#------------------------------------------------------------------------------
#$Date: 2022-06-08 04:18:06 +0200 (Wed 08 de Jun de 2022) $
#$Revision: 275903 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/41/2244109.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_2244109
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Khrustalev, Victor N.'
'Safronenko, Marina G.'
'Akkurt, Mehmet'
'Khalilov, Ali N.'
'Bhattarai, Ajaya'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2,2'-(phenylazanediyl)bis(1-phenylethan-1-one)
;
_journal_coeditor_code           TX2050
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022005382
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H19 N O2'
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_chemical_name_systematic
;
2,2'-(Phenylazanediyl)bis(1-phenylethan-1-one)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8269(2)
_cell_length_b                   9.09843(10)
_cell_length_c                   9.01580(10)
_cell_measurement_reflns_used    14002
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.99
_cell_measurement_theta_min      4.25
_cell_volume                     1708.42(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21247
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.366
_diffrn_reflns_theta_min         4.246
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0505
_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)+(0.0811P)²+0.6375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                1746
_reflns_number_total             1834
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2050sup1.cif
_cod_data_source_block           I
_cod_database_code               2244109
_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   0.944
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.38204(5) 0.42787(12) 0.14622(11) 0.0346(3) Uani d 1 . .
N N1 0.500000 0.50356(17) 0.250000 0.0275(4) Uani d 1 . .
C C1 0.500000 0.65552(19) 0.250000 0.0258(4) Uani d 1 . .
C C2 0.54585(7) 0.73540(15) 0.16825(14) 0.0312(3) Uani d 1 . .
H H2 0.577660 0.684521 0.112882 0.037 Uiso calc 1 . .
C C3 0.54488(9) 0.88824(18) 0.16798(17) 0.0432(4) Uani d 1 . .
H H3 0.575533 0.940593 0.110555 0.052 Uiso calc 1 . .
C C4 0.500000 0.9651(2) 0.250000 0.0537(7) Uani d 1 . .
H H4 0.499999 1.069489 0.250000 0.064 Uiso calc 1 . .
C C5 0.45804(6) 0.41853(14) 0.34384(14) 0.0256(3) Uani d 1 . .
H H5A 0.447899 0.476190 0.433961 0.031 Uiso calc 1 . .
H H5B 0.480651 0.328071 0.375413 0.031 Uiso calc 1 . .
C C6 0.39556(6) 0.37610(14) 0.26663(14) 0.0262(3) Uani d 1 . .
C C7 0.35248(6) 0.26878(14) 0.34230(13) 0.0256(3) Uani d 1 . .
C C8 0.36541(6) 0.21454(15) 0.48403(15) 0.0304(3) Uani d 1 . .
H H8 0.402012 0.248116 0.537005 0.036 Uiso calc 1 . .
C C9 0.32461(7) 0.11135(17) 0.54737(16) 0.0362(4) Uani d 1 . .
H H9 0.333629 0.073789 0.643461 0.043 Uiso calc 1 . .
C C10 0.27080(7) 0.06284(17) 0.47116(17) 0.0362(4) Uani d 1 . .
H H10 0.243425 -0.008843 0.514406 0.043 Uiso calc 1 . .
C C11 0.25697(7) 0.11905(17) 0.33172(16) 0.0353(4) Uani d 1 . .
H H11 0.219476 0.087802 0.280639 0.042 Uiso calc 1 . .
C C12 0.29775(7) 0.22064(15) 0.26696(16) 0.0316(3) Uani d 1 . .
H H12 0.288486 0.257788 0.170838 0.038 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 122.46(7) ?
C1 N1 C5 . 3_655 122.46(7) ?
C5 N1 C5 . 3_655 115.08(14) ?
N1 C1 C2 . 3_655 121.07(9) ?
N1 C1 C2 . . 121.07(9) ?
C2 C1 C2 3_655 . 117.86(17) ?
C3 C2 C1 . . 120.47(14) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 120.98(15) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C3 3_655 . 119.2(2) ?
C3 C4 H4 3_655 . 120.4 ?
C3 C4 H4 . . 120.4 ?
N1 C5 C6 . . 112.65(9) ?
N1 C5 H5A . . 109.1 ?
C6 C5 H5A . . 109.1 ?
N1 C5 H5B . . 109.1 ?
C6 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.8 ?
O1 C6 C7 . . 121.50(12) ?
O1 C6 C5 . . 120.45(11) ?
C7 C6 C5 . . 118.05(11) ?
C8 C7 C12 . . 119.44(12) ?
C8 C7 C6 . . 122.28(12) ?
C12 C7 C6 . . 118.27(12) ?
C9 C8 C7 . . 119.81(13) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C10 C9 C8 . . 120.38(13) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.97(13) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.05(13) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C7 . . 120.32(13) ?
C11 C12 H12 . . 119.8 ?
C7 C12 H12 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.2165(16) ?
N1 C1 . 1.383(2) ?
N1 C5 . 1.4415(14) ?
N1 C5 3_655 1.4416(14) ?
C1 C2 3_655 1.4082(16) ?
C1 C2 . 1.4082(16) ?
C2 C3 . 1.391(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.382(2) ?
C3 H3 . 0.9500 ?
C4 H4 . 0.9500 ?
C5 C6 . 1.5254(17) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.4913(18) ?
C7 C8 . 1.3960(19) ?
C7 C12 . 1.3973(19) ?
C8 C9 . 1.3892(19) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.388(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5A O1 7_566 0.99 2.51 3.4483(16) 158
C8 H8 Cg1 5_666 0.95 2.85 3.6963(14) 148
C8 H8 Cg1 8_565 0.95 2.85 3.6963(14) 148
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . 3_655 -6.40(9) ?
C5 N1 C1 C2 3_655 . . 3_655 173.60(9) ?
C5 N1 C1 C2 . . . . 173.59(9) ?
C5 N1 C1 C2 3_655 . . . -6.41(9) ?
N1 C1 C2 C3 . . . . 179.32(10) ?
C2 C1 C2 C3 3_655 . . . -0.68(10) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
C2 C3 C4 C3 . . . 3_655 -0.69(11) ?
C1 N1 C5 C6 . . . . 93.41(9) ?
C5 N1 C5 C6 3_655 . . . -86.59(9) ?
N1 C5 C6 O1 . . . . -8.70(17) ?
N1 C5 C6 C7 . . . . 170.61(11) ?
O1 C6 C7 C8 . . . . -176.33(12) ?
C5 C6 C7 C8 . . . . 4.37(18) ?
O1 C6 C7 C12 . . . . 4.30(19) ?
C5 C6 C7 C12 . . . . -175.00(11) ?
C12 C7 C8 C9 . . . . 1.3(2) ?
C6 C7 C8 C9 . . . . -178.06(12) ?
C7 C8 C9 C10 . . . . -0.6(2) ?
C8 C9 C10 C11 . . . . -0.9(2) ?
C9 C10 C11 C12 . . . . 1.7(2) ?
C10 C11 C12 C7 . . . . -1.0(2) ?
C8 C7 C12 C11 . . . . -0.6(2) ?
C6 C7 C12 C11 . . . . 178.84(12) ?

_cod_database_fobs_code 2244109
