Experimental and computational evidence for stabilising parallel, offset π[C(O)N(H)NC]⋯π(phenyl) interactions in acetohydrazide derivatives
Tan, Sang Loon; Cardoso, Laura N. F.; de Souza, Marcus V. N.; Wardell, Solange M. S. V.; Wardell, James L.; Tiekink, Edward R. T.; CrystEngComm 24 (2022) 962–974; doi:10.1039/D1CE01492G

data_7244162
_publ_section_title
;
 Experimental and computational evidence for stabilising parallel, offset
 \p[C(&#xE001;O)N(H)N&#xE001;C]&#x22EF;\p(phenyl) interactions in
 acetohydrazide derivatives
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              962
_journal_page_last               974
_journal_paper_doi               10.1039/D1CE01492G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C13 H12 N2 O S'
_chemical_formula_sum            'C13 H12 N2 O S'
_chemical_formula_weight         244.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.2510(10)
_cell_angle_gamma                90
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_cell_length_b                   6.1737(2)
_cell_length_c                   20.5621(7)
_cell_measurement_reflns_used    7862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2379.68(14)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14482
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
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_diffrn_reflns_theta_min         3.483
_diffrn_source                   X-ray
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2733
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+3.2440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2135
_reflns_number_total             2733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01492g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7244036--7244162.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244162
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              35422