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_7156277
_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         'C16 H16 B N2 O2, C16 H36 N'
_chemical_formula_sum            'C32 H52 B N3 O2'
_chemical_formula_weight         521.57
_chemical_name_common            'compound 6a'
_chemical_name_systematic
'[nBu4N][(N?-(hydroxy-kappaO)-N-{2-(hydroxy-kappaO)phenyl}-2-methyl?propan?imid-amidato-kappaN)(phenyl)borate]'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.9063(5)
_cell_length_b                   21.5998(6)
_cell_length_c                   33.6902(9)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.17
_cell_measurement_theta_min      3.46
_cell_volume                     13030.4(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_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  0.1059
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            77128
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.829
_diffrn_reflns_theta_min         2.623
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_description       plate
_exptl_crystal_F_000             4576
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         11938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1225P)^2^+5.1297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7068
_reflns_number_total             11938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00998h2.cif
_cod_data_source_block           dgh1702
_cod_depositor_comments
'Adding full bibliography for 7156277--7156280.cif.'
_cod_database_code               7156277
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              78273