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_1517665
_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         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-03
_audit_creation_method
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.75713(16)
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_cell_length_c                   13.1649(2)
_cell_measurement_reflns_used    8718
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      32.0060
_cell_measurement_theta_min      3.5220
_cell_volume                     1743.89(5)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_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 0.998
_diffrn_measurement_details
;
  1 omega  -98.00   48.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740    0.0000 -180.0000 146

  2 omega -102.00  -34.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0740  178.0000    0.0000 68

  3 omega   35.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802  178.0000    0.0000 67

  4 omega   -4.00   97.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   77.0000 -180.0000 101

  5 omega   35.00   74.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802  178.0000   90.0000 39

  6 omega    6.00   95.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   57.0000   60.0000 89
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_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
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_diffrn_orient_matrix_UB_11      -0.0010981000
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_diffrn_orient_matrix_UB_13      0.0489099000
_diffrn_orient_matrix_UB_21      -0.0558254000
_diffrn_orient_matrix_UB_22      -0.0305548000
_diffrn_orient_matrix_UB_23      -0.0287482000
_diffrn_orient_matrix_UB_31      0.0644702000
_diffrn_orient_matrix_UB_32      -0.0267659000
_diffrn_orient_matrix_UB_33      -0.0005228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20689
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.1835
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1458
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0496
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+1.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4423
_reflns_number_total             5098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5024129_si_002.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 1517665--1517670.cif.'
_cod_database_code               1517665
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C21 H22 N2 O3'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'