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#$Date: 2025-09-11 01:11:53 +0300 (Thu, 11 Sep 2025) $
#$Revision: 302090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/56/1575663.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_1575663
loop_
_publ_author_name
'Heller, Jan'
'Buch, Christoph D.'
'Virovets, Alexander'
'Peresypkina, Eugenia V.'
'Lerner, Hans-Wolfram'
'Fantuzzi, Felipe'
'Wagner, Matthias'
_publ_section_title
;
 Synthesis of Perhalogenated Silylboranes (X = Cl, I) and Their
 Application in Regiodivergent Alkene Silaboration
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06234A
_journal_year                    2025
_chemical_formula_moiety         'C5 H5 B I5 N Si'
_chemical_formula_sum            'C5 H5 B I5 N Si'
_chemical_formula_weight         752.50
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2025-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9353(3)
_cell_length_b                   8.42736(19)
_cell_length_c                   13.3513(2)
_cell_measurement_reflns_used    10668
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.3490
_cell_measurement_theta_min      4.1670
_cell_volume                     1567.95(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_publication_material  'IUCr PublCIF online service'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16700
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         4.090
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    9.961
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.43a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(7)
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0479P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3718
_reflns_number_total             3849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc06234a3.cif
_cod_data_source_block           2_py_wa3352
_cod_original_cell_volume        1567.94(5)
_cod_database_code               1575663
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.198
_shelx_estimated_absorpt_t_max   0.317
loop_
_space_group_symop_operation_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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.5598(7) 0.3584(10) 0.3064(5) 0.0367(7) Uani 0.594 1 d . . P A 1
I2A I 0.7108(3) 0.7722(5) 0.3628(3) 0.0393(6) Uani 0.594 1 d . . P A 1
I3A I 0.8414(3) 0.3689(4) 0.4391(3) 0.0627(8) Uani 0.594 1 d . . P A 1
I4A I 0.7342(2) 0.6261(5) 0.6510(3) 0.0462(8) Uani 0.594 1 d . . P A 1
I5A I 0.46381(15) 0.6061(2) 0.50069(16) 0.0360(4) Uani 0.594 1 d . . P A 1
Si1A Si 0.7056(2) 0.5361(5) 0.4771(3) 0.0296(7) Uani 0.594 1 d . . P A 1
B1A B 0.5774(9) 0.4244(16) 0.4685(10) 0.023(2) Uani 0.594 1 d . . P A 1
N1A N 0.5749(7) 0.2804(12) 0.5437(8) 0.028(2) Uani 0.594 1 d D . P A 1
C1A C 0.5387(11) 0.296(2) 0.6359(10) 0.040(3) Uani 0.594 1 d D U P A 1
H1A H 0.507895 0.392034 0.654782 0.048 Uiso 0.594 1 calc R U P A 1
C2A C 0.5461(17) 0.174(2) 0.7034(19) 0.058(9) Uani 0.594 1 d D U P A 1
H2A H 0.518499 0.184759 0.768062 0.070 Uiso 0.594 1 calc R U P A 1
C3A C 0.5926(19) 0.036(2) 0.6792(14) 0.066(6) Uani 0.594 1 d D U P A 1
H3A H 0.596803 -0.049370 0.725761 0.080 Uiso 0.594 1 calc R U P A 1
C4A C 0.633(2) 0.024(2) 0.5858(12) 0.066(6) Uani 0.594 1 d D U P A 1
H4A H 0.669662 -0.066601 0.567875 0.079 Uiso 0.594 1 calc R U P A 1
C5A C 0.619(2) 0.145(2) 0.5188(16) 0.063(7) Uani 0.594 1 d D U P A 1
H5A H 0.642274 0.132644 0.452272 0.075 Uiso 0.594 1 calc R U P A 1
I1B I 0.5646(11) 0.3347(15) 0.3169(10) 0.0367(7) Uani 0.406 1 d . . P B 2
I2B I 0.7149(5) 0.7402(8) 0.3508(5) 0.0599(19) Uani 0.406 1 d . . P B 2
I3B I 0.8292(4) 0.3201(5) 0.4509(4) 0.0541(10) Uani 0.406 1 d . . P B 2
I4B I 0.7581(3) 0.6070(6) 0.6494(5) 0.0332(7) Uani 0.406 1 d . . P B 2
I5B I 0.4789(2) 0.6584(3) 0.5136(3) 0.0377(6) Uani 0.406 1 d . . P B 2
Si1B Si 0.6227(3) 0.5425(6) 0.4389(3) 0.0239(9) Uani 0.406 1 d . . P B 2
B1B B 0.7083(13) 0.428(2) 0.5393(15) 0.024(4) Uani 0.406 1 d . . P B 2
N1B N 0.6486(11) 0.2882(17) 0.5898(11) 0.030(3) Uani 0.406 1 d D . P B 2
C1B C 0.5906(15) 0.320(3) 0.6670(14) 0.041(5) Uani 0.406 1 d D U P B 2
H1B H 0.591693 0.424933 0.693344 0.049 Uiso 0.406 1 calc R U P B 2
C2B C 0.530(2) 0.213(3) 0.711(2) 0.040(7) Uani 0.406 1 d D U P B 2
H2B H 0.486184 0.244036 0.762266 0.048 Uiso 0.406 1 calc R U P B 2
C3B C 0.533(2) 0.058(3) 0.6785(19) 0.058(7) Uani 0.406 1 d D U P B 2
H3B H 0.503418 -0.024598 0.715186 0.070 Uiso 0.406 1 calc R U P B 2
C4B C 0.5821(17) 0.028(3) 0.5914(19) 0.049(7) Uani 0.406 1 d D U P B 2
H4B H 0.572812 -0.069857 0.557150 0.059 Uiso 0.406 1 calc R U P B 2
C5B C 0.644(2) 0.140(2) 0.554(3) 0.057(9) Uani 0.406 1 d D U P B 2
H5B H 0.685965 0.110445 0.500861 0.068 Uiso 0.406 1 calc R U P B 2
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'
B B 0.0013 0.0007 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
B1A Si1A I3A 114.2(4) . . ?
B1A Si1A I4A 109.7(4) . . ?
I3A Si1A I4A 104.52(18) . . ?
B1A Si1A I2A 111.1(4) . . ?
I3A Si1A I2A 108.22(18) . . ?
I4A Si1A I2A 108.8(2) . . ?
N1A B1A Si1A 110.0(7) . . ?
N1A B1A I5A 112.9(8) . . ?
Si1A B1A I5A 107.1(6) . . ?
N1A B1A I1A 114.9(8) . . ?
Si1A B1A I1A 105.4(6) . . ?
I5A B1A I1A 106.0(5) . . ?
C1A N1A C5A 119.1(14) . . ?
C1A N1A B1A 121.3(11) . . ?
C5A N1A B1A 119.2(12) . . ?
N1A C1A C2A 120.1(18) . . ?
N1A C1A H1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
C3A C2A C1A 121(2) . . ?
C3A C2A H2A 119.4 . . ?
C1A C2A H2A 119.4 . . ?
C2A C3A C4A 118.0(19) . . ?
C2A C3A H3A 121.0 . . ?
C4A C3A H3A 121.0 . . ?
C5A C4A C3A 118.9(18) . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A H4A 120.5 . . ?
N1A C5A C4A 122.4(17) . . ?
N1A C5A H5A 118.8 . . ?
C4A C5A H5A 118.8 . . ?
B1B Si1B I2B 109.6(6) . . ?
B1B Si1B I5B 113.7(6) . . ?
I2B Si1B I5B 111.1(3) . . ?
B1B Si1B I1B 106.5(6) . . ?
I2B Si1B I1B 109.6(4) . . ?
I5B Si1B I1B 106.1(4) . . ?
N1B B1B Si1B 108.9(11) . . ?
N1B B1B I4B 112.7(12) . . ?
Si1B B1B I4B 107.4(9) . . ?
N1B B1B I3B 108.2(11) . . ?
Si1B B1B I3B 106.6(9) . . ?
I4B B1B I3B 112.8(8) . . ?
C1B N1B C5B 116(2) . . ?
C1B N1B B1B 119.5(15) . . ?
C5B N1B B1B 124.4(18) . . ?
N1B C1B C2B 125(2) . . ?
N1B C1B H1B 117.6 . . ?
C2B C1B H1B 117.6 . . ?
C3B C2B C1B 118(3) . . ?
C3B C2B H2B 121.1 . . ?
C1B C2B H2B 121.1 . . ?
C4B C3B C2B 118(3) . . ?
C4B C3B H3B 121.1 . . ?
C2B C3B H3B 121.1 . . ?
C3B C4B C5B 119(3) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
N1B C5B C4B 123(2) . . ?
N1B C5B H5B 118.7 . . ?
C4B C5B H5B 118.7 . . ?
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
I1A B1A 2.249(16) . ?
I2A Si1A 2.509(5) . ?
I3A Si1A 2.413(5) . ?
I4A Si1A 2.474(6) . ?
I5A B1A 2.243(13) . ?
Si1A B1A 2.024(13) . ?
B1A N1A 1.575(17) . ?
N1A C1A 1.336(12) . ?
N1A C5A 1.339(10) . ?
C1A C2A 1.375(10) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.369(13) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.371(12) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.371(12) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
I1B Si1B 2.526(16) . ?
I2B Si1B 2.410(8) . ?
I3B B1B 2.25(2) . ?
I4B B1B 2.22(2) . ?
I5B Si1B 2.442(6) . ?
Si1B B1B 2.04(2) . ?
B1B N1B 1.59(2) . ?
N1B C1B 1.337(13) . ?
N1B C5B 1.342(13) . ?
C1B C2B 1.376(13) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.372(13) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.370(13) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.375(13) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1A^a H1A^a I1A^a 0.95 3.07 3.943(17) 153.9 2_665 yes
C1A^a H1A^a I5A^a 0.95 2.80 3.343(16) 116.9 . yes
C4A^a H4A^a I2A^a 0.95 3.11 3.814(18) 132.3 1_545 yes
C4A^a H4A^a I4A^a 0.95 2.96 3.740(17) 140.6 1_545 yes
C5A^a H5A^a I1A^a 0.95 2.96 3.46(2) 114.5 . yes
C1B^b H1B^b I4B^b 0.95 2.84 3.37(2) 115.9 . yes
C2B^b H2B^b I2B^b 0.95 3.04 3.90(3) 151.3 2_665 yes
C4B^b H4B^b I5B^b 0.95 2.70 3.58(3) 154.6 1_545 yes
C5B^b H5B^b I3B^b 0.95 2.75 3.29(3) 117.3 . yes
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
Si1A B1A N1A C1A 94.1(12) . . . . ?
I5A B1A N1A C1A -25.5(13) . . . . ?
I1A B1A N1A C1A -147.2(10) . . . . ?
Si1A B1A N1A C5A -78.4(18) . . . . ?
I5A B1A N1A C5A 162.0(16) . . . . ?
I1A B1A N1A C5A 40.3(18) . . . . ?
C5A N1A C1A C2A -1(2) . . . . ?
B1A N1A C1A C2A -173.4(14) . . . . ?
N1A C1A C2A C3A 2(3) . . . . ?
C1A C2A C3A C4A 1(4) . . . . ?
C2A C3A C4A C5A -5(4) . . . . ?
C1A N1A C5A C4A -3(4) . . . . ?
B1A N1A C5A C4A 170(2) . . . . ?
C3A C4A C5A N1A 6(4) . . . . ?
Si1B B1B N1B C1B -82.9(17) . . . . ?
I4B B1B N1B C1B 36.1(19) . . . . ?
I3B B1B N1B C1B 161.6(13) . . . . ?
Si1B B1B N1B C5B 90(2) . . . . ?
I4B B1B N1B C5B -151(2) . . . . ?
I3B B1B N1B C5B -26(3) . . . . ?
C5B N1B C1B C2B 1(3) . . . . ?
B1B N1B C1B C2B 174.1(18) . . . . ?
N1B C1B C2B C3B 5(3) . . . . ?
C1B C2B C3B C4B -13(4) . . . . ?
C2B C3B C4B C5B 16(4) . . . . ?
C1B N1B C5B C4B 2(4) . . . . ?
B1B N1B C5B C4B -171(3) . . . . ?
C3B C4B C5B N1B -11(5) . . . . ?
