#------------------------------------------------------------------------------
#$Date: 2022-04-09 01:41:59 +0300 (Sat, 09 Apr 2022) $
#$Revision: 274437 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244747.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_7244747
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 O3'
_chemical_formula_sum            'C11 H13 B F N O3'
_chemical_formula_weight         237.03
_chemical_melting_point          358(2)
_chemical_name_systematic
5-Fluoro-3-morpholin-4-yl-2,1-benzoxaborol-1(3H)-ol
_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
_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                99.383(3)
_cell_angle_beta                 100.605(4)
_cell_angle_gamma                91.220(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1181(3)
_cell_length_b                   9.4155(4)
_cell_length_c                   10.1914(4)
_cell_measurement_reflns_used    8056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0630
_cell_measurement_theta_min      4.1200
_cell_volume                     568.53(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00   5.00   1.00  140.00    --  -12.80 123.00-104.31   72
  2  ω    -89.00 -17.00   1.00  140.00    --  -12.80 157.00 112.09   72
  3  ω    -99.00  74.00   1.00  140.00    --  -12.80   0.00 150.00  173
  4  ω    -83.00  14.00   1.00  140.00    --  -12.80 -57.00 -60.00   97
  5  ω    -85.00  10.00   1.00  140.00    --  -12.80 -38.00  90.00   95
  6  ω    -72.00  -1.00   1.00  140.00    --  -12.80 131.00  -3.11   71
  7  ω    -85.00  10.00   1.00  140.00    --  -12.80 -38.00   0.00   95
  8  ω    -62.00 -16.00   1.00  140.00    --   13.11 155.00  80.83   46
  9  ω    -71.00  -1.00   1.00  140.00    --  -12.80 130.00 -50.66   70
 10  ω    -83.00 -12.00   1.00  140.00    --  -12.80 149.00  58.90   71
 11  ω     53.00  99.00   1.00  140.00    --   13.11-179.00-180.00   46
 12  ω     -9.00  86.00   1.00  140.00    --   13.11  38.00-120.00   95
 13  ω     -4.00  53.00   1.00  140.00    --   13.11 -99.00-120.00   57
 14  ω     -4.00  53.00   1.00  140.00    --   13.11 -99.00-180.00   57
 15  ω   -100.00 -34.00   1.00  140.00    --  -12.80-179.00  60.00   66
 16  ω    -71.00  -1.00   1.00  140.00    --  -12.80 130.00-162.09   70
 17  ω    -74.00 100.00   1.00  140.00    --   13.11   0.00-180.00  174
 18  ω    -74.00  28.00   1.00  140.00    --   13.11   0.00-120.00  102
 19  ω    -74.00 100.00   1.00  140.00    --   13.11   0.00-150.00  174
;
_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      -0.0267929000
_diffrn_orient_matrix_UB_12      0.0578730000
_diffrn_orient_matrix_UB_13      -0.0357523000
_diffrn_orient_matrix_UB_21      -0.0974038000
_diffrn_orient_matrix_UB_22      -0.0398049000
_diffrn_orient_matrix_UB_23      -0.0378432000
_diffrn_orient_matrix_UB_31      -0.0612012000
_diffrn_orient_matrix_UB_32      0.0302108000
_diffrn_orient_matrix_UB_33      0.0495210000
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1:1 molar mixture of dichloromethane and hexane'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0338
_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)+(0.0407P)²+0.0895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2123
_reflns_number_total             2607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00279e2.cif
_cod_data_source_block           TvO
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '338-378 K' was changed to
'358(2)' -- 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               7244747
_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   0.996
_shelx_estimated_absorpt_t_min   0.953
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3)
;
_olex2_date_sample_data_collection 2017-04-14
_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.776
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
O2 O 0.43870(14) 0.75362(8) 0.47854(7) 0.0412(2) Uani 1 1 d . . . . .
O3 O 0.11480(14) 1.07888(9) 0.20234(9) 0.0471(2) Uani 1 1 d . . . . .
O1 O 0.80450(15) 0.69699(10) 0.58054(9) 0.0491(2) Uani 1 1 d . . . . .
H1 H 0.794(3) 0.7592(19) 0.6469(18) 0.074 Uiso 1 1 d . U . . .
N1 N 0.19120(15) 0.80563(10) 0.28018(9) 0.0362(2) Uani 1 1 d . . . . .
F1 F 0.32723(19) 0.30198(10) -0.01153(9) 0.0838(3) Uani 1 1 d . . . . .
C6 C 0.37881(19) 0.57797(11) 0.28089(11) 0.0379(3) Uani 1 1 d . . . . .
C7 C 0.27043(19) 0.69789(12) 0.35836(11) 0.0377(3) Uani 1 1 d . . . . .
H7 H 0.143569 0.655907 0.387839 0.045 Uiso 1 1 calc R U . . .
C1 C 0.59002(19) 0.55770(12) 0.35025(11) 0.0392(3) Uani 1 1 d . . . . .
C8 C 0.36484(19) 0.88611(13) 0.23782(12) 0.0416(3) Uani 1 1 d . . . . .
H8A H 0.458445 0.819756 0.193487 0.050 Uiso 1 1 calc R U . . .
H8B H 0.457510 0.944551 0.316355 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0495(2) 0.90640(13) 0.34444(13) 0.0439(3) Uani 1 1 d . . . . .
H11A H 0.137081 0.965594 0.424430 0.053 Uiso 1 1 calc R U . . .
H11B H -0.066925 0.853562 0.372330 0.053 Uiso 1 1 calc R U . . .
C10 C -0.0531(2) 1.00078(14) 0.24641(14) 0.0490(3) Uani 1 1 d . . . . .
H10B H -0.146300 0.941567 0.168587 0.059 Uiso 1 1 calc R U . . .
H10A H -0.146560 1.068112 0.289701 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2579(2) 0.98140(14) 0.14152(13) 0.0498(3) Uani 1 1 d . . . . .
H9B H 0.372967 1.035864 0.114086 0.060 Uiso 1 1 calc R U . . .
H9A H 0.172326 0.921836 0.061015 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7140(2) 0.44900(13) 0.29486(14) 0.0504(3) Uani 1 1 d . . . . .
H2 H 0.855963 0.433931 0.339942 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2850(2) 0.49367(13) 0.15831(12) 0.0483(3) Uani 1 1 d . . . . .
H5 H 0.143103 0.507723 0.112490 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4134(3) 0.38828(14) 0.10838(13) 0.0552(4) Uani 1 1 d . . . . .
C3 C 0.6236(3) 0.36382(14) 0.17210(15) 0.0583(4) Uani 1 1 d . . . . .
H3 H 0.704024 0.291082 0.133352 0.070 Uiso 1 1 calc R U . . .
B1 B 0.6242(2) 0.67359(14) 0.48095(13) 0.0388(3) 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'
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
B1 O2 C7 110.22(9) . . ?
C9 O3 C10 110.21(9) . . ?
B1 O1 H1 115.8(12) . . ?
C7 N1 C8 114.65(9) . . ?
C7 N1 C11 113.67(9) . . ?
C11 N1 C8 109.32(9) . . ?
C1 C6 C7 111.17(10) . . ?
C5 C6 C7 126.36(11) . . ?
C5 C6 C1 122.45(11) . . ?
O2 C7 C6 104.89(9) . . ?
O2 C7 H7 108.3 . . ?
N1 C7 O2 113.51(9) . . ?
N1 C7 C6 113.33(9) . . ?
N1 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C6 C1 C2 119.21(11) . . ?
C6 C1 B1 104.65(10) . . ?
C2 C1 B1 136.14(11) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.18(10) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
N1 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
N1 C11 C10 109.67(10) . . ?
H11A C11 H11B 108.2 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
O3 C10 C11 110.98(10) . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C9 C8 111.53(9) . . ?
O3 C9 H9A 109.3 . . ?
O3 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.26(12) . . ?
C3 C2 H2 120.4 . . ?
C6 C5 H5 122.0 . . ?
C4 C5 C6 116.06(12) . . ?
C4 C5 H5 122.0 . . ?
F1 C4 C5 118.12(13) . . ?
F1 C4 C3 117.84(13) . . ?
C5 C4 C3 124.03(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.99(12) . . ?
C4 C3 H3 120.5 . . ?
O2 B1 C1 108.97(10) . . ?
O1 B1 O2 123.96(11) . . ?
O1 B1 C1 127.05(11) . . ?
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
O2 C7 1.4624(13) . ?
O2 B1 1.3741(16) . ?
O3 C10 1.4293(15) . ?
O3 C9 1.4287(15) . ?
O1 H1 0.832(18) . ?
O1 B1 1.3418(16) . ?
N1 C7 1.4287(14) . ?
N1 C8 1.4595(14) . ?
N1 C11 1.4569(14) . ?
F1 C4 1.3610(15) . ?
C6 C7 1.5072(16) . ?
C6 C1 1.3871(16) . ?
C6 C5 1.3833(16) . ?
C7 H7 0.9800 . ?
C1 C2 1.3943(17) . ?
C1 B1 1.5564(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5074(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.5046(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.3835(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.3697(19) . ?
C4 C3 1.372(2) . ?
C3 H3 0.9300 . ?
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
N1 C8 C9 O3 58.31(13) . . . . ?
N1 C11 C10 O3 -58.75(13) . . . . ?
F1 C4 C3 C2 -179.29(12) . . . . ?
C6 C1 C2 C3 -0.05(18) . . . . ?
C6 C1 B1 O2 -1.18(12) . . . . ?
C6 C1 B1 O1 -179.83(12) . . . . ?
C6 C5 C4 F1 179.54(11) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C7 O2 B1 O1 -178.45(11) . . . . ?
C7 O2 B1 C1 2.84(12) . . . . ?
C7 N1 C8 C9 172.52(9) . . . . ?
C7 N1 C11 C10 -171.46(9) . . . . ?
C7 C6 C1 C2 178.78(10) . . . . ?
C7 C6 C1 B1 -0.91(12) . . . . ?
C7 C6 C5 C4 -178.43(11) . . . . ?
C1 C6 C7 O2 2.54(12) . . . . ?
C1 C6 C7 N1 126.89(10) . . . . ?
C1 C6 C5 C4 -0.18(17) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C8 N1 C7 O2 55.12(12) . . . . ?
C8 N1 C7 C6 -64.41(12) . . . . ?
C8 N1 C11 C10 59.03(12) . . . . ?
C11 N1 C7 O2 -71.65(12) . . . . ?
C11 N1 C7 C6 168.82(9) . . . . ?
C11 N1 C8 C9 -58.50(12) . . . . ?
C10 O3 C9 C8 -57.63(13) . . . . ?
C9 O3 C10 C11 57.55(13) . . . . ?
C2 C1 B1 O2 179.21(13) . . . . ?
C2 C1 B1 O1 0.6(2) . . . . ?
C5 C6 C7 O2 -179.04(10) . . . . ?
C5 C6 C7 N1 -54.69(15) . . . . ?
C5 C6 C1 C2 0.30(17) . . . . ?
C5 C6 C1 B1 -179.40(11) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
B1 O2 C7 N1 -127.52(10) . . . . ?
B1 O2 C7 C6 -3.28(11) . . . . ?
B1 C1 C2 C3 179.53(13) . . . . ?
