Dual Catalytic Synthesis of Antiviral Compounds Based on Metallocarbene-Azide Cascade Chemistry.
Atienza, Bren Jordan P.; Jensen, Lionel D.; Noton, Sarah L.; Ansalem, Anil Kumar Victoria; Hobman, Tom; Fearns, Rachel; Marchant, David J.; West, F. G.; The Journal of organic chemistry 83 (2018) 6829–6842; doi:10.1021/acs.joc.8b00222

data_4035440
_publ_section_title
;
 Dual Catalytic Synthesis of Antiviral Compounds Based on
 Metallocarbene-Azide Cascade Chemistry.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6829
_journal_page_last               6842
_journal_paper_doi               10.1021/acs.joc.8b00222
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C11 H9 N5 O3'
_chemical_formula_sum            'C11 H9 N5 O3'
_chemical_formula_weight         259.23
_chemical_name_systematic
'methyl 2-diazo-3-(2-azido-3-methylphenyl)-3-oxopropanoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                96.711(2)
_cell_angle_beta                 104.962(2)
_cell_angle_gamma                105.019(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3874(3)
_cell_length_b                   8.0591(4)
_cell_length_c                   10.8556(5)
_cell_measurement_reflns_used    8057
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.63
_cell_measurement_theta_min      4.30
_cell_volume                     591.25(5)
_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 0.969
_diffrn_measured_fraction_theta_max 0.958
_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  0.0177
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4241
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.056
_diffrn_reflns_theta_min         4.300
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7941
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       fragment
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0478P)^2^+0.1063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2041
_reflns_number_total             2302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00222_si_002.cif
_cod_data_source_block           1b
_cod_database_code               4035440
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.791
_shelx_estimated_absorpt_t_max   0.949
_shelx_res_checksum              2543
_shelx_hkl_checksum              21827