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#$Date: 2024-05-18 04:09:45 +0300 (Sat, 18 May 2024) $
#$Revision: 291948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/86/7248642.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_7248642
loop_
_publ_author_name
'Pacholak, P.'
'Durka, K.'
'Woźniak, K.'
'Krajewska, J.'
'Laudy, A. E.'
'Luliński, S.'
_publ_section_title
;
 Ethynyl-substituted benzosiloxaboroles: the role of C(π)⋯B
 interactions in their crystal packing and use in Cu(i)-catalyzed
 1,3-dipolar cycloaddition
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              16069
_journal_page_last               16082
_journal_paper_doi               10.1039/D4RA02137A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C10 H10 B F O2 Si, C2 H3 N'
_chemical_formula_sum            'C12 H13 B F N O2 Si'
_chemical_formula_weight         261.13
_chemical_name_systematic
;
6-Ethynyl-7-fluoro-1,1-dimethylbenzo[c][1,2,5]oxasilaborol-3(1H)-ol MeCN monosolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.153(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6127(2)
_cell_length_b                   7.0177(2)
_cell_length_c                   11.1617(3)
_cell_measurement_reflns_used    7108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.3800
_cell_measurement_theta_min      2.3850
_cell_volume                     669.38(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14332
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.833
_diffrn_reflns_theta_min         2.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0335
_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)+(0.0481P)²+0.1473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2374
_reflns_number_total             2733
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02137a2.cif
_cod_data_source_block           1c_MeCN
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7248642
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.845
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_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
Si1 Si 0.20027(4) 0.2500 0.70191(3) 0.01311(9) Uani 1 2 d S T P . .
F1 F 0.24624(9) 0.2500 0.40784(7) 0.01870(16) Uani 1 2 d S T P . .
O2 O 0.31294(10) 0.2500 0.83497(8) 0.01771(18) Uani 1 2 d S T P . .
O1 O 0.57324(11) 0.2500 0.92786(8) 0.0222(2) Uani 1 2 d DS T P . .
C8 C 0.53078(14) 0.2500 0.31252(10) 0.0149(2) Uani 1 2 d S T P . .
C3 C 0.37946(13) 0.2500 0.48699(10) 0.01289(19) Uani 1 2 d S T P . .
C1 C 0.50759(13) 0.2500 0.69058(10) 0.01286(19) Uani 1 2 d S T P . .
C5 C 0.65964(14) 0.2500 0.52285(10) 0.0149(2) Uani 1 2 d S T P . .
H5 H 0.7587 0.2500 0.4937 0.018 Uiso 1 2 calc R U P . .
C4 C 0.52231(13) 0.2500 0.44007(10) 0.0128(2) Uani 1 2 d S T P . .
C2 C 0.36773(13) 0.2500 0.60938(10) 0.01265(19) Uani 1 2 d S T P . .
B1 B 0.47093(16) 0.2500 0.82542(12) 0.0155(2) Uani 1 2 d S T P . .
C9 C 0.54425(15) 0.2500 0.20698(11) 0.0189(2) Uani 1 2 d S T P . .
H9 H 0.5549 0.2500 0.1233 0.023 Uiso 1 2 calc R U P . .
C6 C 0.65257(14) 0.2500 0.64647(10) 0.0150(2) Uani 1 2 d S T P . .
H6 H 0.7464 0.2500 0.7011 0.018 Uiso 1 2 calc R U P . .
C7 C 0.07800(11) 0.03234(13) 0.68827(9) 0.02049(17) Uani 1 1 d . . . . .
H7A H 0.1455 -0.0804 0.6989 0.031 Uiso 1 1 calc R U . . .
H7B H 0.0166 0.0287 0.6082 0.031 Uiso 1 1 calc R U . . .
H7C H 0.0071 0.0335 0.7505 0.031 Uiso 1 1 calc R U . . .
H1 H 0.6697(12) 0.2500 0.9218(18) 0.031 Uiso 1 2 d DS U P . .
N1 N 0.90706(15) 0.2500 0.95509(12) 0.0275(3) Uani 1 2 d S T P . .
C11 C 1.17786(16) 0.2500 1.08832(13) 0.0230(3) Uani 1 2 d S T P . .
C10 C 1.02588(16) 0.2500 1.01424(12) 0.0213(2) Uani 1 2 d S T P . .
H11B H 1.2329(14) 0.145(2) 1.0669(12) 0.032 Uiso 1 1 d . U . . .
H11A H 1.164(2) 0.2500 1.1768(18) 0.032 Uiso 1 2 d S U P . .
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'
O O 0.0106 0.0060 '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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 5 0.0543
-2 5 1 0.0836
-5 1 0 0.0799
-5 -1 0 0.0821
2 -5 -1 0.0968
0 -1 -5 0.0199
5 1 0 0.1122
-1 0 0 0.0749
0 -1 5 0.0281
1 5 -2 0.0907
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
O2 Si1 C7 109.56(4) . . ?
O2 Si1 C7 109.56(4) . 4_565 ?
C7 Si1 C7 111.24(6) . 4_565 ?
O2 Si1 C2 95.06(5) . . ?
C7 Si1 C2 115.05(3) . . ?
C7 Si1 C2 115.05(3) 4_565 . ?
B1 O2 Si1 113.66(8) . . ?
B1 O1 H1 118.5(14) . . ?
C9 C8 C4 177.37(13) . . ?
F1 C3 C2 118.88(10) . . ?
F1 C3 C4 117.95(10) . . ?
C2 C3 C4 123.17(10) . . ?
C6 C1 C2 120.07(10) . . ?
C6 C1 B1 129.07(10) . . ?
C2 C1 B1 110.86(10) . . ?
C6 C5 C4 121.00(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 117.49(10) . . ?
C3 C4 C8 121.90(10) . . ?
C5 C4 C8 120.61(10) . . ?
C3 C2 C1 118.17(10) . . ?
C3 C2 Si1 134.43(9) . . ?
C1 C2 Si1 107.40(8) . . ?
O1 B1 O2 118.67(11) . . ?
O1 B1 C1 128.31(11) . . ?
O2 B1 C1 113.02(10) . . ?
C8 C9 H9 180.0 . . ?
C5 C6 C1 120.10(10) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C11 H11B 107.8(8) . . ?
C10 C11 H11A 110.1(12) . . ?
H11B C11 H11A 112.4(10) . . ?
N1 C10 C11 179.39(15) . . ?
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 O2 1.6699(9) . ?
Si1 C7 1.8508(9) . ?
Si1 C7 1.8508(9) 4_565 ?
Si1 C2 1.8756(12) . ?
F1 C3 1.3582(13) . ?
O2 B1 1.3781(16) . ?
O1 B1 1.3539(16) . ?
O1 H1 0.842(9) . ?
C8 C9 1.1980(17) . ?
C8 C4 1.4345(16) . ?
C3 C2 1.3823(16) . ?
C3 C4 1.3959(16) . ?
C1 C6 1.3981(16) . ?
C1 C2 1.4144(15) . ?
C1 B1 1.5759(17) . ?
C5 C6 1.3887(16) . ?
C5 C4 1.4073(15) . ?
C5 H5 0.9500 . ?
C9 H9 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C10 1.1467(18) . ?
C11 C10 1.4587(18) . ?
C11 H11B 0.925(14) . ?
C11 H11A 1.01(2) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 0.9976 5.0010 -0.1162 -0.3084 0.0646
-2.0003 5.0015 1.0066 -0.5329 -0.0140 -0.0183
-5.0034 1.0029 0.0022 -0.2068 0.0198 -0.3734
-5.0040 -0.9975 -0.0003 -0.0127 0.0017 -0.4272
2.0003 -5.0015 -1.0066 0.5329 0.0140 0.0183
0.0006 -0.9976 -5.0010 0.1162 0.3084 -0.0646
5.0040 0.9975 0.0003 0.0127 -0.0017 0.4272
-1.0007 0.0005 0.0002 -0.0220 0.0022 -0.0801
-0.0011 -1.0027 4.9985 0.0779 -0.3265 0.0109
1.0024 5.0014 -1.9938 -0.4556 0.1700 0.1992
