Iron(II)-Catalyzed Asymmetric Intramolecular Aminohydroxylation of Indoles.
Zhang, Yong-Qiang; Yuan, Yong-An; Liu, Guan-Sai; Xu, Hao; Organic letters 15 (2013) 3910–3913; doi:10.1021/ol401666e

data_1512199
_publ_section_title
;
 Iron(II)-Catalyzed Asymmetric Intramolecular Aminohydroxylation of
 Indoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3910
_journal_page_last               3913
_journal_paper_doi               10.1021/ol401666e
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H16 Cl2 N2 O6 S, C3 H6 O'
_chemical_formula_sum            'C26 H22 Cl2 N2 O7 S'
_chemical_formula_weight         577.41
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2012-11-29
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Nov  5 2012 18:25:38, GUI svn.r4372)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6790(7)
_cell_length_b                   11.8883(8)
_cell_length_c                   22.4824(16)
_cell_measurement_reflns_used    6908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      2.49
_cell_volume                     2587.0(3)
_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
;
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      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20608
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.579
_diffrn_reflns_theta_min         1.812
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0668 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.7807.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.698
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 2730 quotients [(I+)-I(-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.012(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.5565P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6840
_reflns_number_total             7834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol401666e_si_002.cif
_cod_data_source_block           b302_0m
_cod_database_code               1512199
_diffrn_reflns_sigmai/neti       0.0384
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1A of C1, H16 of C16, {H11A,H11B} of C11, H19 of C19, H13 of C13, H23 of
  C23, H22 of C22, H14 of C14, H15 of C15, H8 of C8, H4 of C4, H2 of C2, H21 of
  C21, H20 of C20
 At 1.5 times of:
  {H26A,H26B,H26C} of C26, {H24A,H24B,H24C} of C24
2. Restrained distances
 N1-H1
 0.99 with sigma of 0.005
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C1(H1A), C16(H16), C19(H19), C13(H13), C23(H23), C22(H22),
 C14(H14), C15(H15), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C)
;
_shelx_hkl_checksum              28381
_shelx_res_checksum              94058
_shelxl_version_number           2012-4