data_2c _publ_contact_author 'Prof. Dr. Dietmar Stalke' _publ_contact_author_email dstalke@chemie.uni-goettingen.de loop_ _publ_author_name 'Gerald Schwab, Daniel Stern, Dietmar Stalke' _journal_name_full '?' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' _ccdc_compound_id 2c _audit_creation_method SHELXL-97 _chemical_name_systematic '9-Brom-10-diisopropylthiophosphorylanthracene' #; # ? #; _chemical_name_common 'Br(C14H8)(iPr2P=S)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Br P S' _chemical_formula_weight 405.32 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' 'P' 'P' 0.1023 0.0942 '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' '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.5951(12) _cell_length_b 11.0527(6) _cell_length_c 14.5479(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.0230(10) _cell_angle_gamma 90.00 _cell_volume 3628.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 28092 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.41 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 2.466 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS-2004/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex II with D8-Goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 65575 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.42 _reflns_number_total 7452 _reflns_number_gt 6881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.0-2' _computing_cell_refinement 'SAINT V7.23A' _computing_data_reduction 'SAINT V7.23A' _computing_structure_solution 'SHELXS in SHELXTL ver. 6.12' _computing_structure_refinement 'SHELXL in SHELXTL ver. 6.12' _computing_molecular_graphics 'XP in SHELXTL ver. 6.12' _computing_publication_material 'XP in SHELXTL ver. 6.12' _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^)+(0.0360P)^2^+2.5749P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7452 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0634 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.333562(8) -0.071800(17) 0.217234(13) 0.02334(6) Uani 1 1 d . . . Br2 Br 0.171181(8) 0.482413(18) 0.451320(13) 0.02382(6) Uani 1 1 d . . . C1 C 0.25832(7) -0.09701(15) 0.26648(12) 0.0150(3) Uani 1 1 d . . . C2 C 0.23965(7) -0.01915(15) 0.33466(11) 0.0147(3) Uani 1 1 d . . . C3 C 0.27870(8) 0.06571(15) 0.38116(12) 0.0188(4) Uani 1 1 d . . . H3A H 0.3183 0.0737 0.3629 0.023 Uiso 1 1 calc R . . C4 C 0.25983(8) 0.13478(16) 0.45100(12) 0.0207(4) Uani 1 1 d . . . H4A H 0.2863 0.1903 0.4815 0.025 Uiso 1 1 calc R . . C5 C 0.20086(8) 0.12448(16) 0.47863(12) 0.0200(4) Uani 1 1 d . . . H5A H 0.1884 0.1716 0.5287 0.024 Uiso 1 1 calc R . . C6 C 0.16170(8) 0.04775(16) 0.43413(11) 0.0160(3) Uani 1 1 d . . . H6A H 0.1222 0.0435 0.4532 0.019 Uiso 1 1 calc R . . C7 C 0.17867(7) -0.02648(14) 0.35938(11) 0.0130(3) Uani 1 1 d . . . C8 C 0.13912(7) -0.10782(14) 0.31254(11) 0.0114(3) Uani 1 1 d . . . C9 C 0.16321(7) -0.20159(14) 0.25889(11) 0.0121(3) Uani 1 1 d . . . C10 C 0.13055(7) -0.30745(15) 0.22969(11) 0.0143(3) Uani 1 1 d . . . H10A H 0.0909 -0.3167 0.2474 0.017 Uiso 1 1 calc R . . C11 C 0.15465(8) -0.39511(15) 0.17742(12) 0.0177(3) Uani 1 1 d . . . H11A H 0.1317 -0.4640 0.1595 0.021 Uiso 1 1 calc R . . C12 C 0.21356(8) -0.38444(16) 0.14957(12) 0.0194(4) Uani 1 1 d . . . H12A H 0.2298 -0.4452 0.1121 0.023 Uiso 1 1 calc R . . C13 C 0.24673(7) -0.28716(16) 0.17656(11) 0.0174(3) Uani 1 1 d . . . H13A H 0.2861 -0.2805 0.1573 0.021 Uiso 1 1 calc R . . C14 C 0.22388(7) -0.19457(15) 0.23319(11) 0.0136(3) Uani 1 1 d . . . C15 C 0.03818(7) -0.10168(14) 0.17990(10) 0.0117(3) Uani 1 1 d . . . H15A H 0.0501 -0.1854 0.1625 0.014 Uiso 1 1 calc R . . C16 C -0.02859(7) -0.08788(15) 0.15935(12) 0.0162(3) Uani 1 1 d . . . H16A H -0.0376 -0.0969 0.0931 0.024 Uiso 1 1 calc R . . H16B H -0.0413 -0.0077 0.1792 0.024 Uiso 1 1 calc R . . H16C H -0.0497 -0.1502 0.1926 0.024 Uiso 1 1 calc R . . C17 C 0.07247(8) -0.01114(16) 0.12341(11) 0.0172(3) Uani 1 1 d . . . H17A H 0.0613 -0.0216 0.0579 0.026 Uiso 1 1 calc R . . H17B H 0.1151 -0.0253 0.1339 0.026 Uiso 1 1 calc R . . H17C H 0.0630 0.0714 0.1423 0.026 Uiso 1 1 calc R . . C18 C 0.02180(7) -0.19636(15) 0.37096(11) 0.0141(3) Uani 1 1 d . . . H18A H 0.0185 -0.2716 0.3329 0.017 Uiso 1 1 calc R . . C19 C 0.05975(8) -0.22472(19) 0.45855(13) 0.0255(4) Uani 1 1 d . . . H19A H 0.0402 -0.2872 0.4939 0.038 Uiso 1 1 calc R . . H19B H 0.0646 -0.1512 0.4959 0.038 Uiso 1 1 calc R . . H19C H 0.0987 -0.2539 0.4419 0.038 Uiso 1 1 calc R . . C20 C -0.04071(8) -0.15911(17) 0.39596(12) 0.0194(4) Uani 1 1 d . . . H20A H -0.0583 -0.2238 0.4316 0.029 Uiso 1 1 calc R . . H20B H -0.0653 -0.1449 0.3395 0.029 Uiso 1 1 calc R . . H20C H -0.0385 -0.0848 0.4327 0.029 Uiso 1 1 calc R . . C22 C 0.23885(7) 0.47295(16) 0.37945(12) 0.0163(3) Uani 1 1 d . . . C23 C 0.24121(7) 0.38266(15) 0.31313(11) 0.0152(3) Uani 1 1 d . . . C24 C 0.19175(7) 0.30685(16) 0.28756(12) 0.0195(4) Uani 1 1 d . . . H24A H 0.1562 0.3148 0.3191 0.023 Uiso 1 1 calc R . . C25 C 0.19451(8) 0.22393(16) 0.21926(13) 0.0206(4) Uani 1 1 d . . . H25A H 0.1610 0.1749 0.2032 0.025 Uiso 1 1 calc R . . C26 C 0.24706(8) 0.21038(16) 0.17193(12) 0.0189(4) Uani 1 1 d . . . H26A H 0.2484 0.1532 0.1233 0.023 Uiso 1 1 calc R . . C27 C 0.29602(8) 0.27846(15) 0.19521(11) 0.0165(3) Uani 1 1 d . . . H27A H 0.3309 0.2674 0.1624 0.020 Uiso 1 1 calc R . . C28 C 0.29625(7) 0.36599(15) 0.26771(11) 0.0136(3) Uani 1 1 d . . . C29 C 0.34614(7) 0.43854(15) 0.29347(11) 0.0130(3) Uani 1 1 d . . . C30 C 0.33790(7) 0.54354(15) 0.34821(11) 0.0138(3) Uani 1 1 d . . . C31 C 0.38035(7) 0.63956(15) 0.35814(11) 0.0161(3) Uani 1 1 d . . . H31A H 0.4160 0.6339 0.3266 0.019 Uiso 1 1 calc R . . C32 C 0.37132(8) 0.73872(16) 0.41120(12) 0.0190(4) Uani 1 1 d . . . H32A H 0.4004 0.8008 0.4155 0.023 Uiso 1 1 calc R . . C33 C 0.31912(8) 0.75000(16) 0.45986(12) 0.0207(4) Uani 1 1 d . . . H33A H 0.3137 0.8182 0.4982 0.025 Uiso 1 1 calc R . . C34 C 0.27674(8) 0.66338(17) 0.45174(12) 0.0191(4) Uani 1 1 d . . . H34A H 0.2418 0.6717 0.4848 0.023 Uiso 1 1 calc R . . C35 C 0.28355(7) 0.55964(15) 0.39435(11) 0.0155(3) Uani 1 1 d . . . C36 C 0.45247(7) 0.49568(16) 0.18802(12) 0.0165(3) Uani 1 1 d . . . H36A H 0.4668 0.5695 0.2221 0.020 Uiso 1 1 calc R . . C37 C 0.40356(9) 0.5342(2) 0.11746(14) 0.0288(4) Uani 1 1 d . . . H37A H 0.4199 0.5904 0.0732 0.043 Uiso 1 1 calc R . . H37B H 0.3717 0.5743 0.1491 0.043 Uiso 1 1 calc R . . H37C H 0.3877 0.4627 0.0848 0.043 Uiso 1 1 calc R . . C38 C 0.50470(8) 0.44207(18) 0.13918(13) 0.0220(4) Uani 1 1 d . . . H38A H 0.5190 0.5012 0.0953 0.033 Uiso 1 1 calc R . . H38B H 0.4919 0.3685 0.1062 0.033 Uiso 1 1 calc R . . H38C H 0.5367 0.4221 0.1847 0.033 Uiso 1 1 calc R . . C39 C 0.46257(8) 0.41057(16) 0.38584(12) 0.0179(3) Uani 1 1 d . . . H39A H 0.4558 0.4956 0.4063 0.022 Uiso 1 1 calc R . . C40 C 0.52932(8) 0.3921(2) 0.37901(13) 0.0263(4) Uani 1 1 d . . . H40A H 0.5489 0.3965 0.4406 0.040 Uiso 1 1 calc R . . H40B H 0.5451 0.4553 0.3400 0.040 Uiso 1 1 calc R . . H40C H 0.5366 0.3126 0.3520 0.040 Uiso 1 1 calc R . . C41 C 0.43702(10) 0.3255(2) 0.45639(13) 0.0317(5) Uani 1 1 d . . . H41A H 0.4576 0.3384 0.5166 0.048 Uiso 1 1 calc R . . H41B H 0.4425 0.2414 0.4371 0.048 Uiso 1 1 calc R . . H41C H 0.3946 0.3420 0.4607 0.048 Uiso 1 1 calc R . . P1 P 0.058211(17) -0.07866(4) 0.30339(3) 0.00988(8) Uani 1 1 d . . . P2 P 0.422798(18) 0.38918(4) 0.27251(3) 0.01265(9) Uani 1 1 d . . . S1 S 0.034138(19) 0.08623(4) 0.33648(3) 0.01535(9) Uani 1 1 d . . . S2 S 0.432703(19) 0.21974(4) 0.23519(3) 0.02080(10) 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 Br1 0.01306(9) 0.02495(10) 0.03239(11) 0.00197(7) 0.00481(7) -0.00130(7) Br2 0.01369(9) 0.03259(11) 0.02590(10) 0.00130(8) 0.00778(7) 0.00023(7) C1 0.0094(7) 0.0171(8) 0.0183(8) 0.0053(6) 0.0012(6) 0.0012(6) C2 0.0145(8) 0.0127(8) 0.0165(8) 0.0038(6) -0.0023(6) -0.0008(6) C3 0.0158(8) 0.0168(8) 0.0233(9) 0.0041(7) -0.0049(7) -0.0024(7) C4 0.0234(9) 0.0163(8) 0.0214(9) 0.0006(7) -0.0090(7) -0.0052(7) C5 0.0281(9) 0.0163(8) 0.0151(8) -0.0018(7) -0.0039(7) -0.0012(7) C6 0.0187(8) 0.0154(8) 0.0137(8) 0.0017(6) -0.0008(6) 0.0000(7) C7 0.0156(8) 0.0111(7) 0.0120(7) 0.0025(6) -0.0017(6) 0.0004(6) C8 0.0119(7) 0.0112(7) 0.0112(7) 0.0025(6) 0.0006(6) -0.0003(6) C9 0.0126(7) 0.0124(8) 0.0111(7) 0.0026(6) -0.0007(6) 0.0015(6) C10 0.0134(8) 0.0133(8) 0.0161(8) 0.0019(6) 0.0000(6) 0.0012(6) C11 0.0198(8) 0.0131(8) 0.0198(8) -0.0022(7) -0.0022(7) 0.0005(7) C12 0.0222(9) 0.0188(8) 0.0174(8) -0.0031(7) 0.0019(7) 0.0067(7) C13 0.0155(8) 0.0201(9) 0.0169(8) 0.0016(7) 0.0039(6) 0.0048(7) C14 0.0145(8) 0.0141(8) 0.0123(7) 0.0030(6) 0.0002(6) 0.0033(6) C15 0.0139(8) 0.0109(7) 0.0103(7) -0.0008(6) -0.0002(6) 0.0016(6) C16 0.0144(8) 0.0171(8) 0.0168(8) -0.0011(6) -0.0027(6) 0.0013(6) C17 0.0199(8) 0.0190(8) 0.0128(8) 0.0017(6) 0.0014(6) -0.0027(7) C18 0.0154(8) 0.0113(7) 0.0161(8) 0.0011(6) 0.0060(6) -0.0002(6) C19 0.0238(9) 0.0315(10) 0.0216(9) 0.0144(8) 0.0047(7) 0.0037(8) C20 0.0166(8) 0.0212(9) 0.0210(9) 0.0011(7) 0.0075(7) -0.0011(7) C22 0.0109(7) 0.0214(9) 0.0169(8) 0.0056(7) 0.0032(6) 0.0033(6) C23 0.0118(8) 0.0163(8) 0.0172(8) 0.0067(7) -0.0010(6) 0.0001(6) C24 0.0124(8) 0.0209(9) 0.0251(9) 0.0077(7) -0.0012(6) -0.0005(7) C25 0.0171(8) 0.0179(8) 0.0259(9) 0.0071(7) -0.0081(7) -0.0046(7) C26 0.0232(9) 0.0149(8) 0.0179(8) 0.0029(7) -0.0067(7) -0.0010(7) C27 0.0168(8) 0.0160(8) 0.0164(8) 0.0028(6) -0.0025(6) 0.0011(6) C28 0.0125(7) 0.0134(8) 0.0149(8) 0.0041(6) -0.0005(6) 0.0003(6) C29 0.0118(7) 0.0150(8) 0.0123(7) 0.0025(6) 0.0014(6) 0.0010(6) C30 0.0134(8) 0.0150(8) 0.0130(7) 0.0022(6) 0.0000(6) 0.0013(6) C31 0.0153(8) 0.0171(8) 0.0162(8) 0.0013(6) 0.0026(6) -0.0006(6) C32 0.0222(9) 0.0169(8) 0.0178(8) 0.0002(7) 0.0018(7) -0.0038(7) C33 0.0269(9) 0.0183(9) 0.0169(8) -0.0031(7) 0.0020(7) 0.0032(7) C34 0.0183(8) 0.0229(9) 0.0166(8) 0.0005(7) 0.0042(6) 0.0041(7) C35 0.0144(8) 0.0177(8) 0.0144(8) 0.0026(6) 0.0016(6) 0.0020(6) C36 0.0151(8) 0.0178(8) 0.0169(8) -0.0002(7) 0.0046(6) -0.0015(6) C37 0.0248(10) 0.0378(11) 0.0242(10) 0.0140(8) 0.0064(8) 0.0072(9) C38 0.0176(9) 0.0287(10) 0.0203(9) -0.0039(7) 0.0075(7) -0.0001(7) C39 0.0164(8) 0.0223(9) 0.0148(8) -0.0008(7) -0.0015(6) 0.0030(7) C40 0.0170(9) 0.0368(11) 0.0244(10) -0.0048(8) -0.0065(7) 0.0064(8) C41 0.0342(11) 0.0406(12) 0.0200(9) 0.0099(9) -0.0023(8) -0.0023(9) P1 0.01097(19) 0.00899(18) 0.00977(18) -0.00030(14) 0.00127(14) 0.00052(14) P2 0.01098(19) 0.0130(2) 0.0139(2) -0.00036(15) 0.00040(15) 0.00074(15) S1 0.0195(2) 0.01049(19) 0.0160(2) -0.00276(15) 0.00037(15) 0.00381(15) S2 0.0192(2) 0.0142(2) 0.0287(2) -0.00367(17) -0.00178(17) 0.00359(16) _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 1.9000(16) . ? Br2 C22 1.9001(16) . ? C1 C2 1.395(2) . ? C1 C14 1.401(2) . ? C2 C3 1.433(2) . ? C2 C7 1.445(2) . ? C3 C4 1.357(3) . ? C4 C5 1.417(3) . ? C5 C6 1.364(2) . ? C6 C7 1.431(2) . ? C7 C8 1.417(2) . ? C8 C9 1.423(2) . ? C8 P1 1.8542(16) . ? C9 C10 1.436(2) . ? C9 C14 1.442(2) . ? C10 C11 1.363(2) . ? C11 C12 1.417(2) . ? C12 C13 1.357(3) . ? C13 C14 1.427(2) . ? C15 C16 1.530(2) . ? C15 C17 1.531(2) . ? C15 P1 1.8469(16) . ? C18 C19 1.530(2) . ? C18 C20 1.533(2) . ? C18 P1 1.8496(16) . ? C22 C23 1.391(3) . ? C22 C35 1.401(2) . ? C23 C24 1.430(2) . ? C23 C28 1.451(2) . ? C24 C25 1.356(3) . ? C25 C26 1.412(3) . ? C26 C27 1.366(2) . ? C27 C28 1.431(2) . ? C28 C29 1.418(2) . ? C29 C30 1.425(2) . ? C29 P2 1.8565(17) . ? C30 C31 1.433(2) . ? C30 C35 1.441(2) . ? C31 C32 1.362(2) . ? C32 C33 1.413(3) . ? C33 C34 1.355(3) . ? C34 C35 1.431(2) . ? C36 C37 1.529(2) . ? C36 C38 1.529(2) . ? C36 P2 1.8527(17) . ? C39 C41 1.528(3) . ? C39 C40 1.530(2) . ? C39 P2 1.8507(17) . ? P1 S1 1.9689(6) . ? P2 S2 1.9661(6) . ? 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 C1 C14 122.50(15) . . ? C2 C1 Br1 119.19(13) . . ? C14 C1 Br1 118.31(13) . . ? C1 C2 C3 122.53(16) . . ? C1 C2 C7 118.07(15) . . ? C3 C2 C7 119.39(15) . . ? C4 C3 C2 120.77(17) . . ? C3 C4 C5 120.30(16) . . ? C6 C5 C4 120.77(17) . . ? C5 C6 C7 121.61(16) . . ? C8 C7 C6 122.82(15) . . ? C8 C7 C2 120.10(15) . . ? C6 C7 C2 117.04(15) . . ? C7 C8 C9 118.45(14) . . ? C7 C8 P1 121.25(12) . . ? C9 C8 P1 119.44(12) . . ? C8 C9 C10 123.40(14) . . ? C8 C9 C14 119.96(14) . . ? C10 C9 C14 116.62(14) . . ? C11 C10 C9 122.02(15) . . ? C10 C11 C12 120.64(16) . . ? C13 C12 C11 119.75(16) . . ? C12 C13 C14 121.60(16) . . ? C1 C14 C13 122.69(15) . . ? C1 C14 C9 118.04(15) . . ? C13 C14 C9 119.27(15) . . ? C16 C15 C17 110.59(13) . . ? C16 C15 P1 111.40(11) . . ? C17 C15 P1 109.09(11) . . ? C19 C18 C20 109.89(14) . . ? C19 C18 P1 109.95(12) . . ? C20 C18 P1 112.23(11) . . ? C23 C22 C35 122.98(15) . . ? C23 C22 Br2 118.85(13) . . ? C35 C22 Br2 118.15(13) . . ? C22 C23 C24 122.87(16) . . ? C22 C23 C28 118.18(15) . . ? C24 C23 C28 118.95(16) . . ? C25 C24 C23 121.42(16) . . ? C24 C25 C26 120.11(16) . . ? C27 C26 C25 120.78(17) . . ? C26 C27 C28 121.79(16) . . ? C29 C28 C27 123.32(15) . . ? C29 C28 C23 119.77(15) . . ? C27 C28 C23 116.85(15) . . ? C28 C29 C30 118.87(15) . . ? C28 C29 P2 121.75(12) . . ? C30 C29 P2 118.79(12) . . ? C29 C30 C31 123.57(15) . . ? C29 C30 C35 120.03(15) . . ? C31 C30 C35 116.36(15) . . ? C32 C31 C30 122.25(16) . . ? C31 C32 C33 120.60(16) . . ? C34 C33 C32 119.92(16) . . ? C33 C34 C35 121.31(16) . . ? C22 C35 C34 122.63(16) . . ? C22 C35 C30 117.95(15) . . ? C34 C35 C30 119.41(15) . . ? C37 C36 C38 110.14(15) . . ? C37 C36 P2 110.40(12) . . ? C38 C36 P2 112.16(12) . . ? C41 C39 C40 111.72(16) . . ? C41 C39 P2 109.69(13) . . ? C40 C39 P2 111.04(12) . . ? C15 P1 C18 109.09(7) . . ? C15 P1 C8 103.65(7) . . ? C18 P1 C8 107.70(7) . . ? C15 P1 S1 107.98(5) . . ? C18 P1 S1 112.62(5) . . ? C8 P1 S1 115.30(5) . . ? C39 P2 C36 109.52(8) . . ? C39 P2 C29 103.27(8) . . ? C36 P2 C29 107.19(7) . . ? C39 P2 S2 108.10(6) . . ? C36 P2 S2 111.81(6) . . ? C29 P2 S2 116.49(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 167.81(16) . . . . ? Br1 C1 C2 C3 -11.5(2) . . . . ? C14 C1 C2 C7 -11.4(2) . . . . ? Br1 C1 C2 C7 169.28(11) . . . . ? C1 C2 C3 C4 -175.95(16) . . . . ? C7 C2 C3 C4 3.2(2) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 C8 179.35(16) . . . . ? C5 C6 C7 C2 1.7(2) . . . . ? C1 C2 C7 C8 -2.3(2) . . . . ? C3 C2 C7 C8 178.47(15) . . . . ? C1 C2 C7 C6 175.45(15) . . . . ? C3 C2 C7 C6 -3.8(2) . . . . ? C6 C7 C8 C9 -161.86(15) . . . . ? C2 C7 C8 C9 15.7(2) . . . . ? C6 C7 C8 P1 28.9(2) . . . . ? C2 C7 C8 P1 -153.51(12) . . . . ? C7 C8 C9 C10 162.14(15) . . . . ? P1 C8 C9 C10 -28.4(2) . . . . ? C7 C8 C9 C14 -16.2(2) . . . . ? P1 C8 C9 C14 153.26(12) . . . . ? C8 C9 C10 C11 179.24(16) . . . . ? C14 C9 C10 C11 -2.4(2) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 1.2(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C2 C1 C14 C13 -168.08(16) . . . . ? Br1 C1 C14 C13 11.2(2) . . . . ? C2 C1 C14 C9 10.9(2) . . . . ? Br1 C1 C14 C9 -169.73(11) . . . . ? C12 C13 C14 C1 176.10(16) . . . . ? C12 C13 C14 C9 -2.9(2) . . . . ? C8 C9 C14 C1 3.2(2) . . . . ? C10 C9 C14 C1 -175.25(14) . . . . ? C8 C9 C14 C13 -177.75(14) . . . . ? C10 C9 C14 C13 3.8(2) . . . . ? C35 C22 C23 C24 -169.48(16) . . . . ? Br2 C22 C23 C24 8.9(2) . . . . ? C35 C22 C23 C28 10.0(2) . . . . ? Br2 C22 C23 C28 -171.68(11) . . . . ? C22 C23 C24 C25 176.48(16) . . . . ? C28 C23 C24 C25 -3.0(2) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C24 C25 C26 C27 1.3(3) . . . . ? C25 C26 C27 C28 -0.2(3) . . . . ? C26 C27 C28 C29 -179.73(16) . . . . ? C26 C27 C28 C23 -2.4(2) . . . . ? C22 C23 C28 C29 1.8(2) . . . . ? C24 C23 C28 C29 -178.68(15) . . . . ? C22 C23 C28 C27 -175.60(15) . . . . ? C24 C23 C28 C27 3.9(2) . . . . ? C27 C28 C29 C30 163.48(15) . . . . ? C23 C28 C29 C30 -13.8(2) . . . . ? C27 C28 C29 P2 -25.5(2) . . . . ? C23 C28 C29 P2 157.24(12) . . . . ? C28 C29 C30 C31 -162.93(15) . . . . ? P2 C29 C30 C31 25.8(2) . . . . ? C28 C29 C30 C35 14.6(2) . . . . ? P2 C29 C30 C35 -156.73(12) . . . . ? C29 C30 C31 C32 -179.80(16) . . . . ? C35 C30 C31 C32 2.6(2) . . . . ? C30 C31 C32 C33 0.6(3) . . . . ? C31 C32 C33 C34 -2.0(3) . . . . ? C32 C33 C34 C35 -0.1(3) . . . . ? C23 C22 C35 C34 169.63(16) . . . . ? Br2 C22 C35 C34 -8.7(2) . . . . ? C23 C22 C35 C30 -9.2(2) . . . . ? Br2 C22 C35 C30 172.41(12) . . . . ? C33 C34 C35 C22 -175.40(17) . . . . ? C33 C34 C35 C30 3.4(3) . . . . ? C29 C30 C35 C22 -3.3(2) . . . . ? C31 C30 C35 C22 174.34(15) . . . . ? C29 C30 C35 C34 177.78(15) . . . . ? C31 C30 C35 C34 -4.6(2) . . . . ? C16 C15 P1 C18 62.45(13) . . . . ? C17 C15 P1 C18 -175.19(11) . . . . ? C16 C15 P1 C8 176.98(11) . . . . ? C17 C15 P1 C8 -60.66(12) . . . . ? C16 C15 P1 S1 -60.26(12) . . . . ? C17 C15 P1 S1 62.10(12) . . . . ? C19 C18 P1 C15 149.82(12) . . . . ? C20 C18 P1 C15 -87.54(13) . . . . ? C19 C18 P1 C8 37.94(14) . . . . ? C20 C18 P1 C8 160.58(12) . . . . ? C19 C18 P1 S1 -90.30(12) . . . . ? C20 C18 P1 S1 32.33(13) . . . . ? C7 C8 P1 C15 131.36(13) . . . . ? C9 C8 P1 C15 -37.80(14) . . . . ? C7 C8 P1 C18 -113.13(13) . . . . ? C9 C8 P1 C18 77.72(14) . . . . ? C7 C8 P1 S1 13.57(15) . . . . ? C9 C8 P1 S1 -155.59(11) . . . . ? C41 C39 P2 C36 178.37(13) . . . . ? C40 C39 P2 C36 -57.67(15) . . . . ? C41 C39 P2 C29 64.42(14) . . . . ? C40 C39 P2 C29 -171.62(13) . . . . ? C41 C39 P2 S2 -59.59(14) . . . . ? C40 C39 P2 S2 64.38(14) . . . . ? C37 C36 P2 C39 -147.61(13) . . . . ? C38 C36 P2 C39 89.14(14) . . . . ? C37 C36 P2 C29 -36.22(15) . . . . ? C38 C36 P2 C29 -159.46(12) . . . . ? C37 C36 P2 S2 92.59(13) . . . . ? C38 C36 P2 S2 -30.65(14) . . . . ? C28 C29 P2 C39 -129.72(14) . . . . ? C30 C29 P2 C39 41.31(15) . . . . ? C28 C29 P2 C36 114.66(14) . . . . ? C30 C29 P2 C36 -74.31(14) . . . . ? C28 C29 P2 S2 -11.41(15) . . . . ? C30 C29 P2 S2 159.62(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.404 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.058