The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
Sun, Guo-Xiang; Min, Li-Jing; Han, Liang; Liu, Xing-Hai; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 129–131; doi:10.1515/ncrs-2021-0432

data_8104979
_publ_section_title
;
 The crystal structure of
 (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              129
_journal_page_last               131
_journal_paper_doi               10.1515/ncrs-2021-0432
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C13 H12 Cl N3'
_chemical_formula_sum            'C13 H12 Cl N3'
_chemical_formula_weight         245.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   28.7760(11)
_cell_length_b                   41.7393(17)
_cell_length_c                   8.5929(3)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.991
_cell_measurement_theta_min      1.719
_cell_volume                     10320.8(7)
_computing_molecular_graphics    'Olex2 [1]'
_computing_publication_material  'Olex2 [1]'
_computing_structure_refinement  'ShelXL [2]'
_computing_structure_solution    'ShelXS [3]'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9647
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.719
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             4096
_exptl_crystal_size_max          0.862
_exptl_crystal_size_mid          0.687
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 694 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0324P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.764
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                2155
_reflns_number_total             4032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0432_suppl.cif
_cod_data_source_block           a
_cod_database_code               8104979
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.796
_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 C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13),
 N5(H5), C15(H15), C16(H16), C17(H17), C19(H19), C21(H21), C22(H22), C24(H24),
 C25(H25)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C)
;