#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208238.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_2208238
loop_
_publ_author_name
'Fang, Xiao-Niu'
'Xu, Ya-Ping'
'Guo, Xue-Feng'
'Zeng, Xi-Rui'
_publ_section_title
;
 1,5-Bis[(1E)-(2-methoxyphenyl)methylene]thiocarbonohydrazide
 ethanol solvate
;
_journal_coeditor_code           AT6080
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1052
_journal_page_last               o1054
_journal_paper_doi               10.1107/S1600536806004983
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H18 N4 O2 S, C2 H6 O'
_chemical_formula_moiety         'C17 H18 N4 O2 S, C2 H6 O'
_chemical_formula_sum            'C19 H24 N4 O3 S'
_chemical_formula_weight         388.48
_chemical_melting_point          447.5
_chemical_name_systematic
;
1,5-Bis[(1E)-(2-methoxyphenyl)methylene]thiocarbonohydrazide
ethanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                87.547(2)
_cell_angle_beta                 74.645(2)
_cell_angle_gamma                83.177(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8197(8)
_cell_length_b                   10.3870(10)
_cell_length_c                   12.9400(10)
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.903
_cell_measurement_theta_min      2.548
_cell_volume                     1006.26(16)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    APEX2
_computing_publication_material  APEX2
_computing_structure_refinement  APEX2
_computing_structure_solution    APEX2
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II area-detector'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7920
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0514
_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)+(0.0373P)²+0.2726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2509
_reflns_number_total             3909
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6080.cif
_cod_data_source_block           I
_cod_original_cell_volume        1006.3(2)
_cod_database_code               2208238
_cod_database_fobs_code          2208238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O3 0.1078(3) 0.0508(2) 0.77124(18) 0.0911(7) Uani d . 1
H H3 0.0252 0.0982 0.8086 0.137 Uiso calc R 1
S S1 0.07210(10) 0.64717(6) 1.09751(5) 0.0693(3) Uani d . 1
N N4 0.1884(3) 0.9097(2) 1.0257(2) 0.0547(5) Uani d . 1
N N1 0.1300(3) 0.6982(2) 0.7897(2) 0.0619(5) Uani d . 1
C C10 0.2587(3) 1.0110(2) 0.9886(2) 0.0531(6) Uani d . 1
H H10 0.2839 1.0272 0.9152 0.064 Uiso calc R 1
O O1 0.3900(3) 1.2348(2) 0.9059(2) 0.0790(6) Uani d . 1
C C8 0.1283(4) 0.6219(2) 0.7152(2) 0.0647(7) Uani d . 1
H H8 0.1101 0.5357 0.7319 0.078 Uiso calc R 1
C C11 0.3019(3) 1.1040(2) 1.0576(2) 0.0542(6) Uani d . 1
C C16 0.3693(3) 1.2183(2) 1.0123(2) 0.0596(6) Uani d . 1
C C7 0.1542(4) 0.6670(3) 0.6051(2) 0.0680(7) Uani d . 1
O O2 0.2463(4) 0.4535(2) 0.5517(2) 0.1005(8) Uani d . 1
C C12 0.2815(4) 1.0809(3) 1.1653(2) 0.0714(7) Uani d . 1
H H12 0.2379 1.0049 1.1963 0.086 Uiso calc R 1
C C15 0.4128(4) 1.3067(3) 1.0761(3) 0.0769(8) Uani d . 1
H H15 0.4565 1.3832 1.0463 0.092 Uiso calc R 1
C C14 0.3912(4) 1.2808(3) 1.1826(3) 0.0890(10) Uani d . 1
H H14 0.4219 1.3397 1.2249 0.106 Uiso calc R 1
C C13 0.3255(4) 1.1703(3) 1.2283(2) 0.0872(9) Uani d . 1
H H13 0.3102 1.1546 1.3013 0.105 Uiso calc R 1
C C2 0.2088(4) 0.5772(3) 0.5212(2) 0.0770(8) Uani d . 1
C C6 0.1236(4) 0.7974(3) 0.5792(3) 0.0879(9) Uani d . 1
H H6 0.0904 0.8587 0.6332 0.106 Uiso calc R 1
C C3 0.2233(5) 0.6185(4) 0.4165(2) 0.0940(10) Uani d . 1
H H3A 0.2559 0.5585 0.3614 0.112 Uiso calc R 1
C C17 0.4418(5) 1.3553(3) 0.8576(3) 0.0940(10) Uani d . 1
H H17A 0.3572 1.4251 0.8924 0.141 Uiso calc R 1
H H17B 0.4451 1.3552 0.7829 0.141 Uiso calc R 1
H H17C 0.5580 1.3665 0.8651 0.141 Uiso calc R 1
C C5 0.1419(6) 0.8366(4) 0.4740(3) 0.1110(10) Uani d . 1
H H5 0.1218 0.9241 0.4572 0.133 Uiso calc R 1
C C1 0.3101(7) 0.3596(3) 0.4691(3) 0.125(2) Uani d . 1
H H1A 0.2190 0.3525 0.4331 0.188 Uiso calc R 1
H H1B 0.3398 0.2770 0.5001 0.188 Uiso calc R 1
H H1C 0.4143 0.3859 0.4187 0.188 Uiso calc R 1
C C4 0.1903(5) 0.7458(4) 0.3938(3) 0.1100(10) Uani d . 1
H H4 0.2004 0.7725 0.3231 0.131 Uiso calc R 1
C C18 0.2197(5) 0.1250(4) 0.6994(3) 0.1100(10) Uani d D 1
H H18A 0.2467 0.1956 0.7370 0.131 Uiso calc R 1
H H18B 0.1597 0.1624 0.6466 0.131 Uiso calc R 1
C C9 0.1094(3) 0.7139(2) 0.9750(2) 0.0543(6) Uani d . 1
N N2 0.0940(3) 0.6462(2) 0.8914(2) 0.0627(6) Uani d . 1
H H2 0.0612 0.5695 0.9022 0.075 Uiso calc R 1
N N3 0.1569(3) 0.8332(2) 0.9491(2) 0.0556(5) Uani d . 1
H H3B 0.1679 0.8623 0.8847 0.067 Uiso calc R 1
C C19 0.3872(6) 0.0482(6) 0.6444(5) 0.187(3) Uani d D 1
H H19A 0.4680 0.0405 0.6893 0.280 Uiso calc R 1
H H19B 0.4402 0.0907 0.5782 0.280 Uiso calc R 1
H H19C 0.3627 -0.0365 0.6297 0.280 Uiso calc R 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
_geom_angle_publ_flag
O1 C16 C15 123.6(2) ?
O1 C16 C11 116.4(2) ?
O1 C17 H17A 109.5 ?
O1 C17 H17B 109.5 ?
O1 C17 H17C 109.5 ?
O2 C1 H1A 109.5 ?
O2 C1 H1B 109.5 ?
O2 C1 H1C 109.5 ?
O2 C2 C3 124.9(3) ?
O2 C2 C7 115.0(3) ?
O3 C18 C19 111.8(4) ?
O3 C18 H18A 109.3 ?
O3 C18 H18B 109.3 ?
N1 N2 H2 119.6 ?
N1 C8 C7 121.2(2) y
N1 C8 H8 119.4 ?
N2 C9 S1 120.3(2) y
N3 C9 N2 114.3(2) y
N3 C9 S1 125.4(2) y
N4 N3 H3B 119.9 ?
N4 C10 C11 122.1(2) y
N4 C10 H10 118.9 ?
C2 C3 H3A 119.9 ?
C2 C7 C8 119.8(3) ?
C2 O2 C1 117.2(3) y
C3 C2 C7 120.1(3) ?
C3 C4 C5 120.9(3) ?
C3 C4 H4 119.5 ?
C4 C3 C2 120.3(3) ?
C4 C3 H3A 119.9 ?
C4 C5 H5 120.1 ?
C5 C4 H4 119.5 ?
C5 C6 C7 120.6(3) ?
C5 C6 H6 119.7 ?
C6 C5 C4 119.8(4) ?
C6 C5 H5 120.1 ?
C6 C7 C2 118.3(3) ?
C6 C7 C8 122.0(3) ?
C7 C6 H6 119.7 ?
C7 C8 H8 119.4 ?
C8 N1 N2 115.8(2) y
C9 N2 N1 120.9(2) y
C9 N2 H2 119.6 ?
C9 N3 N4 120.2(2) y
C9 N3 H3B 119.9 ?
C10 N4 N3 114.3(2) y
C11 C10 H10 118.9 ?
C11 C12 C13 120.6(3) ?
C11 C12 H12 119.7 ?
C12 C11 C16 118.9(2) ?
C12 C11 C10 121.9(2) ?
C12 C13 H13 120.2 ?
C13 C12 H12 119.7 ?
C13 C14 C15 121.3(3) ?
C13 C14 H14 119.4 ?
C14 C15 C16 119.6(3) ?
C14 C15 H15 120.2 ?
C14 C13 C12 119.7(3) ?
C14 C13 H13 120.2 ?
C15 C16 C11 120.0(3) ?
C15 C14 H14 119.4 ?
C16 O1 C17 118.5(2) y
C16 C11 C10 119.2(2) ?
C16 C15 H15 120.2 ?
C18 O3 H3 109.5 ?
C18 C19 H19C 109.5 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
C19 C18 H18A 109.3 ?
C19 C18 H18B 109.3 ?
H1A C1 H1B 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
H17A C17 H17B 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
H18A C18 H18B 107.9 ?
H19A C19 H19B 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 1.349(3) y
O1 C17 1.428(3) y
O2 C2 1.350(4) y
O2 C1 1.426(3) y
O3 C18 1.376(4) y
O3 H3 0.8200 ?
S1 C9 1.670(3) y
N1 C8 1.277(3) y
N1 N2 1.372(3) y
N2 H2 0.8600 ?
N3 H3B 0.8600 ?
N4 C10 1.262(3) y
N4 N3 1.385(2) y
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.383(4) ?
C3 C4 1.351(5) ?
C3 H3A 0.9300 ?
C4 H4 0.9300 ?
C5 C4 1.379(5) ?
C5 H5 0.9300 ?
C6 C5 1.379(4) ?
C6 H6 0.9300 ?
C7 C6 1.389(4) ?
C7 C2 1.407(4) ?
C8 C7 1.451(4) ?
C8 H8 0.9300 ?
C9 N3 1.339(3) y
C9 N2 1.354(3) y
C10 C11 1.469(3) ?
C10 H10 0.9300 ?
C11 C12 1.373(4) ?
C11 C16 1.399(3) ?
C12 C13 1.391(4) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C13 1.361(4) ?
C14 H14 0.9300 ?
C15 C14 1.362(4) ?
C15 H15 0.9300 ?
C16 C15 1.389(3) ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 C19 1.471(4) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
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
_geom_hbond_publ_flag
N2 H2 S1 2_567 0.86 2.59 3.435(2) 168 yes
O3 H3 N4 2_567 0.82 2.35 3.013(3) 139 yes
N3 H3B O3 1_565 0.86 2.47 3.220(3) 146 yes
C10 H10 O3 1_565 0.93 2.58 3.319(3) 137 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179699
2 PubChem 139069099
