Synthesis of nuevamine and a cyano-chilenine analog via divergent C(sp3)–H bond functionalization of isoindolinone derivatives
Gómez-Prado, Raúl A.; Silva, Ana L.; Miranda, Luis D.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01304E

data_7158867
_publ_section_title
;
 Synthesis of nuevamine and a cyano-chilenine analog via divergent
 C(sp3)--H bond functionalization of isoindolinone derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01304E
_journal_year                    2022
_chemical_formula_moiety         'C22 H20 N2 O6'
_chemical_formula_sum            'C22 H20 N2 O6'
_chemical_formula_weight         408.40
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                94.605(3)
_cell_angle_beta                 108.730(4)
_cell_angle_gamma                98.534(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3790(13)
_cell_length_b                   10.2477(16)
_cell_length_c                   12.547(2)
_cell_measurement_reflns_used    3997
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.48
_cell_volume                     999.5(3)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         1.730
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       platy
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0756P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2909
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01304e2.cif
_cod_data_source_block           002MGL14
_cod_original_cell_volume        999.6(3)
_cod_database_code               7158867
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
_shelx_res_checksum              6907