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_1517669
_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         'C25 H26 N2 O4'
_chemical_formula_sum            'C25 H26 N2 O4'
_chemical_formula_weight         418.48
_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'
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_measurement_reflns_used    4969
_cell_measurement_temperature    110.05(10)
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_computing_cell_refinement
'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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'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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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_13      -0.0251132000
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_diffrn_orient_matrix_UB_22      -0.0475678000
_diffrn_orient_matrix_UB_23      0.0202766000
_diffrn_orient_matrix_UB_31      -0.0793238000
_diffrn_orient_matrix_UB_32      0.0053913000
_diffrn_orient_matrix_UB_33      0.0077850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
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_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12044
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'SuperNova (Mo) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
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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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description
;
;
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3168
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.1447
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         6343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0433
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.7492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1138
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_reflns_number_gt                5343
_reflns_number_total             6343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5024129_si_002.cif
_cod_data_source_block           dl-12a
_cod_depositor_comments
'Adding full bibliography for 1517665--1517670.cif.'
_cod_database_code               1517669
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C25 H26 N2 O4'
_chemical_oxdiff_usercomment     'Tim TEH162'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C7(H7), C4(H4), C5(H5), C19(H19), C6(H6), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C24(H24A,H24B,
 H24C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;