#------------------------------------------------------------------------------ #$Date: 2022-02-04 21:59:05 +0200 (Fri, 04 Feb 2022) $ #$Revision: 272750 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158429.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158429 loop_ _publ_author_name 'Baire, Beeraiah' 'Santhi, Jampani' _publ_section_title ; Ag(I)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes via a [4 + 2] cycloaddition of benzopyrylium ions: access to structurally unique naphthalenes. ; _journal_issue 1 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 247 _journal_page_last 251 _journal_paper_doi 10.1039/d1ob02229f _journal_volume 20 _journal_year 2021 _chemical_formula_sum 'C33 H18 Br2 O' _chemical_formula_weight 590.29 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-11-13 deposited with the CCDC. 2021-12-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 122.657(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.5539(7) _cell_length_b 17.8625(8) _cell_length_c 12.4649(9) _cell_measurement_temperature 296(2) _cell_volume 2540.8(3) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0775 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7587 _diffrn_reflns_point_group_measured_fraction_full 0.824 _diffrn_reflns_point_group_measured_fraction_max 0.823 _diffrn_reflns_theta_full 24.828 _diffrn_reflns_theta_max 24.828 _diffrn_reflns_theta_min 2.118 _exptl_absorpt_coefficient_mu 3.215 _exptl_crystal_density_diffrn 1.543 _exptl_crystal_F_000 1176 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.322 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details ; Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.010(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 325 _refine_ls_number_reflns 3604 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.954 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0352 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0177P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.0835 _reflns_Friedel_coverage 0.646 _reflns_Friedel_fraction_full 0.648 _reflns_Friedel_fraction_max 0.648 _reflns_number_gt 2513 _reflns_number_total 3604 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob02229f2.cif _cod_data_source_block 17 _cod_depositor_comments 'Adding full bibliography for 7158428--7158430.cif.' _cod_original_sg_symbol_H-M 'C c' _cod_database_code 7158429 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.500 _shelx_estimated_absorpt_t_max 0.739 _shelx_res_file ; 17.res created by SHELXL-2014/7 TITL 17 in Cc CELL 0.71073 13.55390 17.86250 12.46495 90.0000 122.6566 90.0000 ZERR 4 0.00070 0.00080 0.00086 0.0000 0.0021 0.0000 LATT -7 SYMM X, -Y, 0.5+Z SFAC C H Br O UNIT 132 72 8 4 OMIT -3 50 L.S. 8 ACTA BOND $H FMAP 2 PLAN 5 CONF SIZE 0.100 0.220 0.250 TEMP 23.000 WGHT 0.017700 FVAR 0.07974 MOLE 1 BR1 3 -0.408558 -0.049118 0.034585 11.00000 0.06321 0.09998 = 0.04679 -0.00787 0.00258 -0.01067 BR2 3 -0.251899 0.168826 0.139748 11.00000 0.10668 0.10373 = 0.03422 -0.00128 0.00569 0.01611 C1 1 0.196661 0.179761 1.062403 11.00000 0.04490 0.02980 = 0.03649 -0.00212 0.02144 -0.00156 C2 1 0.087540 0.209338 1.034643 11.00000 0.05683 0.03931 = 0.04588 0.00043 0.02487 0.00362 AFIX 43 H2 2 0.024553 0.212688 0.950584 11.00000 -1.20000 AFIX 0 C3 1 0.075424 0.232462 1.129917 11.00000 0.08147 0.06643 = 0.06516 -0.00581 0.04849 0.01222 AFIX 43 H3 2 0.003959 0.251869 1.110632 11.00000 -1.20000 AFIX 0 C4 1 0.168623 0.227755 1.257441 11.00000 0.09610 0.07747 = 0.05722 -0.01736 0.04786 0.00490 AFIX 43 H4 2 0.158556 0.243274 1.322154 11.00000 -1.20000 AFIX 0 C5 1 0.273329 0.200552 1.286119 11.00000 0.07594 0.06158 = 0.03643 -0.00897 0.02745 -0.00429 AFIX 43 H5 2 0.334971 0.198224 1.370979 11.00000 -1.20000 AFIX 0 C6 1 0.291140 0.176013 1.192106 11.00000 0.05172 0.03636 = 0.03606 -0.00622 0.02107 -0.00836 C7 1 0.400409 0.149459 1.219365 11.00000 0.04801 0.03989 = 0.02964 -0.00202 0.00637 -0.00916 AFIX 43 H7 2 0.464042 0.149309 1.303316 11.00000 -1.20000 AFIX 0 C8 1 0.415048 0.123983 1.125573 11.00000 0.04250 0.05053 = 0.03249 0.00009 0.01394 0.00094 AFIX 43 H8 2 0.487618 0.105350 1.147182 11.00000 -1.20000 AFIX 0 C9 1 0.322458 0.125407 0.996999 11.00000 0.02960 0.02851 = 0.03084 -0.00383 0.01291 -0.00238 C10 1 0.215277 0.154287 0.964593 11.00000 0.04172 0.02706 = 0.02995 -0.00573 0.01478 -0.00581 C11 1 0.345228 0.103711 0.896575 11.00000 0.03051 0.03906 = 0.02811 -0.00110 0.00807 0.00741 C12 1 0.428218 0.145111 0.886742 11.00000 0.04070 0.03697 = 0.04938 -0.00465 0.02285 -0.00435 AFIX 43 H12 2 0.471490 0.182165 0.946449 11.00000 -1.20000 AFIX 0 C13 1 0.446002 0.131736 0.791392 11.00000 0.04404 0.06155 = 0.06260 -0.00184 0.03151 -0.01484 AFIX 43 H13 2 0.501833 0.159658 0.787365 11.00000 -1.20000 AFIX 0 C14 1 0.383317 0.077718 0.700161 11.00000 0.04163 0.06972 = 0.05819 0.00944 0.03527 0.00593 AFIX 43 H14 2 0.396167 0.069220 0.635039 11.00000 -1.20000 AFIX 0 C15 1 0.300711 0.036388 0.707803 11.00000 0.04014 0.04633 = 0.03193 -0.00814 0.01588 0.00963 AFIX 43 H15 2 0.256562 0.000618 0.645766 11.00000 -1.20000 AFIX 0 C16 1 0.282688 0.047235 0.805474 11.00000 0.03201 0.03241 = 0.03078 0.00581 0.01478 0.00346 C17 1 0.193725 -0.000596 0.810924 11.00000 0.04391 0.02782 = 0.03974 -0.00091 0.01982 0.00897 C18 1 0.092782 -0.021955 0.687431 11.00000 0.03969 0.03901 = 0.04014 -0.00036 0.01731 -0.00940 C19 1 0.008371 -0.031480 0.583934 11.00000 0.04419 0.04637 = 0.04183 0.00003 0.02258 -0.00095 C20 1 -0.090441 -0.039611 0.454185 11.00000 0.03748 0.04613 = 0.03567 -0.00438 0.01874 -0.00313 C21 1 -0.072921 -0.040531 0.356419 11.00000 0.04077 0.06674 = 0.04005 0.00068 0.01956 0.00324 AFIX 43 H21 2 0.002959 -0.037901 0.373983 11.00000 -1.20000 AFIX 0 C22 1 -0.166929 -0.045349 0.230765 11.00000 0.05775 0.06345 = 0.03666 -0.00222 0.02481 0.00616 AFIX 43 H22 2 -0.153903 -0.047875 0.164847 11.00000 -1.20000 AFIX 0 C23 1 -0.279476 -0.046358 0.204459 11.00000 0.05000 0.04718 = 0.04083 -0.01176 0.01577 -0.00845 C24 1 -0.297854 -0.045095 0.301021 11.00000 0.03658 0.10036 = 0.05568 -0.01912 0.02006 -0.01746 AFIX 43 H24 2 -0.373835 -0.046068 0.283388 11.00000 -1.20000 AFIX 0 C25 1 -0.203919 -0.042369 0.425245 11.00000 0.06396 0.08419 = 0.04771 -0.01104 0.03540 -0.02419 AFIX 43 H25 2 -0.217277 -0.042388 0.491008 11.00000 -1.20000 AFIX 0 C26 1 0.123648 0.161383 0.833121 11.00000 0.03912 0.03138 = 0.03611 -0.00380 0.01990 0.00477 C27 1 0.056728 0.164800 0.720773 11.00000 0.03741 0.03969 = 0.03691 -0.00215 0.01694 0.01011 C28 1 -0.016970 0.166167 0.582678 11.00000 0.03647 0.02972 = 0.03195 0.00243 0.01037 0.00613 C29 1 0.031185 0.153306 0.511029 11.00000 0.03913 0.05354 = 0.03688 0.00664 0.01479 0.00655 AFIX 43 H29 2 0.111291 0.144759 0.551830 11.00000 -1.20000 AFIX 0 C30 1 -0.038234 0.152969 0.379222 11.00000 0.06215 0.05627 = 0.04327 0.00303 0.02955 0.00900 AFIX 43 H30 2 -0.005635 0.144128 0.331153 11.00000 -1.20000 AFIX 0 C31 1 -0.156865 0.166031 0.320623 11.00000 0.07277 0.04051 = 0.02324 -0.00063 0.00679 0.00445 C32 1 -0.206613 0.178691 0.389137 11.00000 0.03758 0.04920 = 0.04376 -0.00574 0.00571 0.01346 AFIX 43 H32 2 -0.286613 0.187891 0.347580 11.00000 -1.20000 AFIX 0 C33 1 -0.137693 0.177786 0.520409 11.00000 0.04761 0.04165 = 0.04386 -0.00063 0.01966 0.00669 AFIX 43 H33 2 -0.171603 0.184920 0.567581 11.00000 -1.20000 AFIX 0 O1 4 0.204581 -0.020113 0.910208 11.00000 0.05818 0.05355 = 0.03864 -0.00002 0.02176 -0.01001 HKLF 4 REM 17 in Cc REM R1 = 0.0352 for 2513 Fo > 4sig(Fo) and 0.0635 for all 3604 data REM 325 parameters refined using 2 restraints END WGHT 0.0177 0.0000 REM Highest difference peak 0.322, deepest hole -0.359, 1-sigma level 0.052 Q1 1 -0.2086 0.1683 0.2391 11.00000 0.05 0.32 Q2 1 -0.4352 -0.0550 -0.0649 11.00000 0.05 0.31 Q3 1 -0.3752 -0.0498 0.1216 11.00000 0.05 0.29 Q4 1 -0.3678 -0.0828 0.0331 11.00000 0.05 0.24 Q5 1 -0.1931 0.1583 0.1542 11.00000 0.05 0.22 ; _shelx_res_checksum 85209 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.40856(8) -0.04912(6) 0.03458(7) 0.0837(4) Uani 1 1 d . . . . . Br2 Br -0.25190(9) 0.16883(6) 0.13975(8) 0.0979(4) Uani 1 1 d . . . . . C1 C 0.1967(6) 0.1798(4) 1.0624(6) 0.0373(17) Uani 1 1 d . . . . . C2 C 0.0875(8) 0.2093(4) 1.0346(8) 0.0488(19) Uani 1 1 d . . . . . H2 H 0.0246 0.2127 0.9506 0.059 Uiso 1 1 calc R U . . . C3 C 0.0754(8) 0.2325(4) 1.1299(8) 0.066(2) Uani 1 1 d . . . . . H3 H 0.0040 0.2519 1.1106 0.080 Uiso 1 1 calc R U . . . C4 C 0.1686(9) 0.2278(5) 1.2574(8) 0.074(3) Uani 1 1 d . . . . . H4 H 0.1586 0.2433 1.3222 0.088 Uiso 1 1 calc R U . . . C5 C 0.2733(8) 0.2006(4) 1.2861(7) 0.059(2) Uani 1 1 d . . . . . H5 H 0.3350 0.1982 1.3710 0.071 Uiso 1 1 calc R U . . . C6 C 0.2911(6) 0.1760(4) 1.1921(6) 0.0427(19) Uani 1 1 d . . . . . C7 C 0.4004(6) 0.1495(4) 1.2194(6) 0.047(2) Uani 1 1 d . . . . . H7 H 0.4640 0.1493 1.3033 0.056 Uiso 1 1 calc R U . . . C8 C 0.4150(6) 0.1240(4) 1.1256(6) 0.0450(19) Uani 1 1 d . . . . . H8 H 0.4876 0.1054 1.1472 0.054 Uiso 1 1 calc R U . . . C9 C 0.3225(5) 0.1254(3) 0.9970(5) 0.0314(16) Uani 1 1 d . . . . . C10 C 0.2153(6) 0.1543(3) 0.9646(6) 0.0352(17) Uani 1 1 d . . . . . C11 C 0.3452(5) 0.1037(4) 0.8966(5) 0.0365(17) Uani 1 1 d . . . . . C12 C 0.4282(6) 0.1451(4) 0.8867(7) 0.043(2) Uani 1 1 d . . . . . H12 H 0.4715 0.1822 0.9464 0.052 Uiso 1 1 calc R U . . . C13 C 0.4460(7) 0.1317(5) 0.7914(8) 0.055(2) Uani 1 1 d . . . . . H13 H 0.5018 0.1597 0.7874 0.066 Uiso 1 1 calc R U . . . C14 C 0.3833(6) 0.0777(4) 0.7002(7) 0.052(2) Uani 1 1 d . . . . . H14 H 0.3962 0.0692 0.6350 0.063 Uiso 1 1 calc R U . . . C15 C 0.3007(6) 0.0364(4) 0.7078(6) 0.0413(19) Uani 1 1 d . . . . . H15 H 0.2566 0.0006 0.6458 0.050 Uiso 1 1 calc R U . . . C16 C 0.2827(5) 0.0472(3) 0.8055(6) 0.0328(16) Uani 1 1 d . . . . . C17 C 0.1937(6) -0.0006(4) 0.8109(6) 0.0386(18) Uani 1 1 d . . . . . C18 C 0.0928(6) -0.0220(4) 0.6874(6) 0.0418(18) Uani 1 1 d . . . . . C19 C 0.0084(6) -0.0315(4) 0.5839(6) 0.0445(19) Uani 1 1 d . . . . . C20 C -0.0904(6) -0.0396(4) 0.4542(6) 0.0403(18) Uani 1 1 d . . . . . C21 C -0.0729(6) -0.0405(4) 0.3564(7) 0.050(2) Uani 1 1 d . . . . . H21 H 0.0030 -0.0379 0.3740 0.060 Uiso 1 1 calc R U . . . C22 C -0.1669(7) -0.0453(4) 0.2308(6) 0.053(2) Uani 1 1 d . . . . . H22 H -0.1539 -0.0479 0.1648 0.064 Uiso 1 1 calc R U . . . C23 C -0.2795(6) -0.0464(4) 0.2045(7) 0.050(2) Uani 1 1 d . . . . . C24 C -0.2979(7) -0.0451(5) 0.3010(8) 0.067(3) Uani 1 1 d . . . . . H24 H -0.3738 -0.0461 0.2834 0.080 Uiso 1 1 calc R U . . . C25 C -0.2039(7) -0.0424(5) 0.4252(7) 0.063(2) Uani 1 1 d . . . . . H25 H -0.2173 -0.0424 0.4910 0.075 Uiso 1 1 calc R U . . . C26 C 0.1236(6) 0.1614(3) 0.8331(6) 0.0357(17) Uani 1 1 d . . . . . C27 C 0.0567(6) 0.1648(4) 0.7208(6) 0.0396(18) Uani 1 1 d . . . . . C28 C -0.0170(6) 0.1662(3) 0.5827(6) 0.0368(17) Uani 1 1 d . . . . . C29 C 0.0312(6) 0.1533(4) 0.5110(7) 0.046(2) Uani 1 1 d . . . . . H29 H 0.1113 0.1448 0.5518 0.055 Uiso 1 1 calc R U . . . C30 C -0.0382(7) 0.1530(4) 0.3792(7) 0.053(2) Uani 1 1 d . . . . . H30 H -0.0056 0.1441 0.3312 0.064 Uiso 1 1 calc R U . . . C31 C -0.1569(7) 0.1660(4) 0.3206(6) 0.055(2) Uani 1 1 d . . . . . C32 C -0.2066(6) 0.1787(4) 0.3891(7) 0.052(2) Uani 1 1 d . . . . . H32 H -0.2866 0.1879 0.3476 0.062 Uiso 1 1 calc R U . . . C33 C -0.1377(6) 0.1778(4) 0.5204(6) 0.047(2) Uani 1 1 d . . . . . H33 H -0.1716 0.1849 0.5676 0.056 Uiso 1 1 calc R U . . . O1 O 0.2046(4) -0.0201(3) 0.9102(5) 0.0523(14) 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 0.0632(5) 0.1000(7) 0.0468(5) -0.0079(5) 0.0026(4) -0.0107(6) Br2 0.1067(8) 0.1037(8) 0.0342(5) -0.0013(5) 0.0057(5) 0.0161(7) C1 0.045(4) 0.030(4) 0.036(4) -0.002(3) 0.021(3) -0.002(3) C2 0.057(5) 0.039(4) 0.046(4) 0.000(4) 0.025(4) 0.004(5) C3 0.081(6) 0.066(6) 0.065(6) -0.006(4) 0.048(5) 0.012(5) C4 0.096(7) 0.077(7) 0.057(6) -0.017(5) 0.048(5) 0.005(6) C5 0.076(6) 0.062(5) 0.036(4) -0.009(4) 0.027(4) -0.004(5) C6 0.052(5) 0.036(4) 0.036(4) -0.006(3) 0.021(4) -0.008(4) C7 0.048(5) 0.040(4) 0.030(4) -0.002(3) 0.006(3) -0.009(4) C8 0.042(4) 0.051(5) 0.032(4) 0.000(3) 0.014(3) 0.001(3) C9 0.030(4) 0.029(4) 0.031(3) -0.004(3) 0.013(3) -0.002(3) C10 0.042(4) 0.027(4) 0.030(3) -0.006(3) 0.015(3) -0.006(3) C11 0.031(4) 0.039(4) 0.028(3) -0.001(3) 0.008(3) 0.007(3) C12 0.041(4) 0.037(5) 0.049(5) -0.005(4) 0.023(4) -0.004(4) C13 0.044(5) 0.062(6) 0.063(6) -0.002(4) 0.032(4) -0.015(4) C14 0.042(4) 0.070(6) 0.058(5) 0.009(4) 0.035(4) 0.006(4) C15 0.040(4) 0.046(5) 0.032(4) -0.008(3) 0.016(3) 0.010(4) C16 0.032(4) 0.032(4) 0.031(3) 0.006(3) 0.015(3) 0.003(3) C17 0.044(4) 0.028(4) 0.040(4) -0.001(3) 0.020(4) 0.009(3) C18 0.040(4) 0.039(4) 0.040(4) 0.000(3) 0.017(4) -0.009(3) C19 0.044(4) 0.046(5) 0.042(4) 0.000(3) 0.023(4) -0.001(3) C20 0.037(4) 0.046(5) 0.036(4) -0.004(3) 0.019(3) -0.003(4) C21 0.041(4) 0.067(6) 0.040(4) 0.001(4) 0.020(4) 0.003(4) C22 0.058(5) 0.063(6) 0.037(4) -0.002(4) 0.025(4) 0.006(4) C23 0.050(5) 0.047(5) 0.041(4) -0.012(3) 0.016(4) -0.008(4) C24 0.037(5) 0.100(7) 0.056(5) -0.019(5) 0.020(4) -0.017(5) C25 0.064(6) 0.084(6) 0.048(5) -0.011(4) 0.035(4) -0.024(5) C26 0.039(4) 0.031(4) 0.036(4) -0.004(3) 0.020(3) 0.005(3) C27 0.037(4) 0.040(4) 0.037(4) -0.002(3) 0.017(3) 0.010(3) C28 0.036(4) 0.030(4) 0.032(4) 0.002(3) 0.010(3) 0.006(3) C29 0.039(4) 0.054(5) 0.037(4) 0.007(3) 0.015(3) 0.007(4) C30 0.062(5) 0.056(5) 0.043(4) 0.003(4) 0.030(4) 0.009(4) C31 0.073(6) 0.041(5) 0.023(4) -0.001(3) 0.007(4) 0.004(4) C32 0.038(4) 0.049(5) 0.044(4) -0.006(4) 0.006(4) 0.013(4) C33 0.048(5) 0.042(5) 0.044(4) -0.001(3) 0.020(4) 0.007(4) O1 0.058(3) 0.054(3) 0.039(3) 0.000(2) 0.022(2) -0.010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C6 C1 C2 118.2(7) . . ? C6 C1 C10 118.9(6) . . ? C2 C1 C10 122.8(6) . . ? C3 C2 C1 120.2(8) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 121.1(9) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.8(8) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.7(7) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C7 122.7(7) . . ? C5 C6 C1 119.0(7) . . ? C7 C6 C1 118.3(6) . . ? C8 C7 C6 121.6(6) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 121.2(7) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 119.5(6) . . ? C10 C9 C11 120.8(5) . . ? C8 C9 C11 119.4(6) . . ? C9 C10 C26 119.6(6) . . ? C9 C10 C1 120.4(6) . . ? C26 C10 C1 120.0(6) . . ? C12 C11 C16 117.9(7) . . ? C12 C11 C9 118.3(6) . . ? C16 C11 C9 123.7(6) . . ? C13 C12 C11 120.9(6) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 121.6(7) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C15 118.5(7) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 121.4(7) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C11 119.7(6) . . ? C15 C16 C17 119.1(6) . . ? C11 C16 C17 121.1(6) . . ? O1 C17 C18 122.0(7) . . ? O1 C17 C16 123.2(6) . . ? C18 C17 C16 114.8(6) . . ? C19 C18 C17 173.0(7) . . ? C18 C19 C20 175.7(8) . . ? C21 C20 C25 118.3(6) . . ? C21 C20 C19 119.9(6) . . ? C25 C20 C19 121.7(7) . . ? C20 C21 C22 120.9(7) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C23 C22 C21 119.6(7) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C24 C23 C22 120.0(7) . . ? C24 C23 Br1 119.6(6) . . ? C22 C23 Br1 120.4(6) . . ? C23 C24 C25 119.9(8) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C20 121.3(7) . . ? C24 C25 H25 119.3 . . ? C20 C25 H25 119.3 . . ? C27 C26 C10 172.5(7) . . ? C26 C27 C28 175.0(7) . . ? C29 C28 C33 119.1(6) . . ? C29 C28 C27 120.1(6) . . ? C33 C28 C27 120.8(7) . . ? C28 C29 C30 120.8(7) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C31 C30 C29 118.6(8) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C32 C31 C30 121.7(7) . . ? C32 C31 Br2 119.4(6) . . ? C30 C31 Br2 118.8(7) . . ? C31 C32 C33 119.6(7) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C32 C33 C28 120.1(7) . . ? C32 C33 H33 120.0 . . ? C28 C33 H33 120.0 . . ? 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 C23 1.884(7) . ? Br2 C31 1.900(6) . ? C1 C6 1.423(8) . ? C1 C2 1.426(11) . ? C1 C10 1.445(9) . ? C2 C3 1.348(11) . ? C2 H2 0.9300 . ? C3 C4 1.401(11) . ? C3 H3 0.9300 . ? C4 C5 1.353(12) . ? C4 H4 0.9300 . ? C5 C6 1.389(10) . ? C5 H5 0.9300 . ? C6 C7 1.411(10) . ? C7 C8 1.365(9) . ? C7 H7 0.9300 . ? C8 C9 1.405(8) . ? C8 H8 0.9300 . ? C9 C10 1.381(9) . ? C9 C11 1.493(9) . ? C10 C26 1.431(8) . ? C11 C12 1.406(10) . ? C11 C16 1.410(9) . ? C12 C13 1.355(10) . ? C12 H12 0.9300 . ? C13 C14 1.380(10) . ? C13 H13 0.9300 . ? C14 C15 1.387(10) . ? C14 H14 0.9300 . ? C15 C16 1.379(9) . ? C15 H15 0.9300 . ? C16 C17 1.509(10) . ? C17 O1 1.216(7) . ? C17 C18 1.454(9) . ? C18 C19 1.187(8) . ? C19 C20 1.447(9) . ? C20 C21 1.362(9) . ? C20 C25 1.378(10) . ? C21 C22 1.389(9) . ? C21 H21 0.9300 . ? C22 C23 1.377(10) . ? C22 H22 0.9300 . ? C23 C24 1.355(10) . ? C24 C25 1.376(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.190(8) . ? C27 C28 1.451(8) . ? C28 C29 1.380(10) . ? C28 C33 1.397(9) . ? C29 C30 1.384(9) . ? C29 H29 0.9300 . ? C30 C31 1.381(11) . ? C30 H30 0.9300 . ? C31 C32 1.363(10) . ? C32 C33 1.379(9) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? 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 C6 C1 C2 C3 -0.4(10) . . . . ? C10 C1 C2 C3 -179.8(7) . . . . ? C1 C2 C3 C4 -0.3(12) . . . . ? C2 C3 C4 C5 0.9(13) . . . . ? C3 C4 C5 C6 -0.8(13) . . . . ? C4 C5 C6 C7 178.1(8) . . . . ? C4 C5 C6 C1 0.1(12) . . . . ? C2 C1 C6 C5 0.5(10) . . . . ? C10 C1 C6 C5 179.9(6) . . . . ? C2 C1 C6 C7 -177.6(6) . . . . ? C10 C1 C6 C7 1.8(10) . . . . ? C5 C6 C7 C8 178.4(7) . . . . ? C1 C6 C7 C8 -3.5(10) . . . . ? C6 C7 C8 C9 2.1(10) . . . . ? C7 C8 C9 C10 1.1(10) . . . . ? C7 C8 C9 C11 174.3(6) . . . . ? C8 C9 C10 C26 175.0(6) . . . . ? C11 C9 C10 C26 1.9(9) . . . . ? C8 C9 C10 C1 -2.8(9) . . . . ? C11 C9 C10 C1 -175.9(6) . . . . ? C6 C1 C10 C9 1.3(9) . . . . ? C2 C1 C10 C9 -179.3(6) . . . . ? C6 C1 C10 C26 -176.5(6) . . . . ? C2 C1 C10 C26 2.9(10) . . . . ? C10 C9 C11 C12 113.4(7) . . . . ? C8 C9 C11 C12 -59.7(8) . . . . ? C10 C9 C11 C16 -62.2(9) . . . . ? C8 C9 C11 C16 124.7(7) . . . . ? C16 C11 C12 C13 1.0(10) . . . . ? C9 C11 C12 C13 -174.9(6) . . . . ? C11 C12 C13 C14 0.5(11) . . . . ? C12 C13 C14 C15 -0.2(11) . . . . ? C13 C14 C15 C16 -1.5(10) . . . . ? C14 C15 C16 C11 3.0(9) . . . . ? C14 C15 C16 C17 -178.5(6) . . . . ? C12 C11 C16 C15 -2.7(9) . . . . ? C9 C11 C16 C15 173.0(5) . . . . ? C12 C11 C16 C17 178.9(5) . . . . ? C9 C11 C16 C17 -5.5(9) . . . . ? C15 C16 C17 O1 146.6(6) . . . . ? C11 C16 C17 O1 -34.9(9) . . . . ? C15 C16 C17 C18 -33.4(8) . . . . ? C11 C16 C17 C18 145.1(6) . . . . ? C25 C20 C21 C22 -1.0(11) . . . . ? C19 C20 C21 C22 -177.5(6) . . . . ? C20 C21 C22 C23 2.5(11) . . . . ? C21 C22 C23 C24 -2.1(12) . . . . ? C21 C22 C23 Br1 177.6(5) . . . . ? C22 C23 C24 C25 0.4(12) . . . . ? Br1 C23 C24 C25 -179.4(6) . . . . ? C23 C24 C25 C20 1.1(13) . . . . ? C21 C20 C25 C24 -0.8(12) . . . . ? C19 C20 C25 C24 175.6(7) . . . . ? C33 C28 C29 C30 1.0(10) . . . . ? C27 C28 C29 C30 178.7(6) . . . . ? C28 C29 C30 C31 0.2(11) . . . . ? C29 C30 C31 C32 -0.4(11) . . . . ? C29 C30 C31 Br2 178.0(5) . . . . ? C30 C31 C32 C33 -0.7(11) . . . . ? Br2 C31 C32 C33 -179.1(5) . . . . ? C31 C32 C33 C28 1.9(10) . . . . ? C29 C28 C33 C32 -2.1(10) . . . . ? C27 C28 C33 C32 -179.8(6) . . . . ?