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_4026756
_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          'C17 H24 N2 O4'
_chemical_formula_moiety         'C17 H24 N2 O4'
_chemical_formula_sum            'C17 H24 N2 O4'
_chemical_formula_weight         320.38
_chemical_name_systematic
; 
Methyl 2-{(E)-[4-(2-tert-butoxy-2-oxoethyl)phenyl]diazenyl}-2-methyl
propanoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 95.317(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1381(6)
_cell_length_b                   23.0890(9)
_cell_length_c                   8.4213(6)
_cell_measurement_temperature    90(2)
_cell_volume                     1769.16(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6233
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9648
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         6233
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0783
_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^)+(0.1626P)^2^+2.8552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2472
_reflns_number_gt                5515
_reflns_number_total             6233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201358e_si_006.cif
_cod_data_source_block           dk110b
_cod_database_code               4026756