#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222630.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_2222630
loop_
_publ_author_name
'Zhang, Guo-Yao'
'Qian, Shan'
'Li, Xiao-Cen'
'Wu, Yong'
_publ_section_title
;
 N-(2,5-Dimethoxyphenyl)-4-nitrobenzenesulfonamide
;
_journal_coeditor_code           CI2846
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1939
_journal_paper_doi               10.1107/S1600536809027962
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 N2 O6 S'
_chemical_formula_moiety         'C14 H14 N2 O6 S'
_chemical_formula_sum            'C14 H14 N2 O6 S'
_chemical_formula_weight         338.33
_chemical_name_systematic
;
N-(2,5-Dimethoxyphenyl)-4-nitrobenzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.532(4)
_cell_length_b                   12.375(4)
_cell_length_c                   17.311(4)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      7.53
_cell_measurement_theta_min      4.30
_cell_volume                     3113.1(15)
_computing_cell_refinement       'DIFRAC (Gabe & White, 1993)'
_computing_data_collection       'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0044
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4003
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0.884
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9057
_exptl_absorpt_correction_T_min  0.8933
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '(WinGX; Farrugia, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0398
_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)+(0.0632P)²+0.3387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                1790
_reflns_number_total             2877
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2846.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3113.2(14)
_cod_database_code               2222630
_cod_database_fobs_code          2222630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
S S1 0.06666(4) 0.69183(6) 0.38224(3) 0.0473(2) Uani d . 1 . .
N N1 0.05816(14) 0.7151(2) 0.28983(13) 0.0530(6) Uani d . 1 . .
H H1N 0.0834(18) 0.669(2) 0.2672(16) 0.057(10) Uiso d . 1 . .
N N2 -0.23262(16) 0.3748(2) 0.44664(14) 0.0662(7) Uani d . 1 . .
O O1 -0.20633(15) 0.94720(18) 0.27633(11) 0.0854(7) Uani d . 1 . .
O O2 0.00947(13) 0.61834(17) 0.16246(10) 0.0731(6) Uani d . 1 . .
O O3 0.15329(11) 0.63919(17) 0.39190(10) 0.0624(5) Uani d . 1 . .
O O4 0.04683(13) 0.78981(14) 0.42213(10) 0.0615(5) Uani d . 1 . .
O O5 -0.30528(13) 0.40717(19) 0.47199(13) 0.0831(7) Uani d . 1 . .
O O6 -0.21642(16) 0.28124(19) 0.43150(18) 0.1057(9) Uani d . 1 . .
C C1 -0.02551(15) 0.7501(2) 0.25371(14) 0.0452(6) Uani d . 1 . .
C C2 -0.07889(17) 0.8326(2) 0.28188(15) 0.0549(7) Uani d . 1 . .
H H2 -0.0618 0.8681 0.3270 0.066 Uiso calc R 1 . .
C C3 -0.15884(18) 0.8634(2) 0.24300(15) 0.0569(7) Uani d . 1 . .
C C4 -0.18336(17) 0.8124(2) 0.17588(15) 0.0562(7) Uani d . 1 . .
H H4 -0.2366 0.8329 0.1499 0.067 Uiso calc R 1 . .
C C5 -0.12900(19) 0.7305(2) 0.14695(15) 0.0576(7) Uani d . 1 . .
H H5 -0.1456 0.6966 0.1011 0.069 Uiso calc R 1 . .
C C6 -0.04991(17) 0.6982(2) 0.18527(14) 0.0495(6) Uani d . 1 . .
C C7 -0.2851(2) 0.9874(3) 0.23675(18) 0.0916(11) Uani d . 1 . .
H H7A -0.2688 1.0047 0.1844 0.137 Uiso calc R 1 . .
H H7B -0.3071 1.0512 0.2623 0.137 Uiso calc R 1 . .
H H7C -0.3325 0.9334 0.2368 0.137 Uiso calc R 1 . .
C C8 -0.0013(2) 0.5726(3) 0.08822(16) 0.0856(11) Uani d . 1 . .
H H8A -0.0571 0.5312 0.0866 0.128 Uiso calc R 1 . .
H H8B 0.0501 0.5263 0.0772 0.128 Uiso calc R 1 . .
H H8C -0.0041 0.6292 0.0504 0.128 Uiso calc R 1 . .
C C9 -0.02178(15) 0.59843(19) 0.40462(12) 0.0392(5) Uani d . 1 . .
C C10 -0.00660(16) 0.4902(2) 0.39088(14) 0.0518(6) Uani d . 1 . .
H H10 0.0498 0.4670 0.3716 0.062 Uiso calc R 1 . .
C C11 -0.07563(18) 0.4167(2) 0.40591(15) 0.0542(7) Uani d . 1 . .
H H11 -0.0664 0.3432 0.3978 0.065 Uiso calc R 1 . .
C C12 -0.15815(16) 0.4544(2) 0.43310(14) 0.0474(6) Uani d . 1 . .
C C13 -0.17421(17) 0.5610(2) 0.44706(15) 0.0536(7) Uani d . 1 . .
H H13 -0.2310 0.5838 0.4657 0.064 Uiso calc R 1 . .
C C14 -0.10508(15) 0.6342(2) 0.43313(15) 0.0494(6) Uani d . 1 . .
H H14 -0.1144 0.7073 0.4428 0.059 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 S1 O3 . . 120.67(12) ?
O4 S1 N1 . . 108.06(13) ?
O3 S1 N1 . . 105.22(11) ?
O4 S1 C9 . . 107.61(11) ?
O3 S1 C9 . . 108.45(11) ?
N1 S1 C9 . . 105.95(11) ?
C1 N1 S1 . . 123.06(17) ?
C1 N1 H1N . . 114(2) ?
S1 N1 H1N . . 109(2) ?
O6 N2 O5 . . 124.4(3) ?
O6 N2 C12 . . 117.4(3) ?
O5 N2 C12 . . 118.3(3) ?
C3 O1 C7 . . 117.8(2) ?
C6 O2 C8 . . 118.8(2) ?
C2 C1 C6 . . 120.1(2) ?
C2 C1 N1 . . 123.3(2) ?
C6 C1 N1 . . 116.6(2) ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 O1 . . 125.0(2) ?
C4 C3 C2 . . 120.0(3) ?
O1 C3 C2 . . 115.0(2) ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.9(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
O2 C6 C5 . . 126.3(2) ?
O2 C6 C1 . . 114.7(2) ?
C5 C6 C1 . . 119.0(2) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C14 . . 120.9(2) ?
C10 C9 S1 . . 118.70(18) ?
C14 C9 S1 . . 120.34(19) ?
C9 C10 C11 . . 119.5(2) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C12 C11 C10 . . 118.4(2) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C13 C12 C11 . . 122.8(2) ?
C13 C12 N2 . . 119.4(2) ?
C11 C12 N2 . . 117.8(2) ?
C12 C13 C14 . . 118.9(2) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C13 C14 C9 . . 119.5(2) ?
C13 C14 H14 . . 120.3 ?
C9 C14 H14 . . 120.3 ?
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 O4 . 1.4249(19) ?
S1 O3 . 1.4273(18) ?
S1 N1 . 1.630(2) ?
S1 C9 . 1.771(2) ?
N1 C1 . 1.434(3) ?
N1 H1N . 0.78(3) ?
N2 O6 . 1.210(3) ?
N2 O5 . 1.212(3) ?
N2 C12 . 1.482(3) ?
O1 C3 . 1.373(3) ?
O1 C7 . 1.424(3) ?
O2 C6 . 1.370(3) ?
O2 C8 . 1.413(3) ?
C1 C2 . 1.372(3) ?
C1 C6 . 1.393(3) ?
C2 C3 . 1.396(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.370(4) ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.93 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C10 . 1.378(4) ?
C9 C14 . 1.380(3) ?
C10 C11 . 1.379(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.371(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.360(3) ?
C13 C14 . 1.374(3) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
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
N1 H1N O2 . 0.78(3) 2.20(3) 2.607(3) 113(2)
C8 H8C O4 8_575 0.96 2.55 3.414(4) 150
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 S1 N1 C1 . . . . -61.0(2) ?
O3 S1 N1 C1 . . . . 168.9(2) ?
C9 S1 N1 C1 . . . . 54.1(2) ?
S1 N1 C1 C2 . . . . 47.4(3) ?
S1 N1 C1 C6 . . . . -134.8(2) ?
C6 C1 C2 C3 . . . . 1.3(4) ?
N1 C1 C2 C3 . . . . 179.0(2) ?
C7 O1 C3 C4 . . . . -2.7(4) ?
C7 O1 C3 C2 . . . . 175.8(3) ?
C1 C2 C3 C4 . . . . -1.0(4) ?
C1 C2 C3 O1 . . . . -179.7(2) ?
O1 C3 C4 C5 . . . . 178.6(2) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C8 O2 C6 C5 . . . . 9.4(4) ?
C8 O2 C6 C1 . . . . -170.3(2) ?
C4 C5 C6 O2 . . . . -180.0(2) ?
C4 C5 C6 C1 . . . . -0.3(4) ?
C2 C1 C6 O2 . . . . 179.1(2) ?
N1 C1 C6 O2 . . . . 1.2(3) ?
C2 C1 C6 C5 . . . . -0.7(4) ?
N1 C1 C6 C5 . . . . -178.5(2) ?
O4 S1 C9 C10 . . . . -162.61(19) ?
O3 S1 C9 C10 . . . . -30.5(2) ?
N1 S1 C9 C10 . . . . 82.0(2) ?
O4 S1 C9 C14 . . . . 19.3(2) ?
O3 S1 C9 C14 . . . . 151.32(19) ?
N1 S1 C9 C14 . . . . -96.1(2) ?
C14 C9 C10 C11 . . . . -0.1(4) ?
S1 C9 C10 C11 . . . . -178.18(19) ?
C9 C10 C11 C12 . . . . 1.0(4) ?
C10 C11 C12 C13 . . . . -1.1(4) ?
C10 C11 C12 N2 . . . . 178.1(2) ?
O6 N2 C12 C13 . . . . 178.0(3) ?
O5 N2 C12 C13 . . . . -2.0(4) ?
O6 N2 C12 C11 . . . . -1.3(4) ?
O5 N2 C12 C11 . . . . 178.7(2) ?
C11 C12 C13 C14 . . . . 0.2(4) ?
N2 C12 C13 C14 . . . . -179.0(2) ?
C12 C13 C14 C9 . . . . 0.7(4) ?
C10 C9 C14 C13 . . . . -0.8(4) ?
S1 C9 C14 C13 . . . . 177.25(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 648322
