#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:03:41 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299094 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160208.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_7160208
loop_
_publ_author_name
'He, Kun'
'Zeng, Weikun'
'Yu, Xianglin'
'Zhou, Jun'
'Jin, Yi'
_publ_section_title
;
 Direct synthesis of enone-hydrazones under solvent free and additive free
 conditions.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              377
_journal_page_last               382
_journal_paper_doi               10.1039/d4ob01578a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H22 N2 O'
_chemical_formula_sum            'C24 H22 N2 O'
_chemical_formula_weight         354.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.555(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.550(19)
_cell_length_b                   6.415(9)
_cell_length_c                   21.40(3)
_cell_measurement_reflns_used    602
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.89
_cell_measurement_theta_min      2.85
_cell_volume                     1964(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1497
_diffrn_reflns_av_unetI/netI     0.1862
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.862
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.2217
_refine_ls_R_factor_gt           0.0824
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.2388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1281
_reflns_number_total             3558
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01578a2.cif
_cod_data_source_block           hs
_cod_depositor_comments
'Adding full bibliography for 7160207--7160208.cif.'
_cod_database_code               7160208
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.099) H2(0.116) H3(0.12) H4(0.116) H5(0.099) H8(0.085)
 H9(0.089) H12(0.079) H13(0.092) H14(0.098) H15(0.094) H16(0.082) H18(0.085)
 H21(0.093) H22(0.083) H23A(0.163) H23B(0.163) H23C(0.163) H24A(0.145)
 H24B(0.145) H24C(0.145)
 Fixed X: H1(0.325949) H2(0.270416) H3(0.112509) H4(0.010048) H5(0.063167)
 H8(0.364449) H9(0.422017) H12(0.236005) H13(0.086306) H14(-0.028659)
 H15(0.004742) H16(0.153207) H18(0.285716) H21(0.506962) H22(0.439166)
 H23A(0.398334) H23B(0.313861) H23C(0.301664) H24A(0.530786) H24B(0.437295)
 H24C(0.513453)
 Fixed Y: H1(1.208115) H2(1.489413) H3(1.537809) H4(1.309826) H5(1.035367)
 H8(0.893183) H9(0.628082) H12(0.649167) H13(0.720954) H14(0.470461)
 H15(0.150887) H16(0.072852) H18(0.127131) H21(-0.239326) H22(0.047012) H23A(-
 0.192765) H23B(-0.316497) H23C(-0.081984) H24A(-0.476618) H24B(-0.529431)
 H24C(-0.392423)
 Fixed Z: H1(-0.147684) H2(-0.211414) H3(-0.24337) H4(-0.211583) H5(-0.144936)
 H8(-0.11942) H9(-0.056043) H12(0.092148) H13(0.108394) H14(0.086353)
 H15(0.048056) H16(0.03347) H18(0.161349) H21(0.080396) H22(0.026838)
 H23A(0.273363) H23B(0.23451) H23C(0.251912) H24A(0.163753) H24B(0.186906)
 H24C(0.229382)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1777(2) 0.8243(5) -0.06776(17) 0.0815(10) Uani 1 1 d . . . . .
N1 N 0.3115(3) 0.5573(6) -0.0209(2) 0.0707(12) Uani 1 1 d . . . . .
N2 N 0.3554(3) 0.3959(6) 0.0157(2) 0.0684(11) Uani 1 1 d . . . . .
C1 C 0.2618(4) 1.2278(8) -0.1599(3) 0.0821(16) Uani 1 1 d . . . . .
H1 H 0.325949 1.208115 -0.147684 0.099 Uiso 1 1 calc R U . . .
C2 C 0.2285(5) 1.3965(8) -0.1985(3) 0.0968(18) Uani 1 1 d . . . . .
H2 H 0.270416 1.489413 -0.211414 0.116 Uiso 1 1 calc R U . . .
C3 C 0.1347(6) 1.4257(9) -0.2174(3) 0.0998(19) Uani 1 1 d . . . . .
H3 H 0.112509 1.537809 -0.243370 0.120 Uiso 1 1 calc R U . . .
C4 C 0.0740(5) 1.2907(10) -0.1982(3) 0.0966(19) Uani 1 1 d . . . . .
H4 H 0.010048 1.309826 -0.211583 0.116 Uiso 1 1 calc R U . . .
C5 C 0.1059(4) 1.1242(8) -0.1587(3) 0.0827(16) Uani 1 1 d . . . . .
H5 H 0.063167 1.035367 -0.144936 0.099 Uiso 1 1 calc R U . . .
C6 C 0.2006(3) 1.0890(7) -0.1395(2) 0.0644(13) Uani 1 1 d . . . . .
C7 C 0.2334(3) 0.9046(7) -0.0987(2) 0.0636(13) Uani 1 1 d . . . . .
C8 C 0.3258(3) 0.8291(7) -0.0950(2) 0.0708(14) Uani 1 1 d . . . . .
H8 H 0.364449 0.893183 -0.119420 0.085 Uiso 1 1 calc R U . . .
C9 C 0.3601(4) 0.6663(8) -0.0570(3) 0.0744(14) Uani 1 1 d . . . . .
H9 H 0.422017 0.628082 -0.056043 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3075(3) 0.3003(7) 0.0525(2) 0.0616(13) Uani 1 1 d . . . . .
C11 C 0.2108(3) 0.3549(7) 0.0604(2) 0.0597(12) Uani 1 1 d . . . . .
C12 C 0.1897(3) 0.5480(7) 0.0833(2) 0.0657(13) Uani 1 1 d . . . . .
H12 H 0.236005 0.649167 0.092148 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1001(4) 0.5912(8) 0.0930(2) 0.0771(15) Uani 1 1 d . . . . .
H13 H 0.086306 0.720954 0.108394 0.092 Uiso 1 1 calc R U . . .
C14 C 0.0315(3) 0.4417(9) 0.0799(2) 0.0816(16) Uani 1 1 d . . . . .
H14 H -0.028659 0.470461 0.086353 0.098 Uiso 1 1 calc R U . . .
C15 C 0.0517(4) 0.2505(9) 0.0572(2) 0.0780(15) Uani 1 1 d . . . . .
H15 H 0.004742 0.150887 0.048056 0.094 Uiso 1 1 calc R U . . .
C16 C 0.1401(3) 0.2043(7) 0.0480(2) 0.0679(14) Uani 1 1 d . . . . .
H16 H 0.153207 0.072852 0.033470 0.082 Uiso 1 1 calc R U . . .
C17 C 0.3542(3) 0.1194(7) 0.0877(2) 0.0583(12) Uani 1 1 d . . . . .
C18 C 0.3312(3) 0.0538(7) 0.1451(3) 0.0710(14) Uani 1 1 d . . . . .
H18 H 0.285716 0.127131 0.161349 0.085 Uiso 1 1 calc R U . . .
C19 C 0.3735(4) -0.1173(8) 0.1790(2) 0.0722(14) Uani 1 1 d . . . . .
C20 C 0.4401(4) -0.2306(7) 0.1542(3) 0.0707(15) Uani 1 1 d . . . . .
C21 C 0.4625(3) -0.1649(8) 0.0973(3) 0.0772(15) Uani 1 1 d . . . . .
H21 H 0.506962 -0.239326 0.080396 0.093 Uiso 1 1 calc R U . . .
C22 C 0.4213(3) 0.0070(7) 0.0647(2) 0.0695(14) Uani 1 1 d . . . . .
H22 H 0.439166 0.047012 0.026838 0.083 Uiso 1 1 calc R U . . .
C23 C 0.3442(4) -0.1831(9) 0.2403(3) 0.109(2) Uani 1 1 d . . . . .
H23A H 0.398334 -0.192765 0.273363 0.163 Uiso 1 1 calc R U . . .
H23B H 0.313861 -0.316497 0.234510 0.163 Uiso 1 1 calc R U . . .
H23C H 0.301664 -0.081984 0.251912 0.163 Uiso 1 1 calc R U . . .
C24 C 0.4845(4) -0.4250(7) 0.1865(3) 0.0965(19) Uani 1 1 d . . . . .
H24A H 0.530786 -0.476618 0.163753 0.145 Uiso 1 1 calc R U . . .
H24B H 0.437295 -0.529431 0.186906 0.145 Uiso 1 1 calc R U . . .
H24C H 0.513453 -0.392423 0.229382 0.145 Uiso 1 1 calc R U . . .
H1D H 0.250(4) 0.589(8) -0.026(3) 0.11(2) Uiso 1 1 d . . . . .
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'
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
N2 N1 H1D 126(4) . . ?
C9 N1 N2 118.7(5) . . ?
C9 N1 H1D 115(4) . . ?
C10 N2 N1 117.0(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.8(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 122.5(4) . . ?
C5 C6 C1 117.7(5) . . ?
C5 C6 C7 119.7(5) . . ?
O1 C7 C6 117.9(4) . . ?
O1 C7 C8 122.1(5) . . ?
C8 C7 C6 120.0(5) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.4(5) . . ?
C9 C8 H8 118.8 . . ?
N1 C9 C8 124.9(5) . . ?
N1 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
N2 C10 C11 125.6(4) . . ?
N2 C10 C17 115.7(4) . . ?
C17 C10 C11 118.7(4) . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 C16 118.7(4) . . ?
C16 C11 C10 119.5(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.0(5) . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C10 121.6(5) . . ?
C22 C17 C10 121.1(5) . . ?
C22 C17 C18 117.3(4) . . ?
C17 C18 H18 118.6 . . ?
C17 C18 C19 122.8(5) . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C23 120.3(5) . . ?
C20 C19 C18 118.9(5) . . ?
C20 C19 C23 120.8(5) . . ?
C19 C20 C24 121.7(5) . . ?
C21 C20 C19 118.0(5) . . ?
C21 C20 C24 120.3(5) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 C20 122.6(5) . . ?
C22 C21 H21 118.7 . . ?
C17 C22 C21 120.4(5) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C7 1.248(5) . ?
N1 N2 1.382(5) . ?
N1 C9 1.337(6) . ?
N1 H1D 0.90(5) . ?
N2 C10 1.296(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(7) . ?
C1 C6 1.385(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.353(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(6) . ?
C6 C7 1.496(6) . ?
C7 C8 1.418(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.361(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.489(6) . ?
C10 C17 1.480(6) . ?
C11 C12 1.387(6) . ?
C11 C16 1.401(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(6) . ?
C17 C22 1.377(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(6) . ?
C19 C20 1.392(7) . ?
C19 C23 1.512(7) . ?
C20 C21 1.382(7) . ?
C20 C24 1.512(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
O1 C7 C8 C9 -0.8(7) . . . . ?
N1 N2 C10 C11 -2.5(7) . . . . ?
N1 N2 C10 C17 176.0(4) . . . . ?
N2 N1 C9 C8 -179.7(4) . . . . ?
N2 C10 C11 C12 -61.0(6) . . . . ?
N2 C10 C11 C16 122.7(5) . . . . ?
N2 C10 C17 C18 154.3(4) . . . . ?
N2 C10 C17 C22 -26.6(6) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C1 C6 C7 O1 159.6(5) . . . . ?
C1 C6 C7 C8 -19.1(7) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C1 C6 C7 179.3(5) . . . . ?
C2 C3 C4 C5 0.9(9) . . . . ?
C3 C4 C5 C6 -1.9(9) . . . . ?
C4 C5 C6 C1 1.5(8) . . . . ?
C4 C5 C6 C7 -178.0(5) . . . . ?
C5 C6 C7 O1 -21.0(7) . . . . ?
C5 C6 C7 C8 160.4(5) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?
C6 C7 C8 C9 177.8(4) . . . . ?
C7 C8 C9 N1 1.9(8) . . . . ?
C9 N1 N2 C10 176.7(4) . . . . ?
C10 C11 C12 C13 -176.9(4) . . . . ?
C10 C11 C16 C15 177.7(4) . . . . ?
C10 C17 C18 C19 179.5(4) . . . . ?
C10 C17 C22 C21 -178.3(4) . . . . ?
C11 C10 C17 C18 -27.1(6) . . . . ?
C11 C10 C17 C22 152.0(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C11 C16 C15 1.4(7) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C11 -1.4(7) . . . . ?
C16 C11 C12 C13 -0.7(7) . . . . ?
C17 C10 C11 C12 120.5(5) . . . . ?
C17 C10 C11 C16 -55.8(6) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C17 C18 C19 C23 -178.8(4) . . . . ?
C18 C17 C22 C21 0.8(6) . . . . ?
C18 C19 C20 C21 1.3(7) . . . . ?
C18 C19 C20 C24 -176.3(4) . . . . ?
C19 C20 C21 C22 -0.2(7) . . . . ?
C20 C21 C22 C17 -1.0(7) . . . . ?
C22 C17 C18 C19 0.3(7) . . . . ?
C23 C19 C20 C21 178.7(5) . . . . ?
C23 C19 C20 C24 1.0(7) . . . . ?
C24 C20 C21 C22 177.5(4) . . . . ?
