#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210495.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_2210495
loop_
_publ_author_name
'Wu, Ya'
_publ_section_title
;
 1-Benzenesulfonyl-5-chloro-2,4-dimethoxybenzene
;
_journal_coeditor_code           BH2042
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4272
_journal_page_last               o4273
_journal_paper_doi               10.1107/S1600536806034647
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 Cl O4 S'
_chemical_formula_moiety         'C14 H13 Cl O4 S'
_chemical_formula_sum            'C14 H13 Cl O4 S'
_chemical_formula_weight         312.75
_chemical_name_systematic
;
1-Benzenesulfonyl-5-chloro-2,4-dimethoxybenzene
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.3423(16)
_cell_length_b                   19.487(4)
_cell_length_c                   20.022(4)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.65
_cell_measurement_theta_min      2.32
_cell_volume                     2864.7(10)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART-1000 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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15348
_diffrn_reflns_theta_full        26.57
_diffrn_reflns_theta_max         26.57
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.9205
_exptl_absorpt_correction_T_min  0.8983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0819
_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)+(0.0452P)²+0.9214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                1860
_reflns_number_total             2981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2042.cif
_cod_data_source_block           I
_cod_database_code               2210495
_cod_database_fobs_code          2210495
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x+1/2, -y, z+1/2'
'x-1/2, y, -z-1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
S S1 0.74621(9) 0.06892(3) 0.41420(3) 0.04242(18) Uani d . 1
Cl Cl1 0.92833(12) -0.16835(3) 0.29332(4) 0.0665(3) Uani d . 1
O O1 0.7704(3) 0.02060(9) 0.46753(8) 0.0578(5) Uani d . 1
O O2 0.5713(2) 0.10069(10) 0.40637(8) 0.0559(5) Uani d . 1
O O3 0.7602(2) 0.12496(8) 0.27749(7) 0.0472(5) Uani d . 1
O O4 0.8868(2) -0.09224(8) 0.17075(8) 0.0520(5) Uani d . 1
C C1 0.9083(3) 0.13456(12) 0.42414(11) 0.0410(6) Uani d . 1
C C2 1.0727(4) 0.11938(14) 0.45485(12) 0.0523(7) Uani d . 1
H H2 1.0968 0.0752 0.4700 0.063 Uiso calc R 1
C C3 1.2003(4) 0.17106(18) 0.46257(15) 0.0677(9) Uani d . 1
H H3 1.3104 0.1620 0.4837 0.081 Uiso calc R 1
C C4 1.1639(5) 0.23599(17) 0.43894(16) 0.0746(9) Uani d . 1
H H4 1.2509 0.2703 0.4436 0.090 Uiso calc R 1
C C5 1.0010(5) 0.25072(15) 0.40856(14) 0.0648(8) Uani d . 1
H H5 0.9780 0.2948 0.3929 0.078 Uiso calc R 1
C C6 0.8715(4) 0.20004(13) 0.40123(12) 0.0504(7) Uani d . 1
H H6 0.7604 0.2098 0.3811 0.061 Uiso calc R 1
C C7 0.8022(3) 0.02489(11) 0.34001(11) 0.0373(6) Uani d . 1
C C8 0.7948(3) 0.05660(11) 0.27752(11) 0.0356(5) Uani d . 1
C C9 0.8236(3) 0.01836(11) 0.22011(11) 0.0374(6) Uani d . 1
H H9 0.8180 0.0395 0.1785 0.045 Uiso calc R 1
C C10 0.8606(3) -0.05105(12) 0.22430(11) 0.0392(6) Uani d . 1
C C11 0.8742(3) -0.08203(11) 0.28706(12) 0.0410(6) Uani d . 1
C C12 0.8438(3) -0.04436(12) 0.34382(11) 0.0402(6) Uani d . 1
H H12 0.8511 -0.0655 0.3854 0.048 Uiso calc R 1
C C13 0.7655(4) 0.16126(13) 0.21577(12) 0.0519(7) Uani d . 1
H H13A 0.8809 0.1537 0.1945 0.078 Uiso calc R 1
H H13B 0.7495 0.2094 0.2240 0.078 Uiso calc R 1
H H13C 0.6696 0.1451 0.1872 0.078 Uiso calc R 1
C C14 0.8444(4) -0.06548(13) 0.10585(12) 0.0545(7) Uani d . 1
H H14A 0.7218 -0.0484 0.1057 0.082 Uiso calc R 1
H H14B 0.8560 -0.1013 0.0732 0.082 Uiso calc R 1
H H14C 0.9270 -0.0289 0.0952 0.082 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O2 S1 O1 118.38(11) yes
O2 S1 C1 107.73(12) yes
O1 S1 C1 108.03(11) yes
O2 S1 C7 109.06(11) yes
O1 S1 C7 106.18(11) yes
C1 S1 C7 106.94(11) yes
C8 O3 C13 118.89(17) ?
C10 O4 C14 118.11(19) ?
C6 C1 C2 120.9(2) ?
C6 C1 S1 120.1(2) ?
C2 C1 S1 119.0(2) ?
C3 C2 C1 118.9(3) ?
C3 C2 H2 120.6 ?
C1 C2 H2 120.6 ?
C4 C3 C2 119.9(3) ?
C4 C3 H3 120.0 ?
C2 C3 H3 120.0 ?
C5 C4 C3 120.9(3) ?
C5 C4 H4 119.5 ?
C3 C4 H4 119.5 ?
C4 C5 C6 119.9(3) ?
C4 C5 H5 120.1 ?
C6 C5 H5 120.1 ?
C5 C6 C1 119.4(3) ?
C5 C6 H6 120.3 ?
C1 C6 H6 120.3 ?
C12 C7 C8 119.3(2) ?
C12 C7 S1 118.61(17) ?
C8 C7 S1 122.01(17) ?
O3 C8 C9 123.80(19) ?
O3 C8 C7 116.26(19) ?
C9 C8 C7 119.9(2) ?
C10 C9 C8 120.4(2) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
O4 C10 C9 124.1(2) ?
O4 C10 C11 116.5(2) ?
C9 C10 C11 119.4(2) ?
C12 C11 C10 120.1(2) ?
C12 C11 Cl1 119.80(18) ?
C10 C11 Cl1 120.05(18) ?
C11 C12 C7 120.8(2) ?
C11 C12 H12 119.6 ?
C7 C12 H12 119.6 ?
O3 C13 H13A 109.5 ?
O3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 H14A 109.5 ?
O4 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O4 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.4342(19) yes
S1 O1 1.4348(17) yes
S1 C1 1.758(3) yes
S1 C7 1.764(2) yes
Cl1 C11 1.733(2) ?
O3 C8 1.356(3) ?
O3 C13 1.424(3) ?
O4 C10 1.353(3) ?
O4 C14 1.434(3) ?
C1 C6 1.383(3) ?
C1 C2 1.387(3) ?
C2 C3 1.384(4) ?
C2 H2 0.9300 ?
C3 C4 1.377(4) ?
C3 H3 0.9300 ?
C4 C5 1.372(4) ?
C4 H4 0.9300 ?
C5 C6 1.379(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C12 1.386(3) ?
C7 C8 1.397(3) ?
C8 C9 1.386(3) ?
C9 C10 1.382(3) ?
C9 H9 0.9300 ?
C10 C11 1.398(3) ?
C11 C12 1.371(3) ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 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
_geom_hbond_publ_flag
C2 H2 O1 2_756 0.93 2.449 3.344(5) 161.5 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
O2 S1 C1 C6 -22.3(2)
O1 S1 C1 C6 -151.29(19)
C7 S1 C1 C6 94.8(2)
O2 S1 C1 C2 157.99(19)
O1 S1 C1 C2 29.0(2)
C7 S1 C1 C2 -84.9(2)
C6 C1 C2 C3 0.2(4)
S1 C1 C2 C3 179.9(2)
C1 C2 C3 C4 -1.0(4)
C2 C3 C4 C5 1.0(5)
C3 C4 C5 C6 -0.2(5)
C4 C5 C6 C1 -0.6(4)
C2 C1 C6 C5 0.6(4)
S1 C1 C6 C5 -179.1(2)
O2 S1 C7 C12 -124.3(2)
O1 S1 C7 C12 4.3(2)
C1 S1 C7 C12 119.5(2)
O2 S1 C7 C8 51.7(2)
O1 S1 C7 C8 -179.73(19)
C1 S1 C7 C8 -64.6(2)
C13 O3 C8 C9 -4.4(4)
C13 O3 C8 C7 175.0(2)
C12 C7 C8 O3 -177.6(2)
S1 C7 C8 O3 6.5(3)
C12 C7 C8 C9 1.9(3)
S1 C7 C8 C9 -174.03(18)
O3 C8 C9 C10 179.1(2)
C7 C8 C9 C10 -0.3(4)
C14 O4 C10 C9 -10.8(4)
C14 O4 C10 C11 169.8(2)
C8 C9 C10 O4 178.7(2)
C8 C9 C10 C11 -1.9(4)
O4 C10 C11 C12 -177.9(2)
C9 C10 C11 C12 2.7(4)
O4 C10 C11 Cl1 1.7(3)
C9 C10 C11 Cl1 -177.76(19)
C10 C11 C12 C7 -1.1(4)
Cl1 C11 C12 C7 179.32(18)
C8 C7 C12 C11 -1.2(4)
S1 C7 C12 C11 174.87(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127357
