#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006262.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_2006262
loop_
_publ_author_name
'Sriram, D.'
'Srinivasan, S.'
'Santhosh, K. C.'
_publ_section_title
;
 3-Phenylsulfonyl-3-(2-propenyl)chroman-4-one
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              793
_journal_page_last               794
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C18 H16 O4 S'
_chemical_formula_weight         328.37
_chemical_melting_point          114
_chemical_name_systematic
;
3-phenylsulfonyl-3(2-propenyl)chroman-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.04(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.890(3)
_cell_length_b                   14.122(3)
_cell_length_c                   11.856(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      8
_cell_volume                     1639.6(7)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w-2\q
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2765
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       cylindrical
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .22
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.088
_refine_ls_goodness_of_fit_obs   1.120
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_restrained_S_obs      1.120
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_obs          0.0502
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0642P)^2^+1.1547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1337
_refine_ls_wR_factor_obs         0.1274
_reflns_number_observed          2267
_reflns_number_total             2606
_reflns_observed_criterion       >3sigma(I)
_[local]_cod_data_source_file    vj1050.cif
_[local]_cod_data_source_block   chromanone4
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        1639.5(7)
_cod_database_code               2006262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y-1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0313(3) 0.0488(4) 0.0521(4) -0.0029(3) 0.0116(3) -0.0067(3)
O1 0.0484(11) 0.0585(13) 0.0588(12) 0.0047(9) 0.0010(10) 0.0064(10)
O2 0.087(2) 0.093(2) 0.068(2) -0.0018(15) -0.0027(13) 0.0305(14)
O3 0.0640(13) 0.0654(14) 0.0690(14) -0.0149(11) 0.0348(11) -0.0075(11)
O4 0.0325(10) 0.0741(15) 0.0715(14) 0.0059(9) -0.0045(10) -0.0139(11)
C2 0.0360(13) 0.0407(14) 0.0436(14) 0.0017(11) 0.0058(11) -0.0037(11)
C1 0.050(2) 0.059(2) 0.052(2) -0.0008(14) 0.0070(14) -0.0036(15)
C9 0.0356(14) 0.052(2) 0.061(2) -0.0073(12) 0.0099(13) -0.0119(14)
C7 0.043(2) 0.079(3) 0.103(3) 0.002(2) 0.003(2) -0.005(2)
C6 0.042(2) 0.099(3) 0.162(5) -0.005(2) 0.040(3) -0.026(3)
C5 0.084(3) 0.123(4) 0.118(4) -0.032(3) 0.068(3) -0.027(3)
C4 0.081(3) 0.091(3) 0.074(3) -0.027(2) 0.026(2) 0.005(2)
C8 0.0412(15) 0.052(2) 0.065(2) -0.0108(13) 0.0118(14) -0.0020(15)
C3 0.057(2) 0.051(2) 0.047(2) -0.0122(14) -0.0006(13) 0.0055(14)
C10 0.0348(13) 0.0405(14) 0.0470(15) -0.0050(11) 0.0068(11) -0.0058(12)
C11 0.070(2) 0.049(2) 0.050(2) 0.002(2) 0.005(2) 0.0003(15)
C12 0.088(3) 0.055(2) 0.078(3) 0.027(2) -0.009(2) -0.007(2)
C13 0.073(2) 0.070(2) 0.083(3) 0.026(2) 0.007(2) -0.023(2)
C14 0.070(2) 0.073(2) 0.059(2) 0.006(2) 0.018(2) -0.019(2)
C15 0.047(2) 0.054(2) 0.049(2) 0.0034(14) 0.0057(13) -0.0019(14)
C16 0.055(2) 0.061(2) 0.085(3) 0.010(2) 0.010(2) -0.020(2)
C17 0.082(3) 0.053(2) 0.093(3) 0.015(2) 0.005(2) -0.008(2)
C18 0.126(4) 0.068(3) 0.095(3) 0.018(3) -0.010(3) -0.025(3)
loop_
_atom_site_label
_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_occupancy
_atom_site_type_symbol
S 0.01049(6) 0.47267(5) 0.75713(6) 0.0435(2) Uani d 1 S
O1 0.3147(2) 0.49786(15) 0.8962(2) 0.0558(5) Uani d 1 O
O2 0.1375(3) 0.6564(2) 0.6276(2) 0.0840(8) Uani d 1 O
O3 -0.0337(2) 0.4356(2) 0.8586(2) 0.0637(6) Uani d 1 O
O4 -0.0903(2) 0.5005(2) 0.6638(2) 0.0605(6) Uani d 1 O
C2 0.1111(2) 0.5792(2) 0.8012(2) 0.0401(6) Uani d 1 C
C1 0.2088(3) 0.5617(3) 0.9099(3) 0.0537(8) Uani d 1 C
C9 0.3843(3) 0.5193(2) 0.8063(3) 0.0490(7) Uani d 1 C
C7 0.5137(4) 0.4798(3) 0.8129(4) 0.0758(11) Uani d 1 C
C6 0.5900(4) 0.4980(4) 0.7282(6) 0.098(2) Uani d 1 C
C5 0.5408(5) 0.5527(4) 0.6372(6) 0.103(2) Uani d 1 C
C4 0.4121(4) 0.5911(3) 0.6297(4) 0.0804(12) Uani d 1 C
C8 0.3318(3) 0.5735(2) 0.7144(3) 0.0522(7) Uani d 1 C
C3 0.1885(3) 0.6095(2) 0.7053(3) 0.0524(7) Uani d 1 C
C10 0.1179(2) 0.3881(2) 0.7055(2) 0.0407(6) Uani d 1 C
C11 0.1818(3) 0.3208(2) 0.7782(3) 0.0567(8) Uani d 1 C
C12 0.2628(4) 0.2538(3) 0.7360(4) 0.0757(11) Uani d 1 C
C13 0.2789(4) 0.2546(3) 0.6236(4) 0.0758(11) Uani d 1 C
C14 0.2142(4) 0.3211(3) 0.5516(3) 0.0667(9) Uani d 1 C
C15 0.1321(3) 0.3887(2) 0.5916(3) 0.0502(7) Uani d 1 C
C16 0.0022(4) 0.6538(3) 0.8240(4) 0.0669(10) Uani d 1 C
C17 0.0634(4) 0.7470(3) 0.8628(4) 0.0768(11) Uani d 1 C
C18 0.0586(6) 0.7845(4) 0.9606(5) 0.099(2) Uani d 1 C
H1 0.251(3) 0.625(2) 0.937(2) 0.056(8) Uiso d 1 H
H1' 0.171(4) 0.530(3) 0.971(4) 0.101(14) Uiso d 1 H
H7 0.540(4) 0.442(3) 0.876(4) 0.090(14) Uiso d 1 H
H6 0.670(6) 0.474(4) 0.725(4) 0.134(19) Uiso d 1 H
H5 0.588(5) 0.559(4) 0.578(4) 0.125(17) Uiso d 1 H
H4 0.374(4) 0.629(3) 0.568(3) 0.077(12) Uiso d 1 H
H11 0.171(3) 0.318(2) 0.852(3) 0.051(8) Uiso d 1 H
H12 0.302(4) 0.211(3) 0.785(3) 0.084(12) Uiso d 1 H
H13 0.335(4) 0.206(3) 0.598(3) 0.091(12) Uiso d 1 H
H14 0.227(4) 0.321(3) 0.473(3) 0.073(10) Uiso d 1 H
H15 0.093(3) 0.435(2) 0.546(3) 0.049(8) Uiso d 1 H
H16 -0.064(5) 0.657(4) 0.745(4) 0.130(17) Uiso d 1 H
H16' -0.036(4) 0.629(3) 0.888(4) 0.084(12) Uiso d 1 H
H17 0.109(5) 0.781(3) 0.796(4) 0.112(15) Uiso d 1 H
H18 0.101(5) 0.847(4) 0.974(4) 0.131(18) Uiso d 1 H
H18' 0.016(8) 0.738(6) 1.003(6) 0.19(3) Uiso d 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'
S S 0.1246 0.1234 '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'
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
O3 S O4 119.05(14) ?
O3 S C10 108.21(14) ?
O4 S C10 107.74(13) ?
O3 S C2 106.07(13) ?
O4 S C2 106.52(13) ?
C10 S C2 108.93(12) y
C9 O1 C1 114.0(2) y
C1 C2 C3 110.7(2) y
C1 C2 C16 109.7(3) ?
C3 C2 C16 111.9(3) ?
C1 C2 S 111.3(2) ?
C3 C2 S 109.1(2) ?
C16 C2 S 104.1(2) ?
O1 C1 C2 113.7(2) y
C8 C9 O1 124.1(3) y
C8 C9 C7 120.8(3) ?
O1 C9 C7 115.1(3) y
C6 C7 C9 118.9(5) ?
C5 C6 C7 121.2(4) ?
C6 C5 C4 120.1(4) ?
C5 C4 C8 120.0(5) ?
C9 C8 C4 118.9(3) ?
C9 C8 C3 119.8(3) ?
C4 C8 C3 121.3(3) ?
O2 C3 C8 122.7(3) y
O2 C3 C2 122.3(3) y
C8 C3 C2 115.0(2) y
C11 C10 C15 121.2(3) ?
C11 C10 S 119.8(2) ?
C15 C10 S 119.0(2) ?
C10 C11 C12 119.1(3) ?
C13 C12 C11 120.1(4) ?
C12 C13 C14 120.5(3) ?
C13 C14 C15 120.5(3) ?
C10 C15 C14 118.6(3) ?
C17 C16 C2 112.9(3) ?
C18 C17 C16 125.3(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O3 1.435(2) ?
S O4 1.436(2) ?
S C10 1.763(3) y
S C2 1.839(3) y
O1 C9 1.381(3) y
O1 C1 1.408(4) y
O2 C3 1.189(4) y
C2 C1 1.519(4) y
C2 C3 1.518(4) y
C2 C16 1.557(4) ?
C9 C8 1.373(4) y
C9 C7 1.388(5) ?
C7 C6 1.362(7) ?
C6 C5 1.360(8) ?
C5 C4 1.376(7) ?
C4 C8 1.388(5) ?
C8 C3 1.495(4) y
C10 C11 1.377(4) ?
C10 C15 1.377(4) ?
C11 C12 1.379(5) ?
C12 C13 1.364(6) ?
C13 C14 1.366(5) ?
C14 C15 1.380(4) ?
C16 C17 1.493(5) ?
C17 C18 1.282(6) y
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
_geom_torsion_publ_flag
O3 S C2 C1 44.5(2) ?
O4 S C2 C1 172.3(2) ?
C10 S C2 C1 -71.7(2) ?
O3 S C2 C3 166.9(2) ?
O4 S C2 C3 -65.3(2) ?
C10 S C2 C3 50.7(2) ?
O3 S C2 C16 -73.5(2) ?
O4 S C2 C16 54.3(2) ?
C10 S C2 C16 170.2(2) y
C9 O1 C1 C2 50.9(3) y
C3 C2 C1 O1 -53.5(4) y
C16 C2 C1 O1 -177.5(3) y
S C2 C1 O1 67.9(3) ?
C1 O1 C9 C8 -22.3(4) y
C1 O1 C9 C7 159.1(3) ?
C8 C9 C7 C6 2.0(6) ?
O1 C9 C7 C6 -179.4(3) ?
C9 C7 C6 C5 -1.0(7) ?
C7 C6 C5 C4 0.3(8) ?
C6 C5 C4 C8 -0.5(7) ?
O1 C9 C8 C4 179.3(3) ?
C7 C9 C8 C4 -2.2(5) ?
O1 C9 C8 C3 -2.9(4) y
C7 C9 C8 C3 175.6(3) ?
C5 C4 C8 C9 1.5(6) ?
C5 C4 C8 C3 -176.3(4) ?
C9 C8 C3 O2 -179.8(3) ?
C4 C8 C3 O2 -2.0(5) ?
C9 C8 C3 C2 -1.4(4) y
C4 C8 C3 C2 176.4(3) ?
C1 C2 C3 O2 -153.9(3) ?
C16 C2 C3 O2 -31.2(4) ?
S C2 C3 O2 83.4(3) y
C1 C2 C3 C8 27.7(3) y
C16 C2 C3 C8 150.4(3) ?
S C2 C3 C8 -95.0(2) ?
O3 S C10 C11 -21.9(3) ?
O4 S C10 C11 -151.8(2) ?
C2 S C10 C11 93.0(2) ?
O3 S C10 C15 155.7(2) ?
O4 S C10 C15 25.8(3) ?
C2 S C10 C15 -89.4(2) ?
C15 C10 C11 C12 0.9(5) ?
S C10 C11 C12 178.5(3) ?
C10 C11 C12 C13 -0.1(6) ?
C11 C12 C13 C14 -0.6(6) ?
C12 C13 C14 C15 0.3(6) ?
C11 C10 C15 C14 -1.2(4) ?
S C10 C15 C14 -178.7(2) ?
C13 C14 C15 C10 0.5(5) ?
C1 C2 C16 C17 60.2(4) ?
C3 C2 C16 C17 -63.0(4) y
S C2 C16 C17 179.4(3) ?
C2 C16 C17 C18 -115.7(5) ?