#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/27/2232743.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_2232743
loop_
_publ_author_name
'Sinha, Suman'
'Osman, Hasnah'
'Wahab, Habibah A.'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 4-Methyl-2-oxo-2H-chromen-7-yl 4-methoxybenzenesulfonate
;
_journal_coeditor_code           HB6524
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3457
_journal_paper_doi               10.1107/S1600536811049476
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H14 O6 S'
_chemical_formula_moiety         'C17 H14 O6 S'
_chemical_formula_sum            'C17 H14 O6 S'
_chemical_formula_weight         346.34
_chemical_name_systematic
;
4-Methyl-2-oxo-2H-chromen-7-yl 4-methoxybenzenesulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.0490(10)
_cell_angle_beta                 90.2880(10)
_cell_angle_gamma                93.9450(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9801(3)
_cell_length_b                   9.2234(4)
_cell_length_c                   10.9682(5)
_cell_measurement_reflns_used    7512
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.82
_cell_measurement_theta_min      2.56
_cell_volume                     795.26(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21468
_diffrn_reflns_theta_full        33.06
_diffrn_reflns_theta_max         33.06
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.9134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                4468
_reflns_number_total             5907
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6524.cif
_cod_data_source_block           I
_cod_database_code               2232743
_cod_database_fobs_code          2232743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_symmetry_multiplicity
S S1 0.33642(4) 0.69504(3) 0.53507(3) 0.04487(10) Uani d . 1 1
O O1 0.44708(11) 0.69936(10) 0.65864(8) 0.04511(19) Uani d . 1 1
O O2 0.33520(13) 0.28756(9) 0.86131(8) 0.0501(2) Uani d . 1 1
O O3 0.45083(14) 0.76349(12) 0.45924(10) 0.0622(3) Uani d . 1 1
O O4 0.26867(14) 0.54843(11) 0.49601(9) 0.0583(3) Uani d . 1 1
O O5 0.2954(2) 0.08977(12) 0.94880(12) 0.0839(4) Uani d . 1 1
O O6 -0.18253(12) 1.08511(11) 0.72509(10) 0.0568(2) Uani d . 1 1
C C1 0.01468(16) 0.74728(13) 0.59708(11) 0.0438(2) Uani d . 1 1
H H1A -0.0095 0.6464 0.5755 0.053 Uiso calc R 1 1
C C2 -0.11060(16) 0.83699(14) 0.64295(12) 0.0449(2) Uani d . 1 1
H H2A -0.2193 0.7970 0.6513 0.054 Uiso calc R 1 1
C C3 -0.07179(15) 0.98751(13) 0.67639(11) 0.0419(2) Uani d . 1 1
C C4 0.08909(16) 1.04825(13) 0.65845(13) 0.0469(3) Uani d . 1 1
H H4A 0.1127 1.1494 0.6781 0.056 Uiso calc R 1 1
C C5 0.21342(16) 0.96007(14) 0.61205(12) 0.0453(3) Uani d . 1 1
H H5A 0.3207 1.0008 0.5999 0.054 Uiso calc R 1 1
C C6 0.17587(15) 0.80817(13) 0.58340(10) 0.0405(2) Uani d . 1 1
C C7 0.37903(14) 0.63892(12) 0.75909(10) 0.0386(2) Uani d . 1 1
C C8 0.38320(15) 0.49001(12) 0.75940(10) 0.0396(2) Uani d . 1 1
H H8A 0.4218 0.4280 0.6918 0.048 Uiso calc R 1 1
C C9 0.32790(14) 0.43633(12) 0.86381(10) 0.0382(2) Uani d . 1 1
C C10 0.2809(2) 0.21991(15) 0.95863(13) 0.0563(3) Uani d . 1 1
C C11 0.2140(2) 0.31206(16) 1.06288(13) 0.0568(3) Uani d . 1 1
H H11A 0.1724 0.2679 1.1282 0.068 Uiso calc R 1 1
C C12 0.20871(17) 0.45853(14) 1.07064(11) 0.0458(3) Uani d . 1 1
C C13 0.26811(14) 0.52666(12) 0.96685(10) 0.0383(2) Uani d . 1 1
C C14 0.26642(17) 0.67727(13) 0.96096(11) 0.0452(3) Uani d . 1 1
H H14A 0.2273 0.7400 1.0279 0.054 Uiso calc R 1 1
C C15 0.32143(17) 0.73451(13) 0.85815(12) 0.0456(3) Uani d . 1 1
H H15A 0.3200 0.8346 0.8552 0.055 Uiso calc R 1 1
C C16 0.1440(2) 0.55079(18) 1.18327(12) 0.0630(4) Uani d . 1 1
H H16A 0.1057 0.4884 1.2412 0.095 Uiso calc R 1 1
H H16B 0.0523 0.6035 1.1600 0.095 Uiso calc R 1 1
H H16C 0.2324 0.6196 1.2206 0.095 Uiso calc R 1 1
C C17 -0.34930(19) 1.03035(18) 0.74647(17) 0.0627(4) Uani d . 1 1
H H17A -0.4167 1.1113 0.7733 0.094 Uiso calc R 1 1
H H17B -0.3472 0.9685 0.8091 0.094 Uiso calc R 1 1
H H17C -0.3963 0.9743 0.6714 0.094 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O4 120.27(7)
O3 S1 O1 101.84(6)
O4 S1 O1 108.68(6)
O3 S1 C6 111.00(6)
O4 S1 C6 109.96(6)
O1 S1 C6 103.45(5)
C7 O1 S1 120.22(7)
C9 O2 C10 121.61(10)
C3 O6 C17 118.18(11)
C6 C1 C2 119.95(11)
C6 C1 H1A 120.0
C2 C1 H1A 120.0
C1 C2 C3 119.29(11)
C1 C2 H2A 120.4
C3 C2 H2A 120.4
O6 C3 C2 124.50(11)
O6 C3 C4 115.21(11)
C2 C3 C4 120.28(11)
C5 C4 C3 120.64(11)
C5 C4 H4A 119.7
C3 C4 H4A 119.7
C4 C5 C6 118.91(11)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C1 C6 C5 120.83(11)
C1 C6 S1 120.13(9)
C5 C6 S1 119.00(9)
C8 C7 C15 122.74(11)
C8 C7 O1 119.03(10)
C15 C7 O1 118.06(10)
C7 C8 C9 117.46(10)
C7 C8 H8A 121.3
C9 C8 H8A 121.3
O2 C9 C8 115.88(9)
O2 C9 C13 121.43(10)
C8 C9 C13 122.69(10)
O5 C10 O2 116.70(13)
O5 C10 C11 126.35(14)
O2 C10 C11 116.95(11)
C12 C11 C10 123.40(13)
C12 C11 H11A 118.3
C10 C11 H11A 118.3
C11 C12 C13 118.25(11)
C11 C12 C16 121.49(12)
C13 C12 C16 120.26(12)
C9 C13 C14 117.23(10)
C9 C13 C12 118.30(10)
C14 C13 C12 124.45(10)
C15 C14 C13 121.51(10)
C15 C14 H14A 119.2
C13 C14 H14A 119.2
C14 C15 C7 118.37(11)
C14 C15 H15A 120.8
C7 C15 H15A 120.8
C12 C16 H16A 109.5
C12 C16 H16B 109.5
H16A C16 H16B 109.5
C12 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O6 C17 H17A 109.5
O6 C17 H17B 109.5
H17A C17 H17B 109.5
O6 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4203(10)
S1 O4 1.4210(10)
S1 O1 1.6076(10)
S1 C6 1.7401(12)
O1 C7 1.4061(14)
O2 C9 1.3734(13)
O2 C10 1.3760(17)
O5 C10 1.2018(16)
O6 C3 1.3563(15)
O6 C17 1.4244(18)
C1 C6 1.3862(17)
C1 C2 1.3875(18)
C1 H1A 0.9300
C2 C3 1.3919(17)
C2 H2A 0.9300
C3 C4 1.3924(18)
C4 C5 1.3751(18)
C4 H4A 0.9300
C5 C6 1.3979(16)
C5 H5A 0.9300
C7 C8 1.3766(15)
C7 C15 1.3887(16)
C8 C9 1.3801(16)
C8 H8A 0.9300
C9 C13 1.4011(14)
C10 C11 1.441(2)
C11 C12 1.3439(19)
C11 H11A 0.9300
C12 C13 1.4509(17)
C12 C16 1.5011(18)
C13 C14 1.4017(16)
C14 C15 1.3796(18)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 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
C8 H8A O3 2_666 0.93 2.50 3.4156(16) 169 yes
C15 H15A O5 1_565 0.93 2.44 3.2923(17) 153 yes
C16 H16B Cg1 2_567 0.96 2.96 3.8423(17) 154 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
O3 S1 O1 C7 -179.12(8)
O4 S1 O1 C7 -51.20(10)
C6 S1 O1 C7 65.63(9)
C6 C1 C2 C3 -0.89(19)
C17 O6 C3 C2 1.5(2)
C17 O6 C3 C4 -179.69(13)
C1 C2 C3 O6 -178.23(12)
C1 C2 C3 C4 3.04(19)
O6 C3 C4 C5 178.64(12)
C2 C3 C4 C5 -2.5(2)
C3 C4 C5 C6 -0.2(2)
C2 C1 C6 C5 -1.80(19)
C2 C1 C6 S1 175.99(9)
C4 C5 C6 C1 2.33(19)
C4 C5 C6 S1 -175.49(10)
O3 S1 C6 C1 145.04(11)
O4 S1 C6 C1 9.50(12)
O1 S1 C6 C1 -106.43(10)
O3 S1 C6 C5 -37.13(12)
O4 S1 C6 C5 -172.67(10)
O1 S1 C6 C5 71.40(10)
S1 O1 C7 C8 83.63(12)
S1 O1 C7 C15 -100.99(12)
C15 C7 C8 C9 -0.32(18)
O1 C7 C8 C9 174.84(10)
C10 O2 C9 C8 -178.76(12)
C10 O2 C9 C13 1.40(19)
C7 C8 C9 O2 -179.45(10)
C7 C8 C9 C13 0.38(18)
C9 O2 C10 O5 -178.61(15)
C9 O2 C10 C11 0.7(2)
O5 C10 C11 C12 176.67(18)
O2 C10 C11 C12 -2.6(2)
C10 C11 C12 C13 2.2(2)
C10 C11 C12 C16 -177.60(15)
O2 C9 C13 C14 179.63(11)
C8 C9 C13 C14 -0.20(18)
O2 C9 C13 C12 -1.81(17)
C8 C9 C13 C12 178.37(11)
C11 C12 C13 C9 0.03(19)
C16 C12 C13 C9 179.81(12)
C11 C12 C13 C14 178.48(13)
C16 C12 C13 C14 -1.7(2)
C9 C13 C14 C15 -0.06(18)
C12 C13 C14 C15 -178.53(12)
C13 C14 C15 C7 0.1(2)
C8 C7 C15 C14 0.1(2)
O1 C7 C15 C14 -175.12(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1373256
