Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.
Shu, Tao; Ni, Qijian; Song, Xiaoxiao; Zhao, Kun; Wu, Tianyu; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter; Chemical communications (Cambridge, England) 52 (2016) 2609–2611; doi:10.1039/c5cc09581f

data_7118330
_publ_section_title
;
 Asymmetric synthesis of cyclopentanes bearing four contiguous
 stereocenters via an NHC-catalyzed Michael/Michael/esterification domino
 reaction.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2609
_journal_page_last               2611
_journal_paper_doi               10.1039/c5cc09581f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 Cl N O6'
_chemical_formula_sum            'C21 H20 Cl N O6'
_chemical_formula_weight         417.83
_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
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.79637(17)
_cell_length_b                   13.3106(3)
_cell_length_c                   25.2934(6)
_cell_measurement_reflns_used    5810
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.2460
_cell_measurement_theta_min      4.7780
_cell_volume                     1951.47(9)
_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)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -40.00    9.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -120.0000 49

  2 omega  -64.00  -14.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  150.0000 50

  3 omega  -47.00   24.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  120.0000 71

  4 omega  -99.00  -73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  150.0000 26

  5 omega  -32.00   -1.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000  -60.0000 31

  6 omega  -60.00   -2.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000  -60.0000 58

  7 omega -122.00  -41.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000  -60.0000 81

  8 omega    9.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 58

  9 omega    1.00   54.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000  -60.0000 53

 10 omega   11.00  117.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000   60.0000 106

 11 omega   11.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  150.0000 103

 12 omega   80.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -30.0000 25

 13 omega   11.00   72.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -30.0000 61

 14 omega   43.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000  150.0000 55

 15 omega   74.00  174.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -90.0000 100

 16 omega   78.00  105.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 27

 17 omega   24.00  104.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -30.0000 80

 18 omega   24.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   60.0000 72

 19 omega   74.00  172.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 98

 20 omega   78.00  174.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -120.0000 96

 21 omega   77.00  103.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   62.0000 -176.8667 26

 22 omega   80.00  129.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 49

 23 omega   36.00   86.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -150.0000 50

 24 omega   78.00  104.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -60.0000 26

 25 omega   74.00  100.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -150.0000 26

 26 omega   33.00  116.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -60.0000 83

 27 omega   81.00   85.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -30.0000 4
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2525942000
_diffrn_orient_matrix_UB_12      -0.0061741000
_diffrn_orient_matrix_UB_13      0.0186570000
_diffrn_orient_matrix_UB_21      -0.0799934000
_diffrn_orient_matrix_UB_22      -0.0094520000
_diffrn_orient_matrix_UB_23      -0.0579010000
_diffrn_orient_matrix_UB_31      0.0199832000
_diffrn_orient_matrix_UB_32      -0.1151414000
_diffrn_orient_matrix_UB_33      0.0037477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.737
_diffrn_reflns_theta_min         3.495
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95169
_exptl_absorpt_correction_type   gaussian
_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.
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    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.0579
_exptl_crystal_size_mid          0.0409
_exptl_crystal_size_min          0.0215
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0334P)^2^+0.0389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3089
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09581f2.cif
_cod_data_source_block           3h
_cod_depositor_comments          'Adding full bibliography for 7118330.cif.'
_cod_database_code               7118330
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N1 O1'
_reflns_odcompleteness_completeness 99.71
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              12149
_olex2_submission_special_instructions 'No special instructions were received'