#------------------------------------------------------------------------------ #$Date: 2022-10-10 14:50:38 +0100 (Mon, 10 Oct 2022) $ #$Revision: 278508 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500131.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500131 loop_ _publ_author_name 'Maris, Thierry' 'Lalibert\'e, Dominic' 'Raymond, Nathalie' 'Wuest, James D.' _publ_section_references ; APEX2 (2006) version 2.1-0; Bruker Molecular Analysis Research Tool. Bruker AXS Inc., Madison, WI 53719-1173. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2007). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, WI 53719-1173. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. Spek, A.L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. XPREP (2005) Version 2005/2; X-ray data Preparation and Reciprocal space Exploration Program. Bruker AXS Inc., Madison, WI 53719-1173. ; _publ_section_title ; Bis(4-nitrophenyl) sulfide ; _journal_name_full 'Personal communication to COD' _journal_year 2022 _chemical_formula_moiety 'C12 H8 N2 O4 S' _chemical_formula_sum 'C12 H8 N2 O4 S' _chemical_formula_weight 276.26 _chemical_name_common 'Bis(4-nitrophenyl) sulfide' _chemical_name_systematic ; 1-nitro-4-(4-nitrophenyl)sulfanylbenzene ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_date 2022-10-08 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 103.573(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3431(14) _cell_length_b 14.0371(13) _cell_length_c 11.816(4) _cell_measurement_reflns_used 3983 _cell_measurement_temperature 295 _cell_measurement_theta_max 68.992 _cell_measurement_theta_min 6.280 _cell_volume 1183.9(5) _computing_cell_refinement 'SAINT v6.28A (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT v6.28A (Bruker, 2002)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295 _diffrn_detector_area_resol_mean 5.5 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6011 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 69.424 _diffrn_reflns_theta_min 6.306 _exptl_absorpt_coefficient_mu 2.573 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.737213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.03 (Bruker,200?) was used for absorption correction. R(int) was 0.1574 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.7372. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _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. ; _refine_diff_density_max 0.182 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.062 _refine_ls_extinction_coef 0.0041(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 104 _refine_ls_number_reflns 1098 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0432 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.2706P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1214 _refine_ls_wR_factor_ref 0.1249 _refine_special_details ; _shelx_SHELXL_version_number 2018/3 ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 971 _reflns_number_total 1098 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jiw751.cif _cod_data_source_block jiw751 _cod_database_code 3500131 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8445(3) 0.96643(12) 0.65798(17) 0.0566(5) Uani 1 1 d . . . . . N1 N 0.4554(2) 0.78926(11) 0.43580(14) 0.0611(5) Uani 1 1 d . . . . . O1 O 0.3760(2) 0.81945(12) 0.34065(14) 0.0868(6) Uani 1 1 d . . . . . S1 S 1.000000 1.04524(5) 0.750000 0.0728(3) Uani 1 2 d S T P . . C2 C 0.7877(2) 0.98711(14) 0.54048(17) 0.0580(5) Uani 1 1 d . . . . . O2 O 0.4255(2) 0.71039(10) 0.47147(14) 0.0773(5) Uani 1 1 d . . . . . C3 C 0.6600(3) 0.92971(13) 0.46672(16) 0.0574(5) Uani 1 1 d . . . . . C4 C 0.5920(2) 0.85058(11) 0.51223(15) 0.0523(4) Uani 1 1 d . . . . . C5 C 0.6484(3) 0.82761(14) 0.62845(17) 0.0617(5) Uani 1 1 d . . . . . C6 C 0.7726(3) 0.88630(14) 0.70152(17) 0.0648(5) Uani 1 1 d . . . . . H6 H 0.813(3) 0.8715(16) 0.781(2) 0.085(7) Uiso 1 1 d . . . . . H2 H 0.837(4) 1.0382(17) 0.512(2) 0.084(7) Uiso 1 1 d . . . . . H3 H 0.624(3) 0.9418(14) 0.392(2) 0.062(6) Uiso 1 1 d . . . . . H5 H 0.608(3) 0.7720(16) 0.6574(19) 0.068(6) 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 C1 0.0519(9) 0.0479(9) 0.0645(10) 0.0000(7) 0.0027(7) 0.0034(7) N1 0.0553(9) 0.0573(10) 0.0671(9) -0.0099(7) 0.0071(7) 0.0077(7) O1 0.0939(12) 0.0746(10) 0.0738(10) -0.0078(7) -0.0165(8) 0.0055(8) S1 0.0727(5) 0.0497(5) 0.0813(5) 0.000 -0.0114(4) 0.000 C2 0.0525(10) 0.0509(10) 0.0697(11) 0.0099(8) 0.0123(8) 0.0036(7) O2 0.0812(11) 0.0585(9) 0.0879(10) -0.0079(7) 0.0112(8) -0.0114(7) C3 0.0564(10) 0.0589(10) 0.0540(10) 0.0059(8) 0.0072(7) 0.0081(8) C4 0.0459(9) 0.0485(9) 0.0596(9) -0.0037(7) 0.0069(7) 0.0073(7) C5 0.0658(11) 0.0536(10) 0.0641(11) 0.0058(8) 0.0119(8) -0.0036(8) C6 0.0735(13) 0.0609(11) 0.0546(10) 0.0053(8) 0.0041(8) -0.0055(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2 C1 S1 119.02(14) . . C2 C1 C6 119.29(17) . . C6 C1 S1 121.65(15) . . O1 N1 O2 123.28(16) . . O1 N1 C4 118.49(16) . . O2 N1 C4 118.23(16) . . C1 S1 C1 102.55(12) 2_756 . C1 C2 H2 119.2(16) . . C3 C2 C1 120.77(18) . . C3 C2 H2 120.0(16) . . C2 C3 H3 121.6(14) . . C4 C3 C2 118.61(17) . . C4 C3 H3 119.8(14) . . C3 C4 N1 119.50(16) . . C5 C4 N1 118.71(16) . . C5 C4 C3 121.79(17) . . C4 C5 H5 121.1(14) . . C6 C5 C4 119.11(18) . . C6 C5 H5 119.7(14) . . C1 C6 H6 119.4(14) . . C5 C6 C1 120.40(18) . . C5 C6 H6 120.1(14) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 S1 1.7683(19) . C1 C2 1.383(3) . C1 C6 1.392(3) . N1 O1 1.215(2) . N1 O2 1.223(2) . N1 C4 1.462(2) . C2 C3 1.380(3) . C2 H2 0.90(3) . C3 C4 1.377(3) . C3 H3 0.88(2) . C4 C5 1.376(3) . C5 C6 1.373(3) . C5 H5 0.93(2) . C6 H6 0.94(2) . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 C2 C3 C4 -0.9(3) . . . . N1 C4 C5 C6 -178.13(16) . . . . O1 N1 C4 C3 -15.2(2) . . . . O1 N1 C4 C5 164.44(18) . . . . S1 C1 C2 C3 -177.06(13) . . . . S1 C1 C6 C5 178.37(15) . . . . C2 C1 S1 C1 -138.78(19) . . . 2_756 C2 C1 C6 C5 0.9(3) . . . . C2 C3 C4 N1 179.48(15) . . . . C2 C3 C4 C5 -0.1(3) . . . . O2 N1 C4 C3 165.55(16) . . . . O2 N1 C4 C5 -14.9(2) . . . . C3 C4 C5 C6 1.5(3) . . . . C4 C5 C6 C1 -1.8(3) . . . . C6 C1 S1 C1 43.72(14) . . . 2_756 C6 C1 C2 C3 0.5(3) . . . . _cod_database_fobs_code 3500131