#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230769.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_2230769
loop_
_publ_author_name
'Wang, Juangang'
'Yang, Peipei'
'Yang, Jin'
_publ_section_title
;
 N⁴,N^4'^-Bis(4-methoxybenzylidene)-3,3'-dimethylbenzidine
;
_journal_coeditor_code           KP2337
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1753
_journal_paper_doi               10.1107/S1600536811023749
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C30 H28 N2 O2'
_chemical_formula_moiety         'C30 H28 N2 O2'
_chemical_formula_sum            'C30 H28 N2 O2'
_chemical_formula_weight         448.54
_chemical_name_systematic
;
N⁴,N^4'^-Bis(4-methoxybenzylidene)-3,3'-dimethylbenzidine
;
_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                 91.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.644(2)
_cell_length_b                   16.228(3)
_cell_length_c                   12.431(3)
_cell_measurement_reflns_used    9010
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.00
_cell_volume                     2347.9(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11279
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR ;Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0658P)²+1.0766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2350
_reflns_number_total             2667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2337.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230769
_cod_database_fobs_code          2230769
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.14801(6) 0.07986(5) 1.08572(5) 0.01981(19) Uani d . 1 1 . .
N N1 0.36979(7) 0.15477(5) 0.62842(7) 0.0176(2) Uani d . 1 1 . .
C C1 0.20415(11) 0.12644(8) 1.16991(9) 0.0262(3) Uani d . 1 1 . .
H H1A 0.2839(14) 0.1056(10) 1.1839(12) 0.034(4) Uiso d . 1 1 . .
H H1C 0.2050(14) 0.1847(10) 1.1522(12) 0.038(4) Uiso d . 1 1 . .
H H1B 0.1570(13) 0.1177(10) 1.2330(12) 0.037(4) Uiso d . 1 1 . .
C C2 0.18777(9) 0.08948(6) 0.98408(8) 0.0165(2) Uani d . 1 1 . .
C C3 0.28693(9) 0.13363(6) 0.96025(8) 0.0183(2) Uani d . 1 1 . .
H H3A 0.3342(12) 0.1589(8) 1.0165(11) 0.025(3) Uiso d . 1 1 . .
C C4 0.31999(9) 0.13940(6) 0.85410(8) 0.0179(2) Uani d . 1 1 . .
H H4A 0.3903(12) 0.1681(8) 0.8377(10) 0.022(3) Uiso d . 1 1 . .
C C5 0.25488(8) 0.10280(6) 0.77062(8) 0.0163(2) Uani d . 1 1 . .
C C6 0.15643(9) 0.05837(6) 0.79627(8) 0.0179(2) Uani d . 1 1 . .
H H6A 0.1119(11) 0.0334(8) 0.7388(10) 0.021(3) Uiso d . 1 1 . .
C C7 0.12313(9) 0.05104(6) 0.90185(8) 0.0179(2) Uani d . 1 1 . .
H H7A 0.0561(12) 0.0194(8) 0.9196(10) 0.024(3) Uiso d . 1 1 . .
C C8 0.28718(8) 0.10911(6) 0.65788(8) 0.0176(2) Uani d . 1 1 . .
H H8A 0.2396(11) 0.0762(8) 0.6043(10) 0.020(3) Uiso d . 1 1 . .
C C9 0.40025(8) 0.15379(6) 0.51899(8) 0.0162(2) Uani d . 1 1 . .
C C10 0.43005(8) 0.22903(6) 0.47132(8) 0.0159(2) Uani d . 1 1 . .
C C11 0.46879(8) 0.22851(6) 0.36602(8) 0.0165(2) Uani d . 1 1 . .
H H11A 0.4919(11) 0.2820(9) 0.3346(10) 0.023(3) Uiso d . 1 1 . .
C C12 0.47841(8) 0.15556(6) 0.30593(7) 0.0160(2) Uani d . 1 1 . .
C C13 0.44641(9) 0.08169(6) 0.35559(8) 0.0180(2) Uani d . 1 1 . .
H H13A 0.4501(11) 0.0292(8) 0.3175(10) 0.019(3) Uiso d . 1 1 . .
C C14 0.40833(9) 0.08084(6) 0.46040(8) 0.0183(2) Uani d . 1 1 . .
H H14A 0.3897(12) 0.0279(8) 0.4927(10) 0.024(3) Uiso d . 1 1 . .
C C15 0.41802(9) 0.30788(7) 0.53365(8) 0.0199(2) Uani d . 1 1 . .
H H15C 0.3378(12) 0.3186(9) 0.5538(11) 0.028(3) Uiso d . 1 1 . .
H H15B 0.4624(13) 0.3043(9) 0.6036(12) 0.032(4) Uiso d . 1 1 . .
H H15A 0.4450(12) 0.3550(8) 0.4925(11) 0.025(3) Uiso 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'
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 O1 C1 . . 117.07(8) ?
C8 N1 C9 . . 118.82(9) ?
O1 C1 H1A . . 110.5(9) ?
O1 C1 H1C . . 110.8(9) ?
H1A C1 H1C . . 110.7(13) ?
O1 C1 H1B . . 104.7(9) ?
H1A C1 H1B . . 110.6(12) ?
H1C C1 H1B . . 109.4(13) ?
O1 C2 C7 . . 115.77(9) ?
O1 C2 C3 . . 124.00(9) ?
C7 C2 C3 . . 120.23(9) ?
C4 C3 C2 . . 119.37(10) ?
C4 C3 H3A . . 119.3(8) ?
C2 C3 H3A . . 121.3(8) ?
C3 C4 C5 . . 121.10(9) ?
C3 C4 H4A . . 119.5(8) ?
C5 C4 H4A . . 119.4(8) ?
C4 C5 C6 . . 118.62(9) ?
C4 C5 C8 . . 122.06(9) ?
C6 C5 C8 . . 119.33(9) ?
C7 C6 C5 . . 121.02(10) ?
C7 C6 H6A . . 120.6(8) ?
C5 C6 H6A . . 118.4(8) ?
C6 C7 C2 . . 119.64(9) ?
C6 C7 H7A . . 120.9(8) ?
C2 C7 H7A . . 119.4(8) ?
N1 C8 C5 . . 122.17(9) ?
N1 C8 H8A . . 121.5(7) ?
C5 C8 H8A . . 116.3(7) ?
C14 C9 C10 . . 119.73(9) ?
C14 C9 N1 . . 122.27(9) ?
C10 C9 N1 . . 117.87(9) ?
C11 C10 C9 . . 118.72(9) ?
C11 C10 C15 . . 121.69(9) ?
C9 C10 C15 . . 119.58(9) ?
C10 C11 C12 . . 122.41(9) ?
C10 C11 H11A . . 117.6(7) ?
C12 C11 H11A . . 120.0(7) ?
C13 C12 C11 . . 117.30(9) ?
C13 C12 C12 . 2_655 120.73(6) ?
C11 C12 C12 . 2_655 121.96(6) ?
C14 C13 C12 . . 121.17(9) ?
C14 C13 H13A . . 117.8(7) ?
C12 C13 H13A . . 121.1(7) ?
C13 C14 C9 . . 120.66(9) ?
C13 C14 H14A . . 118.4(7) ?
C9 C14 H14A . . 120.9(7) ?
C10 C15 H15C . . 112.6(8) ?
C10 C15 H15B . . 110.1(9) ?
H15C C15 H15B . . 104.9(11) ?
C10 C15 H15A . . 111.0(8) ?
H15C C15 H15A . . 108.4(11) ?
H15B C15 H15A . . 109.6(12) ?
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
O1 C2 . 1.3677(12) ?
O1 C1 . 1.4325(14) ?
N1 C8 . 1.2767(13) ?
N1 C9 . 1.4164(12) ?
C1 H1A . 0.999(16) ?
C1 H1C . 0.972(17) ?
C1 H1B . 0.981(15) ?
C2 C7 . 1.3978(15) ?
C2 C3 . 1.3982(14) ?
C3 C4 . 1.3891(14) ?
C3 H3A . 0.968(14) ?
C4 C5 . 1.3987(15) ?
C4 H4A . 0.969(14) ?
C5 C6 . 1.3993(14) ?
C5 C8 . 1.4657(13) ?
C6 C7 . 1.3851(14) ?
C6 H6A . 0.960(13) ?
C7 H7A . 0.965(14) ?
C8 H8A . 1.006(13) ?
C9 C14 . 1.3946(15) ?
C9 C10 . 1.4054(14) ?
C10 C11 . 1.3976(14) ?
C10 C15 . 1.5046(14) ?
C11 C12 . 1.4061(14) ?
C11 H11A . 0.992(14) ?
C12 C13 . 1.4039(14) ?
C12 C12 2_655 1.4930(18) ?
C13 C14 . 1.3892(14) ?
C13 H13A . 0.975(13) ?
C14 H14A . 0.976(13) ?
C15 H15C . 0.990(14) ?
C15 H15B . 1.000(15) ?
C15 H15A . 0.977(14) ?
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
C6 H6A O1 6_555 0.960(13) 2.688(13) 3.4462(15) 136.32
