#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220438.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_2220438
loop_
_publ_author_name
'Cang, Hui'
'Jin, Dong'
'Wang, Si-Qing'
'Xu, Bin'
'Wang, Jin-Tang'
_publ_section_title
;
 N-(4,5-Diazafluoren-9-ylidene)-4-methylaniline
;
_journal_coeditor_code           BX2187
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o6
_journal_paper_doi               10.1107/S1600536808039627
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H13 N3'
_chemical_formula_moiety         'C18 H13 N3'
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31
_chemical_name_systematic
;
N-(4,5-Diazafluoren-9-ylidene)-4-methylaniline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.11(3)
_cell_angle_beta                 87.48(3)
_cell_angle_gamma                85.79(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5970(15)
_cell_length_b                   8.6100(17)
_cell_length_c                   10.998(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     699.1(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2742
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0582
_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)+(0.05P)²+0.85P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                1829
_reflns_number_total             2534
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2187.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220438
_cod_database_fobs_code          2220438
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.2577(3) 1.3579(3) 0.5598(2) 0.0539(7) Uani d . 1 . .
C C1 0.0220(6) 1.2134(6) 1.0717(3) 0.0953(14) Uani d . 1 . .
H H1B -0.0898 1.2705 1.0794 0.143 Uiso calc R 1 . .
H H1C 0.1063 1.2457 1.1223 0.143 Uiso calc R 1 . .
H H1D 0.0091 1.1008 1.0992 0.143 Uiso calc R 1 . .
N N2 0.2970(3) 0.8734(3) 0.3984(2) 0.0507(6) Uani d . 1 . .
C C2 0.0855(5) 1.2499(5) 0.9378(3) 0.0658(9) Uani d . 1 . .
N N3 0.4535(3) 1.1454(3) 0.2071(2) 0.0526(6) Uani d . 1 . .
C C3 0.2450(4) 1.1836(4) 0.8993(3) 0.0584(8) Uani d . 1 . .
H H3B 0.3152 1.1156 0.9583 0.070 Uiso calc R 1 . .
C C4 0.3018(4) 1.2158(4) 0.7759(3) 0.0551(8) Uani d . 1 . .
H H4A 0.4094 1.1703 0.7528 0.066 Uiso calc R 1 . .
C C5 0.1987(4) 1.3158(3) 0.6866(3) 0.0501(7) Uani d . 1 . .
C C6 0.0411(4) 1.3877(4) 0.7236(3) 0.0602(8) Uani d . 1 . .
H H6A -0.0268 1.4590 0.6650 0.072 Uiso calc R 1 . .
C C7 -0.0137(5) 1.3531(5) 0.8469(3) 0.0723(10) Uani d . 1 . .
H H7A -0.1203 1.4002 0.8701 0.087 Uiso calc R 1 . .
C C8 0.2867(4) 1.2521(3) 0.4951(2) 0.0432(6) Uani d . 1 . .
C C9 0.2518(3) 1.0803(3) 0.5183(2) 0.0398(6) Uani d . 1 . .
C C10 0.1712(4) 0.9757(3) 0.6156(3) 0.0463(7) Uani d . 1 . .
H H10A 0.1279 1.0086 0.6868 0.056 Uiso calc R 1 . .
C C11 0.1576(4) 0.8219(4) 0.6030(3) 0.0490(7) Uani d . 1 . .
H H11A 0.1044 0.7485 0.6663 0.059 Uiso calc R 1 . .
C C12 0.2236(4) 0.7763(4) 0.4952(3) 0.0537(8) Uani d . 1 . .
H H12A 0.2157 0.6705 0.4907 0.064 Uiso calc R 1 . .
C C13 0.3085(3) 1.0227(3) 0.4114(2) 0.0421(6) Uani d . 1 . .
C C14 0.3829(3) 1.1547(3) 0.3185(2) 0.0429(6) Uani d . 1 . .
C C15 0.5163(4) 1.2817(4) 0.1427(3) 0.0586(8) Uani d . 1 . .
H H15A 0.5670 1.2820 0.0641 0.070 Uiso calc R 1 . .
C C16 0.5114(4) 1.4213(4) 0.1839(3) 0.0617(9) Uani d . 1 . .
H H16A 0.5590 1.5111 0.1338 0.074 Uiso calc R 1 . .
C C17 0.4364(4) 1.4296(4) 0.2994(3) 0.0545(8) Uani d . 1 . .
H H17A 0.4317 1.5228 0.3292 0.065 Uiso calc R 1 . .
C C18 0.3691(4) 1.2917(3) 0.3673(2) 0.0457(7) 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'
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
C8 N1 C5 . . 121.0(3) ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C12 N2 C13 . . 115.1(2) ?
C7 C2 C3 . . 117.2(3) ?
C7 C2 C1 . . 120.8(3) ?
C3 C2 C1 . . 122.0(4) ?
C14 N3 C15 . . 114.0(3) ?
C4 C3 C2 . . 121.8(3) ?
C4 C3 H3B . . 119.1 ?
C2 C3 H3B . . 119.1 ?
C3 C4 C5 . . 119.9(3) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C4 C5 C6 . . 119.2(3) ?
C4 C5 N1 . . 121.3(3) ?
C6 C5 N1 . . 119.3(3) ?
C7 C6 C5 . . 119.9(3) ?
C7 C6 H6A . . 120.1 ?
C5 C6 H6A . . 120.1 ?
C6 C7 C2 . . 121.9(3) ?
C6 C7 H7A . . 119.1 ?
C2 C7 H7A . . 119.1 ?
N1 C8 C9 . . 133.1(3) ?
N1 C8 C18 . . 121.3(3) ?
C9 C8 C18 . . 105.6(2) ?
C10 C9 C13 . . 117.7(3) ?
C10 C9 C8 . . 133.8(2) ?
C13 C9 C8 . . 108.3(2) ?
C11 C10 C9 . . 117.7(3) ?
C11 C10 H10A . . 121.2 ?
C9 C10 H10A . . 121.2 ?
C10 C11 C12 . . 119.8(3) ?
C10 C11 H11A . . 120.1 ?
C12 C11 H11A . . 120.1 ?
N2 C12 C11 . . 124.6(3) ?
N2 C12 H12A . . 117.7 ?
C11 C12 H12A . . 117.7 ?
N2 C13 C9 . . 125.1(3) ?
N2 C13 C14 . . 126.4(2) ?
C9 C13 C14 . . 108.5(2) ?
N3 C14 C18 . . 125.3(3) ?
N3 C14 C13 . . 126.1(3) ?
C18 C14 C13 . . 108.6(2) ?
N3 C15 C16 . . 124.8(3) ?
N3 C15 H15A . . 117.6 ?
C16 C15 H15A . . 117.6 ?
C15 C16 C17 . . 120.6(3) ?
C15 C16 H16A . . 119.7 ?
C17 C16 H16A . . 119.7 ?
C18 C17 C16 . . 115.9(3) ?
C18 C17 H17A . . 122.0 ?
C16 C17 H17A . . 122.0 ?
C17 C18 C14 . . 119.4(3) ?
C17 C18 C8 . . 131.6(3) ?
C14 C18 C8 . . 108.9(2) ?
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
N1 C8 . 1.277(3) ?
N1 C5 . 1.422(4) ?
C1 C2 . 1.501(5) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
N2 C12 . 1.327(4) ?
N2 C13 . 1.334(4) ?
C2 C7 . 1.388(5) ?
C2 C3 . 1.391(5) ?
N3 C14 . 1.332(3) ?
N3 C15 . 1.337(4) ?
C3 C4 . 1.380(4) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.382(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.394(4) ?
C6 C7 . 1.374(4) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 C9 . 1.486(4) ?
C8 C18 . 1.491(4) ?
C9 C10 . 1.387(4) ?
C9 C13 . 1.414(4) ?
C10 C11 . 1.373(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.392(4) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 C14 . 1.477(4) ?
C14 C18 . 1.397(4) ?
C15 C16 . 1.374(5) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.383(4) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.375(4) ?
C17 H17A . 0.9300 ?
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
C7 C2 C3 C4 . . . . -1.2(5) ?
C1 C2 C3 C4 . . . . 179.2(3) ?
C2 C3 C4 C5 . . . . -0.4(5) ?
C3 C4 C5 C6 . . . . 2.5(5) ?
C3 C4 C5 N1 . . . . 176.7(3) ?
C8 N1 C5 C4 . . . . 63.1(4) ?
C8 N1 C5 C6 . . . . -122.7(3) ?
C4 C5 C6 C7 . . . . -2.9(5) ?
N1 C5 C6 C7 . . . . -177.3(3) ?
C5 C6 C7 C2 . . . . 1.3(6) ?
C3 C2 C7 C6 . . . . 0.7(6) ?
C1 C2 C7 C6 . . . . -179.7(4) ?
C5 N1 C8 C9 . . . . 8.7(5) ?
C5 N1 C8 C18 . . . . -172.5(3) ?
N1 C8 C9 C10 . . . . 2.4(5) ?
C18 C8 C9 C10 . . . . -176.5(3) ?
N1 C8 C9 C13 . . . . 178.6(3) ?
C18 C8 C9 C13 . . . . -0.3(3) ?
C13 C9 C10 C11 . . . . 2.2(4) ?
C8 C9 C10 C11 . . . . 178.1(3) ?
C9 C10 C11 C12 . . . . 0.0(4) ?
C13 N2 C12 C11 . . . . 1.5(4) ?
C10 C11 C12 N2 . . . . -2.0(5) ?
C12 N2 C13 C9 . . . . 0.9(4) ?
C12 N2 C13 C14 . . . . -179.6(3) ?
C10 C9 C13 N2 . . . . -2.8(4) ?
C8 C9 C13 N2 . . . . -179.6(2) ?
C10 C9 C13 C14 . . . . 177.7(2) ?
C8 C9 C13 C14 . . . . 0.8(3) ?
C15 N3 C14 C18 . . . . 1.2(4) ?
C15 N3 C14 C13 . . . . -178.0(3) ?
N2 C13 C14 N3 . . . . -1.2(4) ?
C9 C13 C14 N3 . . . . 178.4(2) ?
N2 C13 C14 C18 . . . . 179.5(3) ?
C9 C13 C14 C18 . . . . -1.0(3) ?
C14 N3 C15 C16 . . . . 0.0(4) ?
N3 C15 C16 C17 . . . . -0.6(5) ?
C15 C16 C17 C18 . . . . -0.1(4) ?
C16 C17 C18 C14 . . . . 1.2(4) ?
C16 C17 C18 C8 . . . . 177.0(3) ?
N3 C14 C18 C17 . . . . -1.9(4) ?
C13 C14 C18 C17 . . . . 177.4(2) ?
N3 C14 C18 C8 . . . . -178.6(2) ?
C13 C14 C18 C8 . . . . 0.7(3) ?
N1 C8 C18 C17 . . . . 4.5(5) ?
C9 C8 C18 C17 . . . . -176.4(3) ?
N1 C8 C18 C14 . . . . -179.3(3) ?
C9 C8 C18 C14 . . . . -0.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655682
