#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/51/2015170.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_2015170
loop_
_publ_author_name
'Košutić Hulita, Nada'
'Danilovski, Aleksandar'
'Filić, Darko'
'Marinković, Marina'
'Meštrović, Ernest'
'Dumić, Miljenko'
_publ_section_title
;
 Supramolecular structures of three isomeric
 4-(methylphenylamino)pyridine-3-sulfonamides
;
_journal_coeditor_code           JZ1757
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o648
_journal_page_last               o651
_journal_paper_doi               10.1107/S0108270105031902
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H13 N3 O2 S'
_chemical_formula_moiety         'C12 H13 N3 O2 S'
_chemical_formula_sum            'C12 H13 N3 O2 S'
_chemical_formula_weight         263.31
_chemical_name_systematic
;
4-(2-methylanilino)pyridine-3-sulfonamide
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.714(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5118(7)
_cell_length_b                   7.2369(13)
_cell_length_c                   21.181(5)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.7
_cell_measurement_theta_min      8.1
_cell_volume                     1295.8(4)
_computing_cell_refinement       STADI4
_computing_data_collection       'STADI4 (Stoe & Cie, 1996)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1996)'
_computing_molecular_graphics
'PLATON2000 (Spek, 2003) and WebLab ViewerPro (Accelrys, 2000)'
_computing_publication_material  'SHELXL97 and PARST96 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Philips PW1100, updated by Stoe'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0005
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7502
_diffrn_reflns_theta_full        29.95
_diffrn_reflns_theta_max         29.95
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        4.2
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0592P)²+0.4643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                2396
_reflns_number_total             3751
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1757.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015170
_cod_database_fobs_code          2015170
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
N1 0.6113(2) 0.4532(3) 0.19545(9) 0.0529(5) Uani d . 1 . . N
C2 0.7662(2) 0.4715(3) 0.21237(9) 0.0416(4) Uani d . 1 . . C
H2 0.8090 0.4190 0.2506 0.050 Uiso calc R 1 . . H
C3 0.86740(19) 0.5634(2) 0.17668(8) 0.0330(3) Uani d . 1 . . C
C4 0.8080(2) 0.6439(3) 0.11770(9) 0.0353(4) Uani d . 1 . . C
C5 0.6437(2) 0.6247(3) 0.10094(10) 0.0495(5) Uani d . 1 . . C
H5 0.5961 0.6754 0.0631 0.059 Uiso calc R 1 . . H
C6 0.5544(2) 0.5320(3) 0.13996(12) 0.0561(6) Uani d . 1 . . C
H6 0.4464 0.5225 0.1273 0.067 Uiso calc R 1 . . H
S31 1.06857(5) 0.57920(7) 0.20629(2) 0.03636(13) Uani d . 1 . . S
O32 1.16523(16) 0.5336(2) 0.15706(7) 0.0492(4) Uani d . 1 . . O
O33 1.09061(18) 0.4710(3) 0.26349(7) 0.0602(4) Uani d . 1 . . O
N34 1.0888(2) 0.7967(3) 0.21814(9) 0.0472(4) Uani d . 1 . . N
H342 1.189(3) 0.834(4) 0.2218(12) 0.066(8) Uiso d . 1 . . H
H341 1.033(3) 0.840(4) 0.2481(13) 0.071(8) Uiso d . 1 . . H
N4 0.89991(19) 0.7320(3) 0.07944(8) 0.0429(4) Uani d . 1 . . N
H4 0.991(3) 0.738(3) 0.0914(11) 0.052(7) Uiso d . 1 . . H
C41 0.8353(2) 0.8420(3) 0.02616(9) 0.0399(4) Uani d . 1 . . C
C42 0.7811(3) 1.0192(3) 0.03619(10) 0.0481(5) Uani d . 1 . . C
C43 0.7196(3) 1.1207(3) -0.01762(11) 0.0569(6) Uani d . 1 . . C
H43 0.6835 1.2404 -0.0124 0.068 Uiso calc R 1 . . H
C44 0.7113(3) 1.0482(4) -0.07740(11) 0.0581(6) Uani d . 1 . . C
H44 0.6691 1.1179 -0.1122 0.070 Uiso calc R 1 . . H
C45 0.7657(3) 0.8718(4) -0.08625(11) 0.0619(6) Uani d . 1 . . C
H45 0.7598 0.8220 -0.1269 0.074 Uiso calc R 1 . . H
C46 0.8288(3) 0.7692(3) -0.03436(10) 0.0532(5) Uani d . 1 . . C
H46 0.8670 0.6507 -0.0402 0.064 Uiso calc R 1 . . H
C421 0.7854(4) 1.0996(4) 0.10168(12) 0.0782(9) Uani d . 1 . . C
H421 0.6969 1.0543 0.1214 0.117 Uiso calc R 1 . . H
H422 0.7800 1.2318 0.0989 0.117 Uiso calc R 1 . . H
H423 0.8820 1.0640 0.1267 0.117 Uiso calc R 1 . . H
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 8
-4 0 2
4 1 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C6 115.94(17)
N1 C2 C3 124.14(18)
N1 C2 H2 117.9
C3 C2 H2 117.9
C2 C3 C4 119.97(16)
C2 C3 S31 118.67(14)
C4 C3 S31 121.35(13)
N4 C4 C5 121.52(17)
N4 C4 C3 123.45(16)
C5 C4 C3 115.03(16)
C6 C5 C4 120.21(18)
C6 C5 H5 119.9
C4 C5 H5 119.9
N1 C6 C5 124.69(18)
N1 C6 H6 117.7
C5 C6 H6 117.7
O33 S31 O32 117.16(10)
O33 S31 N34 113.75(11)
O32 S31 N34 106.21(10)
O33 S31 C3 106.94(9)
O32 S31 C3 110.00(8)
N34 S31 C3 101.68(9)
S31 N34 H342 113.4(17)
S31 N34 H341 113.6(18)
H342 N34 H341 115(2)
C4 N4 C41 122.54(16)
C4 N4 H4 116.7(17)
C41 N4 H4 119.6(18)
C46 C41 C42 121.12(18)
C46 C41 N4 119.19(19)
C42 C41 N4 119.69(18)
C41 C42 C43 117.26(19)
C41 C42 C421 121.8(2)
C43 C42 C421 120.9(2)
C44 C43 C42 121.7(2)
C44 C43 H43 119.1
C42 C43 H43 119.1
C43 C44 C45 120.0(2)
C43 C44 H44 120.0
C45 C44 H44 120.0
C44 C45 C46 119.7(2)
C44 C45 H45 120.2
C46 C45 H45 120.2
C41 C46 C45 120.2(2)
C41 C46 H46 119.9
C45 C46 H46 119.9
C42 C421 H421 109.5
C42 C421 H422 109.5
H421 C421 H422 109.5
C42 C421 H423 109.5
H421 C421 H423 109.5
H422 C421 H423 109.5
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
N1 C2 . 1.332(2) ?
N1 C6 . 1.344(3) ?
C2 C3 . 1.381(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.417(2) ?
C3 S31 . 1.7571(17) ?
C4 N4 . 1.350(2) ?
C4 C5 . 1.409(2) ?
C5 C6 . 1.363(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
S31 O33 . 1.4363(16) ?
S31 O32 . 1.4401(14) ?
S31 N34 . 1.5997(19) ?
N34 H342 . 0.89(3) ?
N34 H341 . 0.89(3) ?
N4 C41 . 1.437(2) ?
N4 H4 . 0.79(2) ?
C41 C46 . 1.381(3) ?
C41 C42 . 1.387(3) ?
C42 C43 . 1.405(3) ?
C42 C421 . 1.501(3) ?
C43 C44 . 1.365(3) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.378(4) ?
C44 H44 . 0.9300 ?
C45 C46 . 1.382(3) ?
C45 H45 . 0.9300 ?
C46 H46 . 0.9300 ?
C421 H421 . 0.9600 ?
C421 H422 . 0.9600 ?
C421 H423 . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_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
N4 H4 O32 1 1 0.79(3) 2.42(2) 3.000(2) 132(2) yes
N34 H342 O33 1 2_755 0.91(3) 2.10(3) 2.990(2) 169(3) yes
N34 H341 N1 1 2_655 0.86(3) 2.00(3) 2.875(3) 172(3) yes
C2 H2 O33 1 1 0.93 2.41 2.845(2) 108.5 yes
C6 H6 O32 1 1_455 0.93 2.55 3.374(2) 148.4 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
C6 N1 C2 C3 -0.3(3)
N1 C2 C3 C4 -0.7(3)
N1 C2 C3 S31 178.81(17)
C2 C3 C4 N4 -178.36(19)
S31 C3 C4 N4 2.1(3)
C2 C3 C4 C5 1.2(3)
S31 C3 C4 C5 -178.26(15)
N4 C4 C5 C6 178.8(2)
C3 C4 C5 C6 -0.8(3)
C2 N1 C6 C5 0.7(4)
C4 C5 C6 N1 -0.1(4)
C2 C3 S31 O33 5.25(18)
C4 C3 S31 O33 -175.25(15)
C2 C3 S31 O32 133.47(16)
C4 C3 S31 O32 -47.03(17)
C2 C3 S31 N34 -114.28(16)
C4 C3 S31 N34 65.22(17)
C5 C4 N4 C41 12.4(3)
C3 C4 N4 C41 -168.01(18)
C4 N4 C41 C46 -101.8(2)
C4 N4 C41 C42 78.3(3)
C46 C41 C42 C43 0.0(3)
N4 C41 C42 C43 179.8(2)
C46 C41 C42 C421 179.2(2)
N4 C41 C42 C421 -1.0(3)
C41 C42 C43 C44 0.8(4)
C421 C42 C43 C44 -178.4(3)
C42 C43 C44 C45 -0.7(4)
C43 C44 C45 C46 -0.2(4)
C42 C41 C46 C45 -0.8(3)
N4 C41 C46 C45 179.3(2)
C44 C45 C46 C41 0.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133708
