Copper-Catalyzed C(sp(3))-OH Cleavage with Concomitant C-C Coupling: Synthesis of 3-Substituted Isoindolinones.
Rao, H. Surya Prakash; Rao, A. Veera Bhadra; The Journal of organic chemistry 80 (2015) 1506–1516; doi:10.1021/jo502446k

data_4030563
_publ_section_title
;
 Copper-Catalyzed C(sp(3))-OH Cleavage with Concomitant C-C Coupling:
 Synthesis of 3-Substituted Isoindolinones.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1506
_journal_page_last               1516
_journal_paper_doi               10.1021/jo502446k
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2014-01-23
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                93.217(6)
_cell_angle_beta                 105.398(7)
_cell_angle_gamma                93.602(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4641(5)
_cell_length_b                   10.1247(6)
_cell_length_c                   11.5543(10)
_cell_measurement_reflns_used    2821
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.0234
_cell_measurement_theta_min      4.0256
_cell_volume                     837.76(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9916
_diffrn_measured_fraction_theta_max 0.9422
_diffrn_measurement_details
;
  1 omega  -24.00    6.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  -90.0000 30

  2 omega  -20.00   24.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000   30.0000 44

  3 omega  -47.00  -20.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   19.0000  -30.0000 27

  4 omega    1.00   54.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   19.0000  -30.0000 53

  5 omega  -90.00  -17.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -37.0000  150.0000 73

  6 omega  -15.00   23.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  120.0000 38

  7 omega  -93.00  -61.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000   60.0000 32

  8 omega  -93.00  -57.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000   90.0000 36

  9 omega  -86.00  -47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000  -90.0000 39

 10 omega  -27.00   -1.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000  -90.0000 26

 11 omega  -43.00   53.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   77.0000   30.0000 96

 12 omega  -77.00  -48.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000   30.0000 29

 13 omega  -90.00  -58.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -19.0000  -30.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0220544000
_diffrn_orient_matrix_UB_12      -0.0685583000
_diffrn_orient_matrix_UB_13      0.0025845000
_diffrn_orient_matrix_UB_21      -0.0118695000
_diffrn_orient_matrix_UB_22      0.0125675000
_diffrn_orient_matrix_UB_23      0.0581660000
_diffrn_orient_matrix_UB_31      -0.0953374000
_diffrn_orient_matrix_UB_32      0.0083756000
_diffrn_orient_matrix_UB_33      -0.0255774000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9208
_diffrn_reflns_theta_full        29.20
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         4.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0391P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2820
_reflns_number_total             3903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502446k_si_002.cif
_cod_data_source_block           hsp-av-iii-181
_cod_depositor_comments          'Adding full bibliography for 4030563.cif.'
_cod_original_cell_volume        837.77(11)
_cod_database_code               4030563
_chemical_oxdiff_formula         'C21 H16 N2 O3'
_chemical_oxdiff_usercomment     '298K, COLORLESS BLOCK, 0.5 0.4 0.25'
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32