#------------------------------------------------------------------------------
#$Date: 2019-11-24 23:38:24 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/70/4517059.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_4517059
loop_
_publ_author_name
'Trzesowska-Kruszynska, Agata'
_publ_section_title
;
 Solvent-Free and Catalysis-Free Approach to the Solid State in Situ
 Growth of Crystalline Isoniazid Hydrazones
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3892
_journal_paper_doi               10.1021/cg400529s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C12 H11 N3 O S'
_chemical_formula_sum            'C12 H11 N3 O S'
_chemical_formula_weight         245.30
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.675(2)
_cell_angle_beta                 82.622(3)
_cell_angle_gamma                79.443(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9533(2)
_cell_length_b                   10.6197(4)
_cell_length_c                   14.3961(6)
_cell_measurement_reflns_used    167
_cell_measurement_temperature    291.0(3)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      2
_cell_volume                     570.99(4)
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_molecular_graphics
;XP in SHELXTL/PC (Sheldrick, 1990b)
 ORTEP-3 W v. 1.062 (Farrugia 1997)
;
_computing_publication_material
;SHELXL-97 (Sheldrick, 1997) and
 PLATON (Spek, 1990)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      291.0(3)
_diffrn_detector_area_resol_mean 1048576
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Kuma KM4-CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6600
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         69.56
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  33.33
_diffrn_standards_number         17
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED. STOE & Cie (1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.082
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0498P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2010
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400529s_si_002.cif
_cod_data_source_block           I
_cod_database_code               4517059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.0616(4) 0.27413(14) 0.86139(10) 0.0327(3) Uani 1 1 d .
C2 C 0.1238(4) 0.15660(15) 0.90964(12) 0.0413(4) Uani 1 1 d .
H2 H 0.1673 0.1436 0.9737 0.050 Uiso 1 1 calc R
C3 C 0.2433(5) 0.05893(16) 0.86106(14) 0.0496(4) Uani 1 1 d .
H3 H 0.3721 -0.0187 0.8940 0.060 Uiso 1 1 calc R
N1 N 0.1861(4) 0.06863(14) 0.77042(11) 0.0485(4) Uani 1 1 d .
C4 C 0.0023(5) 0.18153(17) 0.72557(12) 0.0453(4) Uani 1 1 d .
H4 H -0.0447 0.1902 0.6623 0.054 Uiso 1 1 calc R
C5 C -0.1232(4) 0.28662(15) 0.76651(11) 0.0398(4) Uani 1 1 d .
H5 H -0.2460 0.3639 0.7312 0.048 Uiso 1 1 calc R
C6 C -0.2140(4) 0.37436(14) 0.91749(11) 0.0365(3) Uani 1 1 d .
O1 O -0.3576(4) 0.33776(11) 0.99875(8) 0.0531(3) Uani 1 1 d .
N2 N -0.1954(4) 0.50326(12) 0.87842(9) 0.0389(3) Uani 1 1 d .
H2N H -0.3003 0.5561 0.9116 0.047 Uiso 1 1 d R
N3 N -0.0200(3) 0.54402(12) 0.78949(9) 0.0355(3) Uani 1 1 d .
C7 C -0.0186(4) 0.66910(14) 0.75594(10) 0.0323(3) Uani 1 1 d .
C12 C -0.1826(5) 0.77495(15) 0.80539(12) 0.0427(4) Uani 1 1 d .
H12A H -0.4293 0.7821 0.8087 0.064 Uiso 1 1 calc R
H12B H -0.1144 0.8577 0.7696 0.064 Uiso 1 1 calc R
H12C H -0.1096 0.7531 0.8696 0.064 Uiso 1 1 calc R
C8 C 0.1598(4) 0.70710(14) 0.65961(11) 0.0332(3) Uani 1 1 d .
S1 S 0.32836(12) 0.58972(4) 0.59650(3) 0.04547(17) Uani 1 1 d .
C9 C 0.2135(5) 0.83106(17) 0.60591(12) 0.0456(4) Uani 1 1 d .
H9 H 0.1410 0.9078 0.6273 0.055 Uiso 1 1 calc R
C10 C 0.3917(5) 0.82826(18) 0.51442(13) 0.0512(4) Uani 1 1 d .
H10 H 0.4487 0.9032 0.4690 0.061 Uiso 1 1 calc R
C11 C 0.4696(5) 0.70573(18) 0.50018(12) 0.0482(4) Uani 1 1 d .
H11 H 0.5872 0.6865 0.4441 0.058 Uiso 1 1 calc R
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'
N N 0.0311 0.0180 '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
C2 C1 C5 117.81(14)
C2 C1 C6 118.14(13)
C5 C1 C6 123.75(14)
C3 C2 C1 118.93(15)
C3 C2 H2 120.5
C1 C2 H2 120.5
N1 C3 C2 124.23(16)
N1 C3 H3 117.9
C2 C3 H3 117.9
C3 N1 C4 116.05(14)
N1 C4 C5 124.52(16)
N1 C4 H4 117.7
C5 C4 H4 117.7
C4 C5 C1 118.44(15)
C4 C5 H5 120.8
C1 C5 H5 120.8
O1 C6 N2 120.73(14)
O1 C6 C1 119.33(13)
N2 C6 C1 119.94(13)
C6 N2 N3 120.93(12)
C6 N2 H2N 115.7
N3 N2 H2N 123.4
C7 N3 N2 117.44(12)
N3 C7 C8 115.06(13)
N3 C7 C12 126.21(13)
C8 C7 C12 118.72(12)
C7 C12 H12A 109.5
C7 C12 H12B 109.5
H12A C12 H12B 109.5
C7 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C9 C8 C7 128.90(14)
C9 C8 S1 110.69(12)
C7 C8 S1 120.39(11)
C11 S1 C8 91.88(8)
C8 C9 C10 112.26(15)
C8 C9 H9 123.9
C10 C9 H9 123.9
C11 C10 C9 112.86(16)
C11 C10 H10 123.6
C9 C10 H10 123.6
C10 C11 S1 112.32(14)
C10 C11 H11 123.8
S1 C11 H11 123.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(2)
C1 C5 1.386(2)
C1 C6 1.498(2)
C2 C3 1.381(2)
C2 H2 0.9300
C3 N1 1.327(2)
C3 H3 0.9300
N1 C4 1.332(2)
C4 C5 1.382(2)
C4 H4 0.9300
C5 H5 0.9300
C6 O1 1.2296(19)
C6 N2 1.3472(19)
N2 N3 1.3770(17)
N2 H2N 0.8490
N3 C7 1.2887(19)
C7 C8 1.463(2)
C7 C12 1.493(2)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C8 C9 1.378(2)
C8 S1 1.7210(15)
S1 C11 1.7037(18)
C9 C10 1.417(3)
C9 H9 0.9300
C10 C11 1.345(3)
C10 H10 0.9300
C11 H11 0.9300
