Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates.
Zhong, Sabilla; Nieger, Martin; Bihlmeier, Angela; Shi, Min; Bräse, Stefan; Organic & biomolecular chemistry 12 (2014) 3265–3270; doi:10.1039/c4ob00234b

data_7153745
_publ_section_title
;
 Asymmetric organocatalytic synthesis of
 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3265
_journal_page_last               3270
_journal_paper_doi               10.1039/c4ob00234b
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H29 N3 O2'
_chemical_formula_sum            'C30 H29 N3 O2'
_chemical_formula_weight         463.56
_chemical_name_systematic
;
 ethyl-4,6-di(1H-indol-3-yl)-1-phenylpiperidin-2-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
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_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
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2013-12-17 # Formatted by publCIF

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_cell_angle_alpha                62.398(9)
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_cell_length_b                   9.4665(9)
_cell_length_c                   9.6211(9)
_cell_measurement_reflns_used    8138
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.26
_cell_measurement_theta_min      5.26
_cell_volume                     626.45(12)
_computing_cell_refinement
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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)
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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)
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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)
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_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  publCif
_computing_structure_refinement
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SHELXL-2013 (Sheldrick, 2013)
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans, 2\%'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9604
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.554
_diffrn_reflns_theta_min         5.274
_diffrn_source
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SuperNova (Cu) X-ray Source
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_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.903
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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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plates
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Hooft's y parameter 0.02(5) (Hooft, Straver, Spek (2008), 
 J. Appl. Cryst. 46, 96-103).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0140(12)
_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   1.053
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0316P)^2^+0.1014P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                4736
_reflns_number_total             4786
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {1919ea22-7769-44af-93c9-dd92095895e6}
_cod_data_source_file            c4ob00234b2.cif
_cod_data_source_block           cu_sb632
_cod_depositor_comments          'Adding full bibliography for 7153745.cif.'
_cod_database_code               7153745
_shelx_estimated_absorpt_t_min   0.852
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2013-2
_shelx_res_checksum              20858