#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226679.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_2226679
loop_
_publ_author_name
'Cang, Hui'
'Bian, Jin-Fa'
'Wang, Si-Qing'
'Wang, Jin-Tang'
_publ_section_title
;
 N-(4,5-Diaza-9H-fluoren-9-ylidene)-4-methoxyaniline
;
_journal_coeditor_code           SJ5020
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1804
_journal_paper_doi               10.1107/S1600536810023275
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H13 N3 O'
_chemical_formula_moiety         'C18 H13 N3 O'
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31
_chemical_name_systematic
;
N-(4,5-Diaza-9H-fluoren-9-ylidene)-4-methoxyaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3070(17)
_cell_length_b                   12.839(3)
_cell_length_c                   13.233(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1400.5(5)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2678
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0806
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.2118
_reflns_number_gt                1599
_reflns_number_total             2498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5020.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226679
_cod_database_fobs_code          2226679
loop_
_symmetry_equiv_pos_as_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_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_disorder_assembly
_atom_site_disorder_group
O O 0.1797(4) 0.1191(2) 0.5460(2) 0.0455(8) Uani d . 1 . .
N N1 -0.4360(4) 0.2396(3) 0.3622(3) 0.045 Uani d . 1 . .
C C1 0.2903(6) 0.0674(4) 0.4883(4) 0.0580(14) Uani d . 1 . .
H H1B 0.3927 0.0584 0.5298 0.087 Uiso calc R 1 . .
H H1C 0.3054 0.1085 0.4296 0.087 Uiso calc R 1 . .
H H1D 0.2473 0.0005 0.4668 0.087 Uiso calc R 1 . .
N N2 -0.4715(5) 0.6162(3) 0.3850(3) 0.0417(9) Uani d U 1 . .
C C2 0.0291(5) 0.1441(3) 0.4969(3) 0.0354(10) Uani d . 1 . .
C C3 -0.0260(5) 0.1213(3) 0.3959(3) 0.0426(11) Uani d . 1 . .
H H3A 0.0405 0.0853 0.3563 0.051 Uiso calc R 1 . .
N N3 -0.7987(5) 0.5270(3) 0.2939(3) 0.0498(11) Uani d . 1 . .
C C4 -0.1786(5) 0.1517(4) 0.3544(3) 0.0425(11) Uani d . 1 . .
H H4A -0.2162 0.1317 0.2881 0.051 Uiso calc R 1 . .
C C5 -0.2786(5) 0.2115(3) 0.4081(3) 0.0337(10) Uani d . 1 . .
C C6 -0.2233(6) 0.2327(4) 0.5093(3) 0.0448(12) Uani d . 1 . .
H H6A -0.2908 0.2678 0.5489 0.054 Uiso calc R 1 . .
C C7 -0.0708(5) 0.2028(3) 0.5526(3) 0.0392(10) Uani d . 1 . .
H H7A -0.0342 0.2218 0.6193 0.047 Uiso calc R 1 . .
C C8 -0.4781(5) 0.3355(3) 0.3556(3) 0.0325(9) Uani d . 1 . .
C C9 -0.3939(5) 0.4347(3) 0.3850(3) 0.0353(10) Uani d U 1 . .
C C10 -0.2335(5) 0.4605(4) 0.4154(3) 0.0429(11) Uani d U 1 . .
H H10A -0.1533 0.4096 0.4233 0.051 Uiso calc R 1 . .
C C11 -0.1965(6) 0.5636(4) 0.4337(4) 0.0490(12) Uani d U 1 . .
H H11A -0.0902 0.5835 0.4554 0.059 Uiso calc R 1 . .
C C12 -0.3178(6) 0.6378(4) 0.4197(3) 0.0433(11) Uani d U 1 . .
H H12A -0.2906 0.7066 0.4355 0.052 Uiso calc R 1 . .
C C13 -0.5040(5) 0.5164(3) 0.3679(3) 0.0346(10) Uani d U 1 . .
C C14 -0.6635(5) 0.4748(4) 0.3245(3) 0.0363(10) Uani d . 1 . .
C C15 -0.9247(6) 0.4701(5) 0.2532(4) 0.0583(15) Uani d . 1 . .
H H15A -1.0208 0.5047 0.2307 0.070 Uiso calc R 1 . .
C C16 -0.9214(6) 0.3612(5) 0.2422(4) 0.0564(14) Uani d . 1 . .
H H16A -1.0131 0.3252 0.2137 0.068 Uiso calc R 1 . .
C C17 -0.7832(5) 0.3104(4) 0.2738(3) 0.0467(12) Uani d . 1 . .
H H17A -0.7777 0.2384 0.2674 0.056 Uiso calc R 1 . .
C C18 -0.6499(5) 0.3656(4) 0.3156(3) 0.0365(10) Uani d . 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'
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
C2 O C1 . . 117.6(4) ?
C8 N1 C5 . . 120.2(4) ?
O C1 H1B . . 109.5 ?
O C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C13 N2 C12 . . 115.3(4) ?
O C2 C3 . . 125.3(4) ?
O C2 C7 . . 116.2(4) ?
C3 C2 C7 . . 118.4(4) ?
C4 C3 C2 . . 120.1(4) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C14 N3 C15 . . 116.0(5) ?
C3 C4 C5 . . 122.2(4) ?
C3 C4 H4A . . 118.9 ?
C5 C4 H4A . . 118.9 ?
C6 C5 C4 . . 117.1(4) ?
C6 C5 N1 . . 122.7(4) ?
C4 C5 N1 . . 120.0(4) ?
C7 C6 C5 . . 121.6(4) ?
C7 C6 H6A . . 119.2 ?
C5 C6 H6A . . 119.2 ?
C6 C7 C2 . . 120.4(4) ?
C6 C7 H7A . . 119.8 ?
C2 C7 H7A . . 119.8 ?
N1 C8 C9 . . 133.8(4) ?
N1 C8 C18 . . 120.6(4) ?
C9 C8 C18 . . 105.5(3) ?
C10 C9 C13 . . 117.2(4) ?
C10 C9 C8 . . 133.5(4) ?
C13 C9 C8 . . 109.0(4) ?
C11 C10 C9 . . 117.9(4) ?
C11 C10 H10A . . 121.1 ?
C9 C10 H10A . . 121.1 ?
C10 C11 C12 . . 119.8(4) ?
C10 C11 H11A . . 120.1 ?
C12 C11 H11A . . 120.1 ?
N2 C12 C11 . . 123.7(4) ?
N2 C12 H12A . . 118.1 ?
C11 C12 H12A . . 118.1 ?
N2 C13 C9 . . 125.8(4) ?
N2 C13 C14 . . 124.9(4) ?
C9 C13 C14 . . 109.3(4) ?
N3 C14 C18 . . 123.3(4) ?
N3 C14 C13 . . 128.3(4) ?
C18 C14 C13 . . 108.4(4) ?
N3 C15 C16 . . 124.2(5) ?
N3 C15 H15A . . 117.9 ?
C16 C15 H15A . . 117.9 ?
C17 C16 C15 . . 118.5(5) ?
C17 C16 H16A . . 120.7 ?
C15 C16 H16A . . 120.7 ?
C16 C17 C18 . . 119.4(5) ?
C16 C17 H17A . . 120.3 ?
C18 C17 H17A . . 120.3 ?
C17 C18 C14 . . 118.5(4) ?
C17 C18 C8 . . 133.6(4) ?
C14 C18 C8 . . 107.8(4) ?
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
O C2 . 1.375(5) ?
O C1 . 1.429(5) ?
N1 C8 . 1.280(5) ?
N1 C5 . 1.418(5) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
N2 C13 . 1.323(5) ?
N2 C12 . 1.331(6) ?
C2 C3 . 1.389(6) ?
C2 C7 . 1.397(6) ?
C3 C4 . 1.374(6) ?
C3 H3A . 0.9300 ?
N3 C14 . 1.328(5) ?
N3 C15 . 1.333(6) ?
C4 C5 . 1.389(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.388(6) ?
C6 C7 . 1.378(6) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 C9 . 1.482(6) ?
C8 C18 . 1.510(6) ?
C9 C10 . 1.383(6) ?
C9 C13 . 1.392(6) ?
C10 C11 . 1.375(7) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.382(6) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 C14 . 1.477(6) ?
C14 C18 . 1.412(6) ?
C15 C16 . 1.407(8) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.341(7) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.372(6) ?
C17 H17A . 0.9300 ?
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
_geom_hbond_publ_flag
C12 H12A O 3_566 0.9300 2.4200 3.337(6) 169.00 yes
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
C1 O C2 C3 . . . . 1.4(6) ?
C1 O C2 C7 . . . . -174.4(4) ?
O C2 C3 C4 . . . . -179.0(4) ?
C7 C2 C3 C4 . . . . -3.2(6) ?
C2 C3 C4 C5 . . . . 4.4(7) ?
C3 C4 C5 C6 . . . . -5.1(7) ?
C3 C4 C5 N1 . . . . -179.1(4) ?
C8 N1 C5 C6 . . . . 62.1(6) ?
C8 N1 C5 C4 . . . . -124.2(5) ?
C4 C5 C6 C7 . . . . 4.9(6) ?
N1 C5 C6 C7 . . . . 178.8(4) ?
C5 C6 C7 C2 . . . . -4.1(7) ?
O C2 C7 C6 . . . . 179.2(4) ?
C3 C2 C7 C6 . . . . 3.1(6) ?
C5 N1 C8 C9 . . . . 1.7(7) ?
C5 N1 C8 C18 . . . . -174.5(3) ?
N1 C8 C9 C10 . . . . 11.8(8) ?
C18 C8 C9 C10 . . . . -171.6(4) ?
N1 C8 C9 C13 . . . . -174.8(5) ?
C18 C8 C9 C13 . . . . 1.8(4) ?
C13 C9 C10 C11 . . . . 4.6(6) ?
C8 C9 C10 C11 . . . . 177.6(4) ?
C9 C10 C11 C12 . . . . -1.1(7) ?
C13 N2 C12 C11 . . . . 2.6(6) ?
C10 C11 C12 N2 . . . . -2.8(7) ?
C12 N2 C13 C9 . . . . 1.5(6) ?
C12 N2 C13 C14 . . . . -176.8(4) ?
C10 C9 C13 N2 . . . . -5.1(6) ?
C8 C9 C13 N2 . . . . -179.8(4) ?
C10 C9 C13 C14 . . . . 173.3(4) ?
C8 C9 C13 C14 . . . . -1.3(4) ?
C15 N3 C14 C18 . . . . 0.1(6) ?
C15 N3 C14 C13 . . . . 177.1(4) ?
N2 C13 C14 N3 . . . . 1.3(7) ?
C9 C13 C14 N3 . . . . -177.2(4) ?
N2 C13 C14 C18 . . . . 178.7(4) ?
C9 C13 C14 C18 . . . . 0.2(5) ?
C14 N3 C15 C16 . . . . 0.4(7) ?
N3 C15 C16 C17 . . . . -0.4(8) ?
C15 C16 C17 C18 . . . . 0.0(7) ?
C16 C17 C18 C14 . . . . 0.4(6) ?
C16 C17 C18 C8 . . . . -178.2(4) ?
N3 C14 C18 C17 . . . . -0.5(6) ?
C13 C14 C18 C17 . . . . -178.0(4) ?
N3 C14 C18 C8 . . . . 178.5(4) ?
C13 C14 C18 C8 . . . . 0.9(4) ?
N1 C8 C18 C17 . . . . -5.8(7) ?
C9 C8 C18 C17 . . . . 177.0(4) ?
N1 C8 C18 C14 . . . . 175.5(4) ?
C9 C8 C18 C14 . . . . -1.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656138
2 PubChem 74766574
