#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229679.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_2229679
loop_
_publ_author_name
'Nasir, Waqar'
'Munawar, Munawar Ali'
'Nadeem, Sohail'
'Amjad, Rana'
'Adnan, Ahmad'
_publ_section_title
;
 4-[2-(Benzylsulfanyl)acetyl]-3,4-dihydroquinoxalin-2(1H)-one
;
_journal_coeditor_code           HG2799
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o848
_journal_paper_doi               10.1107/S1600536811008178
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H16 N2 O2 S'
_chemical_formula_moiety         'C17 H16 N2 O2 S'
_chemical_formula_sum            'C17 H16 N2 O2 S'
_chemical_formula_weight         312.38
_chemical_name_systematic
;
4-[2-(Benzylsulfanyl)acetyl]-3,4-dihydroquinoxalin-2(1H)-one
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9502(8)
_cell_length_b                   32.2588(17)
_cell_length_c                   6.9728(3)
_cell_measurement_reflns_used    2915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      3.18
_cell_volume                     3137.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16363
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0552
_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)+(0.1080P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1829
_reflns_number_gt                2412
_reflns_number_total             3892
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2799.cif
_cod_data_source_block           I
_cod_database_code               2229679
_cod_database_fobs_code          2229679
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -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_disorder_assembly
_atom_site_disorder_group
S S1 0.67947(5) 0.701430(18) 0.13947(11) 0.0539(3) Uani d . 1 . .
O O4 0.77529(11) 0.61610(5) 0.1173(2) 0.0439(4) Uani d . 1 . .
N N1 0.63517(13) 0.58234(5) 0.0968(3) 0.0364(4) Uani d . 1 . .
O O3 0.63199(12) 0.50899(5) 0.4824(2) 0.0530(5) Uani d . 1 . .
C C1 0.47960(15) 0.55216(6) 0.1309(3) 0.0377(5) Uani d . 1 . .
C C9 0.69061(15) 0.61743(6) 0.0743(3) 0.0331(5) Uani d . 1 . .
C C8 0.60499(16) 0.52927(7) 0.3446(3) 0.0399(5) Uani d . 1 . .
C C7 0.67595(15) 0.54813(7) 0.2064(3) 0.0400(5) Uani d . 1 . .
H H7A 0.7311 0.5581 0.2775 0.048 Uiso calc R 1 . .
H H7B 0.6980 0.5269 0.1184 0.048 Uiso calc R 1 . .
N N2 0.51165(14) 0.53532(6) 0.3046(3) 0.0442(5) Uani d . 1 . .
C C10 0.64388(16) 0.65674(7) 0.0037(3) 0.0394(5) Uani d . 1 . .
H H10A 0.5748 0.6537 0.0112 0.047 Uiso calc R 1 . .
H H10B 0.6607 0.6610 -0.1299 0.047 Uiso calc R 1 . .
C C5 0.51272(19) 0.58963(8) -0.1586(4) 0.0490(6) Uani d . 1 . .
H H5 0.5557 0.6032 -0.2391 0.059 Uiso calc R 1 . .
C C12 0.50134(19) 0.69134(8) 0.3071(4) 0.0514(6) Uani d . 1 . .
C C6 0.54236(15) 0.57563(6) 0.0199(3) 0.0364(5) Uani d . 1 . .
C C3 0.35632(19) 0.56161(9) -0.1015(4) 0.0581(7) Uani d . 1 . .
H H3 0.2931 0.5579 -0.1402 0.070 Uiso calc R 1 . .
C C2 0.38689(17) 0.54535(7) 0.0697(4) 0.0477(6) Uani d . 1 . .
H H2 0.3451 0.5297 0.1445 0.057 Uiso calc R 1 . .
C C11 0.6058(2) 0.69568(9) 0.3512(4) 0.0577(7) Uani d . 1 . .
H H11A 0.6269 0.6714 0.4217 0.069 Uiso calc R 1 . .
H H11B 0.6150 0.7197 0.4332 0.069 Uiso calc R 1 . .
C C4 0.4191(2) 0.58341(8) -0.2165(4) 0.0592(7) Uani d . 1 . .
H H4 0.3983 0.5940 -0.3334 0.071 Uiso calc R 1 . .
C C13 0.4534(3) 0.65588(11) 0.3446(5) 0.0776(9) Uani d . 1 . .
H H13 0.4853 0.6339 0.4025 0.093 Uiso calc R 1 . .
C C16 0.3583(3) 0.7183(2) 0.1691(9) 0.156(3) Uani d . 1 . .
H H16 0.3267 0.7396 0.1054 0.188 Uiso calc R 1 . .
C C14 0.3569(3) 0.65185(15) 0.2976(7) 0.1123(16) Uani d . 1 . .
H H14 0.3240 0.6275 0.3254 0.135 Uiso calc R 1 . .
C C17 0.4533(2) 0.72278(13) 0.2194(7) 0.1095(15) Uani d . 1 . .
H H17 0.4849 0.7475 0.1932 0.131 Uiso calc R 1 . .
C C15 0.3119(3) 0.6836(2) 0.2115(7) 0.133(2) Uani d . 1 . .
H H15 0.2473 0.6812 0.1811 0.160 Uiso calc R 1 . .
H H1N 0.471(2) 0.5207(9) 0.367(4) 0.060(8) Uiso d . 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 S1 C11 . . 101.02(12) ?
C9 N1 C6 . . 126.45(18) ?
C9 N1 C7 . . 117.51(17) ?
C6 N1 C7 . . 116.03(17) ?
C2 C1 C6 . . 120.3(2) ?
C2 C1 N2 . . 120.3(2) ?
C6 C1 N2 . . 119.4(2) ?
O4 C9 N1 . . 119.08(19) ?
O4 C9 C10 . . 121.91(19) ?
N1 C9 C10 . . 118.98(19) ?
O3 C8 N2 . . 122.6(2) ?
O3 C8 C7 . . 121.0(2) ?
N2 C8 C7 . . 116.3(2) ?
N1 C7 C8 . . 112.57(18) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C8 N2 C1 . . 123.0(2) ?
C8 N2 H1N . . 117.0(19) ?
C1 N2 H1N . . 116.3(19) ?
C9 C10 S1 . . 112.54(16) ?
C9 C10 H10A . . 109.1 ?
S1 C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
S1 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
C4 C5 C6 . . 119.8(2) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C13 C12 C17 . . 118.3(3) ?
C13 C12 C11 . . 121.4(3) ?
C17 C12 C11 . . 120.2(3) ?
C5 C6 C1 . . 119.2(2) ?
C5 C6 N1 . . 124.2(2) ?
C1 C6 N1 . . 116.55(19) ?
C2 C3 C4 . . 120.2(2) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C2 C1 . . 120.0(2) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C12 C11 S1 . . 113.29(19) ?
C12 C11 H11A . . 108.9 ?
S1 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
S1 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C3 C4 C5 . . 120.3(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C12 C13 C14 . . 120.8(4) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C15 C16 C17 . . 120.0(5) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C15 C14 C13 . . 119.1(4) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C12 C17 C16 . . 120.7(4) ?
C12 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C16 C15 C14 . . 121.1(4) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 . 1.795(2) ?
S1 C11 . 1.808(3) ?
O4 C9 . 1.219(3) ?
N1 C9 . 1.380(3) ?
N1 C6 . 1.418(3) ?
N1 C7 . 1.458(3) ?
O3 C8 . 1.222(3) ?
C1 C2 . 1.380(3) ?
C1 C6 . 1.393(3) ?
C1 N2 . 1.400(3) ?
C9 C10 . 1.508(3) ?
C8 N2 . 1.346(3) ?
C8 C7 . 1.509(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
N2 H1N . 0.85(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C5 C4 . 1.382(4) ?
C5 C6 . 1.387(3) ?
C5 H5 . 0.9300 ?
C12 C13 . 1.351(4) ?
C12 C17 . 1.361(4) ?
C12 C11 . 1.496(4) ?
C3 C2 . 1.372(4) ?
C3 C4 . 1.380(4) ?
C3 H3 . 0.9300 ?
C2 H2 . 0.9300 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C4 H4 . 0.9300 ?
C13 C14 . 1.392(5) ?
C13 H13 . 0.9300 ?
C16 C15 . 1.327(8) ?
C16 C17 . 1.379(6) ?
C16 H16 . 0.9300 ?
C14 C15 . 1.342(7) ?
C14 H14 . 0.9300 ?
C17 H17 . 0.9300 ?
C15 H15 . 0.9300 ?
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
C5 H5 O4 7_755 0.93 2.60 3.452(3) 153
C10 H10B O4 7_755 0.97 2.45 3.202(3) 134
N2 H1N O3 5_666 0.85(3) 2.02(3) 2.875(3) 175(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C9 O4 . . . . -166.4(2) ?
C7 N1 C9 O4 . . . . 12.1(3) ?
C6 N1 C9 C10 . . . . 15.7(3) ?
C7 N1 C9 C10 . . . . -165.86(19) ?
C9 N1 C7 C8 . . . . 136.4(2) ?
C6 N1 C7 C8 . . . . -44.9(3) ?
O3 C8 C7 N1 . . . . -159.2(2) ?
N2 C8 C7 N1 . . . . 22.2(3) ?
O3 C8 N2 C1 . . . . -168.6(2) ?
C7 C8 N2 C1 . . . . 10.0(3) ?
C2 C1 N2 C8 . . . . 158.4(2) ?
C6 C1 N2 C8 . . . . -21.2(3) ?
O4 C9 C10 S1 . . . . -43.2(3) ?
N1 C9 C10 S1 . . . . 134.71(18) ?
C11 S1 C10 C9 . . . . -78.50(18) ?
C4 C5 C6 C1 . . . . 5.8(4) ?
C4 C5 C6 N1 . . . . -176.6(2) ?
C2 C1 C6 C5 . . . . -4.4(3) ?
N2 C1 C6 C5 . . . . 175.2(2) ?
C2 C1 C6 N1 . . . . 177.8(2) ?
N2 C1 C6 N1 . . . . -2.6(3) ?
C9 N1 C6 C5 . . . . 36.4(3) ?
C7 N1 C6 C5 . . . . -142.1(2) ?
C9 N1 C6 C1 . . . . -145.9(2) ?
C7 N1 C6 C1 . . . . 35.6(3) ?
C4 C3 C2 C1 . . . . 2.5(4) ?
C6 C1 C2 C3 . . . . 0.2(4) ?
N2 C1 C2 C3 . . . . -179.4(2) ?
C13 C12 C11 S1 . . . . 114.1(3) ?
C17 C12 C11 S1 . . . . -62.9(4) ?
C10 S1 C11 C12 . . . . -54.1(2) ?
C2 C3 C4 C5 . . . . -1.1(4) ?
C6 C5 C4 C3 . . . . -3.1(4) ?
C17 C12 C13 C14 . . . . -1.1(5) ?
C11 C12 C13 C14 . . . . -178.1(3) ?
C12 C13 C14 C15 . . . . 1.0(6) ?
C13 C12 C17 C16 . . . . -0.4(6) ?
C11 C12 C17 C16 . . . . 176.6(4) ?
C15 C16 C17 C12 . . . . 2.1(9) ?
C17 C16 C15 C14 . . . . -2.3(10) ?
C13 C14 C15 C16 . . . . 0.7(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1997396
