Synthesis of Oxazolo[4,5-c]quinoline TRPV1 Antagonists
Eric A. Voight; Jerome F. Daanen; Michael E. Kort; Journal of Organic Chemistry 75 (2010) 8713–8715; doi:10.1021/jo101938b

data_4025907
_publ_section_title
;
 Synthesis of Oxazolo[4,5-c]quinoline TRPV1 Antagonists
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8713
_journal_page_last               8715
_journal_paper_doi               10.1021/jo101938b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H16 F3 N3 O2, C1 H4 O1'
_chemical_formula_sum            'C22 H20 F3 N3 O3'
_chemical_formula_weight         431.41
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                64.673(9)
_cell_angle_beta                 87.338(10)
_cell_angle_gamma                67.624(10)
_cell_formula_units_Z            2
_cell_length_a                   10.064(8)
_cell_length_b                   10.526(8)
_cell_length_c                   11.221(8)
_cell_measurement_reflns_used    946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.3805
_cell_measurement_theta_min      2.784
_cell_volume                     983.8(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11477
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         8621
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+0.0838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                7562
_reflns_number_total             8621
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo101938b_si_002.cif
_cod_data_source_block           S-4
_cod_database_code               4025907