#------------------------------------------------------------------------------
#$Date: 2022-04-09 01:41:59 +0300 (Sat, 09 Apr 2022) $
#$Revision: 274437 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244746.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_7244746
loop_
_publ_author_name
'Dąbrowska, Anna Maria'
'Adamczyk-Woźniak, Agnieszka'
'Madura, Izabela Dorota'
_publ_section_title
;
 Effect of substituents in novel bioactive tavaborole derivatives on
 intermolecular interactions hierarchy
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00279E
_journal_year                    2022
_chemical_formula_moiety         'C11 H13 B F N O2 S'
_chemical_formula_sum            'C11 H13 B F N O2 S'
_chemical_formula_weight         253.09
_chemical_melting_point          350(8)
_chemical_name_systematic
5-Fluoro-3-thiomorpholin-4-yl-2,1-benzoxaborol-1(3H)-ol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.420(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0320(3)
_cell_length_b                   6.2712(3)
_cell_length_c                   21.3774(9)
_cell_measurement_reflns_used    4087
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.1280
_cell_measurement_theta_min      4.1570
_cell_volume                     1194.52(9)
_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_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  51.00   1.00   30.00    --   11.71 -99.00   0.00   50
  2  ω    -11.00  85.00   1.00   30.00    --   11.71  38.00-120.00   96
  3  ω     61.00 101.00   1.00   30.00    --   11.71-179.00 150.00   40
  4  ω    -63.00 -37.00   1.00   30.00    --   11.71 -38.00 -90.00   26
  5  ω    -27.00  20.00   1.00   30.00    --   11.71 -38.00 -90.00   47
  6  ω    -69.00  49.00   1.00   30.00    --   11.71 -19.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522562000
_diffrn_orient_matrix_UB_12      -0.0636888000
_diffrn_orient_matrix_UB_13      -0.0130400000
_diffrn_orient_matrix_UB_21      -0.0154284000
_diffrn_orient_matrix_UB_22      0.0584944000
_diffrn_orient_matrix_UB_23      -0.0287236000
_diffrn_orient_matrix_UB_31      0.0580137000
_diffrn_orient_matrix_UB_32      0.0729918000
_diffrn_orient_matrix_UB_33      0.0116287000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1:1 molar mixture of dichloromethane and hexane'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0413
_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)+(0.0409P)²+0.5010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2329
_reflns_number_total             2966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00279e2.cif
_cod_data_source_block           TvS
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '343-358 K' was changed to
'350(8)' -- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7244746
_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_max   0.899
_shelx_estimated_absorpt_t_min   0.854
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
;
_olex2_submission_original_sample_id MLe-5
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.554
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
B1 B 0.8648(2) 0.4992(3) 0.27987(9) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.97078(17) 0.5138(3) 0.34451(8) 0.0379(4) Uani 1 1 d . . . . .
C2 C 1.0816(2) 0.3856(3) 0.37847(9) 0.0493(5) Uani 1 1 d . . . . .
H2 H 1.105294 0.254704 0.362178 0.059 Uiso 1 1 calc R U . . .
C3 C 1.1559(2) 0.4542(4) 0.43647(9) 0.0547(5) Uani 1 1 d . . . . .
H3 H 1.229995 0.370171 0.459823 0.066 Uiso 1 1 calc R U . . .
C4 C 1.1191(2) 0.6479(4) 0.45917(8) 0.0508(5) Uani 1 1 d . . . . .
C5 C 1.01031(19) 0.7805(3) 0.42766(8) 0.0436(4) Uani 1 1 d . . . . .
H5 H 0.987173 0.910796 0.444450 0.052 Uiso 1 1 calc R U . . .
C6 C 0.93760(16) 0.7087(3) 0.36969(7) 0.0354(4) Uani 1 1 d . . . . .
C7 C 0.81725(17) 0.8248(3) 0.32535(7) 0.0351(3) Uani 1 1 d . . . . .
H7 H 0.8574(18) 0.953(3) 0.3079(7) 0.031(4) Uiso 1 1 d . . . . .
C8 C 0.61409(18) 0.7111(3) 0.37870(8) 0.0376(4) Uani 1 1 d . . . . .
H8A H 0.686554 0.606564 0.398056 0.045 Uiso 1 1 calc R U . . .
H8B H 0.549304 0.642619 0.343793 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5209(2) 0.7863(3) 0.42710(8) 0.0468(4) Uani 1 1 d . . . . .
H9A H 0.586066 0.854015 0.462050 0.056 Uiso 1 1 calc R U . . .
H9B H 0.474489 0.663991 0.443817 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4944(2) 1.1514(3) 0.35816(10) 0.0486(5) Uani 1 1 d . . . . .
H10A H 0.431667 1.255117 0.332590 0.058 Uiso 1 1 calc R U . . .
H10B H 0.559317 1.228115 0.391284 0.058 Uiso 1 1 calc R U . . .
C11 C 0.58968(18) 1.0364(3) 0.31700(8) 0.0422(4) Uani 1 1 d . . . . .
H11A H 0.525235 0.959037 0.283862 0.051 Uiso 1 1 calc R U . . .
H11B H 0.646712 1.139655 0.296943 0.051 Uiso 1 1 calc R U . . .
F1 F 1.19459(14) 0.7133(3) 0.51632(6) 0.0787(4) Uani 1 1 d . . . . .
N1 N 0.69267(14) 0.8874(2) 0.35450(6) 0.0341(3) Uani 1 1 d . . . . .
O1 O 0.85561(16) 0.3376(2) 0.23776(6) 0.0546(4) Uani 1 1 d . . . . .
H1 H 0.796(3) 0.352(4) 0.2067(13) 0.082 Uiso 1 1 d . U . . .
O2 O 0.77614(12) 0.6779(2) 0.27182(5) 0.0410(3) Uani 1 1 d . . . . .
S1 S 0.37671(5) 0.97211(8) 0.39399(2) 0.04820(16) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O1 B1 C1 126.94(17) . . ?
O1 B1 O2 123.98(16) . . ?
O2 B1 C1 109.06(15) . . ?
C2 C1 B1 135.84(17) . . ?
C6 C1 B1 104.88(14) . . ?
C6 C1 C2 119.27(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.43(19) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.00(17) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 123.91(17) . . ?
F1 C4 C3 118.03(17) . . ?
F1 C4 C5 118.05(19) . . ?
C4 C5 H5 122.0 . . ?
C4 C5 C6 116.06(18) . . ?
C6 C5 H5 122.0 . . ?
C1 C6 C7 111.14(14) . . ?
C5 C6 C1 122.31(16) . . ?
C5 C6 C7 126.54(16) . . ?
C6 C7 H7 111.2(9) . . ?
N1 C7 C6 113.40(13) . . ?
N1 C7 H7 107.9(9) . . ?
N1 C7 O2 113.32(12) . . ?
O2 C7 C6 104.56(13) . . ?
O2 C7 H7 106.2(9) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.42(14) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 S1 112.33(12) . . ?
H9A C9 H9B 107.9 . . ?
S1 C9 H9A 109.1 . . ?
S1 C9 H9B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C11 C10 S1 112.42(13) . . ?
S1 C10 H10A 109.1 . . ?
S1 C10 H10B 109.1 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C11 C10 110.96(14) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C7 N1 C8 114.30(13) . . ?
C7 N1 C11 114.37(13) . . ?
C8 N1 C11 112.17(12) . . ?
B1 O1 H1 116(2) . . ?
B1 O2 C7 110.27(13) . . ?
C10 S1 C9 97.58(8) . . ?
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
B1 C1 1.549(3) . ?
B1 O1 1.349(2) . ?
B1 O2 1.372(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(3) . ?
C4 C5 1.376(3) . ?
C4 F1 1.361(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 C7 1.507(2) . ?
C7 H7 0.980(17) . ?
C7 N1 1.428(2) . ?
C7 O2 1.469(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(2) . ?
C8 N1 1.454(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 S1 1.8035(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(3) . ?
C10 S1 1.802(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.462(2) . ?
O1 H1 0.79(3) . ?
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
O1 H1 S1 0.79(3) 2.56(3) 3.3335(15) 169(3) 2_645 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
B1 C1 C2 C3 179.39(18) . . . . ?
B1 C1 C6 C5 -179.72(15) . . . . ?
B1 C1 C6 C7 -0.55(17) . . . . ?
C1 B1 O2 C7 2.81(18) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 N1 126.07(15) . . . . ?
C1 C6 C7 O2 2.15(17) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 C7 178.89(15) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 F1 -179.55(18) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -178.59(16) . . . . ?
C5 C6 C7 N1 -54.8(2) . . . . ?
C5 C6 C7 O2 -178.72(15) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 N1 C8 -60.60(18) . . . . ?
C6 C7 N1 C11 168.17(14) . . . . ?
C6 C7 O2 B1 -3.04(17) . . . . ?
C8 C9 S1 C10 -50.81(16) . . . . ?
C9 C8 N1 C7 160.74(13) . . . . ?
C9 C8 N1 C11 -66.97(18) . . . . ?
C10 C11 N1 C7 -160.67(14) . . . . ?
C10 C11 N1 C8 67.07(18) . . . . ?
C11 C10 S1 C9 51.24(14) . . . . ?
F1 C4 C5 C6 179.46(16) . . . . ?
N1 C7 O2 B1 -127.02(14) . . . . ?
N1 C8 C9 S1 61.84(17) . . . . ?
O1 B1 C1 C2 0.7(3) . . . . ?
O1 B1 C1 C6 -179.98(17) . . . . ?
O1 B1 O2 C7 -178.55(16) . . . . ?
O2 B1 C1 C2 179.31(18) . . . . ?
O2 B1 C1 C6 -1.39(18) . . . . ?
O2 C7 N1 C8 58.41(17) . . . . ?
O2 C7 N1 C11 -72.82(17) . . . . ?
S1 C10 C11 N1 -62.26(17) . . . . ?
