#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/81/7108193.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_7108193
loop_
_publ_author_name
'Yuichiro Tokoro'
'Hyeonuk Yeo'
'Kazuo Tanaka'
'Yoshiki Chujo'
_publ_section_title
;
 Synthesis of benzo[h]quinoline-based neutral pentacoordinate
 organosilicon complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8541
_journal_paper_doi               10.1039/c2cc34440h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C13 H8 F3 N Si'
_chemical_formula_weight         263.29
_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                 97.739(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1120(13)
_cell_length_b                   14.615(3)
_cell_length_c                   9.2149(14)
_cell_measurement_temperature    93(2)
_cell_volume                     1082.5(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8029
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0359
_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)+(0.0485P)²+0.4403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                1615
_reflns_number_total             1894
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2cc34440h.txt
_cod_data_source_block           2
_cod_original_sg_symbol_Hall     -p_2yn
_cod_original_sg_symbol_H-M      p_21/n
_cod_database_code               7108193
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_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
Si1 Si 0.14419(7) 0.21768(3) 0.45284(6) 0.02440(19) Uani 1 1 d
F1 F 0.01707(14) 0.23137(8) 0.30570(12) 0.0327(3) Uani 1 1 d
F2 F 0.31481(15) 0.27132(7) 0.44525(13) 0.0330(3) Uani 1 1 d
F3 F 0.06097(16) 0.29855(8) 0.54165(13) 0.0378(3) Uani 1 1 d
N1 N 0.24338(19) 0.11398(10) 0.34135(16) 0.0226(4) Uani 1 1 d
C1 C 0.2941(2) 0.11572(14) 0.2097(2) 0.0270(4) Uani 1 1 d
C2 C 0.3669(3) 0.03922(14) 0.1540(2) 0.0292(5) Uani 1 1 d
C3 C 0.3901(3) -0.03990(14) 0.2350(2) 0.0293(5) Uani 1 1 d
C4 C 0.3369(2) -0.04349(13) 0.3741(2) 0.0257(4) Uani 1 1 d
C5 C 0.3512(3) -0.12067(14) 0.4724(2) 0.0295(5) Uani 1 1 d
C6 C 0.2933(3) -0.11692(14) 0.6034(2) 0.0290(5) Uani 1 1 d
C7 C 0.2156(2) -0.03558(13) 0.6517(2) 0.0254(4) Uani 1 1 d
C8 C 0.1519(3) -0.02587(14) 0.7859(2) 0.0298(5) Uani 1 1 d
C9 C 0.0815(3) 0.05518(15) 0.8206(2) 0.0308(5) Uani 1 1 d
C10 C 0.0721(3) 0.13127(14) 0.7261(2) 0.0275(5) Uani 1 1 d
C11 C 0.1338(2) 0.12534(13) 0.5933(2) 0.0238(4) Uani 1 1 d
C12 C 0.2031(2) 0.04130(13) 0.5592(2) 0.0228(4) Uani 1 1 d
C13 C 0.2635(2) 0.03586(12) 0.4210(2) 0.0222(4) Uani 1 1 d
H8 H 0.027(3) 0.1862(15) 0.752(2) 0.027(5) Uiso 1 1 d
H4 H 0.400(3) -0.1719(15) 0.445(2) 0.028(5) Uiso 1 1 d
H7 H 0.039(3) 0.0645(15) 0.911(2) 0.036(6) Uiso 1 1 d
H1 H 0.274(2) 0.1712(14) 0.156(2) 0.020(5) Uiso 1 1 d
H2 H 0.401(3) 0.0456(15) 0.062(2) 0.039(6) Uiso 1 1 d
H6 H 0.159(3) -0.0731(15) 0.853(2) 0.035(6) Uiso 1 1 d
H3 H 0.441(3) -0.0898(16) 0.200(2) 0.032(6) Uiso 1 1 d
H5 H 0.308(3) -0.1668(16) 0.666(2) 0.038(6) Uiso 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'
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
F2 Si1 F1 111.33(7)
F2 Si1 F3 94.91(7)
F1 Si1 F3 94.09(7)
F2 Si1 C11 120.07(8)
F1 Si1 C11 126.10(8)
F3 Si1 C11 96.56(7)
F2 Si1 N1 86.58(6)
F1 Si1 N1 85.40(6)
F3 Si1 N1 178.52(7)
C11 Si1 N1 82.64(7)
C1 N1 C13 118.65(16)
C1 N1 Si1 129.11(13)
C13 N1 Si1 112.17(12)
N1 C1 C2 121.17(18)
C3 C2 C1 120.59(18)
C2 C3 C4 119.26(18)
C13 C4 C3 116.48(18)
C13 C4 C5 117.17(18)
C3 C4 C5 126.35(18)
C6 C5 C4 121.36(19)
C5 C6 C7 121.75(19)
C12 C7 C8 116.48(18)
C12 C7 C6 118.07(18)
C8 C7 C6 125.45(18)
C9 C8 C7 120.33(19)
C8 C9 C10 121.82(19)
C11 C10 C9 120.05(19)
C10 C11 C12 117.12(17)
C10 C11 Si1 128.19(15)
C12 C11 Si1 114.65(13)
C11 C12 C7 124.20(17)
C11 C12 C13 116.41(16)
C7 C12 C13 119.40(17)
N1 C13 C4 123.84(17)
N1 C13 C12 113.92(16)
C4 C13 C12 122.24(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 F2 1.6004(13)
Si1 F1 1.6016(13)
Si1 F3 1.6343(12)
Si1 C11 1.8799(19)
Si1 N1 2.0548(16)
N1 C1 1.333(2)
N1 C13 1.355(2)
C1 C2 1.394(3)
C2 C3 1.375(3)
C3 C4 1.408(3)
C4 C13 1.398(3)
C4 C5 1.441(3)
C5 C6 1.354(3)
C6 C7 1.443(3)
C7 C12 1.406(3)
C7 C8 1.411(3)
C8 C9 1.371(3)
C9 C10 1.409(3)
C10 C11 1.385(3)
C11 C12 1.404(3)
C12 C13 1.427(3)
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
F2 Si1 N1 C1 -60.08(17)
F1 Si1 N1 C1 51.66(17)
F3 Si1 N1 C1 121(3)
C11 Si1 N1 C1 178.99(18)
F2 Si1 N1 C13 116.83(13)
F1 Si1 N1 C13 -131.43(13)
F3 Si1 N1 C13 -62(3)
C11 Si1 N1 C13 -4.09(13)
C13 N1 C1 C2 -0.1(3)
Si1 N1 C1 C2 176.60(14)
N1 C1 C2 C3 -0.9(3)
C1 C2 C3 C4 1.1(3)
C2 C3 C4 C13 -0.4(3)
C2 C3 C4 C5 179.8(2)
C13 C4 C5 C6 1.1(3)
C3 C4 C5 C6 -179.0(2)
C4 C5 C6 C7 -0.4(3)
C5 C6 C7 C12 -0.8(3)
C5 C6 C7 C8 179.88(19)
C12 C7 C8 C9 0.2(3)
C6 C7 C8 C9 179.5(2)
C7 C8 C9 C10 -0.8(3)
C8 C9 C10 C11 0.4(3)
C9 C10 C11 C12 0.5(3)
C9 C10 C11 Si1 -177.16(16)
F2 Si1 C11 C10 99.79(19)
F1 Si1 C11 C10 -99.72(19)
F3 Si1 C11 C10 0.23(19)
N1 Si1 C11 C10 -178.51(19)
F2 Si1 C11 C12 -77.90(16)
F1 Si1 C11 C12 82.59(16)
F3 Si1 C11 C12 -177.46(14)
N1 Si1 C11 C12 3.80(14)
C10 C11 C12 C7 -1.1(3)
Si1 C11 C12 C7 176.89(15)
C10 C11 C12 C13 178.97(17)
Si1 C11 C12 C13 -3.1(2)
C8 C7 C12 C11 0.7(3)
C6 C7 C12 C11 -178.64(17)
C8 C7 C12 C13 -179.32(17)
C6 C7 C12 C13 1.3(3)
C1 N1 C13 C4 0.9(3)
Si1 N1 C13 C4 -176.35(15)
C1 N1 C13 C12 -179.27(17)
Si1 N1 C13 C12 3.5(2)
C3 C4 C13 N1 -0.7(3)
C5 C4 C13 N1 179.22(17)
C3 C4 C13 C12 179.55(17)
C5 C4 C13 C12 -0.6(3)
C11 C12 C13 N1 -0.5(2)
C7 C12 C13 N1 179.55(17)
C11 C12 C13 C4 179.32(17)
C7 C12 C13 C4 -0.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182703
