#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239933.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_2239933
loop_
_publ_author_name
'Kamaraj, A.'
'Rajkumar, R.'
'Krishnasamy, K.'
'Murugavel, S.'
_publ_section_title
;
 Crystal structure of methyl
 2-[2,4-bis(4-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]hydrazinecarboxylate
;
_journal_coeditor_code           SU2773
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              145
_journal_page_last               147
_journal_paper_doi               10.1107/S1600536814018935
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C22 H23 F2 N3 O2'
_chemical_formula_moiety         'C22 H23 F2 N3 O2'
_chemical_formula_sum            'C22 H23 F2 N3 O2'
_chemical_formula_weight         399.43
_chemical_name_systematic
2-[2,4-Bis(4-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]hydrazinecarboxylate
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.997(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.751(6)
_cell_length_b                   7.087(2)
_cell_length_c                   28.492(9)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      1.5
_cell_volume                     3886(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia (2012)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and  PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18613
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0495
_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)+(0.0752P)²+2.7221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                2872
_reflns_number_total             3793
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2773sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2239933
_cod_database_fobs_code          2239933
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.34340(10) 0.7153(3) 0.09187(6) 0.0395(4) Uani d . 1 1
H H1 0.2935 0.7216 0.0775 0.047 Uiso calc R 1 1
C C2 0.37276(10) 0.9185(3) 0.09443(6) 0.0397(4) Uani d . 1 1
H H2 0.3614 0.9740 0.0621 0.048 Uiso calc R 1 1
C C3 0.33596(9) 1.0266(3) 0.12629(6) 0.0375(4) Uani d . 1 1
C C4 0.35286(10) 0.9504(3) 0.17646(6) 0.0418(4) Uani d . 1 1
H H4 0.3280 1.0258 0.1960 0.050 Uiso calc R 1 1
C C5 0.32457(10) 0.7461(3) 0.17394(6) 0.0411(4) Uani d . 1 1
H H5 0.2740 0.7514 0.1625 0.049 Uiso calc R 1 1
C C6 0.45136(10) 0.9334(3) 0.11470(7) 0.0488(5) Uani d . 1 1
H H6A 0.4747 0.8521 0.0960 0.059 Uiso calc R 1 1
H H6B 0.4658 1.0619 0.1105 0.059 Uiso calc R 1 1
C C7 0.47506(11) 0.8806(4) 0.16730(8) 0.0568(6) Uani d . 1 1
H H7A 0.4737 0.7445 0.1704 0.068 Uiso calc R 1 1
H H7B 0.5228 0.9211 0.1790 0.068 Uiso calc R 1 1
C C8 0.43043(11) 0.9689(3) 0.19781(7) 0.0506(5) Uani d . 1 1
H H8A 0.4421 1.1016 0.2021 0.061 Uiso calc R 1 1
H H8B 0.4411 0.9100 0.2294 0.061 Uiso calc R 1 1
C C9 0.37645(10) 0.5907(3) 0.06043(7) 0.0415(4) Uani d . 1 1
C C10 0.35221(11) 0.5986(3) 0.01104(7) 0.0500(5) Uani d . 1 1
H H10 0.3158 0.6797 -0.0020 0.060 Uiso calc R 1 1
C C11 0.38109(13) 0.4882(4) -0.01910(8) 0.0609(6) Uani d . 1 1
H H11 0.3648 0.4941 -0.0523 0.073 Uiso calc R 1 1
C C12 0.43378(14) 0.3710(3) 0.00080(9) 0.0622(7) Uani d . 1 1
C C13 0.45997(13) 0.3609(3) 0.04883(9) 0.0631(6) Uani d . 1 1
H H13 0.4969 0.2808 0.0614 0.076 Uiso calc R 1 1
C C14 0.43080(12) 0.4716(3) 0.07882(8) 0.0530(5) Uani d . 1 1
H H14 0.4482 0.4656 0.1119 0.064 Uiso calc R 1 1
C C15 0.34057(10) 0.6549(3) 0.22311(6) 0.0435(5) Uani d . 1 1
C C16 0.38849(13) 0.5154(3) 0.23568(8) 0.0603(6) Uani d . 1 1
H H16 0.4112 0.4693 0.2128 0.072 Uiso calc R 1 1
C C17 0.40412(15) 0.4407(4) 0.28160(9) 0.0718(7) Uani d . 1 1
H H17 0.4368 0.3449 0.2897 0.086 Uiso calc R 1 1
C C18 0.37098(14) 0.5097(4) 0.31434(8) 0.0628(6) Uani d . 1 1
C C19 0.32234(13) 0.6474(4) 0.30379(7) 0.0618(6) Uani d . 1 1
H H19 0.3001 0.6920 0.3271 0.074 Uiso calc R 1 1
C C20 0.30660(12) 0.7197(3) 0.25771(7) 0.0530(5) Uani d . 1 1
H H20 0.2728 0.8129 0.2497 0.064 Uiso calc R 1 1
C C21 0.22233(9) 1.3588(3) 0.05966(6) 0.0383(4) Uani d . 1 1
C C22 0.14426(13) 1.5496(4) 0.08890(9) 0.0650(6) Uani d . 1 1
H H22A 0.1636 1.6721 0.0859 0.098 Uiso calc R 1 1
H H22B 0.1214 1.5500 0.1153 0.098 Uiso calc R 1 1
H H22C 0.1113 1.5189 0.0597 0.098 Uiso calc R 1 1
N N1 0.35236(8) 0.6352(2) 0.13996(5) 0.0416(4) Uani d . 1 1
H H1A 0.3728 0.5289 0.1477 0.050 Uiso calc R 1 1
N N2 0.29174(8) 1.1591(2) 0.11708(5) 0.0384(4) Uani d . 1 1
N N3 0.27210(8) 1.2269(2) 0.07053(5) 0.0396(4) Uani d . 1 1
H H3 0.2917 1.1846 0.0486 0.048 Uiso calc R 1 1
O O2 0.19861(7) 1.4123(2) 0.09762(5) 0.0516(4) Uani d . 1 1
O O3 0.20192(7) 1.4228(2) 0.01966(5) 0.0487(4) Uani d . 1 1
F F1 0.46171(10) 0.2594(2) -0.02847(6) 0.0940(6) Uani d . 1 1
F F2 0.38685(10) 0.4378(3) 0.35949(5) 0.0986(6) Uani d . 1 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
N1 C1 C9 110.73(15)
N1 C1 C2 110.67(15)
C9 C1 C2 111.42(15)
N1 C1 H1 108.0
C9 C1 H1 108.0
C2 C1 H1 108.0
C3 C2 C6 108.99(16)
C3 C2 C1 106.09(14)
C6 C2 C1 114.73(16)
C3 C2 H2 109.0
C6 C2 H2 109.0
C1 C2 H2 109.0
N2 C3 C4 117.43(16)
N2 C3 C2 131.26(16)
C4 C3 C2 111.18(15)
C3 C4 C8 109.85(16)
C3 C4 C5 107.04(15)
C8 C4 C5 114.81(16)
C3 C4 H4 108.3
C8 C4 H4 108.3
C5 C4 H4 108.3
N1 C5 C15 110.89(16)
N1 C5 C4 110.59(15)
C15 C5 C4 111.04(15)
N1 C5 H5 108.1
C15 C5 H5 108.1
C4 C5 H5 108.1
C7 C6 C2 114.68(16)
C7 C6 H6A 108.6
C2 C6 H6A 108.6
C7 C6 H6B 108.6
C2 C6 H6B 108.6
H6A C6 H6B 107.6
C8 C7 C6 112.23(18)
C8 C7 H7A 109.2
C6 C7 H7A 109.2
C8 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
C7 C8 C4 113.64(17)
C7 C8 H8A 108.8
C4 C8 H8A 108.8
C7 C8 H8B 108.8
C4 C8 H8B 108.8
H8A C8 H8B 107.7
C14 C9 C10 118.38(19)
C14 C9 C1 122.62(17)
C10 C9 C1 118.98(18)
C11 C10 C9 121.0(2)
C11 C10 H10 119.5
C9 C10 H10 119.5
C12 C11 C10 118.4(2)
C12 C11 H11 120.8
C10 C11 H11 120.8
C13 C12 C11 122.7(2)
C13 C12 F1 118.4(2)
C11 C12 F1 118.8(2)
C12 C13 C14 118.6(2)
C12 C13 H13 120.7
C14 C13 H13 120.7
C9 C14 C13 120.9(2)
C9 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C20 118.16(18)
C16 C15 C5 122.92(17)
C20 C15 C5 118.90(19)
C15 C16 C17 121.5(2)
C15 C16 H16 119.2
C17 C16 H16 119.2
C18 C17 C16 118.5(2)
C18 C17 H17 120.7
C16 C17 H17 120.7
C17 C18 F2 118.5(3)
C17 C18 C19 122.6(2)
F2 C18 C19 118.9(2)
C18 C19 C20 118.4(2)
C18 C19 H19 120.8
C20 C19 H19 120.8
C19 C20 C15 120.8(2)
C19 C20 H20 119.6
C15 C20 H20 119.6
O3 C21 O2 123.87(17)
O3 C21 N3 123.44(17)
O2 C21 N3 112.68(15)
O2 C22 H22A 109.5
O2 C22 H22B 109.5
H22A C22 H22B 109.5
O2 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C5 N1 C1 115.71(15)
C5 N1 H1A 122.1
C1 N1 H1A 122.1
C3 N2 N3 119.17(15)
C21 N3 N2 119.81(14)
C21 N3 H3 120.1
N2 N3 H3 120.1
C21 O2 C22 116.23(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.457(2)
C1 C9 1.507(3)
C1 C2 1.548(3)
C1 H1 0.9800
C2 C3 1.495(2)
C2 C6 1.533(3)
C2 H2 0.9800
C3 N2 1.269(2)
C3 C4 1.494(2)
C4 C8 1.522(3)
C4 C5 1.548(3)
C4 H4 0.9800
C5 N1 1.447(2)
C5 C15 1.510(3)
C5 H5 0.9800
C6 C7 1.513(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.506(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C9 C14 1.373(3)
C9 C10 1.382(3)
C10 C11 1.376(3)
C10 H10 0.9300
C11 C12 1.352(4)
C11 H11 0.9300
C12 C13 1.352(3)
C12 F1 1.354(2)
C13 C14 1.378(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.360(3)
C15 C20 1.389(3)
C16 C17 1.381(3)
C16 H16 0.9300
C17 C18 1.346(4)
C17 H17 0.9300
C18 F2 1.353(2)
C18 C19 1.355(4)
C19 C20 1.378(3)
C19 H19 0.9300
C20 H20 0.9300
C21 O3 1.208(2)
C21 O2 1.327(2)
C21 N3 1.342(2)
C22 O2 1.428(3)
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
N1 H1A 0.8600
N2 N3 1.3814(19)
N3 H3 0.8600
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
N3 H3 O3 7_575 0.86 2.12 2.930(2) 157
C2 H2 O3 7_575 0.98 2.49 3.442(2) 163
C22 H22C F1 7_565 0.96 2.49 3.243(3) 136
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
N1 C1 C2 C3 -56.46(19)
C9 C1 C2 C3 179.87(15)
N1 C1 C2 C6 63.9(2)
C9 C1 C2 C6 -59.8(2)
C6 C2 C3 N2 124.6(2)
C1 C2 C3 N2 -111.4(2)
C6 C2 C3 C4 -59.9(2)
C1 C2 C3 C4 64.16(19)
N2 C3 C4 C8 -122.34(19)
C2 C3 C4 C8 61.4(2)
N2 C3 C4 C5 112.41(19)
C2 C3 C4 C5 -63.81(19)
C3 C4 C5 N1 55.25(19)
C8 C4 C5 N1 -67.0(2)
C3 C4 C5 C15 178.80(15)
C8 C4 C5 C15 56.6(2)
C3 C2 C6 C7 52.2(2)
C1 C2 C6 C7 -66.5(2)
C2 C6 C7 C8 -45.8(3)
C6 C7 C8 C4 46.3(3)
C3 C4 C8 C7 -54.2(2)
C5 C4 C8 C7 66.5(2)
N1 C1 C9 C14 -26.0(3)
C2 C1 C9 C14 97.7(2)
N1 C1 C9 C10 155.29(17)
C2 C1 C9 C10 -81.1(2)
C14 C9 C10 C11 0.8(3)
C1 C9 C10 C11 179.62(18)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C13 -1.4(3)
C10 C11 C12 F1 178.83(19)
C11 C12 C13 C14 1.4(4)
F1 C12 C13 C14 -178.8(2)
C10 C9 C14 C13 -0.8(3)
C1 C9 C14 C13 -179.51(19)
C12 C13 C14 C9 -0.3(3)
N1 C5 C15 C16 14.8(3)
C4 C5 C15 C16 -108.6(2)
N1 C5 C15 C20 -167.30(17)
C4 C5 C15 C20 69.3(2)
C20 C15 C16 C17 -0.9(4)
C5 C15 C16 C17 177.1(2)
C15 C16 C17 C18 -0.3(4)
C16 C17 C18 F2 -179.3(2)
C16 C17 C18 C19 0.9(4)
C17 C18 C19 C20 -0.3(4)
F2 C18 C19 C20 180.0(2)
C18 C19 C20 C15 -1.0(4)
C16 C15 C20 C19 1.5(3)
C5 C15 C20 C19 -176.5(2)
C15 C5 N1 C1 -176.69(15)
C4 C5 N1 C1 -53.1(2)
C9 C1 N1 C5 178.09(15)
C2 C1 N1 C5 54.0(2)
C4 C3 N2 N3 -176.76(16)
C2 C3 N2 N3 -1.5(3)
O3 C21 N3 N2 -179.05(17)
O2 C21 N3 N2 1.6(2)
C3 N2 N3 C21 175.91(17)
O3 C21 O2 C22 2.0(3)
N3 C21 O2 C22 -178.61(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086908
