(3) 0.2470(3) 0.23759(14) 0.0268(5) Uani 1 1 d . . . C4 C 0.8028(3) 0.2588(3) 0.16817(14) 0.0274(5) Uani 1 1 d . . . C5 C 1.1082(3) 0.3831(3) 0.23264(17) 0.0407(6) Uani 1 1 d . . . H5A H 1.0718 0.4784 0.2455 0.061 Uiso 1 1 calc R . . H5B H 1.1268 0.3827 0.1757 0.061 Uiso 1 1 calc R . . H5C H 1.2148 0.3734 0.2735 0.061 Uiso 1 1 calc R . . C6 C 1.0253(4) 0.0940(3) 0.21813(17) 0.0424(7) Uani 1 1 d . . . H6A H 0.9364 0.0090 0.2214 0.064 Uiso 1 1 calc R . . H6B H 1.1315 0.0850 0.2595 0.064 Uiso 1 1 calc R . . H6C H 1.0447 0.0926 0.1614 0.064 Uiso 1 1 calc R . . C7 C 0.4890(3) 0.2564(3) 0.12483(13) 0.0243(5) Uani 1 1 d . . . C8 C 0.4464(3) 0.4020(3) 0.10570(14) 0.0277(5) Uani 1 1 d . . . C9 C 0.2981(3) 0.4092(3) 0.04031(15) 0.0312(5) Uani 1 1 d . . . H9A H 0.2687 0.5052 0.0257 0.037 Uiso 1 1 calc R . . C10 C 0.1927(3) 0.2762(3) -0.00374(14) 0.0306(5) Uani 1 1 d . . . C11 C 0.2397(3) 0.1337(3) 0.01785(14) 0.0287(5) Uani 1 1 d . . . H11A H 0.1695 0.0445 -0.0111 0.034 Uiso 1 1 calc R . . C12 C 0.3888(3) 0.1200(3) 0.08157(14) 0.0255(5) Uani 1 1 d . . . C13 C 0.4384(3) -0.0357(3) 0.10308(15) 0.0321(5) Uani 1 1 d . . . H13A H 0.3702 -0.1124 0.0594 0.048 Uiso 1 1 calc R . . H13B H 0.4167 -0.0614 0.1577 0.048 Uiso 1 1 calc R . . H13C H 0.5601 -0.0324 0.1058 0.048 Uiso 1 1 calc R . . C14 C 0.0299(3) 0.2884(4) -0.07237(17) 0.0429(7) Uani 1 1 d . . . H14A H 0.0352 0.2389 -0.1255 0.064 Uiso 1 1 calc R . . H14B H 0.0216 0.3954 -0.0802 0.064 Uiso 1 1 calc R . . H14C H -0.0707 0.2387 -0.0550 0.064 Uiso 1 1 calc R . . C15 C 0.5549(4) 0.5468(3) 0.15471(16) 0.0381(6) Uani 1 1 d . . . H15A H 0.6747 0.5495 0.1538 0.057 Uiso 1 1 calc R . . H15B H 0.5452 0.5476 0.2132 0.057 Uiso 1 1 calc R . . H15C H 0.5139 0.6357 0.1284 0.057 Uiso 1 1 calc R . . C16 C 0.7536(3) 0.2211(2) 0.42784(13) 0.0237(5) Uani 1 1 d . . . C17 C 0.7360(3) 0.3558(3) 0.47034(14) 0.0281(5) Uani 1 1 d . . . C18 C 0.7145(3) 0.3458(3) 0.55374(15) 0.0315(5) Uani 1 1 d . . . H18A H 0.7033 0.4345 0.5835 0.038 Uiso 1 1 calc R . . C19 C 0.7094(3) 0.2065(3) 0.59376(14) 0.0299(5) Uani 1 1 d . . . C20 C 0.7263(3) 0.0750(3) 0.54866(15) 0.0302(5) Uani 1 1 d . . . H20A H 0.7218 -0.0185 0.5747 0.036 Uiso 1 1 calc R . . C21 C 0.7497(3) 0.0791(2) 0.46533(14) 0.0262(5) Uani 1 1 d . . . C22 C 0.7722(4) -0.0647(3) 0.41876(16) 0.0374(6) Uani 1 1 d . . . H22A H 0.7415 -0.1534 0.4492 0.056 Uiso 1 1 calc R . . H22B H 0.8916 -0.0574 0.4159 0.056 Uiso 1 1 calc R . . H22C H 0.6979 -0.0750 0.3615 0.056 Uiso 1 1 calc R . . C23 C 0.6876(4) 0.1993(3) 0.68473(16) 0.0405(6) Uani 1 1 d . . . H23A H 0.6357 0.0966 0.6932 0.061 Uiso 1 1 calc R . . H23B H 0.6136 0.2711 0.6940 0.061 Uiso 1 1 calc R . . H23C H 0.7997 0.2258 0.7247 0.061 Uiso 1 1 calc R . . C24 C 0.7417(4) 0.5083(3) 0.42848(17) 0.0425(7) Uani 1 1 d . . . H24A H 0.7357 0.5885 0.4689 0.064 Uiso 1 1 calc R . . H24B H 0.6444 0.5014 0.3792 0.064 Uiso 1 1 calc R . . H24C H 0.8485 0.5317 0.4107 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0243(10) 0.0274(9) 0.0189(9) 0.0028(7) 0.0052(7) 0.0052(7) O1 0.0250(9) 0.0602(12) 0.0251(9) 0.0045(8) 0.0001(7) 0.0063(8) C1 0.0235(11) 0.0254(11) 0.0210(11) 0.0023(8) 0.0052(9) 0.0050(9) N2 0.0208(9) 0.0307(10) 0.0194(9) 0.0031(7) 0.0039(7) 0.0047(7) O2 0.0298(9) 0.0691(13) 0.0227(9) 0.0090(8) 0.0088(7) 0.0108(8) C2 0.0235(11) 0.0274(11) 0.0249(12) 0.0030(9) 0.0053(9) 0.0043(9) O3 0.0240(9) 0.0510(11) 0.0270(9) 0.0072(7) 0.0086(7) 0.0061(7) C3 0.0221(11) 0.0355(12) 0.0235(11) 0.0023(9) 0.0057(9) 0.0070(9) C4 0.0242(12) 0.0335(12) 0.0252(12) 0.0029(9) 0.0066(9) 0.0057(9) C5 0.0287(13) 0.0560(17) 0.0330(13) 0.0071(12) 0.0050(11) -0.0031(12) C6 0.0441(15) 0.0519(16) 0.0334(14) -0.0029(12) 0.0058(12) 0.0218(13) C7 0.0198(10) 0.0349(12) 0.0193(10) 0.0050(9) 0.0046(9) 0.0076(9) C8 0.0293(12) 0.0341(12) 0.0234(11) 0.0057(9) 0.0110(10) 0.0085(10) C9 0.0319(12) 0.0392(13) 0.0280(12) 0.0109(10) 0.0113(10) 0.0156(10) C10 0.0247(12) 0.0492(14) 0.0205(11) 0.0083(10) 0.0073(9) 0.0103(10) C11 0.0234(11) 0.0389(13) 0.0225(11) 0.0022(9) 0.0047(9) 0.0025(9) C12 0.0240(11) 0.0327(12) 0.0208(11) 0.0028(9) 0.0081(9) 0.0034(9) C13 0.0334(13) 0.0329(12) 0.0286(12) 0.0035(10) 0.0051(10) 0.0049(10) C14 0.0305(13) 0.0626(18) 0.0349(14) 0.0119(13) 0.0026(11) 0.0135(12) C15 0.0457(15) 0.0329(13) 0.0359(14) 0.0024(11) 0.0092(12) 0.0087(11) C16 0.0212(10) 0.0295(11) 0.0193(11) 0.0034(9) 0.0033(8) 0.0035(9) C17 0.0331(12) 0.0264(11) 0.0239(11) 0.0032(9) 0.0046(9) 0.0059(9) C18 0.0371(13) 0.0326(13) 0.0254(12) -0.0004(10) 0.0066(10) 0.0092(10) C19 0.0282(12) 0.0384(13) 0.0218(11) 0.0046(10) 0.0044(9) 0.0034(10) C20 0.0323(12) 0.0294(12) 0.0273(12) 0.0087(10) 0.0049(10) 0.0034(10) C21 0.0254(11) 0.0262(11) 0.0248(11) 0.0028(9) 0.0013(9) 0.0049(9) C22 0.0490(15) 0.0301(13) 0.0332(13) 0.0038(10) 0.0080(12) 0.0103(11) C23 0.0466(15) 0.0496(15) 0.0260(13) 0.0052(11) 0.0114(11) 0.0060(12) C24 0.0700(19) 0.0283(13) 0.0307(13) 0.0036(10) 0.0132(13) 0.0111(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.389(3) . ? N1 C2 1.397(3) . ? N1 C16 1.457(3) . ? O1 C2 1.207(3) . ? C1 O3 1.212(3) . ? C1 N2 1.400(3) . ? N2 C4 1.388(3) . ? N2 C7 1.454(3) . ? O2 C4 1.215(3) . ? C2 C3 1.515(3) . ? C3 C4 1.519(3) . ? C3 C5 1.535(3) . ? C3 C6 1.539(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.395(3) . ? C7 C12 1.397(3) . ? C8 C9 1.393(3) . ? C8 C15 1.507(3) . ? C9 C10 1.393(4) . ? C9 H9A 0.9300 . ? C10 C11 1.388(3) . ? C10 C14 1.510(3) . ? C11 C12 1.396(3) . ? C11 H11A 0.9300 . ? C12 C13 1.505(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.392(3) . ? C16 C21 1.396(3) . ? C17 C18 1.393(3) . ? C17 C24 1.511(3) . ? C18 C19 1.394(3) . ? C18 H18A 0.9300 . ? C19 C20 1.388(3) . ? C19 C23 1.513(3) . ? C20 C21 1.395(3) . ? C20 H20A 0.9300 . ? C21 C22 1.507(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C1 N1 C2 125.00(18) . . ? C1 N1 C16 116.95(17) . . ? C2 N1 C16 117.98(17) . . ? O3 C1 N1 121.85(19) . . ? O3 C1 N2 120.91(19) . . ? N1 C1 N2 117.23(18) . . ? C4 N2 C1 125.21(18) . . ? C4 N2 C7 117.94(18) . . ? C1 N2 C7 116.85(17) . . ? O1 C2 N1 120.4(2) . . ? O1 C2 C3 121.5(2) . . ? N1 C2 C3 118.11(18) . . ? C2 C3 C4 115.42(18) . . ? C2 C3 C5 108.52(19) . . ? C4 C3 C5 108.50(19) . . ? C2 C3 C6 107.42(19) . . ? C4 C3 C6 107.28(19) . . ? C5 C3 C6 109.6(2) . . ? O2 C4 N2 120.4(2) . . ? O2 C4 C3 121.5(2) . . ? N2 C4 C3 118.08(19) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 122.6(2) . . ? C8 C7 N2 118.7(2) . . ? C12 C7 N2 118.72(19) . . ? C9 C8 C7 117.7(2) . . ? C9 C8 C15 120.9(2) . . ? C7 C8 C15 121.4(2) . . ? C10 C9 C8 121.7(2) . . ? C10 C9 H9A 119.1 . . ? C8 C9 H9A 119.1 . . ? C11 C10 C9 118.5(2) . . ? C11 C10 C14 121.3(2) . . ? C9 C10 C14 120.2(2) . . ? C10 C11 C12 122.2(2) . . ? C10 C11 H11A 118.9 . . ? C12 C11 H11A 118.9 . . ? C11 C12 C7 117.3(2) . . ? C11 C12 C13 121.2(2) . . ? C7 C12 C13 121.5(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 122.7(2) . . ? C17 C16 N1 118.39(19) . . ? C21 C16 N1 118.95(19) . . ? C16 C17 C18 117.6(2) . . ? C16 C17 C24 121.6(2) . . ? C18 C17 C24 120.8(2) . . ? C17 C18 C19 121.8(2) . . ? C17 C18 H18A 119.1 . . ? C19 C18 H18A 119.1 . . ? C20 C19 C18 118.6(2) . . ? C20 C19 C23 120.8(2) . . ? C18 C19 C23 120.6(2) . . ? C19 C20 C21 121.9(2) . . ? C19 C20 H20A 119.1 . . ? C21 C20 H20A 119.1 . . ? C20 C21 C16 117.5(2) . . ? C20 C21 C22 120.7(2) . . ? C16 C21 C22 121.8(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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 H24A 109.5 . . ? C17 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.563 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.210 data_DACDimethyldisulfide _database_code_depnum_ccdc_archive 'CCDC 882674' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DACDimethyldisulfide _chemical_melting_point ? _chemical_formula_moiety 'C26 H34 N2 O2 S2' _chemical_formula_sum 'C26 H34 N2 O2 S2' _chemical_formula_weight 470.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9337(12) _cell_length_b 11.8693(9) _cell_length_c 13.6108(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.054(2) _cell_angle_gamma 90.00 _cell_volume 2411.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colorless _exptl_crystal_colour plates _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12521 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4239 _reflns_number_gt 3593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+4.1729P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4239 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.33434(5) 0.40149(6) 0.01283(5) 0.0208(2) Uani 1 1 d . . . C1 C 0.30279(17) 0.4350(2) 0.1412(2) 0.0158(6) Uani 1 1 d . . . N1 N 0.20486(14) 0.44623(18) 0.15369(16) 0.0147(5) Uani 1 1 d . . . O1 O 0.06862(13) 0.36762(17) 0.16842(16) 0.0254(5) Uani 1 1 d . . . S2 S 0.35126(5) 0.56972(6) 0.18131(5) 0.0198(2) Uani 1 1 d . . . O2 O 0.32316(14) 0.15661(18) 0.24952(17) 0.0305(5) Uani 1 1 d . . . N2 N 0.33677(14) 0.33691(19) 0.19916(16) 0.0162(5) Uani 1 1 d . . . C2 C 0.14965(18) 0.3557(2) 0.16595(19) 0.0172(6) Uani 1 1 d . . . C3 C 0.19082(18) 0.2384(2) 0.1750(2) 0.0177(6) Uani 1 1 d . . . C4 C 0.28898(18) 0.2394(2) 0.2102(2) 0.0191(6) Uani 1 1 d . . . C5 C 0.1820(2) 0.1813(3) 0.0731(2) 0.0265(7) Uani 1 1 d . . . H5A H 0.2062 0.1064 0.0772 0.040 Uiso 1 1 calc R . . H5B H 0.2143 0.2243 0.0263 0.040 Uiso 1 1 calc R . . H5C H 0.1199 0.1777 0.0524 0.040 Uiso 1 1 calc R . . C6 C 0.1381(2) 0.1702(3) 0.2490(3) 0.0292(7) Uani 1 1 d . . . H6A H 0.1426 0.2061 0.3122 0.044 Uiso 1 1 calc R . . H6B H 0.1622 0.0954 0.2539 0.044 Uiso 1 1 calc R . . H6C H 0.0763 0.1665 0.2273 0.044 Uiso 1 1 calc R . . C7 C 0.15943(17) 0.5550(2) 0.1396(2) 0.0158(6) Uani 1 1 d . . . C8 C 0.14573(17) 0.6235(2) 0.2208(2) 0.0180(6) Uani 1 1 d . . . C9 C 0.10547(18) 0.7283(2) 0.2058(2) 0.0199(6) Uani 1 1 d . . . H9A H 0.0980 0.7755 0.2594 0.024 Uiso 1 1 calc R . . C10 C 0.07619(18) 0.7640(2) 0.1133(2) 0.0214(6) Uani 1 1 d . . . C11 C 0.08320(18) 0.6898(2) 0.0354(2) 0.0210(6) Uani 1 1 d . . . H11A H 0.0611 0.7117 -0.0265 0.025 Uiso 1 1 calc R . . C12 C 0.12240(17) 0.5829(2) 0.0464(2) 0.0176(6) Uani 1 1 d . . . C13 C 0.1160(2) 0.5016(3) -0.0381(2) 0.0257(7) Uani 1 1 d . . . H13A H 0.1593 0.4427 -0.0279 0.039 Uiso 1 1 calc R . . H13B H 0.1276 0.5406 -0.0981 0.039 Uiso 1 1 calc R . . H13C H 0.0570 0.4696 -0.0424 0.039 Uiso 1 1 calc R . . C14 C 0.0368(2) 0.8802(3) 0.0991(3) 0.0300(7) Uani 1 1 d . . . H14A H 0.0013 0.8821 0.0389 0.045 Uiso 1 1 calc R . . H14B H 0.0844 0.9344 0.0960 0.045 Uiso 1 1 calc R . . H14C H -0.0001 0.8978 0.1532 0.045 Uiso 1 1 calc R . . C15 C 0.1704(2) 0.5882(3) 0.3252(2) 0.0245(7) Uani 1 1 d . . . H15A H 0.1719 0.5074 0.3291 0.037 Uiso 1 1 calc R . . H15B H 0.1267 0.6168 0.3687 0.037 Uiso 1 1 calc R . . H15C H 0.2283 0.6179 0.3439 0.037 Uiso 1 1 calc R . . C16 C 0.42715(18) 0.3396(2) 0.2429(2) 0.0159(6) Uani 1 1 d . . . C17 C 0.43851(19) 0.3855(2) 0.3374(2) 0.0182(6) Uani 1 1 d . . . C18 C 0.52546(19) 0.3978(2) 0.3763(2) 0.0196(6) Uani 1 1 d . . . H18A H 0.5338 0.4302 0.4382 0.023 Uiso 1 1 calc R . . C19 C 0.60020(18) 0.3636(2) 0.3262(2) 0.0209(6) Uani 1 1 d . . . C20 C 0.58563(19) 0.3099(2) 0.2368(2) 0.0213(6) Uani 1 1 d . . . H20A H 0.6347 0.2834 0.2035 0.026 Uiso 1 1 calc R . . C21 C 0.50005(19) 0.2941(2) 0.1947(2) 0.0189(6) Uani 1 1 d . . . C22 C 0.4906(2) 0.2236(3) 0.1030(2) 0.0261(7) Uani 1 1 d . . . H22A H 0.4335 0.1862 0.1013 0.039 Uiso 1 1 calc R . . H22B H 0.5376 0.1684 0.1029 0.039 Uiso 1 1 calc R . . H22C H 0.4946 0.2711 0.0463 0.039 Uiso 1 1 calc R . . C23 C 0.6937(2) 0.3806(3) 0.3691(3) 0.0304(7) Uani 1 1 d . . . H23A H 0.6907 0.4062 0.4358 0.046 Uiso 1 1 calc R . . H23B H 0.7242 0.4358 0.3310 0.046 Uiso 1 1 calc R . . H23C H 0.7259 0.3106 0.3677 0.046 Uiso 1 1 calc R . . C24 C 0.3606(2) 0.4175(3) 0.3978(2) 0.0248(7) Uani 1 1 d . . . H24A H 0.3089 0.3746 0.3766 0.037 Uiso 1 1 calc R . . H24B H 0.3483 0.4964 0.3897 0.037 Uiso 1 1 calc R . . H24C H 0.3747 0.4019 0.4658 0.037 Uiso 1 1 calc R . . C25 C 0.3293(2) 0.5340(3) -0.0525(2) 0.0268(7) Uani 1 1 d . . . H25A H 0.3236 0.5200 -0.1219 0.040 Uiso 1 1 calc R . . H25B H 0.3832 0.5761 -0.0382 0.040 Uiso 1 1 calc R . . H25C H 0.2785 0.5765 -0.0320 0.040 Uiso 1 1 calc R . . C26 C 0.46755(19) 0.5661(3) 0.1465(2) 0.0232(6) Uani 1 1 d . . . H26A H 0.4864 0.6406 0.1293 0.035 Uiso 1 1 calc R . . H26B H 0.4734 0.5168 0.0912 0.035 Uiso 1 1 calc R . . H26C H 0.5043 0.5389 0.2007 0.035 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 S1 0.0228(4) 0.0213(4) 0.0186(4) -0.0007(3) 0.0039(3) 0.0014(3) C1 0.0146(13) 0.0148(13) 0.0180(14) 0.0013(11) 0.0008(10) 0.0018(10) N1 0.0136(11) 0.0135(11) 0.0170(11) 0.0019(9) 0.0006(9) 0.0026(9) O1 0.0169(10) 0.0217(11) 0.0377(12) 0.0071(10) 0.0023(9) -0.0005(8) S2 0.0193(4) 0.0171(4) 0.0231(4) -0.0013(3) 0.0037(3) -0.0007(3) O2 0.0277(11) 0.0181(11) 0.0449(14) 0.0119(10) -0.0094(10) -0.0019(9) N2 0.0150(11) 0.0151(11) 0.0184(12) 0.0019(10) -0.0018(9) -0.0013(9) C2 0.0187(14) 0.0176(14) 0.0153(13) 0.0023(11) 0.0008(10) 0.0001(11) C3 0.0167(13) 0.0137(13) 0.0226(14) 0.0009(11) -0.0012(11) -0.0020(11) C4 0.0213(14) 0.0155(14) 0.0204(14) 0.0018(12) -0.0020(11) 0.0000(11) C5 0.0258(15) 0.0244(16) 0.0290(16) -0.0065(13) -0.0036(12) -0.0006(13) C6 0.0269(16) 0.0217(15) 0.0393(18) 0.0116(14) 0.0072(14) -0.0001(13) C7 0.0118(12) 0.0147(13) 0.0211(14) 0.0019(11) 0.0034(10) 0.0002(10) C8 0.0144(13) 0.0179(14) 0.0219(14) -0.0011(12) 0.0042(11) -0.0007(11) C9 0.0159(13) 0.0181(14) 0.0262(15) -0.0048(12) 0.0052(11) 0.0000(11) C10 0.0134(13) 0.0152(14) 0.0358(17) 0.0026(13) 0.0038(12) 0.0000(11) C11 0.0171(13) 0.0227(15) 0.0233(15) 0.0070(12) 0.0002(11) 0.0013(11) C12 0.0129(13) 0.0188(14) 0.0211(14) 0.0023(12) 0.0018(11) 0.0004(11) C13 0.0272(15) 0.0272(16) 0.0225(15) -0.0031(13) -0.0035(12) 0.0077(13) C14 0.0298(17) 0.0175(15) 0.0424(19) 0.0012(14) -0.0032(14) 0.0042(13) C15 0.0274(15) 0.0288(16) 0.0177(14) -0.0032(13) 0.0040(12) 0.0077(13) C16 0.0180(13) 0.0125(13) 0.0169(13) 0.0047(11) -0.0016(10) 0.0002(10) C17 0.0218(14) 0.0141(13) 0.0187(14) 0.0032(11) -0.0006(11) 0.0006(11) C18 0.0217(14) 0.0166(14) 0.0201(14) 0.0004(12) -0.0029(11) 0.0004(11) C19 0.0185(14) 0.0154(14) 0.0286(16) 0.0037(12) -0.0019(12) 0.0004(11) C20 0.0192(14) 0.0175(14) 0.0275(15) 0.0035(12) 0.0037(12) 0.0059(11) C21 0.0220(14) 0.0130(13) 0.0217(14) 0.0028(12) 0.0022(11) 0.0014(11) C22 0.0303(16) 0.0225(15) 0.0254(15) -0.0033(13) -0.0008(13) 0.0070(13) C23 0.0195(15) 0.0293(17) 0.0422(19) -0.0042(15) -0.0030(13) 0.0007(13) C24 0.0231(15) 0.0336(17) 0.0178(14) -0.0010(13) 0.0003(12) 0.0020(13) C25 0.0298(16) 0.0277(16) 0.0231(15) 0.0043(13) 0.0045(12) 0.0011(13) C26 0.0206(14) 0.0241(15) 0.0251(15) -0.0006(13) 0.0034(12) -0.0025(12) _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 S1 C25 1.807(3) . ? S1 C1 1.868(3) . ? C1 N1 1.484(3) . ? C1 N2 1.486(3) . ? C1 S2 1.831(3) . ? N1 C2 1.369(4) . ? N1 C7 1.467(3) . ? O1 C2 1.220(3) . ? S2 C26 1.817(3) . ? O2 C4 1.222(3) . ? N2 C4 1.370(4) . ? N2 C16 1.456(3) . ? C2 C3 1.525(4) . ? C3 C4 1.526(4) . ? C3 C6 1.531(4) . ? C3 C5 1.545(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.393(4) . ? C7 C12 1.406(4) . ? C8 C9 1.393(4) . ? C8 C15 1.514(4) . ? C9 C10 1.384(4) . ? C9 H9A 0.9300 . ? C10 C11 1.386(4) . ? C10 C14 1.508(4) . ? C11 C12 1.403(4) . ? C11 H11A 0.9300 . ? C12 C13 1.502(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C21 1.399(4) . ? C16 C17 1.402(4) . ? C17 C18 1.392(4) . ? C17 C24 1.497(4) . ? C18 C19 1.389(4) . ? C18 H18A 0.9300 . ? C19 C20 1.384(4) . ? C19 C23 1.508(4) . ? C20 C21 1.394(4) . ? C20 H20A 0.9300 . ? C21 C22 1.505(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C25 S1 C1 105.48(13) . . ? N1 C1 N2 109.2(2) . . ? N1 C1 S2 105.54(17) . . ? N2 C1 S2 113.70(18) . . ? N1 C1 S1 114.14(18) . . ? N2 C1 S1 103.72(17) . . ? S2 C1 S1 110.79(14) . . ? C2 N1 C7 115.4(2) . . ? C2 N1 C1 122.9(2) . . ? C7 N1 C1 121.1(2) . . ? C26 S2 C1 105.83(13) . . ? C4 N2 C16 116.9(2) . . ? C4 N2 C1 123.4(2) . . ? C16 N2 C1 119.6(2) . . ? O1 C2 N1 120.9(3) . . ? O1 C2 C3 120.1(2) . . ? N1 C2 C3 118.9(2) . . ? C2 C3 C4 113.5(2) . . ? C2 C3 C6 108.7(2) . . ? C4 C3 C6 108.0(2) . . ? C2 C3 C5 107.8(2) . . ? C4 C3 C5 109.6(2) . . ? C6 C3 C5 109.2(2) . . ? O2 C4 N2 121.1(3) . . ? O2 C4 C3 120.8(3) . . ? N2 C4 C3 118.1(2) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 120.9(2) . . ? C8 C7 N1 119.4(2) . . ? C12 C7 N1 119.4(2) . . ? C9 C8 C7 118.7(3) . . ? C9 C8 C15 118.3(2) . . ? C7 C8 C15 123.0(2) . . ? C10 C9 C8 121.8(3) . . ? C10 C9 H9A 119.1 . . ? C8 C9 H9A 119.1 . . ? C9 C10 C11 118.1(3) . . ? C9 C10 C14 120.4(3) . . ? C11 C10 C14 121.5(3) . . ? C10 C11 C12 122.4(3) . . ? C10 C11 H11A 118.8 . . ? C12 C11 H11A 118.8 . . ? C11 C12 C7 117.3(3) . . ? C11 C12 C13 119.0(2) . . ? C7 C12 C13 123.5(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 120.6(2) . . ? C21 C16 N2 121.7(2) . . ? C17 C16 N2 117.6(2) . . ? C18 C17 C16 118.0(3) . . ? C18 C17 C24 119.8(3) . . ? C16 C17 C24 122.1(2) . . ? C19 C18 C17 122.5(3) . . ? C19 C18 H18A 118.7 . . ? C17 C18 H18A 118.7 . . ? C20 C19 C18 117.5(3) . . ? C20 C19 C23 121.1(3) . . ? C18 C19 C23 121.4(3) . . ? C19 C20 C21 122.4(3) . . ? C19 C20 H20A 118.8 . . ? C21 C20 H20A 118.8 . . ? C20 C21 C16 118.2(3) . . ? C20 C21 C22 118.2(3) . . ? C16 C21 C22 123.5(3) . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 H24A 109.5 . . ? C17 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? S1 C25 H25A 109.5 . . ? S1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S2 C26 H26A 109.5 . . ? S2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.411 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.076 data_'DACDiphenylsulfide' _database_code_depnum_ccdc_archive 'CCDC 882675' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DACDiphenylsulfide _chemical_melting_point ? _chemical_formula_moiety 'C36 H38 N2 O2 S2' _chemical_formula_sum 'C36 H38 N2 O2 S2' _chemical_formula_weight 594.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0307(15) _cell_length_b 12.1360(16) _cell_length_c 12.8498(17) _cell_angle_alpha 69.777(3) _cell_angle_beta 79.796(3) _cell_angle_gamma 85.828(3) _cell_volume 1588.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14027 _diffrn_reflns_av_R_equivalents 0.0928 _diffrn_reflns_av_sigmaI/netI 0.1125 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5586 _reflns_number_gt 3546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.8658P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5586 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.28273(8) 0.32250(9) 0.33427(8) 0.0285(3) Uani 1 1 d . . . N1 N 0.1282(2) 0.2819(2) 0.2152(2) 0.0207(7) Uani 1 1 d . . . C1 C 0.2505(3) 0.2546(3) 0.2376(3) 0.0194(8) Uani 1 1 d . . . O1 O -0.0439(2) 0.2670(2) 0.1507(2) 0.0381(7) Uani 1 1 d . . . S2 S 0.30804(9) 0.00283(9) 0.06464(8) 0.0342(3) Uani 1 1 d . . . O2 O 0.1337(2) 0.0049(2) 0.2355(2) 0.0301(6) Uani 1 1 d . . . N2 N 0.3195(2) 0.1905(2) 0.1931(2) 0.0206(7) Uani 1 1 d . . . C2 C 0.0638(3) 0.2406(3) 0.1499(3) 0.0249(8) Uani 1 1 d . . . C3 C 0.1279(3) 0.1755(3) 0.0716(3) 0.0235(8) Uani 1 1 d . . . C4 C 0.1832(3) 0.0587(3) 0.1422(3) 0.0260(8) Uani 1 1 d . . . C5 C 0.0288(3) 0.1367(3) 0.0214(3) 0.0341(10) Uani 1 1 d . . . H5A H -0.0281 0.0857 0.0810 0.051 Uiso 1 1 calc R . . H5B H 0.0673 0.0957 -0.0279 0.051 Uiso 1 1 calc R . . H5C H -0.0146 0.2046 -0.0201 0.051 Uiso 1 1 calc R . . C6 C 0.2172(3) 0.2583(3) -0.0246(3) 0.0319(9) Uani 1 1 d . . . H6A H 0.2796 0.2828 0.0059 0.048 Uiso 1 1 calc R . . H6B H 0.1727 0.3259 -0.0651 0.048 Uiso 1 1 calc R . . H6C H 0.2552 0.2179 -0.0746 0.048 Uiso 1 1 calc R . . C7 C 0.0531(3) 0.3576(3) 0.2688(3) 0.0211(8) Uani 1 1 d . . . C8 C -0.0164(3) 0.3083(3) 0.3756(3) 0.0263(8) Uani 1 1 d . . . C9 C -0.0850(3) 0.3855(3) 0.4227(3) 0.0306(9) Uani 1 1 d . . . H9A H -0.1310 0.3553 0.4942 0.037 Uiso 1 1 calc R . . C10 C -0.0868(3) 0.5062(4) 0.3666(3) 0.0324(9) Uani 1 1 d . . . C11 C -0.0175(3) 0.5498(3) 0.2612(3) 0.0315(9) Uani 1 1 d . . . H11A H -0.0183 0.6304 0.2232 0.038 Uiso 1 1 calc R . . C12 C 0.0538(3) 0.4778(3) 0.2094(3) 0.0234(8) Uani 1 1 d . . . C13 C 0.1312(3) 0.5275(3) 0.0950(3) 0.0339(10) Uani 1 1 d . . . H13A H 0.1059 0.4945 0.0443 0.051 Uiso 1 1 calc R . . H13B H 0.2163 0.5084 0.1005 0.051 Uiso 1 1 calc R . . H13C H 0.1205 0.6113 0.0671 0.051 Uiso 1 1 calc R . . C14 C -0.1655(4) 0.5867(4) 0.4189(4) 0.0523(12) Uani 1 1 d . . . H14A H -0.1585 0.6659 0.3674 0.078 Uiso 1 1 calc R . . H14B H -0.1380 0.5822 0.4871 0.078 Uiso 1 1 calc R . . H14C H -0.2499 0.5630 0.4354 0.078 Uiso 1 1 calc R . . C15 C -0.0173(4) 0.1783(3) 0.4376(3) 0.0380(10) Uani 1 1 d . . . H15A H -0.0359 0.1380 0.3901 0.057 Uiso 1 1 calc R . . H15B H -0.0786 0.1607 0.5040 0.057 Uiso 1 1 calc R . . H15C H 0.0622 0.1531 0.4585 0.057 Uiso 1 1 calc R . . C16 C 0.4341(3) 0.1415(3) 0.2231(3) 0.0192(8) Uani 1 1 d . . . C17 C 0.4382(3) 0.0512(3) 0.3250(3) 0.0244(8) Uani 1 1 d . . . C18 C 0.5526(3) 0.0003(3) 0.3467(3) 0.0276(9) Uani 1 1 d . . . H18A H 0.5562 -0.0600 0.4146 0.033 Uiso 1 1 calc R . . C19 C 0.6613(3) 0.0351(3) 0.2723(3) 0.0282(9) Uani 1 1 d . . . C20 C 0.6523(3) 0.1238(3) 0.1710(3) 0.0285(9) Uani 1 1 d . . . H20A H 0.7237 0.1485 0.1192 0.034 Uiso 1 1 calc R . . C21 C 0.5417(3) 0.1768(3) 0.1439(3) 0.0224(8) Uani 1 1 d . . . C22 C 0.5364(3) 0.2704(3) 0.0318(3) 0.0298(9) Uani 1 1 d . . . H22A H 0.6184 0.2957 -0.0046 0.045 Uiso 1 1 calc R . . H22B H 0.4883 0.3359 0.0425 0.045 Uiso 1 1 calc R . . H22C H 0.4992 0.2393 -0.0142 0.045 Uiso 1 1 calc R . . C23 C 0.7831(4) -0.0241(4) 0.2984(4) 0.0439(11) Uani 1 1 d . . . H23A H 0.7709 -0.0824 0.3721 0.066 Uiso 1 1 calc R . . H23B H 0.8400 0.0334 0.2956 0.066 Uiso 1 1 calc R . . H23C H 0.8157 -0.0609 0.2439 0.066 Uiso 1 1 calc R . . C24 C 0.3241(3) 0.0030(3) 0.4076(3) 0.0346(10) Uani 1 1 d . . . H24A H 0.2837 0.0637 0.4336 0.052 Uiso 1 1 calc R . . H24B H 0.3462 -0.0610 0.4702 0.052 Uiso 1 1 calc R . . H24C H 0.2694 -0.0244 0.3716 0.052 Uiso 1 1 calc R . . C25 C 0.4436(3) 0.3485(3) 0.2959(3) 0.0226(8) Uani 1 1 d . . . C26 C 0.5232(4) 0.2902(3) 0.3706(3) 0.0346(10) Uani 1 1 d . . . H26A H 0.4933 0.2335 0.4388 0.042 Uiso 1 1 calc R . . C27 C 0.6464(4) 0.3167(4) 0.3431(4) 0.0479(12) Uani 1 1 d . . . H27A H 0.6994 0.2780 0.3934 0.057 Uiso 1 1 calc R . . C28 C 0.6921(4) 0.3996(4) 0.2425(4) 0.0392(10) Uani 1 1 d . . . H28A H 0.7760 0.4149 0.2235 0.047 Uiso 1 1 calc R . . C29 C 0.6128(4) 0.4600(3) 0.1699(3) 0.0351(10) Uani 1 1 d . . . H29A H 0.6433 0.5172 0.1022 0.042 Uiso 1 1 calc R . . C30 C 0.4888(3) 0.4364(3) 0.1968(3) 0.0275(9) Uani 1 1 d . . . H30A H 0.4354 0.4794 0.1485 0.033 Uiso 1 1 calc R . . C31 C 0.3371(4) -0.1336(3) 0.1664(3) 0.0306(9) Uani 1 1 d . . . C32 C 0.4505(4) -0.1514(3) 0.2031(3) 0.0370(10) Uani 1 1 d . . . H32A H 0.5074 -0.0910 0.1772 0.044 Uiso 1 1 calc R . . C33 C 0.4784(4) -0.2588(4) 0.2780(4) 0.0439(11) Uani 1 1 d . . . H33A H 0.5542 -0.2709 0.3027 0.053 Uiso 1 1 calc R . . C34 C 0.3938(4) -0.3485(4) 0.3166(4) 0.0455(11) Uani 1 1 d . . . H34A H 0.4129 -0.4210 0.3670 0.055 Uiso 1 1 calc R . . C35 C 0.2819(4) -0.3308(4) 0.2806(4) 0.0444(11) Uani 1 1 d . . . H35A H 0.2255 -0.3916 0.3062 0.053 Uiso 1 1 calc R . . C36 C 0.2526(4) -0.2238(3) 0.2067(3) 0.0362(10) Uani 1 1 d . . . H36A H 0.1759 -0.2118 0.1838 0.043 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 S1 0.0214(5) 0.0408(6) 0.0299(6) -0.0213(5) -0.0011(4) -0.0042(4) N1 0.0166(16) 0.0205(16) 0.0278(17) -0.0118(13) -0.0032(12) -0.0017(12) C1 0.022(2) 0.0143(18) 0.023(2) -0.0057(15) -0.0030(15) -0.0063(14) O1 0.0243(16) 0.0516(18) 0.0516(18) -0.0308(15) -0.0153(13) 0.0053(13) S2 0.0408(6) 0.0289(6) 0.0307(6) -0.0129(5) 0.0057(4) -0.0012(4) O2 0.0313(15) 0.0284(15) 0.0295(16) -0.0107(13) 0.0013(12) -0.0060(11) N2 0.0189(16) 0.0208(16) 0.0217(16) -0.0076(13) -0.0011(12) -0.0012(12) C2 0.023(2) 0.024(2) 0.028(2) -0.0086(17) -0.0046(16) -0.0058(16) C3 0.028(2) 0.0207(19) 0.024(2) -0.0097(16) -0.0032(15) -0.0044(15) C4 0.026(2) 0.028(2) 0.027(2) -0.0138(18) -0.0018(16) -0.0071(16) C5 0.037(2) 0.037(2) 0.034(2) -0.0157(19) -0.0100(18) -0.0077(18) C6 0.040(2) 0.030(2) 0.024(2) -0.0069(18) -0.0026(17) -0.0061(18) C7 0.0131(18) 0.028(2) 0.026(2) -0.0148(17) -0.0019(14) 0.0008(15) C8 0.018(2) 0.033(2) 0.030(2) -0.0104(18) -0.0049(16) -0.0026(16) C9 0.022(2) 0.043(3) 0.030(2) -0.017(2) -0.0025(16) -0.0004(17) C10 0.024(2) 0.046(3) 0.036(2) -0.024(2) -0.0082(18) 0.0059(18) C11 0.027(2) 0.029(2) 0.044(3) -0.0186(19) -0.0121(18) 0.0056(17) C12 0.0173(19) 0.028(2) 0.027(2) -0.0107(17) -0.0065(15) 0.0017(15) C13 0.036(2) 0.029(2) 0.035(2) -0.0093(19) -0.0012(18) -0.0015(18) C14 0.044(3) 0.060(3) 0.064(3) -0.040(3) -0.003(2) 0.013(2) C15 0.038(2) 0.036(2) 0.033(2) -0.007(2) 0.0043(18) -0.0058(19) C16 0.0190(19) 0.0194(19) 0.022(2) -0.0098(16) -0.0026(14) -0.0011(14) C17 0.026(2) 0.024(2) 0.023(2) -0.0077(17) -0.0019(15) -0.0028(15) C18 0.034(2) 0.020(2) 0.027(2) -0.0032(17) -0.0081(17) 0.0011(16) C19 0.025(2) 0.026(2) 0.033(2) -0.0103(18) -0.0039(17) 0.0005(16) C20 0.020(2) 0.032(2) 0.032(2) -0.0145(19) 0.0071(16) -0.0029(16) C21 0.021(2) 0.026(2) 0.023(2) -0.0117(16) -0.0025(15) 0.0017(15) C22 0.025(2) 0.037(2) 0.025(2) -0.0085(18) -0.0010(16) -0.0018(17) C23 0.029(2) 0.048(3) 0.048(3) -0.009(2) -0.008(2) 0.007(2) C24 0.030(2) 0.042(2) 0.024(2) -0.0007(19) -0.0026(17) -0.0088(18) C25 0.0179(19) 0.023(2) 0.030(2) -0.0141(17) -0.0023(15) -0.0026(15) C26 0.038(3) 0.029(2) 0.032(2) 0.0021(18) -0.0140(18) -0.0096(18) C27 0.033(3) 0.045(3) 0.060(3) -0.002(2) -0.022(2) -0.008(2) C28 0.025(2) 0.043(3) 0.052(3) -0.015(2) -0.008(2) -0.0125(19) C29 0.033(2) 0.032(2) 0.036(2) -0.0041(19) -0.0046(19) -0.0114(18) C30 0.030(2) 0.020(2) 0.034(2) -0.0092(18) -0.0089(17) 0.0006(16) C31 0.033(2) 0.027(2) 0.033(2) -0.0169(18) 0.0055(17) -0.0002(17) C32 0.038(3) 0.031(2) 0.045(3) -0.021(2) 0.0025(19) -0.0036(18) C33 0.046(3) 0.042(3) 0.049(3) -0.020(2) -0.014(2) 0.010(2) C34 0.066(3) 0.028(2) 0.041(3) -0.010(2) -0.008(2) 0.004(2) C35 0.051(3) 0.031(2) 0.050(3) -0.016(2) 0.003(2) -0.005(2) C36 0.037(2) 0.032(2) 0.043(3) -0.021(2) 0.0014(19) -0.0015(19) _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 S1 C25 1.776(3) . ? S1 C1 1.805(3) . ? N1 C2 1.420(4) . ? N1 C1 1.421(4) . ? N1 C7 1.459(4) . ? C1 N2 1.257(4) . ? O1 C2 1.208(4) . ? S2 C31 1.768(4) . ? S2 C4 1.787(4) . ? O2 C4 1.201(4) . ? N2 C16 1.416(4) . ? C2 C3 1.533(5) . ? C3 C5 1.537(5) . ? C3 C6 1.537(5) . ? C3 C4 1.544(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.393(5) . ? C7 C8 1.398(5) . ? C8 C9 1.394(5) . ? C8 C15 1.502(5) . ? C9 C10 1.392(5) . ? C9 H9A 0.9300 . ? C10 C11 1.376(5) . ? C10 C14 1.511(5) . ? C11 C12 1.394(5) . ? C11 H11A 0.9300 . ? C12 C13 1.507(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.393(5) . ? C16 C21 1.404(5) . ? C17 C18 1.394(5) . ? C17 C24 1.502(5) . ? C18 C19 1.385(5) . ? C18 H18A 0.9300 . ? C19 C20 1.387(5) . ? C19 C23 1.512(5) . ? C20 C21 1.380(5) . ? C20 H20A 0.9300 . ? C21 C22 1.502(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C30 1.386(5) . ? C25 C26 1.390(5) . ? C26 C27 1.375(5) . ? C26 H26A 0.9300 . ? C27 C28 1.371(6) . ? C27 H27A 0.9300 . ? C28 C29 1.377(5) . ? C28 H28A 0.9300 . ? C29 C30 1.376(5) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 C36 1.386(5) . ? C31 C32 1.390(5) . ? C32 C33 1.378(5) . ? C32 H32A 0.9300 . ? C33 C34 1.383(6) . ? C33 H33A 0.9300 . ? C34 C35 1.371(6) . ? C34 H34A 0.9300 . ? C35 C36 1.374(6) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? 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 C25 S1 C1 103.48(15) . . ? C2 N1 C1 128.5(3) . . ? C2 N1 C7 113.3(3) . . ? C1 N1 C7 118.2(3) . . ? N2 C1 N1 120.9(3) . . ? N2 C1 S1 128.8(3) . . ? N1 C1 S1 110.3(2) . . ? C31 S2 C4 101.05(17) . . ? C1 N2 C16 125.7(3) . . ? O1 C2 N1 117.1(3) . . ? O1 C2 C3 119.8(3) . . ? N1 C2 C3 122.8(3) . . ? C2 C3 C5 108.3(3) . . ? C2 C3 C6 109.8(3) . . ? C5 C3 C6 108.9(3) . . ? C2 C3 C4 109.2(3) . . ? C5 C3 C4 103.9(3) . . ? C6 C3 C4 116.4(3) . . ? O2 C4 C3 121.1(3) . . ? O2 C4 S2 124.3(3) . . ? C3 C4 S2 113.8(3) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 122.7(3) . . ? C12 C7 N1 117.5(3) . . ? C8 C7 N1 119.8(3) . . ? C9 C8 C7 117.0(3) . . ? C9 C8 C15 121.1(3) . . ? C7 C8 C15 121.9(3) . . ? C10 C9 C8 122.3(4) . . ? C10 C9 H9A 118.9 . . ? C8 C9 H9A 118.9 . . ? C11 C10 C9 118.3(3) . . ? C11 C10 C14 121.0(4) . . ? C9 C10 C14 120.7(4) . . ? C10 C11 C12 122.5(4) . . ? C10 C11 H11A 118.8 . . ? C12 C11 H11A 118.8 . . ? C7 C12 C11 117.3(3) . . ? C7 C12 C13 121.0(3) . . ? C11 C12 C13 121.7(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 120.6(3) . . ? C17 C16 N2 120.2(3) . . ? C21 C16 N2 118.9(3) . . ? C16 C17 C18 117.8(3) . . ? C16 C17 C24 122.4(3) . . ? C18 C17 C24 119.7(3) . . ? C19 C18 C17 123.3(3) . . ? C19 C18 H18A 118.3 . . ? C17 C18 H18A 118.3 . . ? C18 C19 C20 116.8(3) . . ? C18 C19 C23 121.5(3) . . ? C20 C19 C23 121.7(3) . . ? C21 C20 C19 122.8(3) . . ? C21 C20 H20A 118.6 . . ? C19 C20 H20A 118.6 . . ? C20 C21 C16 118.7(3) . . ? C20 C21 C22 120.7(3) . . ? C16 C21 C22 120.7(3) . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 H24A 109.5 . . ? C17 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C30 C25 C26 119.4(3) . . ? C30 C25 S1 120.1(3) . . ? C26 C25 S1 120.1(3) . . ? C27 C26 C25 119.7(4) . . ? C27 C26 H26A 120.2 . . ? C25 C26 H26A 120.2 . . ? C28 C27 C26 120.9(4) . . ? C28 C27 H27A 119.6 . . ? C26 C27 H27A 119.6 . . ? C27 C28 C29 119.5(4) . . ? C27 C28 H28A 120.2 . . ? C29 C28 H28A 120.2 . . ? C30 C29 C28 120.5(4) . . ? C30 C29 H29A 119.7 . . ? C28 C29 H29A 119.7 . . ? C29 C30 C25 119.9(3) . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? C36 C31 C32 119.5(4) . . ? C36 C31 S2 122.0(3) . . ? C32 C31 S2 118.4(3) . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H32A 120.1 . . ? C31 C32 H32A 120.1 . . ? C32 C33 C34 120.1(4) . . ? C32 C33 H33A 119.9 . . ? C34 C33 H33A 119.9 . . ? C35 C34 C33 120.1(4) . . ? C35 C34 H34A 120.0 . . ? C33 C34 H34A 120.0 . . ? C34 C35 C36 120.3(4) . . ? C34 C35 H35A 119.8 . . ? C36 C35 H35A 119.8 . . ? C35 C36 C31 120.1(4) . . ? C35 C36 H36A 119.9 . . ? C31 C36 H36A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.269 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.063 data_DACAcenaphthenedione _database_code_depnum_ccdc_archive 'CCDC 882676' #TrackingRef '11367_web_deposit_cif_file_0_JonathanP.Moerdyk_1337264105.cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DACAcenapthenedione _chemical_melting_point ? _chemical_formula_moiety 'C36 H34 N2 O4' _chemical_formula_sum 'C36 H34 N2 O4' _chemical_formula_weight 558.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 11.500(2) _cell_length_b 17.626(4) _cell_length_c 14.155(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.498(4) _cell_angle_gamma 90.00 _cell_volume 2868.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40760 _diffrn_reflns_av_R_equivalents 0.1188 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5041 _reflns_number_gt 3032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+1.1184P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5041 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.86397(19) 0.31945(12) 0.90647(15) 0.0419(6) Uani 1 1 d . . . O1 O 1.00262(18) 0.38189(12) 0.82727(16) 0.0626(6) Uani 1 1 d . . . C1 C 0.8178(2) 0.24502(15) 0.93144(18) 0.0385(7) Uani 1 1 d . . . N2 N 0.90739(18) 0.20011(12) 0.98392(15) 0.0398(6) Uani 1 1 d . . . O2 O 1.09076(17) 0.15559(12) 0.99253(15) 0.0556(6) Uani 1 1 d . . . C2 C 0.9744(3) 0.32529(17) 0.8710(2) 0.0476(7) Uani 1 1 d . . . O3 O 0.71140(17) 0.30250(11) 1.05584(14) 0.0506(5) Uani 1 1 d . . . C3 C 1.0645(2) 0.26565(16) 0.8978(2) 0.0477(7) Uani 1 1 d . . . O4 O 0.85987(18) 0.20418(12) 0.77570(15) 0.0585(6) Uani 1 1 d . . . C4 C 1.0222(2) 0.20220(16) 0.9597(2) 0.0444(7) Uani 1 1 d . . . C5 C 1.1591(3) 0.30731(19) 0.9579(3) 0.0662(10) Uani 1 1 d . . . H5A H 1.1256 0.3266 1.0144 0.099 Uiso 1 1 calc R . . H5B H 1.1899 0.3486 0.9221 0.099 Uiso 1 1 calc R . . H5C H 1.2206 0.2725 0.9743 0.099 Uiso 1 1 calc R . . C6 C 1.1219(3) 0.23335(19) 0.8104(2) 0.0622(9) Uani 1 1 d . . . H6A H 1.0669 0.2025 0.7756 0.093 Uiso 1 1 calc R . . H6B H 1.1877 0.2030 0.8296 0.093 Uiso 1 1 calc R . . H6C H 1.1473 0.2742 0.7711 0.093 Uiso 1 1 calc R . . C7 C 0.8751(2) 0.14397(16) 1.0539(2) 0.0427(7) Uani 1 1 d . . . C8 C 0.8563(2) 0.06853(16) 1.0277(2) 0.0446(7) Uani 1 1 d . . . C9 C 0.8282(3) 0.01770(18) 1.0987(2) 0.0568(9) Uani 1 1 d . . . H9A H 0.8142 -0.0327 1.0826 0.068 Uiso 1 1 calc R . . C10 C 0.8204(3) 0.0393(2) 1.1922(3) 0.0639(10) Uani 1 1 d . . . C11 C 0.8465(3) 0.1132(2) 1.2156(2) 0.0597(9) Uani 1 1 d . . . H11A H 0.8442 0.1278 1.2786 0.072 Uiso 1 1 calc R . . C12 C 0.8762(2) 0.16686(18) 1.1486(2) 0.0486(8) Uani 1 1 d . . . C13 C 0.9126(3) 0.24444(18) 1.1805(2) 0.0617(9) Uani 1 1 d . . . H13A H 0.9354 0.2429 1.2462 0.092 Uiso 1 1 calc R . . H13B H 0.8488 0.2790 1.1716 0.092 Uiso 1 1 calc R . . H13C H 0.9771 0.2612 1.1442 0.092 Uiso 1 1 calc R . . C14 C 0.7894(4) -0.0180(3) 1.2677(3) 0.1014(15) Uani 1 1 d . . . H14A H 0.8364 -0.0090 1.3237 0.152 Uiso 1 1 calc R . . H14B H 0.8033 -0.0684 1.2450 0.152 Uiso 1 1 calc R . . H14C H 0.7087 -0.0127 1.2824 0.152 Uiso 1 1 calc R . . C15 C 0.8720(3) 0.03767(16) 0.9298(2) 0.0504(8) Uani 1 1 d . . . H15A H 0.9107 0.0747 0.8922 0.076 Uiso 1 1 calc R . . H15B H 0.7973 0.0263 0.9015 0.076 Uiso 1 1 calc R . . H15C H 0.9180 -0.0077 0.9333 0.076 Uiso 1 1 calc R . . C16 C 0.7891(2) 0.38646(16) 0.9017(2) 0.0460(7) Uani 1 1 d . . . C17 C 0.7046(3) 0.39701(17) 0.8303(2) 0.0533(8) Uani 1 1 d . . . C18 C 0.6325(3) 0.46093(19) 0.8365(3) 0.0594(9) Uani 1 1 d . . . H18A H 0.5741 0.4678 0.7906 0.071 Uiso 1 1 calc R . . C19 C 0.6444(3) 0.51372(19) 0.9070(3) 0.0608(9) Uani 1 1 d . . . C20 C 0.7337(3) 0.50356(18) 0.9725(2) 0.0587(9) Uani 1 1 d . . . H20A H 0.7452 0.5401 1.0193 0.070 Uiso 1 1 calc R . . C21 C 0.8074(3) 0.44113(16) 0.9718(2) 0.0504(8) Uani 1 1 d . . . C22 C 0.9020(3) 0.43379(17) 1.0455(2) 0.0576(9) Uani 1 1 d . . . H22A H 0.9749 0.4256 1.0156 0.086 Uiso 1 1 calc R . . H22B H 0.8857 0.3916 1.0859 0.086 Uiso 1 1 calc R . . H22C H 0.9062 0.4794 1.0824 0.086 Uiso 1 1 calc R . . C23 C 0.5629(3) 0.5815(2) 0.9127(3) 0.0859(12) Uani 1 1 d . . . H23A H 0.6033 0.6233 0.9422 0.129 Uiso 1 1 calc R . . H23B H 0.4968 0.5682 0.9493 0.129 Uiso 1 1 calc R . . H23C H 0.5372 0.5959 0.8501 0.129 Uiso 1 1 calc R . . C24 C 0.6903(3) 0.34441(19) 0.7478(2) 0.0667(10) Uani 1 1 d . . . H24A H 0.7655 0.3299 0.7261 0.100 Uiso 1 1 calc R . . H24B H 0.6476 0.3696 0.6978 0.100 Uiso 1 1 calc R . . H24C H 0.6486 0.3000 0.7668 0.100 Uiso 1 1 calc R . . C25 C 0.7117(2) 0.25273(16) 0.9962(2) 0.0430(7) Uani 1 1 d . . . C26 C 0.6164(2) 0.19765(17) 0.9860(2) 0.0495(8) Uani 1 1 d . . . C27 C 0.5357(3) 0.1936(2) 1.0552(3) 0.0769(11) Uani 1 1 d . . . H27A H 0.5401 0.2273 1.1057 0.092 Uiso 1 1 calc R . . C28 C 0.4469(4) 0.1396(3) 1.0509(4) 0.1184(18) Uani 1 1 d . . . H28A H 0.3934 0.1370 1.0989 0.142 Uiso 1 1 calc R . . C29 C 0.4386(4) 0.0909(3) 0.9766(4) 0.1151(17) Uani 1 1 d . . . H29A H 0.3798 0.0546 0.9750 0.138 Uiso 1 1 calc R . . C30 C 0.5173(3) 0.0941(2) 0.9020(3) 0.0747(11) Uani 1 1 d . . . C31 C 0.5112(4) 0.0440(2) 0.8239(3) 0.0853(12) Uani 1 1 d . . . H31A H 0.4545 0.0063 0.8221 0.102 Uiso 1 1 calc R . . C32 C 0.5845(3) 0.0492(2) 0.7527(3) 0.0742(11) Uani 1 1 d . . . H32A H 0.5765 0.0169 0.7010 0.089 Uiso 1 1 calc R . . C33 C 0.6735(3) 0.10344(17) 0.7559(2) 0.0571(9) Uani 1 1 d . . . H33A H 0.7239 0.1074 0.7058 0.069 Uiso 1 1 calc R . . C34 C 0.6872(2) 0.15098(16) 0.8325(2) 0.0455(7) Uani 1 1 d . . . C35 C 0.6086(3) 0.14829(17) 0.9073(2) 0.0510(8) Uani 1 1 d . . . C36 C 0.7897(3) 0.19989(16) 0.8391(2) 0.0441(7) 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 N1 0.0443(14) 0.0376(14) 0.0436(14) 0.0047(11) -0.0026(11) -0.0044(11) O1 0.0627(14) 0.0495(13) 0.0764(15) 0.0189(12) 0.0159(12) -0.0053(11) C1 0.0392(15) 0.0339(15) 0.0423(16) 0.0026(13) -0.0035(13) -0.0011(13) N2 0.0364(13) 0.0403(13) 0.0426(13) 0.0030(11) -0.0012(11) 0.0002(11) O2 0.0430(12) 0.0566(13) 0.0671(14) 0.0112(11) 0.0005(10) 0.0036(11) C2 0.0504(19) 0.0465(19) 0.0459(17) 0.0014(15) 0.0012(15) -0.0087(15) O3 0.0544(13) 0.0474(12) 0.0500(12) -0.0017(10) 0.0025(10) 0.0008(10) C3 0.0402(16) 0.0504(18) 0.0524(18) 0.0055(15) -0.0015(14) -0.0048(14) O4 0.0576(13) 0.0685(15) 0.0495(13) -0.0092(11) 0.0021(11) -0.0046(11) C4 0.0438(17) 0.0421(17) 0.0469(17) -0.0004(14) -0.0042(14) 0.0016(15) C5 0.0498(19) 0.064(2) 0.084(3) 0.0034(19) -0.0072(18) -0.0141(17) C6 0.0527(19) 0.066(2) 0.069(2) 0.0080(18) 0.0144(17) 0.0024(17) C7 0.0380(15) 0.0445(17) 0.0456(17) 0.0074(14) 0.0035(13) 0.0026(14) C8 0.0333(15) 0.0467(18) 0.0537(19) 0.0081(15) 0.0000(13) 0.0034(14) C9 0.0477(18) 0.0477(19) 0.075(2) 0.0169(17) 0.0062(17) -0.0010(15) C10 0.057(2) 0.075(3) 0.061(2) 0.027(2) 0.0154(17) 0.0074(19) C11 0.055(2) 0.077(3) 0.0470(19) 0.0119(18) 0.0059(16) 0.0167(19) C12 0.0443(17) 0.058(2) 0.0433(18) 0.0060(16) 0.0010(14) 0.0098(15) C13 0.064(2) 0.070(2) 0.0506(19) -0.0080(17) -0.0071(16) 0.0100(18) C14 0.099(3) 0.117(4) 0.088(3) 0.055(3) 0.019(2) -0.002(3) C15 0.0501(18) 0.0394(17) 0.061(2) 0.0010(15) -0.0064(15) 0.0012(14) C16 0.0485(17) 0.0394(17) 0.0500(18) 0.0087(14) -0.0014(15) -0.0026(14) C17 0.0500(18) 0.0503(19) 0.059(2) 0.0102(16) -0.0037(16) -0.0060(16) C18 0.0460(18) 0.057(2) 0.075(2) 0.0232(19) -0.0045(17) 0.0006(17) C19 0.061(2) 0.048(2) 0.074(2) 0.0140(18) 0.0103(19) 0.0012(17) C20 0.066(2) 0.0455(19) 0.065(2) 0.0051(16) 0.0096(18) -0.0009(17) C21 0.0540(18) 0.0385(17) 0.059(2) 0.0039(15) 0.0058(16) -0.0040(15) C22 0.065(2) 0.0477(19) 0.060(2) -0.0055(16) -0.0031(17) -0.0082(16) C23 0.079(3) 0.061(2) 0.119(3) 0.024(2) 0.020(2) 0.019(2) C24 0.073(2) 0.063(2) 0.063(2) 0.0135(18) -0.0215(18) -0.0035(19) C25 0.0462(17) 0.0407(17) 0.0417(17) 0.0026(14) -0.0057(14) 0.0037(14) C26 0.0415(17) 0.0530(19) 0.0538(19) -0.0016(16) -0.0011(15) -0.0074(15) C27 0.061(2) 0.097(3) 0.074(2) -0.014(2) 0.014(2) -0.023(2) C28 0.094(3) 0.150(5) 0.113(4) -0.031(3) 0.042(3) -0.069(3) C29 0.089(3) 0.138(4) 0.119(4) -0.025(3) 0.020(3) -0.070(3) C30 0.067(2) 0.075(3) 0.082(3) -0.004(2) 0.001(2) -0.028(2) C31 0.080(3) 0.079(3) 0.096(3) -0.016(2) -0.019(3) -0.032(2) C32 0.082(3) 0.055(2) 0.084(3) -0.017(2) -0.029(2) -0.003(2) C33 0.057(2) 0.0533(19) 0.060(2) -0.0100(16) -0.0193(16) 0.0050(17) C34 0.0448(17) 0.0400(17) 0.0511(18) -0.0035(14) -0.0128(15) 0.0010(14) C35 0.0451(17) 0.0484(18) 0.059(2) -0.0005(16) -0.0102(16) -0.0060(15) C36 0.0451(17) 0.0471(18) 0.0398(17) -0.0037(14) -0.0044(14) 0.0019(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.382(4) . ? N1 C1 1.462(3) . ? N1 C16 1.462(3) . ? O1 C2 1.222(3) . ? C1 N2 1.483(3) . ? C1 C25 1.552(4) . ? C1 C36 1.557(4) . ? N2 C4 1.373(3) . ? N2 C7 1.455(3) . ? O2 C4 1.222(3) . ? C2 C3 1.517(4) . ? O3 C25 1.217(3) . ? C3 C4 1.509(4) . ? C3 C6 1.528(4) . ? C3 C5 1.549(4) . ? O4 C36 1.224(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.396(4) . ? C7 C12 1.401(4) . ? C8 C9 1.391(4) . ? C8 C15 1.503(4) . ? C9 C10 1.382(5) . ? C9 H9A 0.9300 . ? C10 C11 1.376(5) . ? C10 C14 1.520(5) . ? C11 C12 1.388(4) . ? C11 H11A 0.9300 . ? C12 C13 1.497(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.396(4) . ? C16 C21 1.396(4) . ? C17 C18 1.403(4) . ? C17 C24 1.496(4) . ? C18 C19 1.369(5) . ? C18 H18A 0.9300 . ? C19 C20 1.377(5) . ? C19 C23 1.522(5) . ? C20 C21 1.389(4) . ? C20 H20A 0.9300 . ? C21 C22 1.493(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.468(4) . ? C26 C27 1.369(4) . ? C26 C35 1.415(4) . ? C27 C28 1.396(5) . ? C27 H27A 0.9300 . ? C28 C29 1.360(6) . ? C28 H28A 0.9300 . ? C29 C30 1.409(6) . ? C29 H29A 0.9300 . ? C30 C31 1.416(5) . ? C30 C35 1.420(4) . ? C31 C32 1.333(5) . ? C31 H31A 0.9300 . ? C32 C33 1.401(5) . ? C32 H32A 0.9300 . ? C33 C34 1.376(4) . ? C33 H33A 0.9300 . ? C34 C35 1.410(4) . ? C34 C36 1.462(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 C2 N1 C1 119.8(2) . . ? C2 N1 C16 117.9(2) . . ? C1 N1 C16 121.3(2) . . ? N1 C1 N2 110.4(2) . . ? N1 C1 C25 111.1(2) . . ? N2 C1 C25 107.3(2) . . ? N1 C1 C36 108.9(2) . . ? N2 C1 C36 105.9(2) . . ? C25 C1 C36 113.1(2) . . ? C4 N2 C7 116.9(2) . . ? C4 N2 C1 121.4(2) . . ? C7 N2 C1 121.2(2) . . ? O1 C2 N1 120.2(3) . . ? O1 C2 C3 120.2(3) . . ? N1 C2 C3 119.0(3) . . ? C4 C3 C2 115.5(2) . . ? C4 C3 C6 110.3(2) . . ? C2 C3 C6 111.3(2) . . ? C4 C3 C5 105.4(2) . . ? C2 C3 C5 105.9(2) . . ? C6 C3 C5 108.0(2) . . ? O2 C4 N2 120.1(3) . . ? O2 C4 C3 120.3(3) . . ? N2 C4 C3 119.4(2) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 121.8(3) . . ? C8 C7 N2 120.5(2) . . ? C12 C7 N2 117.4(3) . . ? C9 C8 C7 117.3(3) . . ? C9 C8 C15 117.9(3) . . ? C7 C8 C15 124.6(3) . . ? C10 C9 C8 122.5(3) . . ? C10 C9 H9A 118.8 . . ? C8 C9 H9A 118.8 . . ? C11 C10 C9 118.2(3) . . ? C11 C10 C14 120.9(4) . . ? C9 C10 C14 120.9(4) . . ? C10 C11 C12 122.5(3) . . ? C10 C11 H11A 118.8 . . ? C12 C11 H11A 118.8 . . ? C11 C12 C7 117.5(3) . . ? C11 C12 C13 119.3(3) . . ? C7 C12 C13 123.2(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 120.8(3) . . ? C17 C16 N1 122.6(3) . . ? C21 C16 N1 116.5(3) . . ? C16 C17 C18 117.6(3) . . ? C16 C17 C24 122.8(3) . . ? C18 C17 C24 119.6(3) . . ? C19 C18 C17 122.9(3) . . ? C19 C18 H18A 118.5 . . ? C17 C18 H18A 118.5 . . ? C18 C19 C20 117.5(3) . . ? C18 C19 C23 121.5(3) . . ? C20 C19 C23 121.1(3) . . ? C19 C20 C21 122.8(3) . . ? C19 C20 H20A 118.6 . . ? C21 C20 H20A 118.6 . . ? C20 C21 C16 118.2(3) . . ? C20 C21 C22 119.8(3) . . ? C16 C21 C22 122.1(3) . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 H24A 109.5 . . ? C17 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C17 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 C26 122.0(3) . . ? O3 C25 C1 119.3(2) . . ? C26 C25 C1 118.7(2) . . ? C27 C26 C35 120.1(3) . . ? C27 C26 C25 118.8(3) . . ? C35 C26 C25 121.1(3) . . ? C26 C27 C28 120.9(4) . . ? C26 C27 H27A 119.6 . . ? C28 C27 H27A 119.6 . . ? C29 C28 C27 120.1(4) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 121.4(4) . . ? C28 C29 H29A 119.3 . . ? C30 C29 H29A 119.3 . . ? C29 C30 C31 122.7(4) . . ? C29 C30 C35 118.4(4) . . ? C31 C30 C35 118.8(4) . . ? C32 C31 C30 121.8(4) . . ? C32 C31 H31A 119.1 . . ? C30 C31 H31A 119.1 . . ? C31 C32 C33 119.9(3) . . ? C31 C32 H32A 120.0 . . ? C33 C32 H32A 120.0 . . ? C34 C33 C32 120.6(3) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C33 C34 C35 120.6(3) . . ? C33 C34 C36 119.0(3) . . ? C35 C34 C36 120.2(3) . . ? C34 C35 C26 122.8(3) . . ? C34 C35 C30 118.1(3) . . ? C26 C35 C30 119.1(3) . . ? O4 C36 C34 122.4(3) . . ? O4 C36 C1 117.2(2) . . ? C34 C36 C1 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.191 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.039