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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/04/8000457.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8000457
loop_
_publ_author_name
'Liu, Bin'
'Liu, Hao'
'Zhang, Houyu'
'Di, Qi'
'Zhang, Hongyu'
_publ_section_title
;
 Crystal Engineering of a Hydrazone Molecule toward High Elasticity and
 Bright Luminescence
;
_journal_name_full               'The Journal of Physical Chemistry Letters'
_journal_page_first              9178
_journal_page_last               9183
_journal_paper_doi               10.1021/acs.jpclett.0c02623
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 Cl N3 O'
_chemical_formula_sum            'C16 H16 Cl N3 O'
_chemical_formula_weight         301.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-08-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.169(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1980(9)
_cell_length_b                   13.1294(8)
_cell_length_c                   7.7881(5)
_cell_measurement_reflns_used    4433
_cell_measurement_temperature    148.04
_cell_measurement_theta_max      27.136
_cell_measurement_theta_min      3.064
_cell_volume                     1538.27(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      148.04
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19414
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0668
_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/[σ²(Fo²)+(0.0880P)²+0.3190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1904
_reflns_number_gt                1411
_reflns_number_total             2615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jz0c02623_si_002.cif
_cod_data_source_block           Cry-A
_cod_database_code               8000457
_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:
 N1(H1), C3(H3), C5(H5), C7(H7), C9(H9), C11(H11), C14(H14), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.18687(9) 0.91606(10) -0.01473(18) 0.1238(6) Uani 1 1 d . . .
N1 N -0.17840(17) 0.7705(2) -0.5273(4) 0.0635(8) Uani 1 1 d . . .
H1 H -0.1709 0.7446 -0.4220 0.076 Uiso 1 1 calc R . .
O2 O -0.11648(16) 0.85974(19) -0.7315(3) 0.0751(8) Uani 1 1 d . . .
C3 C -0.3031(2) 0.6775(3) -0.5933(4) 0.0606(9) Uani 1 1 d . . .
H3 H -0.2814 0.6383 -0.4938 0.073 Uiso 1 1 calc R . .
N4 N -0.25509(18) 0.7502(2) -0.6402(3) 0.0630(8) Uani 1 1 d . . .
C5 C 0.0459(3) 0.8574(3) -0.4766(5) 0.0747(11) Uani 1 1 d . . .
H5 H 0.0571 0.8462 -0.5920 0.090 Uiso 1 1 calc R . .
C6 C 0.0986(3) 0.8935(3) -0.1794(6) 0.0800(12) Uani 1 1 d . . .
C7 C -0.5166(2) 0.7008(3) -0.9006(5) 0.0652(10) Uani 1 1 d . . .
H7 H -0.5447 0.7489 -0.9815 0.078 Uiso 1 1 calc R . .
C8 C -0.0406(2) 0.8559(2) -0.4398(4) 0.0615(9) Uani 1 1 d . . .
C9 C -0.5147(3) 0.5400(3) -0.7547(5) 0.0690(10) Uani 1 1 d . . .
H9 H -0.5416 0.4765 -0.7355 0.083 Uiso 1 1 calc R . .
C10 C -0.5590(2) 0.6081(3) -0.8756(4) 0.0639(10) Uani 1 1 d . . .
C11 C -0.4345(2) 0.7225(3) -0.8086(5) 0.0622(9) Uani 1 1 d . . .
H11 H -0.4075 0.7861 -0.8269 0.075 Uiso 1 1 calc R . .
N12 N -0.6417(2) 0.5856(3) -0.9652(4) 0.0807(10) Uani 1 1 d . . .
C13 C -0.3896(2) 0.6542(3) -0.6891(4) 0.0566(9) Uani 1 1 d . . .
C14 C 0.0135(3) 0.8944(3) -0.1394(5) 0.0773(11) Uani 1 1 d . . .
H14 H 0.0024 0.9077 -0.0245 0.093 Uiso 1 1 calc R . .
C15 C -0.1146(2) 0.8309(3) -0.5804(5) 0.0618(9) Uani 1 1 d . . .
C16 C -0.0561(3) 0.8752(3) -0.2721(5) 0.0682(10) Uani 1 1 d . . .
H16 H -0.1155 0.8755 -0.2469 0.082 Uiso 1 1 calc R . .
C17 C -0.4327(2) 0.5635(3) -0.6630(5) 0.0672(10) Uani 1 1 d . . .
H17 H -0.4051 0.5163 -0.5798 0.081 Uiso 1 1 calc R . .
C18 C 0.1163(3) 0.8754(3) -0.3457(6) 0.0879(12) Uani 1 1 d . . .
H18 H 0.1758 0.8753 -0.3703 0.106 Uiso 1 1 calc R . .
C19 C -0.6805(3) 0.4854(3) -0.9477(6) 0.0927(14) Uani 1 1 d . . .
H19A H -0.6381 0.4327 -0.9714 0.139 Uiso 1 1 calc R . .
H19B H -0.7352 0.4790 -1.0305 0.139 Uiso 1 1 calc R . .
H19C H -0.6944 0.4771 -0.8294 0.139 Uiso 1 1 calc R . .
C20 C -0.6799(3) 0.6509(4) -1.1055(6) 0.1017(14) Uani 1 1 d . . .
H20A H -0.6841 0.7206 -1.0623 0.153 Uiso 1 1 calc R . .
H20B H -0.7395 0.6262 -1.1518 0.153 Uiso 1 1 calc R . .
H20C H -0.6422 0.6502 -1.1976 0.153 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N1 H1 120.3 . . ?
C15 N1 H1 120.3 . . ?
C15 N1 N4 119.4(3) . . ?
N4 C3 H3 119.3 . . ?
N4 C3 C13 121.4(3) . . ?
C13 C3 H3 119.3 . . ?
C3 N4 N1 115.0(3) . . ?
C8 C5 H5 119.8 . . ?
C8 C5 C18 120.4(4) . . ?
C18 C5 H5 119.8 . . ?
C14 C6 Cl1 118.9(4) . . ?
C14 C6 C18 122.0(4) . . ?
C18 C6 Cl1 119.1(4) . . ?
C10 C7 H7 119.7 . . ?
C11 C7 H7 119.7 . . ?
C11 C7 C10 120.5(3) . . ?
C5 C8 C15 119.3(3) . . ?
C16 C8 C5 119.2(3) . . ?
C16 C8 C15 121.5(3) . . ?
C10 C9 H9 119.4 . . ?
C17 C9 H9 119.4 . . ?
C17 C9 C10 121.2(3) . . ?
C9 C10 C7 117.4(3) . . ?
N12 C10 C7 121.3(3) . . ?
N12 C10 C9 121.3(3) . . ?
C7 C11 H11 118.9 . . ?
C7 C11 C13 122.2(3) . . ?
C13 C11 H11 118.9 . . ?
C10 N12 C19 119.9(3) . . ?
C10 N12 C20 119.7(3) . . ?
C20 N12 C19 118.8(3) . . ?
C11 C13 C3 121.9(3) . . ?
C17 C13 C3 121.3(3) . . ?
C17 C13 C11 116.9(3) . . ?
C6 C14 H14 120.9 . . ?
C6 C14 C16 118.1(4) . . ?
C16 C14 H14 120.9 . . ?
N1 C15 C8 113.6(3) . . ?
O2 C15 N1 123.2(3) . . ?
O2 C15 C8 123.2(3) . . ?
C8 C16 C14 121.3(4) . . ?
C8 C16 H16 119.3 . . ?
C14 C16 H16 119.3 . . ?
C9 C17 C13 121.7(3) . . ?
C9 C17 H17 119.1 . . ?
C13 C17 H17 119.1 . . ?
C5 C18 H18 120.5 . . ?
C6 C18 C5 119.0(4) . . ?
C6 C18 H18 120.5 . . ?
N12 C19 H19A 109.5 . . ?
N12 C19 H19B 109.5 . . ?
N12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N12 C20 H20A 109.5 . . ?
N12 C20 H20B 109.5 . . ?
N12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.744(4) . ?
N1 H1 0.8800 . ?
N1 N4 1.383(3) . ?
N1 C15 1.362(4) . ?
O2 C15 1.232(4) . ?
C3 H3 0.9500 . ?
C3 N4 1.285(4) . ?
C3 C13 1.449(4) . ?
C5 H5 0.9500 . ?
C5 C8 1.384(5) . ?
C5 C18 1.390(5) . ?
C6 C14 1.373(6) . ?
C6 C18 1.381(6) . ?
C7 H7 0.9500 . ?
C7 C10 1.403(5) . ?
C7 C11 1.377(5) . ?
C8 C15 1.490(5) . ?
C8 C16 1.384(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(5) . ?
C9 C17 1.380(5) . ?
C10 N12 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C13 1.399(5) . ?
N12 C19 1.456(5) . ?
N12 C20 1.445(5) . ?
C13 C17 1.389(5) . ?
C14 H14 0.9500 . ?
C14 C16 1.393(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C6 C14 C16 -179.4(3) . . . . ?
Cl1 C6 C18 C5 180.0(3) . . . . ?
C3 C13 C17 C9 -179.3(3) . . . . ?
N4 N1 C15 O2 -8.6(5) . . . . ?
N4 N1 C15 C8 173.4(3) . . . . ?
N4 C3 C13 C11 -15.8(5) . . . . ?
N4 C3 C13 C17 165.7(3) . . . . ?
C5 C8 C15 N1 140.2(3) . . . . ?
C5 C8 C15 O2 -37.8(5) . . . . ?
C5 C8 C16 C14 -1.2(5) . . . . ?
C6 C14 C16 C8 0.0(5) . . . . ?
C7 C10 N12 C19 174.7(3) . . . . ?
C7 C10 N12 C20 9.3(5) . . . . ?
C7 C11 C13 C3 179.8(3) . . . . ?
C7 C11 C13 C17 -1.8(5) . . . . ?
C8 C5 C18 C6 -1.2(6) . . . . ?
C9 C10 N12 C19 -6.1(5) . . . . ?
C9 C10 N12 C20 -171.5(4) . . . . ?
C10 C7 C11 C13 0.7(5) . . . . ?
C10 C9 C17 C13 -1.5(6) . . . . ?
C11 C7 C10 C9 0.0(5) . . . . ?
C11 C7 C10 N12 179.3(3) . . . . ?
C11 C13 C17 C9 2.2(5) . . . . ?
C13 C3 N4 N1 173.7(3) . . . . ?
C14 C6 C18 C5 0.0(6) . . . . ?
C15 N1 N4 C3 166.7(3) . . . . ?
C15 C8 C16 C14 177.3(3) . . . . ?
C16 C8 C15 N1 -38.3(4) . . . . ?
C16 C8 C15 O2 143.7(3) . . . . ?
C17 C9 C10 C7 0.4(5) . . . . ?
C17 C9 C10 N12 -178.8(3) . . . . ?
C18 C5 C8 C15 -176.7(3) . . . . ?
C18 C5 C8 C16 1.8(5) . . . . ?
C18 C6 C14 C16 0.6(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5340804
