# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_nik33sqz _database_code_depnum_ccdc_archive 'CCDC 887828' #TrackingRef 'nik33pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Br2 P, C H2 Cl2' _chemical_formula_sum 'C19 H17 Br2 Cl2 P' _chemical_formula_weight 507.02 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' Cl Cl 0.1484 0.1585 '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 cubic _symmetry_space_group_name_H-M 'P a -3' _symmetry_space_group_name_Hall '-P 2ac 2ab 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' '-z, -x, -y' '-z-1/2, x-1/2, y' 'z-1/2, x, -y-1/2' 'z, -x-1/2, y-1/2' '-y, -z, -x' 'y, -z-1/2, x-1/2' '-y-1/2, z-1/2, x' 'y-1/2, z, -x-1/2' _cell_length_a 16.1626(2) _cell_length_b 16.1626(2) _cell_length_c 16.1626(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4222.15(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3784 _cell_measurement_theta_min 3.5582 _cell_measurement_theta_max 24.0520 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1308 _exptl_crystal_size_mid 0.1037 _exptl_crystal_size_min 0.0976 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 4.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83854 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; The PLATON "squeeze" procedure was used to treat regions of diffuse solvent(s) which could not be modelled in terms of atomic sites. The number of electrons thus located, 320 per unit cell, is included in the formula, formula weight, calculated density, \m and F(000). This residual electron density was assigned to 8 molecules of dichloromethane per unit cell. Four dichloromethanes would give 336 e^-^. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11953 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 24.10 _reflns_number_total 1127 _reflns_number_gt 985 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+7.4404P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1127 _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.19121(8) 0.19121(8) 0.19121(8) 0.0250(5) Uani 1 3 d S . . Br1 Br 0.11375(3) 0.11375(3) 0.11375(3) 0.0253(3) Uani 1 3 d S . . C1 C 0.2772(3) 0.1307(3) 0.2267(3) 0.0283(11) Uani 1 1 d . . . C2 C 0.3190(3) 0.0806(3) 0.1720(3) 0.0329(12) Uani 1 1 d . . . H2 H 0.3009 0.0758 0.1163 0.039 Uiso 1 1 calc R . . C3 C 0.3879(3) 0.0370(3) 0.1992(4) 0.0370(13) Uani 1 1 d . . . H3 H 0.4178 0.0027 0.1620 0.044 Uiso 1 1 calc R . . C4 C 0.4128(3) 0.0438(4) 0.2808(4) 0.0375(14) Uani 1 1 d . . . H4 H 0.4593 0.0131 0.2997 0.045 Uiso 1 1 calc R . . C5 C 0.3715(4) 0.0940(4) 0.3345(4) 0.0453(16) Uani 1 1 d . . . H5 H 0.3901 0.0989 0.3900 0.054 Uiso 1 1 calc R . . C6 C 0.3023(4) 0.1382(4) 0.3083(3) 0.0410(14) Uani 1 1 d . . . H6 H 0.2729 0.1728 0.3457 0.049 Uiso 1 1 calc R . . Br2 Br 0.0000 0.0000 0.0000 0.0209(4) Uani 1 6 d S . . Br3 Br 0.98028(7) 0.48028(7) 0.01972(7) 0.0356(5) Uani 0.50 3 d SP . . 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 P 0.0250(5) 0.0250(5) 0.0250(5) -0.0044(5) -0.0044(5) -0.0044(5) Br1 0.0253(3) 0.0253(3) 0.0253(3) -0.00431(18) -0.00431(18) -0.00431(18) C1 0.024(3) 0.029(3) 0.031(3) -0.001(2) -0.004(2) -0.003(2) C2 0.035(3) 0.036(3) 0.027(3) -0.004(2) -0.009(2) -0.002(2) C3 0.035(3) 0.036(3) 0.040(3) -0.005(3) -0.002(3) 0.002(2) C4 0.028(3) 0.044(3) 0.041(3) 0.014(3) -0.005(3) -0.003(3) C5 0.035(3) 0.072(4) 0.029(3) 0.002(3) -0.008(3) 0.002(3) C6 0.042(3) 0.055(4) 0.026(3) -0.005(3) -0.002(2) 0.001(3) Br2 0.0209(4) 0.0209(4) 0.0209(4) -0.0017(2) -0.0017(2) -0.0017(2) Br3 0.0356(5) 0.0356(5) 0.0356(5) -0.0041(4) -0.0041(4) 0.0041(4) _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 P C1 1.793(5) 9 ? P C1 1.793(5) 5 ? P C1 1.793(5) . ? P Br1 2.168(2) . ? C1 C2 1.376(8) . ? C1 C6 1.386(8) . ? C2 C3 1.390(8) . ? C2 H2 0.9500 . ? C3 C4 1.384(8) . ? C3 H3 0.9500 . ? C4 C5 1.362(9) . ? C4 H4 0.9500 . ? C5 C6 1.393(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 C1 P C1 110.46(16) 9 5 ? C1 P C1 110.46(16) 9 . ? C1 P C1 110.46(16) 5 . ? C1 P Br1 108.46(17) 9 . ? C1 P Br1 108.46(17) 5 . ? C1 P Br1 108.46(17) . . ? C2 C1 C6 121.3(5) . . ? C2 C1 P 119.8(4) . . ? C6 C1 P 118.9(4) . . ? C1 C2 C3 119.3(5) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 120.8(5) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.4(6) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.6(6) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? 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 C1 P C1 C2 163.6(4) 9 . . . ? C1 P C1 C2 -73.9(6) 5 . . . ? Br1 P C1 C2 44.8(5) . . . . ? C1 P C1 C6 -19.2(6) 9 . . . ? C1 P C1 C6 103.3(4) 5 . . . ? Br1 P C1 C6 -137.9(4) . . . . ? C6 C1 C2 C3 -0.3(8) . . . . ? P C1 C2 C3 176.9(4) . . . . ? C1 C2 C3 C4 0.8(8) . . . . ? C2 C3 C4 C5 -1.3(9) . . . . ? C3 C4 C5 C6 1.3(9) . . . . ? C2 C1 C6 C5 0.2(9) . . . . ? P C1 C6 C5 -177.0(5) . . . . ? C4 C5 C6 C1 -0.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.607 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.112 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.135 0.135 0.635 136 40 'C H2 Cl2' 2 -0.135 0.365 0.135 136 40 'C H2 Cl2' 3 0.135 0.635 0.865 136 40 'C H2 Cl2' 4 0.135 0.865 0.365 136 40 'C H2 Cl2' 5 0.365 0.135 0.865 136 40 'C H2 Cl2' 6 0.365 0.365 0.365 136 40 'C H2 Cl2' 7 0.635 0.635 0.635 136 40 'C H2 Cl2' 8 0.635 0.865 0.135 136 40 'C H2 Cl2' _platon_squeeze_details ; PLATON: A.L. Spek, J. Appl. Cryst. 36 (2003), 7-13 PLATON version from 30.03.2011 ; data_nik39 _database_code_depnum_ccdc_archive 'CCDC 887829' #TrackingRef 'nik33pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Cl P, C H2 Cl2, 0.69 (Br), 0.31 (Cl)' _chemical_formula_sum 'C19 H17 Br0.69 Cl3.32 P' _chemical_formula_weight 448.71 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' Cl Cl 0.1484 0.1585 '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 cubic _symmetry_space_group_name_H-M 'P a -3' _symmetry_space_group_name_Hall '-P 2ac 2ab 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' '-z, -x, -y' '-z-1/2, x-1/2, y' 'z-1/2, x, -y-1/2' 'z, -x-1/2, y-1/2' '-y, -z, -x' 'y, -z-1/2, x-1/2' '-y-1/2, z-1/2, x' 'y-1/2, z, -x-1/2' _cell_length_a 15.9738(2) _cell_length_b 15.9738(2) _cell_length_c 15.9738(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4075.91(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5113 _cell_measurement_theta_min 2.8456 _cell_measurement_theta_max 29.3045 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2921 _exptl_crystal_size_mid 0.2261 _exptl_crystal_size_min 0.2163 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1811.0 _exptl_absorpt_coefficient_mu 1.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90662 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12333 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.37 _reflns_number_total 1773 _reflns_number_gt 1495 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+7.7690P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1773 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.19024(3) 0.19024(3) 0.19024(3) 0.0132(2) Uani 1 3 d S . . Cl1 Cl 0.11791(3) 0.11791(3) 0.11791(3) 0.0173(2) Uani 1 3 d S . . C1 C 0.27634(14) 0.12885(14) 0.22553(15) 0.0151(4) Uani 1 1 d . . . C2 C 0.32108(16) 0.07979(16) 0.16836(15) 0.0194(5) Uani 1 1 d . . . H2 H 0.3038 0.0767 0.1115 0.023 Uiso 1 1 calc R . . C3 C 0.39076(16) 0.03586(16) 0.19548(17) 0.0228(5) Uani 1 1 d . . . H3 H 0.4213 0.0020 0.1573 0.027 Uiso 1 1 calc R . . C4 C 0.41604(16) 0.04140(16) 0.27867(17) 0.0225(5) Uani 1 1 d . . . H4 H 0.4639 0.0113 0.2970 0.027 Uiso 1 1 calc R . . C5 C 0.37198(17) 0.09049(18) 0.33498(16) 0.0255(6) Uani 1 1 d . . . H5 H 0.3900 0.0941 0.3915 0.031 Uiso 1 1 calc R . . C6 C 0.30161(16) 0.13450(17) 0.30907(16) 0.0219(5) Uani 1 1 d . . . H6 H 0.2711 0.1680 0.3476 0.026 Uiso 1 1 calc R . . Br1 Br 0.0000 0.0000 0.0000 0.01615(18) Uani 1 6 d S . . Br2 Br 0.5000 0.0000 0.0000 0.0316(5) Uani 0.376(8) 6 d SP A 1 Cl2 Cl 0.5000 0.0000 0.0000 0.0316(5) Uani 0.624(8) 6 d SP A 2 C7 C 0.3755(3) 0.3755(3) 0.3755(3) 0.066(2) Uani 1 3 d S . . H7A H 0.3964 0.3383 0.3328 0.080 Uiso 0.33333 1 d PR . . H7B H 0.4226 0.4026 0.4008 0.080 Uiso 0.33333 1 d PR . . Cl3 Cl 0.32832(15) 0.31663(12) 0.44902(10) 0.0794(7) Uani 0.66667 1 d P . . 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 P 0.0132(2) 0.0132(2) 0.0132(2) -0.0018(2) -0.0018(2) -0.0018(2) Cl1 0.0173(2) 0.0173(2) 0.0173(2) -0.00372(19) -0.00372(19) -0.00372(19) C1 0.0153(10) 0.0144(10) 0.0156(11) 0.0002(8) -0.0013(8) -0.0003(8) C2 0.0221(12) 0.0210(12) 0.0150(11) -0.0027(9) -0.0015(9) 0.0009(9) C3 0.0214(12) 0.0210(12) 0.0259(13) -0.0019(10) 0.0018(10) 0.0035(10) C4 0.0177(12) 0.0223(12) 0.0273(13) 0.0085(10) -0.0011(10) 0.0010(9) C5 0.0230(13) 0.0372(15) 0.0164(12) 0.0047(11) -0.0038(10) 0.0033(11) C6 0.0208(12) 0.0299(13) 0.0151(11) -0.0027(10) -0.0011(9) 0.0033(10) Br1 0.01615(18) 0.01615(18) 0.01615(18) 0.00009(11) 0.00009(11) 0.00009(11) Br2 0.0316(5) 0.0316(5) 0.0316(5) -0.0064(3) 0.0064(3) -0.0064(3) Cl2 0.0316(5) 0.0316(5) 0.0316(5) -0.0064(3) 0.0064(3) -0.0064(3) C7 0.066(2) 0.066(2) 0.066(2) -0.009(2) -0.009(2) -0.009(2) Cl3 0.1267(17) 0.0718(11) 0.0397(8) -0.0141(7) 0.0091(9) -0.0520(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P C1 1.781(2) . ? P C1 1.781(2) 9 ? P C1 1.781(2) 5 ? P Cl1 2.0011(13) . ? C1 C6 1.397(3) . ? C1 C2 1.400(3) . ? C2 C3 1.385(4) . ? C2 H2 0.9500 . ? C3 C4 1.392(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.389(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 Cl3 1.683(2) . ? C7 Cl3 1.683(2) 9 ? C7 Cl3 1.683(2) 5 ? C7 H7A 0.9640 . ? C7 H7B 0.9572 . ? 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 C1 P C1 110.80(7) . 9 ? C1 P C1 110.80(7) . 5 ? C1 P C1 110.80(7) 9 5 ? C1 P Cl1 108.10(8) . . ? C1 P Cl1 108.10(8) 9 . ? C1 P Cl1 108.10(8) 5 . ? C6 C1 C2 120.8(2) . . ? C6 C1 P 119.34(18) . . ? C2 C1 P 119.75(18) . . ? C3 C2 C1 119.3(2) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.0(2) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? Cl3 C7 Cl3 116.89(17) . 9 ? Cl3 C7 Cl3 116.90(17) . 5 ? Cl3 C7 Cl3 116.89(17) 9 5 ? Cl3 C7 H7A 107.7 . . ? Cl3 C7 H7A 107.9 9 . ? Cl3 C7 H7B 108.0 . . ? Cl3 C7 H7B 108.2 9 . ? H7A C7 H7B 107.8 . . ? 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 C1 P C1 C6 -18.4(2) 9 . . . ? C1 P C1 C6 104.98(16) 5 . . . ? Cl1 P C1 C6 -136.73(18) . . . . ? C1 P C1 C2 165.62(18) 9 . . . ? C1 P C1 C2 -71.0(3) 5 . . . ? Cl1 P C1 C2 47.3(2) . . . . ? C6 C1 C2 C3 0.6(4) . . . . ? P C1 C2 C3 176.47(19) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? P C1 C6 C5 -176.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.161 _refine_diff_density_min -1.846 _refine_diff_density_rms 0.101