Valdecoxib vs. borazavaldecoxib: isoxazole BN/CC isosterism as a case study in designing and stabilizing boron heterocycles.
Boghi, Michele; Hall, Dennis G.; Organic & biomolecular chemistry 16 (2018) 4849–4856; doi:10.1039/c8ob00998h

data_7156280
_publ_section_title
;
 Valdecoxib vs. borazavaldecoxib: isoxazole BN/CC isosterism as a case
 study in designing and stabilizing boron heterocycles.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4849
_journal_page_last               4856
_journal_paper_doi               10.1039/c8ob00998h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C14 H14 B N3 O3 S, 0.5(C6 H14)'
_chemical_formula_sum            'C17 H21 B N3 O3 S'
_chemical_formula_weight         358.24
_chemical_name_common            'compound 2'
_chemical_name_systematic
4-(2-methyl-4-phenyl-1,3,5,2-oxadiazaborol-3(2H)-yl)benzenesulfonamide
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7903(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7713(2)
_cell_length_b                   7.93520(14)
_cell_length_c                   17.9462(3)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.76
_cell_measurement_theta_min      3.47
_cell_volume                     1812.37(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12464
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.887
_diffrn_reflns_theta_min         3.473
_exptl_absorpt_coefficient_mu    1.762
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       fragment
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0946P)^2^+1.7529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00998h2.cif
_cod_data_source_block           dgh1703
_cod_depositor_comments
'Adding full bibliography for 7156277--7156280.cif.'
_cod_original_cell_volume        1812.36(5)
_cod_database_code               7156280
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.822
_shelx_res_checksum              12973