# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #=============================================================================== _publ_contact_author_name 'Pierangelo Metrangolo, Giuseppe Resnati' _publ_contact_author_email 'pierangelo.metrangolo@polimi.it, giuseppe.resnati@polimi.it' #=============================================================================== _publ_section_title ; ; _publ_section_title_footnote ; ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Susanta K. Nayak' ; Center for Nano Science and Technology@Polimi, Istituo Italiano di Technologia, Via Pascoli 70/3, Milan-20133, Italy ; 'Giancarlo Terraneo' ; NFMLab-"DCMIC G. Natta" Politecnico di Milano, Via Mancinelli 7, Milan-20131, Italy Center for Nano Science and Technology@Polimi, Istituo Italiano di Technologia, Via Pascoli 70/3, Milan-20133, Italy ; 'Alessandra Forni' ; ISTM-CNR, Universita` di Milano, Via Venezian 21, I-20133 Milan, Italy ; 'Pierangelo Metrangolo' ; NFMLab-"DCMIC G. Natta" Politecnico di Milano, Via Mancinelli 7, Milan-20131, Italy Center for Nano Science and Technology@Polimi, Istituo Italiano di Technologia, Via Pascoli 70/3, Milan-20133, Italy ; 'Giuseppe Resnati' ; NFMLab-"DCMIC G. Natta" Politecnico di Milano, Via Mancinelli 7, Milan-20131, Italy Center for Nano Science and Technology@Polimi, Istituo Italiano di Technologia, Via Pascoli 70/3, Milan-20133, Italy ; #=============================================================================== data_DBTFB _database_code_depnum_ccdc_archive 'CCDC 849566' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibromotetrafluorobenzene ; _chemical_name_common Dibromotetrafluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 Br2 F4' _chemical_formula_weight 307.88 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.1014(10) _cell_length_b 24.246(5) _cell_length_c 5.1617(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.598(9) _cell_angle_gamma 90.00 _cell_volume 762.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.89 _exptl_crystal_description CYCLINDER _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 10.642 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.1425 _exptl_absorpt_correction_T_max 0.2247 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization Procedure A 0.3 mm Lindemann capillary of around 3 cm length was filled with the DBTFB. The capillary was then sealed by melting at both ends, then mounted in the diffractometer equipped with a Bruker KRIOFLEX low temperature device and an Optical Heating and Crystallization Device (OHCD) for the in situ cryocrystallization. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7006 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1503 _reflns_number_gt 1278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0271P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1503 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0522 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 Br1 Br 0.65224(5) 0.190623(13) 0.97556(5) 0.02445(11) Uani 1 1 d . . . Br2 Br 0.75772(5) 0.020271(13) 0.23939(6) 0.03196(11) Uani 1 1 d . . . F1 F 0.5525(2) 0.08673(7) 0.6606(3) 0.0278(4) Uani 1 1 d . . . F2 F 1.1805(3) 0.08505(7) 0.1703(3) 0.0294(4) Uani 1 1 d . . . F3 F 1.3279(2) 0.17706(7) 0.4136(3) 0.0227(4) Uani 1 1 d . . . F4 F 1.0966(3) 0.22356(7) 0.7843(3) 0.0220(4) Uani 1 1 d . . . C1 C 0.8186(4) 0.15590(12) 0.7279(5) 0.0161(6) Uani 1 1 d . . . C2 C 0.7460(4) 0.10865(12) 0.6006(5) 0.0187(6) Uani 1 1 d . . . C3 C 0.8636(5) 0.08361(12) 0.4132(5) 0.0197(6) Uani 1 1 d . . . C4 C 1.0607(5) 0.10713(12) 0.3537(5) 0.0186(6) Uani 1 1 d . . . C5 C 1.1371(4) 0.15423(12) 0.4769(5) 0.0166(6) Uani 1 1 d . . . C6 C 1.0182(4) 0.17855(11) 0.6637(5) 0.0154(6) 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 0.02052(17) 0.03379(19) 0.01986(16) 0.00214(13) 0.00774(12) 0.00596(13) Br2 0.0341(2) 0.01815(17) 0.0422(2) -0.00529(13) -0.00892(15) -0.00209(13) F1 0.0164(8) 0.0282(10) 0.0389(10) 0.0099(8) 0.0038(8) -0.0061(8) F2 0.0296(10) 0.0306(10) 0.0290(9) -0.0085(8) 0.0080(8) 0.0081(8) F3 0.0148(8) 0.0277(10) 0.0262(9) 0.0024(7) 0.0064(7) -0.0007(7) F4 0.0211(9) 0.0207(9) 0.0242(8) -0.0065(7) 0.0009(7) -0.0030(7) C1 0.0125(13) 0.0231(15) 0.0131(13) 0.0035(12) 0.0040(11) 0.0044(12) C2 0.0124(14) 0.0197(15) 0.0240(15) 0.0087(12) -0.0001(12) -0.0020(12) C3 0.0216(15) 0.0122(14) 0.0246(14) 0.0016(12) -0.0041(12) 0.0001(12) C4 0.0181(14) 0.0201(15) 0.0178(14) -0.0010(12) 0.0021(12) 0.0046(12) C5 0.0104(13) 0.0184(14) 0.0213(14) 0.0065(12) 0.0034(11) 0.0011(11) C6 0.0155(14) 0.0136(14) 0.0168(13) 0.0007(11) -0.0015(12) 0.0016(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.881(3) . ? Br2 C3 1.873(3) . ? F1 C2 1.349(3) . ? F2 C4 1.344(3) . ? F3 C5 1.348(3) . ? F4 C6 1.330(3) . ? C1 C2 1.380(4) . ? C1 C6 1.394(4) . ? C2 C3 1.381(4) . ? C3 C4 1.383(4) . ? C4 C5 1.374(4) . ? C5 C6 1.376(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 C2 C1 C6 118.2(2) . . ? C2 C1 Br1 121.6(2) . . ? C6 C1 Br1 120.1(2) . . ? F1 C2 C1 118.5(2) . . ? F1 C2 C3 119.2(3) . . ? C1 C2 C3 122.2(2) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 Br2 121.2(2) . . ? C4 C3 Br2 120.7(2) . . ? F2 C4 C5 118.2(2) . . ? F2 C4 C3 120.8(3) . . ? C5 C4 C3 121.0(3) . . ? F3 C5 C4 120.2(2) . . ? F3 C5 C6 119.7(3) . . ? C4 C5 C6 120.1(2) . . ? F4 C6 C5 119.3(2) . . ? F4 C6 C1 120.4(2) . . ? C5 C6 C1 120.3(3) . . ? 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 F1 -179.6(2) . . . . ? Br1 C1 C2 F1 -1.2(3) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? Br1 C1 C2 C3 178.2(2) . . . . ? F1 C2 C3 C4 179.5(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? F1 C2 C3 Br2 0.6(3) . . . . ? C1 C2 C3 Br2 -178.8(2) . . . . ? C2 C3 C4 F2 -179.0(2) . . . . ? Br2 C3 C4 F2 0.0(4) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? Br2 C3 C4 C5 178.7(2) . . . . ? F2 C4 C5 F3 -0.2(4) . . . . ? C3 C4 C5 F3 -179.0(2) . . . . ? F2 C4 C5 C6 179.2(2) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? F3 C5 C6 F4 -1.8(4) . . . . ? C4 C5 C6 F4 178.8(2) . . . . ? F3 C5 C6 C1 178.9(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C2 C1 C6 F4 -178.9(2) . . . . ? Br1 C1 C6 F4 2.7(3) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? Br1 C1 C6 C5 -177.99(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.461 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.088 #=============================================================================== data_DBTFB-HMPA _database_code_depnum_ccdc_archive 'CCDC 849567' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibromotetrafluorobenzene Hexamethyphosphoramide ; _chemical_name_common 'Dibromotetrafluorobenzene Hexamethyphosphoramide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Br2 F4 N3 O P' _chemical_formula_weight 487.08 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.751(3) _cell_length_b 8.9439(9) _cell_length_c 17.2175(18) _cell_angle_alpha 90.00 _cell_angle_beta 119.428(2) _cell_angle_gamma 90.00 _cell_volume 3587.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description cyclinder _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 4.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3360 _exptl_absorpt_correction_T_max 0.3360 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization Procedure A 0.3 mm Lindemann capillary of around 3 cm length was filled with the 1:1 mixture. The capillary was then sealed by melting at both ends, then mounted in the diffractometer equipped with a Bruker KRIOFLEX low temperature device and an Optical Heating and Crystallization Device (OHCD) for the in situ cryocrystallization. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13571 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3527 _reflns_number_gt 2920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0224P)^2^+5.2415P] 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 3527 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.086438(12) 0.73987(3) -0.050436(18) 0.03550(9) Uani 1 1 d . . . Br2 Br 0.077412(11) 1.09157(3) 0.215438(16) 0.02739(8) Uani 1 1 d . . . F1 F 0.11903(6) 0.97117(19) 0.09490(11) 0.0376(4) Uani 1 1 d . . . F2 F -0.03431(7) 0.90693(19) 0.15239(10) 0.0381(4) Uani 1 1 d . . . F3 F -0.07799(7) 0.6917(2) 0.02787(11) 0.0433(4) Uani 1 1 d . . . F4 F -0.02414(7) 0.61185(17) -0.06350(10) 0.0367(4) Uani 1 1 d . . . C1 C 0.04902(11) 0.7898(3) 0.01443(16) 0.0263(5) Uani 1 1 d . . . C2 C 0.07032(10) 0.9007(3) 0.07844(17) 0.0257(5) Uani 1 1 d . . . C3 C 0.04383(10) 0.9431(3) 0.12679(16) 0.0235(5) Uani 1 1 d . . . C4 C -0.00616(11) 0.8713(3) 0.10864(17) 0.0262(6) Uani 1 1 d . . . C5 C -0.02901(11) 0.7601(3) 0.04477(17) 0.0287(6) Uani 1 1 d . . . C6 C -0.00119(11) 0.7199(3) -0.00148(16) 0.0272(6) Uani 1 1 d . . . P1 P 0.17804(3) 0.43474(7) 0.34731(4) 0.02059(14) Uani 1 1 d . . . O1 O 0.14830(7) 0.3004(2) 0.35474(11) 0.0276(4) Uani 1 1 d . . . N1 N 0.23707(8) 0.4709(2) 0.44108(13) 0.0247(5) Uani 1 1 d . . . N2 N 0.13372(8) 0.5778(2) 0.31775(14) 0.0252(5) Uani 1 1 d . . . N3 N 0.20227(9) 0.4286(3) 0.27509(14) 0.0296(5) Uani 1 1 d . . . C7 C 0.23708(12) 0.4466(3) 0.52514(17) 0.0329(6) Uani 1 1 d . . . H7A H 0.2743 0.4059 0.5696 0.049 Uiso 1 1 calc R . . H7B H 0.2066 0.3758 0.5156 0.049 Uiso 1 1 calc R . . H7C H 0.2303 0.5418 0.5466 0.049 Uiso 1 1 calc R . . C8 C 0.28428(11) 0.5659(3) 0.45160(19) 0.0340(6) Uani 1 1 d . . . H8A H 0.2815 0.6634 0.4752 0.051 Uiso 1 1 calc R . . H8B H 0.2822 0.5795 0.3936 0.051 Uiso 1 1 calc R . . H8C H 0.3209 0.5186 0.4931 0.051 Uiso 1 1 calc R . . C9 C 0.07130(10) 0.5574(3) 0.26958(18) 0.0342(6) Uani 1 1 d . . . H9A H 0.0539 0.6212 0.2962 0.051 Uiso 1 1 calc R . . H9B H 0.0622 0.4525 0.2735 0.051 Uiso 1 1 calc R . . H9C H 0.0561 0.5848 0.2069 0.051 Uiso 1 1 calc R . . C10 C 0.15219(12) 0.7297(3) 0.3159(2) 0.0401(7) Uani 1 1 d . . . H10A H 0.1422 0.7562 0.2547 0.060 Uiso 1 1 calc R . . H10B H 0.1938 0.7370 0.3546 0.060 Uiso 1 1 calc R . . H10C H 0.1330 0.7984 0.3372 0.060 Uiso 1 1 calc R . . C11 C 0.16262(13) 0.4560(4) 0.18106(18) 0.0438(8) Uani 1 1 d . . . H11A H 0.1841 0.4906 0.1519 0.066 Uiso 1 1 calc R . . H11B H 0.1348 0.5325 0.1752 0.066 Uiso 1 1 calc R . . H11C H 0.1423 0.3632 0.1528 0.066 Uiso 1 1 calc R . . C12 C 0.24516(13) 0.3147(4) 0.2887(2) 0.0465(8) Uani 1 1 d . . . H12A H 0.2258 0.2201 0.2621 0.070 Uiso 1 1 calc R . . H12B H 0.2710 0.3006 0.3527 0.070 Uiso 1 1 calc R . . H12C H 0.2674 0.3472 0.2603 0.070 Uiso 1 1 calc R . . 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 0.03626(16) 0.03898(17) 0.03135(15) -0.00454(12) 0.01668(12) 0.00756(12) Br2 0.03376(14) 0.02106(13) 0.02455(13) -0.00125(11) 0.01216(11) -0.00034(11) F1 0.0282(8) 0.0459(10) 0.0409(9) -0.0112(8) 0.0187(7) -0.0083(7) F2 0.0400(9) 0.0443(10) 0.0390(9) -0.0051(8) 0.0263(8) -0.0066(8) F3 0.0412(10) 0.0483(10) 0.0392(9) -0.0057(8) 0.0187(8) -0.0219(8) F4 0.0485(10) 0.0250(8) 0.0258(8) -0.0043(7) 0.0099(7) -0.0050(7) C1 0.0277(13) 0.0264(14) 0.0226(13) 0.0025(11) 0.0107(11) 0.0077(11) C2 0.0218(12) 0.0254(13) 0.0257(13) 0.0007(11) 0.0085(10) 0.0010(11) C3 0.0260(13) 0.0187(12) 0.0202(12) 0.0026(10) 0.0071(10) 0.0031(10) C4 0.0297(13) 0.0251(14) 0.0232(13) 0.0052(11) 0.0125(11) 0.0030(10) C5 0.0280(14) 0.0274(14) 0.0257(13) 0.0038(11) 0.0094(11) -0.0057(11) C6 0.0329(14) 0.0199(13) 0.0190(12) 0.0021(10) 0.0053(11) 0.0010(11) P1 0.0201(3) 0.0230(3) 0.0189(3) 0.0018(3) 0.0098(2) 0.0027(3) O1 0.0303(10) 0.0255(9) 0.0260(9) 0.0000(8) 0.0131(8) -0.0027(8) N1 0.0223(11) 0.0289(12) 0.0216(11) 0.0015(9) 0.0097(9) 0.0011(9) N2 0.0196(10) 0.0249(11) 0.0279(11) 0.0039(9) 0.0093(9) 0.0035(9) N3 0.0272(11) 0.0417(14) 0.0240(11) -0.0001(10) 0.0156(9) 0.0042(10) C7 0.0386(15) 0.0336(15) 0.0214(13) 0.0004(12) 0.0108(12) -0.0005(12) C8 0.0238(13) 0.0415(17) 0.0334(15) -0.0003(13) 0.0115(11) -0.0001(12) C9 0.0208(13) 0.0442(17) 0.0330(15) 0.0013(13) 0.0096(11) 0.0092(12) C10 0.0322(16) 0.0281(15) 0.0471(18) 0.0081(14) 0.0094(13) 0.0047(12) C11 0.0376(16) 0.071(2) 0.0245(15) -0.0026(15) 0.0166(13) -0.0040(15) C12 0.0455(18) 0.057(2) 0.0461(18) -0.0056(17) 0.0297(16) 0.0120(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.884(2) . ? Br2 C3 1.885(2) . ? F1 C2 1.346(3) . ? F2 C4 1.339(3) . ? F3 C5 1.342(3) . ? F4 C6 1.344(3) . ? C1 C2 1.380(4) . ? C1 C6 1.382(4) . ? C2 C3 1.385(3) . ? C3 C4 1.374(4) . ? C4 C5 1.382(4) . ? C5 C6 1.378(4) . ? P1 O1 1.4807(18) . ? P1 N1 1.643(2) . ? P1 N2 1.646(2) . ? P1 N3 1.662(2) . ? N1 C8 1.457(3) . ? N1 C7 1.463(3) . ? N2 C10 1.451(3) . ? N2 C9 1.466(3) . ? N3 C11 1.456(3) . ? N3 C12 1.465(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.6(2) . . ? C2 C1 Br1 120.84(19) . . ? C6 C1 Br1 121.54(19) . . ? F1 C2 C1 118.8(2) . . ? F1 C2 C3 118.3(2) . . ? C1 C2 C3 123.0(2) . . ? C4 C3 C2 117.6(2) . . ? C4 C3 Br2 122.48(19) . . ? C2 C3 Br2 119.90(19) . . ? F2 C4 C3 120.9(2) . . ? F2 C4 C5 117.9(2) . . ? C3 C4 C5 121.2(2) . . ? F3 C5 C6 120.2(2) . . ? F3 C5 C4 120.2(2) . . ? C6 C5 C4 119.6(2) . . ? F4 C6 C5 118.7(2) . . ? F4 C6 C1 120.2(2) . . ? C5 C6 C1 121.1(2) . . ? O1 P1 N1 111.88(11) . . ? O1 P1 N2 108.74(11) . . ? N1 P1 N2 110.45(11) . . ? O1 P1 N3 117.48(11) . . ? N1 P1 N3 101.66(11) . . ? N2 P1 N3 106.32(11) . . ? C8 N1 C7 112.6(2) . . ? C8 N1 P1 126.34(18) . . ? C7 N1 P1 118.40(17) . . ? C10 N2 C9 114.2(2) . . ? C10 N2 P1 122.22(17) . . ? C9 N2 P1 121.69(18) . . ? C11 N3 C12 112.4(2) . . ? C11 N3 P1 119.19(18) . . ? C12 N3 P1 117.82(19) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 F1 -179.7(2) . . . . ? Br1 C1 C2 F1 -1.1(3) . . . . ? C6 C1 C2 C3 0.4(4) . . . . ? Br1 C1 C2 C3 178.91(19) . . . . ? F1 C2 C3 C4 179.4(2) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? F1 C2 C3 Br2 -1.9(3) . . . . ? C1 C2 C3 Br2 178.05(19) . . . . ? C2 C3 C4 F2 -179.6(2) . . . . ? Br2 C3 C4 F2 1.7(3) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? Br2 C3 C4 C5 -178.32(19) . . . . ? F2 C4 C5 F3 0.2(4) . . . . ? C3 C4 C5 F3 -179.8(2) . . . . ? F2 C4 C5 C6 -179.8(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? F3 C5 C6 F4 0.1(4) . . . . ? C4 C5 C6 F4 -179.8(2) . . . . ? F3 C5 C6 C1 179.5(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C2 C1 C6 F4 179.5(2) . . . . ? Br1 C1 C6 F4 1.0(3) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? Br1 C1 C6 C5 -178.30(19) . . . . ? O1 P1 N1 C8 162.0(2) . . . . ? N2 P1 N1 C8 -76.7(2) . . . . ? N3 P1 N1 C8 35.8(2) . . . . ? O1 P1 N1 C7 -37.9(2) . . . . ? N2 P1 N1 C7 83.4(2) . . . . ? N3 P1 N1 C7 -164.09(19) . . . . ? O1 P1 N2 C10 171.9(2) . . . . ? N1 P1 N2 C10 48.8(2) . . . . ? N3 P1 N2 C10 -60.7(2) . . . . ? O1 P1 N2 C9 -24.7(2) . . . . ? N1 P1 N2 C9 -147.80(19) . . . . ? N3 P1 N2 C9 102.7(2) . . . . ? O1 P1 N3 C11 81.0(2) . . . . ? N1 P1 N3 C11 -156.6(2) . . . . ? N2 P1 N3 C11 -41.0(3) . . . . ? O1 P1 N3 C12 -60.9(2) . . . . ? N1 P1 N3 C12 61.5(2) . . . . ? N2 P1 N3 C12 177.1(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.443 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.069 #=============================================================================== data_DBTFB-DMSO _database_code_depnum_ccdc_archive 'CCDC 849568' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibromotetrafluorobenzene Dimethyl sulfoxide ; _chemical_name_common 'Dibromotetrafluorobenzene Dimethyl sulfoxide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 Br2 F4 O S' _chemical_formula_weight 386.01 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 10.1518(19) _cell_length_b 5.3303(11) _cell_length_c 21.945(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1187.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 400 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.0 _exptl_crystal_description cyclinder _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 7.029 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2269 _exptl_absorpt_correction_T_max 0.2269 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization Procedure A 0.3 mm Lindemann capillary of around 3 cm length was filled with the 1:1 mixture. The capillary was then sealed by melting at both ends, then mounted in the diffractometer equipped with a Bruker KRIOFLEX low temperature device and an Optical Heating and Crystallization Device (OHCD) for the in situ cryocrystallization. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5193 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2190 _reflns_number_gt 1775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0655P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 2190 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.089 _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 Br1 Br 0.85183(10) 0.9685(2) 0.37793(5) 0.0246(3) Uani 1 1 d . . . Br2 Br 0.80129(9) 0.6296(2) 0.62281(5) 0.0210(3) Uani 1 1 d . . . S1 S 0.7245(3) 0.1386(5) 0.72848(12) 0.0163(6) Uani 1 1 d . . . O1 O 0.7083(8) 0.4043(16) 0.7525(4) 0.025(2) Uani 1 1 d . . . F1 F 0.7598(7) 0.6511(14) 0.4843(3) 0.0279(16) Uani 1 1 d . . . F2 F 0.9950(6) 1.0580(14) 0.6434(2) 0.0241(16) Uani 1 1 d . . . F3 F 1.0976(7) 1.3790(14) 0.5607(3) 0.0323(17) Uani 1 1 d . . . F4 F 1.0352(7) 1.3425(14) 0.4411(3) 0.0332(17) Uani 1 1 d . . . C3 C 0.8762(10) 0.849(2) 0.5659(5) 0.020(2) Uani 1 1 d . . . C2 C 0.8437(10) 0.835(2) 0.5022(5) 0.018(2) Uani 1 1 d . . . C1 C 0.8954(11) 0.993(2) 0.4591(5) 0.020(2) Uani 1 1 d . . . C6 C 0.9806(10) 1.180(2) 0.4791(5) 0.022(3) Uani 1 1 d . . . C4 C 0.9620(10) 1.032(2) 0.5833(5) 0.021(2) Uani 1 1 d . . . C5 C 1.0142(11) 1.200(2) 0.5420(5) 0.023(3) Uani 1 1 d . . . C7 C 0.5762(10) -0.031(2) 0.7496(5) 0.024(3) Uani 1 1 d . . . H7A H 0.5007 0.0393 0.7276 0.037 Uiso 1 1 calc R . . H7B H 0.5616 -0.0145 0.7936 0.037 Uiso 1 1 calc R . . H7C H 0.5863 -0.2084 0.7391 0.037 Uiso 1 1 calc R . . C8 C 0.8302(10) -0.020(2) 0.7824(5) 0.024(3) Uani 1 1 d . . . H8A H 0.7987 0.0121 0.8239 0.036 Uiso 1 1 calc R . . H8B H 0.9205 0.0431 0.7782 0.036 Uiso 1 1 calc R . . H8C H 0.8288 -0.2006 0.7744 0.036 Uiso 1 1 calc R . . 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 0.0319(5) 0.0290(7) 0.0130(5) 0.0015(6) 0.0018(5) 0.0017(5) Br2 0.0251(5) 0.0209(6) 0.0171(5) 0.0046(5) 0.0021(5) -0.0004(5) S1 0.0206(13) 0.0128(14) 0.0154(13) 0.0011(11) 0.0021(10) 0.0006(11) O1 0.029(5) 0.016(5) 0.029(4) 0.002(3) -0.006(3) -0.001(4) F1 0.032(4) 0.033(4) 0.019(3) -0.002(3) -0.003(3) -0.011(3) F2 0.025(3) 0.032(4) 0.016(3) -0.006(3) -0.005(3) 0.001(3) F3 0.030(4) 0.031(4) 0.036(4) -0.002(3) 0.002(3) -0.010(3) F4 0.037(4) 0.035(4) 0.028(4) 0.011(3) 0.009(3) -0.012(4) C3 0.010(5) 0.025(7) 0.026(6) -0.008(5) 0.000(4) 0.003(5) C2 0.015(5) 0.023(7) 0.015(5) -0.007(5) 0.002(4) 0.003(5) C1 0.027(6) 0.023(7) 0.010(5) 0.001(5) -0.002(4) 0.000(5) C6 0.015(5) 0.016(7) 0.034(6) 0.004(5) 0.007(5) 0.004(5) C4 0.016(5) 0.028(7) 0.018(5) -0.002(5) 0.001(5) 0.002(5) C5 0.021(6) 0.019(7) 0.031(7) -0.005(5) 0.003(5) -0.007(5) C7 0.024(7) 0.021(7) 0.028(7) 0.007(5) -0.002(5) -0.005(5) C8 0.022(6) 0.024(7) 0.026(6) 0.006(5) -0.008(4) 0.001(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.840(10) . ? Br2 C3 1.873(12) . ? S1 O1 1.520(9) . ? S1 C8 1.807(10) . ? S1 C7 1.816(11) . ? F1 C2 1.356(13) . ? F2 C4 1.367(13) . ? F3 C5 1.339(14) . ? F4 C6 1.326(13) . ? C3 C4 1.364(16) . ? C3 C2 1.439(15) . ? C2 C1 1.369(16) . ? C1 C6 1.391(16) . ? C6 C5 1.426(15) . ? C4 C5 1.379(17) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 O1 S1 C8 105.8(5) . . ? O1 S1 C7 106.5(5) . . ? C8 S1 C7 95.3(5) . . ? C4 C3 C2 117.2(11) . . ? C4 C3 Br2 121.3(8) . . ? C2 C3 Br2 121.5(8) . . ? F1 C2 C1 119.0(9) . . ? F1 C2 C3 117.6(10) . . ? C1 C2 C3 123.4(10) . . ? C2 C1 C6 117.4(10) . . ? C2 C1 Br1 122.2(9) . . ? C6 C1 Br1 120.3(9) . . ? F4 C6 C1 122.0(10) . . ? F4 C6 C5 117.4(10) . . ? C1 C6 C5 120.6(10) . . ? C3 C4 F2 119.9(10) . . ? C3 C4 C5 121.7(11) . . ? F2 C4 C5 118.4(10) . . ? F3 C5 C4 120.3(10) . . ? F3 C5 C6 120.0(10) . . ? C4 C5 C6 119.7(10) . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C4 C3 C2 F1 179.1(10) . . . . ? Br2 C3 C2 F1 -2.2(14) . . . . ? C4 C3 C2 C1 0.9(16) . . . . ? Br2 C3 C2 C1 179.6(9) . . . . ? F1 C2 C1 C6 179.8(10) . . . . ? C3 C2 C1 C6 -2.0(17) . . . . ? F1 C2 C1 Br1 1.6(15) . . . . ? C3 C2 C1 Br1 179.8(9) . . . . ? C2 C1 C6 F4 -179.6(10) . . . . ? Br1 C1 C6 F4 -1.4(15) . . . . ? C2 C1 C6 C5 1.4(16) . . . . ? Br1 C1 C6 C5 179.7(8) . . . . ? C2 C3 C4 F2 178.9(10) . . . . ? Br2 C3 C4 F2 0.2(15) . . . . ? C2 C3 C4 C5 0.9(17) . . . . ? Br2 C3 C4 C5 -177.8(9) . . . . ? C3 C4 C5 F3 179.6(10) . . . . ? F2 C4 C5 F3 1.6(17) . . . . ? C3 C4 C5 C6 -1.4(17) . . . . ? F2 C4 C5 C6 -179.4(10) . . . . ? F4 C6 C5 F3 0.2(16) . . . . ? C1 C6 C5 F3 179.2(10) . . . . ? F4 C6 C5 C4 -178.8(10) . . . . ? C1 C6 C5 C4 0.2(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.774 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.165 #=============================================================================== data_DBTFB-DMF _database_code_depnum_ccdc_archive 'CCDC 849569' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibromotetrafluorobenzene Dimethyl formamide ; _chemical_name_common 'Dibromotetrafluorobenzene Dimethyl formamide' _chemical_melting_point ? _chemical_formula_moiety '2(C6 Br2 F4), C3 H7 N O' _chemical_formula_sum 'C15 H7 Br4 F8 N O' _chemical_formula_weight 688.86 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 56.546(6) _cell_length_b 8.1861(8) _cell_length_c 8.6095(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3985.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 143 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description CYCLINDER _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 8.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1934 _exptl_absorpt_correction_T_max 0.1934 _exptl_absorpt_process_details SADABS _exptl_special_details ; Crystallization Procedure A 0.3 mm Lindemann capillary of around 3 cm length was filled with the 1:1 mixture. The capillary was then sealed by melting at both ends, then mounted in the diffractometer equipped with a Bruker KRIOFLEX low temperature device and an Optical Heating and Crystallization Device (OHCD) for the in situ cryocrystallization. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16204 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -69 _diffrn_reflns_limit_h_max 69 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1886 _reflns_number_gt 1581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0463P)^2^+16.3248P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(2) _refine_ls_number_reflns 1886 _refine_ls_number_parameters 133 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.176 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.714480(14) 0.67237(12) 0.19090(9) 0.0455(2) Uani 1 1 d . . . Br2 Br 0.650621(15) 0.26033(9) -0.13515(12) 0.0444(2) Uani 1 1 d . . . F1 F 0.69110(8) 0.3588(5) 0.0779(5) 0.0431(12) Uani 1 1 d . . . F2 F 0.68818(8) 0.9275(5) 0.0031(5) 0.0424(11) Uani 1 1 d . . . F3 F 0.65319(7) 0.8878(5) -0.2063(5) 0.0382(11) Uani 1 1 d . . . F4 F 0.63626(7) 0.5883(5) -0.2683(5) 0.0398(11) Uani 1 1 d . . . C1 C 0.69052(12) 0.6413(10) 0.0436(8) 0.0324(17) Uani 1 1 d . . . C2 C 0.68179(13) 0.4891(9) 0.0076(9) 0.0310(16) Uani 1 1 d . . . C3 C 0.66331(13) 0.4671(8) -0.0945(8) 0.0311(17) Uani 1 1 d . . . C4 C 0.65400(12) 0.6047(9) -0.1674(8) 0.0285(17) Uani 1 1 d . . . C5 C 0.66256(12) 0.7569(9) -0.1362(10) 0.0296(14) Uani 1 1 d . . . C6 C 0.68069(12) 0.7753(8) -0.0304(8) 0.0306(18) Uani 1 1 d . . . O1 O 0.7512(3) 0.7247(16) 0.4084(10) 0.0374(14) Uani 0.50 1 d PU A -1 N1 N 0.7512(4) 0.758(3) 0.6728(11) 0.0374(14) Uani 0.50 1 d PDU A -1 C7 C 0.7432(3) 0.6970(19) 0.5408(19) 0.0374(14) Uani 0.50 1 d PDU A -1 H7 H 0.7304 0.6262 0.5472 0.045 Uiso 0.50 1 calc PR A -1 C8 C 0.7681(2) 0.8915(18) 0.6744(19) 0.0374(14) Uani 0.50 1 d PDU A -1 H8A H 0.7619 0.9813 0.6150 0.056 Uiso 0.25 1 calc PR A -1 H8B H 0.7827 0.8555 0.6296 0.056 Uiso 0.25 1 calc PR A -1 H8C H 0.7707 0.9260 0.7795 0.056 Uiso 0.25 1 calc PR A -1 H8D H 0.7817 0.8606 0.7344 0.056 Uiso 0.25 1 calc PR A -1 H8E H 0.7609 0.9864 0.7198 0.056 Uiso 0.25 1 calc PR A -1 H8F H 0.7729 0.9159 0.5699 0.056 Uiso 0.25 1 calc PR A -1 C9 C 0.7436(3) 0.699(2) 0.8225(16) 0.0374(14) Uani 0.50 1 d PDU A -1 H9A H 0.7277 0.6581 0.8147 0.056 Uiso 0.25 1 calc PR A -1 H9B H 0.7441 0.7861 0.8967 0.056 Uiso 0.25 1 calc PR A -1 H9C H 0.7539 0.6122 0.8555 0.056 Uiso 0.25 1 calc PR A -1 H9D H 0.7561 0.7128 0.8966 0.056 Uiso 0.25 1 calc PR A -1 H9E H 0.7397 0.5848 0.8146 0.056 Uiso 0.25 1 calc PR A -1 H9F H 0.7299 0.7587 0.8557 0.056 Uiso 0.25 1 calc PR A -1 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 0.0320(4) 0.0707(6) 0.0336(4) 0.0082(4) -0.0058(4) 0.0030(4) Br2 0.0550(5) 0.0272(3) 0.0509(5) 0.0001(4) 0.0128(4) -0.0023(4) F1 0.044(3) 0.041(2) 0.044(3) 0.018(2) 0.003(2) 0.017(2) F2 0.040(2) 0.037(2) 0.049(3) -0.003(2) -0.004(2) -0.005(2) F3 0.041(2) 0.033(2) 0.040(3) 0.0156(19) -0.003(2) 0.006(2) F4 0.043(2) 0.040(2) 0.037(3) 0.0046(19) -0.010(2) -0.006(2) C1 0.028(4) 0.048(5) 0.022(4) 0.005(3) 0.001(3) -0.002(3) C2 0.027(3) 0.033(4) 0.033(4) 0.008(3) 0.008(3) 0.010(3) C3 0.035(4) 0.026(3) 0.032(5) 0.004(3) 0.010(3) 0.002(3) C4 0.026(4) 0.038(4) 0.022(4) 0.005(3) 0.000(3) -0.002(3) C5 0.032(3) 0.029(3) 0.028(4) 0.011(3) 0.002(4) 0.007(3) C6 0.026(4) 0.035(4) 0.031(5) -0.002(3) 0.003(3) 0.002(3) O1 0.036(3) 0.045(4) 0.031(3) 0.004(3) -0.005(3) 0.001(2) N1 0.036(3) 0.045(4) 0.031(3) 0.004(3) -0.005(3) 0.001(2) C7 0.036(3) 0.045(4) 0.031(3) 0.004(3) -0.005(3) 0.001(2) C8 0.036(3) 0.045(4) 0.031(3) 0.004(3) -0.005(3) 0.001(2) C9 0.036(3) 0.045(4) 0.031(3) 0.004(3) -0.005(3) 0.001(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.873(7) . ? Br2 C3 1.871(7) . ? F1 C2 1.335(8) . ? F2 C6 1.347(8) . ? F3 C5 1.339(8) . ? F4 C4 1.334(8) . ? C1 C2 1.375(11) . ? C1 C6 1.385(10) . ? C2 C3 1.377(11) . ? C3 C4 1.393(10) . ? C4 C5 1.363(10) . ? C5 C6 1.380(10) . ? O1 C7 1.246(19) . ? N1 C7 1.32(2) . ? N1 C9 1.443(13) . ? N1 C8 1.451(14) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 H8D 0.9600 . ? C8 H8E 0.9600 . ? C8 H8F 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 H9D 0.9600 . ? C9 H9E 0.9600 . ? C9 H9F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.0(6) . . ? C2 C1 Br1 122.4(6) . . ? C6 C1 Br1 119.6(6) . . ? F1 C2 C1 118.7(7) . . ? F1 C2 C3 118.9(7) . . ? C1 C2 C3 122.3(7) . . ? C2 C3 C4 117.9(7) . . ? C2 C3 Br2 121.9(5) . . ? C4 C3 Br2 120.1(6) . . ? F4 C4 C5 119.1(6) . . ? F4 C4 C3 119.8(6) . . ? C5 C4 C3 121.1(7) . . ? F3 C5 C4 120.1(6) . . ? F3 C5 C6 120.3(7) . . ? C4 C5 C6 119.6(6) . . ? F2 C6 C5 118.4(6) . . ? F2 C6 C1 120.5(6) . . ? C5 C6 C1 121.0(7) . . ? C7 N1 C9 122.6(11) . . ? C7 N1 C8 121.2(9) . . ? C9 N1 C8 116.2(13) . . ? O1 C7 N1 126.4(14) . . ? O1 C7 H7 116.8 . . ? N1 C7 H7 116.8 . . ? 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 C6 C1 C2 F1 180.0(6) . . . . ? Br1 C1 C2 F1 -1.5(10) . . . . ? C6 C1 C2 C3 -2.2(11) . . . . ? Br1 C1 C2 C3 176.4(6) . . . . ? F1 C2 C3 C4 -179.5(6) . . . . ? C1 C2 C3 C4 2.6(11) . . . . ? F1 C2 C3 Br2 0.9(10) . . . . ? C1 C2 C3 Br2 -177.0(6) . . . . ? C2 C3 C4 F4 179.3(6) . . . . ? Br2 C3 C4 F4 -1.1(9) . . . . ? C2 C3 C4 C5 -1.4(11) . . . . ? Br2 C3 C4 C5 178.2(6) . . . . ? F4 C4 C5 F3 0.1(11) . . . . ? C3 C4 C5 F3 -179.3(6) . . . . ? F4 C4 C5 C6 179.1(6) . . . . ? C3 C4 C5 C6 -0.2(11) . . . . ? F3 C5 C6 F2 1.7(10) . . . . ? C4 C5 C6 F2 -177.3(7) . . . . ? F3 C5 C6 C1 179.8(7) . . . . ? C4 C5 C6 C1 0.7(11) . . . . ? C2 C1 C6 F2 178.5(7) . . . . ? Br1 C1 C6 F2 -0.2(9) . . . . ? C2 C1 C6 C5 0.5(11) . . . . ? Br1 C1 C6 C5 -178.2(6) . . . . ? C9 N1 C7 O1 -169(2) . . . . ? C8 N1 C7 O1 11(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.783 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.184 #=========END