#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211070.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_2211070
loop_
_publ_author_name
'Jing, Zuo-Liang'
'Zhang, Qiao-Zhen'
'Yu, Ming'
'Chen, Xin'
_publ_section_title
;N-(2-Hydroxy-3-methoxybenzylidene)-N'-(2-thienylcarbonyl)hydrazine
 monohydrate
;
_journal_coeditor_code           IS2069
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4894
_journal_page_last               o4895
_journal_paper_doi               10.1107/S1600536806040293
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H12 N2 O3 S , H2 O'
_chemical_formula_moiety         'C13 H12 N2 O3 S , H2 O'
_chemical_formula_sum            'C13 H14 N2 O4 S'
_chemical_formula_weight         294.32
_chemical_name_systematic
;
N-(2-Acetoxythiophene)(2-hydroxy-3-methoxybenzylidene)hydrazide monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8349(15)
_cell_length_b                   12.890(4)
_cell_length_c                   22.123(7)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      2.43
_cell_volume                     1378.7(7)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD 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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7249
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9290
_exptl_absorpt_correction_T_min  0.9200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.222
_refine_ls_abs_structure_details 'Flack (1983), with 975 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0396
_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)+(0.0526P)²+0.2691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2077
_reflns_number_total             2431
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2069.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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        1378.8(7)
_cod_database_code               2211070
_cod_database_fobs_code          2211070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+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
S S1 0.95279(19) 0.85930(6) 0.89975(3) 0.0677(3) Uani d . 1
O O1 0.5723(5) 0.90115(13) 0.80076(9) 0.0686(6) Uani d . 1
O O2 0.0182(4) 0.88869(13) 0.65587(9) 0.0527(5) Uani d . 1
H H2A 0.130(8) 0.877(3) 0.6850(16) 0.088(12) Uiso d . 1
O O3 -0.3423(4) 0.91297(14) 0.57055(9) 0.0595(5) Uani d . 1
N N1 0.4425(5) 0.73508(17) 0.78137(9) 0.0459(5) Uani d . 1
H H1A 0.454(6) 0.677(2) 0.7904(12) 0.052(8) Uiso d . 1
N N2 0.2606(5) 0.76270(15) 0.73657(9) 0.0456(5) Uani d . 1
C C1 1.1299(7) 0.7667(3) 0.93810(14) 0.0676(8) Uani d . 1
H H1 1.2580 0.7807 0.9684 0.081 Uiso calc R 1
C C2 1.0630(7) 0.6704(2) 0.91943(13) 0.0612(7) Uani d . 1
H H2 1.1406 0.6105 0.9356 0.073 Uiso calc R 1
C C3 0.8650(6) 0.66945(18) 0.87320(12) 0.0505(7) Uani d . 1
H H3 0.7971 0.6094 0.8553 0.061 Uiso calc R 1
C C4 0.7827(5) 0.76882(17) 0.85741(11) 0.0441(6) Uani d . 1
C C5 0.5911(6) 0.80750(18) 0.81098(11) 0.0463(6) Uani d . 1
C C6 0.1149(6) 0.6891(2) 0.71431(11) 0.0473(6) Uani d . 1
H H6 0.1393 0.6224 0.7293 0.057 Uiso calc R 1
C C7 -0.0872(5) 0.70538(17) 0.66655(11) 0.0429(6) Uani d . 1
C C8 -0.1253(5) 0.80234(17) 0.63951(11) 0.0414(6) Uani d . 1
C C9 -0.3236(5) 0.81363(18) 0.59371(11) 0.0447(6) Uani d . 1
C C10 -0.4790(6) 0.73024(19) 0.57500(12) 0.0492(6) Uani d . 1
H H10 -0.6085 0.7383 0.5443 0.059 Uiso calc R 1
C C11 -0.4424(6) 0.63371(19) 0.60205(12) 0.0522(6) Uani d . 1
H H11 -0.5495 0.5775 0.5899 0.063 Uiso calc R 1
C C12 -0.2470(6) 0.62167(18) 0.64692(12) 0.0515(7) Uani d . 1
H H12 -0.2212 0.5568 0.6644 0.062 Uiso calc R 1
C C13 -0.5562(7) 0.9327(2) 0.52843(14) 0.0684(8) Uani d . 1
H H13A -0.5237 0.8932 0.4923 0.103 Uiso calc R 1
H H13B -0.5593 1.0053 0.5187 0.103 Uiso calc R 1
H H13C -0.7307 0.9129 0.5456 0.103 Uiso calc R 1
O O4 0.5418(6) 1.01644(14) 0.69903(10) 0.0663(6) Uani d D 1
H H4A 0.666(7) 0.992(3) 0.6761(17) 0.099 Uiso d D 1
H H4B 0.510(9) 0.979(2) 0.7320(13) 0.099 Uiso d 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
_geom_angle_publ_flag
C1 S1 C4 92.12(15) ?
C8 O2 H2A 113(2) ?
C9 O3 C13 117.3(2) ?
C5 N1 N2 120.9(2) n
C5 N1 H1A 120(2) ?
N2 N1 H1A 119(2) ?
C6 N2 N1 116.0(2) n
C2 C1 S1 111.9(2) ?
C2 C1 H1 124.0 ?
S1 C1 H1 124.0 ?
C1 C2 C3 113.3(3) ?
C1 C2 H2 123.3 ?
C3 C2 H2 123.3 ?
C4 C3 C2 111.8(2) ?
C4 C3 H3 124.1 ?
C2 C3 H3 124.1 ?
C3 C4 C5 132.1(2) ?
C3 C4 S1 110.8(2) ?
C5 C4 S1 117.08(17) n
O1 C5 N1 123.4(3) n
O1 C5 C4 120.5(2) n
N1 C5 C4 116.1(2) ?
N2 C6 C7 122.9(2) n
N2 C6 H6 118.6 ?
C7 C6 H6 118.6 ?
C12 C7 C8 119.0(2) ?
C12 C7 C6 119.1(2) ?
C8 C7 C6 121.9(2) n
O2 C8 C7 123.4(2) n
O2 C8 C9 117.1(2) ?
C7 C8 C9 119.5(2) ?
C10 C9 O3 125.2(2) ?
C10 C9 C8 120.7(2) ?
O3 C9 C8 114.1(2) ?
C9 C10 C11 120.0(2) ?
C9 C10 H10 120.0 ?
C11 C10 H10 120.0 ?
C12 C11 C10 119.8(2) ?
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
C11 C12 C7 121.1(2) ?
C11 C12 H12 119.5 ?
C7 C12 H12 119.5 ?
O3 C13 H13A 109.5 ?
O3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
H4A O4 H4B 114(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.697(3) ?
S1 C4 1.707(3) n
O1 C5 1.232(3) n
O2 C8 1.361(3) n
O2 H2A 0.85(4) ?
O3 C9 1.382(3) ?
O3 C13 1.415(3) ?
N1 C5 1.348(3) n
N1 N2 1.372(3) n
N1 H1A 0.78(3) ?
N2 C6 1.280(3) n
C1 C2 1.347(4) ?
C1 H1 0.9300 ?
C2 C3 1.401(4) ?
C2 H2 0.9300 ?
C3 C4 1.386(3) ?
C3 H3 0.9300 ?
C4 C5 1.470(4) n
C6 C7 1.454(4) n
C6 H6 0.9300 ?
C7 C12 1.396(3) ?
C7 C8 1.398(3) n
C8 C9 1.402(3) ?
C9 C10 1.375(3) ?
C10 C11 1.392(3) ?
C10 H10 0.9300 ?
C11 C12 1.379(4) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
O4 H4A 0.85(3) ?
O4 H4B 0.89(2) ?
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
O4 H4B O1 . 0.89(2) 1.84(3) 2.701(3) 161(4) yes
O4 H4A O3 1_655 0.85(3) 2.55(3) 3.189(3) 133(4) yes
O4 H4A O2 1_655 0.85(3) 2.21(3) 2.988(3) 153(4) yes
N1 H1A O4 3_646 0.78(3) 2.08(3) 2.853(3) 171(3) yes
O2 H2A N2 . 0.85(4) 1.97(3) 2.683(3) 140(3) yes
C3 H3 O4 3_646 0.93 2.36 3.212(3) 152 yes
C6 H6 O4 3_646 0.93 2.60 3.374(3) 141 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
C5 N1 N2 C6 -175.1(2)
C4 S1 C1 C2 0.1(2)
S1 C1 C2 C3 0.0(3)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 177.6(3)
C2 C3 C4 S1 0.3(3)
C1 S1 C4 C3 -0.2(2)
C1 S1 C4 C5 -178.0(2)
N2 N1 C5 O1 0.9(4)
N2 N1 C5 C4 -179.1(2)
C3 C4 C5 O1 -172.0(3)
S1 C4 C5 O1 5.1(3)
C3 C4 C5 N1 8.0(4)
S1 C4 C5 N1 -174.88(19)
N1 N2 C6 C7 -180.0(2)
N2 C6 C7 C12 -176.9(2)
N2 C6 C7 C8 3.4(4)
C12 C7 C8 O2 179.4(2)
C6 C7 C8 O2 -0.9(4)
C12 C7 C8 C9 0.4(4)
C6 C7 C8 C9 -179.9(2)
C13 O3 C9 C10 6.4(4)
C13 O3 C9 C8 -173.9(2)
O2 C8 C9 C10 -179.4(2)
C7 C8 C9 C10 -0.4(4)
O2 C8 C9 O3 0.9(3)
C7 C8 C9 O3 180.0(2)
O3 C9 C10 C11 -179.7(2)
C8 C9 C10 C11 0.7(4)
C9 C10 C11 C12 -1.1(4)
C10 C11 C12 C7 1.1(4)
C8 C7 C12 C11 -0.7(4)
C6 C7 C12 C11 179.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178453
