# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_General _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #------------------------------------------------------------------------------ # SUBMISSION DETAILS _publ_contact_author_name 'Masaaki Yoshifuji' _publ_contact_author_address ; Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai, 980-8578, Japan ; _publ_contact_author_email 'yoshifj@mail.cc.tohoku.ac.jp' _publ_contact_author_fax '81-22-217-6562' _publ_contact_author_phone '81-22-217-6558' _publ_contact_letter ; ; #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; Development of a New Sterically Protecting Auxiliary of the Metacyclophane Type and Application to Unsymmetrical Diphosphene, 1,3-Diphosphaallene, and 1,4-Diphosphabutatriene ; _publ_section_title_footnote ; ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Kozo Toyota' ; ; ; Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai, 980-8578, Japan ; 'Akitake Nakamura' ; ; ; Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai, 980-8578, Japan ; 'Yoshifuji Masaaki' ; ; ; Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai, 980-8578, Japan ; _publ_section_synopsis ; ; #------------------------------------------------------------------------------ data_17-[(2,4,6-tri-t-butylphenyl)phosphinidenephosphino] _database_code_CSD 193025 # TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_acknowledgements ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; #------------------------------------------------------------------------------ _audit_creation_date 'Sat Sep 7 17:10:42 2002' _audit_creation_method 'by teXsan' _audit_update_record ? _chemical_name_systematic ; 1,1,11,11-tetramethyl-17-[(2,4,6-tri-t-butylphenyl) phosphinidenephosphino]-[11]-metacyclophane ; #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C39 H62 P2 ' _chemical_formula_moiety 'C39 H62 P2 ' _chemical_formula_weight 592.87 _chemical_melting_point 162-165 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 15.398(2) _cell_length_b 23.597(5) _cell_length_c 10.236(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3719(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 173.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.059 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0.010000 _diffrn_reflns_number 3211 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 25.01 _diffrn_measured_fraction_theta_max 0.8678 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.8678 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3205 _reflns_number_gt 2997 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1391 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3205 _refine_ls_number_parameters 371 _refine_ls_goodness_of_fit_ref 1.717 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0690 _refine_diff_density_max 0.21 _refine_diff_density_min -0.29 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack 0.3(1) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'P' 'P' 0.102 0.094 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P(1) P 0.60265(5) 0.19908(4) 0.59763(10) 0.0322(2) Uani 1.00 d . . . P(2) P 0.66530(5) 0.12297(4) 0.6007(1) 0.0382(2) Uani 1.00 d . . . C(1) C 0.6948(2) 0.2489(1) 0.5715(3) 0.0316(8) Uani 1.00 d . . . C(2) C 0.7609(2) 0.2591(2) 0.6674(4) 0.0358(9) Uani 1.00 d . . . C(3) C 0.8389(2) 0.2834(2) 0.6243(4) 0.0424(9) Uani 1.00 d . . . C(4) C 0.8513(2) 0.2991(2) 0.4971(4) 0.0454(9) Uani 1.00 d . . . C(5) C 0.7831(2) 0.2959(2) 0.4102(4) 0.0431(10) Uani 1.00 d . . . C(6) C 0.7025(2) 0.2732(1) 0.4445(4) 0.0361(8) Uani 1.00 d . . . C(7) C 0.7533(2) 0.2477(2) 0.8168(4) 0.0418(9) Uani 1.00 d . . . C(8) C 0.7925(2) 0.1891(2) 0.8520(4) 0.050(1) Uani 1.00 d . . . C(9) C 0.8065(3) 0.2920(2) 0.8945(5) 0.059(1) Uani 1.00 d . . . C(10) C 0.6600(2) 0.2519(2) 0.8692(3) 0.0365(9) Uani 1.00 d . . . C(11) C 0.6139(2) 0.3086(2) 0.8523(4) 0.0426(10) Uani 1.00 d . . . C(12) C 0.5176(2) 0.3057(2) 0.8937(5) 0.047(1) Uani 1.00 d . . . C(13) C 0.4699(3) 0.3625(2) 0.8819(5) 0.056(1) Uani 1.00 d . . . C(14) C 0.4721(3) 0.3885(2) 0.7459(5) 0.055(1) Uani 1.00 d . . . C(15) C 0.4299(2) 0.3522(2) 0.6391(5) 0.055(1) Uani 1.00 d . . . C(16) C 0.4472(3) 0.3739(2) 0.5003(5) 0.059(1) Uani 1.00 d . . . C(17) C 0.5373(3) 0.3589(2) 0.4481(5) 0.051(1) Uani 1.00 d . . . C(18) C 0.5413(2) 0.2978(2) 0.3975(4) 0.0468(10) Uani 1.00 d . . . C(19) C 0.6282(3) 0.2758(2) 0.3408(4) 0.047(1) Uani 1.00 d . . . C(20) C 0.6127(3) 0.2173(2) 0.2758(4) 0.061(1) Uani 1.00 d . . . C(21) C 0.6524(3) 0.3174(2) 0.2282(4) 0.058(1) Uani 1.00 d . . . C(22) C 0.5681(2) 0.0765(1) 0.5883(4) 0.0320(8) Uani 1.00 d . . . C(23) C 0.4974(2) 0.0775(1) 0.6776(4) 0.0282(7) Uani 1.00 d . . . C(24) C 0.4159(2) 0.0613(1) 0.6299(4) 0.0338(8) Uani 1.00 d . . . C(25) C 0.4021(2) 0.0417(1) 0.5052(4) 0.0341(8) Uani 1.00 d . . . C(26) C 0.4753(2) 0.0309(1) 0.4283(4) 0.0385(9) Uani 1.00 d . . . C(27) C 0.5585(2) 0.0452(1) 0.4684(4) 0.0352(9) Uani 1.00 d . . . C(28) C 0.5029(2) 0.0894(1) 0.8258(4) 0.0320(8) Uani 1.00 d . . . C(29) C 0.5950(2) 0.0929(2) 0.8792(4) 0.043(1) Uani 1.00 d . . . C(30) C 0.4532(2) 0.1432(2) 0.8629(4) 0.0384(10) Uani 1.00 d . . . C(31) C 0.4611(2) 0.0389(2) 0.8988(4) 0.047(1) Uani 1.00 d . . . C(32) C 0.3118(2) 0.0272(2) 0.4500(4) 0.0417(9) Uani 1.00 d . . . C(33) C 0.2990(3) 0.0568(2) 0.3185(5) 0.058(1) Uani 1.00 d . . . C(34) C 0.2385(2) 0.0467(2) 0.5398(5) 0.051(1) Uani 1.00 d . . . C(35) C 0.3048(3) -0.0373(2) 0.4314(5) 0.054(1) Uani 1.00 d . . . C(36) C 0.6374(2) 0.0245(2) 0.3854(4) 0.050(1) Uani 1.00 d . . . C(37) C 0.6775(3) 0.0710(2) 0.3023(5) 0.069(2) Uani 1.00 d . . . C(38) C 0.7056(3) -0.0023(2) 0.4762(6) 0.074(2) Uani 1.00 d . . . C(39) C 0.6092(3) -0.0227(2) 0.2884(5) 0.064(1) Uani 1.00 d . . . H(1) H 0.8846 0.2895 0.6863 0.0511 Uiso 1.00 calc . . . H(2) H 0.9068 0.3119 0.4686 0.0543 Uiso 1.00 calc . . . H(3) H 0.7914 0.3095 0.3237 0.0521 Uiso 1.00 calc . . . H(4) H 0.7735 0.1617 0.7900 0.0603 Uiso 1.00 calc . . . H(5) H 0.8541 0.1914 0.8500 0.0603 Uiso 1.00 calc . . . H(6) H 0.7739 0.1783 0.9367 0.0603 Uiso 1.00 calc . . . H(7) H 0.7889 0.3291 0.8693 0.0700 Uiso 1.00 calc . . . H(8) H 0.8664 0.2872 0.8761 0.0700 Uiso 1.00 calc . . . H(9) H 0.7965 0.2871 0.9852 0.0700 Uiso 1.00 calc . . . H(10) H 0.6263 0.2239 0.8257 0.0441 Uiso 1.00 calc . . . H(11) H 0.6616 0.2437 0.9601 0.0441 Uiso 1.00 calc . . . H(12) H 0.6170 0.3195 0.7628 0.0513 Uiso 1.00 calc . . . H(13) H 0.6426 0.3363 0.9042 0.0513 Uiso 1.00 calc . . . H(14) H 0.4887 0.2789 0.8394 0.0567 Uiso 1.00 calc . . . H(15) H 0.5147 0.2936 0.9819 0.0567 Uiso 1.00 calc . . . H(16) H 0.4110 0.3567 0.9059 0.0667 Uiso 1.00 calc . . . H(17) H 0.4961 0.3883 0.9413 0.0667 Uiso 1.00 calc . . . H(18) H 0.4423 0.4239 0.7496 0.0661 Uiso 1.00 calc . . . H(19) H 0.5310 0.3950 0.7230 0.0661 Uiso 1.00 calc . . . H(20) H 0.3689 0.3516 0.6532 0.0668 Uiso 1.00 calc . . . H(21) H 0.4522 0.3147 0.6460 0.0668 Uiso 1.00 calc . . . H(22) H 0.4051 0.3579 0.4435 0.0713 Uiso 1.00 calc . . . H(23) H 0.4415 0.4140 0.5005 0.0713 Uiso 1.00 calc . . . H(24) H 0.5515 0.3841 0.3788 0.0608 Uiso 1.00 calc . . . H(25) H 0.5786 0.3632 0.5166 0.0608 Uiso 1.00 calc . . . H(26) H 0.4989 0.2946 0.3301 0.0564 Uiso 1.00 calc . . . H(27) H 0.5260 0.2737 0.4679 0.0564 Uiso 1.00 calc . . . H(28) H 0.5663 0.2200 0.2149 0.0722 Uiso 1.00 calc . . . H(29) H 0.6640 0.2055 0.2316 0.0722 Uiso 1.00 calc . . . H(30) H 0.5984 0.1901 0.3411 0.0722 Uiso 1.00 calc . . . H(31) H 0.6079 0.3167 0.1638 0.0695 Uiso 1.00 calc . . . H(32) H 0.7057 0.3061 0.1902 0.0695 Uiso 1.00 calc . . . H(33) H 0.6577 0.3547 0.2622 0.0695 Uiso 1.00 calc . . . H(34) H 0.3673 0.0639 0.6875 0.0406 Uiso 1.00 calc . . . H(35) H 0.4680 0.0130 0.3456 0.0460 Uiso 1.00 calc . . . H(36) H 0.5935 0.0935 0.9718 0.0520 Uiso 1.00 calc . . . H(37) H 0.6274 0.0609 0.8504 0.0520 Uiso 1.00 calc . . . H(38) H 0.6219 0.1266 0.8480 0.0520 Uiso 1.00 calc . . . H(39) H 0.4599 0.1500 0.9538 0.0463 Uiso 1.00 calc . . . H(40) H 0.3935 0.1383 0.8430 0.0463 Uiso 1.00 calc . . . H(41) H 0.4759 0.1742 0.8150 0.0463 Uiso 1.00 calc . . . H(42) H 0.4614 0.0461 0.9898 0.0564 Uiso 1.00 calc . . . H(43) H 0.4030 0.0340 0.8695 0.0564 Uiso 1.00 calc . . . H(44) H 0.4934 0.0054 0.8810 0.0564 Uiso 1.00 calc . . . H(45) H 0.3018 0.0967 0.3307 0.0699 Uiso 1.00 calc . . . H(46) H 0.2441 0.0469 0.2834 0.0699 Uiso 1.00 calc . . . H(47) H 0.3436 0.0454 0.2599 0.0699 Uiso 1.00 calc . . . H(48) H 0.2449 0.0860 0.5574 0.0612 Uiso 1.00 calc . . . H(49) H 0.2412 0.0261 0.6197 0.0612 Uiso 1.00 calc . . . H(50) H 0.1842 0.0400 0.4988 0.0612 Uiso 1.00 calc . . . H(51) H 0.3291 -0.0559 0.5052 0.0646 Uiso 1.00 calc . . . H(52) H 0.2453 -0.0475 0.4233 0.0646 Uiso 1.00 calc . . . H(53) H 0.3352 -0.0481 0.3550 0.0646 Uiso 1.00 calc . . . H(54) H 0.7060 0.0976 0.3571 0.0839 Uiso 1.00 calc . . . H(55) H 0.6330 0.0898 0.2542 0.0839 Uiso 1.00 calc . . . H(56) H 0.7182 0.0550 0.2433 0.0839 Uiso 1.00 calc . . . H(57) H 0.7247 0.0253 0.5373 0.0885 Uiso 1.00 calc . . . H(58) H 0.6811 -0.0335 0.5205 0.0885 Uiso 1.00 calc . . . H(59) H 0.7538 -0.0146 0.4251 0.0885 Uiso 1.00 calc . . . H(60) H 0.5841 -0.0534 0.3350 0.0771 Uiso 1.00 calc . . . H(61) H 0.5674 -0.0078 0.2288 0.0771 Uiso 1.00 calc . . . H(62) H 0.6583 -0.0357 0.2410 0.0771 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P(1) 0.0306(4) 0.0385(4) 0.0275(5) -0.0075(4) -0.0008(4) 0.0012(4) P(2) 0.0278(4) 0.0474(5) 0.0394(6) -0.0017(4) 0.0041(4) -0.0079(5) C(1) 0.034(1) 0.033(2) 0.027(2) -0.007(1) 0.003(1) -0.005(1) C(2) 0.030(1) 0.042(2) 0.035(2) -0.005(1) 0.001(1) -0.007(2) C(3) 0.028(1) 0.042(2) 0.057(2) -0.003(1) 0.001(2) 0.000(2) C(4) 0.035(2) 0.041(2) 0.060(2) 0.001(2) 0.021(1) 0.004(2) C(5) 0.048(2) 0.041(2) 0.040(2) -0.004(2) 0.019(1) 0.004(2) C(6) 0.044(2) 0.036(2) 0.028(2) -0.002(2) 0.007(1) -0.006(1) C(7) 0.037(2) 0.055(2) 0.034(2) -0.007(2) -0.002(2) -0.008(2) C(8) 0.034(2) 0.068(2) 0.048(3) 0.002(2) -0.011(2) 0.008(2) C(9) 0.051(2) 0.077(3) 0.048(3) -0.021(2) -0.010(2) -0.019(2) C(10) 0.040(2) 0.043(2) 0.026(2) -0.008(2) 0.001(1) -0.009(1) C(11) 0.049(2) 0.044(2) 0.035(2) -0.002(2) 0.007(2) -0.008(2) C(12) 0.053(2) 0.046(2) 0.042(2) -0.003(2) 0.012(2) 0.004(2) C(13) 0.060(2) 0.047(2) 0.060(3) 0.004(2) 0.023(2) -0.001(2) C(14) 0.055(2) 0.046(2) 0.062(3) 0.009(2) 0.011(2) 0.007(2) C(15) 0.042(2) 0.058(2) 0.066(3) 0.000(2) 0.002(2) 0.011(2) C(16) 0.052(2) 0.065(3) 0.061(3) 0.003(2) -0.014(2) 0.012(2) C(17) 0.056(2) 0.050(2) 0.046(3) -0.006(2) -0.010(2) 0.013(2) C(18) 0.051(2) 0.052(2) 0.037(2) -0.014(2) -0.019(2) 0.012(2) C(19) 0.060(2) 0.055(2) 0.026(2) -0.018(2) -0.005(1) 0.000(1) C(20) 0.090(3) 0.061(2) 0.031(3) -0.022(3) -0.004(2) -0.008(2) C(21) 0.083(3) 0.065(3) 0.028(2) -0.022(2) -0.005(2) 0.009(2) C(22) 0.034(1) 0.035(2) 0.027(2) 0.004(1) 0.001(1) 0.000(1) C(23) 0.027(1) 0.025(2) 0.033(2) 0.004(1) 0.001(1) 0.002(1) C(24) 0.033(1) 0.033(2) 0.036(2) -0.003(1) 0.003(1) 0.000(1) C(25) 0.035(1) 0.029(2) 0.039(2) -0.002(1) -0.006(1) -0.003(1) C(26) 0.048(2) 0.036(2) 0.032(2) -0.003(2) -0.001(1) -0.006(2) C(27) 0.041(1) 0.035(2) 0.029(2) 0.005(1) 0.005(1) -0.003(1) C(28) 0.033(1) 0.034(2) 0.030(2) 0.005(1) -0.001(1) -0.001(1) C(29) 0.038(2) 0.064(2) 0.028(2) 0.008(2) -0.005(2) 0.002(2) C(30) 0.046(2) 0.038(2) 0.031(2) 0.007(2) 0.003(2) -0.005(1) C(31) 0.059(2) 0.045(2) 0.036(2) -0.010(2) 0.005(2) 0.009(2) C(32) 0.042(2) 0.035(2) 0.048(2) -0.002(2) -0.014(1) -0.008(2) C(33) 0.068(3) 0.057(3) 0.048(3) 0.001(2) -0.023(2) -0.002(2) C(34) 0.034(2) 0.048(2) 0.071(3) -0.003(2) -0.009(2) -0.007(2) C(35) 0.054(2) 0.037(2) 0.070(3) -0.006(2) -0.009(2) -0.013(2) C(36) 0.052(2) 0.058(2) 0.039(2) 0.007(2) 0.017(2) -0.016(1) C(37) 0.086(3) 0.062(3) 0.059(3) -0.019(3) 0.038(3) -0.021(2) C(38) 0.063(3) 0.088(3) 0.070(4) 0.045(3) -0.002(2) -0.024(3) C(39) 0.072(3) 0.064(3) 0.057(3) -0.002(2) 0.024(3) -0.028(2) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS' _computing_cell_refinement 'PROCESS' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag P(1) P(2) 2.039(2) . . yes P(1) C(1) 1.861(4) . . yes P(2) C(22) 1.861(4) . . yes C(1) C(2) 1.435(6) . . yes C(1) C(6) 1.426(7) . . yes C(2) C(3) 1.402(6) . . yes C(2) C(7) 1.558(8) . . yes C(3) C(4) 1.367(8) . . yes C(4) C(5) 1.378(8) . . yes C(5) C(6) 1.396(6) . . yes C(6) C(19) 1.561(7) . . yes C(7) C(8) 1.552(8) . . yes C(7) C(9) 1.548(7) . . yes C(7) C(10) 1.536(6) . . yes C(10) C(11) 1.526(7) . . yes C(11) C(12) 1.543(7) . . yes C(12) C(13) 1.533(7) . . yes C(13) C(14) 1.522(9) . . yes C(14) C(15) 1.533(9) . . yes C(15) C(16) 1.533(9) . . yes C(16) C(17) 1.529(8) . . yes C(17) C(18) 1.533(8) . . yes C(18) C(19) 1.549(8) . . yes C(19) C(20) 1.551(8) . . yes C(19) C(21) 1.559(7) . . yes C(22) C(23) 1.422(6) . . yes C(22) C(27) 1.440(7) . . yes C(23) C(24) 1.398(6) . . yes C(23) C(28) 1.545(7) . . yes C(24) C(25) 1.375(7) . . yes C(25) C(26) 1.399(7) . . yes C(25) C(32) 1.539(6) . . yes C(26) C(27) 1.387(6) . . yes C(27) C(36) 1.560(6) . . yes C(28) C(29) 1.522(6) . . yes C(28) C(30) 1.529(6) . . yes C(28) C(31) 1.546(7) . . yes C(32) C(33) 1.529(8) . . yes C(32) C(34) 1.526(7) . . yes C(32) C(35) 1.539(7) . . yes C(36) C(37) 1.520(8) . . yes C(36) C(38) 1.538(9) . . yes C(36) C(39) 1.554(8) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P(2) P(1) C(1) 101.4(1) . 1_555 1_555 yes P(1) P(2) C(22) 97.9(1) . 1_555 1_555 yes P(1) C(1) C(2) 123.3(4) . 1_555 1_555 yes P(1) C(1) C(6) 116.7(3) . 1_555 1_555 yes C(2) C(1) C(6) 119.7(4) . 1_555 1_555 yes C(1) C(2) C(3) 117.5(4) . 1_555 1_555 yes C(1) C(2) C(7) 126.1(4) . 1_555 1_555 yes C(3) C(2) C(7) 116.4(4) . 1_555 1_555 yes C(2) C(3) C(4) 122.0(5) . 1_555 1_555 yes C(3) C(4) C(5) 119.6(4) . 1_555 1_555 yes C(4) C(5) C(6) 122.4(5) . 1_555 1_555 yes C(1) C(6) C(5) 117.2(4) . 1_555 1_555 yes C(1) C(6) C(19) 125.0(4) . 1_555 1_555 yes C(5) C(6) C(19) 117.7(4) . 1_555 1_555 yes C(2) C(7) C(8) 110.6(4) . 1_555 1_555 yes C(2) C(7) C(9) 110.4(4) . 1_555 1_555 yes C(2) C(7) C(10) 113.7(4) . 1_555 1_555 yes C(8) C(7) C(9) 106.0(4) . 1_555 1_555 yes C(8) C(7) C(10) 109.9(4) . 1_555 1_555 yes C(9) C(7) C(10) 105.9(4) . 1_555 1_555 yes C(7) C(10) C(11) 116.8(4) . 1_555 1_555 yes C(10) C(11) C(12) 112.1(4) . 1_555 1_555 yes C(11) C(12) C(13) 113.6(4) . 1_555 1_555 yes C(12) C(13) C(14) 114.5(5) . 1_555 1_555 yes C(13) C(14) C(15) 114.7(5) . 1_555 1_555 yes C(14) C(15) C(16) 113.6(5) . 1_555 1_555 yes C(15) C(16) C(17) 113.8(5) . 1_555 1_555 yes C(16) C(17) C(18) 111.8(5) . 1_555 1_555 yes C(17) C(18) C(19) 118.4(4) . 1_555 1_555 yes C(6) C(19) C(18) 113.0(4) . 1_555 1_555 yes C(6) C(19) C(20) 111.7(5) . 1_555 1_555 yes C(6) C(19) C(21) 110.6(4) . 1_555 1_555 yes C(18) C(19) C(20) 109.1(4) . 1_555 1_555 yes C(18) C(19) C(21) 105.8(5) . 1_555 1_555 yes C(20) C(19) C(21) 106.2(5) . 1_555 1_555 yes P(2) C(22) C(23) 124.2(3) . 1_555 1_555 yes P(2) C(22) C(27) 116.2(3) . 1_555 1_555 yes C(23) C(22) C(27) 118.6(4) . 1_555 1_555 yes C(22) C(23) C(24) 117.2(4) . 1_555 1_555 yes C(22) C(23) C(28) 126.3(4) . 1_555 1_555 yes C(24) C(23) C(28) 116.2(4) . 1_555 1_555 yes C(23) C(24) C(25) 123.7(4) . 1_555 1_555 yes C(24) C(25) C(26) 117.4(4) . 1_555 1_555 yes C(24) C(25) C(32) 123.8(4) . 1_555 1_555 yes C(26) C(25) C(32) 118.7(4) . 1_555 1_555 yes C(25) C(26) C(27) 122.2(4) . 1_555 1_555 yes C(22) C(27) C(26) 118.1(4) . 1_555 1_555 yes C(22) C(27) C(36) 123.1(4) . 1_555 1_555 yes C(26) C(27) C(36) 118.8(4) . 1_555 1_555 yes C(23) C(28) C(29) 114.5(4) . 1_555 1_555 yes C(23) C(28) C(30) 111.5(4) . 1_555 1_555 yes C(23) C(28) C(31) 108.1(4) . 1_555 1_555 yes C(29) C(28) C(30) 109.4(4) . 1_555 1_555 yes C(29) C(28) C(31) 104.9(4) . 1_555 1_555 yes C(30) C(28) C(31) 108.1(4) . 1_555 1_555 yes C(25) C(32) C(33) 109.8(4) . 1_555 1_555 yes C(25) C(32) C(34) 112.4(4) . 1_555 1_555 yes C(25) C(32) C(35) 109.2(4) . 1_555 1_555 yes C(33) C(32) C(34) 107.3(4) . 1_555 1_555 yes C(33) C(32) C(35) 109.5(4) . 1_555 1_555 yes C(34) C(32) C(35) 108.6(4) . 1_555 1_555 yes C(27) C(36) C(37) 113.3(4) . 1_555 1_555 yes C(27) C(36) C(38) 109.4(5) . 1_555 1_555 yes C(27) C(36) C(39) 110.8(4) . 1_555 1_555 yes C(37) C(36) C(38) 110.9(5) . 1_555 1_555 yes C(37) C(36) C(39) 105.8(5) . 1_555 1_555 yes C(38) C(36) C(39) 106.4(5) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 P(1) P(2) C(22) C(23) -57.1(4) 1_555 1_555 1_555 1_555 yes P(1) P(2) C(22) C(27) 111.7(3) 1_555 1_555 1_555 1_555 yes P(1) C(1) C(2) C(3) 161.4(3) 1_555 1_555 1_555 1_555 yes P(1) C(1) C(2) C(7) -20.9(7) 1_555 1_555 1_555 1_555 yes P(1) C(1) C(6) C(5) -160.7(4) 1_555 1_555 1_555 1_555 yes P(1) C(1) C(6) C(19) 18.5(6) 1_555 1_555 1_555 1_555 yes P(2) P(1) C(1) C(2) -68.0(4) 1_555 1_555 1_555 1_555 yes P(2) P(1) C(1) C(6) 106.0(3) 1_555 1_555 1_555 1_555 yes P(2) C(22) C(23) C(24) 151.9(3) 1_555 1_555 1_555 1_555 yes P(2) C(22) C(23) C(28) -34.1(6) 1_555 1_555 1_555 1_555 yes P(2) C(22) C(27) C(26) -152.1(4) 1_555 1_555 1_555 1_555 yes P(2) C(22) C(27) C(36) 30.9(6) 1_555 1_555 1_555 1_555 yes C(1) P(1) P(2) C(22) -167.7(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 2.6(7) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(8) 95.9(5) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(9) -147.1(5) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(10) -28.3(7) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) -4.9(7) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(18) 48.2(6) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(20) -75.3(6) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(21) 166.6(5) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) 13.5(7) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(19) -167.3(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 6.0(8) 1_555 1_555 1_555 1_555 yes C(2) C(7) C(10) C(11) -60.0(6) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) -12.5(7) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(8) -86.4(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(9) 30.7(6) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(10) 149.5(4) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) -4.8(8) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(7) -175.4(5) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(19) 175.8(5) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(18) -132.6(5) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(20) 103.9(6) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(21) -14.2(7) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(2) C(7) 165.3(5) 1_555 1_555 1_555 1_555 yes C(6) C(19) C(18) C(17) 64.3(6) 1_555 1_555 1_555 1_555 yes C(7) C(10) C(11) C(12) 173.4(4) 1_555 1_555 1_555 1_555 yes C(8) C(7) C(10) C(11) 175.4(4) 1_555 1_555 1_555 1_555 yes C(9) C(7) C(10) C(11) 61.3(6) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(13) 178.3(4) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(14) 56.9(7) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) 60.9(6) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(16) -169.5(5) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 78.4(6) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) 80.2(6) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) 179.9(5) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(20) -170.8(5) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(21) -56.9(6) 1_555 1_555 1_555 1_555 yes C(22) C(23) C(24) C(25) 3.9(7) 1_555 1_555 1_555 1_555 yes C(22) C(23) C(28) C(29) -7.9(7) 1_555 1_555 1_555 1_555 yes C(22) C(23) C(28) C(30) 116.9(5) 1_555 1_555 1_555 1_555 yes C(22) C(23) C(28) C(31) -124.4(4) 1_555 1_555 1_555 1_555 yes C(22) C(27) C(26) C(25) -5.2(7) 1_555 1_555 1_555 1_555 yes C(22) C(27) C(36) C(37) -78.9(7) 1_555 1_555 1_555 1_555 yes C(22) C(27) C(36) C(38) 45.4(7) 1_555 1_555 1_555 1_555 yes C(22) C(27) C(36) C(39) 162.4(5) 1_555 1_555 1_555 1_555 yes C(23) C(22) C(27) C(26) 17.4(6) 1_555 1_555 1_555 1_555 yes C(23) C(22) C(27) C(36) -159.6(5) 1_555 1_555 1_555 1_555 yes C(23) C(24) C(25) C(26) 8.2(7) 1_555 1_555 1_555 1_555 yes C(23) C(24) C(25) C(32) -176.3(4) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(22) C(27) -16.7(6) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(28) C(29) 166.1(4) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(28) C(30) -69.0(5) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(28) C(31) 49.7(5) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(26) C(27) -7.5(7) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(32) C(33) 129.4(5) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(32) C(34) 10.0(7) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(32) C(35) -110.6(5) 1_555 1_555 1_555 1_555 yes C(25) C(24) C(23) C(28) -170.7(4) 1_555 1_555 1_555 1_555 yes C(25) C(26) C(27) C(36) 172.0(5) 1_555 1_555 1_555 1_555 yes C(26) C(25) C(32) C(33) -55.2(6) 1_555 1_555 1_555 1_555 yes C(26) C(25) C(32) C(34) -174.6(5) 1_555 1_555 1_555 1_555 yes C(26) C(25) C(32) C(35) 64.8(6) 1_555 1_555 1_555 1_555 yes C(26) C(27) C(36) C(37) 104.1(6) 1_555 1_555 1_555 1_555 yes C(26) C(27) C(36) C(38) -131.7(5) 1_555 1_555 1_555 1_555 yes C(26) C(27) C(36) C(39) -14.6(7) 1_555 1_555 1_555 1_555 yes C(27) C(22) C(23) C(28) 157.3(4) 1_555 1_555 1_555 1_555 yes C(27) C(26) C(25) C(32) 176.8(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_17-bromo _database_code_CSD 193389 # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. ; #------------------------------------------------------------------------------ _audit_creation_date 'Wed Sep 11 23:25:29 2002' _audit_creation_method 'by teXsan' _audit_update_record ? _chemical_name_systematic ; 17-bromo-1,1,11,11-tetramethyl-[11]-metacyclophane ; #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C21 H33 Br ' _chemical_formula_moiety 'C21 H33 Br ' _chemical_formula_weight 365.40 _chemical_melting_point 106-107 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 11.387(2) _cell_length_b 10.989(3) _cell_length_c 15.757(5) _cell_angle_alpha 90 _cell_angle_beta 103.25(3) _cell_angle_gamma 90 _cell_volume 1919.2(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 170.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.145 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K€a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method €w _diffrn_detector_area_resol_mean 0.010000 _diffrn_reflns_number 3156 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.4730 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.4730 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1036 _reflns_number_gt 2939 _reflns_threshold_expression F^2^>2.0€s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1704 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3091 _refine_ls_number_parameters 199 _refine_ls_goodness_of_fit_ref 1.935 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[€s^2^(Fo^2^) + (0.06000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 0.77 _refine_diff_density_min -1.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'Br' 'Br' -0.290 2.459 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br(1) Br 0.41448(4) 0.35110(4) 0.98543(3) 0.0377(2) Uani 1.00 d . . . C(1) C 0.2554(4) 0.3023(4) 0.9225(3) 0.0265(10) Uani 1.00 d . . . C(2) C 0.1983(4) 0.2078(3) 0.9586(3) 0.0242(10) Uani 1.00 d . . . C(3) C 0.0847(4) 0.1725(4) 0.9092(3) 0.028(1) Uani 1.00 d . . . C(4) C 0.0328(4) 0.2249(4) 0.8306(3) 0.030(1) Uani 1.00 d . . . C(5) C 0.0921(4) 0.3185(4) 0.7985(3) 0.031(1) Uani 1.00 d . . . C(6) C 0.2052(4) 0.3616(3) 0.8426(3) 0.028(1) Uani 1.00 d . . . C(7) C 0.2492(4) 0.1419(3) 1.0467(3) 0.030(1) Uani 1.00 d . . . C(8) C 0.3662(5) 0.0714(4) 1.0459(3) 0.040(1) Uani 1.00 d . . . C(9) C 0.1598(5) 0.0429(4) 1.0635(3) 0.038(1) Uani 1.00 d . . . C(10) C 0.2690(4) 0.2311(4) 1.1251(3) 0.030(1) Uani 1.00 d . . . C(11) C 0.1564(4) 0.2967(4) 1.1379(3) 0.037(1) Uani 1.00 d . . . C(12) C 0.1847(4) 0.4066(5) 1.1997(3) 0.041(1) Uani 1.00 d . . . C(13) C 0.2506(5) 0.5104(5) 1.1669(3) 0.044(1) Uani 1.00 d . . . C(14) C 0.1855(4) 0.5621(4) 1.0790(3) 0.040(1) Uani 1.00 d . . . C(15) C 0.2516(5) 0.6699(4) 1.0503(4) 0.043(1) Uani 1.00 d . . . C(16) C 0.1897(5) 0.7211(4) 0.9597(4) 0.045(1) Uani 1.00 d . . . C(17) C 0.1653(5) 0.6305(4) 0.8856(4) 0.039(1) Uani 1.00 d . . . C(18) C 0.2804(4) 0.5814(4) 0.8623(3) 0.036(1) Uani 1.00 d . . . C(19) C 0.2622(4) 0.4687(4) 0.8019(3) 0.031(1) Uani 1.00 d . . . C(20) C 0.3837(5) 0.4289(5) 0.7800(3) 0.045(1) Uani 1.00 d . . . C(21) C 0.1820(5) 0.5075(5) 0.7134(3) 0.045(1) Uani 1.00 d . . . H(1) H 0.0423 0.1101 0.9311 0.0344 Uiso 1.00 calc . . . H(2) H -0.0433 0.1966 0.7985 0.0367 Uiso 1.00 calc . . . H(3) H 0.0537 0.3557 0.7447 0.0373 Uiso 1.00 calc . . . H(4) H 0.4300 0.1275 1.0464 0.0477 Uiso 1.00 calc . . . H(5) H 0.3544 0.0228 0.9947 0.0477 Uiso 1.00 calc . . . H(6) H 0.3867 0.0206 1.0958 0.0477 Uiso 1.00 calc . . . H(7) H 0.1476 -0.0155 1.0180 0.0461 Uiso 1.00 calc . . . H(8) H 0.1919 0.0043 1.1177 0.0461 Uiso 1.00 calc . . . H(9) H 0.0847 0.0800 1.0650 0.0461 Uiso 1.00 calc . . . H(10) H 0.3252 0.2912 1.1165 0.0362 Uiso 1.00 calc . . . H(11) H 0.3017 0.1864 1.1765 0.0362 Uiso 1.00 calc . . . H(12) H 0.1087 0.2406 1.1617 0.0443 Uiso 1.00 calc . . . H(13) H 0.1114 0.3242 1.0828 0.0443 Uiso 1.00 calc . . . H(14) H 0.2336 0.3791 1.2534 0.0495 Uiso 1.00 calc . . . H(15) H 0.1108 0.4374 1.2090 0.0495 Uiso 1.00 calc . . . H(16) H 0.3271 0.4812 1.1614 0.0526 Uiso 1.00 calc . . . H(17) H 0.2613 0.5740 1.2085 0.0526 Uiso 1.00 calc . . . H(18) H 0.1076 0.5888 1.0830 0.0493 Uiso 1.00 calc . . . H(19) H 0.1780 0.5002 1.0361 0.0493 Uiso 1.00 calc . . . H(20) H 0.3306 0.6437 1.0484 0.0513 Uiso 1.00 calc . . . H(21) H 0.2567 0.7326 1.0922 0.0513 Uiso 1.00 calc . . . H(22) H 0.2400 0.7832 0.9457 0.0542 Uiso 1.00 calc . . . H(23) H 0.1146 0.7552 0.9640 0.0542 Uiso 1.00 calc . . . H(24) H 0.1176 0.6689 0.8356 0.0468 Uiso 1.00 calc . . . H(25) H 0.1222 0.5636 0.9019 0.0468 Uiso 1.00 calc . . . H(26) H 0.3363 0.5599 0.9152 0.0432 Uiso 1.00 calc . . . H(27) H 0.3143 0.6445 0.8343 0.0432 Uiso 1.00 calc . . . H(28) H 0.4103 0.4899 0.7466 0.0542 Uiso 1.00 calc . . . H(29) H 0.3717 0.3547 0.7479 0.0542 Uiso 1.00 calc . . . H(30) H 0.4428 0.4163 0.8328 0.0542 Uiso 1.00 calc . . . H(31) H 0.2176 0.5755 0.6912 0.0534 Uiso 1.00 calc . . . H(32) H 0.1745 0.4421 0.6731 0.0534 Uiso 1.00 calc . . . H(33) H 0.1042 0.5299 0.7207 0.0534 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0231(3) 0.0477(3) 0.0393(3) -0.0109(2) 0.0009(2) 0.0020(2) C(1) 0.024(2) 0.026(2) 0.029(2) -0.003(2) 0.005(2) -0.004(2) C(2) 0.026(2) 0.020(2) 0.026(2) 0.003(2) 0.005(2) 0.001(2) C(3) 0.023(2) 0.029(2) 0.032(2) -0.005(2) 0.002(2) -0.002(2) C(4) 0.025(2) 0.028(2) 0.035(2) -0.005(2) 0.000(2) 0.000(2) C(5) 0.030(2) 0.033(2) 0.027(2) -0.003(2) 0.002(2) 0.008(2) C(6) 0.029(2) 0.026(2) 0.029(2) -0.001(2) 0.006(2) -0.003(2) C(7) 0.026(2) 0.027(2) 0.034(2) -0.001(2) 0.002(2) 0.005(2) C(8) 0.040(3) 0.036(2) 0.040(2) 0.012(2) 0.003(2) -0.005(2) C(9) 0.045(3) 0.031(2) 0.034(2) -0.009(2) 0.001(2) 0.007(2) C(10) 0.033(2) 0.032(2) 0.023(2) -0.008(2) 0.002(2) 0.000(2) C(11) 0.034(2) 0.041(2) 0.035(2) -0.005(2) 0.008(2) -0.008(2) C(12) 0.040(3) 0.046(3) 0.036(2) -0.006(2) 0.009(2) -0.013(2) C(13) 0.041(3) 0.047(3) 0.041(3) -0.008(2) 0.007(2) -0.019(2) C(14) 0.034(2) 0.044(3) 0.045(3) -0.001(2) 0.010(2) -0.011(2) C(15) 0.042(3) 0.036(2) 0.053(3) -0.007(2) 0.015(2) -0.014(2) C(16) 0.048(3) 0.027(2) 0.060(3) -0.002(2) 0.014(3) -0.008(2) C(17) 0.036(3) 0.028(2) 0.050(3) 0.000(2) 0.004(2) 0.001(2) C(18) 0.039(3) 0.029(2) 0.043(2) -0.012(2) 0.014(2) 0.004(2) C(19) 0.035(2) 0.029(2) 0.029(2) -0.006(2) 0.007(2) 0.003(2) C(20) 0.046(3) 0.049(3) 0.046(3) -0.004(2) 0.021(2) 0.010(2) C(21) 0.051(3) 0.044(3) 0.038(2) -0.011(2) 0.008(2) 0.013(2) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS' _computing_cell_refinement 'PROCESS' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) C(1) 1.931(4) . . yes C(1) C(2) 1.411(6) . . yes C(1) C(6) 1.417(6) . . yes C(2) C(3) 1.403(6) . . yes C(2) C(7) 1.556(6) . . yes C(3) C(4) 1.371(6) . . yes C(4) C(5) 1.389(6) . . yes C(5) C(6) 1.399(6) . . yes C(6) C(19) 1.551(5) . . yes C(7) C(8) 1.543(6) . . yes C(7) C(9) 1.553(6) . . yes C(7) C(10) 1.553(6) . . yes C(10) C(11) 1.524(6) . . yes C(11) C(12) 1.538(6) . . yes C(12) C(13) 1.519(7) . . yes C(13) C(14) 1.523(7) . . yes C(14) C(15) 1.527(7) . . yes C(15) C(16) 1.546(8) . . yes C(16) C(17) 1.510(7) . . yes C(17) C(18) 1.538(7) . . yes C(18) C(19) 1.547(6) . . yes C(19) C(20) 1.562(6) . . yes C(19) C(21) 1.542(6) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br(1) C(1) C(2) 117.5(3) . 1_555 1_555 yes Br(1) C(1) C(6) 117.9(3) . 1_555 1_555 yes C(2) C(1) C(6) 124.6(4) . 1_555 1_555 yes C(1) C(2) C(3) 115.6(4) . 1_555 1_555 yes C(1) C(2) C(7) 126.2(4) . 1_555 1_555 yes C(3) C(2) C(7) 118.2(3) . 1_555 1_555 yes C(2) C(3) C(4) 122.5(4) . 1_555 1_555 yes C(3) C(4) C(5) 119.7(4) . 1_555 1_555 yes C(4) C(5) C(6) 122.6(4) . 1_555 1_555 yes C(1) C(6) C(5) 115.0(4) . 1_555 1_555 yes C(1) C(6) C(19) 126.4(4) . 1_555 1_555 yes C(5) C(6) C(19) 118.5(4) . 1_555 1_555 yes C(2) C(7) C(8) 111.8(4) . 1_555 1_555 yes C(2) C(7) C(9) 110.7(4) . 1_555 1_555 yes C(2) C(7) C(10) 111.9(3) . 1_555 1_555 yes C(8) C(7) C(9) 104.5(3) . 1_555 1_555 yes C(8) C(7) C(10) 110.8(4) . 1_555 1_555 yes C(9) C(7) C(10) 106.7(3) . 1_555 1_555 yes C(7) C(10) C(11) 115.5(4) . 1_555 1_555 yes C(10) C(11) C(12) 113.3(4) . 1_555 1_555 yes C(11) C(12) C(13) 114.9(4) . 1_555 1_555 yes C(12) C(13) C(14) 114.5(4) . 1_555 1_555 yes C(13) C(14) C(15) 112.8(4) . 1_555 1_555 yes C(14) C(15) C(16) 113.8(4) . 1_555 1_555 yes C(15) C(16) C(17) 116.0(4) . 1_555 1_555 yes C(16) C(17) C(18) 113.6(4) . 1_555 1_555 yes C(17) C(18) C(19) 115.2(4) . 1_555 1_555 yes C(6) C(19) C(18) 111.3(3) . 1_555 1_555 yes C(6) C(19) C(20) 110.8(3) . 1_555 1_555 yes C(6) C(19) C(21) 111.5(4) . 1_555 1_555 yes C(18) C(19) C(20) 111.1(4) . 1_555 1_555 yes C(18) C(19) C(21) 107.6(4) . 1_555 1_555 yes C(20) C(19) C(21) 104.4(4) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 Br(1) C(1) C(2) C(3) -177.9(3) 1_555 1_555 1_555 1_555 yes Br(1) C(1) C(2) C(7) 2.5(5) 1_555 1_555 1_555 1_555 yes Br(1) C(1) C(6) C(5) 177.4(3) 1_555 1_555 1_555 1_555 yes Br(1) C(1) C(6) C(19) -3.8(6) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.7(6) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(8) -63.7(5) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(9) -179.8(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(10) 61.3(5) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) 0.3(6) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(18) -61.0(6) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(20) 63.1(5) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(19) C(21) 178.9(4) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) -1.2(6) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(19) 177.7(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) -1.5(7) 1_555 1_555 1_555 1_555 yes C(2) C(7) C(10) C(11) 60.2(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) 0.7(6) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(8) 116.8(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(9) 0.7(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(10) -118.2(4) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 1.0(7) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(7) -179.7(4) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(19) -178.6(4) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(18) 117.8(4) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(20) -118.1(5) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(19) C(21) -2.4(6) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(2) C(7) -178.9(4) 1_555 1_555 1_555 1_555 yes C(6) C(19) C(18) C(17) -57.9(5) 1_555 1_555 1_555 1_555 yes C(7) C(10) C(11) C(12) -164.9(4) 1_555 1_555 1_555 1_555 yes C(8) C(7) C(10) C(11) -174.2(4) 1_555 1_555 1_555 1_555 yes C(9) C(7) C(10) C(11) -61.0(4) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(13) 65.0(6) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(14) 57.3(6) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) 177.3(4) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(16) 177.9(4) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) -54.7(6) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) -67.5(6) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) 166.9(4) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(20) 178.1(4) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(21) 64.5(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag #------------------------------------------------------------------------------