#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/54/2005419.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_2005419
loop_
_publ_author_name
'Raju, K. V. N.'
'Krishnaiah, M.'
'Chen, Y.-S.'
'Rao, S. N.'
'Holt, E. M.'
_publ_section_title
;
 (E)-6-Chloro-3-[2-(4-chlorophenylsulfonyl)ethenyl]-4-chromanone,
 (E)-6-Bromo-3-[2-(4-bromophenylsulfonyl)ethenyl]-4-chromanone
 and
 (E)-3-[2-(4-Chlorophenylsulfonyl)ethenyl]-6-methoxy-4-chromanone
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2212
_journal_page_last               2215
_journal_paper_doi               10.1107/S0108270196003563
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C18 H13 Cl1 O5 S1'
_chemical_formula_sum            'C18 H13 Cl O5 S'
_chemical_formula_weight         376.79
_chemical_melting_point          .208E-206
_chemical_name_systematic
;
(E)-3-[2-(4-chlorophenylsulfonyl) ethenyl]-6-methoxy-4H-1-benzopyran-4-
one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   39.053(13)
_cell_length_b                   6.700(2)
_cell_length_c                   13.471(5)
_cell_measurement_reflns_used    68
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.465
_cell_measurement_theta_min      6.335
_cell_volume                     3378(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_structure_refinement  SHELXS86
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Syntex P4 four-circle'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  'highly oriented graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.088
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2685
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0.0001
_diffrn_standards_interval_time  97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       cube
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.14
_refine_ls_hydrogen_treatment
;H atoms positioned by idealized geometry. Riding model with fixed
isotropic displacement parameters.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2129
_refine_ls_R_factor_obs          .0687
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0985P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         .1612
_reflns_number_observed          2129
_reflns_number_total             2166
_reflns_observed_criterion       F>2\s(F)
_cod_data_source_file            pa1224.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C18 H13 Cl1 O5 S1'
_cod_database_code               2005419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
Cl(2) 1 0.23830(7) 0.5493(4) 0.32364(14) 0.1073(10) Uani d . Cl
S(11) 1 0.15766(6) 0.0501(3) 0.57523(12) 0.0705(7) Uani d . S
O(1) 1 -0.0019(2) -0.2031(7) 0.3675(3) 0.081(2) Uani d . O
O(2) 1 0.0473(2) 0.3347(8) 0.4357(3) 0.093(2) Uani d . O
O(3) 1 0.16347(15) -0.1597(6) 0.5627(3) 0.093(2) Uani d . O
O(4) 1 0.16636(14) 0.1322(7) 0.6790(3) 0.085(2) Uani d . O
O(5) 1 -0.0844(2) 0.4738(8) 0.2929(4) 0.106(2) Uani d . O
C(2) 1 0.0336(3) -0.1901(12) 0.4054(5) 0.069(2) Uani d . C
H(2') 1 0.0471(3) -0.3119(12) 0.4177(5) 0.080 Uiso d R H
C(3) 1 0.0519(2) -0.0168(10) 0.4321(5) 0.059(2) Uani d . C
C(4) 1 0.0325(2) 0.1718(12) 0.4158(4) 0.072(2) Uani d . C
C(4') 1 -0.0058(2) 0.1553(11) 0.3721(4) 0.060(2) Uani d . C
C(5) 1 -0.0286(3) 0.3209(11) 0.3507(5) 0.083(3) Uani d . C
H(5A) 1 -0.0185(3) 0.4516(11) 0.3675(5) 0.080 Uiso d R H
C(6) 1 -0.0652(3) 0.3014(13) 0.3104(5) 0.079(3) Uani d . C
C(7) 1 -0.0800(3) 0.1100(13) 0.2891(5) 0.085(3) Uani d . C
H(7A) 1 -0.1054(3) 0.0952(13) 0.2621(5) 0.080 Uiso d R H
C(8) 1 -0.0588(3) -0.0519(13) 0.3105(5) 0.068(2) Uani d . C
H(8A) 1 -0.0687(3) -0.1833(13) 0.2960(5) 0.080 Uiso d R H
C(8') 1 -0.0225(3) -0.0319(12) 0.3508(5) 0.072(2) Uani d . C
C(9) 1 0.0902(2) -0.0319(10) 0.4751(4) 0.065(2) Uani d . C
H(9A) 1 0.0999(2) -0.1641(10) 0.4769(4) 0.080 Uiso d R H
C(10) 1 0.1143(2) 0.1071(10) 0.5150(4) 0.065(2) Uani d . C
H(10A) 1 0.1068(2) 0.2440(10) 0.5094(4) 0.080 Uiso d R H
C(12) 1 0.1819(2) 0.1868(9) 0.5061(4) 0.062(2) Uani d . C
C(13) 1 0.1888(2) 0.1053(10) 0.4194(4) 0.065(2) Uani d . C
H(13A) 1 0.1818(2) -0.0291(10) 0.3985(4) 0.080 Uiso d R H
C(14) 1 0.2065(2) 0.2173(12) 0.3639(4) 0.080(2) Uani d . C
H(14A) 1 0.2117(2) 0.1622(12) 0.3039(4) 0.080 Uiso d R H
C(15) 1 0.2169(2) 0.4099(11) 0.3941(5) 0.071(2) Uani d . C
C(16) 1 0.2097(2) 0.4904(10) 0.4793(5) 0.073(2) Uani d . C
H(16A) 1 0.2172(2) 0.6242(10) 0.5002(5) 0.080 Uiso d R H
C(17) 1 0.1917(2) 0.3814(9) 0.5348(4) 0.071(2) Uani d . C
H(17A) 1 0.1861(2) 0.4406(9) 0.5931(4) 0.080 Uiso d R H
C(18) 1 -0.1222(3) 0.4625(12) 0.2469(6) 0.110(3) Uani d . C
H(18C) 1 -0.1325(3) 0.5938(12) 0.2386(6) 0.080 Uiso d R H
H(18B) 1 -0.1275(3) 0.3979(12) 0.1807(6) 0.080 Uiso d R H
H(18A) 1 -0.1321(3) 0.3859(12) 0.2924(6) 0.080 Uiso d R H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O(3) S(11) O(4) 118.8(3) no
O(3) S(11) C(10) 109.4(3) no
O(4) S(11) C(10) 107.6(3) no
O(3) S(11) C(12) 108.6(3) no
O(4) S(11) C(12) 107.4(3) no
C(10) S(11) C(12) 104.1(3) no
C(2) O(1) C(8') 120.0(6) no
C(6) O(5) C(18) 118.6(6) no
O(2) C(4) C(4') 121.5(8) no
O(2) C(4) C(3) 123.2(8) no
C(4') C(4) C(3) 115.3(7) no
C(2) C(3) C(9) 117.0(7) no
C(2) C(3) C(4) 119.3(8) no
C(9) C(3) C(4) 123.7(7) no
O(1) C(2) C(3) 124.6(8) no
C(8) C(8') O(1) 118.1(8) no
C(8) C(8') C(4') 122.4(8) no
O(1) C(8') C(4') 119.4(9) no
C(7) C(8) C(8') 120.6(8) no
C(8) C(7) C(6) 120.1(9) no
O(5) C(6) C(5) 116.3(7) no
O(5) C(6) C(7) 124.6(9) no
C(5) C(6) C(7) 119.0(9) no
C(6) C(5) C(4') 122.1(8) no
C(5) C(4') C(8') 115.7(8) no
C(5) C(4') C(4) 123.1(8) no
C(8') C(4') C(4) 121.2(8) no
C(10) C(9) C(3) 130.4(7) no
C(9) C(10) S(11) 122.1(6) no
C(17) C(12) C(13) 120.1(7) no
C(17) C(12) S(11) 119.4(5) no
C(13) C(12) S(11) 120.3(5) no
C(16) C(17) C(12) 119.6(6) no
C(15) C(16) C(17) 120.4(6) no
C(16) C(15) C(14) 120.2(7) no
C(16) C(15) Cl(2) 120.0(6) no
C(14) C(15) Cl2 119.7(6) no
C(13) C(14) C(15) 120.0(7) no
C(14) C(13) C(12) 119.6(6) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(2) C(15) 1.711(8) yes
S(11) O(3) 1.442(5) yes
S(11) O(4) 1.450(4) yes
S(11) C(10) 1.698(8) yes
S(11) C(12) 1.763(7) yes
O(2) C(4) 1.228(7) yes
O(1) C(2) 1.336(9) yes
O(1) C(8') 1.382(9) yes
O(5) C(6) 1.360(9) yes
O(5) C(18) 1.431(11) yes
C(4) C(4') 1.446(10) yes
C(4) C(3) 1.457(10) yes
C(3) C(2) 1.357(9) yes
C(3) C(9) 1.446(10) yes
C(8') C(8) 1.369(10) yes
C(8') C(4') 1.406(10) yes
C(8) C(7) 1.345(10) yes
C(7) C(6) 1.401(10) yes
C(6) C(5) 1.384(11) yes
C(5) C(4') 1.401(10) yes
C(9) C(10) 1.324(9) yes
C(12) C(17) 1.383(8) yes
C(12) C(13) 1.385(8) yes
C(17) C(16) 1.372(9) yes
C(16) C(15) 1.368(9) yes
C(15) C(14) 1.379(9) yes
C(14) C(13) 1.376(9) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21186745
