#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221600.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_2221600
loop_
_publ_author_name
'Zia-ur-Rehman, Muhammad'
'Sepehrianazar, Amir'
'Ali, Muhammad'
'Siddiqui, Waseeq Ahmad'
'Çaylak, Nagihan'
_publ_section_title
;
 N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)acetamide
;
_journal_coeditor_code           BT2918
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o941
_journal_paper_doi               10.1107/S1600536809011799
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H12 N2 O6 S'
_chemical_formula_moiety         'C10 H12 N2 O6 S'
_chemical_formula_sum            'C10 H12 N2 O6 S'
_chemical_formula_weight         288.29
_chemical_name_systematic
;
N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)acetamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.769(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1512(2)
_cell_length_b                   15.4303(5)
_cell_length_c                   11.3217(3)
_cell_measurement_reflns_used    3173
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.64
_cell_volume                     1248.70(6)
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14122
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         2101
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2101
_reflns_number_total             3102
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2918.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221600
_cod_database_fobs_code          2221600
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_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 0.23442(8) 0.16533(4) 0.86323(4) 0.03679(18) Uani d . 1 . .
O O1 0.3919(3) 0.43383(14) 0.73036(15) 0.0788(7) Uani d . 1 . .
O O2 0.5342(3) 0.31646(11) 0.76949(14) 0.0535(5) Uani d . 1 . .
O O3 0.0897(2) 0.22746(11) 0.84351(15) 0.0493(4) Uani d . 1 . .
O O4 0.3188(2) 0.12704(11) 0.76361(13) 0.0489(4) Uani d . 1 . .
O O5 0.1853(2) 0.54616(10) 1.10272(14) 0.0473(4) Uani d . 1 . .
O O6 0.6008(3) 0.10620(12) 0.94545(17) 0.0634(5) Uani d . 1 . .
N N1 0.4337(3) 0.37563(12) 0.79726(15) 0.0390(4) Uani d . 1 . .
N N2 0.3979(2) 0.21872(11) 0.94551(14) 0.0353(4) Uani d . 1 . .
C C1 0.3511(3) 0.30400(13) 0.98604(17) 0.0311(4) Uani d . 1 . .
C C2 0.3598(3) 0.37840(13) 0.91680(16) 0.0296(4) Uani d . 1 . .
C C3 0.3029(3) 0.45779(13) 0.95680(17) 0.0334(5) Uani d . 1 . .
H H3 0.3089 0.5064 0.9084 0.040 Uiso calc R 1 . .
C C4 0.2359(3) 0.46491(14) 1.07076(18) 0.0341(5) Uani d . 1 . .
C C5 0.2273(3) 0.39268(15) 1.14165(18) 0.0413(6) Uani d . 1 . .
H H5 0.1845 0.3973 1.2181 0.050 Uiso calc R 1 . .
C C6 0.2828(3) 0.31336(15) 1.09848(18) 0.0393(5) Uani d . 1 . .
H H6 0.2740 0.2647 1.1464 0.047 Uiso calc R 1 . .
C C7 0.1573(4) 0.08423(16) 0.9575(2) 0.0538(7) Uani d . 1 . .
H H7A 0.2552 0.0425 0.9707 0.081 Uiso calc R 1 . .
H H7B 0.0497 0.0561 0.9222 0.081 Uiso calc R 1 . .
H H7C 0.1245 0.1095 1.0316 0.081 Uiso calc R 1 . .
C C8 0.1068(4) 0.55680(17) 1.2166(2) 0.0525(7) Uani d . 1 . .
H H8A 0.0775 0.6168 1.2288 0.079 Uiso calc R 1 . .
H H8B 0.1955 0.5379 1.2766 0.079 Uiso calc R 1 . .
H H8C -0.0053 0.5228 1.2209 0.079 Uiso calc R 1 . .
C C9 0.5736(3) 0.18093(16) 0.97108(19) 0.0431(6) Uani d . 1 . .
C C10 0.7164(4) 0.23869(19) 1.0292(2) 0.0590(7) Uani d . 1 . .
H H10A 0.6632 0.2951 1.0409 0.089 Uiso calc R 1 . .
H H10B 0.8226 0.2436 0.9798 0.089 Uiso calc R 1 . .
H H10C 0.7552 0.2146 1.1042 0.089 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'
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_
_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
O3 S1 O4 . . 118.63(10) ?
O3 S1 N2 . . 104.23(9) ?
O4 S1 N2 . . 109.67(10) ?
O3 S1 C7 . . 109.68(13) ?
O4 S1 C7 . . 109.68(11) ?
N2 S1 C7 . . 103.83(11) ?
C4 O5 C8 . . 117.47(18) ?
O2 N1 O1 . . 122.44(18) ?
O2 N1 C2 . . 119.68(18) ?
O1 N1 C2 . . 117.88(18) ?
C9 N2 C1 . . 121.94(18) ?
C9 N2 S1 . . 120.69(15) ?
C1 N2 S1 . . 117.36(14) ?
C6 C1 C2 . . 117.03(19) ?
C6 C1 N2 . . 118.78(18) ?
C2 C1 N2 . . 124.09(17) ?
C3 C2 C1 . . 122.09(17) ?
C3 C2 N1 . . 116.68(18) ?
C1 C2 N1 . . 121.22(18) ?
C2 C3 C4 . . 119.31(19) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
O5 C4 C5 . . 125.15(19) ?
O5 C4 C3 . . 114.93(19) ?
C5 C4 C3 . . 119.91(19) ?
C4 C5 C6 . . 119.54(19) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C1 . . 122.1(2) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
S1 C7 H7A . . 109.5 ?
S1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
S1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O5 C8 H8A . . 109.5 ?
O5 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O5 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O6 C9 N2 . . 119.8(2) ?
O6 C9 C10 . . 124.3(2) ?
N2 C9 C10 . . 116.0(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 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
S1 O3 . 1.4234(17) ?
S1 O4 . 1.4239(15) ?
S1 N2 . 1.6868(19) ?
S1 C7 . 1.745(2) ?
O1 N1 . 1.207(2) ?
O2 N1 . 1.209(2) ?
O5 C4 . 1.357(2) ?
O5 C8 . 1.432(3) ?
O6 C9 . 1.206(3) ?
N1 C2 . 1.469(2) ?
N2 C9 . 1.407(3) ?
N2 C1 . 1.437(3) ?
C1 C6 . 1.385(3) ?
C1 C2 . 1.393(3) ?
C2 C3 . 1.372(3) ?
C3 C4 . 1.394(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(3) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.493(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10B O3 1_655 0.9600 2.5000 3.453(3) 169.00
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
O3 S1 N2 C9 . . . . -172.42(16) ?
O4 S1 N2 C9 . . . . -44.42(19) ?
C7 S1 N2 C9 . . . . 72.73(18) ?
O3 S1 N2 C1 . . . . 6.58(17) ?
O4 S1 N2 C1 . . . . 134.58(15) ?
C7 S1 N2 C1 . . . . -108.27(16) ?
C9 N2 C1 C6 . . . . -85.2(3) ?
S1 N2 C1 C6 . . . . 95.8(2) ?
C9 N2 C1 C2 . . . . 98.7(2) ?
S1 N2 C1 C2 . . . . -80.3(2) ?
C6 C1 C2 C3 . . . . -0.3(3) ?
N2 C1 C2 C3 . . . . 175.92(19) ?
C6 C1 C2 N1 . . . . 178.73(19) ?
N2 C1 C2 N1 . . . . -5.0(3) ?
O2 N1 C2 C3 . . . . 158.5(2) ?
O1 N1 C2 C3 . . . . -21.0(3) ?
O2 N1 C2 C1 . . . . -20.6(3) ?
O1 N1 C2 C1 . . . . 160.0(2) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
N1 C2 C3 C4 . . . . -178.38(18) ?
C8 O5 C4 C5 . . . . -3.8(3) ?
C8 O5 C4 C3 . . . . 177.00(19) ?
C2 C3 C4 O5 . . . . 179.21(19) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
O5 C4 C5 C6 . . . . 179.9(2) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
C4 C5 C6 C1 . . . . 1.4(4) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
N2 C1 C6 C5 . . . . -177.2(2) ?
C1 N2 C9 O6 . . . . 172.7(2) ?
S1 N2 C9 O6 . . . . -8.3(3) ?
C1 N2 C9 C10 . . . . -7.6(3) ?
S1 N2 C9 C10 . . . . 171.38(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742080
