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#$Date: 2022-08-17 04:06:57 +0300 (Wed, 17 Aug 2022) $
#$Revision: 277274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245336.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_7245336
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         '2(C19 H23 B F N3 O5 Si), H2O'
_chemical_formula_sum            'C19 H24 B F N3 O5.5 Si'
_chemical_formula_weight         440.31
_chemical_melting_point          402
_chemical_name_systematic
;
6-[2-methyl-2-(N-methylpyrazinamido)propoxycarbonyl]-7-fluoro-1,1-dimethyl-3-hydroxybenzo[1,2,3]siloxaborole
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                100.665(2)
_cell_angle_beta                 100.149(2)
_cell_angle_gamma                91.918(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3320(2)
_cell_length_b                   10.4076(2)
_cell_length_c                   14.5602(4)
_cell_measurement_reflns_used    8593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3880
_cell_measurement_theta_min      3.0740
_cell_volume                     1072.28(5)
_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 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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  0.0648
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15571
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.668
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4189
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0525
_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)+(0.0978P)²+0.4598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3702
_reflns_number_total             4189
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra03910a7.cif
_cod_data_source_block           3d
_cod_original_formula_sum        'C19 H24 B F N3 O5.50 Si'
_cod_database_code               7245336
_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 0.413
_oxdiff_exptl_absorpt_empirical_full_max 2.686
_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, -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
C18 C 0.4230(3) 0.10471(18) 0.73500(13) 0.0219(4) Uani 1 1 d . . . . .
H18A H 0.5525 0.1375 0.7417 0.033 Uiso 1 1 calc R U . . .
H18B H 0.4066 0.0137 0.7003 0.033 Uiso 1 1 calc R U . . .
H18C H 0.3919 0.1087 0.7982 0.033 Uiso 1 1 calc R U . . .
C19 C 0.0936(3) 0.1352(2) 0.66830(14) 0.0249(4) Uani 1 1 d . . . . .
H19A H 0.0107 0.1875 0.6321 0.037 Uiso 1 1 calc R U . . .
H19B H 0.0609 0.1393 0.7311 0.037 Uiso 1 1 calc R U . . .
H19C H 0.0806 0.0439 0.6342 0.037 Uiso 1 1 calc R U . . .
O6 O 0.0890(5) 0.4356(4) 0.5142(3) 0.0392(8) Uani 0.5 1 d D . P . .
H6B H 0.073(9) 0.480(6) 0.468(3) 0.047 Uiso 0.5 1 d D U P . .
H6A H 0.021(8) 0.460(6) 0.557(3) 0.047 Uiso 0.5 1 d D U P . .
Si1 Si 0.05699(7) 0.20197(5) 1.15750(3) 0.02033(17) Uani 1 1 d . . . . .
O4 O 0.27423(19) 0.33125(13) 0.82599(9) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.11644(19) 0.52310(13) 1.34114(9) 0.0207(3) Uani 1 1 d D . . . .
O5 O 0.64336(18) 0.27234(13) 0.64899(9) 0.0206(3) Uani 1 1 d . . . . .
F1 F 0.15068(19) 0.21177(11) 0.94644(8) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.05359(19) 0.30393(13) 1.26021(9) 0.0211(3) Uani 1 1 d . . . . .
O3 O 0.2970(2) 0.55075(13) 0.85674(9) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.7096(2) 0.21779(16) 0.45943(12) 0.0234(4) Uani 1 1 d . . . . .
N1 N 0.3469(2) 0.19013(15) 0.58434(10) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.1459(3) 0.33056(17) 1.09858(13) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.1805(3) 0.32834(18) 1.00822(13) 0.0183(4) Uani 1 1 d . . . . .
C5 C 0.2267(2) 0.56438(17) 1.13702(12) 0.0174(4) Uani 1 1 d . . . . .
H5 H 0.2423 0.6457 1.1807 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2728(2) 0.44828(18) 0.88173(12) 0.0167(4) Uani 1 1 d . . . . .
C6 C 0.1710(2) 0.45039(18) 1.16485(12) 0.0171(4) Uani 1 1 d . . . . .
C11 C 0.2948(2) 0.18951(17) 0.67992(12) 0.0174(4) Uani 1 1 d . . . . .
C13 C 0.5166(3) 0.23901(17) 0.57914(12) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.3091(2) 0.33328(17) 0.73123(12) 0.0164(4) Uani 1 1 d . . . . .
H10A H 0.4343 0.3745 0.7345 0.020 Uiso 1 1 calc R U . . .
H10B H 0.2159 0.3832 0.6973 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2383(2) 0.44095(18) 0.97877(12) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.2595(2) 0.55903(18) 1.04525(13) 0.0170(4) Uani 1 1 d . . . . .
H4 H 0.2972 0.6374 1.0271 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5540(3) 0.26254(17) 0.48487(12) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.4438(3) 0.3408(2) 0.43339(15) 0.0267(4) Uani 1 1 d . . . . .
H15 H 0.3342 0.3707 0.4542 0.032 Uiso 1 1 calc R U . . .
N3 N 0.4876(3) 0.37527(19) 0.35507(13) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.2217(3) 0.1178(2) 0.49868(13) 0.0243(4) Uani 1 1 d . . . . .
H12A H 0.1046 0.0910 0.5156 0.037 Uiso 1 1 calc R U . . .
H12B H 0.2803 0.0399 0.4717 0.037 Uiso 1 1 calc R U . . .
H12C H 0.1970 0.1743 0.4516 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6429(3) 0.3303(2) 0.33000(14) 0.0247(4) Uani 1 1 d . . . . .
H16 H 0.6803 0.3527 0.2754 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2217(4) 0.0749(2) 1.17993(16) 0.0333(5) Uani 1 1 d . . . . .
H8A H 0.1661 0.0123 1.2115 0.050 Uiso 1 1 calc R U . . .
H8B H 0.3370 0.1166 1.2208 0.050 Uiso 1 1 calc R U . . .
H8C H 0.2489 0.0287 1.1193 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7515(3) 0.2518(2) 0.38104(14) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.8601 0.2209 0.3596 0.029 Uiso 1 1 calc R U . . .
B1 B 0.1176(3) 0.4309(2) 1.26278(14) 0.0183(4) Uani 1 1 d . . . . .
C7 C -0.1804(3) 0.1292(2) 1.10350(15) 0.0292(4) Uani 1 1 d . . . . .
H7A H -0.2628 0.1991 1.0922 0.044 Uiso 1 1 calc R U . . .
H7B H -0.2265 0.0796 1.1467 0.044 Uiso 1 1 calc R U . . .
H7C H -0.1775 0.0703 1.0430 0.044 Uiso 1 1 calc R U . . .
H2 H 0.180(4) 0.5964(18) 1.347(2) 0.044 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'
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'
F F 0.0727 0.0534 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -3 0.0464
0 -5 3 0.0464
5 -2 0 0.0880
-2 1 0 0.0711
1 0 5 0.0235
-2 3 5 0.0377
0 0 -1 0.0390
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
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H6B O6 H6A 113(6) . . ?
O1 Si1 C7 109.96(9) . . ?
O1 Si1 C8 108.90(9) . . ?
C7 Si1 C8 111.91(11) . . ?
O1 Si1 C1 95.10(8) . . ?
C7 Si1 C1 115.19(9) . . ?
C8 Si1 C1 114.34(10) . . ?
C9 O4 C10 115.68(14) . . ?
B1 O2 H2 117(2) . . ?
B1 O1 Si1 113.93(12) . . ?
C14 N2 C17 115.78(17) . . ?
C13 N1 C12 120.77(15) . . ?
C13 N1 C11 120.07(14) . . ?
C12 N1 C11 118.42(15) . . ?
C2 C1 C6 119.34(16) . . ?
C2 C1 Si1 133.00(14) . . ?
C6 C1 Si1 107.61(13) . . ?
F1 C2 C1 117.27(16) . . ?
F1 C2 C3 120.20(16) . . ?
C1 C2 C3 122.50(17) . . ?
C4 C5 C6 119.95(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O3 C9 O4 123.58(16) . . ?
O3 C9 C3 122.79(16) . . ?
O4 C9 C3 113.63(15) . . ?
C5 C6 C1 119.32(16) . . ?
C5 C6 B1 129.83(17) . . ?
C1 C6 B1 110.77(16) . . ?
N1 C11 C19 110.81(14) . . ?
N1 C11 C10 106.30(14) . . ?
C19 C11 C10 108.07(15) . . ?
N1 C11 C18 110.29(14) . . ?
C19 C11 C18 108.76(15) . . ?
C10 C11 C18 112.59(15) . . ?
O5 C13 N1 123.61(16) . . ?
O5 C13 C14 117.06(16) . . ?
N1 C13 C14 119.23(16) . . ?
O4 C10 C11 106.02(13) . . ?
O4 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
O4 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C2 C3 C4 117.16(16) . . ?
C2 C3 C9 126.05(16) . . ?
C4 C3 C9 116.75(16) . . ?
C5 C4 C3 121.72(17) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
N2 C14 C15 121.86(17) . . ?
N2 C14 C13 116.45(16) . . ?
C15 C14 C13 121.22(17) . . ?
N3 C15 C14 121.96(19) . . ?
N3 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C16 N3 C15 115.92(18) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C16 C17 121.94(18) . . ?
N3 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
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 . . ?
N2 C17 C16 122.53(18) . . ?
N2 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
O2 B1 O1 119.34(17) . . ?
O2 B1 C6 127.94(17) . . ?
O1 B1 C6 112.54(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 . . ?
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
C18 C11 1.536(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C11 1.531(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O6 H6B 0.872(10) . ?
O6 H6A 0.874(10) . ?
Si1 O1 1.6706(14) . ?
Si1 C7 1.852(2) . ?
Si1 C8 1.855(2) . ?
Si1 C1 1.8751(19) . ?
O4 C9 1.334(2) . ?
O4 C10 1.4506(19) . ?
O2 B1 1.349(2) . ?
O2 H2 0.865(10) . ?
O5 C13 1.238(2) . ?
F1 C2 1.356(2) . ?
O1 B1 1.379(3) . ?
O3 C9 1.206(2) . ?
N2 C14 1.333(3) . ?
N2 C17 1.337(3) . ?
N1 C13 1.348(2) . ?
N1 C12 1.472(2) . ?
N1 C11 1.508(2) . ?
C1 C2 1.379(2) . ?
C1 C6 1.413(3) . ?
C2 C3 1.398(3) . ?
C5 C4 1.390(2) . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C9 C3 1.493(2) . ?
C6 B1 1.589(3) . ?
C11 C10 1.535(2) . ?
C13 C14 1.507(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C3 C4 1.402(3) . ?
C4 H4 0.9500 . ?
C14 C15 1.391(3) . ?
C15 N3 1.344(3) . ?
C15 H15 0.9500 . ?
N3 C16 1.329(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C17 H17 0.9500 . ?
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
-0.0061 5.0031 -2.9777 0.5341 -0.0022 0.5441
0.0061 -5.0031 2.9777 -0.5341 0.0022 -0.5441
4.9936 -1.9832 0.0166 0.5496 0.0168 -0.9410
-1.9978 0.9933 -0.0058 -0.1999 -0.0195 0.3952
0.9915 0.0000 5.0021 0.0904 -0.5515 -0.2762
-2.0082 2.9904 4.9996 -0.0600 -0.6767 0.4572
0.0013 0.0007 -0.9994 0.0119 0.1059 0.0251
