Effect of substituents in novel bioactive tavaborole derivatives on intermolecular interactions hierarchy
Dąbrowska, Anna Maria; Adamczyk-Woźniak, Agnieszka; Madura, Izabela Dorota; CrystEngComm  (2022) –; doi:10.1039/D2CE00279E

data_7244747
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -67.00   5.00   1.00  140.00    --  -12.80 123.00-104.31   72
  2  \w    -89.00 -17.00   1.00  140.00    --  -12.80 157.00 112.09   72
  3  \w    -99.00  74.00   1.00  140.00    --  -12.80   0.00 150.00  173
  4  \w    -83.00  14.00   1.00  140.00    --  -12.80 -57.00 -60.00   97
  5  \w    -85.00  10.00   1.00  140.00    --  -12.80 -38.00  90.00   95
  6  \w    -72.00  -1.00   1.00  140.00    --  -12.80 131.00  -3.11   71
  7  \w    -85.00  10.00   1.00  140.00    --  -12.80 -38.00   0.00   95
  8  \w    -62.00 -16.00   1.00  140.00    --   13.11 155.00  80.83   46
  9  \w    -71.00  -1.00   1.00  140.00    --  -12.80 130.00 -50.66   70
 10  \w    -83.00 -12.00   1.00  140.00    --  -12.80 149.00  58.90   71
 11  \w     53.00  99.00   1.00  140.00    --   13.11-179.00-180.00   46
 12  \w     -9.00  86.00   1.00  140.00    --   13.11  38.00-120.00   95
 13  \w     -4.00  53.00   1.00  140.00    --   13.11 -99.00-120.00   57
 14  \w     -4.00  53.00   1.00  140.00    --   13.11 -99.00-180.00   57
 15  \w   -100.00 -34.00   1.00  140.00    --  -12.80-179.00  60.00   66
 16  \w    -71.00  -1.00   1.00  140.00    --  -12.80 130.00-162.09   70
 17  \w    -74.00 100.00   1.00  140.00    --   13.11   0.00-180.00  174
 18  \w    -74.00  28.00   1.00  140.00    --   13.11   0.00-120.00  102
 19  \w    -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       '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0407P)^2^+0.0895P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              26611
_shelx_hkl_checksum              36173
_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