2-{(1<i>E</i>)-[(<i>E</i>)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study
Manawar, Rohit B.; Gondaliya, Mitesh B.; Shah, Manish K.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica Section E 75 (2019) 1423–1428; doi:10.1107/S2056989019012349

data_2243089
_publ_section_title
;
 2-{(1<i>E</i>)-[(<i>E</i>)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol:
 crystal structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           HB7852
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1423
_journal_page_last               1428
_journal_paper_doi               10.1107/S2056989019012349
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H10 Cl2 N2 O'
_chemical_formula_moiety         'C14 H10 Cl2 N2 O'
_chemical_formula_sum            'C14 H10 Cl2 N2 O'
_chemical_formula_weight         293.14
_chemical_name_systematic
;
2-{(1<i>E</i>)-[(<i>E</i>)-2-(2,6-Dichlorobenzylidene)hydrazin-1-\
ylidene]methyl}phenol
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.031(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5614(8)
_cell_length_b                   15.6055(12)
_cell_length_c                   10.0527(9)
_cell_measurement_reflns_used    4447
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.257
_cell_measurement_theta_min      4.831
_cell_volume                     1337.9(2)
_computing_cell_refinement
;
APEX2/SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10171
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'X-ray tube'
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0690P)^2^+0.4482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                2244
_reflns_number_total             3185
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7852sup1.cif
_cod_data_source_block           I
_cod_database_code               2243089
_cod_database_fobs_code          2243089
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.870
_shelx_hkl_checksum              13721
_shelx_res_checksum              3481