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#$Date: 2024-01-06 10:04:15 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247541.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_7247541
loop_
_publ_author_name
'Durka, Krzysztof'
'Zuba, Adam'
'Marek-Urban, Paulina H.'
'Nowicki, Krzysztof'
'Drapała, Jakub'
'Woźniak, Krzysztof'
'Luliński, Sergiusz'
_publ_section_title
;
 Exploring the effect of substitution patterns on the symmetry of
 hydrogen-bonded supramolecular motifs in functionalized
 benzosiloxaboroles
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              6329
_journal_page_last               6342
_journal_paper_doi               10.1039/D3CE00880K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C10 H12 B F O4 Si'
_chemical_formula_sum            'C10 H12 B F O4 Si'
_chemical_formula_weight         254.10
_chemical_name_systematic
;
methyl 7-fluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborole-4-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-10-01 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.928(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3215(13)
_cell_length_b                   6.9213(5)
_cell_length_c                   13.3412(15)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2440
_cell_measurement_theta_min      4.1260
_cell_volume                     1182.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.849
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3500
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.619
_diffrn_reflns_theta_min         4.154
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.905
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0902P)²+0.3281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1620
_reflns_number_total             2026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00880k2.cif
_cod_data_source_block           4-CO2Me-7-F
_cod_depositor_comments
'Adding full bibliography for 7247541--7247563.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247541
_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 0.753
_oxdiff_exptl_absorpt_empirical_full_max 1.308
_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+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_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 0.05318(6) 0.15406(10) 0.81802(6) 0.0222(2) Uani 1 1 d . . . . .
F1 F -0.17454(12) 0.2174(2) 0.65074(14) 0.0294(4) Uani 1 1 d . . . . .
O4 O 0.12975(15) 0.2966(3) 0.37465(17) 0.0275(5) Uani 1 1 d . . . . .
O2 O 0.17843(14) 0.1410(3) 0.82022(17) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.0749(2) 0.2377(3) 0.5255(2) 0.0218(6) Uani 1 1 d . . . . .
O1 O 0.29644(16) 0.1537(3) 0.71969(19) 0.0347(5) Uani 1 1 d D . . . .
C4 C -0.1115(2) 0.2572(4) 0.5043(2) 0.0234(6) Uani 1 1 d . . . . .
H4 H -0.1810 0.2743 0.4619 0.028 Uiso 1 1 calc R U . . .
O3 O 0.25322(15) 0.2135(3) 0.51701(19) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.2102(2) 0.3093(4) 0.3220(3) 0.0330(7) Uani 1 1 d . . . . .
H10A H 0.1792 0.3465 0.2491 0.049 Uiso 1 1 calc R U . . .
H10B H 0.2446 0.1836 0.3245 0.049 Uiso 1 1 calc R U . . .
H10C H 0.2617 0.4065 0.3563 0.049 Uiso 1 1 calc R U . . .
C5 C -0.0920(2) 0.2250(3) 0.6079(2) 0.0226(6) Uani 1 1 d . . . . .
C3 C -0.0274(2) 0.2648(3) 0.4614(2) 0.0210(6) Uani 1 1 d . . . . .
H3 H -0.0390 0.2882 0.3890 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1618(2) 0.2465(4) 0.4749(2) 0.0234(6) Uani 1 1 d . . . . .
C6 C 0.0069(2) 0.1985(3) 0.6750(2) 0.0210(6) Uani 1 1 d . . . . .
C1 C 0.0930(2) 0.2040(3) 0.6323(2) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.0313(3) 0.3565(4) 0.9001(3) 0.0322(7) Uani 1 1 d . . . . .
H8A H 0.0567 0.4768 0.8771 0.048 Uiso 1 1 calc R U . . .
H8B H 0.0691 0.3316 0.9731 0.048 Uiso 1 1 calc R U . . .
H8C H -0.0435 0.3682 0.8938 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0090(2) -0.0782(4) 0.8596(2) 0.0263(6) Uani 1 1 d . . . . .
H7A H 0.0221 -0.1823 0.8150 0.040 Uiso 1 1 calc R U . . .
H7B H -0.0659 -0.0712 0.8536 0.040 Uiso 1 1 calc R U . . .
H7C H 0.0474 -0.1042 0.9322 0.040 Uiso 1 1 calc R U . . .
B1 B 0.1976(2) 0.1661(4) 0.7253(3) 0.0253(7) Uani 1 1 d . . . . .
H1A H 0.298(3) 0.180(5) 0.6592(13) 0.038 Uiso 1 1 d D U . . .
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 '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
1 -4 -1 0.1579
-1 2 0 0.1126
4 0 5 0.1245
-4 0 -5 0.1444
5 0 -4 0.0239
-5 -1 4 0.0480
-5 1 4 0.0323
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 110.35(11) . . ?
O2 Si1 C8 110.55(13) . . ?
C7 Si1 C8 111.47(14) . . ?
O2 Si1 C6 94.32(12) . . ?
C7 Si1 C6 114.06(12) . . ?
C8 Si1 C6 114.83(13) . . ?
C9 O4 C10 115.5(2) . . ?
B1 O2 Si1 114.66(19) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 C9 122.0(2) . . ?
C3 C2 C9 117.5(3) . . ?
B1 O1 H1A 109(3) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 F1 118.7(2) . . ?
C4 C5 C6 124.3(3) . . ?
F1 C5 C6 117.0(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O3 C9 O4 121.1(3) . . ?
O3 C9 C2 125.9(3) . . ?
O4 C9 C2 112.9(2) . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 Si1 132.2(2) . . ?
C1 C6 Si1 109.86(19) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 B1 133.0(3) . . ?
C6 C1 B1 108.1(3) . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 . . ?
O1 B1 O2 118.6(3) . . ?
O1 B1 C1 128.4(3) . . ?
O2 B1 C1 113.0(2) . . ?
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 1.663(2) . ?
Si1 C7 1.849(3) . ?
Si1 C8 1.850(3) . ?
Si1 C6 1.863(3) . ?
F1 C5 1.372(3) . ?
O4 C9 1.334(4) . ?
O4 C10 1.437(3) . ?
O2 B1 1.369(4) . ?
C2 C1 1.398(4) . ?
C2 C3 1.409(4) . ?
C2 C9 1.492(4) . ?
O1 B1 1.342(4) . ?
O1 H1A 0.835(10) . ?
C4 C5 1.352(4) . ?
C4 C3 1.393(4) . ?
C4 H4 0.9500 . ?
O3 C9 1.215(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 C6 1.387(4) . ?
C3 H3 0.9500 . ?
C6 C1 1.415(4) . ?
C1 B1 1.612(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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
0.9762 -3.9901 -0.9923 0.1449 0.0164 0.8888
-0.9757 1.9951 -0.0123 -0.1665 -0.0005 -0.4290
3.8883 -0.0009 5.0727 0.8504 0.0008 -0.1523
-3.8883 0.0009 -5.0727 -0.8504 -0.0008 0.1523
4.9912 0.0056 -3.9574 0.0552 -0.6435 0.1063
-4.9973 -1.0034 3.9574 -0.0168 0.6830 0.1091
-4.9850 0.9923 3.9573 -0.0936 0.6041 -0.3217
