#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:01:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180284 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/70/7117084.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_7117084
loop_
_publ_author_name
'Takayuki Tanaka'
'Atsuhiro Osuka'
_publ_section_title
;
 Tetracoordinate silicon complexes of 1,2-bis(indol-2-yl)benzene as
 blue-emitting dyes in the solid state
;
_journal_name_full               Chem.Commun.
_journal_page_first              8123
_journal_paper_doi               10.1039/C5cc01625H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H20 N2 Si, C H Cl3'
_chemical_formula_sum            'C25 H21 Cl3 N2 Si'
_chemical_formula_weight         483.88
_chemical_name_systematic
'1,2-bis(indol-2-yl)benzene dimethylsilyl complex'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-21 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.368(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6810(19)
_cell_length_b                   19.442(4)
_cell_length_c                   11.152(2)
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.1
_cell_volume                     2270.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14603
_diffrn_reflns_theta_full        65.94
_diffrn_reflns_theta_max         65.94
_diffrn_reflns_theta_min         6.80
_exptl_absorpt_coefficient_mu    4.281
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.4142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0277
_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)+(0.0448P)²+1.0494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                3631
_reflns_number_total             3848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01625h3.cif
_cod_data_source_block           41007ta
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7117084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.17368(12) 0.28091(7) 0.02265(13) 0.0129(3) Uani 1 1 d . . .
C2 C 0.20075(13) 0.33751(7) 0.10119(14) 0.0164(3) Uani 1 1 d . . .
H1 H 0.2591 0.3338 0.1771 0.020 Uiso 1 1 calc R . .
C3 C 0.13980(14) 0.39916(7) 0.06473(14) 0.0199(3) Uani 1 1 d . . .
H2 H 0.1573 0.4382 0.1166 0.024 Uiso 1 1 calc R . .
C4 C 0.05327(14) 0.40542(7) -0.04653(14) 0.0206(3) Uani 1 1 d . . .
H3 H 0.0127 0.4483 -0.0687 0.025 Uiso 1 1 calc R . .
C5 C 0.02625(14) 0.34993(8) -0.12435(14) 0.0182(3) Uani 1 1 d . . .
H4 H -0.0328 0.3543 -0.1998 0.022 Uiso 1 1 calc R . .
C6 C 0.08734(12) 0.28691(7) -0.09040(13) 0.0137(3) Uani 1 1 d . . .
C7 C 0.08033(12) 0.22071(7) -0.14750(13) 0.0140(3) Uani 1 1 d . . .
H5 H 0.0301 0.2089 -0.2249 0.017 Uiso 1 1 calc R . .
C8 C 0.15890(12) 0.17771(7) -0.07058(13) 0.0124(3) Uani 1 1 d . . .
C9 C 0.17812(13) 0.10351(7) -0.09059(12) 0.0125(3) Uani 1 1 d . . .
C10 C 0.06815(13) 0.06311(7) -0.12340(13) 0.0158(3) Uani 1 1 d . . .
H6 H -0.0133 0.0837 -0.1277 0.019 Uiso 1 1 calc R . .
C11 C 0.07572(13) -0.00625(7) -0.14974(13) 0.0173(3) Uani 1 1 d . . .
H7 H 0.0001 -0.0328 -0.1721 0.021 Uiso 1 1 calc R . .
C12 C 0.19452(14) -0.03672(7) -0.14335(13) 0.0162(3) Uani 1 1 d . . .
H8 H 0.2004 -0.0842 -0.1614 0.019 Uiso 1 1 calc R . .
C13 C 0.30447(13) 0.00246(7) -0.11052(12) 0.0141(3) Uani 1 1 d . . .
H9 H 0.3854 -0.0187 -0.1064 0.017 Uiso 1 1 calc R . .
C14 C 0.29873(12) 0.07257(7) -0.08333(12) 0.0117(3) Uani 1 1 d . . .
C15 C 0.42122(12) 0.11011(7) -0.05118(12) 0.0117(3) Uani 1 1 d . . .
C16 C 0.51979(13) 0.10855(7) -0.11243(13) 0.0145(3) Uani 1 1 d . . .
H10 H 0.5220 0.0836 -0.1852 0.017 Uiso 1 1 calc R . .
C17 C 0.61909(13) 0.15133(7) -0.04711(13) 0.0148(3) Uani 1 1 d . . .
C18 C 0.57576(12) 0.17674(7) 0.05646(13) 0.0134(3) Uani 1 1 d . . .
C19 C 0.65398(13) 0.21779(7) 0.14291(14) 0.0176(3) Uani 1 1 d . . .
H11 H 0.6258 0.2337 0.2137 0.021 Uiso 1 1 calc R . .
C20 C 0.77397(14) 0.23459(8) 0.12229(15) 0.0220(3) Uani 1 1 d . . .
H12 H 0.8287 0.2624 0.1801 0.026 Uiso 1 1 calc R . .
C21 C 0.81684(14) 0.21151(8) 0.01811(16) 0.0237(3) Uani 1 1 d . . .
H13 H 0.8990 0.2247 0.0057 0.028 Uiso 1 1 calc R . .
C22 C 0.74092(14) 0.17004(8) -0.06618(15) 0.0206(3) Uani 1 1 d . . .
H14 H 0.7703 0.1542 -0.1364 0.025 Uiso 1 1 calc R . .
C23 C 0.40351(13) 0.23125(7) 0.27109(13) 0.0174(3) Uani 1 1 d . . .
H16 H 0.4370 0.2727 0.2386 0.026 Uiso 1 1 calc R . .
H17 H 0.4724 0.2082 0.3279 0.026 Uiso 1 1 calc R . .
H18 H 0.3355 0.2441 0.3144 0.026 Uiso 1 1 calc R . .
C24 C 0.28063(13) 0.09316(7) 0.20643(13) 0.0167(3) Uani 1 1 d . . .
H19 H 0.2171 0.1050 0.2556 0.025 Uiso 1 1 calc R . .
H20 H 0.3525 0.0692 0.2578 0.025 Uiso 1 1 calc R . .
H21 H 0.2415 0.0631 0.1388 0.025 Uiso 1 1 calc R . .
N1 N 0.21790(10) 0.21258(6) 0.03589(11) 0.0124(2) Uani 1 1 d . . .
N2 N 0.45251(10) 0.15131(6) 0.05411(10) 0.0120(2) Uani 1 1 d . . .
Si1 Si 0.33885(3) 0.172705(18) 0.14431(3) 0.01074(10) Uani 1 1 d . . .
C25 C 0.64642(16) 0.39106(8) 0.01399(15) 0.0251(3) Uani 1 1 d . . .
H15 H 0.6736 0.3418 0.0138 0.030 Uiso 1 1 calc R . .
Cl1 Cl 0.65268(4) 0.42674(2) -0.12953(4) 0.03275(12) Uani 1 1 d . . .
Cl2 Cl 0.48958(4) 0.39355(2) 0.04125(4) 0.03655(13) Uani 1 1 d . . .
Cl3 Cl 0.75288(5) 0.43431(2) 0.13001(4) 0.04229(14) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 C1 N1 130.70(13) . .
C2 C1 C6 120.75(12) . .
N1 C1 C6 108.54(12) . .
C3 C2 C1 117.95(14) . .
C3 C2 H1 121.0 . .
C1 C2 H1 121.0 . .
C2 C3 C4 121.70(14) . .
C2 C3 H2 119.1 . .
C4 C3 H2 119.1 . .
C5 C4 C3 120.66(13) . .
C5 C4 H3 119.7 . .
C3 C4 H3 119.7 . .
C4 C5 C6 118.96(14) . .
C4 C5 H4 120.5 . .
C6 C5 H4 120.5 . .
C5 C6 C1 119.97(13) . .
C5 C6 C7 133.13(13) . .
C1 C6 C7 106.89(12) . .
C8 C7 C6 107.46(12) . .
C8 C7 H5 126.3 . .
C6 C7 H5 126.3 . .
C7 C8 N1 110.75(12) . .
C7 C8 C9 126.14(13) . .
N1 C8 C9 123.07(12) . .
C10 C9 C14 119.06(12) . .
C10 C9 C8 116.86(12) . .
C14 C9 C8 124.03(12) . .
C11 C10 C9 121.34(13) . .
C11 C10 H6 119.3 . .
C9 C10 H6 119.3 . .
C10 C11 C12 119.66(13) . .
C10 C11 H7 120.2 . .
C12 C11 H7 120.2 . .
C13 C12 C11 119.77(13) . .
C13 C12 H8 120.1 . .
C11 C12 H8 120.1 . .
C12 C13 C14 121.39(13) . .
C12 C13 H9 119.3 . .
C14 C13 H9 119.3 . .
C13 C14 C9 118.78(12) . .
C13 C14 C15 117.28(12) . .
C9 C14 C15 123.92(12) . .
C16 C15 N2 110.55(12) . .
C16 C15 C14 126.94(13) . .
N2 C15 C14 122.46(12) . .
C15 C16 C17 107.49(12) . .
C15 C16 H10 126.3 . .
C17 C16 H10 126.3 . .
C22 C17 C18 119.61(14) . .
C22 C17 C16 133.54(14) . .
C18 C17 C16 106.85(12) . .
C19 C18 N2 130.31(13) . .
C19 C18 C17 121.06(13) . .
N2 C18 C17 108.58(12) . .
C20 C19 C18 117.89(14) . .
C20 C19 H11 121.1 . .
C18 C19 H11 121.1 . .
C19 C20 C21 121.71(14) . .
C19 C20 H12 119.1 . .
C21 C20 H12 119.1 . .
C22 C21 C20 120.57(13) . .
C22 C21 H13 119.7 . .
C20 C21 H13 119.7 . .
C21 C22 C17 119.11(15) . .
C21 C22 H14 120.4 . .
C17 C22 H14 120.4 . .
Si1 C23 H16 109.5 . .
Si1 C23 H17 109.5 . .
H16 C23 H17 109.5 . .
Si1 C23 H18 109.5 . .
H16 C23 H18 109.5 . .
H17 C23 H18 109.5 . .
Si1 C24 H19 109.5 . .
Si1 C24 H20 109.5 . .
H19 C24 H20 109.5 . .
Si1 C24 H21 109.5 . .
H19 C24 H21 109.5 . .
H20 C24 H21 109.5 . .
C8 N1 C1 106.35(11) . .
C8 N1 Si1 120.86(9) . .
C1 N1 Si1 132.17(10) . .
C18 N2 C15 106.52(11) . .
C18 N2 Si1 130.74(10) . .
C15 N2 Si1 122.08(9) . .
N1 Si1 N2 101.83(6) . .
N1 Si1 C23 111.58(6) . .
N2 Si1 C23 112.70(6) . .
N1 Si1 C24 111.64(6) . .
N2 Si1 C24 109.54(6) . .
C23 Si1 C24 109.39(7) . .
Cl1 C25 Cl3 110.24(9) . .
Cl1 C25 Cl2 110.77(9) . .
Cl3 C25 Cl2 111.03(9) . .
Cl1 C25 H15 108.2 . .
Cl3 C25 H15 108.2 . .
Cl2 C25 H15 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.401(2) .
C1 N1 1.4079(17) .
C1 C6 1.412(2) .
C2 C3 1.386(2) .
C2 H1 0.9500 .
C3 C4 1.399(2) .
C3 H2 0.9500 .
C4 C5 1.379(2) .
C4 H3 0.9500 .
C5 C6 1.405(2) .
C5 H4 0.9500 .
C6 C7 1.431(2) .
C7 C8 1.3621(19) .
C7 H5 0.9500 .
C8 N1 1.4042(18) .
C8 C9 1.4802(19) .
C9 C10 1.4003(19) .
C9 C14 1.4095(19) .
C10 C11 1.386(2) .
C10 H6 0.9500 .
C11 C12 1.389(2) .
C11 H7 0.9500 .
C12 C13 1.387(2) .
C12 H8 0.9500 .
C13 C14 1.4003(19) .
C13 H9 0.9500 .
C14 C15 1.4793(18) .
C15 C16 1.364(2) .
C15 N2 1.4062(18) .
C16 C17 1.429(2) .
C16 H10 0.9500 .
C17 C22 1.407(2) .
C17 C18 1.415(2) .
C18 C19 1.395(2) .
C18 N2 1.4016(17) .
C19 C20 1.385(2) .
C19 H11 0.9500 .
C20 C21 1.404(2) .
C20 H12 0.9500 .
C21 C22 1.375(2) .
C21 H13 0.9500 .
C22 H14 0.9500 .
C23 Si1 1.8403(14) .
C23 H16 0.9800 .
C23 H17 0.9800 .
C23 H18 0.9800 .
C24 Si1 1.8515(14) .
C24 H19 0.9800 .
C24 H20 0.9800 .
C24 H21 0.9800 .
N1 Si1 1.7652(12) .
N2 Si1 1.7721(12) .
C25 Cl1 1.7577(17) .
C25 Cl3 1.7591(17) .
C25 Cl2 1.7611(17) .
C25 H15 1.0000 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 -178.43(13) . . . .
C6 C1 C2 C3 0.3(2) . . . .
C1 C2 C3 C4 0.3(2) . . . .
C2 C3 C4 C5 -0.3(2) . . . .
C3 C4 C5 C6 -0.2(2) . . . .
C4 C5 C6 C1 0.8(2) . . . .
C4 C5 C6 C7 179.21(14) . . . .
C2 C1 C6 C5 -0.9(2) . . . .
N1 C1 C6 C5 178.14(12) . . . .
C2 C1 C6 C7 -179.66(12) . . . .
N1 C1 C6 C7 -0.65(14) . . . .
C5 C6 C7 C8 -178.26(14) . . . .
C1 C6 C7 C8 0.31(15) . . . .
C6 C7 C8 N1 0.15(15) . . . .
C6 C7 C8 C9 177.79(12) . . . .
C7 C8 C9 C10 -49.5(2) . . . .
N1 C8 C9 C10 127.85(14) . . . .
C7 C8 C9 C14 127.85(15) . . . .
N1 C8 C9 C14 -54.8(2) . . . .
C14 C9 C10 C11 -0.6(2) . . . .
C8 C9 C10 C11 176.94(13) . . . .
C9 C10 C11 C12 0.2(2) . . . .
C10 C11 C12 C13 0.1(2) . . . .
C11 C12 C13 C14 0.0(2) . . . .
C12 C13 C14 C9 -0.4(2) . . . .
C12 C13 C14 C15 -179.06(12) . . . .
C10 C9 C14 C13 0.7(2) . . . .
C8 C9 C14 C13 -176.64(13) . . . .
C10 C9 C14 C15 179.21(13) . . . .
C8 C9 C14 C15 1.9(2) . . . .
C13 C14 C15 C16 47.86(19) . . . .
C9 C14 C15 C16 -130.70(15) . . . .
C13 C14 C15 N2 -129.39(14) . . . .
C9 C14 C15 N2 52.05(19) . . . .
N2 C15 C16 C17 -1.24(15) . . . .
C14 C15 C16 C17 -178.76(12) . . . .
C15 C16 C17 C22 -179.26(15) . . . .
C15 C16 C17 C18 1.32(15) . . . .
C22 C17 C18 C19 -2.7(2) . . . .
C16 C17 C18 C19 176.81(12) . . . .
C22 C17 C18 N2 179.56(12) . . . .
C16 C17 C18 N2 -0.92(15) . . . .
N2 C18 C19 C20 179.07(13) . . . .
C17 C18 C19 C20 1.9(2) . . . .
C18 C19 C20 C21 0.1(2) . . . .
C19 C20 C21 C22 -1.2(2) . . . .
C20 C21 C22 C17 0.4(2) . . . .
C18 C17 C22 C21 1.5(2) . . . .
C16 C17 C22 C21 -177.86(15) . . . .
C7 C8 N1 C1 -0.55(15) . . . .
C9 C8 N1 C1 -178.28(12) . . . .
C7 C8 N1 Si1 -172.61(9) . . . .
C9 C8 N1 Si1 9.66(17) . . . .
C2 C1 N1 C8 179.61(14) . . . .
C6 C1 N1 C8 0.73(14) . . . .
C2 C1 N1 Si1 -9.6(2) . . . .
C6 C1 N1 Si1 171.53(10) . . . .
C19 C18 N2 C15 -177.26(14) . . . .
C17 C18 N2 C15 0.19(14) . . . .
C19 C18 N2 Si1 12.2(2) . . . .
C17 C18 N2 Si1 -170.37(10) . . . .
C16 C15 N2 C18 0.66(15) . . . .
C14 C15 N2 C18 178.31(11) . . . .
C16 C15 N2 Si1 172.23(9) . . . .
C14 C15 N2 Si1 -10.12(17) . . . .
C8 N1 Si1 N2 57.21(11) . . . .
C1 N1 Si1 N2 -112.49(12) . . . .
C8 N1 Si1 C23 177.67(10) . . . .
C1 N1 Si1 C23 7.97(14) . . . .
C8 N1 Si1 C24 -59.59(12) . . . .
C1 N1 Si1 C24 130.71(12) . . . .
C18 N2 Si1 N1 112.34(12) . . . .
C15 N2 Si1 N1 -56.97(11) . . . .
C18 N2 Si1 C23 -7.33(14) . . . .
C15 N2 Si1 C23 -176.64(10) . . . .
C18 N2 Si1 C24 -129.36(12) . . . .
C15 N2 Si1 C24 61.34(12) . . . .
