#------------------------------------------------------------------------------
#$Date: 2022-08-17 03:06:57 +0200 (Wed 17 de Aug de 2022) $
#$Revision: 277274 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/53/7245334.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_7245334
loop_
_publ_author_name
'Krajewska, Joanna'
'Nowicki, Krzysztof'
'Durka, Krzysztof'
'Marek-Urban, Paulina H.'
'Wińska, Patrycja'
'Stępniewski, Tomasz'
'Woźniak, Krzysztof'
'Laudy, Agnieszka E.'
'Luliński, Sergiusz'
_publ_section_title
;
 Oxazoline scaffold in synthesis of benzosiloxaboroles and related
 ring-expanded heterocycles: diverse reactivity, structural peculiarities
 and antimicrobial activity
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              23099
_journal_page_last               23117
_journal_paper_doi               10.1039/D2RA03910A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C13 H17 B F N O3 Si'
_chemical_formula_sum            'C13 H17 B F N O3 Si'
_chemical_formula_weight         293.17
_chemical_melting_point          405
_chemical_name_systematic
;
6-(4,4-dimethyl-2-oxazolin-2-yl)-7-fluoro-1,1-dimethyl-3-hydroxybenzo[1,2,3]siloxaborole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-04-13 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7672(3)
_cell_length_b                   12.4444(4)
_cell_length_c                   12.5674(3)
_cell_measurement_reflns_used    5273
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4580
_cell_measurement_theta_min      4.9800
_cell_volume                     1527.53(8)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0184
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8470
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.654
_diffrn_reflns_theta_min         5.001
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.851
_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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.018(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0252
_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)+(0.0405P)²+0.2784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                3003
_reflns_number_total             3081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra03910a7.cif
_cod_data_source_block           3a
_cod_database_code               7245334
_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 0.748
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.78900(5) 0.71650(4) 0.58502(4) 0.02035(12) Uani 1 1 d . . . . .
F1 F 0.49757(12) 0.75476(9) 0.71664(9) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.94714(14) 0.43348(11) 0.61375(10) 0.0238(3) Uani 1 1 d D . . . .
O2 O 0.90176(13) 0.61710(11) 0.56491(10) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.26861(13) 0.65722(12) 0.80450(10) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.35641(16) 0.59908(13) 0.96011(12) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.37225(18) 0.61283(15) 0.86037(14) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.67644(18) 0.63552(14) 0.67561(14) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.56242(19) 0.48617(14) 0.81623(14) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.5255 0.4364 0.8658 0.025 Uiso 1 1 calc R U . . .
C2 C 0.55674(18) 0.65653(14) 0.72909(13) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.49711(18) 0.58475(15) 0.79999(13) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.8690(2) 0.83238(17) 0.65381(17) 0.0305(4) Uani 1 1 d . . . . .
H8A H 0.9096 0.8082 0.7210 0.046 Uiso 1 1 calc R U . . .
H8B H 0.7992 0.8870 0.6684 0.046 Uiso 1 1 calc R U . . .
H8C H 0.9406 0.8632 0.6084 0.046 Uiso 1 1 calc R U . . .
C6 C 0.73908(18) 0.53442(15) 0.69056(14) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.68084(19) 0.46030(15) 0.76046(14) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.7223 0.3919 0.7700 0.026 Uiso 1 1 calc R U . . .
C10 C 0.15531(19) 0.66486(18) 0.87914(15) 0.0261(4) Uani 1 1 d . . . . .
H10A H 0.0868 0.6078 0.8657 0.031 Uiso 1 1 calc R U . . .
H10B H 0.1098 0.7358 0.8740 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2233(2) 0.65013(16) 0.98892(14) 0.0239(4) Uani 1 1 d . . . . .
C7 C 0.7109(2) 0.75840(18) 0.45830(15) 0.0307(4) Uani 1 1 d . . . . .
H7A H 0.6679 0.6962 0.4241 0.046 Uiso 1 1 calc R U . . .
H7B H 0.7818 0.7878 0.4114 0.046 Uiso 1 1 calc R U . . .
H7C H 0.6414 0.8135 0.4720 0.046 Uiso 1 1 calc R U . . .
B1 B 0.8726(2) 0.52385(17) 0.62015(16) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.1426(2) 0.5787(2) 1.06403(17) 0.0352(5) Uani 1 1 d . . . . .
H12A H 0.1937 0.5696 1.1305 0.053 Uiso 1 1 calc R U . . .
H12B H 0.1282 0.5083 1.0308 0.053 Uiso 1 1 calc R U . . .
H12C H 0.0538 0.6119 1.0792 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2562(2) 0.75864(18) 1.03968(16) 0.0323(5) Uani 1 1 d . . . . .
H13A H 0.3036 0.7471 1.1074 0.048 Uiso 1 1 calc R U . . .
H13B H 0.1709 0.7982 1.0524 0.048 Uiso 1 1 calc R U . . .
H13C H 0.3150 0.8002 0.9918 0.048 Uiso 1 1 calc R U . . .
H1 H 1.011(2) 0.432(2) 0.5648(18) 0.048 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'
N N 0.0311 0.0180 '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'
B B 0.0090 0.0039 '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 -1 2 0.0475
-3 5 -5 0.0962
-1 5 3 0.0695
1 -5 -3 0.0232
-2 -1 5 0.0584
-3 -4 -5 0.0696
5 4 -2 0.0295
-5 -1 -3 0.0800
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 110.55(8) . . ?
O2 Si1 C8 111.56(9) . . ?
C7 Si1 C8 110.96(10) . . ?
O2 Si1 C1 94.60(7) . . ?
C7 Si1 C1 115.73(9) . . ?
C8 Si1 C1 112.45(9) . . ?
B1 O1 H1 116(2) . . ?
B1 O2 Si1 114.14(12) . . ?
C9 O3 C10 105.18(13) . . ?
C9 N1 C11 106.70(15) . . ?
N1 C9 O3 118.38(16) . . ?
N1 C9 C3 124.98(17) . . ?
O3 C9 C3 116.63(15) . . ?
C2 C1 C6 118.26(17) . . ?
C2 C1 Si1 133.89(14) . . ?
C6 C1 Si1 107.79(13) . . ?
C5 C4 C3 120.63(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
F1 C2 C1 118.43(16) . . ?
F1 C2 C3 118.23(16) . . ?
C1 C2 C3 123.24(17) . . ?
C2 C3 C4 117.81(17) . . ?
C2 C3 C9 121.53(16) . . ?
C4 C3 C9 120.60(16) . . ?
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 . . ?
C5 C6 C1 119.76(17) . . ?
C5 C6 B1 129.32(17) . . ?
C1 C6 B1 110.93(16) . . ?
C4 C5 C6 120.24(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O3 C10 C11 104.01(14) . . ?
O3 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
O3 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N1 C11 C12 110.73(16) . . ?
N1 C11 C13 107.12(15) . . ?
C12 C11 C13 111.56(17) . . ?
N1 C11 C10 102.04(14) . . ?
C12 C11 C10 113.75(17) . . ?
C13 C11 C10 111.05(16) . . ?
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 124.19(18) . . ?
O1 B1 C6 123.40(17) . . ?
O2 B1 C6 112.40(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 O2 1.6754(13) . ?
Si1 C7 1.841(2) . ?
Si1 C8 1.854(2) . ?
Si1 C1 1.8764(18) . ?
F1 C2 1.361(2) . ?
O1 B1 1.342(3) . ?
O1 H1 0.874(13) . ?
O2 B1 1.382(2) . ?
O3 C9 1.350(2) . ?
O3 C10 1.454(2) . ?
N1 C9 1.274(2) . ?
N1 C11 1.492(2) . ?
C9 C3 1.478(2) . ?
C1 C2 1.374(3) . ?
C1 C6 1.412(3) . ?
C4 C5 1.390(3) . ?
C4 C3 1.398(2) . ?
C4 H4 0.9500 . ?
C2 C3 1.390(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 C5 1.395(3) . ?
C6 B1 1.582(3) . ?
C5 H5 0.9500 . ?
C10 C11 1.542(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(3) . ?
C11 C13 1.528(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
0.9905 -1.0054 1.9974 -0.0413 -0.2246 0.2187
-2.9720 5.0115 -4.9894 0.2286 0.8431 -0.4651
-1.0018 4.9896 3.0039 0.1261 0.5198 0.5059
1.0018 -4.9896 -3.0039 -0.1261 -0.5198 -0.5059
-2.0161 -1.0048 4.9859 -0.5115 0.0430 0.4753
-2.9849 -3.9772 -5.0085 -0.4302 0.0159 -0.8106
5.0064 3.9876 -1.9766 0.9517 -0.1218 0.0685
-4.9850 -0.9806 -3.0099 -0.5241 0.4700 -0.5243
