#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200138.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200138 loop_ _publ_author_name 'Heigel, Erik' 'Bock, Hans' _publ_section_title ; N,N'-m-Phenylenebis(4-nitrobenzenesulfonamide) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o239 _journal_page_last o241 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C18 H14 N4 O8 S2' _chemical_formula_weight 478.45 _chemical_name_common Bis(4-nitrophenylsulfonyl)-1,3-phenylenediamine _chemical_name_systematic ; N,N'-m-Phenylenebis(4-nitrobenzenesulfonamide) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.216(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.8331(10) _cell_length_b 16.4997(14) _cell_length_c 17.3290(13) _cell_measurement_reflns_used 84 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 16.5 _cell_measurement_theta_min 10.0 _cell_volume 1953.7(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .95 _diffrn_measured_fraction_theta_max .95 _diffrn_measurement_device_type 'Siemens P4 four-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .029 _diffrn_reflns_av_sigmaI/netI .029 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 4837 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.35 _diffrn_standards_decay_% <5 _diffrn_standards_interval_count 100 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu .331 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 984 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _refine_diff_density_max .37 _refine_diff_density_min -.43 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 4475 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all .048 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w 1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.4125P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .100 _reflns_number_gt 3740 _reflns_number_total 4475 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6000.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'No' changed to 'no' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (28 times). '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'No' changed to 'no' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (28 times). '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times). '_geom_angle_publ_flag' value 'No' changed to 'no' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (50 times). '_geom_torsion_publ_flag' value 'No' changed to 'no' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (54 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200138 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 -.32458(7) .25662(3) .93385(2) .02220(11) Uani d . 1 . . S S2 .10600(6) .42250(3) .68612(3) .02294(11) Uani d . 1 . . S O1 -.1211(2) .27413(9) .93276(8) .0293(3) Uani d . 1 . . O O2 -.4051(2) .20739(9) .99392(8) .0305(3) Uani d . 1 . . O O3 .1297(2) .42515(9) .76775(8) .0333(3) Uani d . 1 . . O O4 .2620(2) .44533(9) .63621(9) .0338(3) Uani d . 1 . . O O5 -.9518(3) .55828(12) .91301(11) .0532(5) Uani d . 1 . . O O6 -.6896(3) .62090(11) .87738(13) .0567(5) Uani d . 1 . . O O7 -.7032(2) .64062(11) .66215(9) .0430(4) Uani d . 1 . . O O8 -.6555(2) .61775(10) .54221(9) .0384(4) Uani d . 1 . . O N1 -.3843(2) .21082(10) .85445(9) .0229(3) Uani d . 1 . . N H1N -.491(3) .1897(14) .8601(13) .027(6) Uiso d . 1 . . H N2 .0493(2) .33052(9) .66064(9) .0215(3) Uani d . 1 . . N H2N .075(3) .3242(14) .6136(15) .031(6) Uiso d . 1 . . H N3 -.7767(3) .56083(12) .90032(10) .0371(4) Uani d . 1 . . N N4 -.6079(2) .61198(10) .60930(10) .0270(3) Uani d . 1 . . N C1 -.3457(3) .24146(10) .77878(10) .0202(3) Uani d . 1 . . C C2 -.1641(3) .27311(11) .75900(10) .0204(3) Uani d . 1 . . C H2 -.0627 .2781 .7964 .025 Uiso calc R 1 . . H C3 -.1351(3) .29713(10) .68323(10) .0195(3) Uani d . 1 . . C C4 -.2799(3) .28817(12) .62786(10) .0254(4) Uani d . 1 . . C H4 -.2572 .3046 .5761 .030 Uiso calc R 1 . . H C5 -.4570(3) .25516(13) .64853(11) .0305(4) Uani d . 1 . . C H5 -.5562 .2479 .6106 .037 Uiso calc R 1 . . H C6 -.4918(3) .23262(12) .72387(11) .0275(4) Uani d . 1 . . C H6 -.6155 .2111 .7380 .033 Uiso calc R 1 . . H C11 -.4529(3) .34892(11) .93101(10) .0222(3) Uani d . 1 . . C C12 -.3584(3) .41822(12) .90626(10) .0248(4) Uani d . 1 . . C H12 -.2223 .4173 .8952 .030 Uiso calc R 1 . . H C13 -.4648(3) .48886(12) .89790(10) .0267(4) Uani d . 1 . . C H13 -.4033 .5377 .8820 .032 Uiso calc R 1 . . H C14 -.6614(3) .48675(12) .91315(10) .0275(4) Uani d . 1 . . C C15 -.7572(3) .41850(14) .93871(12) .0306(4) Uani d . 1 . . C H15 -.8933 .4198 .9496 .037 Uiso calc R 1 . . H C16 -.6512(3) .34837(13) .94804(11) .0277(4) Uani d . 1 . . C H16 -.7127 .3003 .9659 .033 Uiso calc R 1 . . H C21 -.1015(3) .48244(11) .66381(10) .0210(3) Uani d . 1 . . C C22 -.1549(3) .49172(11) .58719(10) .0234(4) Uani d . 1 . . C H22 -.0787 .4676 .5476 .028 Uiso calc R 1 . . H C23 -.3192(3) .53609(11) .56870(10) .0237(4) Uani d . 1 . . C H23 -.3565 .5445 .5164 .028 Uiso calc R 1 . . H C24 -.4281(3) .56791(11) .62844(10) .0224(4) Uani d . 1 . . C C25 -.3780(3) .55927(12) .70497(11) .0264(4) Uani d . 1 . . C H25 -.4566 .5822 .7444 .032 Uiso calc R 1 . . H C26 -.2103(3) .51636(12) .72283(10) .0257(4) Uani d . 1 . . C H26 -.1700 .5102 .7750 .031 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 .0242(2) .0264(2) .0161(2) .00276(17) .00192(15) .00390(16) S2 .0193(2) .0267(2) .0228(2) -.00306(17) -.00059(16) -.00095(17) O1 .0255(7) .0382(8) .0241(7) .0045(6) -.0015(5) .0031(6) O2 .0388(8) .0340(8) .0187(6) .0037(6) .0050(5) .0086(5) O3 .0365(8) .0392(8) .0240(7) .0019(6) -.0101(6) -.0062(6) O4 .0217(7) .0358(8) .0439(9) -.0064(6) .0056(6) .0015(6) O5 .0449(10) .0625(12) .0522(11) .0282(9) .0103(8) .0072(9) O6 .0594(12) .0386(10) .0720(13) .0157(9) -.0004(10) .0150(9) O7 .0402(9) .0529(10) .0361(8) .0207(8) .0018(7) -.0088(7) O8 .0438(9) .0418(9) .0295(8) .0106(7) -.0097(6) -.0008(6) N1 .0265(8) .0241(8) .0182(7) -.0035(6) .0047(6) .0026(6) N2 .0217(7) .0253(8) .0176(7) -.0008(6) .0047(6) -.0015(6) N3 .0434(11) .0406(11) .0272(9) .0173(9) -.0005(8) .0008(8) N4 .0286(8) .0236(8) .0287(8) .0014(6) -.0012(6) -.0015(6) C1 .0262(9) .0174(8) .0170(8) .0012(7) .0035(6) .0019(6) C2 .0223(8) .0219(8) .0171(8) .0011(7) -.0004(6) .0004(6) C3 .0209(8) .0181(8) .0194(8) -.0009(6) .0038(6) -.0010(6) C4 .0306(10) .0287(9) .0168(8) -.0035(8) .0006(7) .0029(7) C5 .0301(10) .0384(11) .0228(9) -.0086(8) -.0046(7) .0031(8) C6 .0259(9) .0320(10) .0245(9) -.0077(8) .0004(7) .0041(8) C11 .0242(9) .0268(9) .0158(8) .0018(7) -.0007(6) -.0010(7) C12 .0224(9) .0314(10) .0205(8) .0002(7) -.0002(7) .0007(7) C13 .0336(10) .0269(9) .0196(8) .0013(8) -.0012(7) .0008(7) C14 .0330(10) .0331(10) .0165(8) .0108(8) -.0030(7) -.0026(7) C15 .0228(9) .0418(12) .0271(10) .0054(8) .0000(7) -.0010(8) C16 .0238(9) .0331(10) .0261(9) -.0009(8) .0024(7) .0006(8) C21 .0205(8) .0205(8) .0222(8) -.0032(6) .0010(6) .0005(6) C22 .0241(9) .0276(9) .0185(8) -.0022(7) .0040(7) -.0013(7) C23 .0276(9) .0250(9) .0185(8) -.0040(7) .0000(7) .0000(7) C24 .0238(9) .0194(8) .0239(9) -.0022(7) .0003(7) -.0002(7) C25 .0291(10) .0295(10) .0208(8) .0004(8) .0054(7) -.0022(7) C26 .0287(10) .0296(10) .0186(8) -.0005(8) .0019(7) -.0002(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 . 1.4206(15) no S1 O2 . 1.4320(14) no S1 N1 . 1.621(2) yes S1 C11 . 1.7577(19) no S2 O3 . 1.4238(14) no S2 O4 . 1.4260(15) no S2 N2 . 1.627(2) yes S2 C21 . 1.7703(19) no O5 N3 . 1.218(3) no O6 N3 . 1.223(3) no O7 N4 . 1.221(2) no O8 N4 . 1.210(2) no N1 C1 . 1.431(2) yes N2 C3 . 1.431(2) yes N3 C14 . 1.471(3) yes N4 C24 . 1.464(2) yes C1 C6 . 1.384(3) no C1 C2 . 1.390(2) no C2 C3 . 1.386(2) no C3 C4 . 1.383(3) no C4 C5 . 1.376(3) no C5 C6 . 1.379(3) no C11 C12 . 1.382(3) no C11 C16 . 1.388(3) no C12 C13 . 1.381(3) no C13 C14 . 1.371(3) no C14 C15 . 1.377(3) no C15 C16 . 1.374(3) no C21 C22 . 1.384(2) no C21 C26 . 1.385(2) no C22 C23 . 1.377(3) no C23 C24 . 1.381(3) no C24 C25 . 1.376(3) no C25 C26 . 1.381(3) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 '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_publ_flag O1 S1 O2 120.27(9) no O1 S1 N1 109.10(9) no O2 S1 N1 104.86(9) no O1 S1 C11 108.15(9) no O2 S1 C11 108.59(9) no N1 S1 C11 104.85(8) no O3 S2 O4 120.79(9) no O3 S2 N2 108.92(9) no O4 S2 N2 105.05(9) no O3 S2 C21 106.72(9) no O4 S2 C21 108.66(9) no N2 S2 C21 105.80(8) no C1 N1 S1 124.50(13) no C3 N2 S2 119.59(12) no O5 N3 O6 124.5(2) no O5 N3 C14 118.0(2) no O6 N3 C14 117.49(19) no O8 N4 O7 123.23(17) no O8 N4 C24 118.63(16) no O7 N4 C24 118.14(16) no C6 C1 C2 120.80(16) no C6 C1 N1 117.22(16) no C2 C1 N1 121.79(16) no C3 C2 C1 118.15(16) no C4 C3 C2 121.46(16) no C4 C3 N2 118.66(16) no C2 C3 N2 119.88(16) no C5 C4 C3 119.29(17) no C4 C5 C6 120.53(18) no C5 C6 C1 119.73(18) no C12 C11 C16 121.93(18) no C12 C11 S1 119.47(14) no C16 C11 S1 118.40(15) no C13 C12 C11 118.97(18) no C14 C13 C12 118.32(19) no C13 C14 C15 123.40(19) no C13 C14 N3 118.33(19) no C15 C14 N3 118.26(19) no C16 C15 C14 118.39(18) no C15 C16 C11 118.95(19) no C22 C21 C26 121.57(17) no C22 C21 S2 118.64(14) no C26 C21 S2 119.75(14) no C23 C22 C21 119.59(16) no C22 C23 C24 117.96(17) no C25 C24 C23 123.40(18) no C25 C24 N4 118.37(16) no C23 C24 N4 118.22(16) no C24 C25 C26 118.18(17) no C25 C26 C21 119.27(17) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2N O2 4_665 .84(2) 2.14(3) 2.974(2) 169(2) yes N1 H1N O7 2_346 .81(2) 2.27(2) 3.060(2) 163(2) yes C6 H6 O7 2_346 .95 2.43 3.253(2) 145 yes C4 H4 O8 3_466 .95 2.49 3.359(2) 152 yes 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_publ_flag O1 S1 N1 C1 -54.38(17) no O2 S1 N1 C1 175.56(15) no C11 S1 N1 C1 61.3(2) yes O3 S2 N2 C3 66.88(15) no O4 S2 N2 C3 -162.39(14) no C21 S2 N2 C3 -47.5(2) yes S1 N1 C1 C6 -138.9(2) yes S1 N1 C1 C2 46.0(2) no C6 C1 C2 C3 1.4(3) no N1 C1 C2 C3 176.26(16) no C1 C2 C3 C4 -1.7(3) no C1 C2 C3 N2 179.58(16) no S2 N2 C3 C4 106.8(2) yes S2 N2 C3 C2 -74.5(2) no C2 C3 C4 C5 .4(3) no N2 C3 C4 C5 179.15(18) no C3 C4 C5 C6 1.2(3) no C4 C5 C6 C1 -1.6(3) no C2 C1 C6 C5 .2(3) no N1 C1 C6 C5 -174.90(18) no O1 S1 C11 C12 18.60(17) no O2 S1 C11 C12 150.65(15) no N1 S1 C11 C12 -97.7(2) yes O1 S1 C11 C16 -166.44(14) no O2 S1 C11 C16 -34.39(17) no N1 S1 C11 C16 77.26(16) no C16 C11 C12 C13 -.3(3) no S1 C11 C12 C13 174.45(14) no C11 C12 C13 C14 -1.3(3) no C12 C13 C14 C15 2.1(3) no C12 C13 C14 N3 -176.83(17) no O5 N3 C14 C13 179.05(19) no O6 N3 C14 C13 -.8(3) no O5 N3 C14 C15 .1(3) no O6 N3 C14 C15 -179.8(2) no C13 C14 C15 C16 -1.3(3) no N3 C14 C15 C16 177.65(17) no C14 C15 C16 C11 -.4(3) no C12 C11 C16 C15 1.1(3) no S1 C11 C16 C15 -173.69(15) no O3 S2 C21 C22 178.51(15) no O4 S2 C21 C22 46.78(17) no N2 S2 C21 C22 -65.6(2) yes O3 S2 C21 C26 -3.79(18) no O4 S2 C21 C26 -135.52(16) no N2 S2 C21 C26 112.12(16) no C26 C21 C22 C23 .4(3) no S2 C21 C22 C23 178.06(14) no C21 C22 C23 C24 -1.8(3) no C22 C23 C24 C25 1.7(3) no C22 C23 C24 N4 -177.25(16) no O8 N4 C24 C25 -177.91(18) no O7 N4 C24 C25 1.5(3) no O8 N4 C24 C23 1.1(3) no O7 N4 C24 C23 -179.44(18) no C23 C24 C25 C26 -.1(3) no N4 C24 C25 C26 178.81(17) no C24 C25 C26 C21 -1.3(3) no C22 C21 C26 C25 1.2(3) no S2 C21 C26 C25 -176.44(15) no _cod_database_fobs_code 2200138 _journal_paper_doi 10.1107/S1600536801001775