Highly enantioselective synthesis of spirocyclopropyloxindoles via a Rh(ii)-catalyzed asymmetric cyclopropanation reaction.
Chi, Yongjian; Qiu, Lihua; Xu, Xinfang; Organic & biomolecular chemistry 14 (2016) 10357–10361; doi:10.1039/c6ob02160c

data_7155323
_publ_section_title
;
 Highly enantioselective synthesis of spirocyclopropyloxindoles via a
 Rh(ii)-catalyzed asymmetric cyclopropanation reaction.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10357
_journal_page_last               10361
_journal_paper_doi               10.1039/c6ob02160c
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H24 Cl N O4'
_chemical_formula_sum            'C23 H24 Cl N O4'
_chemical_formula_weight         413.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-16
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-19 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.156(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0330(5)
_cell_length_b                   9.8048(7)
_cell_length_c                   12.0153(7)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      26.0920
_cell_measurement_theta_min      3.4870
_cell_volume                     1064.15(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -48.00   60.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -19.0000   60.0000 108

  2 omega  -18.00    8.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -37.0000  -60.0000 26

  3 omega   -2.00   62.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   77.0000    0.0000 64

  4 omega  -22.00   14.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000   90.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0409883000
_diffrn_orient_matrix_UB_12      0.0135299000
_diffrn_orient_matrix_UB_13      0.0490333000
_diffrn_orient_matrix_UB_21      0.0210311000
_diffrn_orient_matrix_UB_22      -0.0644173000
_diffrn_orient_matrix_UB_23      0.0217211000
_diffrn_orient_matrix_UB_31      0.0636113000
_diffrn_orient_matrix_UB_32      0.0300422000
_diffrn_orient_matrix_UB_33      0.0246197000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5344
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.817
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0436P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.504
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                2690
_reflns_number_total             3006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02160c2.cif
_cod_data_source_block           g160416c
_cod_depositor_comments
'Adding full bibliography for 7155321--7155323.cif.'
_cod_original_cell_volume        1064.15(12)
_cod_database_code               7155323
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              89196
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-16
_olex2_submission_special_instructions 'No special instructions were received'