#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229909.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_2229909
loop_
_publ_author_name
'Yao, Jin-hua'
'Guo, Bing'
'An, Kang'
'Guan, Jian-ning'
_publ_section_title
;
 5-(2-Methoxyphenyl)-1,3,4-thiadiazol-2-yl 2-methoxybenzoate
 hemihydrate
;
_journal_coeditor_code           BQ2283
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1046
_journal_paper_doi               10.1107/S1600536811010373
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H14 N2 O4 S, 0.5H2 O'
_chemical_formula_moiety         'C17 H14 N2 O4 S, 0.5(H2 O)'
_chemical_formula_sum            'C17 H15 N2 O4.5 S'
_chemical_formula_weight         356.37
_chemical_melting_point          520
_chemical_name_systematic
;
5-(2-Methoxyphenyl)-1,3,4-thiadiazol-2-yl 2-methoxybenzoate hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000
_cell_angle_beta                 95.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.858(6)
_cell_length_b                   14.542(3)
_cell_length_c                   7.6710(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     3317.1(12)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3108
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9363
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0633
_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)+(0.0980P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                1881
_reflns_number_total             3050
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2283.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C17 H15 N2 O4.5 S1'
_cod_database_code               2229909
_cod_database_fobs_code          2229909
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.05152(13) 0.3419(3) 0.6081(4) 0.0711(11) Uani d . 1 . .
H H1 0.0270 0.3110 0.6471 0.085 Uiso calc R 1 . .
C C2 0.04737(17) 0.3882(4) 0.4474(5) 0.0932(16) Uani d . 1 . .
H H2 0.0195 0.3907 0.3827 0.112 Uiso calc R 1 . .
C C3 0.08311(19) 0.4293(3) 0.3852(5) 0.0898(14) Uani d . 1 . .
H H3 0.0800 0.4570 0.2755 0.108 Uiso calc R 1 . .
C C4 0.12303(15) 0.4305(3) 0.4795(4) 0.0698(11) Uani d . 1 . .
H H4 0.1472 0.4607 0.4363 0.084 Uiso calc R 1 . .
C C5 0.12879(12) 0.3875(2) 0.6401(4) 0.0525(9) Uani d . 1 . .
C C6 0.09271(11) 0.3426(2) 0.7089(4) 0.0490(8) Uani d . 1 . .
C C7 0.09536(10) 0.2968(2) 0.8806(4) 0.0441(7) Uani d . 1 . .
C C8 0.10712(11) 0.2309(3) 1.1613(5) 0.0540(9) Uani d . 1 . .
C C9 0.16054(10) 0.2020(2) 1.4126(4) 0.0438(7) Uani d . 1 . .
C C10 0.16644(9) 0.1570(2) 1.5889(3) 0.0385(7) Uani d . 1 . .
C C11 0.20815(11) 0.1655(2) 1.6793(4) 0.0527(8) Uani d . 1 . .
H H11 0.2302 0.1989 1.6288 0.063 Uiso calc R 1 . .
C C12 0.21841(13) 0.1272(3) 1.8389(5) 0.0630(10) Uani d . 1 . .
H H12 0.2469 0.1350 1.8966 0.076 Uiso calc R 1 . .
C C13 0.18718(14) 0.0778(3) 1.9137(5) 0.0707(11) Uani d . 1 . .
H H13 0.1945 0.0503 2.0220 0.085 Uiso calc R 1 . .
C C14 0.14490(13) 0.0674(2) 1.8324(4) 0.0597(10) Uani d . 1 . .
H H14 0.1235 0.0336 1.8861 0.072 Uiso calc R 1 . .
C C15 0.13365(10) 0.1075(2) 1.6690(4) 0.0419(7) Uani d . 1 . .
C C16 0.20649(14) 0.4248(3) 0.6754(6) 0.1006(16) Uani d . 1 . .
H H16A 0.2114 0.3935 0.5687 0.151 Uiso calc R 1 . .
H H16B 0.2323 0.4173 0.7582 0.151 Uiso calc R 1 . .
H H16C 0.2017 0.4891 0.6517 0.151 Uiso calc R 1 . .
C C17 0.05776(12) 0.0530(3) 1.6602(5) 0.0806(13) Uani d . 1 . .
H H17A 0.0673 -0.0086 1.6895 0.121 Uiso calc R 1 . .
H H17B 0.0310 0.0510 1.5811 0.121 Uiso calc R 1 . .
H H17C 0.0517 0.0851 1.7649 0.121 Uiso calc R 1 . .
N N1 0.06100(9) 0.2548(2) 0.9303(3) 0.0558(8) Uani d . 1 . .
N N2 0.06703(10) 0.2169(2) 1.0882(4) 0.0720(9) Uani d . 1 . .
O O1 0.16829(8) 0.38751(17) 0.7453(3) 0.0615(7) Uani d . 1 . .
O O2 0.11766(6) 0.19761(15) 1.3039(3) 0.0518(6) Uani d . 1 . .
O O3 0.19112(7) 0.24147(19) 1.3498(3) 0.0691(8) Uani d . 1 . .
O O4 0.09264(7) 0.10003(17) 1.5783(3) 0.0561(6) Uani d . 1 . .
S S 0.14064(3) 0.29401(7) 1.03358(11) 0.0554(3) Uani d . 1 . .
O O1W 0.0000 0.1206(3) 0.2500 0.1159(19) Uani d S 1 . .
H H1W 0.019(3) 0.159(6) 0.167(12) 0.40(7) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.2(4) ?
C6 C1 H1 . . 120.4 ?
C2 C1 H1 . . 120.4 ?
C3 C2 C1 . . 121.0(4) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C3 C2 . . 120.7(4) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.7(4) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
O1 C5 C4 . . 124.0(3) ?
O1 C5 C6 . . 115.4(3) ?
C4 C5 C6 . . 120.6(4) ?
C1 C6 C5 . . 117.7(3) ?
C1 C6 C7 . . 117.8(3) ?
C5 C6 C7 . . 124.5(3) ?
N1 C7 C6 . . 120.2(3) ?
N1 C7 S . . 112.9(2) ?
C6 C7 S . . 126.9(2) ?
O2 C8 N2 . . 118.9(3) ?
O2 C8 S . . 127.5(3) ?
N2 C8 S . . 113.6(3) ?
O3 C9 O2 . . 116.4(3) ?
O3 C9 C10 . . 122.2(3) ?
O2 C9 C10 . . 121.3(2) ?
C11 C10 C15 . . 117.5(3) ?
C11 C10 C9 . . 116.3(3) ?
C15 C10 C9 . . 126.2(3) ?
C12 C11 C10 . . 122.6(3) ?
C12 C11 H11 . . 118.7 ?
C10 C11 H11 . . 118.7 ?
C13 C12 C11 . . 119.7(4) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.8(3) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.1(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
O4 C15 C14 . . 124.1(3) ?
O4 C15 C10 . . 116.8(3) ?
C14 C15 C10 . . 119.2(3) ?
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 ?
O4 C17 H17A . . 109.5 ?
O4 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O4 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C7 N1 N2 . . 115.0(3) ?
C8 N2 N1 . . 112.0(3) ?
C5 O1 C16 . . 117.3(3) ?
C8 O2 C9 . . 129.7(3) ?
C15 O4 C17 . . 118.0(3) ?
C7 S C8 . . 86.50(16) ?
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
C1 C6 . 1.392(5) ?
C1 C2 . 1.401(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.347(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.338(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(5) ?
C4 H4 . 0.9300 ?
C5 O1 . 1.367(4) ?
C5 C6 . 1.403(4) ?
C6 C7 . 1.472(4) ?
C7 N1 . 1.282(4) ?
C7 S . 1.709(3) ?
C8 O2 . 1.212(4) ?
C8 N2 . 1.291(4) ?
C8 S . 1.726(4) ?
C9 O3 . 1.214(3) ?
C9 O2 . 1.465(4) ?
C9 C10 . 1.499(4) ?
C10 C11 . 1.375(4) ?
C10 C15 . 1.401(4) ?
C11 C12 . 1.355(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.346(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.365(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.396(4) ?
C14 H14 . 0.9300 ?
C15 O4 . 1.357(4) ?
C16 O1 . 1.412(4) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 O4 . 1.437(4) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 N2 . 1.328(4) ?
O1W H1W . 1.05(8) ?
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
O1W H1W N2 1_554 1.05(9) 1.81(9) 2.821(4) 159(7) yes
C11 H11 O3 7_558 0.93 2.50 3.324(4) 148 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 3.4(7) ?
C1 C2 C3 C4 . . . . -3.2(8) ?
C2 C3 C4 C5 . . . . 1.9(7) ?
C3 C4 C5 O1 . . . . -178.6(4) ?
C3 C4 C5 C6 . . . . -0.8(6) ?
C2 C1 C6 C5 . . . . -2.3(5) ?
C2 C1 C6 C7 . . . . 177.3(3) ?
O1 C5 C6 C1 . . . . 179.0(3) ?
C4 C5 C6 C1 . . . . 1.0(5) ?
O1 C5 C6 C7 . . . . -0.5(5) ?
C4 C5 C6 C7 . . . . -178.4(3) ?
C1 C6 C7 N1 . . . . 2.8(5) ?
C5 C6 C7 N1 . . . . -177.7(3) ?
C1 C6 C7 S . . . . -175.8(3) ?
C5 C6 C7 S . . . . 3.7(5) ?
O3 C9 C10 C11 . . . . 2.2(5) ?
O2 C9 C10 C11 . . . . 179.9(3) ?
O3 C9 C10 C15 . . . . -177.7(3) ?
O2 C9 C10 C15 . . . . 0.1(5) ?
C15 C10 C11 C12 . . . . 0.9(5) ?
C9 C10 C11 C12 . . . . -179.0(3) ?
C10 C11 C12 C13 . . . . 0.7(6) ?
C11 C12 C13 C14 . . . . -1.4(6) ?
C12 C13 C14 C15 . . . . 0.7(6) ?
C13 C14 C15 O4 . . . . 179.4(3) ?
C13 C14 C15 C10 . . . . 0.9(5) ?
C11 C10 C15 O4 . . . . 179.8(3) ?
C9 C10 C15 O4 . . . . -0.4(4) ?
C11 C10 C15 C14 . . . . -1.6(4) ?
C9 C10 C15 C14 . . . . 178.2(3) ?
C6 C7 N1 N2 . . . . -179.3(3) ?
S C7 N1 N2 . . . . -0.5(4) ?
O2 C8 N2 N1 . . . . -177.8(3) ?
S C8 N2 N1 . . . . -0.1(4) ?
C7 N1 N2 C8 . . . . 0.4(5) ?
C4 C5 O1 C16 . . . . -7.5(5) ?
C6 C5 O1 C16 . . . . 174.6(3) ?
N2 C8 O2 C9 . . . . 179.1(3) ?
S C8 O2 C9 . . . . 1.8(5) ?
O3 C9 O2 C8 . . . . -3.4(5) ?
C10 C9 O2 C8 . . . . 178.8(3) ?
C14 C15 O4 C17 . . . . 4.1(5) ?
C10 C15 O4 C17 . . . . -177.4(3) ?
N1 C7 S C8 . . . . 0.4(3) ?
C6 C7 S C8 . . . . 179.1(3) ?
O2 C8 S C7 . . . . 177.3(4) ?
N2 C8 S C7 . . . . -0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656623
