#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151203.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_7151203
loop_
_publ_author_name
'Setsune, Jun-ichiro'
'Tanabe, Aya'
'Watanabe, Junko'
'Maeda, Satoshi'
_publ_section_title
;
 Synthesis of bis(azafulvene)s by dehydration of hydroxymethylpyrrole
 derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2247
_journal_page_last               2252
_journal_paper_doi               10.1039/b518340e
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.45
_chemical_name_common
6,6f-Diphenyl-2,2f-bis(azafulvenyl)-gem-dimethylmethane
_chemical_name_systematic
;
6,6f-Diphenyl-2,2f-bis(azafulvenyl)-gem-dimethylmethane
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.135(3)
_cell_length_b                   38.228(8)
_cell_length_c                   6.1877(12)
_cell_measurement_reflns_used    632
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.226
_cell_measurement_theta_min      3.194
_cell_volume                     4053.2(14)
_computing_cell_refinement       'Bruker SAINT+ ver. 6.45'
_computing_data_collection       'Bruker SAINT+ ver. 6.45'
_computing_data_reduction        'Bruker SAINT+ ver. 6.45'
_computing_molecular_graphics    'Bruker XSHELL ver. 4.02'
_computing_publication_material  'Bruker SHELXTL ver. 6.14'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5681
_diffrn_reflns_theta_full        27.31
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'program SADABS ver. 2.03 (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0393
_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)+(0.0467P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1359
_reflns_number_total             2076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b518340e.txt
_cod_data_source_block           (9)
_cod_original_cell_volume        4053.1(14)
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               7151203
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42971(10) 0.00177(5) 0.6047(3) 0.0569(5) Uani 1 1 d . . .
C2 C 0.40798(13) -0.02539(6) 0.7582(4) 0.0691(6) Uani 1 1 d . . .
C3 C 0.34603(13) -0.01351(6) 0.8653(5) 0.0717(6) Uani 1 1 d . . .
C4 C 0.32894(11) 0.02083(5) 0.7792(3) 0.0581(5) Uani 1 1 d . . .
C5 C 0.27170(11) 0.04235(6) 0.8486(4) 0.0664(6) Uani 1 1 d . . .
C6 C 0.24845(11) 0.07671(6) 0.7717(4) 0.0655(6) Uani 1 1 d . . .
C7 C 0.19883(16) 0.09639(7) 0.8976(6) 0.0917(8) Uani 1 1 d . . .
C8 C 0.17549(19) 0.12919(8) 0.8337(8) 0.1150(12) Uani 1 1 d . . .
C9 C 0.19986(17) 0.14249(8) 0.6387(7) 0.1034(10) Uani 1 1 d . . .
C10 C 0.24842(17) 0.12323(7) 0.5140(5) 0.0905(8) Uani 1 1 d . . .
C11 C 0.27298(15) 0.09087(6) 0.5766(4) 0.0781(7) Uani 1 1 d . . .
C12 C 0.5000 0.0000 0.4564(4) 0.0645(8) Uani 1 2 d S . .
C13 C 0.50480(19) 0.03307(9) 0.3191(5) 0.0912(8) Uani 1 1 d . . .
H2 H 0.4352(13) -0.0487(6) 0.783(4) 0.095(7) Uiso 1 1 d . . .
H3 H 0.3121(13) -0.0252(5) 0.968(4) 0.082(7) Uiso 1 1 d . . .
H5 H 0.2462(12) 0.0324(5) 0.976(4) 0.075(6) Uiso 1 1 d . . .
H7 H 0.1786(17) 0.0876(7) 1.033(6) 0.128(11) Uiso 1 1 d . . .
H8 H 0.1423(18) 0.1426(8) 0.917(6) 0.123(11) Uiso 1 1 d . . .
H9 H 0.1800(16) 0.1639(8) 0.614(5) 0.115(10) Uiso 1 1 d . . .
H10 H 0.2699(16) 0.1336(7) 0.377(6) 0.110(9) Uiso 1 1 d . . .
H11 H 0.3050(12) 0.0771(6) 0.501(4) 0.073(7) Uiso 1 1 d . . .
H13A H 0.5496(16) 0.0327(7) 0.231(5) 0.108(9) Uiso 1 1 d . . .
H13B H 0.4479(18) 0.0331(7) 0.231(5) 0.127(11) Uiso 1 1 d . . .
H13C H 0.5031(14) 0.0556(7) 0.414(5) 0.101(9) Uiso 1 1 d . . .
N1 N 0.38299(9) 0.02872(4) 0.6159(3) 0.0598(4) Uani 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'
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
N1 C1 C2 111.79(18) . . ?
N1 C1 C12 123.65(16) . . ?
C2 C1 C12 124.50(16) . . ?
C3 C2 C1 106.58(19) . . ?
C2 C3 C4 106.7(2) . . ?
C5 C4 N1 125.27(19) . . ?
C5 C4 C3 125.6(2) . . ?
N1 C4 C3 109.07(17) . . ?
C4 C5 C6 130.2(2) . . ?
C7 C6 C11 117.8(2) . . ?
C7 C6 C5 118.6(2) . . ?
C11 C6 C5 123.7(2) . . ?
C8 C7 C6 121.0(3) . . ?
C7 C8 C9 120.1(3) . . ?
C10 C9 C8 119.1(3) . . ?
C9 C10 C11 121.5(3) . . ?
C10 C11 C6 120.5(3) . . ?
C1 C12 C1 105.5(2) . 2_655 ?
C1 C12 C13 109.36(16) . 2_655 ?
C1 C12 C13 110.06(13) 2_655 2_655 ?
C1 C12 C13 110.06(13) . . ?
C1 C12 C13 109.36(16) 2_655 . ?
C13 C12 C13 112.3(3) 2_655 . ?
C1 N1 C4 105.83(15) . . ?
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
C1 N1 1.306(2) . ?
C1 C2 1.456(3) . ?
C1 C12 1.516(3) . ?
C2 C3 1.331(3) . ?
C3 C4 1.446(3) . ?
C4 C5 1.350(3) . ?
C4 N1 1.404(3) . ?
C5 C6 1.453(3) . ?
C6 C7 1.377(4) . ?
C6 C11 1.388(3) . ?
C7 C8 1.374(4) . ?
C8 C9 1.375(5) . ?
C9 C10 1.353(4) . ?
C10 C11 1.363(3) . ?
C12 C1 1.516(3) 2_655 ?
C12 C13 1.525(3) 2_655 ?
C12 C13 1.525(3) . ?
