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#$Date: 2022-05-05 11:20:55 +0300 (Thu, 05 May 2022) $
#$Revision: 274918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105152.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_8105152
loop_
_publ_author_name
'Al-Obaid, Abdulrahman M.'
'Syed, Saeed Ali'
'Ahmed, Bari'
'Hosten, Eric C.'
_publ_section_title
;
 The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one -- dimethyl
 sulfoxide (1/1), C8H6N4O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              501
_journal_page_last               502
_journal_paper_doi               10.1515/ncrs-2019-0806
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C8 H6 N4 O3, C2 H6 O S'
_chemical_formula_sum            'C10 H12 N4 O4 S'
_chemical_formula_weight         284.30
_chemical_name_systematic        (Z)-3-hydrazono-5-nitroindolin-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4813(5)
_cell_length_b                   6.8663(4)
_cell_length_c                   17.2605(9)
_cell_measurement_reflns_used    4979
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.97
_cell_volume                     1242.20(11)
_computing_cell_refinement       'Bruker [1]'
_computing_data_collection       'Bruker [1]'
_computing_data_reduction        'Bruker [1]'
_computing_molecular_graphics    'Ortep [5]'
_computing_publication_material  'PLATON [6] and MERCURY [7]'
_computing_structure_refinement  'SHELXL [3] and ShelXle [4]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8981
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker [1]'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0916P)²+0.6686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1384
_reflns_number_total             1674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0806_suppl.cif
_cod_data_source_block           ha019
_cod_database_code               8105152
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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 -0.05098(7) 0.250000 0.56168(4) 0.0447(3) Uani 1 2 d S T P . .
O1 O 0.3589(2) 0.250000 0.68248(12) 0.0479(6) Uani 1 2 d S T P . .
O2 O 0.6559(2) 0.250000 0.24584(12) 0.0539(6) Uani 1 2 d S T P . .
O3 O 0.7985(2) 0.250000 0.33372(15) 0.0707(9) Uani 1 2 d S T P . .
O4 O 0.0730(2) 0.250000 0.51749(13) 0.0527(6) Uani 1 2 d S T P . .
N1 N 0.3274(2) 0.250000 0.54961(13) 0.0332(5) Uani 1 2 d S T P . .
N2 N 0.6375(2) 0.250000 0.63323(13) 0.0378(5) Uani 1 2 d S T P . .
N3 N 0.6233(3) 0.250000 0.70888(15) 0.0521(7) Uani 1 2 d S T P . .
N4 N 0.6877(2) 0.250000 0.31372(14) 0.0392(6) Uani 1 2 d S T P . .
C1 C 0.3996(3) 0.250000 0.61516(15) 0.0347(6) Uani 1 2 d S T P . .
C2 C 0.5344(3) 0.250000 0.59057(15) 0.0316(6) Uani 1 2 d S T P . .
C3 C -0.0408(3) 0.4452(4) 0.62820(14) 0.0580(7) Uani 1 1 d . . . . .
H3C H -0.048602 0.568965 0.600326 0.087 Uiso 1 1 calc R U . . .
H3D H 0.041743 0.440482 0.654862 0.087 Uiso 1 1 calc R U . . .
H3E H -0.109724 0.434361 0.666293 0.087 Uiso 1 1 calc R U . . .
C11 C 0.4037(2) 0.250000 0.48397(14) 0.0274(5) Uani 1 2 d S T P . .
C12 C 0.5330(2) 0.250000 0.50603(14) 0.0263(5) Uani 1 2 d S T P . .
C13 C 0.6278(3) 0.250000 0.45057(14) 0.0298(5) Uani 1 2 d S T P . .
H13 H 0.715514 0.250000 0.464394 0.036 Uiso 1 2 calc R U P . .
C14 C 0.5891(3) 0.250000 0.37356(14) 0.0294(5) Uani 1 2 d S T P . .
C15 C 0.4622(3) 0.250000 0.35076(14) 0.0313(6) Uani 1 2 d S T P . .
H15 H 0.440573 0.250000 0.297315 0.038 Uiso 1 2 calc R U P . .
C16 C 0.3676(2) 0.250000 0.40660(15) 0.0316(5) Uani 1 2 d S T P . .
H16 H 0.280025 0.250000 0.392363 0.038 Uiso 1 2 calc R U P . .
H1 H 0.240(4) 0.250000 0.545(2) 0.062(12) Uiso 1 2 d S . P . .
H3A H 0.679(8) 0.250000 0.747(5) 0.16(3) Uiso 1 2 d S . P . .
H3B H 0.536(5) 0.250000 0.725(3) 0.070(13) Uiso 1 2 d S . P . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 S1 C3 106.04(11) . 7_565
O4 S1 C3 106.04(11) . .
C3 S1 C3 98.58(17) 7_565 .
C1 N1 C11 111.0(2) . .
C1 N1 H1 129(3) . .
C11 N1 H1 120(3) . .
C2 N2 N3 117.8(3) . .
N2 N3 H3A 132(5) . .
N2 N3 H3B 113(3) . .
H3A N3 H3B 116(6) . .
O3 N4 O2 122.4(3) . .
O3 N4 C14 118.5(2) . .
O2 N4 C14 119.1(2) . .
O1 C1 N1 126.1(3) . .
O1 C1 C2 126.9(3) . .
N1 C1 C2 107.1(2) . .
N2 C2 C12 124.9(2) . .
N2 C2 C1 129.0(2) . .
C12 C2 C1 106.1(2) . .
S1 C3 H3C 109.5 . .
S1 C3 H3D 109.5 . .
H3C C3 H3D 109.5 . .
S1 C3 H3E 109.5 . .
H3C C3 H3E 109.5 . .
H3D C3 H3E 109.5 . .
N1 C11 C16 128.9(3) . .
N1 C11 C12 109.5(2) . .
C16 C11 C12 121.5(2) . .
C13 C12 C11 120.4(2) . .
C13 C12 C2 133.3(2) . .
C11 C12 C2 106.3(2) . .
C12 C13 C14 117.0(2) . .
C12 C13 H13 121.5 . .
C14 C13 H13 121.5 . .
C15 C14 C13 123.5(2) . .
C15 C14 N4 118.5(2) . .
C13 C14 N4 118.0(2) . .
C16 C15 C14 119.3(2) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
C15 C16 C11 118.3(2) . .
C15 C16 H16 120.8 . .
C11 C16 H16 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O4 1.507(2) .
S1 C3 1.768(3) 7_565
S1 C3 1.768(3) .
O1 C1 1.238(3) .
O2 N4 1.218(3) .
O3 N4 1.212(4) .
N1 C1 1.361(4) .
N1 C11 1.387(3) .
N1 H1 0.92(5) .
N2 C2 1.308(3) .
N2 N3 1.314(3) .
N3 H3A 0.88(9) .
N3 H3B 0.96(5) .
N4 C14 1.462(3) .
C1 C2 1.475(4) .
C2 C12 1.459(3) .
C3 H3C 0.9800 .
C3 H3D 0.9800 .
C3 H3E 0.9800 .
C11 C16 1.388(3) .
C11 C12 1.407(3) .
C12 C13 1.380(4) .
C13 C14 1.390(3) .
C13 H13 0.9500 .
C14 C15 1.386(4) .
C15 C16 1.383(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
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
_geom_hbond_publ_flag
N1 H1 O4 0.92(5) 1.81(5) 2.724(3) 170(4) . yes
N3 H3A O1 0.88(9) 2.24(9) 3.101(4) 165(7) 4_556 yes
N3 H3B O1 0.96(5) 1.99(5) 2.808(4) 142(4) . yes
C3 H3C O4 0.98 2.40 3.289(3) 151 3_556 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C1 O1 180.000(1) . . . .
C11 N1 C1 C2 0.000(1) . . . .
N3 N2 C2 C12 180.000(1) . . . .
N3 N2 C2 C1 0.000(1) . . . .
O1 C1 C2 N2 0.000(1) . . . .
N1 C1 C2 N2 180.000(1) . . . .
O1 C1 C2 C12 180.000(1) . . . .
N1 C1 C2 C12 0.000(1) . . . .
C1 N1 C11 C16 180.000(1) . . . .
C1 N1 C11 C12 0.000(1) . . . .
N1 C11 C12 C13 180.000(1) . . . .
C16 C11 C12 C13 0.000(1) . . . .
N1 C11 C12 C2 0.000(1) . . . .
C16 C11 C12 C2 180.000(1) . . . .
N2 C2 C12 C13 0.000(1) . . . .
C1 C2 C12 C13 180.000(1) . . . .
N2 C2 C12 C11 180.000(1) . . . .
C1 C2 C12 C11 0.000(1) . . . .
C11 C12 C13 C14 0.000(1) . . . .
C2 C12 C13 C14 180.000(1) . . . .
C12 C13 C14 C15 0.000(1) . . . .
C12 C13 C14 N4 180.000(0) . . . .
O3 N4 C14 C15 180.000(0) . . . .
O2 N4 C14 C15 0.000(0) . . . .
O3 N4 C14 C13 0.000(1) . . . .
O2 N4 C14 C13 180.000(0) . . . .
C13 C14 C15 C16 0.000(1) . . . .
N4 C14 C15 C16 180.000(0) . . . .
C14 C15 C16 C11 0.000(1) . . . .
N1 C11 C16 C15 180.000(1) . . . .
C12 C11 C16 C15 0.000(1) . . . .
