#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/20/2232017.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_2232017
loop_
_publ_author_name
'Abdel-Aziz, Hatem A.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-(1-Benzofuran-2-yl)-2-(phenylsulfonyl)ethanone
;
_journal_coeditor_code           PK2346
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2675
_journal_paper_doi               10.1107/S1600536811037366
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 O4 S'
_chemical_formula_moiety         'C16 H12 O4 S'
_chemical_formula_sum            'C16 H12 O4 S'
_chemical_formula_weight         300.32
_chemical_name_systematic
;
1-(1-Benzofuran-2-yl)-2-(phenylsulfonyl)ethanone
;
_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                 91.024(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7560(2)
_cell_length_b                   4.78550(10)
_cell_length_c                   26.1838(5)
_cell_measurement_reflns_used    3182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9788
_cell_measurement_theta_min      3.3736
_cell_volume                     1347.54(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4617
_diffrn_reflns_theta_full        74.15
_diffrn_reflns_theta_max         74.15
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.471
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.6486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2495
_reflns_number_total             2650
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2346.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2232017
_cod_database_fobs_code          2232017
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_symmetry_multiplicity
S S1 0.53618(3) 0.14747(7) 0.735119(11) 0.01251(11) Uani d . 1 1
O O1 0.63911(9) -0.0313(2) 0.74882(4) 0.0174(2) Uani d . 1 1
O O2 0.42375(9) 0.0193(2) 0.71500(4) 0.0178(2) Uani d . 1 1
O O3 0.64086(10) 0.0614(2) 0.62454(4) 0.0228(2) Uani d . 1 1
O O4 0.46617(9) 0.2296(2) 0.55532(4) 0.0173(2) Uani d . 1 1
C C1 0.49885(13) 0.3575(3) 0.78787(5) 0.0137(3) Uani d . 1 1
C C2 0.59334(13) 0.4305(3) 0.82217(5) 0.0163(3) Uani d . 1 1
H H2 0.6754 0.3613 0.8182 0.020 Uiso calc R 1 1
C C3 0.56524(14) 0.6072(3) 0.86253(6) 0.0201(3) Uani d . 1 1
H H3 0.6284 0.6594 0.8865 0.024 Uiso calc R 1 1
C C4 0.44511(14) 0.7074(3) 0.86776(5) 0.0218(3) Uani d . 1 1
H H4 0.4266 0.8293 0.8952 0.026 Uiso calc R 1 1
C C5 0.35163(14) 0.6309(3) 0.83320(6) 0.0225(3) Uani d . 1 1
H H5 0.2696 0.7000 0.8373 0.027 Uiso calc R 1 1
C C6 0.37766(13) 0.4545(3) 0.79284(5) 0.0183(3) Uani d . 1 1
H H6 0.3142 0.4008 0.7691 0.022 Uiso calc R 1 1
C C7 0.58626(13) 0.3948(3) 0.68830(5) 0.0156(3) Uani d . 1 1
H H7A 0.5339 0.5648 0.6894 0.019 Uiso calc R 1 1
H H7B 0.6737 0.4494 0.6953 0.019 Uiso calc R 1 1
C C8 0.57443(13) 0.2571(3) 0.63613(5) 0.0159(3) Uani d . 1 1
C C9 0.47739(13) 0.3641(3) 0.60172(5) 0.0152(3) Uani d . 1 1
C C10 0.39035(13) 0.5678(3) 0.60687(5) 0.0166(3) Uani d . 1 1
H H10 0.3806 0.6887 0.6353 0.020 Uiso calc R 1 1
C C11 0.31615(13) 0.5640(3) 0.56082(5) 0.0166(3) Uani d . 1 1
C C12 0.21147(14) 0.7095(3) 0.54235(6) 0.0218(3) Uani d . 1 1
H H12 0.1746 0.8536 0.5619 0.026 Uiso calc R 1 1
C C13 0.16361(15) 0.6368(3) 0.49482(6) 0.0242(3) Uani d . 1 1
H H13 0.0919 0.7305 0.4818 0.029 Uiso calc R 1 1
C C14 0.21907(15) 0.4270(3) 0.46533(6) 0.0231(3) Uani d . 1 1
H H14 0.1843 0.3841 0.4327 0.028 Uiso calc R 1 1
C C15 0.32250(15) 0.2813(3) 0.48237(5) 0.0205(3) Uani d . 1 1
H H15 0.3604 0.1402 0.4624 0.025 Uiso calc R 1 1
C C16 0.36750(13) 0.3544(3) 0.53055(5) 0.0163(3) Uani d . 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 118.23(6)
O1 S1 C1 109.21(6)
O2 S1 C1 109.08(6)
O1 S1 C7 108.87(6)
O2 S1 C7 106.87(6)
C1 S1 C7 103.59(7)
C16 O4 C9 105.58(11)
C2 C1 C6 122.09(13)
C2 C1 S1 118.46(11)
C6 C1 S1 119.40(11)
C1 C2 C3 118.55(13)
C1 C2 H2 120.7
C3 C2 H2 120.7
C4 C3 C2 120.04(14)
C4 C3 H3 120.0
C2 C3 H3 120.0
C5 C4 C3 120.60(14)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.23(14)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 118.49(13)
C5 C6 H6 120.8
C1 C6 H6 120.8
C8 C7 S1 107.86(10)
C8 C7 H7A 110.1
S1 C7 H7A 110.1
C8 C7 H7B 110.1
S1 C7 H7B 110.1
H7A C7 H7B 108.4
O3 C8 C9 122.11(13)
O3 C8 C7 121.11(13)
C9 C8 C7 116.75(12)
C10 C9 O4 111.88(12)
C10 C9 C8 132.54(13)
O4 C9 C8 115.52(12)
C9 C10 C11 106.31(13)
C9 C10 H10 126.8
C11 C10 H10 126.8
C16 C11 C12 118.92(13)
C16 C11 C10 105.45(13)
C12 C11 C10 135.62(14)
C13 C12 C11 117.97(15)
C13 C12 H12 121.0
C11 C12 H12 121.0
C12 C13 C14 121.27(15)
C12 C13 H13 119.4
C14 C13 H13 119.4
C15 C14 C13 122.05(14)
C15 C14 H14 119.0
C13 C14 H14 119.0
C14 C15 C16 115.62(14)
C14 C15 H15 122.2
C16 C15 H15 122.2
O4 C16 C15 125.07(13)
O4 C16 C11 110.78(12)
C15 C16 C11 124.14(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4394(10)
S1 O2 1.4468(10)
S1 C1 1.7603(14)
S1 C7 1.7936(15)
O3 C8 1.2193(18)
O4 C16 1.3708(17)
O4 C9 1.3781(16)
C1 C2 1.3891(19)
C1 C6 1.3919(19)
C2 C3 1.391(2)
C2 H2 0.9500
C3 C4 1.387(2)
C3 H3 0.9500
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.385(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5201(18)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.460(2)
C9 C10 1.360(2)
C10 C11 1.4343(19)
C10 H10 0.9500
C11 C16 1.398(2)
C11 C12 1.403(2)
C12 C13 1.383(2)
C12 H12 0.9500
C13 C14 1.406(2)
C13 H13 0.9500
C14 C15 1.380(2)
C14 H14 0.9500
C15 C16 1.388(2)
C15 H15 0.9500
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
C3 H3 O3 2_656 0.95 2.55 3.1808(19) 124
C7 H7a O2 1_565 0.99 2.57 3.5383(17) 165
C7 H7b O1 2_656 0.99 2.47 3.3746(17) 152
C15 H15 O3 3_656 0.95 2.47 3.2742(17) 142
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
O1 S1 C1 C2 29.99(13)
O2 S1 C1 C2 160.57(11)
C7 S1 C1 C2 -85.89(12)
O1 S1 C1 C6 -152.63(12)
O2 S1 C1 C6 -22.06(14)
C7 S1 C1 C6 91.48(13)
C6 C1 C2 C3 -0.3(2)
S1 C1 C2 C3 177.00(11)
C1 C2 C3 C4 -0.2(2)
C2 C3 C4 C5 0.5(2)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C1 -0.2(2)
C2 C1 C6 C5 0.5(2)
S1 C1 C6 C5 -176.78(12)
O1 S1 C7 C8 84.82(11)
O2 S1 C7 C8 -43.93(11)
C1 S1 C7 C8 -159.05(10)
S1 C7 C8 O3 -67.61(16)
S1 C7 C8 C9 110.33(12)
C16 O4 C9 C10 -0.23(15)
C16 O4 C9 C8 177.42(12)
O3 C8 C9 C10 176.92(15)
C7 C8 C9 C10 -1.0(2)
O3 C8 C9 O4 -0.1(2)
C7 C8 C9 O4 -178.03(11)
O4 C9 C10 C11 0.70(16)
C8 C9 C10 C11 -176.42(15)
C9 C10 C11 C16 -0.87(16)
C9 C10 C11 C12 177.66(16)
C16 C11 C12 C13 0.3(2)
C10 C11 C12 C13 -178.10(16)
C11 C12 C13 C14 -1.1(2)
C12 C13 C14 C15 0.8(2)
C13 C14 C15 C16 0.4(2)
C9 O4 C16 C15 -179.32(14)
C9 O4 C16 C11 -0.36(15)
C14 C15 C16 O4 177.59(13)
C14 C15 C16 C11 -1.2(2)
C12 C11 C16 O4 -178.05(13)
C10 C11 C16 O4 0.77(16)
C12 C11 C16 C15 0.9(2)
C10 C11 C16 C15 179.74(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13077903
