#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/04/8000458.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_8000458
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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   11.3576(10)
_cell_length_b                   8.0121(6)
_cell_length_c                   67.179(6)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.671
_cell_measurement_theta_min      3.033
_cell_volume                     6113.2(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_limit_l_min       -79
_diffrn_reflns_number            84796
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+23.8717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                4943
_reflns_number_total             5390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jz0c02623_si_002.cif
_cod_data_source_block           Cry-B
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H16 Cl N3 O)'
_cod_original_formula_sum        'C32 H32 Cl2 N6 O2'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     603.54
_cod_database_code               8000458
_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:
 N2(H2), N8(H8), C10(H10), C11(H11), C14(H14), C16(H16), C19(H19), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C34(H34),
  C35(H35), C36(H36), C37(H37), C39(H39)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C)
;
_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+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.70560(12) 0.19152(16) 0.073798(16) 0.0468(3) Uani 1 d . . .
Cl2 Cl 0.06055(12) -0.2075(2) 0.167201(18) 0.0572(4) Uani 1 d . . .
O1 O 0.6229(2) -0.1772(4) 0.16215(4) 0.0298(7) Uani 1 d . . .
N2 N 0.7710(3) 0.0009(4) 0.17068(4) 0.0269(8) Uani 1 d . . .
H2 H 0.8190 0.0804 0.1667 0.032 Uiso 1 calc . . R
N3 N 0.7743(3) -0.0541(4) 0.19031(4) 0.0247(7) Uani 1 d . . .
N4 N 0.2586(3) 0.2369(4) 0.06492(4) 0.0268(7) Uani 1 d . . .
O5 O 0.1344(3) 0.3690(4) 0.09566(4) 0.0322(7) Uani 1 d . . .
C6 C 0.3896(4) 0.3525(5) -0.00588(5) 0.0242(8) Uani 1 d . . .
N7 N 0.4014(3) 0.4082(4) -0.02508(5) 0.0293(8) Uani 1 d . . .
N8 N 0.2381(3) 0.1512(4) 0.08256(4) 0.0267(8) Uani 1 d . . .
H8 H 0.2691 0.0519 0.0845 0.032 Uiso 1 calc . . R
C9 C 0.3593(3) 0.2395(5) 0.03387(5) 0.0214(8) Uani 1 d . . .
C10 C 0.2840(4) 0.3576(5) 0.02547(6) 0.0246(9) Uani 1 d . . .
H10 H 0.2211 0.4003 0.0333 0.030 Uiso 1 calc . . R
C11 C 0.3392(3) 0.1741(5) 0.05386(5) 0.0237(8) Uani 1 d . . .
H11 H 0.3861 0.0846 0.0587 0.028 Uiso 1 calc . . R
C12 C 0.7050(4) 0.1136(5) 0.09814(6) 0.0314(10) Uani 1 d . . .
C13 C 0.4900(4) 0.3369(6) -0.03809(6) 0.0344(10) Uani 1 d . . .
H13A H 0.5680 0.3515 -0.0321 0.052 Uiso 1 calc . . GR
H13B H 0.4876 0.3934 -0.0510 0.052 Uiso 1 calc . . GR
H13C H 0.4742 0.2177 -0.0399 0.052 Uiso 1 calc . . GR
C14 C 0.4659(3) 0.2329(5) 0.00237(5) 0.0227(8) Uani 1 d . . .
H14 H 0.5283 0.1886 -0.0054 0.027 Uiso 1 calc . . R
C15 C 0.6942(3) -0.0678(5) 0.15772(6) 0.0248(9) Uani 1 d . . .
C16 C 0.8504(3) 0.0227(5) 0.20103(6) 0.0246(9) Uani 1 d . . .
H16 H 0.8998 0.1036 0.1949 0.030 Uiso 1 calc . . R
C17 C 0.1697(4) 0.2225(5) 0.09670(6) 0.0291(9) Uani 1 d . . .
C18 C 0.8841(4) -0.0490(5) 0.26398(6) 0.0266(9) Uani 1 d . . .
C19 C 0.2976(4) 0.4143(5) 0.00633(6) 0.0257(9) Uani 1 d . . .
H19 H 0.2448 0.4957 0.0012 0.031 Uiso 1 calc . . R
C20 C 0.7858(4) -0.1126(5) 0.23286(6) 0.0262(9) Uani 1 d . . .
H20 H 0.7255 -0.1700 0.2259 0.031 Uiso 1 calc . . R
C21 C 0.8633(3) -0.0104(5) 0.22235(5) 0.0228(8) Uani 1 d . . .
C22 C 0.3217(4) 0.5331(6) -0.03291(6) 0.0337(10) Uani 1 d . . .
H22A H 0.2408 0.4909 -0.0324 0.051 Uiso 1 calc . . GR
H22B H 0.3426 0.5580 -0.0467 0.051 Uiso 1 calc . . GR
H22C H 0.3278 0.6351 -0.0249 0.051 Uiso 1 calc . . GR
C23 C 0.1122(4) -0.0533(5) 0.11146(6) 0.0304(9) Uani 1 d . . .
H23 H 0.1094 -0.0999 0.0985 0.036 Uiso 1 calc . . R
C24 C 0.4506(3) 0.1789(5) 0.02193(5) 0.0234(8) Uani 1 d . . .
H24 H 0.5035 0.0988 0.0273 0.028 Uiso 1 calc . . R
N25 N 0.8927(3) -0.0663(5) 0.28436(5) 0.0359(9) Uani 1 d . . .
C26 C 0.9634(3) 0.0510(5) 0.25334(6) 0.0275(9) Uani 1 d . . .
H26 H 1.0253 0.1063 0.2602 0.033 Uiso 1 calc . . R
C27 C 0.8068(4) 0.1194(6) 0.10919(6) 0.0337(10) Uani 1 d . . .
H27 H 0.8774 0.1622 0.1036 0.040 Uiso 1 calc . . R
C28 C 0.7949(4) -0.1320(5) 0.25318(6) 0.0290(9) Uani 1 d . . .
H28 H 0.7406 -0.2020 0.2600 0.035 Uiso 1 calc . . R
C29 C 0.7018(4) -0.0002(5) 0.13682(6) 0.0247(8) Uani 1 d . . .
C30 C 0.0869(4) -0.1522(6) 0.12799(7) 0.0372(11) Uani 1 d . . .
H30 H 0.0669 -0.2665 0.1264 0.045 Uiso 1 calc . . R
C31 C 0.1421(4) 0.1825(6) 0.13304(6) 0.0334(10) Uani 1 d . . .
H31 H 0.1591 0.2977 0.1347 0.040 Uiso 1 calc . . R
C32 C 0.1416(3) 0.1141(5) 0.11403(6) 0.0269(9) Uani 1 d . . .
C33 C 0.9866(4) 0.0171(7) 0.29510(6) 0.0445(12) Uani 1 d . . .
H33A H 1.0628 -0.0174 0.2896 0.067 Uiso 1 calc . . GR
H33B H 0.9825 -0.0131 0.3092 0.067 Uiso 1 calc . . GR
H33C H 0.9778 0.1382 0.2937 0.067 Uiso 1 calc . . GR
C34 C 0.8046(4) 0.0619(6) 0.12868(6) 0.0309(10) Uani 1 d . . .
H34 H 0.8743 0.0652 0.1365 0.037 Uiso 1 calc . . R
C35 C 0.6026(4) 0.0492(6) 0.10567(6) 0.0345(10) Uani 1 d . . .
H35 H 0.5333 0.0457 0.0978 0.041 Uiso 1 calc . . R
C36 C 0.9521(3) 0.0697(5) 0.23293(6) 0.0266(9) Uani 1 d . . .
H36 H 1.0062 0.1390 0.2260 0.032 Uiso 1 calc . . R
C37 C 0.6015(4) -0.0108(6) 0.12504(6) 0.0329(10) Uani 1 d . . .
H37 H 0.5318 -0.0594 0.1303 0.039 Uiso 1 calc . . R
C38 C 0.0915(4) -0.0811(7) 0.14680(7) 0.0386(11) Uani 1 d . . .
C39 C 0.1179(4) 0.0844(7) 0.14959(6) 0.0374(11) Uani 1 d . . .
H39 H 0.1197 0.1310 0.1626 0.045 Uiso 1 calc . . R
C40 C 0.7998(4) -0.1455(7) 0.29565(6) 0.0443(12) Uani 1 d . . .
H40A H 0.7249 -0.0896 0.2929 0.066 Uiso 1 calc . . GR
H40B H 0.8175 -0.1373 0.3099 0.066 Uiso 1 calc . . GR
H40C H 0.7942 -0.2633 0.2918 0.066 Uiso 1 calc . . GR
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
C15 N2 N3 120.0(3) . . ?
C16 N3 N2 113.5(3) . . ?
C11 N4 N8 114.8(3) . . ?
N7 C6 C14 122.2(4) . . ?
N7 C6 C19 120.1(4) . . ?
C14 C6 C19 117.7(3) . . ?
C6 N7 C13 120.4(3) . . ?
C6 N7 C22 120.4(3) . . ?
C22 N7 C13 119.2(3) . . ?
C17 N8 N4 119.1(3) . . ?
C10 C9 C11 121.3(4) . . ?
C10 C9 C24 117.3(3) . . ?
C24 C9 C11 121.2(3) . . ?
C19 C10 C9 122.3(4) . . ?
N4 C11 C9 120.2(4) . . ?
C27 C12 Cl1 119.3(3) . . ?
C35 C12 Cl1 118.9(3) . . ?
C35 C12 C27 121.8(4) . . ?
C24 C14 C6 120.4(4) . . ?
O1 C15 N2 124.1(4) . . ?
O1 C15 C29 121.3(4) . . ?
N2 C15 C29 114.6(3) . . ?
N3 C16 C21 122.0(4) . . ?
O5 C17 N8 123.0(4) . . ?
O5 C17 C32 121.8(4) . . ?
N8 C17 C32 115.2(4) . . ?
N25 C18 C26 121.2(4) . . ?
N25 C18 C28 120.9(4) . . ?
C26 C18 C28 117.9(3) . . ?
C10 C19 C6 120.6(4) . . ?
C28 C20 C21 121.4(4) . . ?
C20 C21 C16 122.6(4) . . ?
C36 C21 C16 119.3(4) . . ?
C36 C21 C20 118.0(3) . . ?
C32 C23 C30 119.9(4) . . ?
C14 C24 C9 121.7(4) . . ?
C18 N25 C33 120.0(4) . . ?
C18 N25 C40 120.8(4) . . ?
C40 N25 C33 118.5(3) . . ?
C36 C26 C18 120.5(4) . . ?
C12 C27 C34 118.9(4) . . ?
C20 C28 C18 120.6(4) . . ?
C34 C29 C15 123.1(3) . . ?
C34 C29 C37 119.3(4) . . ?
C37 C29 C15 117.5(4) . . ?
C38 C30 C23 119.0(4) . . ?
C32 C31 C39 120.8(4) . . ?
C23 C32 C17 121.1(4) . . ?
C31 C32 C17 119.2(4) . . ?
C31 C32 C23 119.6(4) . . ?
C29 C34 C27 120.5(4) . . ?
C12 C35 C37 119.0(4) . . ?
C26 C36 C21 121.5(4) . . ?
C35 C37 C29 120.4(4) . . ?
C30 C38 Cl2 118.1(4) . . ?
C39 C38 Cl2 119.9(4) . . ?
C39 C38 C30 122.0(4) . . ?
C38 C39 C31 118.7(4) . . ?
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 C12 1.751(4) . ?
Cl2 C38 1.740(4) . ?
O1 C15 1.230(5) . ?
N2 N3 1.391(4) . ?
N2 C15 1.350(5) . ?
N3 C16 1.282(5) . ?
N4 N8 1.390(4) . ?
N4 C11 1.282(5) . ?
O5 C17 1.242(5) . ?
C6 N7 1.372(5) . ?
C6 C14 1.406(6) . ?
C6 C19 1.418(5) . ?
N7 C13 1.449(5) . ?
N7 C22 1.448(5) . ?
N8 C17 1.353(5) . ?
C9 C10 1.394(5) . ?
C9 C11 1.460(5) . ?
C9 C24 1.398(5) . ?
C10 C19 1.373(5) . ?
C12 C27 1.374(6) . ?
C12 C35 1.369(6) . ?
C14 C24 1.394(5) . ?
C15 C29 1.507(5) . ?
C16 C21 1.464(5) . ?
C17 C32 1.487(5) . ?
C18 N25 1.380(5) . ?
C18 C26 1.401(6) . ?
C18 C28 1.412(6) . ?
C20 C21 1.394(6) . ?
C20 C28 1.378(5) . ?
C21 C36 1.391(5) . ?
C23 C30 1.394(6) . ?
C23 C32 1.392(6) . ?
N25 C33 1.450(6) . ?
N25 C40 1.446(6) . ?
C26 C36 1.385(5) . ?
C27 C34 1.388(6) . ?
C29 C34 1.382(6) . ?
C29 C37 1.389(6) . ?
C30 C38 1.387(7) . ?
C31 C32 1.390(6) . ?
C31 C39 1.389(6) . ?
C35 C37 1.388(6) . ?
C38 C39 1.373(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168344073
