Asymmetric Synthesis of Cyclopenta[3,4]pyrroloindolones via N-Heterocyclic Carbene-Catalyzed Michael/Aldol/Lactamization Cascade Reaction.
Yang, Yu-Jie; Ji, Yuanyuan; Qi, Liangliang; Wang, Guanjun; Hui, Xin-Ping; Organic letters 19 (2017) 3271–3274; doi:10.1021/acs.orglett.7b01411

data_1546474
_publ_section_title
;
 Asymmetric Synthesis of Cyclopenta[3,4]pyrroloindolones via
 N-Heterocyclic Carbene-Catalyzed Michael/Aldol/Lactamization Cascade
 Reaction.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3271
_journal_page_last               3274
_journal_paper_doi               10.1021/acs.orglett.7b01411
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H23 N O3'
_chemical_formula_sum            'C27 H23 N O3'
_chemical_formula_weight         409.46
_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             2015-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.24343(13)
_cell_length_b                   16.3321(3)
_cell_length_c                   20.2668(4)
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    293.42(10)
_cell_measurement_theta_max      69.8770
_cell_measurement_theta_min      4.3540
_cell_volume                     2066.57(7)
_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)
;
_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)
;
_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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega   13.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   81.0000   29.0000 33

  2 omega   41.00  117.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 76

  3 omega   37.00   93.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 56

  4 omega   63.00   90.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 27

  5 omega   45.00   77.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 32

  6 omega   43.00   69.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 26

  7 omega   39.00   67.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 28

  8 omega   44.00  131.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 87

  9 omega   59.00  116.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 57

 10 omega   37.00   89.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 52

 11 omega   -4.00   68.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 72

 12 omega   77.00  118.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 41

 13 omega  104.00  176.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 72

 14 omega  -11.00   43.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 54

 15 omega  -15.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -81.0000  -93.0000 25

 16 omega  -13.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 25

 17 omega  -21.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   81.0000   29.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0738319000
_diffrn_orient_matrix_UB_12      0.0693339000
_diffrn_orient_matrix_UB_13      0.0464118000
_diffrn_orient_matrix_UB_21      -0.1104368000
_diffrn_orient_matrix_UB_22      -0.0430588000
_diffrn_orient_matrix_UB_23      0.0584170000
_diffrn_orient_matrix_UB_31      0.2077201000
_diffrn_orient_matrix_UB_32      -0.0474426000
_diffrn_orient_matrix_UB_33      0.0145170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.731
_diffrn_reflns_theta_min         5.417
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17258
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(16)
_refine_ls_extinction_coef       0.0061(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0441P)^2^+0.2205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0961
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_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3489
_reflns_number_total             3825
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_cod_data_source_file            ol7b01411_si_002.cif
_cod_data_source_block           yangyj0413
_cod_database_code               1546474
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a), C3(H3), C4(H4), C5(H5), C7(H7), C16(H16), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-13
_olex2_submission_special_instructions 'No special instructions were received'