The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
Yu, Haiyan; Wang, Meng; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 147–148; doi:10.1515/ncrs-2021-0407

data_8104985
_publ_section_title
;
 The crystal structure of
 N&#x2032;-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide
 monohydrate, C12H11ClN2O3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              147
_journal_page_last               148
_journal_paper_doi               10.1515/ncrs-2021-0407
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 Cl N2 O2 S, H2 O'
_chemical_formula_sum            'C12 H11 Cl N2 O3 S'
_chemical_formula_weight         298.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 96.286(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7305(8)
_cell_length_b                   21.252(4)
_cell_length_c                   13.134(2)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.413
_cell_measurement_theta_min      3.120
_cell_volume                     1312.5(4)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'APEX2-2008 [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 [3]'
_computing_structure_solution    'SHELXT 2018/3 [3]'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7324
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.831
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0664 before and 0.0325 after correction.
The Ratio of minimum to maximum transmission is 0.8451.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     231
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.3730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1745
_reflns_number_total             2659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0407_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104985
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C3-C4
 1.35 with sigma of 0.001
 C1-S1
 1.8 with sigma of 0.01
 C2A-C1A \\sim C2-C1
 with sigma of 0.02
 C5-C4 \\sim C5-C4A
 with sigma of 0.02
 S1A-C1A \\sim S1-C1
 with sigma of 0.02
 C4A-C3A \\sim C4-C3
 with sigma of 0.02
 S1A-C4A \\sim S1-C4
 with sigma of 0.02
3. Restrained planarity
 C3, C2, C1, C4, S1, C5
 with sigma of 0.1
 C2A, C1A, S1A, C3A, C4A, C5
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C4A \\sim S1A \\sim C1A \\sim C2A
\\sim C3A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
5. Rigid body (RIGU) restrains
 S1, C4, C3, C1, C2, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C4A, C3A, C2A, S1A, C1A, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C4A)=Sof(S1A)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(H2AA)=Sof(C3A)=Sof(H3A)=1-
 FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(C3)=Sof(H3)=Sof(C4)=FVAR(1)
7.a Free rotating group:
 O3(H3B,H3C)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2A), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11),
 C1A(H1AA), C2A(H2AA), C3A(H3A)
7.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
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