Generation of cocrystals of Tavaborole (AN2690): opportunities for boron-containing APIs
Campillo-Alvarado, Gonzalo; Staudt, Colton; Bak, Melissa; MacGillivray, Len R.; CrystEngComm  (2017) –; doi:10.1039/C7CE00314E

data_7227962
_publ_section_title
;
 Generation of cocrystals of Tavaborole (AN2690): opportunities for
 boron-containing APIs
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00314E
_journal_year                    2017
_chemical_formula_moiety         '2(C7 H6 B F O2), C12 H12 N2'
_chemical_formula_sum            'C26 H24 B2 F2 N2 O4'
_chemical_formula_weight         488.09
_chemical_name_common            2(AN2690)(bpeta)
_chemical_name_systematic
'5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, 1,2-bis(4-pyridyl)ethane'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.690(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0294(15)
_cell_length_b                   5.9476(6)
_cell_length_c                   14.5384(15)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      1.00
_cell_measurement_theta_min      25.35
_cell_volume                     1215.8(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6955
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.367
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         2.829
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       irregular
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Slow evaporation of a methanol solution containing 1 equivalent of 4,4'-bpeta and 2 equivalents of AN2690'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0467
_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/[\s^2^(Fo^2^)+(0.0850P)^2^+0.2480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1760
_reflns_number_total             2208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00314e2.cif
_cod_data_source_block           mcg16173a
_cod_database_code               7227962
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.967
_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:
 C7(H7A,H7B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C9(H9), C8(H8), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'