Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double C-H, Ar-H Coupling Process.
Drouhin, Pauline; Hurst, Timothy E.; Whitwood, Adrian C.; Taylor, Richard J. K.; Organic letters 16 (2014) 4900–4903; doi:10.1021/ol5024129

data_1517667
_publ_section_title
;
 Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double
 C-H, Ar-H Coupling Process.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4900
_journal_page_last               4903
_journal_paper_doi               10.1021/ol5024129
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C22 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.41
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.448(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7526(3)
_cell_length_b                   16.2826(7)
_cell_length_c                   14.5413(8)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      30.0470
_cell_measurement_theta_min      3.3680
_cell_volume                     1823.97(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details
;
  1 omega  -97.00  -35.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -      -20.6164 -178.0000  -60.0000 62

  2 omega    1.00   91.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1789   57.0000 -120.0000 90

  3 omega  -20.00   64.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1789  -99.0000  -30.0000 84

  4 omega   -8.00   92.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1789   77.0000  150.0000 100

  5 omega   -4.00   21.00   1.0000   24.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1789   37.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0239232000
_diffrn_orient_matrix_UB_12      0.0367273000
_diffrn_orient_matrix_UB_13      -0.0244221000
_diffrn_orient_matrix_UB_21      0.0112239000
_diffrn_orient_matrix_UB_22      -0.0198816000
_diffrn_orient_matrix_UB_23      -0.0423254000
_diffrn_orient_matrix_UB_31      -0.0882241000
_diffrn_orient_matrix_UB_32      -0.0123966000
_diffrn_orient_matrix_UB_33      -0.0044992000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14503
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.350
_diffrn_reflns_theta_min         2.819
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.1956
_exptl_crystal_size_mid          0.0941
_exptl_crystal_size_min          0.0393
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0928
_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^)+(0.0632P)^2^+3.0616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2096
_reflns_number_total             4976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5024129_si_002.cif
_cod_data_source_block           trans-10
_cod_depositor_comments
'Adding full bibliography for 1517665--1517670.cif.'
_cod_database_code               1517667
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C22 H22 N2 O3'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C21 \\sim N2A-C22A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(O1) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N1) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C21) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C9) = Uanis(C20A)
Uanis(C20) = Uanis(C9A)
Uanis(C8) = Uanis(C12A)
Uanis(O1A) = Uanis(O3)
Uanis(C7A) = Uanis(C13)
Uanis(N1A) = Uanis(N2)
Uanis(C21A) = Uanis(C22)
Uanis(C12) = Uanis(C8A)
Uanis(N1) = Uanis(N2A)
Uanis(C13A) = Uanis(C7)
Uanis(O3A) = Uanis(O1)
Uanis(C21) = Uanis(C22A)
4. Others
 Fixed Sof: C7A(0.5) C8A(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) C10A(0.5) H10D(0.5)
 H10E(0.5) H10F(0.5) C11A(0.5) C12A(0.5) C13A(0.5) C20A(0.5) H20D(0.5)
 H20E(0.5) H20F(0.5) C21A(0.5) H21D(0.5) H21E(0.5) H21F(0.5) C22A(0.5)
 H22D(0.5) H22E(0.5) H22F(0.5) N1(0.5) N1A(0.5) N2A(0.5) O1A(0.5) O2A(0.5)
 O3A(0.5) O3(0.5) O2(0.5) O1(0.5) N2(0.5) C10(0.5) H10A(0.5) H10B(0.5)
 H10C(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C11(0.5) C21(0.5) H21A(0.5)
 H21B(0.5) H21C(0.5) C8(0.5) C7(0.5) C13(0.5) C12(0.5) C20(0.5) H20A(0.5)
 H20B(0.5) H20C(0.5) C9(0.5) H9A(0.5) H9B(0.5)
 Fixed U11: C13A(0.01513) C7(0.01513)
5.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C10A(H10D,H10E,H10F), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F), C22A(H22D,
 H22E,H22F), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C),
 C20(H20A,H20B,H20C)
;