Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst–synthesis of optically active tetrahydro-beta-carbolines.
Zhuang, Wei; Hazell, Rita G.; Jørgensen, Karl Anker; Organic & biomolecular chemistry 3 (2005) 2566–2571; doi:10.1039/b505220c

data_7150183
_publ_section_title
;
 Enantioselective Friedel-Crafts type addition of indoles to
 nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of
 optically active tetrahydro-beta-carbolines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2566
_journal_page_last               2571
_journal_paper_doi               10.1039/b505220c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C16 H14 F6 N2 O4 S2'
_chemical_formula_sum            'C16 H14 F6 N2 O4 S2'
_chemical_formula_weight         476.42
_chemical_name_systematic
;
(R,R) N-(1,2-Diphenyl-2-trifluoromethanesulfonylamino-ethyl)-
C,C,C-trifluoro-methanesulfonamide
;
_space_group_IT_number           179
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65 2 (0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 2'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                120.000
_cell_formula_units_Z            12
_cell_length_a                   11.6353(10)
_cell_length_b                   11.6353(10)
_cell_length_c                   52.806(9)
_cell_measurement_reflns_used    7007
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      3.07
_cell_volume                     6191.1(13)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'scans with narrow frames '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.107
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -66
_diffrn_reflns_number            62518
_diffrn_reflns_reduction_process 62518
_diffrn_reflns_theta_full        20.82
_diffrn_reflns_theta_max         28.14
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.8(1)
_refine_diff_density_min         -1.1(1)
_refine_ls_abs_structure_details
; The least squares refinement included a factor according to Rogers (1981).
4303 significant reflections were used, including 1598 Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers  1.02(24)
_refine_ls_extinction_coef       1396(144)
_refine_ls_extinction_method
;
Type 1 Lorentzian isotropic (Becker and Coppens, 1974)
;
_refine_ls_goodness_of_fit_ref   1.70
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.00005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.05 and B = 0.25
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.081
_reflns_number_gt                4303
_reflns_number_total             5027
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            b505220c.txt
_cod_data_source_block           wei-4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
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Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:
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data
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data
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data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
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'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
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'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_database_code               7150183