#------------------------------------------------------------------------------
#$Date: 2020-01-01 09:40:41 +0200 (Wed, 01 Jan 2020) $
#$Revision: 246406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/19/2021928.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021928
loop_
_publ_author_name
'Tan, Xue-Jie'
'Wang, Di'
'Hei, Xiao-Ming'
'Yang, Feng-Cun'
'Zhu, Ya-Ling'
'Xing, Dian-Xiang'
'Ma, Jian-Ping'
_publ_section_title
;
 Synthesis, crystal structures, antiproliferative activities and reverse
 docking studies of eight novel Schiff bases derived from benzil
;
_journal_coeditor_code           FP3080
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              44
_journal_page_last               63
_journal_paper_doi               10.1107/S2053229619015687
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C36 H26 N4'
_chemical_formula_moiety         'C36 H26 N4'
_chemical_formula_sum            'C36 H26 N4'
_chemical_formula_weight         514.61
_chemical_name_common
;
Benzil dihydrazone-N,N'-bis(1-formylnaphthalene)
;
_chemical_name_systematic
(1Z,2Z)-1,2-Bis{(E)-[(naphthalen-1-yl)methylidene]hydrazinylidene}-1,2-diphenylethane
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.230(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.195(8)
_cell_length_b                   9.809(3)
_cell_length_c                   11.806(4)
_cell_measurement_reflns_used    380
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.45
_cell_volume                     2744.1(15)
_computing_cell_refinement
;
SMART (Bruker, 2000)
;
_computing_data_collection
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2000), PLATON (Spek, 2009)
and DIAMOND (Brandenburg & Putz, 1999)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
and WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS2016 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.22
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6631
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.719
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0617
_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/[σ²(Fo²)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                1197
_reflns_number_total             2413
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fp3080sup1.cif
_cod_data_source_block           4-BDHFN
_cod_original_cell_volume        2744.2(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2021928
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.47469(10) 0.0592(3) 0.1862(2) 0.0498(7) Uani d 1
C C2 0.42618(10) -0.0283(3) 0.1669(2) 0.0492(7) Uani d 1
C C3 0.38212(11) -0.0443(3) 0.0497(3) 0.0657(8) Uani d 1
H H3 0.382634 0.002388 -0.018428 0.065(8) Uiso calc 1
C C4 0.33781(13) -0.1281(3) 0.0331(3) 0.0816(10) Uani d 1
H H4 0.308409 -0.137174 -0.046358 0.075(9) Uiso calc 1
C C5 0.33585(14) -0.1977(3) 0.1294(3) 0.0845(10) Uani d 1
H H5 0.305668 -0.255394 0.116304 0.074(9) Uiso calc 1
C C6 0.37835(14) -0.1830(3) 0.2459(4) 0.0864(10) Uani d 1
H H6 0.377201 -0.229986 0.313221 0.097(11) Uiso calc 1
C C7 0.42297(12) -0.0986(3) 0.2640(3) 0.0715(9) Uani d 1
H H7 0.451750 -0.088900 0.344135 0.052(7) Uiso calc 1
C C8 0.52380(14) 0.2815(3) 0.0423(3) 0.0670(8) Uani d 1
H H8 0.489868 0.285791 -0.029219 0.085(11) Uiso calc 1
C C9 0.56973(13) 0.3652(3) 0.0431(3) 0.0660(8) Uani d 1
C C10 0.55680(17) 0.4528(3) -0.0558(3) 0.0855(10) Uani d 1
H H10 0.520013 0.454005 -0.118007 0.117(14) Uiso calc 1
C C11 0.59585(18) 0.5391(4) -0.0671(4) 0.1027(12) Uani d 1
H H11 0.585478 0.598432 -0.134758 0.100(11) Uiso calc 1
C C12 0.65000(19) 0.5357(4) 0.0229(4) 0.1035(12) Uani d 1
H H12 0.676527 0.593874 0.015764 0.123(13) Uiso calc 1
C C13 0.66715(15) 0.4466(3) 0.1267(3) 0.0799(9) Uani d 1
C C14 0.62661(13) 0.3581(3) 0.1381(3) 0.0635(8) Uani d 1
C C15 0.64564(14) 0.2666(3) 0.2393(3) 0.0694(8) Uani d 1
H H15 0.619942 0.207560 0.248826 0.077(9) Uiso calc 1
C C16 0.70059(14) 0.2621(4) 0.3236(3) 0.0824(10) Uani d 1
H H16 0.712101 0.200221 0.389491 0.097(12) Uiso calc 1
C C17 0.73971(18) 0.3498(4) 0.3116(4) 0.1014(12) Uani d 1
H H17 0.777285 0.346277 0.369719 0.112(13) Uiso calc 1
C C18 0.72364(17) 0.4395(4) 0.2167(4) 0.1034(12) Uani d 1
H H18 0.750268 0.497894 0.210383 0.086(10) Uiso calc 1
N N1 0.47400(9) 0.1318(2) 0.0954(2) 0.0609(6) Uani d 1
N N2 0.52522(9) 0.2036(2) 0.1286(2) 0.0634(7) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . 119.5(2)
N1 C1 C1 2_655 121.5(2)
C2 C1 C1 2_655 118.9(2)
C7 C2 C3 . 117.3(3)
C7 C2 C1 . 121.5(2)
C3 C2 C1 . 121.3(3)
C4 C3 C2 . 120.5(3)
C4 C3 H3 . 119.8
C2 C3 H3 . 119.8
C5 C4 C3 . 121.3(3)
C5 C4 H4 . 119.3
C3 C4 H4 . 119.3
C4 C5 C6 . 119.4(3)
C4 C5 H5 . 120.3
C6 C5 H5 . 120.3
C5 C6 C7 . 119.8(3)
C5 C6 H6 . 120.1
C7 C6 H6 . 120.1
C2 C7 C6 . 121.7(3)
C2 C7 H7 . 119.2
C6 C7 H7 . 119.2
N2 C8 C9 . 126.7(3)
N2 C8 H8 . 116.7
C9 C8 H8 . 116.7
C10 C9 C14 . 119.5(3)
C10 C9 C8 . 116.4(3)
C14 C9 C8 . 124.0(3)
C9 C10 C11 . 123.0(4)
C9 C10 H10 . 118.5
C11 C10 H10 . 118.5
C12 C11 C10 . 118.6(4)
C12 C11 H11 . 120.7
C10 C11 H11 . 120.7
C11 C12 C13 . 122.1(4)
C11 C12 H12 . 118.9
C13 C12 H12 . 118.9
C18 C13 C12 . 121.9(4)
C18 C13 C14 . 119.0(3)
C12 C13 C14 . 119.0(3)
C15 C14 C13 . 117.5(3)
C15 C14 C9 . 124.7(3)
C13 C14 C9 . 117.7(3)
C16 C15 C14 . 121.6(3)
C16 C15 H15 . 119.2
C14 C15 H15 . 119.2
C15 C16 C17 . 120.2(4)
C15 C16 H16 . 119.9
C17 C16 H16 . 119.9
C18 C17 C16 . 120.5(4)
C18 C17 H17 . 119.8
C16 C17 H17 . 119.8
C17 C18 C13 . 121.1(4)
C17 C18 H18 . 119.4
C13 C18 H18 . 119.4
C1 N1 N2 . 111.8(2)
C8 N2 N1 . 112.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.280(3)
C1 C2 . 1.469(3)
C1 C1 2_655 1.525(4)
C2 C7 . 1.371(3)
C2 C3 . 1.382(3)
C3 C4 . 1.367(4)
C3 H3 . 0.9300
C4 C5 . 1.346(4)
C4 H4 . 0.9300
C5 C6 . 1.359(4)
C5 H5 . 0.9300
C6 C7 . 1.373(4)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 N2 . 1.261(3)
C8 C9 . 1.453(4)
C8 H8 . 0.9300
C9 C10 . 1.371(4)
C9 C14 . 1.434(3)
C10 C11 . 1.378(4)
C10 H10 . 0.9300
C11 C12 . 1.363(4)
C11 H11 . 0.9300
C12 C13 . 1.414(4)
C12 H12 . 0.9300
C13 C18 . 1.409(4)
C13 C14 . 1.422(4)
C14 C15 . 1.406(4)
C15 C16 . 1.357(4)
C15 H15 . 0.9300
C16 C17 . 1.390(4)
C16 H16 . 0.9300
C17 C18 . 1.343(4)
C17 H17 . 0.9300
C18 H18 . 0.9300
N1 N2 . 1.415(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15 N2 0.93 2.27 2.920(4) 126.1

_cod_database_fobs_code 2021928
