#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:17:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180498 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/67/7216728.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7216728
loop_
_publ_author_name
'Wan, Chong-Qing'
'Li, Ai-Min'
'Al-Thabaiti, Shaeel A.'
'El-Mosslamy, El-Sayed H.'
'Mak, Thomas C. W.'
_publ_section_title
;
 Efficient solvent-controlled crystallization of pure polymorphs of
 1-nitro-4-(4-nitrophenylmethylthio)benzene
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              8960
_journal_paper_doi               10.1039/C4CE00753K
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 104.928(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1653(7)
_cell_length_b                   17.4934(18)
_cell_length_c                   12.4757(13)
_cell_measurement_temperature    296(2)
_cell_volume                     1300.1(2)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29694
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_min         2.052
_exptl_absorpt_coefficient_mu    0.264
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             600
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0838
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1432P)²+0.4622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2643
_refine_ls_wR_factor_ref         0.2906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2105
_reflns_number_total             3098
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00753k2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7216727--7216731.cif.'
_cod_database_code               7216728
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4897(3) 0.50523(9) 0.65777(15) 0.0981(8) Uani 0.791(5) 1 d . U P A 1
C7' C 0.596(2) 0.5101(6) 0.6417(7) 0.042(3) Uani 0.209(5) 1 d D U P A 2
H7'1 H 0.5298 0.4696 0.5908 0.050 Uiso 0.209(5) 1 calc R U P A 2
H7'2 H 0.7018 0.5383 0.6111 0.050 Uiso 0.209(5) 1 calc R U P A 2
O1 O 1.4305(4) 0.40446(17) 1.0325(3) 0.0954(9) Uani 1 1 d . . . . .
O2 O 1.1954(5) 0.32678(17) 1.0678(3) 0.0985(9) Uani 1 1 d . . . . .
O3 O 0.0224(6) 0.78833(18) 0.2184(3) 0.1051(10) Uani 1 1 d . . . . .
O4 O -0.2459(5) 0.71313(17) 0.2248(2) 0.0981(9) Uani 1 1 d . . . . .
N1 N 1.2418(5) 0.37953(14) 1.0151(2) 0.0632(7) Uani 1 1 d . . . . .
N2 N -0.0547(5) 0.73617(17) 0.2611(2) 0.0724(8) Uani 1 1 d . . . . .
C1 C 1.0653(5) 0.41468(15) 0.9281(2) 0.0539(7) Uani 1 1 d . . . . .
C2 C 1.1119(6) 0.47884(17) 0.8760(3) 0.0650(8) Uani 1 1 d . . . . .
H2A H 1.2540 0.5008 0.8942 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9322(8) 0.51048(19) 0.7924(3) 0.0771(10) Uani 1 1 d . U . . .
H3A H 0.9555 0.5545 0.7552 0.093 Uiso 1 1 calc R U . . .
C4 C 0.7197(6) 0.4756(2) 0.7659(3) 0.0734(9) Uani 1 1 d D U . . .
C5 C 0.6877(6) 0.4121(2) 0.8219(3) 0.0783(10) Uani 1 1 d . . . . .
H5A H 0.5472 0.3890 0.8043 0.094 Uiso 1 1 calc R U . . .
C6 C 0.8532(6) 0.3818(2) 0.9020(3) 0.0687(8) Uani 1 1 d . . . . .
H6A H 0.8259 0.3387 0.9401 0.082 Uiso 1 1 calc R U . . .
S1' S 0.3980(13) 0.5682(7) 0.6669(7) 0.143(4) Uani 0.209(5) 1 d D U P A 2
C7 C 0.5225(12) 0.6055(3) 0.6529(6) 0.103(2) Uani 0.791(5) 1 d . U P A 1
H7A H 0.4938 0.6288 0.7185 0.124 Uiso 0.791(5) 1 calc R U P A 1
H7B H 0.6750 0.6178 0.6512 0.124 Uiso 0.791(5) 1 calc R U P A 1
C8 C 0.3572(8) 0.6366(2) 0.5488(3) 0.0857(11) Uani 1 1 d D U . . .
C9 C 0.4378(7) 0.6917(2) 0.4915(3) 0.0832(11) Uani 1 1 d . . . . .
H9A H 0.5864 0.7073 0.5170 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3077(6) 0.7239(2) 0.3990(3) 0.0723(9) Uani 1 1 d . . . . .
H10A H 0.3657 0.7613 0.3613 0.087 Uiso 1 1 calc R U . . .
C11 C 0.0868(5) 0.70058(16) 0.3607(2) 0.0592(7) Uani 1 1 d . . . . .
C12 C -0.0041(6) 0.6449(2) 0.4129(3) 0.0745(9) Uani 1 1 d . . . . .
H12A H -0.1521 0.6290 0.3861 0.089 Uiso 1 1 calc R U . . .
C13 C 0.1376(8) 0.6129(2) 0.5089(3) 0.0891(11) Uani 1 1 d . U . . .
H13A H 0.0820 0.5748 0.5466 0.107 Uiso 1 1 calc R U . . .
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
C4 S1 C7 104.0(2)
C4 C7' S1' 103.2(6)
C4 C7' H7'1 111.1
S1' C7' H7'1 111.1
C4 C7' H7'2 111.1
S1' C7' H7'2 111.1
H7'1 C7' H7'2 109.1
O2 N1 O1 122.0(3)
O2 N1 C1 119.4(3)
O1 N1 C1 118.7(3)
O3 N2 O4 122.4(3)
O3 N2 C11 118.6(3)
O4 N2 C11 119.0(3)
C2 C1 C6 122.0(3)
C2 C1 N1 119.5(3)
C6 C1 N1 118.5(3)
C1 C2 C3 116.7(3)
C1 C2 H2A 121.7
C3 C2 H2A 121.7
C4 C3 C2 120.4(3)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C5 C4 C3 119.1(3)
C5 C4 C7' 133.6(5)
C3 C4 C7' 103.8(5)
C5 C4 S1 116.1(3)
C3 C4 S1 124.7(3)
C6 C5 C4 121.7(4)
C6 C5 H5A 119.1
C4 C5 H5A 119.1
C5 C6 C1 120.1(3)
C5 C6 H6A 120.0
C1 C6 H6A 120.0
C7' S1' C8 101.4(5)
C8 C7 S1 108.9(3)
C8 C7 H7A 109.9
S1 C7 H7A 109.9
C8 C7 H7B 109.9
S1 C7 H7B 109.9
H7A C7 H7B 108.3
C9 C8 C13 118.6(3)
C9 C8 C7 116.2(4)
C13 C8 C7 125.2(4)
C9 C8 S1' 150.7(4)
C13 C8 S1' 90.7(4)
C10 C9 C8 121.7(4)
C10 C9 H9A 119.1
C8 C9 H9A 119.1
C9 C10 C11 119.2(4)
C9 C10 H10A 120.4
C11 C10 H10A 120.4
C12 C11 C10 122.2(3)
C12 C11 N2 118.7(3)
C10 C11 N2 119.2(3)
C11 C12 C13 116.6(3)
C11 C12 H12A 121.7
C13 C12 H12A 121.7
C8 C13 C12 121.6(4)
C8 C13 H13A 119.2
C12 C13 H13A 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.764(4)
S1 C7 1.769(5)
C7' C4 1.654(9)
C7' S1' 1.679(13)
C7' H7'1 0.9700
C7' H7'2 0.9700
O1 N1 1.209(4)
O2 N1 1.209(3)
O3 N2 1.214(4)
O4 N2 1.218(4)
N1 C1 1.460(4)
N2 C11 1.460(4)
C1 C2 1.364(4)
C1 C6 1.388(5)
C2 C3 1.424(5)
C2 H2A 0.9300
C3 C4 1.405(6)
C3 H3A 0.9300
C4 C5 1.353(6)
C5 C6 1.340(5)
C5 H5A 0.9300
C6 H6A 0.9300
S1' C8 1.864(7)
C7 C8 1.530(6)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.367(6)
C8 C13 1.380(6)
C9 C10 1.347(5)
C9 H9A 0.9300
C10 C11 1.383(5)
C10 H10A 0.9300
C11 C12 1.370(5)
C12 C13 1.404(5)
C12 H12A 0.9300
C13 H13A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B O3 0.97 2.66 3.509(7) 146.8 4_676
C5 H5A O4 0.93 2.53 3.427(5) 160.8 3_566
C2 H2A O1 0.93 2.54 3.431(4) 160.7 3_867
C2 H2A O1 0.93 2.54 3.431(4) 160.7 3_867
C5 H5A O4 0.93 2.53 3.427(5) 160.8 3_566
C7 H7B O3 0.97 2.66 3.509(7) 146.8 4_676
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
O2 N1 C1 C2 173.5(3)
O1 N1 C1 C2 -6.2(4)
O2 N1 C1 C6 -5.7(4)
O1 N1 C1 C6 174.5(3)
C6 C1 C2 C3 -0.5(5)
N1 C1 C2 C3 -179.7(3)
C1 C2 C3 C4 -0.7(5)
C2 C3 C4 C5 0.9(5)
C2 C3 C4 C7' -160.8(4)
C2 C3 C4 S1 -175.4(3)
S1' C7' C4 C5 92.7(8)
S1' C7' C4 C3 -109.6(8)
S1' C7' C4 S1 40.8(7)
C7 S1 C4 C5 150.5(4)
C7 S1 C4 C3 -33.2(5)
C7 S1 C4 C7' -68.9(9)
C3 C4 C5 C6 0.1(6)
C7' C4 C5 C6 155.1(6)
S1 C4 C5 C6 176.6(3)
C4 C5 C6 C1 -1.2(6)
C2 C1 C6 C5 1.4(5)
N1 C1 C6 C5 -179.4(3)
C4 C7' S1' C8 155.1(6)
C4 S1 C7 C8 169.9(5)
S1 C7 C8 C9 -138.3(5)
S1 C7 C8 C13 41.1(8)
S1 C7 C8 S1' 41.2(6)
C7' S1' C8 C9 -62.2(14)
C7' S1' C8 C13 116.8(7)
C7' S1' C8 C7 -63.1(7)
C13 C8 C9 C10 1.1(6)
C7 C8 C9 C10 -179.4(4)
S1' C8 C9 C10 180.0(9)
C8 C9 C10 C11 -0.2(6)
C9 C10 C11 C12 -0.9(5)
C9 C10 C11 N2 179.3(3)
O3 N2 C11 C12 176.1(3)
O4 N2 C11 C12 -3.1(4)
O3 N2 C11 C10 -4.1(4)
O4 N2 C11 C10 176.7(3)
C10 C11 C12 C13 0.9(5)
N2 C11 C12 C13 -179.3(3)
C9 C8 C13 C12 -1.1(6)
C7 C8 C13 C12 179.5(5)
S1' C8 C13 C12 179.4(5)
C11 C12 C13 C8 0.1(6)
