#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239467.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_2239467
loop_
_publ_author_name
'de Oliveira, Adriano Bof'
'Feitosa, Bárbara Regina Santos'
'Näther, Christian'
'Jess, Inke'
_publ_section_title
;
 4-Hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o278
_journal_paper_doi               10.1107/S1600536814002773
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C15 H15 N3 O2 S'
_chemical_formula_moiety         'C15 H15 N3 O2 S'
_chemical_formula_sum            'C15 H15 N3 O2 S'
_chemical_formula_weight         301.36
_chemical_name_common
;
4-Hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone
;
_chemical_name_systematic
;
3-[(4-Hydroxy-3-methoxybenzylidene)amino]-1-phenylthiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.008(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1010(5)
_cell_length_b                   8.7279(4)
_cell_length_c                   15.7921(7)
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.90
_cell_volume                     1477.88(12)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2008)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2008)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7883
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.181
_refine_ls_extinction_coef       0.0051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0343
_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)+(0.0283P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                2401
_reflns_number_total             2814
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6961sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239467
_cod_database_fobs_code          2239467
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_symmetry_multiplicity
C C1 0.09380(14) 0.31502(18) 0.38433(10) 0.0277(3) Uani d . 1 1
C C2 -0.00285(14) 0.23811(19) 0.32665(11) 0.0312(4) Uani d . 1 1
H H2 0.0098 0.1369 0.3085 0.037 Uiso calc R 1 1
C C3 -0.11786(14) 0.30837(19) 0.29539(11) 0.0308(4) Uani d . 1 1
H H3 -0.1842 0.2543 0.2569 0.037 Uiso calc R 1 1
C C4 -0.13632(14) 0.45689(19) 0.31995(10) 0.0289(3) Uani d . 1 1
C C5 -0.03748(14) 0.53832(18) 0.37529(10) 0.0277(3) Uani d . 1 1
C C6 0.07610(14) 0.46702(18) 0.40785(10) 0.0279(3) Uani d . 1 1
H H6 0.1426 0.5209 0.4463 0.033 Uiso calc R 1 1
O O1 -0.24864(10) 0.53058(14) 0.29167(8) 0.0384(3) Uani d . 1 1
H H1O1 -0.2957 0.4796 0.2513 0.058 Uiso calc R 1 1
O O2 -0.06289(10) 0.68653(13) 0.39208(8) 0.0354(3) Uani d . 1 1
C C7 0.03941(16) 0.7771(2) 0.43923(13) 0.0408(4) Uani d . 1 1
H H7A 0.0712 0.7353 0.4984 0.061 Uiso calc R 1 1
H H7B 0.0116 0.8829 0.4430 0.061 Uiso calc R 1 1
H H7C 0.1058 0.7754 0.4087 0.061 Uiso calc R 1 1
C C8 0.21140(14) 0.23577(18) 0.41893(11) 0.0298(4) Uani d . 1 1
H H8 0.2254 0.1416 0.3928 0.036 Uiso calc R 1 1
N N1 0.29680(11) 0.28779(15) 0.48318(9) 0.0283(3) Uani d . 1 1
N N2 0.40487(11) 0.20239(15) 0.50512(9) 0.0292(3) Uani d . 1 1
H H1N2 0.4160 0.1276 0.4706 0.035 Uiso calc R 1 1
C C9 0.49347(13) 0.23299(17) 0.57920(10) 0.0262(3) Uani d . 1 1
S S1 0.62845(4) 0.13258(5) 0.60149(3) 0.03137(14) Uani d . 1 1
N N3 0.46941(12) 0.34351(16) 0.63052(9) 0.0319(3) Uani d . 1 1
H H1N3 0.3955 0.3873 0.6159 0.038 Uiso calc R 1 1
C C10 0.55817(14) 0.39469(17) 0.70857(11) 0.0293(4) Uani d . 1 1
C C11 0.55360(17) 0.3387(3) 0.78865(12) 0.0442(5) Uani d . 1 1
H H11 0.4933 0.2639 0.7929 0.053 Uiso calc R 1 1
C C12 0.63836(19) 0.3927(3) 0.86368(13) 0.0574(6) Uani d . 1 1
H H12 0.6370 0.3536 0.9196 0.069 Uiso calc R 1 1
C C13 0.72416(17) 0.5025(3) 0.85702(14) 0.0530(6) Uani d . 1 1
H H13 0.7806 0.5408 0.9085 0.064 Uiso calc R 1 1
C C14 0.72884(18) 0.5569(2) 0.77684(15) 0.0501(5) Uani d . 1 1
H H14 0.7890 0.6319 0.7727 0.060 Uiso calc R 1 1
C C15 0.64570(16) 0.5026(2) 0.70154(13) 0.0407(4) Uani d . 1 1
H H15 0.6490 0.5395 0.6456 0.049 Uiso calc R 1 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
C2 C1 C6 119.54(14)
C2 C1 C8 118.90(14)
C6 C1 C8 121.57(14)
C3 C2 C1 120.26(15)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.26(14)
C4 C3 H3 119.9
C2 C3 H3 119.9
O1 C4 C3 122.45(14)
O1 C4 C5 117.57(14)
C3 C4 C5 119.98(14)
O2 C5 C6 124.74(14)
O2 C5 C4 115.64(13)
C6 C5 C4 119.62(14)
C5 C6 C1 120.26(14)
C5 C6 H6 119.9
C1 C6 H6 119.9
C4 O1 H1O1 109.5
C5 O2 C7 116.78(12)
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C1 122.57(15)
N1 C8 H8 118.7
C1 C8 H8 118.7
C8 N1 N2 115.18(13)
C9 N2 N1 120.24(13)
C9 N2 H1N2 119.9
N1 N2 H1N2 119.9
N3 C9 N2 117.17(13)
N3 C9 S1 123.73(11)
N2 C9 S1 119.10(12)
C9 N3 C10 123.17(13)
C9 N3 H1N3 118.4
C10 N3 H1N3 118.4
C11 C10 C15 120.93(16)
C11 C10 N3 120.05(15)
C15 C10 N3 119.01(16)
C10 C11 C12 119.19(19)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 120.0(2)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 120.46(18)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.98(19)
C13 C14 H14 120.0
C15 C14 H14 120.0
C10 C15 C14 119.41(19)
C10 C15 H15 120.3
C14 C15 H15 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(2)
C1 C6 1.405(2)
C1 C8 1.453(2)
C2 C3 1.387(2)
C2 H2 0.9500
C3 C4 1.383(2)
C3 H3 0.9500
C4 O1 1.3710(18)
C4 C5 1.406(2)
C5 O2 1.3645(19)
C5 C6 1.380(2)
C6 H6 0.9500
O1 H1O1 0.8400
O2 C7 1.425(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 N1 1.2792(19)
C8 H8 0.9500
N1 N2 1.3783(17)
N2 C9 1.3458(19)
N2 H1N2 0.8800
C9 N3 1.331(2)
C9 S1 1.6924(15)
N3 C10 1.4356(19)
N3 H1N3 0.8800
C10 C11 1.369(3)
C10 C15 1.378(2)
C11 C12 1.390(3)
C11 H11 0.9500
C12 C13 1.375(3)
C12 H12 0.9500
C13 C14 1.366(3)
C13 H13 0.9500
C14 C15 1.386(3)
C14 H14 0.9500
C15 H15 0.9500
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
O1 H1O1 S1 4_465 0.84 2.50 3.2844(13) 156.6
N2 H1N2 S1 3_656 0.88 2.53 3.3460(14) 154.5
N3 H1N3 O1 3_566 0.88 2.56 3.2068(18) 131.4
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 -2.8(3)
C8 C1 C2 C3 177.29(16)
C1 C2 C3 C4 1.4(3)
C2 C3 C4 O1 -179.19(16)
C2 C3 C4 C5 1.4(3)
O1 C4 C5 O2 -2.8(2)
C3 C4 C5 O2 176.67(15)
O1 C4 C5 C6 177.76(15)
C3 C4 C5 C6 -2.8(2)
O2 C5 C6 C1 -178.00(16)
C4 C5 C6 C1 1.4(2)
C2 C1 C6 C5 1.4(2)
C8 C1 C6 C5 -178.71(16)
C6 C5 O2 C7 6.7(2)
C4 C5 O2 C7 -172.72(15)
C2 C1 C8 N1 -167.58(16)
C6 C1 C8 N1 12.5(3)
C1 C8 N1 N2 -177.00(14)
C8 N1 N2 C9 -170.17(15)
N1 N2 C9 N3 2.5(2)
N1 N2 C9 S1 -176.66(11)
N2 C9 N3 C10 -176.04(15)
S1 C9 N3 C10 3.1(2)
C9 N3 C10 C11 -97.2(2)
C9 N3 C10 C15 84.1(2)
C15 C10 C11 C12 0.3(3)
N3 C10 C11 C12 -178.35(17)
C10 C11 C12 C13 1.0(3)
C11 C12 C13 C14 -1.5(3)
C12 C13 C14 C15 0.8(3)
C11 C10 C15 C14 -1.1(3)
N3 C10 C15 C14 177.63(16)
C13 C14 C15 C10 0.5(3)
