#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/41/2204186.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_2204186
loop_
_publ_author_name
'Ali, Hapipah'
'Halim, S. Nadiah A.'
'Khamis, Nur Ashikin'
'Yusof, M. Sukeri'
'Yamin, Bohari M.'
_publ_section_title
N-(p-Methoxybenzoyl)-N'-(o-methoxyphenyl)thiourea
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1497
_journal_page_last               o1498
_journal_paper_doi               10.1107/S1600536804018823
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H16 N2 O3 S'
_chemical_formula_moiety         'C16 H16 N2 O3 S'
_chemical_formula_sum            'C16 H16 N2 O3 S'
_chemical_formula_weight         316.37
_chemical_name_systematic
;
N-(p-Methoxybenzoyl)-N'-(o-methoxyphenyl)thiourea
;
_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           SHELXL97
_cell_angle_alpha                92.68(4)
_cell_angle_beta                 104.56(4)
_cell_angle_gamma                113.45(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8320(10)
_cell_length_b                   9.151(2)
_cell_length_c                   12.201(3)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      1.75
_cell_volume                     765.8(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8107
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9153
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       triangular
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.039
_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)+(0.0528P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                2927
_reflns_number_total             3149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6078.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        765.8(3)
_cod_database_code               2204186
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S1 0.48384(6) 0.40889(5) 0.15572(3) 0.05222(15) Uani d . 1 S
O1 1.08548(18) 0.82102(15) 0.24637(9) 0.0580(3) Uani d . 1 O
O2 1.2894(2) 0.93484(15) -0.21987(11) 0.0591(3) Uani d . 1 O
O3 0.81610(19) 0.77415(14) 0.48162(10) 0.0564(3) Uani d . 1 O
N1 0.80446(17) 0.62660(15) 0.12521(10) 0.0387(3) Uani d . 1 N
H1A 0.7386 0.5936 0.0539 0.046 Uiso calc R 1 H
N2 0.82360(18) 0.58730(15) 0.31194(10) 0.0424(3) Uani d . 1 N
H2A 0.9388 0.6637 0.3266 0.051 Uiso calc R 1 H
C1 1.0072(2) 0.69176(17) -0.05047(13) 0.0396(3) Uani d . 1 C
H1 0.9167 0.5856 -0.0580 0.048 Uiso calc R 1 H
C2 1.0888(2) 0.74035(19) -0.13741(13) 0.0444(3) Uani d . 1 C
H2 1.0562 0.6663 -0.2025 0.053 Uiso calc R 1 H
C3 1.2201(2) 0.90004(18) -0.12825(13) 0.0415(3) Uani d . 1 C
C4 1.2726(2) 1.00955(18) -0.03032(14) 0.0435(3) Uani d . 1 C
H4 1.3601 1.1164 -0.0239 0.052 Uiso calc R 1 H
C5 1.1936(2) 0.95859(18) 0.05779(13) 0.0427(3) Uani d . 1 C
H5 1.2311 1.0315 0.1244 0.051 Uiso calc R 1 H
C6 1.0591(2) 0.80033(17) 0.04867(12) 0.0369(3) Uani d . 1 C
C7 0.9872(2) 0.75296(17) 0.14842(12) 0.0396(3) Uani d . 1 C
C8 0.7146(2) 0.54660(17) 0.20346(12) 0.0360(3) Uani d . 1 C
C9 0.7695(2) 0.51734(18) 0.40713(12) 0.0393(3) Uani d . 1 C
C10 0.7723(2) 0.61863(19) 0.49694(12) 0.0418(3) Uani d . 1 C
C11 0.7300(2) 0.5566(2) 0.59318(13) 0.0510(4) Uani d . 1 C
H11 0.7278 0.6222 0.6529 0.061 Uiso calc R 1 H
C12 0.6914(3) 0.3974(2) 0.59989(15) 0.0576(5) Uani d . 1 C
H12 0.6646 0.3564 0.6650 0.069 Uiso calc R 1 H
C13 0.6916(3) 0.2984(2) 0.51239(16) 0.0575(4) Uani d . 1 C
H13 0.6656 0.1911 0.5183 0.069 Uiso calc R 1 H
C14 0.7307(2) 0.3587(2) 0.41473(14) 0.0490(4) Uani d . 1 C
H14 0.7307 0.2920 0.3548 0.059 Uiso calc R 1 H
C15 1.4042(3) 1.0982(2) -0.22563(19) 0.0648(5) Uani d . 1 C
H15A 1.3268 1.1582 -0.2310 0.097 Uiso calc R 1 H
H15B 1.4496 1.1024 -0.2920 0.097 Uiso calc R 1 H
H15C 1.5137 1.1444 -0.1578 0.097 Uiso calc R 1 H
C16 0.8343(3) 0.8855(2) 0.57519(18) 0.0678(5) Uani d . 1 C
H16A 0.7128 0.8504 0.5928 0.102 Uiso calc R 1 H
H16B 0.8680 0.9909 0.5541 0.102 Uiso calc R 1 H
H16C 0.9344 0.8897 0.6414 0.102 Uiso calc R 1 H
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
C3 O2 C15 119.37(14) ?
C10 O3 C16 117.73(14) ?
C7 N1 C8 127.74(12) yes
C7 N1 H1A 116.1 ?
C8 N1 H1A 116.1 ?
C8 N2 C9 126.65(12) yes
C8 N2 H2A 116.7 ?
C9 N2 H2A 116.7 ?
C2 C1 C6 120.41(13) ?
C2 C1 H1 119.8 ?
C6 C1 H1 119.8 ?
C1 C2 C3 120.16(14) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
O2 C3 C4 124.88(14) ?
O2 C3 C2 115.07(14) ?
C4 C3 C2 120.05(13) ?
C5 C4 C3 119.35(14) ?
C5 C4 H4 120.3 ?
C3 C4 H4 120.3 ?
C4 C5 C6 121.16(14) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C5 C6 C1 118.83(13) ?
C5 C6 C7 118.05(13) ?
C1 C6 C7 123.01(13) ?
O1 C7 N1 121.87(13) yes
O1 C7 C6 121.56(13) yes
N1 C7 C6 116.56(12) yes
N2 C8 N1 115.77(12) yes
N2 C8 S1 125.20(11) yes
N1 C8 S1 119.03(10) yes
C14 C9 C10 120.59(14) ?
C14 C9 N2 121.50(14) ?
C10 C9 N2 117.72(13) ?
O3 C10 C11 124.87(15) ?
O3 C10 C9 115.84(13) ?
C11 C10 C9 119.30(15) ?
C12 C11 C10 119.59(16) ?
C12 C11 H11 120.2 ?
C10 C11 H11 120.2 ?
C13 C12 C11 121.13(15) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C12 C13 C14 119.74(16) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C9 C14 C13 119.62(16) ?
C9 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O3 C16 H16A 109.5 ?
O3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.6681(15) yes
O1 C7 1.2225(18) yes
O2 C3 1.3587(18) yes
O2 C15 1.421(2) ?
O3 C10 1.359(2) ?
O3 C16 1.434(2) ?
N1 C7 1.3838(18) ?
N1 C8 1.3915(18) ?
N1 H1A 0.8600 ?
N2 C8 1.3236(18) ?
N2 C9 1.4279(18) ?
N2 H2A 0.8600 ?
C1 C2 1.375(2) ?
C1 C6 1.391(2) ?
C1 H1 0.9300 ?
C2 C3 1.391(2) ?
C2 H2 0.9300 ?
C3 C4 1.383(2) ?
C4 C5 1.381(2) ?
C4 H4 0.9300 ?
C5 C6 1.390(2) ?
C5 H5 0.9300 ?
C6 C7 1.478(2) ?
C9 C14 1.373(2) ?
C9 C10 1.392(2) ?
C10 C11 1.385(2) ?
C11 C12 1.376(3) ?
C11 H11 0.9300 ?
C12 C13 1.368(3) ?
C12 H12 0.9300 ?
C13 C14 1.389(2) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 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 H2A O1 1_555 0.86 1.93 2.630(2) 137 yes
N1 H1A S1 2_665 0.86 2.70 3.518(2) 159 yes
C14 H14 O2 2_765 0.93 2.52 3.431(2) 167 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 -1.8(2)
C15 O2 C3 C4 -8.9(2)
C15 O2 C3 C2 171.90(16)
C1 C2 C3 O2 -179.13(14)
C1 C2 C3 C4 1.6(2)
O2 C3 C4 C5 -179.14(14)
C2 C3 C4 C5 0.1(2)
C3 C4 C5 C6 -1.5(2)
C4 C5 C6 C1 1.2(2)
C4 C5 C6 C7 177.48(14)
C2 C1 C6 C5 0.4(2)
C2 C1 C6 C7 -175.60(14)
C8 N1 C7 O1 -7.8(2)
C8 N1 C7 C6 171.40(13)
C5 C6 C7 O1 -27.2(2)
C1 C6 C7 O1 148.90(16)
C5 C6 C7 N1 153.60(14)
C1 C6 C7 N1 -30.3(2)
C9 N2 C8 N1 -176.40(14)
C9 N2 C8 S1 3.2(2)
C7 N1 C8 N2 -6.3(2)
C7 N1 C8 S1 174.12(12)
C8 N2 C9 C14 64.4(2)
C8 N2 C9 C10 -120.54(17)
C16 O3 C10 C11 4.9(2)
C16 O3 C10 C9 -175.61(15)
C14 C9 C10 O3 178.70(14)
N2 C9 C10 O3 3.6(2)
C14 C9 C10 C11 -1.8(2)
N2 C9 C10 C11 -176.83(13)
O3 C10 C11 C12 -178.75(16)
C9 C10 C11 C12 1.8(2)
C10 C11 C12 C13 -0.8(3)
C11 C12 C13 C14 -0.2(3)
C10 C9 C14 C13 0.8(2)
N2 C9 C14 C13 175.65(15)
C12 C13 C14 C9 0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 769875
