#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:57:45 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/22/7232230.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_7232230
loop_
_publ_author_name
'Tarai, Arup'
'Baruah, Jubaraj Bikash'
_publ_section_title
;
 Separation or combination of non-covalently linked partners provides
 polymorphs of N-(aryl)-2-(propan-2-ylidene)hydrazine carbothioamides
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1397
_journal_paper_doi               10.1039/C8CE02000K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C10 H12 N4 O2 S'
_chemical_formula_sum            'C10 H12 N4 O2 S'
_chemical_formula_weight         252.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-17 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1690(12)
_cell_length_b                   4.4889(4)
_cell_length_c                   20.4829(18)
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      3.25
_cell_volume                     1210.83(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15192
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         1.988
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       Needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0505
_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)+(0.0600P)²+0.0752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                1374
_reflns_number_total             2106
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce02000k2.cif
_cod_data_source_block           NitroPoly3
_cod_depositor_comments
'Adding full bibliography for 7232228--7232231.cif.'
_cod_database_code               7232230
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
S1 S 0.64821(11) 0.8773(4) 0.50665(11) 0.0880(7) Uani 1 1 d . .
C4 C 0.7694(4) 0.9731(13) 0.5188(4) 0.0634(18) Uani 1 1 d . .
C7 C 0.8069(5) 0.3464(17) 0.3509(3) 0.0748(18) Uani 1 1 d . .
H7 H 0.7542 0.2685 0.3259 0.090 Uiso 1 1 calc R U
C5 C 0.8649(4) 0.6627(12) 0.4373(3) 0.0573(14) Uani 1 1 d . .
C6 C 0.7861(5) 0.5402(17) 0.4013(4) 0.0766(19) Uani 1 1 d . .
H6 H 0.7192 0.5888 0.4112 0.092 Uiso 1 1 calc R U
C8 C 0.9053(5) 0.2688(14) 0.3376(3) 0.0671(17) Uani 1 1 d . .
C2 C 0.9011(5) 1.4428(16) 0.6285(3) 0.0660(17) Uani 1 1 d . .
C10 C 0.9635(4) 0.5792(15) 0.4235(3) 0.0679(17) Uani 1 1 d . .
H10 H 1.0164 0.6560 0.4484 0.081 Uiso 1 1 calc R U
C9 C 0.9845(5) 0.3835(17) 0.3734(3) 0.0736(19) Uani 1 1 d . .
H9 H 1.0511 0.3301 0.3640 0.088 Uiso 1 1 calc R U
C3 C 1.0077(5) 1.5443(16) 0.6401(4) 0.084(2) Uani 1 1 d . .
H3A H 1.0509 1.4685 0.6062 0.126 Uiso 1 1 calc R U
H3B H 1.0306 1.4716 0.6817 0.126 Uiso 1 1 calc R U
H3C H 1.0099 1.7581 0.6400 0.126 Uiso 1 1 calc R U
C1 C 0.8202(6) 1.5412(17) 0.6744(4) 0.088(2) Uani 1 1 d . .
H1A H 0.7936 1.3715 0.6973 0.133 Uiso 1 1 calc R U
H1B H 0.7665 1.6357 0.6503 0.133 Uiso 1 1 calc R U
H1C H 0.8481 1.6799 0.7052 0.133 Uiso 1 1 calc R U
N3 N 0.8530(4) 0.8721(11) 0.4885(2) 0.0619(14) Uani 1 1 d . .
N2 N 0.7893(4) 1.1744(13) 0.5665(3) 0.0700(16) Uani 1 1 d . .
N1 N 0.8878(3) 1.2671(12) 0.5787(3) 0.0645(13) Uani 1 1 d . .
N4 N 0.9261(6) 0.0551(13) 0.2844(3) 0.0795(16) Uani 1 1 d . .
O2 O 1.0147(5) -0.0174(12) 0.2755(2) 0.0970(17) Uani 1 1 d . .
O1 O 0.8556(4) -0.0308(13) 0.2514(3) 0.1058(17) Uani 1 1 d . .
H2 H 0.734(4) 1.221(12) 0.588(3) 0.061(18) Uiso 1 1 d . .
H3 H 0.911(4) 0.949(11) 0.499(3) 0.051(16) Uiso 1 1 d . .
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
N3 C4 N2 113.6(5)
N3 C4 S1 128.8(6)
N2 C4 S1 117.6(5)
C8 C7 C6 119.9(6)
C10 C5 C6 119.2(6)
C10 C5 N3 115.8(5)
C6 C5 N3 125.0(5)
C7 C6 C5 120.0(6)
C7 C8 C9 121.1(6)
C7 C8 N4 119.1(7)
C9 C8 N4 119.8(7)
N1 C2 C1 125.3(6)
N1 C2 C3 115.9(6)
C1 C2 C3 118.8(6)
C9 C10 C5 120.9(6)
C8 C9 C10 118.9(6)
C4 N3 C5 131.1(5)
C4 N2 N1 120.7(6)
C2 N1 N2 116.8(5)
O1 N4 O2 124.2(7)
O1 N4 C8 118.5(7)
O2 N4 C8 117.2(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.672(6)
C4 N3 1.342(8)
C4 N2 1.356(9)
C7 C8 1.370(9)
C7 C6 1.378(10)
C5 C10 1.380(8)
C5 C6 1.386(9)
C5 N3 1.418(7)
C8 C9 1.375(9)
C8 N4 1.477(8)
C2 N1 1.300(8)
C2 C1 1.489(10)
C2 C3 1.494(9)
C10 C9 1.379(9)
N2 N1 1.385(7)
N4 O1 1.211(8)
N4 O2 1.226(8)
