# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Williams, Charlotte' _publ_contact_author_email c.k.williams@imperial.ac.uk _publ_section_title ; The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics ; loop_ _publ_author_name C.Williams C.Keyworth A.Holmes K.L.Chan J.Labram ; T.Anthopoulos ; S.Watkins M.McKiernan A.White # Attachment '- CIF_JMaterChem2011_CKeyworthEtAl.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 803757' #TrackingRef '- CIF_JMaterChem2011_CKeyworthEtAl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H21 Br2 N' _chemical_formula_sum 'C22 H21 Br2 N' _chemical_formula_weight 459.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 7.0740(3) _cell_length_b 10.1883(4) _cell_length_c 13.9770(5) _cell_angle_alpha 80.255(3) _cell_angle_beta 87.742(3) _cell_angle_gamma 89.718(3) _cell_volume 992.04(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7459 _cell_measurement_theta_min 3.2119 _cell_measurement_theta_max 72.3797 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 5.194 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.693 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12528 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 72.57 _reflns_number_total 3929 _reflns_number_gt 3332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.6517P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3929 _refine_ls_number_parameters 224 _refine_ls_number_restraints 97 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.109 _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 N1 N 0.5058(4) 0.1940(2) 0.68283(16) 0.0476(5) Uani 1 1 d . . . C2 C 0.5903(10) 0.2058(6) 0.7715(4) 0.033(2) Uiso 0.430(4) 1 d PGD A 1 C3 C 0.5937(10) 0.0957(5) 0.8454(5) 0.038(4) Uiso 0.430(4) 1 d PGD A 1 H3A H 0.5359 0.0146 0.8371 0.046 Uiso 0.430(4) 1 calc PR A 1 C4 C 0.6814(9) 0.1044(5) 0.9313(4) 0.045(2) Uiso 0.430(4) 1 d PGD A 1 H4A H 0.6837 0.0292 0.9818 0.054 Uiso 0.430(4) 1 calc PR A 1 C5 C 0.7659(7) 0.2230(5) 0.9435(3) 0.0442(15) Uiso 0.430(4) 1 d PGD A 1 C6 C 0.7626(8) 0.3331(5) 0.8696(3) 0.0441(15) Uiso 0.430(4) 1 d PGD A 1 H6A H 0.8203 0.4142 0.8779 0.053 Uiso 0.430(4) 1 calc PR A 1 C7 C 0.6748(10) 0.3244(5) 0.7837(3) 0.0433(18) Uiso 0.430(4) 1 d PGD A 1 H7A H 0.6725 0.3996 0.7332 0.052 Uiso 0.430(4) 1 calc PR A 1 C8 C 0.8740(9) 0.2296(8) 1.0363(5) 0.0540(17) Uiso 0.430(4) 1 d PD A 1 H8A H 0.8697 0.1407 1.0795 0.065 Uiso 0.430(4) 1 calc PR A 1 C9 C 0.7980(11) 0.3354(8) 1.0921(6) 0.066(2) Uiso 0.430(4) 1 d PD A 1 H9A H 0.7888 0.4220 1.0480 0.080 Uiso 0.430(4) 1 calc PR A 1 H9B H 0.8836 0.3461 1.1446 0.080 Uiso 0.430(4) 1 calc PR A 1 C10 C 0.5994(12) 0.2895(10) 1.1357(7) 0.059(2) Uiso 0.430(4) 1 d PD A 1 H10A H 0.5466 0.3562 1.1722 0.088 Uiso 0.430(4) 1 calc PR A 1 H10B H 0.6103 0.2040 1.1794 0.088 Uiso 0.430(4) 1 calc PR A 1 H10C H 0.5158 0.2794 1.0831 0.088 Uiso 0.430(4) 1 calc PR A 1 C11 C 1.0925(10) 0.2714(10) 1.0062(7) 0.059(2) Uiso 0.430(4) 1 d PD A 1 H11A H 1.1619 0.2758 1.0649 0.089 Uiso 0.430(4) 1 calc PR A 1 H11B H 1.0961 0.3587 0.9640 0.089 Uiso 0.430(4) 1 calc PR A 1 H11C H 1.1512 0.2048 0.9715 0.089 Uiso 0.430(4) 1 calc PR A 1 C2' C 0.5597(15) 0.2060(8) 0.7797(5) 0.048(4) Uiso 0.291(7) 1 d PGD A 2 C3' C 0.5769(17) 0.0943(7) 0.8512(6) 0.045(6) Uiso 0.291(7) 1 d PGD A 2 H3'A H 0.5429 0.0090 0.8385 0.054 Uiso 0.291(7) 1 calc PR A 2 C4' C 0.6439(14) 0.1074(6) 0.9412(5) 0.040(3) Uiso 0.291(7) 1 d PGD A 2 H4'A H 0.6556 0.0310 0.9901 0.048 Uiso 0.291(7) 1 calc PR A 2 C5' C 0.6937(10) 0.2322(7) 0.9598(4) 0.044(2) Uiso 0.291(7) 1 d PGD A 2 C6' C 0.6765(11) 0.3439(6) 0.8883(4) 0.040(2) Uiso 0.291(7) 1 d PGD A 2 H6'A H 0.7105 0.4292 0.9010 0.048 Uiso 0.291(7) 1 calc PR A 2 C7' C 0.6095(12) 0.3308(7) 0.7982(4) 0.033(2) Uiso 0.291(7) 1 d PGD A 2 H7'A H 0.5978 0.4071 0.7494 0.040 Uiso 0.291(7) 1 calc PR A 2 C8' C 0.7649(12) 0.2446(10) 1.0604(7) 0.057(3) Uiso 0.291(7) 1 d PD A 2 H8'A H 0.7763 0.1530 1.0990 0.068 Uiso 0.291(7) 1 calc PR A 2 C9' C 0.9559(14) 0.3136(12) 1.0570(9) 0.069(4) Uiso 0.291(7) 1 d PD A 2 H9'A H 0.9923 0.3234 1.1231 0.083 Uiso 0.291(7) 1 calc PR A 2 H9'B H 0.9523 0.4029 1.0161 0.083 Uiso 0.291(7) 1 calc PR A 2 C10' C 1.0976(17) 0.2208(15) 1.0119(11) 0.059(3) Uiso 0.291(7) 1 d PD A 2 H10D H 1.2249 0.2594 1.0075 0.089 Uiso 0.291(7) 1 calc PR A 2 H10E H 1.0587 0.2120 0.9467 0.089 Uiso 0.291(7) 1 calc PR A 2 H10F H 1.0981 0.1328 1.0530 0.089 Uiso 0.291(7) 1 calc PR A 2 C11' C 0.621(2) 0.326(2) 1.1167(12) 0.079(6) Uiso 0.291(7) 1 d PD A 2 H11D H 0.6701 0.3327 1.1804 0.119 Uiso 0.291(7) 1 calc PR A 2 H11E H 0.4985 0.2809 1.1254 0.119 Uiso 0.291(7) 1 calc PR A 2 H11F H 0.6064 0.4159 1.0792 0.119 Uiso 0.291(7) 1 calc PR A 2 C2" C 0.5848(13) 0.2288(8) 0.7725(4) 0.042(4) Uiso 0.279(7) 1 d PGD A 3 C3" C 0.5931(11) 0.1271(7) 0.8522(5) 0.039(2) Uiso 0.279(7) 1 d PGD A 3 H3"A H 0.5422 0.0419 0.8492 0.046 Uiso 0.279(7) 1 calc PR A 3 C4" C 0.6761(9) 0.1502(7) 0.9364(4) 0.033(2) Uiso 0.279(7) 1 d PGD A 3 H4"A H 0.6818 0.0808 0.9909 0.039 Uiso 0.279(7) 1 calc PR A 3 C5" C 0.7506(9) 0.2749(8) 0.9408(4) 0.043(2) Uiso 0.279(7) 1 d PGD A 3 C6" C 0.7422(12) 0.3766(7) 0.8610(5) 0.044(2) Uiso 0.279(7) 1 d PGD A 3 H6"A H 0.7932 0.4618 0.8640 0.053 Uiso 0.279(7) 1 calc PR A 3 C7" C 0.6593(14) 0.3535(8) 0.7769(4) 0.042(3) Uiso 0.279(7) 1 d PGD A 3 H7"A H 0.6536 0.4230 0.7224 0.050 Uiso 0.279(7) 1 calc PR A 3 C8" C 0.8500(13) 0.2977(12) 1.0326(6) 0.057(3) Uiso 0.279(7) 1 d PD A 3 H8"A H 0.8745 0.3956 1.0251 0.069 Uiso 0.279(7) 1 calc PR A 3 C9" C 0.7320(16) 0.2597(12) 1.1261(7) 0.062(3) Uiso 0.279(7) 1 d PD A 3 H9"A H 0.8067 0.2701 1.1828 0.075 Uiso 0.279(7) 1 calc PR A 3 H9"B H 0.6895 0.1660 1.1335 0.075 Uiso 0.279(7) 1 calc PR A 3 C10" C 0.5605(17) 0.3544(14) 1.1185(10) 0.058(3) Uiso 0.279(7) 1 d PD A 3 H10G H 0.4790 0.3333 1.1774 0.087 Uiso 0.279(7) 1 calc PR A 3 H10H H 0.4887 0.3435 1.0618 0.087 Uiso 0.279(7) 1 calc PR A 3 H10I H 0.6048 0.4467 1.1115 0.087 Uiso 0.279(7) 1 calc PR A 3 C11" C 1.0431(15) 0.2293(14) 1.0407(9) 0.058(3) Uiso 0.279(7) 1 d PD A 3 H11G H 1.1023 0.2458 1.0998 0.086 Uiso 0.279(7) 1 calc PR A 3 H11H H 1.1241 0.2651 0.9838 0.086 Uiso 0.279(7) 1 calc PR A 3 H11I H 1.0266 0.1332 1.0436 0.086 Uiso 0.279(7) 1 calc PR A 3 C12 C 0.5889(4) 0.2607(3) 0.59421(19) 0.0422(6) Uani 1 1 d . A . C13 C 0.7827(4) 0.2851(3) 0.5838(2) 0.0458(6) Uani 1 1 d . . . H13A H 0.8615 0.2529 0.6361 0.055 Uiso 1 1 calc R A . C14 C 0.8625(4) 0.3553(3) 0.4987(2) 0.0481(6) Uani 1 1 d . A . H14A H 0.9946 0.3730 0.4931 0.058 Uiso 1 1 calc R . . C15 C 0.7484(4) 0.3995(3) 0.4217(2) 0.0458(6) Uani 1 1 d . . . Br15 Br 0.85696(5) 0.50214(3) 0.30679(2) 0.06261(15) Uani 1 1 d . A . C16 C 0.5569(4) 0.3724(3) 0.4289(2) 0.0478(6) Uani 1 1 d . A . H16A H 0.4803 0.4004 0.3749 0.057 Uiso 1 1 calc R . . C17 C 0.4769(4) 0.3044(3) 0.5149(2) 0.0449(6) Uani 1 1 d . . . H17A H 0.3447 0.2872 0.5201 0.054 Uiso 1 1 calc R A . C18 C 0.3443(4) 0.1120(3) 0.68283(19) 0.0427(6) Uani 1 1 d . A . C19 C 0.3337(4) 0.0274(3) 0.6150(2) 0.0501(7) Uani 1 1 d . . . H19A H 0.4369 0.0227 0.5701 0.060 Uiso 1 1 calc R A . C20 C 0.1748(5) -0.0502(3) 0.6119(2) 0.0534(7) Uani 1 1 d . A . H20A H 0.1669 -0.1064 0.5645 0.064 Uiso 1 1 calc R . . C21 C 0.0284(4) -0.0444(3) 0.6788(2) 0.0492(6) Uani 1 1 d . . . Br21 Br -0.19369(5) -0.14886(4) 0.67409(3) 0.07180(16) Uani 1 1 d . A . C22 C 0.0377(4) 0.0354(3) 0.7483(2) 0.0515(7) Uani 1 1 d . A . H22A H -0.0632 0.0359 0.7951 0.062 Uiso 1 1 calc R . . C23 C 0.1955(4) 0.1152(3) 0.7498(2) 0.0474(6) Uani 1 1 d . . . H23A H 0.2014 0.1722 0.7969 0.057 Uiso 1 1 calc R A . 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 0.0518(13) 0.0569(14) 0.0354(11) -0.0108(10) -0.0048(10) -0.0093(11) C12 0.0483(14) 0.0407(13) 0.0388(13) -0.0085(10) -0.0088(11) -0.0041(11) C13 0.0470(15) 0.0429(13) 0.0467(14) -0.0019(11) -0.0150(12) -0.0058(11) C14 0.0462(15) 0.0434(14) 0.0537(16) -0.0035(12) -0.0102(12) -0.0095(11) C15 0.0581(16) 0.0371(13) 0.0420(13) -0.0050(10) -0.0060(12) -0.0076(11) Br15 0.0788(3) 0.0576(2) 0.0478(2) 0.00242(14) -0.00495(15) -0.02188(16) C16 0.0555(16) 0.0446(14) 0.0436(14) -0.0051(11) -0.0168(12) -0.0028(12) C17 0.0423(14) 0.0501(15) 0.0432(14) -0.0085(11) -0.0107(11) -0.0030(11) C18 0.0451(14) 0.0452(14) 0.0380(13) -0.0065(10) -0.0039(11) -0.0031(11) C19 0.0494(15) 0.0557(16) 0.0473(15) -0.0165(12) 0.0073(12) -0.0071(13) C20 0.0555(17) 0.0548(16) 0.0524(16) -0.0167(13) -0.0007(13) -0.0088(13) C21 0.0417(14) 0.0518(15) 0.0518(16) -0.0012(12) -0.0066(12) -0.0036(12) Br21 0.0489(2) 0.0853(3) 0.0805(3) -0.0106(2) -0.00594(17) -0.01920(17) C22 0.0408(14) 0.0669(18) 0.0451(15) -0.0048(13) -0.0008(11) 0.0057(13) C23 0.0478(15) 0.0551(16) 0.0412(14) -0.0134(12) -0.0051(11) 0.0068(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 C12 1.416(4) . ? N1 C18 1.419(4) . ? N1 C2 1.421(4) . ? N1 C2' 1.445(5) . ? N1 C2" 1.488(5) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C8 1.544(7) . ? C6 C7 1.3900 . ? C8 C9 1.517(9) . ? C8 C11 1.625(9) . ? C9 C10 1.551(10) . ? C2' C3' 1.3900 . ? C2' C7' 1.3900 . ? C3' C4' 1.3900 . ? C4' C5' 1.3900 . ? C5' C6' 1.3900 . ? C5' C8' 1.537(9) . ? C6' C7' 1.3900 . ? C8' C9' 1.521(11) . ? C8' C11' 1.579(11) . ? C9' C10' 1.562(12) . ? C2" C3" 1.3900 . ? C2" C7" 1.3900 . ? C3" C4" 1.3900 . ? C4" C5" 1.3900 . ? C5" C6" 1.3900 . ? C5" C8" 1.539(9) . ? C6" C7" 1.3900 . ? C8" C9" 1.516(11) . ? C8" C11" 1.530(11) . ? C9" C10" 1.542(12) . ? C12 C13 1.392(4) . ? C12 C17 1.398(4) . ? C13 C14 1.381(4) . ? C14 C15 1.383(4) . ? C15 C16 1.381(4) . ? C15 Br15 1.899(3) . ? C16 C17 1.383(4) . ? C18 C23 1.385(4) . ? C18 C19 1.390(4) . ? C19 C20 1.383(4) . ? C20 C21 1.376(4) . ? C21 C22 1.372(4) . ? C21 Br21 1.912(3) . ? C22 C23 1.387(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 C12 N1 C18 120.4(2) . . ? C12 N1 C2 119.3(4) . . ? C18 N1 C2 120.3(4) . . ? C12 N1 C2' 126.8(4) . . ? C18 N1 C2' 112.7(4) . . ? C12 N1 C2" 115.5(4) . . ? C18 N1 C2" 123.7(4) . . ? C3 C2 C7 120.0 . . ? C3 C2 N1 119.3(4) . . ? C7 C2 N1 120.7(4) . . ? C2 C3 C4 120.0 . . ? C5 C4 C3 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C8 120.1(4) . . ? C4 C5 C8 119.8(4) . . ? C5 C6 C7 120.0 . . ? C6 C7 C2 120.0 . . ? C9 C8 C5 113.1(5) . . ? C9 C8 C11 105.5(6) . . ? C5 C8 C11 109.1(5) . . ? C8 C9 C10 107.6(7) . . ? C3' C2' C7' 120.0 . . ? C3' C2' N1 121.1(5) . . ? C7' C2' N1 118.7(5) . . ? C4' C3' C2' 120.0 . . ? C3' C4' C5' 120.0 . . ? C4' C5' C6' 120.0 . . ? C4' C5' C8' 119.1(5) . . ? C6' C5' C8' 120.9(5) . . ? C7' C6' C5' 120.0 . . ? C6' C7' C2' 120.0 . . ? C9' C8' C5' 113.9(7) . . ? C9' C8' C11' 106.7(9) . . ? C5' C8' C11' 111.1(8) . . ? C8' C9' C10' 105.0(9) . . ? C3" C2" C7" 120.0 . . ? C3" C2" N1 116.9(5) . . ? C7" C2" N1 123.0(5) . . ? C2" C3" C4" 120.0 . . ? C5" C4" C3" 120.0 . . ? C6" C5" C4" 120.0 . . ? C6" C5" C8" 120.4(5) . . ? C4" C5" C8" 119.6(5) . . ? C5" C6" C7" 120.0 . . ? C6" C7" C2" 120.0 . . ? C9" C8" C11" 110.6(9) . . ? C9" C8" C5" 114.3(7) . . ? C11" C8" C5" 111.6(7) . . ? C8" C9" C10" 106.4(9) . . ? C13 C12 C17 118.4(3) . . ? C13 C12 N1 121.2(2) . . ? C17 C12 N1 120.4(2) . . ? C14 C13 C12 121.2(3) . . ? C13 C14 C15 119.4(3) . . ? C16 C15 C14 120.6(3) . . ? C16 C15 Br15 120.2(2) . . ? C14 C15 Br15 119.2(2) . . ? C15 C16 C17 119.8(3) . . ? C16 C17 C12 120.6(3) . . ? C23 C18 C19 119.2(3) . . ? C23 C18 N1 120.7(2) . . ? C19 C18 N1 120.1(3) . . ? C20 C19 C18 120.9(3) . . ? C21 C20 C19 118.8(3) . . ? C22 C21 C20 121.5(3) . . ? C22 C21 Br21 119.3(2) . . ? C20 C21 Br21 119.2(2) . . ? C21 C22 C23 119.6(3) . . ? C18 C23 C22 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 72.57 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.605 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.061 #===END data_11 _database_code_depnum_ccdc_archive 'CCDC 803758' #TrackingRef '- CIF_JMaterChem2011_CKeyworthEtAl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H29 Br2 N3 O' _chemical_formula_sum 'C28 H29 Br2 N3 O' _chemical_formula_weight 583.36 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.3994(4) _cell_length_b 9.5710(2) _cell_length_c 28.8219(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.402(2) _cell_angle_gamma 90.00 _cell_volume 5263.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10474 _cell_measurement_theta_min 3.0759 _cell_measurement_theta_max 32.9634 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 3.105 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.588 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 15.9825 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29084 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 33.04 _reflns_number_total 9031 _reflns_number_gt 5676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9031 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.005 _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 0.97964(7) 0.60511(14) 0.66710(5) 0.0186(3) Uani 1 1 d . . . C2 C 1.04222(8) 0.55587(17) 0.69198(6) 0.0196(3) Uani 1 1 d . . . N3 N 1.08094(7) 0.66177(14) 0.71050(5) 0.0252(3) Uani 1 1 d . . . N4 N 1.04382(7) 0.78390(14) 0.69846(5) 0.0256(3) Uani 1 1 d . . . C5 C 0.98333(8) 0.74664(16) 0.67282(6) 0.0216(3) Uani 1 1 d . . . C6 C 0.91635(8) 0.53057(16) 0.64709(6) 0.0181(3) Uani 1 1 d . . . C7 C 0.90735(9) 0.47439(18) 0.60225(6) 0.0242(4) Uani 1 1 d . . . H7A H 0.9437 0.4804 0.5843 0.029 Uiso 1 1 calc R . . C8 C 0.84482(9) 0.40936(19) 0.58389(6) 0.0273(4) Uani 1 1 d . . . H8A H 0.8380 0.3710 0.5530 0.033 Uiso 1 1 calc R . . C9 C 0.79178(8) 0.39979(17) 0.61035(6) 0.0205(3) Uani 1 1 d . . . C10 C 0.80152(9) 0.45518(18) 0.65559(6) 0.0229(4) Uani 1 1 d . . . H10A H 0.7658 0.4475 0.6741 0.027 Uiso 1 1 calc R . . C11 C 0.86438(8) 0.52214(17) 0.67348(6) 0.0209(3) Uani 1 1 d . . . H11A H 0.8713 0.5622 0.7041 0.025 Uiso 1 1 calc R . . O12 O 0.73206(6) 0.33296(13) 0.58932(4) 0.0267(3) Uani 1 1 d . . . C13 C 0.68053(9) 0.3009(2) 0.61807(6) 0.0300(4) Uani 1 1 d . . . H13A H 0.6596 0.3879 0.6279 0.036 Uiso 1 1 calc R . . H13B H 0.7024 0.2491 0.6467 0.036 Uiso 1 1 calc R . . C14 C 0.62479(10) 0.2121(2) 0.58802(7) 0.0344(5) Uani 1 1 d . . . H14A H 0.6476 0.1309 0.5758 0.041 Uiso 1 1 calc R . . H14B H 0.5923 0.1760 0.6080 0.041 Uiso 1 1 calc R . . C15 C 0.58374(10) 0.2903(2) 0.54755(7) 0.0391(5) Uani 1 1 d . . . H15A H 0.6163 0.3264 0.5276 0.047 Uiso 1 1 calc R . . H15B H 0.5612 0.3717 0.5599 0.047 Uiso 1 1 calc R . . C16 C 0.52727(9) 0.2025(2) 0.51693(7) 0.0343(4) Uani 1 1 d . . . H16A H 0.5500 0.1241 0.5031 0.041 Uiso 1 1 calc R . . H16B H 0.4961 0.1622 0.5371 0.041 Uiso 1 1 calc R . . C17 C 0.48303(11) 0.2856(2) 0.47725(7) 0.0405(5) Uani 1 1 d . . . H17A H 0.4677 0.3735 0.4904 0.049 Uiso 1 1 calc R . . H17B H 0.5125 0.3108 0.4538 0.049 Uiso 1 1 calc R . . C18 C 0.41894(10) 0.2076(2) 0.45239(7) 0.0359(5) Uani 1 1 d . . . H18A H 0.3909 0.1774 0.4761 0.043 Uiso 1 1 calc R . . H18B H 0.4343 0.1226 0.4375 0.043 Uiso 1 1 calc R . . C19 C 0.37286(11) 0.2938(2) 0.41491(7) 0.0404(5) Uani 1 1 d . . . H19A H 0.3632 0.3851 0.4286 0.049 Uiso 1 1 calc R . . H19B H 0.3984 0.3117 0.3887 0.049 Uiso 1 1 calc R . . C20 C 0.30437(11) 0.2231(3) 0.39563(8) 0.0520(6) Uani 1 1 d . . . H20A H 0.2763 0.2837 0.3721 0.078 Uiso 1 1 calc R . . H20B H 0.2787 0.2053 0.4214 0.078 Uiso 1 1 calc R . . H20C H 0.3135 0.1344 0.3809 0.078 Uiso 1 1 calc R . . C21 C 1.06648(8) 0.41032(17) 0.69780(6) 0.0192(3) Uani 1 1 d . . . C22 C 1.13855(8) 0.39034(17) 0.71301(6) 0.0203(3) Uani 1 1 d . . . H22A H 1.1693 0.4684 0.7176 0.024 Uiso 1 1 calc R . . C23 C 1.16461(8) 0.25694(17) 0.72131(6) 0.0210(3) Uani 1 1 d . . . Br23 Br 1.262321(9) 0.234854(19) 0.743891(6) 0.02660(5) Uani 1 1 d . . . C24 C 1.12184(9) 0.14113(18) 0.71389(6) 0.0253(4) Uani 1 1 d . . . H24A H 1.1408 0.0497 0.7191 0.030 Uiso 1 1 calc R . . C25 C 1.05101(9) 0.16107(18) 0.69880(7) 0.0289(4) Uani 1 1 d . . . H25A H 1.0209 0.0822 0.6936 0.035 Uiso 1 1 calc R . . C26 C 1.02282(9) 0.29354(18) 0.69111(6) 0.0265(4) Uani 1 1 d . . . H26A H 0.9737 0.3050 0.6813 0.032 Uiso 1 1 calc R . . C27 C 0.92698(8) 0.84522(17) 0.65310(6) 0.0216(4) Uani 1 1 d . . . C28 C 0.90167(9) 0.85067(19) 0.60507(6) 0.0272(4) Uani 1 1 d . . . H28A H 0.9191 0.7887 0.5842 0.033 Uiso 1 1 calc R . . C29 C 0.85063(10) 0.9475(2) 0.58798(6) 0.0294(4) Uani 1 1 d . . . Br29 Br 0.813837(13) 0.95471(3) 0.522618(8) 0.05496(8) Uani 1 1 d . . . C30 C 0.82519(10) 1.03922(19) 0.61745(7) 0.0328(4) Uani 1 1 d . . . H30A H 0.7906 1.1062 0.6050 0.039 Uiso 1 1 calc R . . C31 C 0.85051(10) 1.0329(2) 0.66541(7) 0.0358(5) Uani 1 1 d . . . H31A H 0.8333 1.0958 0.6861 0.043 Uiso 1 1 calc R . . C32 C 0.90106(9) 0.93480(18) 0.68349(7) 0.0273(4) Uani 1 1 d . . . H32A H 0.9177 0.9293 0.7165 0.033 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 0.0152(6) 0.0154(7) 0.0244(7) -0.0001(6) 0.0018(6) 0.0008(5) C2 0.0133(7) 0.0203(8) 0.0243(8) -0.0001(7) 0.0007(7) 0.0004(6) N3 0.0200(7) 0.0181(8) 0.0344(8) -0.0009(7) -0.0032(7) 0.0016(6) N4 0.0206(7) 0.0170(7) 0.0362(8) -0.0018(7) -0.0030(7) 0.0015(6) C5 0.0190(8) 0.0166(8) 0.0287(9) -0.0015(7) 0.0026(7) 0.0002(6) C6 0.0118(7) 0.0154(8) 0.0253(8) 0.0004(7) -0.0016(7) 0.0006(6) C7 0.0199(9) 0.0288(10) 0.0251(9) -0.0031(8) 0.0073(7) -0.0027(7) C8 0.0264(9) 0.0337(10) 0.0209(8) -0.0055(8) 0.0022(8) -0.0060(8) C9 0.0157(8) 0.0184(8) 0.0251(9) 0.0000(7) -0.0022(7) -0.0003(6) C10 0.0172(8) 0.0256(9) 0.0262(9) -0.0012(8) 0.0050(7) -0.0030(7) C11 0.0156(8) 0.0228(9) 0.0229(8) -0.0045(7) 0.0003(7) 0.0005(6) O12 0.0169(6) 0.0340(7) 0.0274(6) -0.0047(6) -0.0011(5) -0.0069(5) C13 0.0211(9) 0.0363(11) 0.0319(10) -0.0009(9) 0.0028(8) -0.0077(8) C14 0.0244(9) 0.0396(12) 0.0365(11) 0.0029(9) -0.0016(8) -0.0101(8) C15 0.0318(11) 0.0331(12) 0.0472(12) 0.0047(10) -0.0070(10) -0.0083(8) C16 0.0238(9) 0.0388(12) 0.0376(11) -0.0014(9) -0.0016(9) -0.0060(8) C17 0.0338(11) 0.0417(12) 0.0407(12) 0.0052(10) -0.0072(10) -0.0079(9) C18 0.0303(10) 0.0374(12) 0.0369(11) -0.0013(9) -0.0021(9) -0.0043(8) C19 0.0380(12) 0.0510(14) 0.0298(10) 0.0063(10) -0.0006(9) -0.0035(10) C20 0.0382(12) 0.0742(17) 0.0395(12) 0.0073(12) -0.0045(10) -0.0014(12) C21 0.0180(8) 0.0168(8) 0.0221(8) 0.0018(7) 0.0020(7) -0.0011(6) C22 0.0158(8) 0.0183(8) 0.0265(9) -0.0022(7) 0.0030(7) 0.0004(6) C23 0.0167(7) 0.0257(9) 0.0205(8) 0.0001(7) 0.0028(6) 0.0049(7) Br23 0.01879(8) 0.02634(10) 0.03322(10) -0.00089(8) 0.00081(7) 0.00694(7) C24 0.0295(10) 0.0188(9) 0.0274(9) 0.0019(7) 0.0050(8) 0.0051(7) C25 0.0255(9) 0.0184(9) 0.0409(11) 0.0017(8) 0.0009(8) -0.0031(7) C26 0.0187(8) 0.0239(10) 0.0352(10) 0.0027(8) -0.0003(8) -0.0024(7) C27 0.0156(8) 0.0150(8) 0.0331(9) 0.0019(7) 0.0017(7) -0.0009(6) C28 0.0258(9) 0.0265(10) 0.0301(10) 0.0005(8) 0.0070(8) 0.0064(7) C29 0.0254(9) 0.0306(10) 0.0309(10) 0.0070(8) 0.0020(8) 0.0015(8) Br29 0.05530(16) 0.07688(19) 0.03096(11) 0.01622(12) 0.00313(11) 0.02021(13) C30 0.0252(10) 0.0229(10) 0.0472(12) 0.0045(9) -0.0020(9) 0.0089(7) C31 0.0322(11) 0.0296(10) 0.0432(12) -0.0112(9) -0.0001(9) 0.0117(8) C32 0.0232(9) 0.0252(9) 0.0310(9) -0.0055(8) -0.0017(8) 0.0035(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.365(2) . ? N1 C2 1.377(2) . ? N1 C6 1.447(2) . ? C2 N3 1.316(2) . ? C2 C21 1.470(2) . ? N3 N4 1.3840(19) . ? N4 C5 1.318(2) . ? C5 C27 1.478(2) . ? C6 C11 1.370(2) . ? C6 C7 1.381(2) . ? C7 C8 1.381(2) . ? C8 C9 1.390(2) . ? C9 O12 1.3657(18) . ? C9 C10 1.389(2) . ? C10 C11 1.391(2) . ? O12 C13 1.442(2) . ? C13 C14 1.518(2) . ? C14 C15 1.490(3) . ? C15 C16 1.528(3) . ? C16 C17 1.524(3) . ? C17 C18 1.515(3) . ? C18 C19 1.516(3) . ? C19 C20 1.505(3) . ? C21 C26 1.394(2) . ? C21 C22 1.401(2) . ? C22 C23 1.378(2) . ? C23 C24 1.378(2) . ? C23 Br23 1.9015(15) . ? C24 C25 1.378(2) . ? C25 C26 1.383(2) . ? C27 C32 1.384(2) . ? C27 C28 1.384(2) . ? C28 C29 1.381(2) . ? C29 C30 1.373(3) . ? C29 Br29 1.8915(18) . ? C30 C31 1.382(3) . ? C31 C32 1.389(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 104.76(13) . . ? C5 N1 C6 124.03(13) . . ? C2 N1 C6 130.08(14) . . ? N3 C2 N1 109.43(14) . . ? N3 C2 C21 122.42(14) . . ? N1 C2 C21 128.14(15) . . ? C2 N3 N4 108.41(13) . . ? C5 N4 N3 106.40(13) . . ? N4 C5 N1 110.99(14) . . ? N4 C5 C27 124.38(15) . . ? N1 C5 C27 124.62(14) . . ? C11 C6 C7 120.99(15) . . ? C11 C6 N1 117.66(15) . . ? C7 C6 N1 121.31(14) . . ? C8 C7 C6 119.20(16) . . ? C7 C8 C9 120.36(16) . . ? O12 C9 C10 123.80(15) . . ? O12 C9 C8 116.11(15) . . ? C10 C9 C8 120.09(15) . . ? C9 C10 C11 119.03(16) . . ? C6 C11 C10 120.32(16) . . ? C9 O12 C13 117.72(13) . . ? O12 C13 C14 106.71(15) . . ? C15 C14 C13 112.98(17) . . ? C14 C15 C16 113.69(17) . . ? C17 C16 C15 113.21(17) . . ? C18 C17 C16 113.62(17) . . ? C17 C18 C19 113.38(17) . . ? C20 C19 C18 112.73(18) . . ? C26 C21 C22 118.73(15) . . ? C26 C21 C2 124.74(15) . . ? C22 C21 C2 116.48(14) . . ? C23 C22 C21 119.66(15) . . ? C24 C23 C22 121.78(15) . . ? C24 C23 Br23 119.92(12) . . ? C22 C23 Br23 118.30(12) . . ? C25 C24 C23 118.42(16) . . ? C24 C25 C26 121.37(16) . . ? C25 C26 C21 120.01(16) . . ? C32 C27 C28 120.41(16) . . ? C32 C27 C5 118.71(16) . . ? C28 C27 C5 120.86(16) . . ? C29 C28 C27 118.96(17) . . ? C30 C29 C28 121.53(17) . . ? C30 C29 Br29 118.66(14) . . ? C28 C29 Br29 119.80(14) . . ? C29 C30 C31 119.20(17) . . ? C30 C31 C32 120.29(18) . . ? C27 C32 C31 119.59(17) . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.803 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.066 #===END