#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/08/2210818.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_2210818
loop_
_publ_author_name
'Jian, Fangfang '
'Li, Ying '
_publ_section_title
;
 1-[1-(4-Methoxyphenyl)ethylidene]-4-phenylthiosemicarbazide ethanol
 hemisolvate
;
_journal_coeditor_code           WW2022
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4456
_journal_page_last               o4457
_journal_paper_doi               10.1107/S1600536806036415
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H17 N3 O1 S, 0.5C2 H6 O'
_chemical_formula_moiety         'C16 H17 N3 O1 S, 0.5C2 H6 O'
_chemical_formula_sum            'C17 H20 N3 O1.5 S'
_chemical_formula_weight         322.42
_chemical_name_systematic
;1-[1-(4-Methoxyphenyl)ethylidene]-4-phenylthiosemicarbazide ethanol
 hemisolvate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.50(3)
_cell_angle_beta                 84.83(3)
_cell_angle_gamma                87.53(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9360(10)
_cell_length_b                   11.674(2)
_cell_length_c                   13.962(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     896.5(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       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  0.0120
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3488
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.421
_refine_ls_extinction_coef       0.042(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.252
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0922
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2830
_refine_ls_wR_factor_ref         0.3143
_reflns_number_gt                2151
_reflns_number_total             3152
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2022.cif
_cod_data_source_block           I
_cod_database_code               2210818
_cod_database_fobs_code          2210818
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
S S1 0.94952(18) 0.12365(11) 0.58256(9) 0.0619(5) Uani d . 1
O O1 -0.2418(6) 0.3956(4) 0.0702(3) 0.0826(11) Uani d . 1
N N1 0.5746(6) 0.2585(3) 0.5218(3) 0.0630(10) Uani d . 1
H H1A 0.4635 0.2740 0.4833 0.076 Uiso calc R 1
C C1 0.7588(9) 0.3942(5) 0.5880(5) 0.0824(16) Uani d . 1
H H1B 0.8903 0.3932 0.5467 0.099 Uiso calc R 1
O O2 0.0000 0.0000 0.0000 0.255(6) Uiso d SD 1
N N2 0.6810(5) 0.1251(3) 0.4417(3) 0.0501(9) Uani d . 1
H H2A 0.7610 0.0650 0.4348 0.060 Uiso calc R 1
C C2 0.7493(10) 0.4638(6) 0.6484(5) 0.0916(19) Uani d . 1
H H2B 0.8764 0.5079 0.6480 0.110 Uiso calc R 1
N N3 0.5045(5) 0.1751(3) 0.3808(3) 0.0501(8) Uani d . 1
C C3 0.5631(10) 0.4711(5) 0.7084(5) 0.0815(16) Uani d . 1
H H3B 0.5572 0.5198 0.7484 0.098 Uiso calc R 1
C C4 0.3793(11) 0.4011(7) 0.7072(6) 0.114(2) Uani d . 1
H H4A 0.2493 0.4016 0.7495 0.137 Uiso calc R 1
C C5 0.3820(9) 0.3334(6) 0.6477(5) 0.0940(19) Uani d . 1
H H5A 0.2531 0.2914 0.6467 0.113 Uiso calc R 1
C C6 0.5773(7) 0.3258(4) 0.5873(4) 0.0588(11) Uani d . 1
C C7 0.7244(6) 0.1731(4) 0.5123(3) 0.0496(10) Uani d . 1
C C8 0.4737(6) 0.1409(4) 0.3060(3) 0.0493(10) Uani d . 1
C C9 0.6168(8) 0.0469(4) 0.2780(4) 0.0681(13) Uani d . 1
H H9A 0.6381 -0.0239 0.3392 0.102 Uiso calc R 1
H H9B 0.7612 0.0816 0.2469 0.102 Uiso calc R 1
H H9C 0.5427 0.0228 0.2301 0.102 Uiso calc R 1
C C10 0.2842(7) 0.2042(4) 0.2426(3) 0.0483(10) Uani d . 1
C C11 0.1190(7) 0.2678(4) 0.2807(3) 0.0517(10) Uani d . 1
H H11A 0.1246 0.2686 0.3468 0.062 Uiso calc R 1
C C12 -0.0539(7) 0.3302(4) 0.2215(3) 0.0592(11) Uani d . 1
H H12A -0.1626 0.3729 0.2479 0.071 Uiso calc R 1
C C13 -0.0661(7) 0.3294(4) 0.1230(3) 0.0583(11) Uani d . 1
C C14 0.0926(8) 0.2651(5) 0.0853(4) 0.0683(13) Uani d . 1
H H14A 0.0853 0.2630 0.0197 0.082 Uiso calc R 1
C C15 0.2642(8) 0.2030(4) 0.1455(4) 0.0648(12) Uani d . 1
H H15A 0.3702 0.1588 0.1194 0.078 Uiso calc R 1
C C16 -0.2723(11) 0.3942(6) -0.0275(4) 0.098(2) Uani d . 1
H H16A -0.4029 0.4431 -0.0538 0.147 Uiso calc R 1
H H16B -0.2937 0.3111 -0.0223 0.147 Uiso calc R 1
H H16C -0.1411 0.4276 -0.0734 0.147 Uiso calc R 1
C C17 0.2291(19) -0.034(2) 0.0154(17) 0.169(8) Uiso d PD 0.50
C C18 0.195(5) -0.108(3) 0.1300(18) 0.230(12) Uiso d PD 0.50
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O1 C16 . 119.2(4) yes
C7 N1 C6 . 127.8(3) yes
C7 N1 H1A . 116.1 ?
C6 N1 H1A . 116.1 ?
C2 C1 C6 . 120.9(5) ?
C2 C1 H1B . 119.5 ?
C6 C1 H1B . 119.5 ?
C17 O2 C17 2 180.0(18) ?
C7 N2 N3 . 118.1(3) yes
C7 N2 H2A . 120.9 ?
N3 N2 H2A . 120.9 ?
C3 C2 C1 . 122.5(5) ?
C3 C2 H2B . 118.7 ?
C1 C2 H2B . 118.7 ?
C8 N3 N2 . 119.7(3) yes
C2 C3 C4 . 116.1(5) ?
C2 C3 H3B . 122.0 ?
C4 C3 H3B . 122.0 ?
C5 C4 C3 . 122.9(6) ?
C5 C4 H4A . 118.6 ?
C3 C4 H4A . 118.6 ?
C4 C5 C6 . 120.1(5) ?
C4 C5 H5A . 120.0 ?
C6 C5 H5A . 120.0 ?
C1 C6 C5 . 117.4(4) ?
C1 C6 N1 . 122.9(4) ?
C5 C6 N1 . 119.4(4) ?
N1 C7 N2 . 114.9(3) yes
N1 C7 S1 . 124.7(3) yes
N2 C7 S1 . 120.4(3) yes
N3 C8 C10 . 115.4(3) yes
N3 C8 C9 . 124.6(4) yes
C10 C8 C9 . 120.0(3) ?
C8 C9 H9A . 109.5 ?
C8 C9 H9B . 109.5 ?
H9A C9 H9B . 109.5 ?
C8 C9 H9C . 109.5 ?
H9A C9 H9C . 109.5 ?
H9B C9 H9C . 109.5 ?
C15 C10 C11 . 117.2(4) ?
C15 C10 C8 . 122.6(4) ?
C11 C10 C8 . 120.2(4) ?
C12 C11 C10 . 120.8(4) ?
C12 C11 H11A . 119.6 ?
C10 C11 H11A . 119.6 ?
C11 C12 C13 . 120.4(4) ?
C11 C12 H12A . 119.8 ?
C13 C12 H12A . 119.8 ?
C14 C13 O1 . 124.8(4) ?
C14 C13 C12 . 119.4(4) ?
O1 C13 C12 . 115.8(4) ?
C13 C14 C15 . 119.5(4) ?
C13 C14 H14A . 120.2 ?
C15 C14 H14A . 120.2 ?
C10 C15 C14 . 122.6(4) ?
C10 C15 H15A . 118.7 ?
C14 C15 H15A . 118.7 ?
O1 C16 H16A . 109.5 ?
O1 C16 H16B . 109.5 ?
H16A C16 H16B . 109.5 ?
O1 C16 H16C . 109.5 ?
H16A C16 H16C . 109.5 ?
H16B C16 H16C . 109.5 ?
O2 C17 C18 . 96.9(16) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.684(4) yes
O1 C13 . 1.371(5) yes
O1 C16 . 1.398(6) yes
N1 C7 . 1.342(5) yes
N1 C6 . 1.408(5) yes
N1 H1A . 0.8600 ?
C1 C2 . 1.366(7) ?
C1 C6 . 1.371(6) ?
C1 H1B . 0.9300 ?
O2 C17 . 1.413(9) yes
O2 C17 2 1.413(9) ?
N2 C7 . 1.347(5) yes
N2 N3 . 1.381(4) yes
N2 H2A . 0.8600 ?
C2 C3 . 1.345(8) ?
C2 H2B . 0.9300 ?
N3 C8 . 1.277(5) yes
C3 C4 . 1.396(9) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.339(8) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.390(7) ?
C5 H5A . 0.9300 ?
C8 C10 . 1.491(5) ?
C8 C9 . 1.501(6) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C15 . 1.377(6) ?
C10 C11 . 1.389(6) ?
C11 C12 . 1.383(5) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.387(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.366(6) ?
C14 C15 . 1.383(6) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.513(10) ?
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
N1 H1A N3 ? 0.86 2.1365 2.566(5) 110.41 yes
N2 H2A S1 2_756 0.86 2.8021 3.660(4) 175.46 yes
C9 H9A S1 2_756 0.96 2.8009 3.464(5) 126.96 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
C6 C1 C2 C3 -1.2(10)
C7 N2 N3 C8 172.6(4)
C1 C2 C3 C4 1.1(10)
C2 C3 C4 C5 -2.2(11)
C3 C4 C5 C6 3.2(12)
C2 C1 C6 C5 2.1(9)
C2 C1 C6 N1 176.2(5)
C4 C5 C6 C1 -3.0(9)
C4 C5 C6 N1 -177.3(6)
C7 N1 C6 C1 54.7(7)
C7 N1 C6 C5 -131.3(6)
C6 N1 C7 N2 -178.8(4)
C6 N1 C7 S1 2.4(7)
N3 N2 C7 N1 5.9(5)
N3 N2 C7 S1 -175.2(3)
N2 N3 C8 C10 -177.7(3)
N2 N3 C8 C9 0.5(6)
N3 C8 C10 C15 162.5(4)
C9 C8 C10 C15 -15.7(6)
N3 C8 C10 C11 -17.3(6)
C9 C8 C10 C11 164.5(4)
C15 C10 C11 C12 -1.9(6)
C8 C10 C11 C12 178.0(4)
C10 C11 C12 C13 0.5(6)
C16 O1 C13 C14 3.4(7)
C16 O1 C13 C12 -176.8(5)
C11 C12 C13 C14 0.8(7)
C11 C12 C13 O1 -179.0(4)
O1 C13 C14 C15 179.1(5)
C12 C13 C14 C15 -0.7(7)
C11 C10 C15 C14 2.0(7)
C8 C10 C15 C14 -177.8(4)
C13 C14 C15 C10 -0.7(8)
