#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222186.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_2222186
loop_
_publ_author_name
'Zhang, Cai-Li'
'Ye, Ping-Ping'
'Du, Zhi-Qiang'
_publ_section_title
;
 1,1',2,2'-Tetramethyl-3,3'-(4-methoxybenzylidene)di-1H-indole
;
_journal_coeditor_code           XU2523
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1332
_journal_paper_doi               10.1107/S1600536809017759
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H28 N2 O'
_chemical_formula_moiety         'C28 H28 N2 O'
_chemical_formula_sum            'C28 H28 N2 O'
_chemical_formula_weight         408.52
_chemical_name_systematic
;
1,1',2,2'-Tetramethyl-3,3'-(4-methoxybenzylidene)di-1H-indole
;
_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                 97.1740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6647(8)
_cell_length_b                   13.2088(10)
_cell_length_c                   16.1494(13)
_cell_measurement_reflns_used    6354
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.158
_cell_measurement_theta_min      4.871
_cell_volume                     2257.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11505
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0441
_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)+(0.1047P)²+0.8752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                3196
_reflns_number_total             3955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2523.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222186
_cod_database_fobs_code          2222186
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
N N1 0.63286(14) 0.32330(11) 0.89904(8) 0.0421(4) Uani d . 1 . .
N N2 0.23060(12) 0.47645(10) 0.62297(8) 0.0358(3) Uani d . 1 . .
O O1 0.73808(18) 0.09952(13) 0.43460(10) 0.0827(5) Uani d . 1 . .
C C1 0.54764(14) 0.35901(11) 0.67122(9) 0.0316(3) Uani d . 1 . .
H H1 0.5937 0.4226 0.6671 0.038 Uiso calc R 1 . .
C C2 0.59177(14) 0.28915(11) 0.60516(9) 0.0334(4) Uani d . 1 . .
C C3 0.72045(16) 0.27569(12) 0.60290(11) 0.0403(4) Uani d . 1 . .
H H3 0.7776 0.3097 0.6414 0.048 Uiso calc R 1 . .
C C4 0.76556(18) 0.21341(14) 0.54521(12) 0.0501(5) Uani d . 1 . .
H H4 0.8522 0.2066 0.5446 0.060 Uiso calc R 1 . .
C C5 0.6831(2) 0.16106(14) 0.48826(12) 0.0529(5) Uani d . 1 . .
C C6 0.5550(2) 0.17324(15) 0.48860(12) 0.0544(5) Uani d . 1 . .
H H6 0.4984 0.1387 0.4502 0.065 Uiso calc R 1 . .
C C7 0.51073(17) 0.23765(13) 0.54694(11) 0.0435(4) Uani d . 1 . .
H H7 0.4240 0.2460 0.5464 0.052 Uiso calc R 1 . .
C C8 0.6598(4) 0.0526(3) 0.36972(17) 0.1146(13) Uani d . 1 . .
H H8A 0.7107 0.0159 0.3349 0.172 Uiso calc R 1 . .
H H8B 0.6113 0.1031 0.3371 0.172 Uiso calc R 1 . .
H H8C 0.6036 0.0066 0.3927 0.172 Uiso calc R 1 . .
C C9 0.58732(14) 0.32027(11) 0.75930(9) 0.0319(3) Uani d . 1 . .
C C10 0.62303(14) 0.21961(11) 0.78731(10) 0.0317(3) Uani d . 1 . .
C C11 0.63396(15) 0.12468(12) 0.74924(10) 0.0373(4) Uani d . 1 . .
H H11 0.6147 0.1177 0.6918 0.045 Uiso calc R 1 . .
C C12 0.67336(16) 0.04226(12) 0.79772(11) 0.0423(4) Uani d . 1 . .
H H12 0.6806 -0.0203 0.7724 0.051 Uiso calc R 1 . .
C C13 0.70262(16) 0.05046(13) 0.88377(11) 0.0446(4) Uani d . 1 . .
H H13 0.7297 -0.0065 0.9148 0.054 Uiso calc R 1 . .
C C14 0.69222(16) 0.14123(14) 0.92376(11) 0.0428(4) Uani d . 1 . .
H H14 0.7117 0.1467 0.9813 0.051 Uiso calc R 1 . .
C C15 0.65141(14) 0.22480(12) 0.87502(10) 0.0355(4) Uani d . 1 . .
C C16 0.59485(15) 0.38016(12) 0.82871(10) 0.0377(4) Uani d . 1 . .
C C17 0.6468(2) 0.35910(17) 0.98459(12) 0.0627(6) Uani d . 1 . .
H H17A 0.6664 0.3030 1.0218 0.094 Uiso calc R 1 . .
H H17B 0.5693 0.3901 0.9960 0.094 Uiso calc R 1 . .
H H17C 0.7139 0.4079 0.9926 0.094 Uiso calc R 1 . .
C C18 0.5666(2) 0.49042(14) 0.83534(13) 0.0561(5) Uani d . 1 . .
H H18A 0.6390 0.5245 0.8638 0.084 Uiso calc R 1 . .
H H18B 0.4958 0.4992 0.8660 0.084 Uiso calc R 1 . .
H H18C 0.5467 0.5185 0.7804 0.084 Uiso calc R 1 . .
C C19 0.40945(14) 0.38686(11) 0.65659(9) 0.0314(3) Uani d . 1 . .
C C20 0.30467(14) 0.32631(11) 0.67439(9) 0.0325(4) Uani d . 1 . .
C C21 0.29216(16) 0.22881(12) 0.70659(10) 0.0395(4) Uani d . 1 . .
H H21 0.3633 0.1891 0.7218 0.047 Uiso calc R 1 . .
C C22 0.17413(17) 0.19248(14) 0.71551(11) 0.0455(4) Uani d . 1 . .
H H22 0.1659 0.1277 0.7368 0.055 Uiso calc R 1 . .
C C23 0.06594(17) 0.25115(15) 0.69312(12) 0.0484(4) Uani d . 1 . .
H H23 -0.0130 0.2249 0.7000 0.058 Uiso calc R 1 . .
C C24 0.07467(16) 0.34710(14) 0.66114(11) 0.0438(4) Uani d . 1 . .
H H24 0.0028 0.3859 0.6458 0.053 Uiso calc R 1 . .
C C25 0.19443(15) 0.38423(12) 0.65254(9) 0.0339(4) Uani d . 1 . .
C C26 0.36095(14) 0.47703(11) 0.62486(9) 0.0322(3) Uani d . 1 . .
C C27 0.14395(17) 0.55850(14) 0.59566(12) 0.0477(4) Uani d . 1 . .
H H27A 0.0825 0.5654 0.6340 0.072 Uiso calc R 1 . .
H H27B 0.1018 0.5437 0.5410 0.072 Uiso calc R 1 . .
H H27C 0.1904 0.6206 0.5940 0.072 Uiso calc R 1 . .
C C28 0.42723(17) 0.56692(13) 0.59485(11) 0.0440(4) Uani d . 1 . .
H H28A 0.4049 0.6263 0.6240 0.066 Uiso calc R 1 . .
H H28B 0.4025 0.5756 0.5361 0.066 Uiso calc R 1 . .
H H28C 0.5169 0.5566 0.6051 0.066 Uiso calc R 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
C15 N1 C16 . . 108.65(13) ?
C15 N1 C17 . . 125.05(15) ?
C16 N1 C17 . . 126.26(15) ?
C25 N2 C26 . . 108.65(12) ?
C25 N2 C27 . . 124.55(14) ?
C26 N2 C27 . . 126.80(14) ?
C5 O1 C8 . . 118.2(2) ?
C19 C1 C9 . . 112.38(12) ?
C19 C1 C2 . . 114.70(13) ?
C9 C1 C2 . . 112.06(12) ?
C19 C1 H1 . . 105.6 ?
C9 C1 H1 . . 105.6 ?
C2 C1 H1 . . 105.6 ?
C7 C2 C3 . . 117.22(15) ?
C7 C2 C1 . . 123.63(14) ?
C3 C2 C1 . . 119.15(14) ?
C4 C3 C2 . . 121.69(17) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.34(18) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
O1 C5 C4 . . 115.59(19) ?
O1 C5 C6 . . 125.1(2) ?
C4 C5 C6 . . 119.35(17) ?
C5 C6 C7 . . 119.62(18) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C2 C7 C6 . . 121.77(17) ?
C2 C7 H7 . . 119.1 ?
C6 C7 H7 . . 119.1 ?
O1 C8 H8A . . 109.5 ?
O1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C16 C9 C10 . . 106.89(13) ?
C16 C9 C1 . . 123.61(14) ?
C10 C9 C1 . . 129.50(14) ?
C11 C10 C15 . . 117.53(14) ?
C11 C10 C9 . . 135.90(15) ?
C15 C10 C9 . . 106.57(13) ?
C12 C11 C10 . . 119.50(15) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 121.45(16) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C14 C13 C12 . . 121.14(16) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C15 . . 117.65(16) ?
C13 C14 H14 . . 121.2 ?
C15 C14 H14 . . 121.2 ?
N1 C15 C14 . . 129.36(15) ?
N1 C15 C10 . . 107.91(13) ?
C14 C15 C10 . . 122.72(15) ?
C9 C16 N1 . . 109.97(14) ?
C9 C16 C18 . . 129.17(16) ?
N1 C16 C18 . . 120.86(15) ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C26 C19 C20 . . 107.00(13) ?
C26 C19 C1 . . 125.84(14) ?
C20 C19 C1 . . 127.15(13) ?
C21 C20 C25 . . 118.45(14) ?
C21 C20 C19 . . 134.46(14) ?
C25 C20 C19 . . 107.09(13) ?
C22 C21 C20 . . 119.45(16) ?
C22 C21 H21 . . 120.3 ?
C20 C21 H21 . . 120.3 ?
C21 C22 C23 . . 121.13(17) ?
C21 C22 H22 . . 119.4 ?
C23 C22 H22 . . 119.4 ?
C24 C23 C22 . . 120.98(16) ?
C24 C23 H23 . . 119.5 ?
C22 C23 H23 . . 119.5 ?
C23 C24 C25 . . 117.91(16) ?
C23 C24 H24 . . 121.0 ?
C25 C24 H24 . . 121.0 ?
N2 C25 C24 . . 130.18(15) ?
N2 C25 C20 . . 107.76(13) ?
C24 C25 C20 . . 122.07(15) ?
C19 C26 N2 . . 109.49(13) ?
C19 C26 C28 . . 129.77(14) ?
N2 C26 C28 . . 120.74(13) ?
N2 C27 H27A . . 109.5 ?
N2 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
N2 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C26 C28 H28A . . 109.5 ?
C26 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C26 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
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 C15 . 1.379(2) ?
N1 C16 . 1.380(2) ?
N1 C17 . 1.450(2) ?
N2 C25 . 1.381(2) ?
N2 C26 . 1.3867(19) ?
N2 C27 . 1.457(2) ?
O1 C5 . 1.372(2) ?
O1 C8 . 1.401(4) ?
C1 C19 . 1.509(2) ?
C1 C9 . 1.521(2) ?
C1 C2 . 1.529(2) ?
C1 H1 . 0.9800 ?
C2 C7 . 1.375(2) ?
C2 C3 . 1.389(2) ?
C3 C4 . 1.374(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(3) ?
C6 C7 . 1.395(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C16 . 1.366(2) ?
C9 C10 . 1.440(2) ?
C10 C11 . 1.408(2) ?
C10 C15 . 1.413(2) ?
C11 C12 . 1.376(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.390(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.373(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.394(2) ?
C14 H14 . 0.9300 ?
C16 C18 . 1.494(2) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C26 . 1.372(2) ?
C19 C20 . 1.432(2) ?
C20 C21 . 1.401(2) ?
C20 C25 . 1.410(2) ?
C21 C22 . 1.371(2) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.400(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.376(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.391(2) ?
C24 H24 . 0.9300 ?
C26 C28 . 1.493(2) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C28 H28A . 0.9600 ?
C28 H28B . 0.9600 ?
C28 H28C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742376
