Bicyclic guanidinium-catalyzed enantioselective phase-transfer alkylation: direct access to pyrroloindolines and furoindolines
Wenchao Chen; Wenguo Yang; Lin Yan; Choon-Hong Tan; Zhiyong Jiang; Chem.Commun. 49 (2013) 9854–; doi:10.1039/c3cc46111d

data_7109906
_publ_section_title
;
 Bicyclic guanidinium-catalyzed enantioselective phase-transfer
 alkylation: direct access to pyrroloindolines and furoindolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              9854
_journal_paper_doi               10.1039/c3cc46111d
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'I, 0.5(H2 O), C13 H26 N3'
_chemical_formula_sum            'C13 H27 I N3 O0.5'
_chemical_formula_weight         360.27
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:06:00, GUI svn.r4456)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6885(2)
_cell_length_b                   16.3224(2)
_cell_length_c                   17.9468(3)
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.9527
_cell_measurement_theta_min      3.6574
_cell_volume                     3423.97(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -77.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 44

  2 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 25

  3 omega  -11.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 27

  4 omega  -49.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 62

  5 omega   -1.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000   90.0000 29

  6 omega  -48.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -60.0000 78

  7 omega   35.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 82

  8 omega   84.00  130.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 46

  9 omega   52.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 25

 10 omega  107.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 69

 11 omega   54.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 36

 12 omega  126.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 50

 13 omega   40.00  103.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 63

 14 omega   63.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 27

 15 omega   82.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 26

 16 omega   50.00   96.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 46

 17 omega   82.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 95

 18 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   90.0000 98

 19 omega   26.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0935006000
_diffrn_orient_matrix_UB_12      0.0231897000
_diffrn_orient_matrix_UB_13      -0.0566950000
_diffrn_orient_matrix_UB_21      -0.0591468000
_diffrn_orient_matrix_UB_22      0.0830943000
_diffrn_orient_matrix_UB_23      -0.0132170000
_diffrn_orient_matrix_UB_31      0.0715201000
_diffrn_orient_matrix_UB_32      0.0382916000
_diffrn_orient_matrix_UB_33      0.0631345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12579
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(8)
_refine_ls_extinction_coef       0.00117(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         6107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                5543
_reflns_number_total             6107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46111d.txt
_cod_data_source_block           20130441
_cod_original_cell_volume        3423.96(10)
_cod_database_code               7109906
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 I1(O1,H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C2'(H2'), C6(H6), C6'(H6')
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3'(H3'A,H3'B), C5(H5A,H5B), C5'(H5'A,H5'B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N1'(H1'), N3(H3), N3'(H3')
2.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8'(H8'A,H8'B,H8'C), C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C),
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F), C11(H11A,H11B,H11C), C11'(H11D,H11E,
 H11F), C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F), C13(H13A,H13B,H13C),
 C13'(H13D,H13E,H13F)
;