Catalytic Asymmetric Synthesis of Pyrroloindolines via a Rhodium(II)-Catalyzed Annulation of Indoles
Jillian E. Spangler; Huw M. L. Davies; Journal of the American Chemical Society 135 (2013) 6802–6805; doi:10.1021/ja4025337

data_4119733
_publ_contact_author_name
;
;
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Pyrroloindolines via a
 Rhodium(II)-Catalyzed Annulation of Indoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6802
_journal_page_last               6805
_journal_paper_doi               10.1021/ja4025337
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C19 H22 N2 O2 S'
_chemical_formula_sum            'C19 H22 N2 O2 S'
_chemical_formula_weight         342.44
_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     iterative
_audit_creation_date             2013-02-25
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_audit_update_record
;
2013-02-25 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.70930(10)
_cell_length_b                   8.8356(2)
_cell_length_c                   28.7168(7)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      38.642
_cell_measurement_theta_min      2.412
_cell_volume                     1702.35(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            35040
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.642
_diffrn_reflns_theta_min         1.418
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.4485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.5999.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.752
_exptl_crystal_size_mid          0.542
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.039(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.553
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         8910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.028
_refine_ls_R_Fsqd_factor         0.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.029
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                9080
_reflns_number_total             9599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4025337_si_003.cif
_cod_data_source_block           jes412701
_cod_database_code               4119733
_shelxl_version_number           2012-9