data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 #============================================================================== _audit_creation_date 20-11-03 _audit_creation_method from_SDP_and_SHELX97 _audit_update_record ; ? ; _publ_contact_author_name 'Prof Ulli Englert' _publ_contact_author_address ; Institute for Inorganic Chemistry RWTH Aachen Aachen D-52074 GERMANY ; _publ_contact_author_email ullrich.englert@ac.rwth-aachen.de _publ_contact_author_fax '(0241) 8092288' _publ_contact_author_phone '(0241) 8094666' _publ_section_title ; Isosteric molecules in non-isomorphous structures: A new route to new structures. The example of 9,10-dihaloanthracene. ; _publ_section_references ; Bruker (1999). SAINT+. Version 6.02. Bruker AXS Inc., Madison, Wisconson, USA. Bruker (2001). SMART. Version 5.624. Bruker AXS Inc., Madison, Wisconson, USA. Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXS-97. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of Gottingen, Germany. Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconson, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. ; _publ_section_acknowledgements ; Support from the DFG and the Fonds der Chemischen Industrie is gratefully acknowledged. ; loop_ _publ_author_name 'Ulli Englert' 'Roland Haerter' 'Chunhua Hu' 'Qi Li' #===================================================================== data_3b _database_code_depnum_ccdc_archive 'CCDC 216306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dichloroanthracene ; _chemical_name_common dichloroanthracene _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 Cl2' _chemical_formula_weight 247.10 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' Cl Cl 0.3639 0.7018 '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 3.9004(8) _cell_length_b 8.7632(18) _cell_length_c 16.508(3) _cell_angle_alpha 105.33(3) _cell_angle_beta 90.09(3) _cell_angle_gamma 100.97(3) _cell_volume 533.42(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 17 _cell_measurement_theta_max 35 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 5.153 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.09 _exptl_absorpt_correction_T_max 0.90 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 166 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3789 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.0965 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.31 _diffrn_reflns_theta_max 73.92 _reflns_number_total 2140 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+0.0684P] 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 2140 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1713 _refine_ls_wR_factor_gt 0.1557 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3108(2) 0.28774(10) 0.15710(5) 0.0520(3) Uani 1 d . . . C9 C 0.1359(8) 0.1261(4) 0.0689(2) 0.0415(7) Uani 1 d . . . C9A C 0.2296(8) 0.1395(4) -0.01091(19) 0.0407(6) Uani 1 d . . . C1 C 0.4606(9) 0.2761(4) -0.0248(2) 0.0511(8) Uani 1 d . . . H1A H 0.5564 0.3616 0.0209 0.061 Uiso 1 calc R . . C2 C 0.5431(11) 0.2833(5) -0.1038(3) 0.0581(9) Uani 1 d . . . H2A H 0.6939 0.3735 -0.1115 0.070 Uiso 1 calc R . . C3 C 0.4011(10) 0.1543(5) -0.1744(2) 0.0577(9) Uani 1 d . . . H3A H 0.4585 0.1606 -0.2282 0.069 Uiso 1 calc R . . C4 C 0.1847(9) 0.0234(4) -0.1640(2) 0.0497(8) Uani 1 d . . . H4A H 0.0939 -0.0599 -0.2112 0.060 Uiso 1 calc R . . C4A C 0.0892(8) 0.0082(4) -0.08245(19) 0.0415(7) Uani 1 d . . . Cl2 Cl 0.4359(2) 0.83802(9) 0.61821(5) 0.0527(3) Uani 1 d . . . C9B C 0.4709(7) 0.6484(3) 0.55194(19) 0.0378(6) Uani 1 d . . . C9AB C 0.3461(7) 0.5117(4) 0.57900(19) 0.0374(6) Uani 1 d . . . C1B C 0.1866(8) 0.5156(4) 0.65705(19) 0.0453(7) Uani 1 d . . . H1B H 0.1611 0.6144 0.6923 0.054 Uiso 1 calc R . . C2B C 0.0723(10) 0.3807(5) 0.6812(2) 0.0536(8) Uani 1 d . . . H2BA H -0.0263 0.3875 0.7329 0.064 Uiso 1 calc R . . C3B C 0.1013(10) 0.2284(5) 0.6282(2) 0.0536(8) Uani 1 d . . . H3BA H 0.0191 0.1354 0.6450 0.064 Uiso 1 calc R . . C4B C 0.2479(8) 0.2173(4) 0.5533(2) 0.0463(7) Uani 1 d . . . H4BA H 0.2658 0.1162 0.5193 0.056 Uiso 1 calc R . . C4AB C 0.3757(7) 0.3571(3) 0.52528(18) 0.0377(6) Uani 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 Cl1 0.0492(5) 0.0540(5) 0.0444(4) -0.0010(3) 0.0001(3) 0.0099(3) C9 0.0324(14) 0.0462(16) 0.0447(16) 0.0042(12) -0.0007(11) 0.0164(11) C9A 0.0331(14) 0.0462(16) 0.0449(16) 0.0103(12) 0.0045(11) 0.0158(11) C1 0.0416(17) 0.0493(18) 0.063(2) 0.0138(15) 0.0065(15) 0.0132(14) C2 0.050(2) 0.060(2) 0.073(2) 0.0280(19) 0.0158(17) 0.0148(16) C3 0.052(2) 0.078(3) 0.055(2) 0.0313(19) 0.0179(16) 0.0242(18) C4 0.0479(19) 0.062(2) 0.0426(17) 0.0125(14) 0.0074(13) 0.0215(15) C4A 0.0368(15) 0.0504(17) 0.0409(15) 0.0105(13) 0.0035(11) 0.0202(12) Cl2 0.0531(5) 0.0402(4) 0.0580(5) 0.0003(3) 0.0112(4) 0.0108(3) C9B 0.0273(13) 0.0381(14) 0.0442(15) 0.0036(11) -0.0015(11) 0.0077(10) C9AB 0.0252(13) 0.0440(15) 0.0405(14) 0.0065(11) 0.0003(10) 0.0079(10) C1B 0.0349(15) 0.0574(19) 0.0399(16) 0.0066(13) 0.0035(12) 0.0096(13) C2B 0.0428(18) 0.074(2) 0.0467(18) 0.0232(17) 0.0069(14) 0.0088(16) C3B 0.0422(18) 0.057(2) 0.064(2) 0.0272(17) 0.0004(15) 0.0003(14) C4B 0.0367(16) 0.0454(17) 0.0562(19) 0.0147(14) -0.0008(13) 0.0048(12) C4AB 0.0255(13) 0.0425(15) 0.0426(15) 0.0074(12) -0.0005(10) 0.0060(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C9 1.769(3) . ? C9 C4A 1.397(5) 2 ? C9 C9A 1.397(4) . ? C9A C1 1.425(5) . ? C9A C4A 1.435(4) . ? C1 C2 1.357(5) . ? C1 H1A 0.9300 . ? C2 C3 1.416(6) . ? C2 H2A 0.9300 . ? C3 C4 1.339(5) . ? C3 H3A 0.9300 . ? C4 C4A 1.431(5) . ? C4 H4A 0.9300 . ? C4A C9 1.397(5) 2 ? Cl2 C9B 1.761(3) . ? C9B C9AB 1.390(4) . ? C9B C4AB 1.402(4) 2_666 ? C9AB C4AB 1.436(4) . ? C9AB C1B 1.427(4) . ? C1B C2B 1.342(5) . ? C1B H1B 0.9300 . ? C2B C3B 1.414(6) . ? C2B H2BA 0.9300 . ? C3B C4B 1.351(5) . ? C3B H3BA 0.9300 . ? C4B C4AB 1.425(4) . ? C4B H4BA 0.9300 . ? C4AB C9B 1.402(4) 2_666 ? 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 C4A C9 C9A 123.3(3) 2 . ? C4A C9 Cl1 118.5(2) 2 . ? C9A C9 Cl1 118.2(3) . . ? C1 C9A C9 123.4(3) . . ? C1 C9A C4A 118.4(3) . . ? C9 C9A C4A 118.2(3) . . ? C2 C1 C9A 121.1(3) . . ? C2 C1 H1A 119.5 . . ? C9A C1 H1A 119.5 . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C4A 121.9(3) . . ? C3 C4 H4A 119.1 . . ? C4A C4 H4A 119.1 . . ? C9 C4A C9A 118.5(3) 2 . ? C9 C4A C4 123.7(3) 2 . ? C9A C4A C4 117.8(3) . . ? C9AB C9B C4AB 123.3(3) . 2_666 ? C9AB C9B Cl2 118.3(2) . . ? C4AB C9B Cl2 118.4(2) 2_666 . ? C9B C9AB C4AB 118.4(3) . . ? C9B C9AB C1B 123.8(3) . . ? C4AB C9AB C1B 117.7(3) . . ? C2B C1B C9AB 122.0(3) . . ? C2B C1B H1B 119.0 . . ? C9AB C1B H1B 119.0 . . ? C1B C2B C3B 120.3(3) . . ? C1B C2B H2BA 119.9 . . ? C3B C2B H2BA 119.9 . . ? C4B C3B C2B 120.4(3) . . ? C4B C3B H3BA 119.8 . . ? C2B C3B H3BA 119.8 . . ? C3B C4B C4AB 121.4(3) . . ? C3B C4B H4BA 119.3 . . ? C4AB C4B H4BA 119.3 . . ? C9B C4AB C4B 123.5(3) 2_666 . ? C9B C4AB C9AB 118.3(3) 2_666 . ? C4B C4AB C9AB 118.3(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 73.92 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.777 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.110 #========================================================================== data_3a _database_code_depnum_ccdc_archive 'CCDC 216307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dichloroanthracene:dibromoanthracene ; _chemical_name_common dichloroanthracene:dibromoanthracene _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 Br.50 Cl1.50' _chemical_formula_weight 269.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 '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 3.8629(9) _cell_length_b 8.743(2) _cell_length_c 16.515(4) _cell_angle_alpha 105.203(4) _cell_angle_beta 90.179(5) _cell_angle_gamma 100.495(5) _cell_volume 528.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 1018 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 26.51 _exptl_crystal_description 'fragment of needle' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 270 _exptl_absorpt_coefficient_mu 2.340 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (1996)' _exptl_absorpt_correction_T_min 0.4546 _exptl_absorpt_correction_T_max 0.8533 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _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 'CCD area detector' _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 7278 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.37 _reflns_number_total 2621 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0500P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2621 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.011 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.31763(9) 0.28316(4) 0.15673(2) 0.02153(13) Uani 0.7102(11) d P . . Br1 Br 0.33624(9) 0.29781(4) 0.16464(2) 0.02153(13) Uani 0.2898(11) d PR . . C9 C 0.1407(5) 0.1254(2) 0.06956(11) 0.0177(4) Uani 1 d . . . C9A C 0.2312(5) 0.1403(2) -0.01086(11) 0.0172(4) Uani 1 d . . . C1 C 0.4628(5) 0.2782(2) -0.02445(12) 0.0201(4) Uani 1 d . . . H1A H 0.5603 0.3627 0.0214 0.024 Uiso 1 calc R . . C2 C 0.5421(5) 0.2875(2) -0.10368(13) 0.0230(4) Uani 1 d . . . H2A H 0.6917 0.3781 -0.1114 0.028 Uiso 1 calc R . . C3 C 0.3977(5) 0.1594(2) -0.17440(12) 0.0229(4) Uani 1 d . . . H3A H 0.4551 0.1668 -0.2281 0.027 Uiso 1 calc R . . C4 C 0.1763(5) 0.0259(2) -0.16485(12) 0.0212(4) Uani 1 d . . . H4A H 0.0828 -0.0562 -0.2121 0.025 Uiso 1 calc R . . C4A C 0.0851(5) 0.0104(2) -0.08279(11) 0.0166(4) Uani 1 d . . . Cl2 Cl 0.42644(9) 0.83714(5) 0.61721(2) 0.02201(13) Uani 0.7926(11) d P . . Br2 Br 0.42269(9) 0.85476(5) 0.62308(2) 0.02201(13) Uani 0.2074(11) d PR . . C9B C 0.4659(5) 0.6496(2) 0.55162(11) 0.0162(4) Uani 1 d . . . C9AB C 0.3406(4) 0.5115(2) 0.57895(11) 0.0152(3) Uani 1 d . . . C1B C 0.1790(5) 0.5171(2) 0.65710(12) 0.0199(4) Uani 1 d . . . H1B H 0.1534 0.6162 0.6921 0.024 Uiso 1 calc R . . C2B C 0.0615(5) 0.3798(2) 0.68135(12) 0.0221(4) Uani 1 d . . . H2BA H -0.0410 0.3864 0.7327 0.027 Uiso 1 calc R . . C3B C 0.0949(5) 0.2271(2) 0.62852(12) 0.0217(4) Uani 1 d . . . H3BA H 0.0121 0.1341 0.6454 0.026 Uiso 1 calc R . . C4B C 0.2474(5) 0.2151(2) 0.55313(12) 0.0197(4) Uani 1 d . . . H4BA H 0.2688 0.1141 0.5195 0.024 Uiso 1 calc R . . C4AB C 0.3750(4) 0.3563(2) 0.52528(11) 0.0161(4) Uani 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 Cl1 0.0233(2) 0.0201(2) 0.01784(19) -0.00077(13) -0.00053(13) 0.00423(13) Br1 0.0233(2) 0.0201(2) 0.01784(19) -0.00077(13) -0.00053(13) 0.00423(13) C9 0.0193(9) 0.0168(8) 0.0166(9) 0.0000(7) -0.0006(7) 0.0086(7) C9A 0.0170(9) 0.0180(9) 0.0188(9) 0.0046(7) 0.0015(7) 0.0092(7) C1 0.0197(9) 0.0169(9) 0.0241(10) 0.0047(7) 0.0017(7) 0.0059(7) C2 0.0219(10) 0.0211(9) 0.0301(11) 0.0119(8) 0.0061(8) 0.0069(8) C3 0.0236(10) 0.0294(10) 0.0204(10) 0.0112(8) 0.0046(8) 0.0101(8) C4 0.0235(10) 0.0237(10) 0.0180(9) 0.0043(7) 0.0020(7) 0.0104(8) C4A 0.0160(8) 0.0192(9) 0.0168(8) 0.0047(7) 0.0013(7) 0.0089(7) Cl2 0.0248(2) 0.0136(2) 0.0256(2) 0.00032(14) 0.00480(15) 0.00569(14) Br2 0.0248(2) 0.0136(2) 0.0256(2) 0.00032(14) 0.00480(15) 0.00569(14) C9B 0.0149(8) 0.0143(8) 0.0178(9) 0.0008(7) -0.0009(7) 0.0039(6) C9AB 0.0124(8) 0.0167(8) 0.0168(8) 0.0042(7) -0.0017(6) 0.0036(6) C1B 0.0184(9) 0.0229(9) 0.0183(9) 0.0042(7) 0.0017(7) 0.0050(7) C2B 0.0178(9) 0.0302(10) 0.0193(9) 0.0076(8) 0.0022(7) 0.0054(8) C3B 0.0195(9) 0.0211(9) 0.0265(10) 0.0113(8) -0.0002(7) 0.0016(7) C4B 0.0172(9) 0.0175(9) 0.0245(10) 0.0063(7) -0.0016(7) 0.0031(7) C4AB 0.0131(8) 0.0169(8) 0.0184(9) 0.0041(7) -0.0022(7) 0.0037(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 Cl1 C9 1.7466(18) . ? Br1 C9 1.9090(18) . ? C9 C9A 1.407(2) . ? C9 C4A 1.407(3) 2 ? C9A C1 1.433(3) . ? C9A C4A 1.440(2) . ? C1 C2 1.364(3) . ? C1 H1A 0.9300 . ? C2 C3 1.418(3) . ? C2 H2A 0.9300 . ? C3 C4 1.361(3) . ? C3 H3A 0.9300 . ? C4 C4A 1.436(3) . ? C4 H4A 0.9300 . ? C4A C9 1.407(3) 2 ? Cl2 C9B 1.7450(18) . ? Br2 C9B 1.9072(18) . ? C9B C9AB 1.404(2) . ? C9B C4AB 1.406(2) 2_666 ? C9AB C1B 1.429(2) . ? C9AB C4AB 1.442(2) . ? C1B C2B 1.365(3) . ? C1B H1B 0.9300 . ? C2B C3B 1.419(3) . ? C2B H2BA 0.9300 . ? C3B C4B 1.366(3) . ? C3B H3BA 0.9300 . ? C4B C4AB 1.434(2) . ? C4B H4BA 0.9300 . ? C4AB C9B 1.406(2) 2_666 ? 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 C9A C9 C4A 123.01(16) . 2 ? C9A C9 Cl1 118.30(14) . . ? C4A C9 Cl1 118.70(13) 2 . ? C9A C9 Br1 118.12(13) . . ? C4A C9 Br1 118.87(13) 2 . ? Cl1 C9 Br1 0.269(6) . . ? C9 C9A C1 123.09(17) . . ? C9 C9A C4A 118.34(16) . . ? C1 C9A C4A 118.57(16) . . ? C2 C1 C9A 120.98(18) . . ? C2 C1 H1A 119.5 . . ? C9A C1 H1A 119.5 . . ? C1 C2 C3 120.33(18) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C4 C3 C2 120.95(17) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C4A 120.85(18) . . ? C3 C4 H4A 119.6 . . ? C4A C4 H4A 119.6 . . ? C9 C4A C4 123.02(17) 2 . ? C9 C4A C9A 118.66(16) 2 . ? C4 C4A C9A 118.32(16) . . ? C9AB C9B C4AB 123.06(16) . 2_666 ? C9AB C9B Cl2 118.15(14) . . ? C4AB C9B Cl2 118.79(13) 2_666 . ? C9AB C9B Br2 118.27(13) . . ? C4AB C9B Br2 118.67(13) 2_666 . ? Cl2 C9B Br2 0.135(6) . . ? C9B C9AB C1B 123.22(16) . . ? C9B C9AB C4AB 118.39(16) . . ? C1B C9AB C4AB 118.39(16) . . ? C2B C1B C9AB 121.32(17) . . ? C2B C1B H1B 119.3 . . ? C9AB C1B H1B 119.3 . . ? C1B C2B C3B 120.29(18) . . ? C1B C2B H2BA 119.9 . . ? C3B C2B H2BA 119.9 . . ? C4B C3B C2B 120.72(17) . . ? C4B C3B H3BA 119.6 . . ? C2B C3B H3BA 119.6 . . ? C3B C4B C4AB 120.81(17) . . ? C3B C4B H4BA 119.6 . . ? C4AB C4B H4BA 119.6 . . ? C9B C4AB C4B 122.98(16) 2_666 . ? C9B C4AB C9AB 118.56(15) 2_666 . ? C4B C4AB C9AB 118.47(16) . . ? _diffrn_measured_fraction_theta_max .994 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full .994 _refine_diff_density_max .465 _refine_diff_density_min -.243 _refine_diff_density_rms .081