Experimental and theoretical studies of the products of addition–elimination reactions between benzil dihydrazone and three isomeric chlorobenzaldehydes
Liu, Yun-Na; Cheng, Shuang-Shuang; Wang, Chao; Xing, Dian-Xiang; Liu, Yun; Tan, Xue-Jie; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615010682

data_2019986
_publ_section_title
;
 Experimental and theoretical studies of the products of
 addition--elimination reactions between benzil dihydrazone and three
 isomeric chlorobenzaldehydes
;
_journal_coeditor_code           LF3010
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615010682
_journal_volume                  71
_journal_year                    2015
_chemical_formula_moiety         'C28 H20 Cl2 N4'
_chemical_formula_sum            'C28 H20 Cl2 N4'
_chemical_formula_weight         483.38
_chemical_name_common
;
Benzil dihydrazone-<i>N</i>,<i>N</i>'-bis(4-chloro-1-formylbenzene)
;
_chemical_name_systematic
1-(4-Chlorobenzylidene)-2-{2-[2-(2-chlorobenzylidene)hydrazin-1-ylidene]-1,2-diphenylethylidene}hydrazine
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.040(7)
_cell_angle_beta                 109.532(7)
_cell_angle_gamma                93.954(7)
_cell_formula_units_Z            2
_cell_length_a                   9.661(5)
_cell_length_b                   11.492(6)
_cell_length_c                   13.018(7)
_cell_measurement_reflns_used    380
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.45
_cell_volume                     1241.6(11)
_computing_cell_refinement
;
SMART (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2001), PLATON (Spek, 2009)
and DIAMOND (Brandenburg & Putz, 1999)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6793
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_number         'not applicable to area detectors'
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.436
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                2699
_reflns_number_total             4757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lf3010sup1.cif
_cod_data_source_block           BDHPCB
_cod_original_cell_volume        1241.7(11)
_cod_database_code               2019986
_cod_database_fobs_code          2019986