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_7244746
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  51.00   1.00   30.00    --   11.71 -99.00   0.00   50
  2  \w    -11.00  85.00   1.00   30.00    --   11.71  38.00-120.00   96
  3  \w     61.00 101.00   1.00   30.00    --   11.71-179.00 150.00   40
  4  \w    -63.00 -37.00   1.00   30.00    --   11.71 -38.00 -90.00   26
  5  \w    -27.00  20.00   1.00   30.00    --   11.71 -38.00 -90.00   47
  6  \w    -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       '\w 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/[\s^2^(Fo^2^)+(0.0409P)^2^+0.5010P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              31958
_shelx_hkl_checksum              93612
_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