#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023788.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_4023788
loop_
_publ_author_name
'Masaki Yamamura'
'Naokazu Kano'
'Takayuki Kawashima'
'Tomonari Matsumoto'
'Jun Harada'
'Keiichiro Ogawa'
_publ_contact_author_address
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
_publ_contact_author_email       takayuki@chem.s.u-tokyo.ac.jp
_publ_contact_author_fax         +81-5800-6899
_publ_contact_author_name        'Takayuki Kawashima'
_publ_contact_author_phone       +81-5841-4338
_publ_section_title
;
 Crucial Role of N...Si Interactions in the Solid-State
 Coloration of Disilylazobenzenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8244
_journal_page_last               8249
_journal_paper_doi               10.1021/jo801334a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C38 H32 F2 N2 Si2'
_chemical_formula_sum            'C38 H32 F2 N2 Si2'
_chemical_formula_weight         610.84
_chemical_name_systematic
;
2,2'-Bis(fluorodiphenylsilyl)-4,4'-dimethylazobenzene
;
_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                92.725(6)
_cell_angle_beta                 105.385(6)
_cell_angle_gamma                97.941(6)
_cell_formula_units_Z            1
_cell_length_a                   7.916(4)
_cell_length_b                   8.961(4)
_cell_length_c                   11.390(5)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0863
_cell_volume                     768.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics
'ORTEP-3 for Windows ver 1.08 (Farrugia, 1997-2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
scan:
    Number of images: 600
               Slice: -70.0000 - 110.0000
         Image width: 0.3000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9962
              2theta: 19.6199
scan:
    Number of images: 600
               Slice: -70.0000 - 110.0000
         Image width: 0.3000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9962
              2theta: 19.6199

;
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3-circle
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0722
_diffrn_orient_matrix_UB_12      -0.0100
_diffrn_orient_matrix_UB_13      -0.1108
_diffrn_orient_matrix_UB_21      -0.0982
_diffrn_orient_matrix_UB_22      0.0403
_diffrn_orient_matrix_UB_23      0.0391
_diffrn_orient_matrix_UB_31      0.0072
_diffrn_orient_matrix_UB_32      0.0809
_diffrn_orient_matrix_UB_33      -0.0420
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4942
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_diffrn_source_current           40.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998) Private communication
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0369
_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/['s²(Fo²)+(0.0579P)²+0.2198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                2283
_reflns_number_total             2642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801334a_si_001.cif
_cod_data_source_block           e4a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 
;
_cod_database_code               4023788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Si1 Si 0.32019(6) 0.23993(5) 0.74355(4) 0.01921(17) Uani 1 1 d . . .
F1 F 0.48263(14) 0.37454(12) 0.80124(9) 0.0291(3) Uani 1 1 d . . .
C1 C 0.2236(2) 0.2929(2) 0.58493(15) 0.0184(4) Uani 1 1 d . . .
C2 C 0.2745(2) 0.43550(19) 0.54999(16) 0.0198(4) Uani 1 1 d . . .
H1 H 0.3669 0.5037 0.6055 0.024 Uiso 1 1 calc R . .
C3 C 0.1932(2) 0.4809(2) 0.43512(16) 0.0213(4) Uani 1 1 d . . .
C4 C 0.0571(2) 0.3794(2) 0.35497(16) 0.0232(4) Uani 1 1 d . . .
H2 H -0.0015 0.4095 0.2777 0.028 Uiso 1 1 calc R . .
C5 C 0.0062(2) 0.2367(2) 0.38544(16) 0.0215(4) Uani 1 1 d . . .
H3 H -0.0852 0.1684 0.3293 0.026 Uiso 1 1 calc R . .
C6 C 0.0904(2) 0.19326(19) 0.49986(15) 0.0185(4) Uani 1 1 d . . .
N1 N 0.04657(18) 0.04926(16) 0.54124(13) 0.0189(3) Uani 1 1 d . . .
C7 C 0.4125(2) 0.05921(19) 0.75048(15) 0.0200(4) Uani 1 1 d . . .
C8 C 0.4989(2) 0.0143(2) 0.66558(16) 0.0245(4) Uani 1 1 d . . .
H4 H 0.5086 0.0762 0.6015 0.029 Uiso 1 1 calc R . .
C9 C 0.5713(3) -0.1194(2) 0.67301(17) 0.0291(5) Uani 1 1 d . . .
H5 H 0.6320 -0.1469 0.6156 0.035 Uiso 1 1 calc R . .
C10 C 0.5542(3) -0.2116(2) 0.76444(18) 0.0309(5) Uani 1 1 d . . .
H6 H 0.6020 -0.3034 0.7694 0.037 Uiso 1 1 calc R . .
C11 C 0.4672(3) -0.1701(2) 0.84906(17) 0.0285(4) Uani 1 1 d . . .
H7 H 0.4549 -0.2339 0.9115 0.034 Uiso 1 1 calc R . .
C12 C 0.3985(2) -0.0362(2) 0.84234(16) 0.0240(4) Uani 1 1 d . . .
H8 H 0.3406 -0.0083 0.9013 0.029 Uiso 1 1 calc R . .
C13 C 0.1716(2) 0.2464(2) 0.84537(15) 0.0207(4) Uani 1 1 d . . .
C14 C 0.2148(2) 0.3581(2) 0.94258(16) 0.0245(4) Uani 1 1 d . . .
H9 H 0.3157 0.4336 0.9529 0.029 Uiso 1 1 calc R . .
C15 C 0.1129(3) 0.3611(2) 1.02462(18) 0.0311(5) Uani 1 1 d . . .
H10 H 0.1457 0.4369 1.0913 0.037 Uiso 1 1 calc R . .
C16 C -0.0371(3) 0.2531(2) 1.00920(18) 0.0304(5) Uani 1 1 d . . .
H11 H -0.1069 0.2546 1.0653 0.036 Uiso 1 1 calc R . .
C17 C -0.0841(3) 0.1438(2) 0.91210(17) 0.0281(4) Uani 1 1 d . . .
H12 H -0.1880 0.0712 0.9006 0.034 Uiso 1 1 calc R . .
C18 C 0.0189(2) 0.1387(2) 0.83101(16) 0.0240(4) Uani 1 1 d . . .
H13 H -0.0141 0.0618 0.7652 0.029 Uiso 1 1 calc R . .
C19 C 0.2497(3) 0.6354(2) 0.39953(18) 0.0274(4) Uani 1 1 d . . .
H14 H 0.3390 0.6299 0.3548 0.041 Uiso 1 1 calc R . .
H15 H 0.3004 0.7053 0.4733 0.041 Uiso 1 1 calc R . .
H16 H 0.1466 0.6718 0.3473 0.041 Uiso 1 1 calc R . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
F1 Si1 C13 104.56(8) . . ?
F1 Si1 C7 107.57(8) . . ?
C13 Si1 C7 110.98(8) . . ?
F1 Si1 C1 103.73(7) . . ?
C13 Si1 C1 114.23(8) . . ?
C7 Si1 C1 114.74(8) . . ?
C2 C1 C6 117.76(15) . . ?
C2 C1 Si1 121.22(13) . . ?
C6 C1 Si1 120.92(13) . . ?
C1 C2 C3 121.80(16) . . ?
C1 C2 H1 119.1 . . ?
C3 C2 H1 119.1 . . ?
C4 C3 C2 118.31(16) . . ?
C4 C3 C19 120.77(16) . . ?
C2 C3 C19 120.92(16) . . ?
C5 C4 C3 121.40(16) . . ?
C5 C4 H2 119.3 . . ?
C3 C4 H2 119.3 . . ?
C4 C5 C6 119.31(16) . . ?
C4 C5 H3 120.3 . . ?
C6 C5 H3 120.3 . . ?
C5 C6 C1 121.37(16) . . ?
C5 C6 N1 123.92(15) . . ?
C1 C6 N1 114.69(15) . . ?
N1 N1 C6 114.64(17) 2_556 . ?
C8 C7 C12 117.58(17) . . ?
C8 C7 Si1 121.71(13) . . ?
C12 C7 Si1 120.71(14) . . ?
C9 C8 C7 121.40(17) . . ?
C9 C8 H4 119.3 . . ?
C7 C8 H4 119.3 . . ?
C10 C9 C8 119.55(18) . . ?
C10 C9 H5 120.2 . . ?
C8 C9 H5 120.2 . . ?
C9 C10 C11 120.07(18) . . ?
C9 C10 H6 120.0 . . ?
C11 C10 H6 120.0 . . ?
C12 C11 C10 120.02(18) . . ?
C12 C11 H7 120.0 . . ?
C10 C11 H7 120.0 . . ?
C11 C12 C7 121.36(17) . . ?
C11 C12 H8 119.3 . . ?
C7 C12 H8 119.3 . . ?
C14 C13 C18 117.95(16) . . ?
C14 C13 Si1 119.59(14) . . ?
C18 C13 Si1 122.41(14) . . ?
C15 C14 C13 121.18(18) . . ?
C15 C14 H9 119.4 . . ?
C13 C14 H9 119.4 . . ?
C14 C15 C16 119.97(18) . . ?
C14 C15 H10 120.0 . . ?
C16 C15 H10 120.0 . . ?
C17 C16 C15 119.67(18) . . ?
C17 C16 H11 120.2 . . ?
C15 C16 H11 120.2 . . ?
C16 C17 C18 120.59(18) . . ?
C16 C17 H12 119.7 . . ?
C18 C17 H12 119.7 . . ?
C17 C18 C13 120.61(17) . . ?
C17 C18 H13 119.7 . . ?
C13 C18 H13 119.7 . . ?
C3 C19 H14 109.5 . . ?
C3 C19 H15 109.5 . . ?
H14 C19 H15 109.5 . . ?
C3 C19 H16 109.5 . . ?
H14 C19 H16 109.5 . . ?
H15 C19 H16 109.5 . . ?
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
Si1 F1 1.6087(12) . ?
Si1 C13 1.8623(19) . ?
Si1 C7 1.8629(19) . ?
Si1 C1 1.8769(19) . ?
C1 C2 1.395(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.403(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.396(3) . ?
C3 C19 1.503(3) . ?
C4 C5 1.376(3) . ?
C4 H2 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H3 0.9500 . ?
C6 N1 1.424(2) . ?
N1 N1 1.257(3) 2_556 ?
C7 C8 1.399(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.394(3) . ?
C8 H4 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H5 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H6 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H7 0.9500 . ?
C12 H8 0.9500 . ?
C13 C14 1.394(3) . ?
C13 C18 1.406(3) . ?
C14 C15 1.388(3) . ?
C14 H9 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H10 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H11 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H12 0.9500 . ?
C18 H13 0.9500 . ?
C19 H14 0.9800 . ?
C19 H15 0.9800 . ?
C19 H16 0.9800 . ?
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
_geom_torsion_publ_flag
F1 Si1 C1 C2 -11.16(15) . . . . ?
C13 Si1 C1 C2 102.03(15) . . . . ?
C7 Si1 C1 C2 -128.20(14) . . . . ?
F1 Si1 C1 C6 172.50(13) . . . . ?
C13 Si1 C1 C6 -74.31(16) . . . . ?
C7 Si1 C1 C6 55.46(16) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
Si1 C1 C2 C3 -174.75(13) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C19 179.76(16) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C19 C3 C4 C5 178.81(16) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 N1 179.17(15) . . . . ?
C2 C1 C6 C5 -2.4(2) . . . . ?
Si1 C1 C6 C5 174.07(13) . . . . ?
C2 C1 C6 N1 179.32(14) . . . . ?
Si1 C1 C6 N1 -4.2(2) . . . . ?
C5 C6 N1 N1 14.8(3) . . . 2_556 ?
C1 C6 N1 N1 -166.98(17) . . . 2_556 ?
F1 Si1 C7 C8 -78.87(15) . . . . ?
C13 Si1 C7 C8 167.30(14) . . . . ?
C1 Si1 C7 C8 35.96(17) . . . . ?
F1 Si1 C7 C12 100.59(15) . . . . ?
C13 Si1 C7 C12 -13.23(17) . . . . ?
C1 Si1 C7 C12 -144.57(14) . . . . ?
C12 C7 C8 C9 -1.0(3) . . . . ?
Si1 C7 C8 C9 178.48(14) . . . . ?
C7 C8 C9 C10 1.5(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
Si1 C7 C12 C11 -179.63(14) . . . . ?
F1 Si1 C13 C14 2.28(16) . . . . ?
C7 Si1 C13 C14 117.98(15) . . . . ?
C1 Si1 C13 C14 -110.41(15) . . . . ?
F1 Si1 C13 C18 -175.30(13) . . . . ?
C7 Si1 C13 C18 -59.61(16) . . . . ?
C1 Si1 C13 C18 72.00(16) . . . . ?
C18 C13 C14 C15 1.6(3) . . . . ?
Si1 C13 C14 C15 -176.14(14) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
Si1 C13 C18 C17 177.18(14) . . . . ?
