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_7156279
_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         'C19 H14 B N2 O2, C16 H36 N'
_chemical_formula_sum            'C35 H50 B N3 O2'
_chemical_formula_weight         555.59
_chemical_name_common            'compound 6b'
_chemical_name_systematic
'Tetra-n-butylammonium {N?-(hydroxy-kappaO)-N-{2-(hydroxy-kappaO)phenyl}-benzene?carboximidamidato-kappaN}(phenyl)borate'
_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
_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
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   19.0833(5)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.16
_cell_measurement_theta_min      3.43
_cell_volume                     3263.61(15)
_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    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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  0.0893
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            90976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
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_diffrn_reflns_theta_max         73.987
_diffrn_reflns_theta_min         3.429
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.9194
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.372
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_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.695
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0624
_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^)+(0.0962P)^2^+1.1326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5673
_reflns_number_total             6562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00998h2.cif
_cod_data_source_block           dgh1707
_cod_depositor_comments
'Adding full bibliography for 7156277--7156280.cif.'
_cod_database_code               7156279
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.826
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              64386