Rapid Assembly of Cyclopentene Spiroisoindolinones via Rhodium-Catalysed Redox-Neutral Cascade Reaction
Yuan, Tingting; Pi, Chao; You, Chang; Cui, Xiuling; Du, Sidong; Wan, Ting; Wu, Yangjie; Chemical Communications  (2018) –; doi:10.1039/C8CC08081J

data_7122529
_publ_section_title
;
 Rapid Assembly of Cyclopentene Spiroisoindolinones via Rhodium-Catalysed
 Redox-Neutral Cascade Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08081J
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H17 N O'
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-04-10 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.92466(18)
_cell_length_b                   11.5149(3)
_cell_length_c                   19.0209(6)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.5090
_cell_measurement_theta_min      4.4760
_cell_volume                     1735.69(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -49.00   37.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 172

  2 omega  -57.00  -31.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 52

  3 omega  -21.00   36.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 114

  4 omega  -29.00   -3.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 52

  5 omega   58.00   84.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 52

  6 omega   29.00   64.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 70

  7 omega    6.00   71.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 130

  8 omega  -33.00   -7.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 52

  9 omega    1.00   56.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 110

 10 omega   42.00   95.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 106

 11 omega   49.00   75.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 52

 12 omega   51.00   89.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 76

 13 omega   80.00  107.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 54

 14 omega   42.00   98.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 112

 15 omega   42.00  105.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 126

 16 omega   54.00   84.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 60

 17 omega   39.00   98.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 118

 18 omega  100.00  126.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 52

 19 omega   42.00   85.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 86

 20 omega   59.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0173251000
_diffrn_orient_matrix_UB_12      -0.1331738000
_diffrn_orient_matrix_UB_13      -0.0013565000
_diffrn_orient_matrix_UB_21      -0.0492116000
_diffrn_orient_matrix_UB_22      0.0051782000
_diffrn_orient_matrix_UB_23      -0.0782612000
_diffrn_orient_matrix_UB_31      0.1874055000
_diffrn_orient_matrix_UB_32      -0.0110506000
_diffrn_orient_matrix_UB_33      -0.0207356000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6178
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.489
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.237
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0710
_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^)+(0.1023P)^2^+0.4655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2553
_reflns_number_total             3109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08081j2.cif
_cod_data_source_block           20170316
_cod_original_cell_volume        1735.69(9)
_cod_database_code               7122529
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N2
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C9-C18A
 2.2 with sigma of 0.02
3. Rigid bond restraints
 C11, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
5. Others
 Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=
 Sof(H21)=Sof(C22)=Sof(H22)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
6.b Fitted hexagon refined as free rotating group:
 C17(C18,C19,C20,C21,C22), C17A(C18A,C19A,C20A,C21A,C22A)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'