# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Ramamurthy, V.' 'Captain, Burjor' 'Mondal, Barnali' _publ_contact_author_name 'Ramamurthy, V.' _publ_contact_author_email murthy1@miami.edu _publ_section_title ; Templated photodimerization of protonated azastilbenes in solid State ; data_1-Stilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813287' #TrackingRef '1-Stilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 Cl N O3' _chemical_formula_weight 271.73 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' Cl Cl 0.1484 0.1585 '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 7.0919(5) _cell_length_b 10.1566(7) _cell_length_c 10.9322(7) _cell_angle_alpha 69.8118(9) _cell_angle_beta 82.7066(10) _cell_angle_gamma 79.1375(10) _cell_volume 724.18(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3345 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 28.78 _exptl_crystal_description Bar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6619 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5884 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2549 _reflns_number_gt 2227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0952P)^2^+0.1822P] 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 2549 _refine_ls_number_parameters 187 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 Cl1 Cl 0.35740(9) 0.80599(6) 0.66906(6) 0.0782(3) Uani 1 1 d . . . N1 N 0.8691(3) 0.3026(3) -0.2608(3) 0.0917(8) Uani 1 1 d . . . H1N H 0.8953 0.2578 -0.3163 0.110 Uiso 1 1 calc R . . C1 C 0.8586(5) 0.4411(4) -0.3021(3) 0.0953(9) Uani 1 1 d . . . H1 H 0.8811 0.4892 -0.3907 0.114 Uiso 1 1 calc R . . C2 C 0.8164(4) 0.5140(3) -0.2191(3) 0.0839(7) Uani 1 1 d . . . H2 H 0.8079 0.6123 -0.2505 0.101 Uiso 1 1 calc R . . C3 C 0.7849(3) 0.4451(3) -0.0867(2) 0.0670(6) Uani 1 1 d . . . C4 C 0.7973(4) 0.2998(3) -0.0471(3) 0.0815(7) Uani 1 1 d . . . H4 H 0.7761 0.2486 0.0408 0.098 Uiso 1 1 calc R . . C5 C 0.8405(4) 0.2310(3) -0.1361(4) 0.0926(9) Uani 1 1 d . . . H5 H 0.8498 0.1327 -0.1088 0.111 Uiso 1 1 calc R . . C6 C 0.7369(5) 0.4972(5) 0.0279(5) 0.0656(8) Uani 0.70 1 d P . . H6 H 0.7148 0.4317 0.1100 0.079 Uiso 0.70 1 calc PR . . C7 C 0.7250(5) 0.6292(4) 0.0176(5) 0.0671(8) Uani 0.70 1 d P . . H7 H 0.7467 0.6955 -0.0642 0.081 Uiso 0.70 1 calc PR . . C8 C 0.6773(3) 0.6778(3) 0.1336(3) 0.0772(7) Uani 1 1 d . . . C9 C 0.6680(4) 0.8239(3) 0.0951(3) 0.0870(8) Uani 1 1 d . . . H9 H 0.6921 0.8750 0.0075 0.104 Uiso 1 1 calc R . . C10 C 0.6243(4) 0.8928(3) 0.1832(4) 0.0924(8) Uani 1 1 d . . . H10 H 0.6182 0.9909 0.1547 0.111 Uiso 1 1 calc R . . C11 C 0.5892(4) 0.8232(3) 0.3117(3) 0.0902(8) Uani 1 1 d . . . H11 H 0.5597 0.8723 0.3711 0.108 Uiso 1 1 calc R . . C12 C 0.5981(4) 0.6794(4) 0.3523(3) 0.0937(8) Uani 1 1 d . . . H12 H 0.5741 0.6300 0.4403 0.112 Uiso 1 1 calc R . . C13 C 0.6422(4) 0.6066(3) 0.2642(3) 0.0866(8) Uani 1 1 d . . . H13 H 0.6482 0.5084 0.2934 0.104 Uiso 1 1 calc R . . C6B C 0.7481(10) 0.5753(10) -0.0416(8) 0.0543(15) Uani 0.30 1 d P . . H6B H 0.7501 0.6669 -0.0998 0.065 Uiso 0.30 1 calc PR . . C7B C 0.7119(9) 0.5475(8) 0.0913(7) 0.0462(12) Uani 0.30 1 d P . . H7B H 0.7089 0.4563 0.1500 0.055 Uiso 0.30 1 calc PR . . O1 O 0.9365(3) 0.26584(19) 0.49491(18) 0.0836(5) Uani 1 1 d D . . O2 O 0.7536(3) 0.91640(19) 0.57405(18) 0.0795(5) Uani 1 1 d D . . O3 O 0.9446(3) 0.9608(3) 0.7700(2) 0.1102(7) Uani 1 1 d D . . H1S H 1.0353 0.2106 0.4802 0.103(10) Uiso 1 1 d RD . . H2S H 0.8470 0.2543 0.4556 0.078(8) Uiso 1 1 d RD . . H3S H 0.7298 0.9959 0.5123 0.117(12) Uiso 1 1 d RD . . H4S H 0.6407 0.8989 0.6062 0.109(11) Uiso 1 1 d RD . . H5S H 1.0553 0.9209 0.7517 0.115(12) Uiso 1 1 d RD . . H6S H 0.8693 0.9577 0.7174 0.106(11) Uiso 1 1 d RD . . 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 0.0896(5) 0.0629(4) 0.0743(4) -0.0132(3) 0.0023(3) -0.0159(3) N1 0.0663(13) 0.129(2) 0.112(2) -0.0860(19) 0.0073(12) -0.0116(13) C1 0.096(2) 0.120(3) 0.0670(15) -0.0320(16) 0.0076(13) -0.0163(18) C2 0.0866(17) 0.0685(15) 0.0897(18) -0.0200(13) 0.0005(14) -0.0110(12) C3 0.0502(11) 0.0845(15) 0.0763(14) -0.0401(12) -0.0036(9) -0.0089(10) C4 0.0726(15) 0.0900(18) 0.0723(15) -0.0154(13) -0.0041(12) -0.0120(13) C5 0.0694(15) 0.0657(15) 0.143(3) -0.0367(17) -0.0037(16) -0.0080(12) C6 0.0669(19) 0.068(2) 0.063(2) -0.023(2) 0.0002(15) -0.0124(16) C7 0.0640(19) 0.065(2) 0.070(2) -0.022(2) 0.0019(16) -0.0098(16) C8 0.0544(12) 0.0956(18) 0.1021(19) -0.0607(16) -0.0070(11) -0.0057(11) C9 0.0834(17) 0.097(2) 0.0811(17) -0.0254(15) -0.0062(13) -0.0238(14) C10 0.0949(19) 0.0732(16) 0.117(2) -0.0402(16) -0.0100(17) -0.0144(14) C11 0.0857(18) 0.099(2) 0.105(2) -0.0650(19) -0.0066(15) -0.0017(15) C12 0.0908(18) 0.107(2) 0.0802(17) -0.0309(16) -0.0023(14) -0.0095(16) C13 0.0757(16) 0.0634(14) 0.120(2) -0.0305(15) -0.0152(15) -0.0028(12) C6B 0.071(4) 0.043(4) 0.045(4) -0.014(4) 0.005(3) -0.008(3) C7B 0.057(3) 0.039(3) 0.043(3) -0.015(4) 0.001(3) -0.008(3) O1 0.0979(13) 0.0803(11) 0.0791(11) -0.0398(9) 0.0000(9) -0.0077(10) O2 0.0761(11) 0.0727(11) 0.0832(11) -0.0196(9) -0.0076(9) -0.0065(8) O3 0.1070(16) 0.143(2) 0.0929(14) -0.0664(14) -0.0122(12) 0.0074(14) _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 N1 C1 1.311(4) . ? N1 C5 1.315(4) . ? C1 C2 1.331(4) . ? C2 C3 1.383(4) . ? C3 C4 1.376(4) . ? C3 C6 1.499(5) . ? C3 C6B 1.532(9) . ? C4 C5 1.357(4) . ? C6 C7 1.293(6) . ? C7 C8 1.492(5) . ? C8 C13 1.374(4) . ? C8 C9 1.386(4) . ? C8 C7B 1.516(8) . ? C9 C10 1.350(4) . ? C10 C11 1.352(5) . ? C11 C12 1.363(4) . ? C12 C13 1.379(4) . ? C6B C7B 1.380(10) . ? 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 N1 C5 121.2(2) . . ? N1 C1 C2 121.0(3) . . ? C1 C2 C3 120.7(3) . . ? C4 C3 C2 116.6(2) . . ? C4 C3 C6 110.7(3) . . ? C2 C3 C6 132.7(3) . . ? C4 C3 C6B 145.1(4) . . ? C2 C3 C6B 98.3(4) . . ? C6 C3 C6B 34.4(3) . . ? C5 C4 C3 120.1(3) . . ? N1 C5 C4 120.4(3) . . ? C7 C6 C3 122.9(5) . . ? C6 C7 C8 121.7(5) . . ? C13 C8 C9 117.6(2) . . ? C13 C8 C7 132.5(3) . . ? C9 C8 C7 110.0(3) . . ? C13 C8 C7B 95.8(4) . . ? C9 C8 C7B 146.6(4) . . ? C7 C8 C7B 36.6(3) . . ? C10 C9 C8 120.8(3) . . ? C9 C10 C11 121.8(3) . . ? C10 C11 C12 118.6(3) . . ? C11 C12 C13 120.7(3) . . ? C8 C13 C12 120.5(3) . . ? C7B C6B C3 115.5(8) . . ? C6B C7B C8 114.5(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.330 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.073 # Attachment '10-34DiMethoxyStilbazole-Monomer.cif' data_10-34DiMethoxyStilbazole-Monomer _database_code_depnum_ccdc_archive 'CCDC 813288' #TrackingRef '10-34DiMethoxyStilbazole-Monomer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O2' _chemical_formula_weight 241.28 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 8.7901(5) _cell_length_b 7.8000(4) _cell_length_c 19.3873(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.9620(10) _cell_angle_gamma 90.00 _cell_volume 1319.45(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5428 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 32.64 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11654 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.50 _reflns_number_total 2738 _reflns_number_gt 2265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0597P)^2^+0.2528P] 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 SHELXL _refine_ls_extinction_coef 0.027(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2738 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O1 O -0.17441(11) 1.15695(14) 0.02972(5) 0.0672(3) Uani 1 1 d . . . O2 O -0.36872(10) 0.93024(13) 0.05982(5) 0.0591(3) Uani 1 1 d . . . N1 N 0.72193(14) 0.90963(19) 0.38337(7) 0.0705(4) Uani 1 1 d . . . C1 C 0.68744(17) 0.9879(2) 0.32273(9) 0.0699(4) Uani 1 1 d . . . H1 H 0.7649 1.0482 0.3047 0.084 Uiso 1 1 calc R . . C2 C 0.54427(17) 0.9857(2) 0.28464(8) 0.0636(4) Uani 1 1 d . . . H2 H 0.5278 1.0427 0.2423 0.076 Uiso 1 1 calc R . . C3 C 0.42508(15) 0.89833(17) 0.30977(7) 0.0533(3) Uani 1 1 d . . . C4 C 0.46135(18) 0.8175(2) 0.37308(8) 0.0673(4) Uani 1 1 d . . . H4 H 0.3865 0.7572 0.3930 0.081 Uiso 1 1 calc R . . C5 C 0.60782(19) 0.8263(2) 0.40646(8) 0.0747(5) Uani 1 1 d . . . H5 H 0.6283 0.7691 0.4486 0.090 Uiso 1 1 calc R . . C6 C 0.26927(16) 0.88417(19) 0.27330(8) 0.0586(4) Uani 1 1 d . . . H6 H 0.2017 0.8126 0.2930 0.070 Uiso 1 1 calc R . . C7 C 0.21584(15) 0.96308(19) 0.21528(7) 0.0575(4) Uani 1 1 d . . . H7 H 0.2830 1.0371 0.1966 0.069 Uiso 1 1 calc R . . C8 C 0.06138(15) 0.94685(17) 0.17677(7) 0.0535(3) Uani 1 1 d . . . C9 C 0.01925(14) 1.05962(17) 0.12186(7) 0.0527(3) Uani 1 1 d . . . H9 H 0.0889 1.1419 0.1107 0.063 Uiso 1 1 calc R . . C10 C -0.12412(14) 1.05134(17) 0.08367(7) 0.0499(3) Uani 1 1 d . . . C11 C -0.22997(14) 0.92762(17) 0.10019(7) 0.0498(3) Uani 1 1 d . . . C12 C -0.18872(16) 0.8155(2) 0.15404(8) 0.0622(4) Uani 1 1 d . . . H12 H -0.2581 0.7330 0.1652 0.075 Uiso 1 1 calc R . . C13 C -0.04404(17) 0.8248(2) 0.19183(8) 0.0642(4) Uani 1 1 d . . . H13 H -0.0176 0.7476 0.2279 0.077 Uiso 1 1 calc R . . C14 C -0.07519(19) 1.2914(2) 0.01302(10) 0.0807(5) Uani 1 1 d . . . H14A H -0.0530 1.3656 0.0525 0.121 Uiso 1 1 calc R . . H14B H -0.1243 1.3560 -0.0256 0.121 Uiso 1 1 calc R . . H14C H 0.0185 1.2431 0.0009 0.121 Uiso 1 1 calc R . . C15 C -0.48647(17) 0.8220(2) 0.07946(9) 0.0733(5) Uani 1 1 d . . . H15A H -0.4569 0.7042 0.0755 0.110 Uiso 1 1 calc R . . H15B H -0.5798 0.8428 0.0495 0.110 Uiso 1 1 calc R . . H15C H -0.5021 0.8458 0.1267 0.110 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 O1 0.0523(5) 0.0722(7) 0.0724(6) 0.0240(5) -0.0112(4) -0.0164(5) O2 0.0463(5) 0.0649(6) 0.0627(6) 0.0084(4) -0.0076(4) -0.0143(4) N1 0.0554(7) 0.0784(9) 0.0730(8) 0.0049(7) -0.0112(6) 0.0099(6) C1 0.0531(8) 0.0732(10) 0.0809(10) 0.0113(8) -0.0019(7) -0.0040(7) C2 0.0617(8) 0.0650(9) 0.0610(8) 0.0132(7) -0.0057(6) 0.0021(7) C3 0.0506(7) 0.0474(7) 0.0597(7) -0.0042(6) -0.0032(6) 0.0051(5) C4 0.0618(9) 0.0707(9) 0.0682(9) 0.0133(7) 0.0026(7) -0.0011(7) C5 0.0721(10) 0.0848(11) 0.0638(9) 0.0176(8) -0.0056(7) 0.0108(9) C6 0.0530(7) 0.0564(8) 0.0644(8) 0.0014(6) -0.0012(6) -0.0025(6) C7 0.0488(7) 0.0566(8) 0.0651(8) 0.0014(6) -0.0016(6) 0.0012(6) C8 0.0467(7) 0.0538(7) 0.0580(8) -0.0019(6) -0.0016(6) 0.0023(6) C9 0.0431(6) 0.0522(7) 0.0614(8) 0.0006(6) 0.0008(5) -0.0049(5) C10 0.0451(6) 0.0507(7) 0.0526(7) 0.0017(5) -0.0002(5) -0.0030(5) C11 0.0427(6) 0.0522(7) 0.0527(7) -0.0020(5) -0.0013(5) -0.0039(5) C12 0.0544(8) 0.0613(8) 0.0688(9) 0.0131(7) -0.0004(6) -0.0117(6) C13 0.0586(8) 0.0653(9) 0.0655(9) 0.0173(7) -0.0060(6) -0.0010(7) C14 0.0695(10) 0.0765(11) 0.0914(12) 0.0323(9) -0.0090(8) -0.0202(8) C15 0.0526(8) 0.0887(11) 0.0754(10) 0.0138(9) -0.0049(7) -0.0247(8) _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 O1 C10 1.3623(16) . ? O1 C14 1.4259(17) . ? O2 C11 1.3671(15) . ? O2 C15 1.4231(17) . ? N1 C5 1.318(2) . ? N1 C1 1.327(2) . ? C1 C2 1.380(2) . ? C2 C3 1.387(2) . ? C3 C4 1.3823(19) . ? C3 C6 1.4673(18) . ? C4 C5 1.371(2) . ? C6 C7 1.318(2) . ? C7 C8 1.4734(18) . ? C8 C13 1.384(2) . ? C8 C9 1.3960(19) . ? C9 C10 1.3835(17) . ? C10 C11 1.4042(18) . ? C11 C12 1.3762(19) . ? C12 C13 1.3905(19) . ? 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 C10 O1 C14 117.94(11) . . ? C11 O2 C15 117.73(10) . . ? C5 N1 C1 115.22(13) . . ? N1 C1 C2 124.35(15) . . ? C1 C2 C3 119.79(14) . . ? C4 C3 C2 115.68(12) . . ? C4 C3 C6 119.66(13) . . ? C2 C3 C6 124.65(13) . . ? C5 C4 C3 119.92(15) . . ? N1 C5 C4 125.04(14) . . ? C7 C6 C3 126.25(14) . . ? C6 C7 C8 127.12(14) . . ? C13 C8 C9 118.14(12) . . ? C13 C8 C7 123.48(12) . . ? C9 C8 C7 118.38(12) . . ? C10 C9 C8 121.26(12) . . ? O1 C10 C9 124.91(12) . . ? O1 C10 C11 115.36(11) . . ? C9 C10 C11 119.72(12) . . ? O2 C11 C12 125.34(12) . . ? O2 C11 C10 115.40(11) . . ? C12 C11 C10 119.25(12) . . ? C11 C12 C13 120.44(13) . . ? C8 C13 C12 121.18(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.215 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.036 # Attachment '11-4CF3Stilbazole-HCl-Salt.cif' data_11-4CF3Stilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813289' #TrackingRef '11-4CF3Stilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Cl F3 N O3' _chemical_formula_weight 339.74 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' Cl Cl 0.1484 0.1585 '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 7.4124(3) _cell_length_b 9.5475(4) _cell_length_c 12.2010(5) _cell_angle_alpha 80.0619(6) _cell_angle_beta 82.0762(6) _cell_angle_gamma 75.3538(6) _cell_volume 818.84(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7128 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 32.42 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6418 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9579 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3203 _reflns_number_gt 2960 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0716P)^2^+0.2750P] 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 SHELXL _refine_ls_extinction_coef 0.091(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 234 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.048 _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 N1 N 0.8041(2) 1.22662(19) -0.40287(13) 0.0584(4) Uani 1 1 d . A 4 H1A H 0.8119 1.2598 -0.4731 0.070 Uiso 1 1 calc R A 4 O1 O 0.8085(3) 0.3957(2) 0.03872(13) 0.0811(5) Uani 1 1 d D B 4 O2 O 0.5601(2) 0.3768(2) 0.23177(14) 0.0862(5) Uani 1 1 d D C 4 O3 O 0.8341(2) 0.2788(2) 0.37337(12) 0.0795(5) Uani 1 1 d D D 4 C1 C 0.8019(3) 1.0865(2) -0.36973(17) 0.0625(5) Uani 1 1 d . A 4 H1 H 0.8105 1.0255 -0.4229 0.075 Uiso 1 1 calc R A 4 C2 C 0.7873(3) 1.0309(2) -0.25818(17) 0.0603(5) Uani 1 1 d . A 4 H2 H 0.7850 0.9332 -0.2359 0.072 Uiso 1 1 calc R A 4 C3 C 0.7758(2) 1.1222(2) -0.17852(15) 0.0511(4) Uani 1 1 d . A 4 C4 C 0.7801(3) 1.2659(2) -0.21759(17) 0.0615(5) Uani 1 1 d . A 4 H4 H 0.7733 1.3298 -0.1668 0.074 Uiso 1 1 calc R A 4 C5 C 0.7942(3) 1.3155(2) -0.32876(18) 0.0637(5) Uani 1 1 d . A 4 H5 H 0.7970 1.4128 -0.3533 0.076 Uiso 1 1 calc R A 4 C6 C 0.7600(3) 1.0768(2) -0.05683(16) 0.0583(5) Uani 1 1 d . A 4 H6 H 0.7565 1.1464 -0.0114 0.070 Uiso 1 1 calc R A 4 C7 C 0.7503(3) 0.9450(2) -0.00792(15) 0.0555(4) Uani 1 1 d . A 4 H7 H 0.7534 0.8760 -0.0539 0.067 Uiso 1 1 calc R A 4 C8 C 0.7347(2) 0.8968(2) 0.11413(14) 0.0509(4) Uani 1 1 d . A 4 C9 C 0.7302(3) 0.7535(2) 0.15125(16) 0.0610(5) Uani 1 1 d . A 4 H9 H 0.7377 0.6911 0.0993 0.073 Uiso 1 1 calc R A 4 C10 C 0.7149(3) 0.6998(2) 0.26366(17) 0.0608(5) Uani 1 1 d . A 4 H10 H 0.7116 0.6023 0.2868 0.073 Uiso 1 1 calc R A 4 C11 C 0.7044(2) 0.7909(2) 0.34149(14) 0.0498(4) Uani 1 1 d . A 4 C12 C 0.7085(3) 0.9349(2) 0.30719(16) 0.0589(5) Uani 1 1 d . A 4 H12 H 0.7012 0.9966 0.3597 0.071 Uiso 1 1 calc R A 4 C13 C 0.7236(3) 0.9883(2) 0.19389(16) 0.0601(5) Uani 1 1 d . A 4 H13 H 0.7263 1.0859 0.1708 0.072 Uiso 1 1 calc R A 4 C14 C 0.6900(3) 0.7321(3) 0.46374(17) 0.0683(6) Uani 1 1 d . A 4 Cl1 Cl 0.14767(7) 0.37054(5) 0.18468(4) 0.0635(2) Uani 1 1 d . E 4 H1S H 0.8050 0.4694 -0.0141 0.115(11) Uiso 1 1 d RD E 4 H2S H 0.9104 0.3890 0.0660 0.112(11) Uiso 1 1 d RD E 4 H3S H 0.6063 0.3860 0.1637 0.098(9) Uiso 1 1 d RD E 4 H4S H 0.4654 0.3632 0.2140 0.091(9) Uiso 1 1 d RD E 4 H5S H 0.9204 0.3100 0.3342 0.089(9) Uiso 1 1 d RD E 4 H6S H 0.7478 0.2982 0.3301 0.099(9) Uiso 1 1 d RD E 4 F1 F 0.5872(7) 0.6316(6) 0.4890(3) 0.0952(10) Uani 0.70 1 d P A 4 F2 F 0.8479(4) 0.6567(9) 0.4999(3) 0.120(2) Uani 0.70 1 d P A 4 F3 F 0.6081(15) 0.8285(4) 0.5286(3) 0.162(3) Uani 0.70 1 d P A 4 F4 F 0.7979(17) 0.7910(17) 0.5154(5) 0.102(2) Uani 0.30 1 d P F 2 F5 F 0.762(5) 0.6033(10) 0.4855(8) 0.252(11) Uani 0.30 1 d P G 2 F6 F 0.5408(8) 0.775(3) 0.5128(6) 0.166(8) Uani 0.30 1 d P H 2 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 N1 0.0557(9) 0.0751(11) 0.0403(8) 0.0114(7) -0.0069(6) -0.0197(8) O1 0.0944(12) 0.1004(13) 0.0606(9) -0.0014(9) -0.0100(8) -0.0504(10) O2 0.0698(10) 0.1272(15) 0.0643(10) -0.0034(9) -0.0128(8) -0.0318(10) O3 0.0730(10) 0.1210(14) 0.0431(7) 0.0073(8) -0.0061(7) -0.0330(9) C1 0.0703(12) 0.0703(12) 0.0506(10) -0.0093(9) -0.0078(9) -0.0218(10) C2 0.0690(12) 0.0516(10) 0.0589(11) 0.0055(8) -0.0078(9) -0.0197(9) C3 0.0470(9) 0.0585(10) 0.0446(9) 0.0038(7) -0.0071(7) -0.0127(8) C4 0.0749(13) 0.0584(11) 0.0513(10) -0.0042(8) -0.0056(9) -0.0186(9) C5 0.0756(13) 0.0547(11) 0.0577(11) 0.0076(9) -0.0055(9) -0.0206(9) C6 0.0651(11) 0.0588(11) 0.0512(10) -0.0022(8) -0.0086(8) -0.0170(9) C7 0.0601(11) 0.0585(10) 0.0472(10) -0.0033(8) -0.0067(8) -0.0147(8) C8 0.0474(9) 0.0611(10) 0.0405(9) -0.0005(7) -0.0051(7) -0.0103(8) C9 0.0778(13) 0.0582(11) 0.0473(10) -0.0089(8) -0.0077(9) -0.0151(9) C10 0.0766(13) 0.0486(10) 0.0543(11) 0.0012(8) -0.0082(9) -0.0144(9) C11 0.0493(9) 0.0569(10) 0.0396(9) 0.0018(7) -0.0060(7) -0.0108(7) C12 0.0746(13) 0.0586(11) 0.0452(10) -0.0088(8) -0.0050(8) -0.0184(9) C13 0.0753(13) 0.0493(10) 0.0530(10) 0.0055(8) -0.0047(9) -0.0191(9) C14 0.0702(13) 0.0840(15) 0.0463(10) 0.0082(10) -0.0081(9) -0.0207(11) Cl1 0.0695(3) 0.0628(3) 0.0605(3) 0.0009(2) -0.0090(2) -0.0249(2) F1 0.0960(18) 0.123(3) 0.0662(14) 0.0331(18) -0.0088(15) -0.055(2) F2 0.0622(14) 0.204(6) 0.0707(19) 0.060(3) -0.0231(12) -0.034(2) F3 0.317(10) 0.0945(19) 0.0470(15) -0.0133(13) 0.028(3) -0.019(4) F4 0.112(6) 0.169(8) 0.039(2) 0.011(4) -0.029(3) -0.062(5) F5 0.56(4) 0.054(4) 0.081(5) 0.031(3) -0.051(15) 0.029(11) F6 0.043(3) 0.36(3) 0.044(4) 0.023(8) 0.014(2) -0.009(6) _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 N1 C5 1.326(3) . ? N1 C1 1.333(3) . ? C1 C2 1.373(3) . ? C2 C3 1.394(3) . ? C3 C4 1.380(3) . ? C3 C6 1.470(3) . ? C4 C5 1.356(3) . ? C6 C7 1.311(3) . ? C7 C8 1.478(2) . ? C8 C9 1.372(3) . ? C8 C13 1.397(3) . ? C9 C10 1.379(3) . ? C10 C11 1.377(3) . ? C11 C12 1.373(3) . ? C11 C14 1.500(3) . ? C12 C13 1.388(3) . ? C14 F3 1.296(4) . ? C14 F2 1.300(4) . ? C14 F1 1.342(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 C5 N1 C1 120.73(16) . . ? N1 C1 C2 120.92(19) . . ? C1 C2 C3 119.53(18) . . ? C4 C3 C2 117.06(17) . . ? C4 C3 C6 117.87(17) . . ? C2 C3 C6 125.06(17) . . ? C5 C4 C3 121.11(19) . . ? N1 C5 C4 120.65(19) . . ? C7 C6 C3 124.54(19) . . ? C6 C7 C8 125.51(19) . . ? C9 C8 C13 118.05(16) . . ? C9 C8 C7 117.92(17) . . ? C13 C8 C7 124.03(17) . . ? C8 C9 C10 121.65(18) . . ? C11 C10 C9 119.79(18) . . ? C12 C11 C10 120.06(16) . . ? C12 C11 C14 120.14(18) . . ? C10 C11 C14 119.80(18) . . ? C11 C12 C13 119.83(18) . . ? C12 C13 C8 120.63(18) . . ? F3 C14 F2 110.1(4) . . ? F3 C14 F1 103.2(4) . . ? F2 C14 F1 100.6(3) . . ? F3 C14 C11 114.7(3) . . ? F2 C14 C11 114.1(2) . . ? F1 C14 C11 112.7(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.514 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.057 # Attachment '12-35DiChloroStilbazole-HCl-Salt.cif' data_12-35DiChloroStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813290' #TrackingRef '12-35DiChloroStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl3 N' _chemical_formula_weight 286.57 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' Cl Cl 0.1484 0.1585 '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 4.9487(3) _cell_length_b 7.8558(4) _cell_length_c 16.9993(9) _cell_angle_alpha 96.3056(8) _cell_angle_beta 91.9793(8) _cell_angle_gamma 93.8669(8) _cell_volume 654.78(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4949 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.75 _exptl_crystal_description Bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7037 _exptl_absorpt_correction_T_max 0.8769 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7071 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2306 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0500P)^2^+0.9471P] 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 SHELXL _refine_ls_extinction_coef 0.065(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2306 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1497 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Cl1 Cl 0.7952(3) 0.29628(17) 0.48818(8) 0.0981(5) Uani 1 1 d . . . Cl2 Cl 0.6420(4) -0.32914(19) 0.33006(10) 0.1282(7) Uani 1 1 d . . . Cl3 Cl 0.07115(17) 0.73142(10) 0.07489(5) 0.0583(3) Uani 1 1 d . . . N1 N -0.6491(6) 0.3139(4) 0.06488(17) 0.0611(8) Uani 1 1 d . . . H1 H -0.7744 0.3454 0.0345 0.073 Uiso 1 1 calc R . . C1 C -0.4825(8) 0.4327(5) 0.1060(2) 0.0631(9) Uani 1 1 d . . . H1A H -0.5002 0.5483 0.1013 0.076 Uiso 1 1 calc R . . C2 C -0.2846(7) 0.3850(5) 0.1553(2) 0.0602(9) Uani 1 1 d . . . H2 H -0.1665 0.4680 0.1841 0.072 Uiso 1 1 calc R . . C3 C -0.2603(7) 0.2128(5) 0.1625(2) 0.0565(9) Uani 1 1 d . . . C4 C -0.4378(8) 0.0950(5) 0.1168(2) 0.0628(9) Uani 1 1 d . . . H4 H -0.4247 -0.0219 0.1191 0.075 Uiso 1 1 calc R . . C5 C -0.6289(8) 0.1485(5) 0.0691(2) 0.0627(9) Uani 1 1 d . . . H5 H -0.7479 0.0685 0.0389 0.075 Uiso 1 1 calc R . . C6 C -0.0693(12) 0.1235(10) 0.2073(4) 0.0438(12) Uani 0.62 1 d P . . H6 H -0.0564 0.0063 0.1942 0.053 Uiso 0.62 1 calc PR . . C7 C 0.0865(12) 0.2060(8) 0.2664(4) 0.0482(12) Uani 0.62 1 d P . . H7 H 0.0714 0.3228 0.2801 0.058 Uiso 0.62 1 calc PR . . C8 C 0.2882(9) 0.1140(8) 0.3120(3) 0.0867(15) Uani 1 1 d . . . C9 C 0.4232(8) 0.2148(7) 0.3702(3) 0.0782(13) Uani 1 1 d . . . H9 H 0.3827 0.3288 0.3804 0.094 Uiso 1 1 calc R . . C10 C 0.6198(7) 0.1541(5) 0.4153(2) 0.0630(9) Uani 1 1 d . . . C11 C 0.6902(7) -0.0122(5) 0.4047(2) 0.0616(9) Uani 1 1 d . . . H11 H 0.8250 -0.0504 0.4364 0.074 Uiso 1 1 calc R . . C12 C 0.5545(9) -0.1195(6) 0.3455(2) 0.0730(11) Uani 1 1 d . . . C13 C 0.3495(9) -0.0573(9) 0.2977(2) 0.0929(18) Uani 1 1 d . . . H13 H 0.2572 -0.1302 0.2573 0.111 Uiso 1 1 calc R . . C6B C -0.032(2) 0.2181(18) 0.2291(8) 0.053(2) Uani 0.38 1 d P . . H6B H 0.0336 0.3206 0.2583 0.064 Uiso 0.38 1 calc PR . . C7B C 0.061(2) 0.0740(13) 0.2415(6) 0.054(2) Uani 0.38 1 d P . . H7B H 0.0073 -0.0332 0.2147 0.065 Uiso 0.38 1 calc PR . . 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 0.1106(10) 0.0873(9) 0.0929(9) -0.0025(6) 0.0011(7) 0.0043(7) Cl2 0.1804(17) 0.0851(9) 0.1141(12) -0.0130(8) 0.0240(11) 0.0026(10) Cl3 0.0554(5) 0.0506(5) 0.0679(6) 0.0075(4) -0.0132(4) 0.0024(4) N1 0.0429(15) 0.090(2) 0.0557(17) 0.0256(16) 0.0015(13) 0.0117(15) C1 0.065(2) 0.056(2) 0.073(2) 0.0173(18) 0.0104(19) 0.0154(17) C2 0.056(2) 0.066(2) 0.057(2) 0.0043(17) -0.0017(16) -0.0016(17) C3 0.0436(17) 0.082(2) 0.0510(19) 0.0265(17) 0.0125(14) 0.0165(16) C4 0.069(2) 0.054(2) 0.070(2) 0.0146(17) 0.0218(19) 0.0087(17) C5 0.058(2) 0.075(2) 0.054(2) 0.0059(18) 0.0065(16) -0.0081(18) C6 0.042(3) 0.044(3) 0.046(3) 0.009(3) -0.001(2) 0.007(3) C7 0.048(3) 0.049(4) 0.048(3) 0.004(3) 0.000(3) 0.007(3) C8 0.054(2) 0.141(5) 0.078(3) 0.056(3) 0.015(2) 0.024(3) C9 0.060(2) 0.113(4) 0.072(3) 0.043(3) 0.011(2) 0.023(2) C10 0.057(2) 0.079(3) 0.057(2) 0.0235(18) 0.0040(16) 0.0102(18) C11 0.059(2) 0.079(3) 0.0502(19) 0.0196(18) -0.0046(16) 0.0128(18) C12 0.079(3) 0.084(3) 0.056(2) 0.010(2) 0.007(2) -0.005(2) C13 0.060(2) 0.172(6) 0.041(2) 0.017(3) -0.0060(17) -0.037(3) C6B 0.053(6) 0.059(7) 0.045(6) 0.002(6) 0.001(5) -0.001(6) C7B 0.055(5) 0.057(6) 0.051(5) 0.005(5) 0.003(4) 0.006(5) _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 C10 1.740(4) . ? Cl2 C12 1.726(5) . ? N1 C5 1.319(5) . ? N1 C1 1.324(5) . ? C1 C2 1.366(5) . ? C2 C3 1.385(5) . ? C3 C4 1.384(5) . ? C3 C6 1.457(7) . ? C3 C6B 1.569(15) . ? C4 C5 1.343(5) . ? C6 C7 1.328(9) . ? C7 C8 1.512(8) . ? C8 C9 1.328(7) . ? C8 C13 1.397(8) . ? C8 C7B 1.604(12) . ? C9 C10 1.360(5) . ? C10 C11 1.369(5) . ? C11 C12 1.365(5) . ? C12 C13 1.423(7) . ? C6B C7B 1.286(16) . ? 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 C5 N1 C1 122.0(3) . . ? N1 C1 C2 119.8(3) . . ? C1 C2 C3 119.9(3) . . ? C4 C3 C2 117.4(3) . . ? C4 C3 C6 110.0(4) . . ? C2 C3 C6 132.5(5) . . ? C4 C3 C6B 139.7(6) . . ? C2 C3 C6B 102.7(6) . . ? C6 C3 C6B 30.4(4) . . ? C5 C4 C3 120.4(4) . . ? N1 C5 C4 120.5(4) . . ? C7 C6 C3 121.3(8) . . ? C6 C7 C8 121.3(6) . . ? C9 C8 C13 118.9(4) . . ? C9 C8 C7 113.5(5) . . ? C13 C8 C7 127.6(6) . . ? C9 C8 C7B 153.6(6) . . ? C13 C8 C7B 87.5(6) . . ? C7 C8 C7B 40.2(4) . . ? C8 C9 C10 121.1(5) . . ? C9 C10 C11 123.1(4) . . ? C9 C10 Cl1 118.3(4) . . ? C11 C10 Cl1 118.6(3) . . ? C12 C11 C10 117.2(4) . . ? C11 C12 C13 120.2(4) . . ? C11 C12 Cl2 118.2(3) . . ? C13 C12 Cl2 121.6(4) . . ? C8 C13 C12 119.4(4) . . ? C7B C6B C3 116.8(14) . . ? C6B C7B C8 107.0(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.639 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.066 # Attachment '13-PentaFluoroStilbazole-HCl-Salt.cif' data_13-PentaFluoroStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813291' #TrackingRef '13-PentaFluoroStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H7 Cl F5 N' _chemical_formula_weight 307.65 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' F F 0.0171 0.0103 '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' _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 8.3749(5) _cell_length_b 8.3985(5) _cell_length_c 10.2024(7) _cell_angle_alpha 66.6060(8) _cell_angle_beta 71.9947(9) _cell_angle_gamma 84.0524(9) _cell_volume 626.21(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3947 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.31 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8263 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7234 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2459 _reflns_number_gt 2145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0746P)^2^+0.3027P] 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 SHELXL _refine_ls_extinction_coef 0.033(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2459 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 Cl1 Cl 0.17073(8) 0.66726(9) 0.48161(8) 0.0712(3) Uani 1 1 d . . . F1 F 0.5336(3) 0.6349(4) 0.1501(3) 0.1138(7) Uani 1 1 d . . . F2 F 0.3268(4) 0.8927(3) 0.0730(3) 0.1385(10) Uani 1 1 d . . . F3 F 0.0191(3) 0.8282(3) 0.0682(3) 0.1357(11) Uani 1 1 d . . . F4 F -0.0784(3) 0.4999(4) 0.1416(3) 0.1178(8) Uani 1 1 d . . . F5 F 0.1296(3) 0.2397(3) 0.2167(3) 0.1106(7) Uani 1 1 d . . . N1 N 0.8200(4) -0.2302(5) 0.4070(3) 0.0941(10) Uani 1 1 d . . . H1A H 0.8877 -0.3120 0.4352 0.113 Uiso 1 1 calc R . . C1 C 0.8536(4) -0.0742(7) 0.3876(4) 0.0944(11) Uani 1 1 d . . . H1 H 0.9506 -0.0531 0.4048 0.113 Uiso 1 1 calc R . . C2 C 0.7540(4) 0.0557(4) 0.3441(4) 0.0833(9) Uani 1 1 d . . . H2 H 0.7812 0.1662 0.3321 0.100 Uiso 1 1 calc R . . C3 C 0.6103(3) 0.0294(4) 0.3160(3) 0.0649(7) Uani 1 1 d . . . C4 C 0.5770(4) -0.1376(5) 0.3385(4) 0.0805(9) Uani 1 1 d . . . H4 H 0.4811 -0.1634 0.3224 0.097 Uiso 1 1 calc R . . C5 C 0.6852(6) -0.2655(4) 0.3844(4) 0.0950(11) Uani 1 1 d . . . H5 H 0.6628 -0.3788 0.3998 0.114 Uiso 1 1 calc R . . C6 C 0.4700(6) 0.1413(6) 0.2681(5) 0.0678(9) Uani 0.70 1 d P . . H6 H 0.3800 0.0905 0.2625 0.081 Uiso 0.70 1 calc PR . . C7 C 0.4721(7) 0.3048(6) 0.2350(4) 0.0646(10) Uani 0.70 1 d P . . H7 H 0.5644 0.3520 0.2405 0.077 Uiso 0.70 1 calc PR . . C8 C 0.3385(3) 0.4258(4) 0.1882(3) 0.0646(7) Uani 1 1 d . . . C9 C 0.3824(4) 0.5958(4) 0.1501(3) 0.0725(7) Uani 1 1 d . . . C10 C 0.2777(5) 0.7311(4) 0.1094(3) 0.0845(9) Uani 1 1 d . . . C11 C 0.1232(5) 0.6989(5) 0.1067(3) 0.0824(9) Uani 1 1 d . . . C12 C 0.0737(4) 0.5332(5) 0.1435(3) 0.0780(8) Uani 1 1 d . . . C13 C 0.1806(4) 0.4014(4) 0.1818(3) 0.0718(7) Uani 1 1 d . . . C6B C 0.5563(8) 0.2151(10) 0.2707(8) 0.0409(13) Uani 0.30 1 d P . . H6B H 0.6181 0.3023 0.2687 0.049 Uiso 0.30 1 calc PR . . C7B C 0.4084(10) 0.2470(12) 0.2322(8) 0.0394(15) Uani 0.30 1 d P . . H7B H 0.3517 0.1565 0.2337 0.047 Uiso 0.30 1 calc PR . . 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 0.0637(4) 0.0737(5) 0.0836(5) -0.0375(4) -0.0202(3) -0.0046(3) F1 0.0935(14) 0.154(2) 0.1127(16) -0.0682(15) -0.0259(12) -0.0188(13) F2 0.193(3) 0.0749(13) 0.1228(19) -0.0381(13) -0.0065(18) -0.0187(15) F3 0.147(2) 0.1171(17) 0.0939(14) -0.0143(13) -0.0262(14) 0.0714(16) F4 0.0676(12) 0.185(2) 0.0948(14) -0.0501(15) -0.0226(10) 0.0076(13) F5 0.1001(15) 0.0888(14) 0.1269(17) -0.0457(12) 0.0003(12) -0.0194(11) N1 0.094(2) 0.110(2) 0.0647(15) -0.0330(16) -0.0200(14) 0.0484(19) C1 0.0572(17) 0.147(4) 0.086(2) -0.049(2) -0.0248(16) 0.001(2) C2 0.090(2) 0.0791(19) 0.081(2) -0.0369(16) -0.0096(17) -0.0256(17) C3 0.0645(15) 0.0715(16) 0.0508(13) -0.0248(12) -0.0091(11) 0.0147(12) C4 0.0649(16) 0.108(3) 0.0829(19) -0.0496(18) -0.0182(14) -0.0141(16) C5 0.135(3) 0.0612(17) 0.080(2) -0.0352(16) -0.008(2) -0.004(2) C6 0.063(2) 0.080(3) 0.067(2) -0.036(2) -0.0169(19) 0.000(2) C7 0.061(3) 0.076(3) 0.057(2) -0.031(2) -0.0065(19) -0.010(3) C8 0.0675(15) 0.0719(16) 0.0458(12) -0.0227(11) -0.0086(11) 0.0125(12) C9 0.0749(18) 0.0870(19) 0.0589(15) -0.0353(14) -0.0136(13) -0.0013(15) C10 0.113(3) 0.0628(17) 0.0626(17) -0.0241(14) -0.0052(17) 0.0004(17) C11 0.090(2) 0.083(2) 0.0541(15) -0.0179(14) -0.0158(14) 0.0318(17) C12 0.0646(16) 0.104(2) 0.0564(15) -0.0286(15) -0.0127(12) 0.0143(15) C13 0.0714(17) 0.0740(17) 0.0595(15) -0.0256(13) -0.0042(12) -0.0008(13) C6B 0.032(3) 0.040(3) 0.055(4) -0.021(3) -0.016(3) 0.001(3) C7B 0.037(4) 0.037(4) 0.051(4) -0.021(3) -0.016(3) 0.000(3) _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 F1 C9 1.340(4) . ? F2 C10 1.330(4) . ? F3 C11 1.331(3) . ? F4 C12 1.339(4) . ? F5 C13 1.340(4) . ? N1 C1 1.292(5) . ? N1 C5 1.304(5) . ? C1 C2 1.319(5) . ? C2 C3 1.378(4) . ? C3 C4 1.372(4) . ? C3 C6B 1.504(8) . ? C3 C6 1.505(6) . ? C4 C5 1.362(5) . ? C6 C7 1.278(7) . ? C7 C8 1.492(6) . ? C8 C9 1.380(4) . ? C8 C13 1.384(4) . ? C8 C7B 1.499(9) . ? C9 C10 1.370(5) . ? C10 C11 1.360(5) . ? C11 C12 1.363(5) . ? C12 C13 1.359(4) . ? C6B C7B 1.381(10) . ? 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 N1 C5 121.1(3) . . ? N1 C1 C2 121.7(3) . . ? C1 C2 C3 120.7(3) . . ? C4 C3 C2 116.3(3) . . ? C4 C3 C6B 147.5(4) . . ? C2 C3 C6B 96.2(4) . . ? C4 C3 C6 108.1(3) . . ? C2 C3 C6 135.5(3) . . ? C6B C3 C6 39.3(3) . . ? C5 C4 C3 119.7(3) . . ? N1 C5 C4 120.4(3) . . ? C7 C6 C3 121.2(5) . . ? C6 C7 C8 125.2(6) . . ? C9 C8 C13 115.2(3) . . ? C9 C8 C7 111.4(3) . . ? C13 C8 C7 133.4(3) . . ? C9 C8 C7B 141.0(4) . . ? C13 C8 C7B 103.8(4) . . ? C7 C8 C7B 29.9(3) . . ? F1 C9 C10 117.0(3) . . ? F1 C9 C8 120.3(3) . . ? C10 C9 C8 122.7(3) . . ? F2 C10 C11 120.3(3) . . ? F2 C10 C9 120.3(4) . . ? C11 C10 C9 119.5(3) . . ? F3 C11 C10 120.5(4) . . ? F3 C11 C12 119.4(4) . . ? C10 C11 C12 120.1(3) . . ? F4 C12 C13 120.1(3) . . ? F4 C12 C11 120.6(3) . . ? C13 C12 C11 119.3(3) . . ? F5 C13 C12 118.3(3) . . ? F5 C13 C8 118.5(3) . . ? C12 C13 C8 123.2(3) . . ? C7B C6B C3 115.3(7) . . ? C6B C7B C8 120.7(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.438 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.059 # Attachment '14-PentaFluoroStilbazole-Monomer.cif' data_14-PentaFluoroStilbazole-Monomer _database_code_depnum_ccdc_archive 'CCDC 813292' #TrackingRef '14-PentaFluoroStilbazole-Monomer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 F5 N' _chemical_formula_weight 271.19 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' F F 0.0171 0.0103 '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 5.8613(4) _cell_length_b 9.2231(6) _cell_length_c 10.9709(7) _cell_angle_alpha 71.3900(9) _cell_angle_beta 85.3708(9) _cell_angle_gamma 80.5834(9) _cell_volume 554.24(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3750 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 32.03 _exptl_crystal_description Bar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9236 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7983 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 29.00 _reflns_number_total 2930 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0723P)^2^+0.1099P] 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 SHELXL _refine_ls_extinction_coef 0.033(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2930 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1394 _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 F1 F 0.35528(16) 0.54029(13) 0.88038(10) 0.0652(3) Uani 1 1 d . . . F2 F 0.2530(2) 0.49335(15) 0.66495(11) 0.0783(4) Uani 1 1 d . . . F3 F -0.1651(2) 0.61671(14) 0.55697(9) 0.0730(3) Uani 1 1 d . . . F4 F -0.47311(18) 0.79536(15) 0.66630(12) 0.0774(4) Uani 1 1 d . . . F5 F -0.37671(18) 0.84498(15) 0.88140(12) 0.0753(4) Uani 1 1 d . . . N1 N 0.1683(3) 0.8688(2) 1.41633(15) 0.0650(4) Uani 1 1 d . . . C1 C 0.3060(3) 0.7803(2) 1.35736(18) 0.0667(5) Uani 1 1 d . . . H1 H 0.4489 0.7334 1.3926 0.080 Uiso 1 1 calc R . . C2 C 0.2499(3) 0.7536(2) 1.24681(17) 0.0604(4) Uani 1 1 d . . . H2 H 0.3533 0.6908 1.2096 0.073 Uiso 1 1 calc R . . C3 C 0.0372(3) 0.82164(18) 1.19220(15) 0.0505(4) Uani 1 1 d . . . C4 C -0.1062(3) 0.91334(19) 1.25425(16) 0.0561(4) Uani 1 1 d . . . H4 H -0.2508 0.9613 1.2221 0.067 Uiso 1 1 calc R . . C5 C -0.0339(3) 0.9331(2) 1.36352(17) 0.0610(4) Uani 1 1 d . . . H5 H -0.1335 0.9955 1.4027 0.073 Uiso 1 1 calc R . . C6 C -0.0448(3) 0.8027(2) 1.07569(16) 0.0562(4) Uani 1 1 d . . . H6 H -0.1906 0.8543 1.0482 0.067 Uiso 1 1 calc R . . C7 C 0.0691(3) 0.71957(18) 1.00716(14) 0.0500(3) Uani 1 1 d . . . H7 H 0.2143 0.6685 1.0362 0.060 Uiso 1 1 calc R . . C8 C -0.0035(2) 0.69680(16) 0.89018(13) 0.0444(3) Uani 1 1 d . . . C9 C 0.1480(3) 0.60743(18) 0.82916(14) 0.0474(3) Uani 1 1 d . . . C10 C 0.0982(3) 0.58104(19) 0.71814(15) 0.0517(4) Uani 1 1 d . . . C11 C -0.1121(3) 0.64355(19) 0.66309(14) 0.0522(4) Uani 1 1 d . . . C12 C -0.2683(3) 0.73291(19) 0.71949(15) 0.0524(4) Uani 1 1 d . . . C13 C -0.2148(3) 0.75784(18) 0.83077(15) 0.0498(3) 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 F1 0.0490(5) 0.0832(7) 0.0622(6) -0.0273(5) -0.0181(4) 0.0112(5) F2 0.0765(7) 0.0956(8) 0.0696(7) -0.0466(6) -0.0088(5) 0.0141(6) F3 0.0875(8) 0.0882(8) 0.0538(6) -0.0318(5) -0.0216(5) -0.0137(6) F4 0.0554(6) 0.0977(8) 0.0777(7) -0.0263(6) -0.0318(5) 0.0053(5) F5 0.0564(6) 0.0944(8) 0.0795(7) -0.0445(6) -0.0162(5) 0.0190(5) N1 0.0706(9) 0.0760(10) 0.0554(8) -0.0321(7) -0.0140(7) -0.0012(7) C1 0.0587(10) 0.0830(12) 0.0618(10) -0.0311(9) -0.0171(8) 0.0048(8) C2 0.0582(9) 0.0686(10) 0.0584(9) -0.0310(8) -0.0074(7) 0.0050(8) C3 0.0582(9) 0.0495(8) 0.0453(7) -0.0159(6) -0.0085(6) -0.0066(6) C4 0.0567(9) 0.0558(9) 0.0546(8) -0.0188(7) -0.0112(7) 0.0030(7) C5 0.0679(10) 0.0620(10) 0.0560(9) -0.0267(8) -0.0059(7) 0.0012(8) C6 0.0553(9) 0.0606(9) 0.0546(8) -0.0229(7) -0.0157(7) 0.0033(7) C7 0.0509(8) 0.0552(8) 0.0449(7) -0.0163(6) -0.0093(6) -0.0049(6) C8 0.0458(7) 0.0467(7) 0.0409(7) -0.0122(5) -0.0058(5) -0.0079(6) C9 0.0426(7) 0.0530(8) 0.0450(7) -0.0133(6) -0.0093(5) -0.0027(6) C10 0.0543(8) 0.0565(8) 0.0468(8) -0.0210(7) -0.0037(6) -0.0038(6) C11 0.0592(9) 0.0583(9) 0.0425(7) -0.0158(6) -0.0119(6) -0.0133(7) C12 0.0446(7) 0.0589(9) 0.0520(8) -0.0131(7) -0.0148(6) -0.0045(6) C13 0.0451(7) 0.0541(8) 0.0510(8) -0.0191(6) -0.0061(6) -0.0012(6) _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 F1 C9 1.3481(17) . ? F2 C10 1.3396(18) . ? F3 C11 1.3344(16) . ? F4 C12 1.3364(17) . ? F5 C13 1.3436(17) . ? N1 C5 1.324(2) . ? N1 C1 1.332(2) . ? C1 C2 1.386(2) . ? C2 C3 1.390(2) . ? C3 C4 1.389(2) . ? C3 C6 1.471(2) . ? C4 C5 1.377(2) . ? C6 C7 1.311(2) . ? C7 C8 1.470(2) . ? C8 C9 1.390(2) . ? C8 C13 1.394(2) . ? C9 C10 1.378(2) . ? C10 C11 1.372(2) . ? C11 C12 1.374(2) . ? C12 C13 1.381(2) . ? 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 C5 N1 C1 116.12(14) . . ? N1 C1 C2 124.16(16) . . ? C1 C2 C3 119.22(15) . . ? C4 C3 C2 116.44(15) . . ? C4 C3 C6 118.63(15) . . ? C2 C3 C6 124.92(15) . . ? C5 C4 C3 119.87(16) . . ? N1 C5 C4 124.18(16) . . ? C7 C6 C3 125.88(15) . . ? C6 C7 C8 128.26(15) . . ? C9 C8 C13 114.61(13) . . ? C9 C8 C7 119.13(13) . . ? C13 C8 C7 126.26(14) . . ? F1 C9 C10 116.99(14) . . ? F1 C9 C8 119.34(12) . . ? C10 C9 C8 123.67(13) . . ? F2 C10 C11 120.10(14) . . ? F2 C10 C9 120.23(14) . . ? C11 C10 C9 119.66(14) . . ? F3 C11 C10 120.48(15) . . ? F3 C11 C12 120.47(14) . . ? C10 C11 C12 119.05(13) . . ? F4 C12 C11 119.63(14) . . ? F4 C12 C13 120.04(15) . . ? C11 C12 C13 120.33(14) . . ? F5 C13 C12 117.11(13) . . ? F5 C13 C8 120.21(13) . . ? C12 C13 C8 122.68(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.259 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.056 # Attachment '15-4FluorStilbazole-HCl-Salt.cif' data_15-4FluorStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813293' #TrackingRef '15-4FluorStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 Cl F N O2.50' _chemical_formula_weight 281.73 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.0809(4) _cell_length_b 9.6992(6) _cell_length_c 22.3919(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.4170(10) _cell_angle_gamma 90.00 _cell_volume 1521.29(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4199 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.74 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8765 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11738 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2687 _reflns_number_gt 2115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.020(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2687 _refine_ls_number_parameters 212 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.1094 _refine_ls_wR_factor_ref 0.3869 _refine_ls_wR_factor_gt 0.3589 _refine_ls_goodness_of_fit_ref 1.717 _refine_ls_restrained_S_all 1.738 _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 Cl1 Cl 0.60718(19) 0.15921(15) 0.19645(6) 0.1069(8) Uani 1 1 d . . . F1 F 0.8799(4) 0.7329(4) 0.29049(12) 0.1138(12) Uani 1 1 d . . . N1 N 0.6649(4) 0.3979(4) -0.16935(16) 0.0785(10) Uani 1 1 d . . . H1 H 0.6463 0.3746 -0.2068 0.094 Uiso 1 1 calc R . . C1 C 0.6447(6) 0.5278(4) -0.1541(2) 0.0801(12) Uani 1 1 d . . . H1A H 0.6091 0.5937 -0.1838 0.096 Uiso 1 1 calc R . . C2 C 0.6754(6) 0.5649(5) -0.0958(2) 0.0850(12) Uani 1 1 d . . . H2 H 0.6626 0.6572 -0.0857 0.102 Uiso 1 1 calc R . . C3 C 0.7262(5) 0.4689(6) -0.04981(18) 0.0852(14) Uani 1 1 d . . . C4 C 0.7462(7) 0.3331(6) -0.0688(3) 0.0972(15) Uani 1 1 d . . . H4 H 0.7822 0.2645 -0.0404 0.117 Uiso 1 1 calc R . . C5 C 0.7145(6) 0.3014(4) -0.1267(3) 0.0869(13) Uani 1 1 d . . . H5 H 0.7267 0.2101 -0.1383 0.104 Uiso 1 1 calc R . . C6 C 0.7665(7) 0.4774(8) 0.0167(3) 0.0588(14) Uani 0.60 1 d P . . H6 H 0.7998 0.3989 0.0397 0.071 Uiso 0.60 1 calc PR . . C7 C 0.7543(9) 0.6011(8) 0.0434(5) 0.0657(16) Uani 0.60 1 d P . . H7 H 0.7223 0.6787 0.0197 0.079 Uiso 0.60 1 calc PR . . C8 C 0.7918(6) 0.6152(6) 0.1114(2) 0.0902(15) Uani 1 1 d . . . C9 C 0.7792(6) 0.7508(5) 0.1293(2) 0.0891(13) Uani 1 1 d . . . H9 H 0.7490 0.8181 0.0998 0.107 Uiso 1 1 calc R . . C10 C 0.8089(6) 0.7894(5) 0.1875(2) 0.0888(13) Uani 1 1 d . . . H10 H 0.8016 0.8820 0.1976 0.107 Uiso 1 1 calc R . . C11 C 0.8496(5) 0.6931(4) 0.2314(2) 0.0788(12) Uani 1 1 d . . . C12 C 0.8637(6) 0.5562(5) 0.2180(3) 0.0946(14) Uani 1 1 d . . . H12 H 0.8912 0.4910 0.2485 0.114 Uiso 1 1 calc R . . C13 C 0.8357(6) 0.5170(5) 0.1576(3) 0.0961(16) Uani 1 1 d . . . H13 H 0.8462 0.4245 0.1476 0.115 Uiso 1 1 calc R . . C6B C 0.7465(16) 0.566(2) 0.0076(8) 0.083(3) Uani 0.40 1 d P . . H6B H 0.7297 0.6610 0.0028 0.100 Uiso 0.40 1 calc PR . . C7B C 0.7865(13) 0.5147(15) 0.0614(5) 0.069(2) Uani 0.40 1 d P . . H7B H 0.8102 0.4212 0.0681 0.083 Uiso 0.40 1 calc PR . . H1S H 0.758(9) 0.872(2) 0.887(5) 0.17(3) Uiso 1 1 d D . . H2S H 0.651(3) 0.976(4) 0.9014(18) 0.066(12) Uiso 1 1 d D . . H3S H 0.849(9) 0.055(4) 0.099(6) 0.22(5) Uiso 1 1 d D . . H4S H 0.738(2) 0.164(2) 0.0805(12) 0.028(6) Uiso 1 1 d D . . H5S H 0.516(13) 0.02(2) 0.964(3) 0.38(10) Uiso 1 1 d D . . H6S H 0.3707(17) 0.022(3) 1.0002(14) 0.008(5) Uiso 1 1 d D . . O1 O 0.7646(10) 0.9599(6) 0.8923(3) 0.1541(19) Uani 1 1 d D . . O2 O 0.8598(9) 0.1406(6) 0.0884(2) 0.1319(15) Uani 1 1 d D . . O3 O 0.5000 0.0000 1.0000 0.323(10) Uani 1 2 d SD . . 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 0.1099(11) 0.1145(12) 0.0986(11) 0.0343(7) 0.0226(8) 0.0306(6) F1 0.1018(19) 0.156(3) 0.0821(18) -0.0350(18) 0.0066(14) 0.0067(17) N1 0.0675(18) 0.094(2) 0.076(2) -0.0093(17) 0.0160(15) -0.0119(15) C1 0.078(2) 0.078(2) 0.085(3) 0.012(2) 0.015(2) -0.0023(18) C2 0.073(2) 0.082(2) 0.103(3) -0.010(2) 0.021(2) -0.0064(19) C3 0.0487(19) 0.138(4) 0.070(2) 0.004(2) 0.0111(16) -0.011(2) C4 0.074(3) 0.121(4) 0.097(3) 0.034(3) 0.013(2) 0.005(2) C5 0.073(2) 0.072(2) 0.117(4) 0.005(2) 0.016(2) 0.0024(18) C6 0.055(3) 0.049(3) 0.073(4) 0.002(3) 0.010(2) 0.003(2) C7 0.060(3) 0.047(4) 0.090(5) 0.002(4) 0.010(3) -0.002(3) C8 0.059(2) 0.120(4) 0.094(3) -0.039(3) 0.020(2) -0.022(2) C9 0.084(3) 0.091(3) 0.094(3) -0.005(2) 0.020(2) -0.009(2) C10 0.082(3) 0.079(3) 0.106(3) -0.018(2) 0.016(2) -0.0025(19) C11 0.064(2) 0.089(3) 0.083(3) -0.017(2) 0.0111(18) 0.0031(17) C12 0.078(3) 0.091(3) 0.114(3) 0.003(3) 0.010(2) 0.005(2) C13 0.072(2) 0.074(3) 0.142(5) -0.035(3) 0.016(3) -0.0014(19) C6B 0.073(6) 0.074(9) 0.099(9) -0.010(8) 0.004(6) 0.003(5) C7B 0.061(5) 0.073(7) 0.076(6) -0.019(6) 0.017(4) -0.001(4) O1 0.183(6) 0.134(4) 0.145(4) -0.034(3) 0.025(4) 0.001(3) O2 0.163(5) 0.131(4) 0.100(3) 0.006(2) 0.016(3) -0.004(3) O3 0.80(3) 0.142(8) 0.0134(18) -0.007(3) 0.015(8) -0.168(14) _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 F1 C11 1.365(5) . ? N1 C1 1.319(6) . ? N1 C5 1.347(6) . ? N1 H1 0.8600 . ? C1 C2 1.341(7) . ? C1 H1A 0.9300 . ? C2 C3 1.397(7) . ? C2 H2 0.9300 . ? C3 C4 1.397(8) . ? C3 C6 1.477(8) . ? C3 C6B 1.59(2) . ? C4 C5 1.319(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.349(10) . ? C6 H6 0.9300 . ? C7 C8 1.512(13) . ? C7 H7 0.9300 . ? C8 C9 1.381(7) . ? C8 C13 1.407(8) . ? C8 C7B 1.482(12) . ? C9 C10 1.342(7) . ? C9 H9 0.9300 . ? C10 C11 1.357(7) . ? C10 H10 0.9300 . ? C11 C12 1.368(7) . ? C12 C13 1.391(8) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C6B C7B 1.30(2) . ? C6B H6B 0.9300 . ? C7B H7B 0.9300 . ? O1 H1S 0.865(11) . ? O1 H2S 0.872(10) . ? O2 H3S 0.867(10) . ? O2 H4S 0.887(10) . ? O3 H5S 0.855(11) . ? O3 H6S 0.941(9) . ? 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 N1 C5 120.5(4) . . ? C1 N1 H1 119.7 . . ? C5 N1 H1 119.7 . . ? N1 C1 C2 120.0(4) . . ? N1 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C1 C2 C3 121.8(4) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 115.5(4) . . ? C2 C3 C6 134.2(5) . . ? C4 C3 C6 110.3(5) . . ? C2 C3 C6B 100.6(7) . . ? C4 C3 C6B 143.9(7) . . ? C6 C3 C6B 33.6(5) . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 N1 121.6(4) . . ? C4 C5 H5 119.2 . . ? N1 C5 H5 119.2 . . ? C7 C6 C3 118.8(9) . . ? C7 C6 H6 120.6 . . ? C3 C6 H6 120.6 . . ? C6 C7 C8 120.9(8) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C13 116.6(4) . . ? C9 C8 C7B 148.2(8) . . ? C13 C8 C7B 95.1(7) . . ? C9 C8 C7 111.6(6) . . ? C13 C8 C7 131.7(5) . . ? C7B C8 C7 36.7(5) . . ? C10 C9 C8 122.6(5) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 F1 119.6(4) . . ? C10 C11 C12 121.6(4) . . ? F1 C11 C12 118.8(5) . . ? C11 C12 C13 118.3(5) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C12 C13 C8 121.0(4) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C7B C6B C3 120.3(17) . . ? C7B C6B H6B 119.9 . . ? C3 C6B H6B 119.9 . . ? C6B C7B C8 115.2(17) . . ? C6B C7B H7B 122.4 . . ? C8 C7B H7B 122.4 . . ? H1S O1 H2S 100(4) . . ? H3S O2 H4S 100(4) . . ? H5S O3 H6S 102(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.267 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.107 # Attachment '2-4FluoroStilbazole-Monomer.cif' data_2-4FluoroStilbazole-Monomer _database_code_depnum_ccdc_archive 'CCDC 813294' #TrackingRef '2-4FluoroStilbazole-Monomer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 F N' _chemical_formula_weight 199.22 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.5432(6) _cell_length_b 11.7934(9) _cell_length_c 11.8041(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1050.09(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2366 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 24.17 _exptl_crystal_description Bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8006 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.49 _reflns_number_total 970 _reflns_number_gt 757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0492P)^2^+0.2838P] 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 SHELXL _refine_ls_extinction_coef 0.040(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 970 _refine_ls_number_parameters 74 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1376 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 N1 N 0.0565(3) 0.3647(2) 0.3442(2) 0.0977(7) Uani 0.50 1 d P A 2 C1 C 0.0565(3) 0.3647(2) 0.3442(2) 0.0977(7) Uani 0.50 1 d P B 1 C2 C -0.0223(3) 0.3381(2) 0.4441(2) 0.0909(7) Uani 1 1 d . B 1 H2 H -0.0685 0.3960 0.4888 0.109 Uiso 1 1 calc R B 1 C3 C -0.0356(3) 0.2289(2) 0.48076(17) 0.0815(6) Uani 1 1 d . B 1 H3 H -0.0914 0.2135 0.5493 0.098 Uiso 1 1 calc R B 1 C4 C 0.0330(2) 0.14066(18) 0.41722(16) 0.0735(6) Uani 1 1 d . B 1 C5 C 0.1119(3) 0.1682(2) 0.31518(17) 0.0866(7) Uani 1 1 d . B 1 H5 H 0.1580 0.1111 0.2695 0.104 Uiso 1 1 calc R B 1 C6 C 0.1227(3) 0.2790(2) 0.28072(18) 0.0940(7) Uani 1 1 d . B 1 H6 H 0.1770 0.2958 0.2120 0.113 Uiso 1 1 calc R B 1 C7 C 0.0290(3) 0.0199(2) 0.45242(16) 0.0863(7) Uani 1 1 d . . 1 H7 H 0.0727 -0.0326 0.4007 0.104 Uiso 1 1 calc R . 1 F1 F 0.0699(4) 0.4572(2) 0.3152(2) 0.1113(10) Uani 0.50 1 d P B 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 N1 0.0738(12) 0.1124(18) 0.1070(16) 0.0112(14) -0.0146(12) -0.0182(12) C1 0.0738(12) 0.1124(18) 0.1070(16) 0.0112(14) -0.0146(12) -0.0182(12) C2 0.0746(13) 0.0945(16) 0.1036(16) -0.0172(13) 0.0008(12) -0.0016(11) C3 0.0657(11) 0.1062(16) 0.0726(12) -0.0100(11) 0.0071(9) -0.0099(10) C4 0.0573(10) 0.0926(13) 0.0707(11) -0.0074(10) -0.0026(8) -0.0087(9) C5 0.0735(13) 0.1156(17) 0.0707(12) -0.0136(12) 0.0044(10) -0.0050(11) C6 0.0705(12) 0.143(2) 0.0685(13) 0.0112(13) -0.0002(10) -0.0194(13) C7 0.0698(12) 0.1131(17) 0.0760(12) -0.0235(12) 0.0059(10) -0.0052(11) F1 0.117(2) 0.0899(18) 0.127(2) 0.0370(16) -0.0193(16) -0.0115(15) _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 C2 C3 1.363(3) . ? C3 C4 1.383(3) . ? C4 C5 1.382(3) . ? C4 C7 1.483(3) . ? C5 C6 1.371(3) . ? C7 C7 1.294(4) 5_556 ? 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 C3 C4 120.8(2) . . ? C5 C4 C3 117.2(2) . . ? C5 C4 C7 118.59(18) . . ? C3 C4 C7 124.23(18) . . ? C6 C5 C4 120.6(2) . . ? C7 C7 C4 126.8(3) 5_556 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.117 _refine_diff_density_rms 0.032 # Attachment '3-4ChloroStilbazole-HCl-Salt.cif' data_3-4ChloroStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813295' #TrackingRef '3-4ChloroStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl2 N O2' _chemical_formula_weight 288.16 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' Cl Cl 0.1484 0.1585 '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 7.6093(5) _cell_length_b 9.1045(5) _cell_length_c 10.7778(6) _cell_angle_alpha 102.5029(8) _cell_angle_beta 101.8363(9) _cell_angle_gamma 92.2888(9) _cell_volume 710.68(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4365 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 31.03 _exptl_crystal_description Bar _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.450 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6625 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9570 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3416 _reflns_number_gt 2789 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0839P)^2^+0.1511P] 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 3416 _refine_ls_number_parameters 167 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.043 _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 Cl1 Cl 0.91735(7) 0.70698(6) 0.43236(5) 0.06625(19) Uani 1 1 d . . . Cl2 Cl 0.60427(7) 0.31353(6) 0.67648(5) 0.06416(18) Uani 1 1 d . . . N1 N 0.6254(2) 1.21769(19) 1.39261(15) 0.0555(4) Uani 1 1 d . . . H1A H 0.6040 1.2485 1.4689 0.067 Uiso 1 1 calc R . . C1 C 0.6292(2) 1.0691(2) 1.34492(18) 0.0543(4) Uani 1 1 d . . . H1 H 0.6051 1.0010 1.3936 0.065 Uiso 1 1 calc R . . C2 C 0.6681(2) 1.0164(2) 1.22530(17) 0.0491(4) Uani 1 1 d . . . H2 H 0.6715 0.9133 1.1937 0.059 Uiso 1 1 calc R . . C3 C 0.7028(2) 1.11805(18) 1.15067(16) 0.0433(3) Uani 1 1 d . . . C4 C 0.6936(3) 1.2722(2) 1.20391(19) 0.0557(4) Uani 1 1 d . . . H4 H 0.7146 1.3433 1.1571 0.067 Uiso 1 1 calc R . . C5 C 0.6541(3) 1.3186(2) 1.3241(2) 0.0625(5) Uani 1 1 d . . . H5 H 0.6473 1.4208 1.3580 0.075 Uiso 1 1 calc R . . C6 C 0.7446(2) 1.07138(19) 1.02205(16) 0.0467(4) Uani 1 1 d . . . H6 H 0.7632 1.1468 0.9789 0.056 Uiso 1 1 calc R . . C7 C 0.7581(2) 0.92934(18) 0.96158(16) 0.0444(4) Uani 1 1 d . . . H7 H 0.7409 0.8549 1.0060 0.053 Uiso 1 1 calc R . . C8 C 0.7972(2) 0.87878(18) 0.83193(15) 0.0414(3) Uani 1 1 d . . . C9 C 0.8005(2) 0.72425(19) 0.78052(18) 0.0501(4) Uani 1 1 d . . . H9 H 0.7784 0.6560 0.8296 0.060 Uiso 1 1 calc R . . C10 C 0.8359(3) 0.6700(2) 0.65805(19) 0.0541(4) Uani 1 1 d . . . H10 H 0.8373 0.5669 0.6254 0.065 Uiso 1 1 calc R . . C11 C 0.8687(2) 0.7718(2) 0.58610(17) 0.0467(4) Uani 1 1 d . . . C12 C 0.8666(2) 0.9260(2) 0.63359(18) 0.0508(4) Uani 1 1 d . . . H12 H 0.8891 0.9934 0.5838 0.061 Uiso 1 1 calc R . . C13 C 0.8307(2) 0.97884(19) 0.75541(17) 0.0481(4) Uani 1 1 d . . . H13 H 0.8287 1.0821 0.7870 0.058 Uiso 1 1 calc R . . O1 O 0.3867(3) 0.38379(19) 0.90131(19) 0.0865(5) Uani 1 1 d D . . O2 O -0.0049(3) 0.6158(2) 0.1166(2) 0.0971(6) Uani 1 1 d D . . H1S H 0.4392 0.3764 0.8407 0.062(6) Uiso 1 1 d RD . . H2S H 0.2741 0.3902 0.8747 0.28(4) Uiso 1 1 d RD . . H3S H -0.0421 0.5274 0.1131 0.062(7) Uiso 1 1 d RD . . H4S H 0.1049 0.6231 0.1542 0.159(18) Uiso 1 1 d RD . . 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 0.0693(3) 0.0784(4) 0.0501(3) 0.0039(2) 0.0233(2) 0.0013(2) Cl2 0.0778(4) 0.0620(3) 0.0539(3) 0.0071(2) 0.0242(2) 0.0050(2) N1 0.0489(8) 0.0687(10) 0.0432(7) 0.0022(7) 0.0091(6) 0.0011(7) C1 0.0513(9) 0.0650(11) 0.0481(9) 0.0169(8) 0.0103(7) 0.0039(8) C2 0.0529(9) 0.0465(8) 0.0475(9) 0.0116(7) 0.0094(7) 0.0047(7) C3 0.0389(8) 0.0456(8) 0.0414(8) 0.0074(6) 0.0031(6) 0.0006(6) C4 0.0647(11) 0.0448(9) 0.0561(10) 0.0085(8) 0.0140(8) -0.0006(8) C5 0.0667(12) 0.0523(10) 0.0608(11) -0.0031(9) 0.0145(9) 0.0001(9) C6 0.0501(9) 0.0456(8) 0.0445(8) 0.0118(7) 0.0098(7) 0.0015(7) C7 0.0453(8) 0.0461(8) 0.0425(8) 0.0129(7) 0.0081(6) 0.0039(6) C8 0.0379(7) 0.0445(8) 0.0406(8) 0.0102(6) 0.0059(6) 0.0027(6) C9 0.0596(10) 0.0432(8) 0.0513(9) 0.0156(7) 0.0155(8) 0.0052(7) C10 0.0617(10) 0.0448(9) 0.0557(10) 0.0070(7) 0.0175(8) 0.0060(7) C11 0.0405(8) 0.0546(9) 0.0429(8) 0.0067(7) 0.0097(6) 0.0024(7) C12 0.0533(9) 0.0536(9) 0.0490(9) 0.0179(7) 0.0129(7) 0.0022(7) C13 0.0547(9) 0.0404(8) 0.0493(9) 0.0105(7) 0.0114(7) 0.0040(7) O1 0.1136(15) 0.0750(11) 0.0784(11) 0.0137(9) 0.0421(11) 0.0067(10) O2 0.0983(15) 0.0817(13) 0.0951(14) 0.0024(10) 0.0020(11) 0.0131(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 C11 1.7538(18) . ? N1 C5 1.335(3) . ? N1 C1 1.343(3) . ? N1 H1A 0.8600 . ? C1 C2 1.371(3) . ? C1 H1 0.9300 . ? C2 C3 1.401(2) . ? C2 H2 0.9300 . ? C3 C4 1.407(2) . ? C3 C6 1.463(2) . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.334(2) . ? C6 H6 0.9300 . ? C7 C8 1.469(2) . ? C7 H7 0.9300 . ? C8 C9 1.399(2) . ? C8 C13 1.403(2) . ? C9 C10 1.390(3) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O1 H1S 0.8249 . ? O1 H2S 0.8541 . ? O2 H3S 0.8327 . ? O2 H4S 0.8437 . ? 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 C5 N1 C1 121.39(17) . . ? C5 N1 H1A 119.3 . . ? C1 N1 H1A 119.3 . . ? N1 C1 C2 120.84(17) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.96(17) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 116.95(16) . . ? C2 C3 C6 123.45(15) . . ? C4 C3 C6 119.59(15) . . ? C5 C4 C3 120.66(18) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 120.17(18) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C3 125.28(15) . . ? C7 C6 H6 117.4 . . ? C3 C6 H6 117.4 . . ? C6 C7 C8 126.56(15) . . ? C6 C7 H7 116.7 . . ? C8 C7 H7 116.7 . . ? C9 C8 C13 117.75(15) . . ? C9 C8 C7 119.34(14) . . ? C13 C8 C7 122.91(15) . . ? C10 C9 C8 121.77(16) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C11 C10 C9 118.78(17) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 121.22(16) . . ? C10 C11 Cl1 119.82(14) . . ? C12 C11 Cl1 118.96(14) . . ? C13 C12 C11 119.58(16) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 120.91(16) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? H1S O1 H2S 110.7 . . ? H3S O2 H4S 104.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.301 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.073 # Attachment '4-4ChloroStilbazole-Dimer.cif' data_4-4ChloroStilbazole-Dimer _database_code_depnum_ccdc_archive 'CCDC 813296' #TrackingRef '4-4ChloroStilbazole-Dimer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Cl2 N2' _chemical_formula_weight 431.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6675(6) _cell_length_b 13.8938(8) _cell_length_c 16.3247(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.2639(8) _cell_angle_gamma 90.00 _cell_volume 2186.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6086 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 30.28 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8646 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23257 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 29.00 _reflns_number_total 5809 _reflns_number_gt 4201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0513P)^2^+0.7185P] 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 5809 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Cl1 Cl 0.47090(8) 0.81300(5) 0.91591(3) 0.0825(2) Uani 1 1 d . . . Cl2 Cl 0.58855(6) 0.90812(4) 0.10823(3) 0.06373(16) Uani 1 1 d . . . N1 N 0.6096(2) 0.48995(12) 0.63704(11) 0.0670(5) Uani 1 1 d . . . N2 N 0.0872(2) 1.06625(13) 0.40500(14) 0.0723(5) Uani 1 1 d . . . C1 C 0.46008(16) 0.83584(11) 0.54678(9) 0.0368(3) Uani 1 1 d . . . H1 H 0.5005 0.8978 0.5327 0.044 Uiso 1 1 calc R . . C2 C 0.53745(16) 0.75380(11) 0.50159(9) 0.0384(3) Uani 1 1 d . . . H2 H 0.6245 0.7775 0.4818 0.046 Uiso 1 1 calc R . . C3 C 0.41771(17) 0.75531(11) 0.43128(9) 0.0379(3) Uani 1 1 d . . . H3 H 0.3769 0.6911 0.4232 0.046 Uiso 1 1 calc R . . C4 C 0.32923(16) 0.81827(11) 0.48798(9) 0.0372(3) Uani 1 1 d . . . H4 H 0.2672 0.7753 0.5156 0.045 Uiso 1 1 calc R . . C5 C 0.45680(17) 0.83056(11) 0.63886(9) 0.0382(3) Uani 1 1 d . . . C6 C 0.3383(2) 0.81141(15) 0.67818(11) 0.0556(5) Uani 1 1 d . . . H6 H 0.2548 0.8024 0.6471 0.067 Uiso 1 1 calc R . . C7 C 0.3411(2) 0.80524(16) 0.76352(11) 0.0624(5) Uani 1 1 d . . . H7 H 0.2605 0.7918 0.7892 0.075 Uiso 1 1 calc R . . C8 C 0.4645(2) 0.81936(13) 0.80910(10) 0.0519(4) Uani 1 1 d . . . C9 C 0.5833(2) 0.83981(15) 0.77193(11) 0.0538(5) Uani 1 1 d . . . H9 H 0.6662 0.8503 0.8033 0.065 Uiso 1 1 calc R . . C10 C 0.57876(18) 0.84477(14) 0.68747(10) 0.0478(4) Uani 1 1 d . . . H10 H 0.6599 0.8580 0.6624 0.057 Uiso 1 1 calc R . . C11 C 0.55958(18) 0.66100(11) 0.54774(9) 0.0405(3) Uani 1 1 d . . . C12 C 0.4530(2) 0.60324(13) 0.57030(12) 0.0536(4) Uani 1 1 d . . . H12 H 0.3613 0.6204 0.5561 0.064 Uiso 1 1 calc R . . C13 C 0.4828(2) 0.51965(14) 0.61422(12) 0.0584(5) Uani 1 1 d . . . H13 H 0.4088 0.4820 0.6286 0.070 Uiso 1 1 calc R . . C14 C 0.7109(3) 0.54540(16) 0.61461(17) 0.0811(8) Uani 1 1 d . . . H14 H 0.8016 0.5260 0.6290 0.097 Uiso 1 1 calc R . . C15 C 0.6915(2) 0.63000(15) 0.57132(14) 0.0626(5) Uani 1 1 d . . . H15 H 0.7677 0.6661 0.5581 0.075 Uiso 1 1 calc R . . C16 C 0.46037(17) 0.79546(11) 0.35115(9) 0.0377(3) Uani 1 1 d . . . C17 C 0.44886(17) 0.73856(12) 0.28089(9) 0.0397(3) Uani 1 1 d . . . H17 H 0.4136 0.6765 0.2840 0.048 Uiso 1 1 calc R . . C18 C 0.48885(17) 0.77229(13) 0.20624(10) 0.0439(4) Uani 1 1 d . . . H18 H 0.4798 0.7336 0.1597 0.053 Uiso 1 1 calc R . . C19 C 0.54178(17) 0.86331(13) 0.20213(9) 0.0416(4) Uani 1 1 d . . . C20 C 0.5569(2) 0.92172(12) 0.27043(10) 0.0477(4) Uani 1 1 d . . . H20 H 0.5945 0.9831 0.2670 0.057 Uiso 1 1 calc R . . C21 C 0.5150(2) 0.88723(12) 0.34433(10) 0.0482(4) Uani 1 1 d . . . H21 H 0.5237 0.9266 0.3905 0.058 Uiso 1 1 calc R . . C22 C 0.24625(17) 0.90425(12) 0.45686(10) 0.0405(3) Uani 1 1 d . . . C23 C 0.22978(19) 0.98276(13) 0.50767(12) 0.0505(4) Uani 1 1 d . . . H23 H 0.2723 0.9832 0.5607 0.061 Uiso 1 1 calc R . . C24 C 0.1505(2) 1.06018(14) 0.47976(16) 0.0633(5) Uani 1 1 d . . . H24 H 0.1409 1.1114 0.5156 0.076 Uiso 1 1 calc R . . C25 C 0.1017(2) 0.99029(19) 0.35668(14) 0.0716(6) Uani 1 1 d . . . H25 H 0.0575 0.9919 0.3041 0.086 Uiso 1 1 calc R . . C26 C 0.1782(2) 0.90915(15) 0.37927(11) 0.0554(5) Uani 1 1 d . . . H26 H 0.1839 0.8583 0.3426 0.066 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 Cl1 0.1211(5) 0.0941(4) 0.0320(2) 0.0020(2) 0.0047(3) 0.0021(4) Cl2 0.0692(3) 0.0842(4) 0.0395(2) 0.0103(2) 0.0156(2) 0.0023(3) N1 0.0873(13) 0.0448(9) 0.0651(11) 0.0129(8) -0.0190(9) -0.0051(9) N2 0.0732(12) 0.0585(11) 0.0871(14) 0.0270(10) 0.0200(11) 0.0145(9) C1 0.0432(8) 0.0338(7) 0.0332(7) -0.0001(6) 0.0025(6) -0.0060(6) C2 0.0428(8) 0.0385(8) 0.0339(7) 0.0021(6) 0.0040(6) -0.0033(6) C3 0.0493(9) 0.0313(7) 0.0329(7) -0.0003(6) 0.0014(6) -0.0050(6) C4 0.0436(8) 0.0356(8) 0.0323(7) 0.0001(6) 0.0020(6) -0.0051(6) C5 0.0484(9) 0.0328(8) 0.0332(7) -0.0023(6) 0.0018(6) -0.0050(6) C6 0.0542(11) 0.0724(13) 0.0397(9) -0.0039(8) 0.0012(8) -0.0226(9) C7 0.0673(13) 0.0795(14) 0.0416(9) -0.0018(9) 0.0130(9) -0.0252(11) C8 0.0765(13) 0.0492(10) 0.0297(8) 0.0000(7) 0.0020(8) -0.0006(9) C9 0.0542(11) 0.0653(12) 0.0402(9) -0.0082(8) -0.0077(8) 0.0053(9) C10 0.0463(9) 0.0581(11) 0.0389(8) -0.0053(7) 0.0033(7) -0.0019(8) C11 0.0537(10) 0.0357(8) 0.0320(7) -0.0005(6) 0.0030(6) 0.0000(7) C12 0.0527(10) 0.0491(10) 0.0604(11) 0.0130(8) 0.0123(9) 0.0028(8) C13 0.0753(14) 0.0449(10) 0.0558(11) 0.0091(8) 0.0104(10) -0.0090(9) C14 0.0699(14) 0.0581(13) 0.110(2) 0.0258(13) -0.0307(14) -0.0039(11) C15 0.0542(11) 0.0515(11) 0.0796(14) 0.0145(10) -0.0126(10) -0.0073(9) C16 0.0460(9) 0.0346(8) 0.0324(7) -0.0006(6) 0.0018(6) -0.0003(6) C17 0.0440(9) 0.0354(8) 0.0394(8) -0.0053(6) 0.0009(6) -0.0010(6) C18 0.0469(9) 0.0500(10) 0.0345(8) -0.0109(7) 0.0009(7) 0.0020(7) C19 0.0432(9) 0.0499(9) 0.0320(7) 0.0034(7) 0.0052(6) 0.0054(7) C20 0.0640(11) 0.0370(8) 0.0428(9) 0.0013(7) 0.0096(8) -0.0073(8) C21 0.0721(12) 0.0383(9) 0.0349(8) -0.0065(6) 0.0073(8) -0.0107(8) C22 0.0419(8) 0.0401(8) 0.0399(8) 0.0042(7) 0.0050(6) -0.0041(7) C23 0.0520(10) 0.0458(10) 0.0537(10) -0.0035(8) 0.0042(8) -0.0013(8) C24 0.0644(13) 0.0433(10) 0.0840(15) 0.0010(10) 0.0176(11) 0.0028(9) C25 0.0748(15) 0.0838(16) 0.0555(12) 0.0259(12) 0.0008(10) 0.0147(12) C26 0.0644(12) 0.0578(11) 0.0431(9) 0.0038(8) -0.0021(8) 0.0072(9) _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 C8 1.7424(17) . ? Cl2 C19 1.7450(16) . ? N1 C14 1.320(3) . ? N1 C13 1.321(3) . ? N2 C24 1.327(3) . ? N2 C25 1.331(3) . ? C1 C5 1.508(2) . ? C1 C4 1.549(2) . ? C1 C2 1.576(2) . ? C2 C11 1.501(2) . ? C2 C3 1.569(2) . ? C3 C16 1.508(2) . ? C3 C4 1.572(2) . ? C4 C22 1.506(2) . ? C5 C6 1.380(2) . ? C5 C10 1.386(2) . ? C6 C7 1.394(2) . ? C7 C8 1.373(3) . ? C8 C9 1.368(3) . ? C9 C10 1.378(2) . ? C11 C15 1.374(3) . ? C11 C12 1.378(2) . ? C12 C13 1.384(3) . ? C14 C15 1.377(3) . ? C16 C21 1.388(2) . ? C16 C17 1.391(2) . ? C17 C18 1.387(2) . ? C18 C19 1.368(2) . ? C19 C20 1.378(2) . ? C20 C21 1.386(2) . ? C22 C26 1.385(2) . ? C22 C23 1.387(2) . ? C23 C24 1.378(3) . ? C25 C26 1.383(3) . ? 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 C14 N1 C13 115.61(17) . . ? C24 N2 C25 115.64(18) . . ? C5 C1 C4 122.23(13) . . ? C5 C1 C2 118.50(13) . . ? C4 C1 C2 89.43(11) . . ? C11 C2 C3 116.67(13) . . ? C11 C2 C1 116.18(13) . . ? C3 C2 C1 89.01(11) . . ? C16 C3 C2 113.91(13) . . ? C16 C3 C4 120.06(13) . . ? C2 C3 C4 88.90(11) . . ? C22 C4 C1 118.29(13) . . ? C22 C4 C3 122.84(13) . . ? C1 C4 C3 89.86(12) . . ? C6 C5 C10 117.48(15) . . ? C6 C5 C1 123.56(14) . . ? C10 C5 C1 118.95(14) . . ? C5 C6 C7 121.45(17) . . ? C8 C7 C6 118.96(18) . . ? C9 C8 C7 120.93(16) . . ? C9 C8 Cl1 119.08(15) . . ? C7 C8 Cl1 119.99(15) . . ? C8 C9 C10 119.27(17) . . ? C9 C10 C5 121.90(17) . . ? C15 C11 C12 116.10(16) . . ? C15 C11 C2 120.32(16) . . ? C12 C11 C2 123.58(16) . . ? C11 C12 C13 119.75(18) . . ? N1 C13 C12 124.16(19) . . ? N1 C14 C15 124.4(2) . . ? C11 C15 C14 120.0(2) . . ? C21 C16 C17 117.63(14) . . ? C21 C16 C3 122.67(14) . . ? C17 C16 C3 119.67(14) . . ? C18 C17 C16 121.47(15) . . ? C19 C18 C17 119.02(14) . . ? C18 C19 C20 121.50(15) . . ? C18 C19 Cl2 119.69(13) . . ? C20 C19 Cl2 118.81(14) . . ? C19 C20 C21 118.70(16) . . ? C20 C21 C16 121.66(15) . . ? C26 C22 C23 116.14(16) . . ? C26 C22 C4 123.53(15) . . ? C23 C22 C4 120.27(15) . . ? C24 C23 C22 120.12(19) . . ? N2 C24 C23 124.1(2) . . ? N2 C25 C26 124.5(2) . . ? C25 C26 C22 119.48(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.496 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.038 # Attachment '5-4BromoStilbazole-HCl-Salt.cif' data_5-4BromoStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813297' #TrackingRef '5-4BromoStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Br Cl N O2' _chemical_formula_weight 332.62 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' 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' O O 0.0106 0.0060 '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 8.0476(5) _cell_length_b 9.7384(6) _cell_length_c 9.9178(6) _cell_angle_alpha 99.5750(10) _cell_angle_beta 98.5750(10) _cell_angle_gamma 108.0290(10) _cell_volume 711.93(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4468 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.40 _exptl_crystal_description bar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 3.068 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5846 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7695 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2523 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0598P)^2^+0.8062P] 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 2523 _refine_ls_number_parameters 167 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 1.33939(5) 0.27776(4) 1.04027(4) 0.05610(18) Uani 1 1 d . . . Cl1 Cl 0.35832(14) 0.63544(11) 0.64963(11) 0.0606(3) Uani 1 1 d . . . C1 C 0.3579(5) -0.0980(4) 0.1087(4) 0.0521(9) Uani 1 1 d . . . H1 H 0.3376 -0.0348 0.0525 0.063 Uiso 1 1 calc R . . C2 C 0.4866(5) -0.0422(4) 0.2278(4) 0.0484(8) Uani 1 1 d . . . H2 H 0.5530 0.0585 0.2531 0.058 Uiso 1 1 calc R . . C3 C 0.5195(5) -0.1361(4) 0.3127(4) 0.0437(8) Uani 1 1 d . . . C4 C 0.4136(6) -0.2854(4) 0.2692(4) 0.0570(9) Uani 1 1 d . . . H4 H 0.4304 -0.3515 0.3232 0.068 Uiso 1 1 calc R . . C5 C 0.2864(6) -0.3356(4) 0.1492(5) 0.0604(10) Uani 1 1 d . . . H5 H 0.2173 -0.4357 0.1214 0.072 Uiso 1 1 calc R . . C6 C 0.6587(5) -0.0852(4) 0.4422(4) 0.0489(8) Uani 1 1 d . . . H6 H 0.6679 -0.1555 0.4932 0.059 Uiso 1 1 calc R . . C7 C 0.7717(5) 0.0517(4) 0.4925(4) 0.0486(8) Uani 1 1 d . . . H7 H 0.7634 0.1220 0.4413 0.058 Uiso 1 1 calc R . . C8 C 0.9082(5) 0.1019(4) 0.6214(4) 0.0450(8) Uani 1 1 d . . . C9 C 1.0193(5) 0.2502(4) 0.6627(4) 0.0523(9) Uani 1 1 d . . . H9 H 1.0056 0.3151 0.6065 0.063 Uiso 1 1 calc R . . C10 C 1.1486(5) 0.3028(4) 0.7844(4) 0.0512(9) Uani 1 1 d . . . H10 H 1.2230 0.4015 0.8095 0.061 Uiso 1 1 calc R . . C11 C 1.1657(5) 0.2071(4) 0.8679(4) 0.0438(7) Uani 1 1 d . . . C12 C 1.0609(5) 0.0597(4) 0.8311(4) 0.0480(8) Uani 1 1 d . . . H12 H 1.0763 -0.0039 0.8883 0.058 Uiso 1 1 calc R . . C13 C 0.9336(5) 0.0076(4) 0.7091(4) 0.0506(9) Uani 1 1 d . . . H13 H 0.8626 -0.0921 0.6839 0.061 Uiso 1 1 calc R . . N1 N 0.2594(4) -0.2425(4) 0.0707(3) 0.0523(8) Uani 1 1 d . . . H1N H 0.1780 -0.2756 -0.0051 0.063 Uiso 1 1 calc R . . O1 O 0.0583(4) 0.6654(4) 0.8104(3) 0.0765(9) Uani 1 1 d D . . O2 O 0.2532(4) 0.3793(3) 0.3776(3) 0.0660(8) Uani 1 1 d D . . H1S H 0.1239 0.6593 0.7514 0.064(13) Uiso 1 1 d RD . . H2S H -0.0467 0.6505 0.7644 0.089(17) Uiso 1 1 d RD . . H3S H 0.3535 0.3730 0.3652 0.067(14) Uiso 1 1 d RD . . H4S H 0.2782 0.4607 0.4394 0.084(17) Uiso 1 1 d RD . . 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 0.0584(3) 0.0603(3) 0.0492(3) 0.00643(17) 0.00675(17) 0.02512(19) Cl1 0.0623(6) 0.0516(5) 0.0616(6) 0.0057(4) 0.0091(5) 0.0163(4) C1 0.049(2) 0.053(2) 0.061(2) 0.0188(18) 0.0083(18) 0.0240(17) C2 0.051(2) 0.0411(18) 0.055(2) 0.0111(16) 0.0105(17) 0.0174(15) C3 0.0477(19) 0.0463(18) 0.0441(18) 0.0122(15) 0.0168(15) 0.0214(15) C4 0.062(2) 0.047(2) 0.064(2) 0.0229(18) 0.013(2) 0.0158(18) C5 0.055(2) 0.046(2) 0.073(3) 0.0143(19) 0.010(2) 0.0093(17) C6 0.054(2) 0.051(2) 0.046(2) 0.0165(16) 0.0108(16) 0.0216(17) C7 0.053(2) 0.051(2) 0.048(2) 0.0171(16) 0.0113(16) 0.0229(17) C8 0.0488(19) 0.0479(19) 0.0426(18) 0.0113(15) 0.0123(15) 0.0207(16) C9 0.063(2) 0.0428(18) 0.059(2) 0.0208(17) 0.0174(18) 0.0214(17) C10 0.056(2) 0.0427(19) 0.054(2) 0.0122(16) 0.0091(17) 0.0158(16) C11 0.0411(17) 0.0540(19) 0.0377(17) 0.0063(14) 0.0083(14) 0.0205(15) C12 0.052(2) 0.0483(19) 0.048(2) 0.0175(16) 0.0103(16) 0.0195(16) C13 0.056(2) 0.0423(18) 0.058(2) 0.0170(16) 0.0168(18) 0.0168(16) N1 0.0381(15) 0.0586(19) 0.0551(19) 0.0058(15) 0.0043(14) 0.0156(14) O1 0.0628(19) 0.109(3) 0.0556(18) 0.0060(17) 0.0012(15) 0.0386(18) O2 0.0561(17) 0.0672(18) 0.0608(18) -0.0040(15) 0.0051(14) 0.0148(14) _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 Br1 C11 1.910(3) . ? C1 N1 1.340(5) . ? C1 C2 1.355(5) . ? C1 H1 0.9300 . ? C2 C3 1.398(5) . ? C2 H2 0.9300 . ? C3 C4 1.394(5) . ? C3 C6 1.472(5) . ? C4 C5 1.355(6) . ? C4 H4 0.9300 . ? C5 N1 1.335(5) . ? C5 H5 0.9300 . ? C6 C7 1.322(5) . ? C6 H6 0.9300 . ? C7 C8 1.456(5) . ? C7 H7 0.9300 . ? C8 C9 1.396(5) . ? C8 C13 1.403(5) . ? C9 C10 1.375(6) . ? C9 H9 0.9300 . ? C10 C11 1.370(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C12 C13 1.369(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N1 H1N 0.8600 . ? O1 H1S 0.8511 . ? O1 H2S 0.8541 . ? O2 H3S 0.8528 . ? O2 H4S 0.8644 . ? 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 N1 C1 C2 121.1(3) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 116.9(3) . . ? C4 C3 C6 119.6(3) . . ? C2 C3 C6 123.5(3) . . ? C5 C4 C3 120.8(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N1 C5 C4 120.6(4) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C3 125.7(3) . . ? C7 C6 H6 117.2 . . ? C3 C6 H6 117.2 . . ? C6 C7 C8 125.5(3) . . ? C6 C7 H7 117.2 . . ? C8 C7 H7 117.2 . . ? C9 C8 C13 117.3(3) . . ? C9 C8 C7 119.7(3) . . ? C13 C8 C7 123.0(3) . . ? C10 C9 C8 121.7(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 118.8(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 Br1 119.9(3) . . ? C12 C11 Br1 118.4(3) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 121.2(3) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? C5 N1 C1 120.6(3) . . ? C5 N1 H1N 119.7 . . ? C1 N1 H1N 119.7 . . ? H1S O1 H2S 107.5 . . ? H3S O2 H4S 106.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.807 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.078 # Attachment '6-4BromoStilbazole-Dimer.cif' data_6-4BromoStilbazole-Dimer _database_code_depnum_ccdc_archive 'CCDC 813298' #TrackingRef '6-4BromoStilbazole-Dimer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Br2 N2' _chemical_formula_weight 520.26 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' 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_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8477(5) _cell_length_b 9.4161(5) _cell_length_c 24.1091(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.2071(9) _cell_angle_gamma 90.00 _cell_volume 2235.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5924 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.60 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 3.641 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4780 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22190 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5387 _reflns_number_gt 3737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0518P)^2^+1.7435P] 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 5387 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.18362(4) 0.60190(5) 1.143938(14) 0.06968(15) Uani 1 1 d . . . Br2 Br 0.21017(5) 0.77412(4) 0.578455(16) 0.07986(17) Uani 1 1 d . . . N1 N 0.6232(3) 0.7156(4) 0.95128(13) 0.0676(8) Uani 1 1 d . . . N2 N -0.2520(3) 1.0325(4) 0.76969(13) 0.0656(8) Uani 1 1 d . . . C1 C 0.1207(3) 0.8572(3) 0.90838(12) 0.0427(6) Uani 1 1 d . . . H1 H 0.0965 0.9580 0.9104 0.051 Uiso 1 1 calc R . . C2 C 0.2482(3) 0.8335(3) 0.86962(12) 0.0415(6) Uani 1 1 d . . . H2 H 0.2636 0.9202 0.8480 0.050 Uiso 1 1 calc R . . C3 C 0.1646(3) 0.7286(3) 0.83405(12) 0.0418(6) Uani 1 1 d . . . H3 H 0.1862 0.6316 0.8459 0.050 Uiso 1 1 calc R . . C4 C 0.0308(3) 0.7776(3) 0.86417(12) 0.0421(6) Uani 1 1 d . . . H4 H -0.0165 0.6967 0.8808 0.051 Uiso 1 1 calc R . . C5 C 0.1301(3) 0.7930(3) 0.96532(12) 0.0429(6) Uani 1 1 d . . . C6 C 0.1418(3) 0.8800(3) 1.01152(13) 0.0515(7) Uani 1 1 d . . . H6 H 0.1392 0.9780 1.0069 0.062 Uiso 1 1 calc R . . C7 C 0.1573(4) 0.8242(4) 1.06442(14) 0.0589(8) Uani 1 1 d . . . H7 H 0.1647 0.8842 1.0949 0.071 Uiso 1 1 calc R . . C8 C 0.1616(3) 0.6795(4) 1.07124(13) 0.0504(7) Uani 1 1 d . . . C9 C 0.1532(3) 0.5888(3) 1.02657(13) 0.0523(8) Uani 1 1 d . . . H9 H 0.1587 0.4910 1.0316 0.063 Uiso 1 1 calc R . . C10 C 0.1362(3) 0.6460(3) 0.97401(13) 0.0526(8) Uani 1 1 d . . . H10 H 0.1286 0.5852 0.9437 0.063 Uiso 1 1 calc R . . C11 C 0.3805(3) 0.7890(3) 0.89616(12) 0.0428(6) Uani 1 1 d . . . C12 C 0.4580(3) 0.8888(4) 0.92399(14) 0.0544(8) Uani 1 1 d . . . H12 H 0.4307 0.9834 0.9250 0.065 Uiso 1 1 calc R . . C13 C 0.5760(4) 0.8470(5) 0.95015(15) 0.0648(9) Uani 1 1 d . . . H13 H 0.6263 0.9165 0.9684 0.078 Uiso 1 1 calc R . . C14 C 0.5491(4) 0.6213(5) 0.92467(18) 0.0723(11) Uani 1 1 d . . . H14 H 0.5785 0.5274 0.9250 0.087 Uiso 1 1 calc R . . C15 C 0.4298(4) 0.6524(4) 0.89609(18) 0.0646(9) Uani 1 1 d . . . H15 H 0.3837 0.5812 0.8770 0.078 Uiso 1 1 calc R . . C16 C 0.1769(3) 0.7369(3) 0.77200(13) 0.0440(7) Uani 1 1 d . . . C17 C 0.2901(3) 0.7949(4) 0.74704(14) 0.0538(8) Uani 1 1 d . . . H17 H 0.3604 0.8282 0.7694 0.065 Uiso 1 1 calc R . . C18 C 0.3029(4) 0.8051(4) 0.68996(15) 0.0592(9) Uani 1 1 d . . . H18 H 0.3807 0.8437 0.6742 0.071 Uiso 1 1 calc R . . C19 C 0.1978(4) 0.7571(3) 0.65693(13) 0.0537(8) Uani 1 1 d . . . C20 C 0.0826(4) 0.6992(4) 0.68026(14) 0.0570(8) Uani 1 1 d . . . H20 H 0.0117 0.6678 0.6578 0.068 Uiso 1 1 calc R . . C21 C 0.0732(3) 0.6883(3) 0.73765(13) 0.0523(8) Uani 1 1 d . . . H21 H -0.0037 0.6478 0.7533 0.063 Uiso 1 1 calc R . . C22 C -0.0656(3) 0.8696(3) 0.83182(12) 0.0418(6) Uani 1 1 d . . . C23 C -0.2022(3) 0.8370(4) 0.82983(14) 0.0533(8) Uani 1 1 d . . . H23 H -0.2355 0.7589 0.8491 0.064 Uiso 1 1 calc R . . C24 C -0.2896(3) 0.9216(4) 0.79895(17) 0.0654(10) Uani 1 1 d . . . H24 H -0.3814 0.8981 0.7989 0.078 Uiso 1 1 calc R . . C25 C -0.1212(4) 1.0630(4) 0.77186(15) 0.0632(9) Uani 1 1 d . . . H25 H -0.0912 1.1409 0.7516 0.076 Uiso 1 1 calc R . . C26 C -0.0260(3) 0.9884(3) 0.80173(14) 0.0536(8) Uani 1 1 d . . . H26 H 0.0643 1.0173 0.8018 0.064 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 0.0820(3) 0.0826(3) 0.04436(19) 0.00282(17) 0.00271(16) 0.0148(2) Br2 0.1278(4) 0.0602(2) 0.0516(2) -0.00225(17) 0.0047(2) -0.0079(2) N1 0.0474(17) 0.092(2) 0.0628(18) 0.0005(17) -0.0100(14) 0.0061(17) N2 0.062(2) 0.065(2) 0.0698(19) -0.0053(16) -0.0194(15) 0.0157(16) C1 0.0449(16) 0.0369(14) 0.0462(15) -0.0036(12) -0.0080(12) 0.0013(12) C2 0.0434(15) 0.0349(14) 0.0463(15) 0.0011(12) -0.0072(12) -0.0036(12) C3 0.0417(15) 0.0341(13) 0.0496(16) -0.0027(12) -0.0074(12) 0.0000(12) C4 0.0428(16) 0.0381(14) 0.0453(15) 0.0008(12) -0.0053(12) -0.0030(12) C5 0.0386(15) 0.0448(16) 0.0452(15) -0.0018(12) -0.0041(12) 0.0021(12) C6 0.0581(19) 0.0436(17) 0.0528(18) -0.0078(14) -0.0049(14) 0.0018(14) C7 0.066(2) 0.062(2) 0.0490(18) -0.0149(16) -0.0053(15) 0.0073(17) C8 0.0494(17) 0.0590(19) 0.0426(16) 0.0025(14) -0.0012(13) 0.0096(15) C9 0.062(2) 0.0438(17) 0.0509(17) 0.0031(14) -0.0054(15) 0.0031(14) C10 0.066(2) 0.0449(17) 0.0468(17) -0.0077(13) -0.0061(15) 0.0017(15) C11 0.0385(15) 0.0477(17) 0.0422(15) 0.0022(12) -0.0020(12) -0.0024(13) C12 0.0565(19) 0.0542(19) 0.0523(17) -0.0051(15) -0.0116(15) -0.0027(15) C13 0.058(2) 0.083(3) 0.053(2) -0.0078(18) -0.0147(16) -0.011(2) C14 0.055(2) 0.069(2) 0.092(3) 0.005(2) -0.007(2) 0.0185(19) C15 0.0472(19) 0.054(2) 0.092(3) -0.0091(19) -0.0123(18) -0.0001(16) C16 0.0441(16) 0.0371(15) 0.0508(16) -0.0064(12) -0.0054(13) 0.0035(12) C17 0.0460(18) 0.056(2) 0.0589(19) -0.0062(15) -0.0054(15) -0.0050(15) C18 0.057(2) 0.057(2) 0.063(2) -0.0010(16) 0.0084(16) -0.0037(16) C19 0.076(2) 0.0400(17) 0.0455(16) -0.0059(13) -0.0009(16) 0.0038(15) C20 0.065(2) 0.0530(19) 0.0527(18) -0.0146(15) -0.0135(16) -0.0039(16) C21 0.0523(18) 0.0512(18) 0.0533(18) -0.0113(14) -0.0043(14) -0.0095(15) C22 0.0405(15) 0.0432(16) 0.0417(15) -0.0062(12) -0.0040(12) 0.0032(12) C23 0.0455(18) 0.0568(19) 0.0575(19) -0.0060(15) 0.0009(14) -0.0059(15) C24 0.0394(18) 0.075(3) 0.082(3) -0.015(2) -0.0136(17) 0.0065(17) C25 0.070(2) 0.054(2) 0.065(2) 0.0097(17) -0.0066(18) 0.0081(18) C26 0.0448(17) 0.0501(18) 0.066(2) 0.0049(15) -0.0064(15) -0.0004(14) _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 Br1 C8 1.911(3) . ? Br2 C19 1.903(3) . ? N1 C14 1.315(5) . ? N1 C13 1.323(5) . ? N2 C24 1.315(5) . ? N2 C25 1.320(5) . ? C1 C5 1.502(4) . ? C1 C4 1.573(4) . ? C1 C2 1.583(4) . ? C2 C11 1.509(4) . ? C2 C3 1.544(4) . ? C3 C16 1.503(4) . ? C3 C4 1.576(4) . ? C4 C22 1.502(4) . ? C5 C6 1.387(4) . ? C5 C10 1.402(4) . ? C6 C7 1.387(5) . ? C7 C8 1.373(5) . ? C8 C9 1.377(5) . ? C9 C10 1.387(5) . ? C11 C15 1.375(5) . ? C11 C12 1.383(4) . ? C12 C13 1.378(5) . ? C14 C15 1.391(5) . ? C16 C17 1.381(5) . ? C16 C21 1.390(4) . ? C17 C18 1.386(5) . ? C18 C19 1.380(5) . ? C19 C20 1.380(5) . ? C20 C21 1.391(5) . ? C22 C23 1.381(4) . ? C22 C26 1.390(4) . ? C23 C24 1.387(5) . ? C25 C26 1.373(5) . ? 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 C14 N1 C13 115.3(3) . . ? C24 N2 C25 115.4(3) . . ? C5 C1 C4 117.4(2) . . ? C5 C1 C2 115.9(2) . . ? C4 C1 C2 88.8(2) . . ? C11 C2 C3 121.0(2) . . ? C11 C2 C1 118.3(2) . . ? C3 C2 C1 89.8(2) . . ? C16 C3 C2 118.3(2) . . ? C16 C3 C4 121.0(2) . . ? C2 C3 C4 90.1(2) . . ? C22 C4 C1 115.5(2) . . ? C22 C4 C3 117.2(2) . . ? C1 C4 C3 89.0(2) . . ? C6 C5 C10 117.4(3) . . ? C6 C5 C1 120.1(3) . . ? C10 C5 C1 122.4(3) . . ? C5 C6 C7 121.6(3) . . ? C8 C7 C6 119.3(3) . . ? C7 C8 C9 121.4(3) . . ? C7 C8 Br1 119.5(2) . . ? C9 C8 Br1 119.1(3) . . ? C8 C9 C10 118.7(3) . . ? C9 C10 C5 121.7(3) . . ? C15 C11 C12 116.2(3) . . ? C15 C11 C2 124.3(3) . . ? C12 C11 C2 119.4(3) . . ? C13 C12 C11 119.4(3) . . ? N1 C13 C12 124.9(3) . . ? N1 C14 C15 124.4(4) . . ? C11 C15 C14 119.6(3) . . ? C17 C16 C21 117.6(3) . . ? C17 C16 C3 121.5(3) . . ? C21 C16 C3 120.9(3) . . ? C16 C17 C18 122.5(3) . . ? C19 C18 C17 118.7(3) . . ? C18 C19 C20 120.7(3) . . ? C18 C19 Br2 119.7(3) . . ? C20 C19 Br2 119.6(3) . . ? C19 C20 C21 119.5(3) . . ? C16 C21 C20 121.2(3) . . ? C23 C22 C26 115.8(3) . . ? C23 C22 C4 120.3(3) . . ? C26 C22 C4 123.9(3) . . ? C22 C23 C24 119.6(3) . . ? N2 C24 C23 124.6(3) . . ? N2 C25 C26 125.0(4) . . ? C25 C26 C22 119.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.013 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.063 # Attachment '7-4IodoStilbazole-HCl-Salt.cif' data_7-4IodoStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813299' #TrackingRef '7-4IodoStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl I N O2' _chemical_formula_weight 379.61 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 8.0309(3) _cell_length_b 9.9249(4) _cell_length_c 10.0973(4) _cell_angle_alpha 97.9228(5) _cell_angle_beta 99.4160(5) _cell_angle_gamma 108.9995(5) _cell_volume 734.79(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9045 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 32.67 _exptl_crystal_description Bar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.355 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4105 _exptl_absorpt_correction_T_max 0.8340 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10574 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3889 _reflns_number_gt 3707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0345P)^2^+0.5680P] 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 3889 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 I1 I 0.15399(2) 0.218152(19) -0.050061(17) 0.04742(7) Uani 1 1 d . . . Cl1 Cl 0.86170(11) 0.13828(8) 0.64523(8) 0.05517(17) Uani 1 1 d . . . N1 N 1.2491(3) 0.7434(3) 0.9306(3) 0.0491(5) Uani 1 1 d . . . H1 H 1.3298 0.7765 1.0062 0.059 Uiso 1 1 calc R . . C8 C 0.5967(3) 0.4016(3) 0.3876(3) 0.0417(5) Uani 1 1 d . . . C3 C 0.9881(4) 0.6373(3) 0.6903(3) 0.0422(5) Uani 1 1 d . . . C7 C 0.7332(4) 0.4520(3) 0.5159(3) 0.0455(5) Uani 1 1 d . . . H7 H 0.7391 0.3835 0.5690 0.055 Uiso 1 1 calc R . . C11 C 0.3396(3) 0.2957(3) 0.1401(3) 0.0416(5) Uani 1 1 d . . . C6 C 0.8505(4) 0.5879(3) 0.5636(3) 0.0470(6) Uani 1 1 d . . . H6 H 0.8435 0.6568 0.5113 0.056 Uiso 1 1 calc R . . C10 C 0.3564(4) 0.2024(3) 0.2272(3) 0.0498(6) Uani 1 1 d . . . H10 H 0.2818 0.1049 0.2036 0.060 Uiso 1 1 calc R . . C13 C 0.5738(4) 0.4950(3) 0.2998(3) 0.0475(6) Uani 1 1 d . . . H13 H 0.6450 0.5934 0.3244 0.057 Uiso 1 1 calc R . . C9 C 0.4847(4) 0.2551(3) 0.3494(3) 0.0493(6) Uani 1 1 d . . . H9 H 0.4966 0.1919 0.4072 0.059 Uiso 1 1 calc R . . C12 C 0.4472(4) 0.4429(3) 0.1775(3) 0.0465(6) Uani 1 1 d . . . H12 H 0.4336 0.5058 0.1198 0.056 Uiso 1 1 calc R . . C2 C 1.0192(4) 0.5451(3) 0.7777(3) 0.0480(6) Uani 1 1 d . . . H2 H 0.9512 0.4460 0.7550 0.058 Uiso 1 1 calc R . . C1 C 1.1491(4) 0.6016(3) 0.8958(3) 0.0512(6) Uani 1 1 d . . . H1A H 1.1686 0.5402 0.9534 0.061 Uiso 1 1 calc R . . C5 C 1.2254(4) 0.8346(3) 0.8494(4) 0.0584(7) Uani 1 1 d . . . H5 H 1.2973 0.9328 0.8744 0.070 Uiso 1 1 calc R . . C4 C 1.0972(4) 0.7844(3) 0.7309(4) 0.0560(7) Uani 1 1 d . . . H4 H 1.0816 0.8490 0.6757 0.067 Uiso 1 1 calc R . . O1 O 0.7498(4) 0.8826(3) 0.3843(3) 0.0651(7) Uani 1 1 d . . . O2 O 0.4370(5) 0.8369(4) 0.1923(3) 0.0780(9) Uani 1 1 d . . . H1S H 0.838(6) 0.877(5) 0.378(4) 0.060(12) Uiso 1 1 d . . . H2S H 0.769(7) 0.936(6) 0.438(5) 0.079(16) Uiso 1 1 d . . . H4S H 0.377(7) 0.848(6) 0.233(5) 0.081(16) Uiso 1 1 d . . . H3S H 0.521(7) 0.844(5) 0.237(5) 0.075(14) Uiso 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 I1 0.05136(11) 0.04634(11) 0.04394(11) 0.00566(7) 0.01143(7) 0.01763(8) Cl1 0.0576(4) 0.0508(4) 0.0517(4) 0.0042(3) 0.0081(3) 0.0168(3) N1 0.0388(11) 0.0513(13) 0.0537(13) 0.0050(10) 0.0071(10) 0.0154(10) C8 0.0417(12) 0.0447(13) 0.0424(12) 0.0123(10) 0.0120(10) 0.0176(10) C3 0.0443(12) 0.0440(13) 0.0433(13) 0.0119(10) 0.0155(10) 0.0182(10) C7 0.0468(13) 0.0491(14) 0.0453(13) 0.0157(11) 0.0107(11) 0.0205(11) C11 0.0403(12) 0.0425(12) 0.0459(13) 0.0095(10) 0.0154(10) 0.0171(10) C6 0.0498(14) 0.0500(14) 0.0446(13) 0.0165(11) 0.0109(11) 0.0193(12) C10 0.0533(15) 0.0396(13) 0.0556(16) 0.0136(11) 0.0122(12) 0.0135(11) C13 0.0495(14) 0.0394(12) 0.0515(15) 0.0143(11) 0.0098(11) 0.0116(11) C9 0.0569(15) 0.0424(13) 0.0530(15) 0.0201(11) 0.0136(12) 0.0184(12) C12 0.0509(14) 0.0434(13) 0.0485(14) 0.0172(11) 0.0114(11) 0.0176(11) C2 0.0501(14) 0.0401(13) 0.0531(15) 0.0109(11) 0.0058(12) 0.0175(11) C1 0.0518(15) 0.0477(14) 0.0556(16) 0.0135(12) 0.0049(12) 0.0221(12) C5 0.0512(16) 0.0437(14) 0.072(2) 0.0134(14) 0.0105(14) 0.0066(12) C4 0.0586(17) 0.0467(15) 0.0611(18) 0.0223(13) 0.0123(14) 0.0128(13) O1 0.0552(14) 0.0716(17) 0.0543(14) -0.0089(12) 0.0066(11) 0.0157(12) O2 0.0609(16) 0.121(3) 0.0517(14) 0.0036(15) 0.0037(13) 0.0413(17) _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 I1 C11 2.100(3) . ? N1 C1 1.335(4) . ? N1 C5 1.340(4) . ? C8 C9 1.397(4) . ? C8 C13 1.402(4) . ? C8 C7 1.459(4) . ? C3 C4 1.397(4) . ? C3 C2 1.406(4) . ? C3 C6 1.453(4) . ? C7 C6 1.336(4) . ? C11 C10 1.383(4) . ? C11 C12 1.394(4) . ? C10 C9 1.384(4) . ? C13 C12 1.377(4) . ? C2 C1 1.361(4) . ? C5 C4 1.356(5) . ? 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 N1 C5 120.8(3) . . ? C9 C8 C13 118.2(3) . . ? C9 C8 C7 119.5(2) . . ? C13 C8 C7 122.3(2) . . ? C4 C3 C2 116.7(3) . . ? C4 C3 C6 119.5(3) . . ? C2 C3 C6 123.8(3) . . ? C6 C7 C8 125.7(3) . . ? C10 C11 C12 120.2(3) . . ? C10 C11 I1 120.8(2) . . ? C12 C11 I1 119.0(2) . . ? C7 C6 C3 125.5(3) . . ? C11 C10 C9 119.6(3) . . ? C12 C13 C8 120.8(3) . . ? C10 C9 C8 121.2(2) . . ? C13 C12 C11 119.9(2) . . ? C1 C2 C3 119.7(3) . . ? N1 C1 C2 121.4(3) . . ? N1 C5 C4 120.3(3) . . ? C5 C4 C3 121.1(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.542 _refine_diff_density_min -0.994 _refine_diff_density_rms 0.131 # Attachment '8-4IodoStilbazole-Dimer.cif' data_8-4IodoStilbazole-Dimer _database_code_depnum_ccdc_archive 'CCDC 813300' #TrackingRef '8-4IodoStilbazole-Dimer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 I2 N2' _chemical_formula_weight 614.24 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5861(4) _cell_length_b 9.7404(4) _cell_length_c 24.7898(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.1197(7) _cell_angle_gamma 90.00 _cell_volume 2314.68(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8204 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.80 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 2.732 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4078 _exptl_absorpt_correction_T_max 0.8532 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26408 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6755 _reflns_number_gt 4849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0494P)^2^+2.4042P] 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 6755 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.002 _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 I1 I 0.30247(3) 0.89805(3) 1.146853(10) 0.06362(10) Uani 1 1 d . . . I2 I 0.29118(4) 0.72860(3) 0.582473(11) 0.07021(11) Uani 1 1 d . . . N1 N -0.1292(3) 0.7762(4) 0.95775(14) 0.0660(9) Uani 1 1 d . . . N2 N 0.7502(4) 0.4796(4) 0.76961(15) 0.0692(10) Uani 1 1 d . . . C1 C 0.3821(3) 0.6441(3) 0.91137(13) 0.0443(7) Uani 1 1 d . . . H1 H 0.4070 0.5466 0.9133 0.053 Uiso 1 1 calc R . . C2 C 0.2497(3) 0.6672(3) 0.87373(13) 0.0436(7) Uani 1 1 d . . . H2 H 0.2335 0.5841 0.8523 0.052 Uiso 1 1 calc R . . C3 C 0.3345(3) 0.7708(3) 0.83970(13) 0.0427(6) Uani 1 1 d . . . H3 H 0.3130 0.8641 0.8519 0.051 Uiso 1 1 calc R . . C4 C 0.4726(3) 0.7207(3) 0.86824(13) 0.0444(7) Uani 1 1 d . . . H4 H 0.5233 0.7978 0.8844 0.053 Uiso 1 1 calc R . . C5 C 0.3731(3) 0.7064(3) 0.96674(13) 0.0434(7) Uani 1 1 d . . . C6 C 0.3574(4) 0.6220(4) 1.01115(15) 0.0528(8) Uani 1 1 d . . . H6 H 0.3594 0.5273 1.0066 0.063 Uiso 1 1 calc R . . C7 C 0.3387(4) 0.6763(4) 1.06221(15) 0.0573(9) Uani 1 1 d . . . H7 H 0.3290 0.6180 1.0917 0.069 Uiso 1 1 calc R . . C8 C 0.3345(3) 0.8166(4) 1.06942(13) 0.0472(7) Uani 1 1 d . . . C9 C 0.3495(4) 0.9045(4) 1.02585(14) 0.0506(8) Uani 1 1 d . . . H9 H 0.3461 0.9992 1.0306 0.061 Uiso 1 1 calc R . . C10 C 0.3697(4) 0.8487(4) 0.97503(14) 0.0503(8) Uani 1 1 d . . . H10 H 0.3813 0.9071 0.9457 0.060 Uiso 1 1 calc R . . C11 C 0.1148(3) 0.7090(3) 0.90061(13) 0.0442(7) Uani 1 1 d . . . C12 C 0.0330(4) 0.6096(4) 0.92426(16) 0.0567(9) Uani 1 1 d . . . H12 H 0.0571 0.5174 0.9217 0.068 Uiso 1 1 calc R . . C13 C -0.0849(5) 0.6489(5) 0.95170(18) 0.0703(11) Uani 1 1 d . . . H13 H -0.1380 0.5797 0.9674 0.084 Uiso 1 1 calc R . . C14 C -0.0514(4) 0.8699(5) 0.93444(18) 0.0649(10) Uani 1 1 d . . . H14 H -0.0785 0.9612 0.9378 0.078 Uiso 1 1 calc R . . C15 C 0.0680(4) 0.8424(4) 0.90520(18) 0.0613(10) Uani 1 1 d . . . H15 H 0.1166 0.9135 0.8887 0.074 Uiso 1 1 calc R . . C16 C 0.3211(3) 0.7647(3) 0.77956(14) 0.0443(7) Uani 1 1 d . . . C17 C 0.2098(4) 0.7000(4) 0.75452(16) 0.0594(9) Uani 1 1 d . . . H17 H 0.1404 0.6614 0.7758 0.071 Uiso 1 1 calc R . . C18 C 0.1981(4) 0.6907(5) 0.69879(18) 0.0653(10) Uani 1 1 d . . . H18 H 0.1215 0.6476 0.6831 0.078 Uiso 1 1 calc R . . C19 C 0.3024(4) 0.7464(4) 0.66691(14) 0.0511(8) Uani 1 1 d . . . C20 C 0.4147(4) 0.8108(4) 0.69077(14) 0.0525(8) Uani 1 1 d . . . H20 H 0.4850 0.8475 0.6694 0.063 Uiso 1 1 calc R . . C21 C 0.4235(4) 0.8211(4) 0.74636(14) 0.0523(8) Uani 1 1 d . . . H21 H 0.4990 0.8665 0.7618 0.063 Uiso 1 1 calc R . . C22 C 0.5682(3) 0.6316(3) 0.83525(12) 0.0440(7) Uani 1 1 d . . . C23 C 0.7065(4) 0.6676(4) 0.82995(16) 0.0576(9) Uani 1 1 d . . . H23 H 0.7420 0.7437 0.8480 0.069 Uiso 1 1 calc R . . C24 C 0.7925(4) 0.5877(5) 0.79690(19) 0.0695(12) Uani 1 1 d . . . H24 H 0.8858 0.6128 0.7940 0.083 Uiso 1 1 calc R . . C25 C 0.6184(5) 0.4464(4) 0.77503(18) 0.0652(10) Uani 1 1 d . . . H25 H 0.5855 0.3709 0.7559 0.078 Uiso 1 1 calc R . . C26 C 0.5254(4) 0.5164(4) 0.80735(16) 0.0558(8) Uani 1 1 d . . . H26 H 0.4338 0.4859 0.8103 0.067 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 I1 0.07310(18) 0.07546(19) 0.04230(13) -0.00085(11) 0.00164(11) 0.00949(13) I2 0.1067(2) 0.05415(15) 0.04980(15) -0.00024(11) -0.00357(14) -0.00171(14) N1 0.0490(17) 0.093(3) 0.0558(18) -0.0042(18) 0.0143(14) 0.0066(17) N2 0.069(2) 0.073(2) 0.065(2) 0.0059(18) 0.0257(17) 0.0206(18) C1 0.0451(17) 0.0412(15) 0.0466(16) 0.0034(13) 0.0096(13) 0.0021(13) C2 0.0463(17) 0.0399(16) 0.0445(16) 0.0006(12) 0.0107(13) -0.0028(13) C3 0.0437(16) 0.0392(14) 0.0451(16) 0.0006(12) 0.0101(13) -0.0016(12) C4 0.0453(17) 0.0453(16) 0.0426(16) -0.0031(13) 0.0084(13) -0.0031(13) C5 0.0395(15) 0.0475(17) 0.0433(16) -0.0006(13) 0.0068(12) 0.0016(13) C6 0.058(2) 0.0452(18) 0.055(2) 0.0047(15) 0.0085(16) 0.0042(15) C7 0.065(2) 0.057(2) 0.0508(19) 0.0130(16) 0.0065(16) 0.0035(18) C8 0.0437(17) 0.0544(18) 0.0435(16) -0.0011(14) 0.0026(13) 0.0048(14) C9 0.058(2) 0.0457(18) 0.0481(18) -0.0034(14) 0.0077(15) -0.0016(15) C10 0.060(2) 0.0492(18) 0.0417(16) 0.0056(14) 0.0094(14) 0.0009(15) C11 0.0406(16) 0.0507(18) 0.0413(15) -0.0014(13) 0.0047(12) -0.0027(13) C12 0.057(2) 0.053(2) 0.060(2) 0.0037(16) 0.0190(17) -0.0032(16) C13 0.069(3) 0.078(3) 0.064(2) 0.008(2) 0.028(2) -0.015(2) C14 0.055(2) 0.064(2) 0.076(3) 0.000(2) 0.0104(19) 0.0133(18) C15 0.053(2) 0.051(2) 0.081(3) 0.0040(19) 0.0159(18) -0.0008(16) C16 0.0435(17) 0.0407(15) 0.0487(17) 0.0051(13) 0.0072(13) 0.0029(13) C17 0.0489(19) 0.073(2) 0.057(2) 0.0084(18) 0.0061(16) -0.0110(18) C18 0.056(2) 0.074(3) 0.065(2) 0.005(2) -0.0040(18) -0.013(2) C19 0.063(2) 0.0456(18) 0.0451(17) 0.0060(14) 0.0025(15) 0.0026(15) C20 0.055(2) 0.0540(19) 0.0485(18) 0.0092(15) 0.0100(15) -0.0034(16) C21 0.0516(19) 0.0544(19) 0.0509(18) 0.0093(15) 0.0057(15) -0.0069(15) C22 0.0434(16) 0.0510(17) 0.0375(14) 0.0041(13) 0.0073(12) 0.0048(13) C23 0.0484(19) 0.069(2) 0.056(2) 0.0009(18) 0.0013(15) -0.0039(17) C24 0.0417(19) 0.090(3) 0.077(3) 0.010(2) 0.0174(18) 0.006(2) C25 0.074(3) 0.052(2) 0.070(3) -0.0100(19) 0.012(2) 0.0073(19) C26 0.052(2) 0.0523(19) 0.063(2) -0.0041(16) 0.0097(16) 0.0005(16) _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 I1 C8 2.100(3) . ? I2 C19 2.103(4) . ? N1 C14 1.314(6) . ? N1 C13 1.320(6) . ? N2 C25 1.311(6) . ? N2 C24 1.315(6) . ? C1 C5 1.504(5) . ? C1 C4 1.567(4) . ? C1 C2 1.590(5) . ? C2 C11 1.511(4) . ? C2 C3 1.548(4) . ? C3 C16 1.497(5) . ? C3 C4 1.576(5) . ? C4 C22 1.505(4) . ? C5 C6 1.382(5) . ? C5 C10 1.401(5) . ? C6 C7 1.384(5) . ? C7 C8 1.379(5) . ? C8 C9 1.386(5) . ? C9 C10 1.386(5) . ? C11 C12 1.377(5) . ? C11 C15 1.379(5) . ? C12 C13 1.374(5) . ? C14 C15 1.383(5) . ? C16 C17 1.384(5) . ? C16 C21 1.396(4) . ? C17 C18 1.389(6) . ? C18 C19 1.386(5) . ? C19 C20 1.378(5) . ? C20 C21 1.384(5) . ? C22 C23 1.378(5) . ? C22 C26 1.380(5) . ? C23 C24 1.400(6) . ? C25 C26 1.380(5) . ? 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 C14 N1 C13 114.8(3) . . ? C25 N2 C24 116.1(3) . . ? C5 C1 C4 117.6(3) . . ? C5 C1 C2 115.6(3) . . ? C4 C1 C2 88.5(2) . . ? C11 C2 C3 121.1(3) . . ? C11 C2 C1 117.5(3) . . ? C3 C2 C1 89.6(2) . . ? C16 C3 C2 118.2(3) . . ? C16 C3 C4 120.3(3) . . ? C2 C3 C4 89.7(2) . . ? C22 C4 C1 115.8(3) . . ? C22 C4 C3 116.5(3) . . ? C1 C4 C3 89.3(2) . . ? C6 C5 C10 117.9(3) . . ? C6 C5 C1 119.6(3) . . ? C10 C5 C1 122.3(3) . . ? C5 C6 C7 121.1(3) . . ? C8 C7 C6 120.1(3) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 I1 119.8(3) . . ? C9 C8 I1 119.6(3) . . ? C8 C9 C10 118.7(3) . . ? C9 C10 C5 121.6(3) . . ? C12 C11 C15 116.2(3) . . ? C12 C11 C2 119.1(3) . . ? C15 C11 C2 124.6(3) . . ? C13 C12 C11 119.0(4) . . ? N1 C13 C12 125.7(4) . . ? N1 C14 C15 124.5(4) . . ? C11 C15 C14 119.7(4) . . ? C17 C16 C21 117.2(3) . . ? C17 C16 C3 122.0(3) . . ? C21 C16 C3 120.8(3) . . ? C16 C17 C18 122.4(3) . . ? C19 C18 C17 119.0(4) . . ? C20 C19 C18 119.8(3) . . ? C20 C19 I2 120.2(3) . . ? C18 C19 I2 120.0(3) . . ? C19 C20 C21 120.4(3) . . ? C20 C21 C16 121.1(3) . . ? C23 C22 C26 116.4(3) . . ? C23 C22 C4 119.5(3) . . ? C26 C22 C4 124.1(3) . . ? C22 C23 C24 118.8(4) . . ? N2 C24 C23 124.4(4) . . ? N2 C25 C26 124.1(4) . . ? C22 C26 C25 120.1(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.682 _refine_diff_density_min -0.753 _refine_diff_density_rms 0.085 # Attachment '9-4MethoxyStilbazole-HCl-Salt.cif' data_9-4MethoxyStilbazole-HCl-Salt _database_code_depnum_ccdc_archive 'CCDC 813301' #TrackingRef '9-4MethoxyStilbazole-HCl-Salt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H58 Cl4 N3 O11' _chemical_formula_weight 922.71 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' 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' Cl Cl 0.1484 0.1585 '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 9.4503(4) _cell_length_b 12.2691(5) _cell_length_c 21.7240(9) _cell_angle_alpha 78.4586(6) _cell_angle_beta 86.8176(6) _cell_angle_gamma 84.1447(6) _cell_volume 2453.43(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9907 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 30.30 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 974 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6876 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26594 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 0.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8651 _reflns_number_gt 6738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0615P)^2^+0.6339P] 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 SHELXL _refine_ls_extinction_coef 0.0072(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8651 _refine_ls_number_parameters 645 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.86411(7) 0.36648(4) 0.79477(3) 0.0837(2) Uani 1 1 d . . . Cl2 Cl 0.15835(7) 0.60822(5) 0.86158(3) 0.0852(2) Uani 1 1 d . . . Cl3 Cl 0.14573(6) 0.64444(4) 0.52892(3) 0.07377(18) Uani 1 1 d . . . Cl4 Cl 0.00490(9) 0.99427(5) 0.79911(4) 0.1064(3) Uani 1 1 d . . . O1 O 0.67752(19) 0.50791(12) 0.94267(8) 0.0873(5) Uani 1 1 d . . . O2 O 0.66200(16) 0.53975(11) 0.60813(8) 0.0756(4) Uani 1 1 d . . . O3 O 0.34410(17) 0.46424(11) 0.71665(8) 0.0826(5) Uani 1 1 d . . . N1 N 0.2979(2) 1.36987(15) 0.88442(8) 0.0718(5) Uani 1 1 d . . . H1A H 0.2727 1.4403 0.8800 0.086 Uiso 1 1 calc R . . N2 N 0.29544(18) 1.40595(13) 0.55179(7) 0.0605(4) Uani 1 1 d . . . H2A H 0.2706 1.4765 0.5468 0.073 Uiso 1 1 calc R . . N3 N 0.7065(2) -0.40233(13) 0.77965(8) 0.0669(4) Uani 1 1 d . . . H3 H 0.7318 -0.4728 0.7844 0.080 Uiso 1 1 calc R . . C1 C 0.4305(3) 1.33149(19) 0.90076(11) 0.0742(6) Uani 1 1 d . . . H1 H 0.4946 1.3807 0.9069 0.089 Uiso 1 1 calc R . . C2 C 0.4721(2) 1.21953(18) 0.90849(10) 0.0679(5) Uani 1 1 d . . . H2 H 0.5645 1.1928 0.9200 0.082 Uiso 1 1 calc R . . C3 C 0.3768(2) 1.14547(17) 0.89925(9) 0.0623(5) Uani 1 1 d . . . C4 C 0.2412(2) 1.1908(2) 0.88186(10) 0.0743(6) Uani 1 1 d . . . H4 H 0.1745 1.1441 0.8749 0.089 Uiso 1 1 calc R . . C5 C 0.2042(3) 1.3023(2) 0.87478(11) 0.0789(6) Uani 1 1 d . . . H5 H 0.1127 1.3315 0.8631 0.095 Uiso 1 1 calc R . . C6 C 0.4111(2) 1.02538(19) 0.90600(10) 0.0702(5) Uani 1 1 d . . . H6 H 0.3390 0.9839 0.8985 0.084 Uiso 1 1 calc R . . C7 C 0.5349(2) 0.96988(18) 0.92171(10) 0.0690(5) Uani 1 1 d . . . H7 H 0.6064 1.0118 0.9293 0.083 Uiso 1 1 calc R . . C8 C 0.5723(2) 0.84902(16) 0.92856(9) 0.0601(5) Uani 1 1 d . . . C9 C 0.7100(2) 0.80409(17) 0.94076(10) 0.0672(5) Uani 1 1 d . . . H9 H 0.7779 0.8514 0.9453 0.081 Uiso 1 1 calc R . . C10 C 0.7507(2) 0.69088(18) 0.94645(10) 0.0681(5) Uani 1 1 d . . . H10 H 0.8445 0.6630 0.9545 0.082 Uiso 1 1 calc R . . C11 C 0.6504(2) 0.62014(16) 0.94002(9) 0.0634(5) Uani 1 1 d . . . C12 C 0.5119(2) 0.66264(18) 0.92902(10) 0.0709(6) Uani 1 1 d . . . H12 H 0.4437 0.6147 0.9257 0.085 Uiso 1 1 calc R . . C13 C 0.4730(2) 0.77517(18) 0.92282(10) 0.0687(5) Uani 1 1 d . . . H13 H 0.3790 0.8026 0.9147 0.082 Uiso 1 1 calc R . . C14 C 0.8188(3) 0.4578(2) 0.95600(13) 0.0973(8) Uani 1 1 d . . . H14A H 0.8841 0.4904 0.9238 0.146 Uiso 1 1 calc R . . H14B H 0.8224 0.3789 0.9573 0.146 Uiso 1 1 calc R . . H14C H 0.8446 0.4705 0.9959 0.146 Uiso 1 1 calc R . . C21 C 0.4299(2) 1.36801(16) 0.56520(9) 0.0626(5) Uani 1 1 d . . . H21 H 0.4953 1.4176 0.5694 0.075 Uiso 1 1 calc R . . C22 C 0.4713(2) 1.25613(17) 0.57280(9) 0.0617(5) Uani 1 1 d . . . H22 H 0.5650 1.2296 0.5819 0.074 Uiso 1 1 calc R . . C23 C 0.3726(2) 1.18173(15) 0.56689(9) 0.0594(5) Uani 1 1 d . . . C24 C 0.2361(2) 1.22674(18) 0.55309(10) 0.0700(5) Uani 1 1 d . . . H24 H 0.1677 1.1798 0.5486 0.084 Uiso 1 1 calc R . . C25 C 0.1994(2) 1.33774(18) 0.54594(10) 0.0692(5) Uani 1 1 d . . . H25 H 0.1063 1.3663 0.5369 0.083 Uiso 1 1 calc R . . C26 C 0.3982(3) 1.0602(3) 0.57357(12) 0.0512(6) Uani 0.80 1 d P . . H26 H 0.3226 1.0206 0.5680 0.061 Uiso 0.80 1 calc PR . . C27 C 0.5257(3) 1.0024(3) 0.58735(11) 0.0479(6) Uani 0.80 1 d P . . H27 H 0.6007 1.0423 0.5933 0.057 Uiso 0.80 1 calc PR . . C28 C 0.5539(2) 0.88081(15) 0.59364(9) 0.0579(5) Uani 1 1 d . . . C29 C 0.6905(2) 0.83606(16) 0.60567(10) 0.0632(5) Uani 1 1 d . . . H29 H 0.7582 0.8835 0.6103 0.076 Uiso 1 1 calc R . . C30 C 0.7318(2) 0.72374(16) 0.61120(9) 0.0599(5) Uani 1 1 d . . . H30 H 0.8259 0.6964 0.6190 0.072 Uiso 1 1 calc R . . C31 C 0.6324(2) 0.65222(14) 0.60507(8) 0.0540(4) Uani 1 1 d . . . C32 C 0.4931(2) 0.69385(16) 0.59414(10) 0.0634(5) Uani 1 1 d . . . H32 H 0.4253 0.6457 0.5908 0.076 Uiso 1 1 calc R . . C33 C 0.4542(2) 0.80696(17) 0.58809(10) 0.0653(5) Uani 1 1 d . . . H33 H 0.3602 0.8344 0.5802 0.078 Uiso 1 1 calc R . . C34 C 0.8040(3) 0.49207(19) 0.61999(12) 0.0871(7) Uani 1 1 d . . . H34A H 0.8676 0.5275 0.5879 0.131 Uiso 1 1 calc R . . H34B H 0.8101 0.4135 0.6199 0.131 Uiso 1 1 calc R . . H34C H 0.8302 0.5030 0.6602 0.131 Uiso 1 1 calc R . . C41 C 0.5730(2) -0.36512(17) 0.76564(10) 0.0691(5) Uani 1 1 d . . . H41 H 0.5084 -0.4149 0.7608 0.083 Uiso 1 1 calc R . . C42 C 0.5304(2) -0.25298(18) 0.75828(10) 0.0689(5) Uani 1 1 d . . . H42 H 0.4369 -0.2265 0.7488 0.083 Uiso 1 1 calc R . . C43 C 0.6287(3) -0.17925(16) 0.76522(9) 0.0652(5) Uani 1 1 d . . . C44 C 0.7652(3) -0.22343(19) 0.77974(10) 0.0746(6) Uani 1 1 d . . . H44 H 0.8330 -0.1765 0.7849 0.090 Uiso 1 1 calc R . . C45 C 0.8015(2) -0.33413(19) 0.78654(11) 0.0749(6) Uani 1 1 d . . . H45 H 0.8943 -0.3629 0.7962 0.090 Uiso 1 1 calc R . . C46 C 0.6038(4) -0.0574(3) 0.75774(12) 0.0577(6) Uani 0.80 1 d P . . H46 H 0.6799 -0.0179 0.7627 0.069 Uiso 0.80 1 calc PR . . C47 C 0.4783(4) -0.0005(3) 0.74431(12) 0.0540(6) Uani 0.80 1 d P . . H47 H 0.4031 -0.0405 0.7389 0.065 Uiso 0.80 1 calc PR . . C48 C 0.4502(2) 0.12220(15) 0.73743(9) 0.0613(5) Uani 1 1 d . . . C49 C 0.3138(2) 0.16644(16) 0.72577(10) 0.0643(5) Uani 1 1 d . . . H49 H 0.2455 0.1185 0.7226 0.077 Uiso 1 1 calc R . . C50 C 0.2729(2) 0.27909(16) 0.71857(9) 0.0600(5) Uani 1 1 d . . . H50 H 0.1786 0.3062 0.7111 0.072 Uiso 1 1 calc R . . C51 C 0.3728(2) 0.35114(14) 0.72258(9) 0.0562(4) Uani 1 1 d . . . C52 C 0.5123(2) 0.31010(17) 0.73336(10) 0.0687(5) Uani 1 1 d . . . H52 H 0.5805 0.3587 0.7353 0.082 Uiso 1 1 calc R . . C53 C 0.5507(2) 0.19641(19) 0.74121(10) 0.0707(6) Uani 1 1 d . . . H53 H 0.6447 0.1690 0.7491 0.085 Uiso 1 1 calc R . . C54 C 0.2014(3) 0.51100(19) 0.70600(12) 0.0900(8) Uani 1 1 d . . . H54A H 0.1707 0.4941 0.6679 0.135 Uiso 1 1 calc R . . H54B H 0.1965 0.5906 0.7024 0.135 Uiso 1 1 calc R . . H54C H 0.1406 0.4799 0.7406 0.135 Uiso 1 1 calc R . . H10S H 0.124(3) 0.823(2) 0.3800(9) 0.112(11) Uiso 1 1 d D . . H11S H 0.149(3) 0.7858(17) 0.4414(9) 0.106(10) Uiso 1 1 d D . . H12S H 0.095(3) 0.759(2) 0.6031(14) 0.145(13) Uiso 1 1 d D . . H13S H 0.100(3) 0.800(3) 0.6592(8) 0.143(14) Uiso 1 1 d D . . H14S H 0.095(3) 0.7410(19) 0.2837(12) 0.124(11) Uiso 1 1 d D . . H15S H 0.050(3) 0.8518(15) 0.2779(11) 0.120(11) Uiso 1 1 d D . . H16S H 0.9358(13) -0.0024(19) 0.5461(10) 0.074(7) Uiso 1 1 d D . . H17S H 1.028(3) -0.0583(14) 0.5799(12) 0.124(11) Uiso 1 1 d D . . H18S H 0.158(3) 0.7443(18) 0.7695(11) 0.134(13) Uiso 1 1 d D . . H19S H 0.122(3) 0.8555(16) 0.7515(13) 0.119(11) Uiso 1 1 d D . . H20S H 0.107(3) 0.7576(12) 0.9093(13) 0.116(10) Uiso 1 1 d D . . H21S H 0.073(4) 0.873(2) 0.8861(11) 0.154(16) Uiso 1 1 d D . . H22S H 0.851(3) 0.2053(12) 0.8625(12) 0.111(10) Uiso 1 1 d D . . H23S H 0.868(3) 0.098(2) 0.8588(12) 0.120(12) Uiso 1 1 d D . . H24S H 0.8599(8) 0.0608(8) 0.9974(5) -0.0255(16) Uiso 1 1 d D . . H25S H 0.9980(9) 0.1182(9) 0.9832(5) -0.0182(19) Uiso 1 1 d D . . O10S O 0.16110(19) 0.84094(14) 0.41122(9) 0.0816(4) Uani 1 1 d D . . O11S O 0.0608(2) 0.81024(16) 0.62335(10) 0.0943(5) Uani 1 1 d D . . O12S O 0.0676(2) 0.79109(19) 0.30572(10) 0.0976(5) Uani 1 1 d D . . O13S O 1.0210(2) 0.00683(16) 0.55445(10) 0.0900(5) Uani 1 1 d D . . O14S O 0.1666(2) 0.79970(19) 0.73895(9) 0.0969(5) Uani 1 1 d D . . O15S O 0.0936(3) 0.8217(2) 0.91818(11) 0.1141(7) Uani 1 1 d D . . O16S O 0.8322(2) 0.14075(18) 0.88364(10) 0.0965(5) Uani 1 1 d D . . O17S O 0.9286(5) 0.0841(3) 0.99123(19) 0.227(2) Uani 1 1 d D . . C47B C 0.5111(17) -0.0742(10) 0.7529(5) 0.061(3) Uani 0.20 1 d P . . H47B H 0.4154 -0.0797 0.7473 0.073 Uiso 0.20 1 calc PR . . C26B C 0.484(2) 1.0752(11) 0.5800(5) 0.066(3) Uani 0.20 1 d P . . H26B H 0.5788 1.0813 0.5874 0.080 Uiso 0.20 1 calc PR . . C46B C 0.5639(17) 0.0176(10) 0.7517(5) 0.056(2) Uani 0.20 1 d P . . H46B H 0.6591 0.0226 0.7586 0.067 Uiso 0.20 1 calc PR . . C27B C 0.443(2) 0.9897(13) 0.5799(6) 0.067(3) Uani 0.20 1 d P . . H27B H 0.3489 0.9843 0.5721 0.080 Uiso 0.20 1 calc PR . . 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 0.0970(4) 0.0525(3) 0.1034(4) -0.0211(3) -0.0366(3) 0.0146(3) Cl2 0.1015(4) 0.0619(3) 0.0942(4) -0.0232(3) -0.0270(3) 0.0119(3) Cl3 0.0820(4) 0.0497(3) 0.0900(4) -0.0161(2) -0.0288(3) 0.0111(2) Cl4 0.1396(6) 0.0556(3) 0.1243(6) -0.0212(3) 0.0073(5) -0.0101(4) O1 0.0998(12) 0.0545(9) 0.1036(12) -0.0098(8) -0.0020(9) -0.0001(8) O2 0.0876(10) 0.0406(7) 0.0980(11) -0.0158(7) -0.0014(8) 0.0010(7) O3 0.0944(11) 0.0413(7) 0.1114(12) -0.0187(7) 0.0027(9) 0.0015(7) N1 0.0885(13) 0.0620(10) 0.0625(10) -0.0157(8) -0.0068(9) 0.0132(9) N2 0.0758(11) 0.0421(8) 0.0613(9) -0.0101(7) -0.0082(8) 0.0088(8) N3 0.0880(13) 0.0451(9) 0.0660(10) -0.0129(7) -0.0105(9) 0.0096(8) C1 0.0817(15) 0.0654(13) 0.0776(14) -0.0205(11) -0.0023(12) -0.0040(11) C2 0.0624(12) 0.0666(13) 0.0733(13) -0.0150(10) -0.0023(10) 0.0034(10) C3 0.0704(13) 0.0591(11) 0.0568(11) -0.0131(9) 0.0018(9) -0.0017(10) C4 0.0712(14) 0.0766(15) 0.0770(14) -0.0197(11) -0.0132(11) -0.0013(11) C5 0.0773(15) 0.0872(16) 0.0706(14) -0.0187(12) -0.0175(11) 0.0147(13) C6 0.0700(13) 0.0686(13) 0.0731(13) -0.0168(10) -0.0041(11) -0.0055(11) C7 0.0744(14) 0.0645(13) 0.0694(13) -0.0168(10) 0.0038(11) -0.0092(11) C8 0.0663(12) 0.0564(11) 0.0566(11) -0.0094(8) 0.0019(9) -0.0064(9) C9 0.0658(13) 0.0632(12) 0.0738(13) -0.0135(10) -0.0008(10) -0.0123(10) C10 0.0625(12) 0.0663(13) 0.0724(13) -0.0100(10) -0.0016(10) 0.0007(10) C11 0.0768(14) 0.0526(11) 0.0586(11) -0.0072(9) 0.0033(10) -0.0056(10) C12 0.0722(14) 0.0625(13) 0.0799(14) -0.0138(10) -0.0038(11) -0.0146(10) C13 0.0627(12) 0.0661(13) 0.0748(13) -0.0092(10) -0.0047(10) -0.0027(10) C14 0.115(2) 0.0696(15) 0.0982(19) -0.0088(13) -0.0081(16) 0.0193(14) C21 0.0687(13) 0.0557(11) 0.0659(12) -0.0154(9) -0.0038(10) -0.0099(9) C22 0.0562(11) 0.0631(12) 0.0628(12) -0.0128(9) -0.0051(9) 0.0107(9) C23 0.0818(14) 0.0461(10) 0.0494(10) -0.0112(8) 0.0010(9) 0.0005(9) C24 0.0734(14) 0.0595(12) 0.0801(14) -0.0165(10) -0.0133(11) -0.0095(10) C25 0.0630(12) 0.0680(13) 0.0750(14) -0.0126(10) -0.0168(10) 0.0063(10) C26 0.0472(16) 0.0434(16) 0.0644(15) -0.0122(11) -0.0099(13) -0.0027(14) C27 0.0466(16) 0.0443(17) 0.0532(14) -0.0111(10) -0.0038(12) -0.0024(14) C28 0.0768(13) 0.0431(9) 0.0528(10) -0.0103(8) 0.0041(9) -0.0027(9) C29 0.0698(13) 0.0500(10) 0.0722(13) -0.0149(9) 0.0014(10) -0.0127(9) C30 0.0571(11) 0.0534(11) 0.0689(12) -0.0130(9) -0.0016(9) -0.0022(8) C31 0.0649(12) 0.0407(9) 0.0556(10) -0.0102(7) 0.0023(8) -0.0021(8) C32 0.0627(12) 0.0539(11) 0.0770(13) -0.0177(9) -0.0034(10) -0.0118(9) C33 0.0583(11) 0.0651(12) 0.0686(12) -0.0118(10) -0.0045(9) 0.0106(9) C34 0.1050(18) 0.0597(13) 0.0893(16) -0.0125(11) -0.0056(14) 0.0243(12) C41 0.0793(15) 0.0584(12) 0.0723(13) -0.0170(10) -0.0069(11) -0.0080(10) C42 0.0656(13) 0.0708(13) 0.0659(12) -0.0119(10) -0.0063(10) 0.0136(10) C43 0.0971(16) 0.0468(10) 0.0507(11) -0.0120(8) -0.0008(10) 0.0018(10) C44 0.0864(16) 0.0645(13) 0.0766(14) -0.0175(11) -0.0177(12) -0.0089(11) C45 0.0756(14) 0.0723(14) 0.0761(14) -0.0162(11) -0.0210(11) 0.0100(11) C46 0.0577(18) 0.0473(18) 0.0693(16) -0.0144(12) -0.0087(14) -0.0009(15) C47 0.0579(18) 0.0474(18) 0.0568(15) -0.0112(12) -0.0035(13) -0.0031(15) C48 0.0844(14) 0.0458(10) 0.0518(11) -0.0093(8) 0.0039(9) -0.0007(10) C49 0.0715(13) 0.0499(11) 0.0720(13) -0.0136(9) 0.0102(10) -0.0119(9) C50 0.0580(11) 0.0523(10) 0.0686(12) -0.0131(9) 0.0053(9) -0.0013(9) C51 0.0694(12) 0.0418(9) 0.0575(11) -0.0130(8) 0.0025(9) -0.0014(8) C52 0.0671(13) 0.0614(12) 0.0830(14) -0.0227(10) -0.0075(11) -0.0113(10) C53 0.0638(12) 0.0757(14) 0.0695(13) -0.0169(11) -0.0110(10) 0.0177(11) C54 0.117(2) 0.0592(13) 0.0866(16) -0.0144(12) -0.0011(14) 0.0271(13) O10S 0.0905(12) 0.0692(10) 0.0857(12) -0.0155(9) -0.0073(10) -0.0077(8) O11S 0.0994(13) 0.0799(12) 0.1052(14) -0.0315(10) -0.0255(11) 0.0226(9) O12S 0.1071(14) 0.0925(14) 0.0946(13) -0.0276(12) -0.0207(11) 0.0122(11) O13S 0.0943(14) 0.0732(11) 0.1044(14) -0.0205(10) -0.0038(11) -0.0111(10) O14S 0.1081(14) 0.0914(13) 0.0870(13) -0.0216(11) 0.0025(10) 0.0166(11) O15S 0.1368(17) 0.0985(15) 0.1156(17) -0.0565(14) -0.0392(13) 0.0371(13) O16S 0.0986(13) 0.0860(13) 0.0953(13) -0.0035(11) 0.0059(10) 0.0044(11) O17S 0.335(7) 0.181(5) 0.152(3) -0.050(3) -0.037(4) 0.092(4) C47B 0.060(8) 0.051(8) 0.067(7) -0.005(5) -0.004(5) 0.010(6) C26B 0.072(9) 0.059(9) 0.066(7) -0.016(5) -0.011(6) 0.018(7) C46B 0.047(7) 0.060(8) 0.059(6) -0.010(5) -0.005(5) 0.003(6) C27B 0.053(8) 0.078(10) 0.066(7) -0.009(6) -0.008(6) 0.012(8) _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 O1 C11 1.365(2) . ? O1 C14 1.431(3) . ? O2 C31 1.369(2) . ? O2 C34 1.424(3) . ? O3 C51 1.368(2) . ? O3 C54 1.423(3) . ? N1 C5 1.325(3) . ? N1 C1 1.334(3) . ? N2 C25 1.323(3) . ? N2 C21 1.335(2) . ? N3 C45 1.322(3) . ? N3 C41 1.327(3) . ? C1 C2 1.369(3) . ? C2 C3 1.392(3) . ? C3 C4 1.385(3) . ? C3 C6 1.456(3) . ? C4 C5 1.358(3) . ? C6 C7 1.318(3) . ? C7 C8 1.468(3) . ? C8 C9 1.378(3) . ? C8 C13 1.396(3) . ? C9 C10 1.386(3) . ? C10 C11 1.380(3) . ? C11 C12 1.374(3) . ? C12 C13 1.374(3) . ? C21 C22 1.368(3) . ? C22 C23 1.398(3) . ? C23 C24 1.374(3) . ? C23 C26 1.465(4) . ? C23 C26B 1.583(17) . ? C24 C25 1.351(3) . ? C26 C27 1.351(4) . ? C27 C28 1.468(3) . ? C28 C29 1.368(3) . ? C28 C33 1.398(3) . ? C28 C27B 1.598(17) . ? C29 C30 1.377(3) . ? C30 C31 1.378(3) . ? C31 C32 1.378(3) . ? C32 C33 1.381(3) . ? C41 C42 1.374(3) . ? C42 C43 1.395(3) . ? C43 C44 1.376(3) . ? C43 C46 1.467(4) . ? C43 C47B 1.603(15) . ? C44 C45 1.347(3) . ? C46 C47 1.329(4) . ? C47 C48 1.481(4) . ? C48 C49 1.364(3) . ? C48 C53 1.397(3) . ? C48 C46B 1.579(15) . ? C49 C50 1.377(3) . ? C50 C51 1.375(3) . ? C51 C52 1.377(3) . ? C52 C53 1.384(3) . ? C47B C46B 1.272(18) . ? C26B C27B 1.15(2) . ? 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 C11 O1 C14 118.21(19) . . ? C31 O2 C34 118.30(17) . . ? C51 O3 C54 118.17(17) . . ? C5 N1 C1 121.70(19) . . ? C25 N2 C21 121.65(17) . . ? C45 N3 C41 121.82(18) . . ? N1 C1 C2 119.9(2) . . ? C1 C2 C3 120.3(2) . . ? C4 C3 C2 116.91(19) . . ? C4 C3 C6 118.7(2) . . ? C2 C3 C6 124.37(19) . . ? C5 C4 C3 120.9(2) . . ? N1 C5 C4 120.3(2) . . ? C7 C6 C3 126.1(2) . . ? C6 C7 C8 127.1(2) . . ? C9 C8 C13 117.19(19) . . ? C9 C8 C7 120.29(19) . . ? C13 C8 C7 122.52(19) . . ? C8 C9 C10 122.31(19) . . ? C11 C10 C9 119.14(19) . . ? O1 C11 C12 115.45(19) . . ? O1 C11 C10 124.9(2) . . ? C12 C11 C10 119.64(19) . . ? C13 C12 C11 120.7(2) . . ? C12 C13 C8 121.0(2) . . ? N2 C21 C22 119.87(18) . . ? C21 C22 C23 119.98(18) . . ? C24 C23 C22 116.92(17) . . ? C24 C23 C26 115.9(2) . . ? C22 C23 C26 127.2(2) . . ? C24 C23 C26B 149.0(7) . . ? C22 C23 C26B 94.1(6) . . ? C26 C23 C26B 33.1(6) . . ? C25 C24 C23 121.4(2) . . ? N2 C25 C24 120.22(19) . . ? C27 C26 C23 123.6(4) . . ? C26 C27 C28 124.4(4) . . ? C29 C28 C33 117.17(17) . . ? C29 C28 C27 116.9(2) . . ? C33 C28 C27 126.0(2) . . ? C29 C28 C27B 148.2(7) . . ? C33 C28 C27B 94.6(7) . . ? C27 C28 C27B 31.4(6) . . ? C28 C29 C30 122.71(18) . . ? C29 C30 C31 119.34(18) . . ? O2 C31 C32 115.95(17) . . ? O2 C31 C30 124.40(17) . . ? C32 C31 C30 119.64(17) . . ? C31 C32 C33 120.09(18) . . ? C32 C33 C28 121.02(18) . . ? N3 C41 C42 119.9(2) . . ? C41 C42 C43 119.4(2) . . ? C44 C43 C42 117.67(18) . . ? C44 C43 C46 115.2(2) . . ? C42 C43 C46 127.1(2) . . ? C44 C43 C47B 150.2(6) . . ? C42 C43 C47B 92.1(5) . . ? C46 C43 C47B 35.1(5) . . ? C45 C44 C43 120.6(2) . . ? N3 C45 C44 120.6(2) . . ? C47 C46 C43 123.5(4) . . ? C46 C47 C48 124.5(4) . . ? C49 C48 C53 117.32(18) . . ? C49 C48 C47 116.7(2) . . ? C53 C48 C47 126.0(2) . . ? C49 C48 C46B 150.3(5) . . ? C53 C48 C46B 92.4(5) . . ? C47 C48 C46B 33.7(4) . . ? C48 C49 C50 122.69(19) . . ? C51 C50 C49 119.37(19) . . ? O3 C51 C50 124.37(18) . . ? O3 C51 C52 115.83(17) . . ? C50 C51 C52 119.80(17) . . ? C51 C52 C53 119.87(19) . . ? C52 C53 C48 120.94(19) . . ? C46B C47B C43 112.2(16) . . ? C27B C26B C23 117(2) . . ? C47B C46B C48 112.7(16) . . ? C26B C27B C28 118(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.049