Synthesis of Mutual Azo Prodrugs of Anti-inflammatory Agents and Peptides Facilitated by α-Aminoisobutyric Acid
David A. Kennedy; Nagarajan Vembu; Frank R. Fronczek; Marc Devocelle; Journal of Organic Chemistry 76 (2011) 9641–9647; doi:10.1021/jo201358e

data_4026752
_publ_section_title
;
 Synthesis of Mutual Azo Prodrugs of Anti-inflammatory Agents and Peptides
 Facilitated by \a-Aminoisobutyric Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9641
_journal_page_last               9647
_journal_paper_doi               10.1021/jo201358e
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        synthesized
_chemical_formula_iupac          'C8 H7 B F4 N2 O2'
_chemical_formula_moiety         C8H7N2O2.BF4
_chemical_formula_sum            'C8 H7 B F4 N2 O2'
_chemical_formula_weight         249.97
_chemical_name_systematic
; 
4-(carboxymethyl)benzenediazonium tetrafluoroborate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.814(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4007(10)
_cell_length_b                   16.268(3)
_cell_length_c                   11.926(2)
_cell_measurement_reflns_used    2919
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      2.5
_cell_volume                     1021.7(3)
_computing_cell_refinement       'Denzo&Scalepack (Otwinowski&Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        Denzo&Scalepack
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       '\w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14147
_diffrn_reflns_theta_full        32.47
_diffrn_reflns_theta_max         32.47
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.4089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                2366
_reflns_number_total             3397
_reflns_threshold_expression     'I >2\s(I)'
_cod_data_source_file            jo201358e_si_002.cif
_cod_data_source_block           dk296
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026752