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_4035442
_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         'C18 H13 Cl N2 O3'
_chemical_formula_sum            'C18 H13 Cl N2 O3'
_chemical_formula_weight         340.75
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.1986(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1387(2)
_cell_length_b                   8.0853(2)
_cell_length_c                   15.9792(3)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.57
_cell_measurement_theta_min      3.68
_cell_volume                     1552.25(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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0134
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.046
_diffrn_reflns_theta_min         3.679
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  0.9006
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5 (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0447P)^2^+0.5736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3010
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00222_si_002.cif
_cod_data_source_block           2p
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035442
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.564
_shelx_estimated_absorpt_t_max   0.870
_shelx_res_checksum              58441
_shelx_hkl_checksum              58948