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_7150182
_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         'C8 H12 F6 N2 O4 S2, C1.80'
_chemical_formula_sum            'C9.8 H12 F6 N2 O4 S2'
_chemical_formula_weight         397.43
_chemical_name_systematic
;
(S,S) C,C,C-Trifluoro-N-(2-trifluoromethanesulfonylamino-cyclohexyl)
-methanesulfonamide
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.3841(2)
_cell_length_b                   14.3841(2)
_cell_length_c                   13.9800(4)
_cell_measurement_reflns_used    5844
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      2.83
_cell_volume                     2504.97(9)
_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 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
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_diffrn_reflns_av_R_equivalents  0.081
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_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24180
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_diffrn_reflns_theta_full        32.96
_diffrn_reflns_theta_max         32.96
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   none
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             1209.2
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_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.88(8)
_refine_diff_density_min         -0.60(8)
_refine_ls_abs_structure_details
; The least squares refinement included a factor according to Rogers (1981).
5312 significant reflections were used, including 2288 Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers  0.79(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    3
_refine_ls_number_parameters     215
_refine_ls_number_reflns         5312
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.0043
_refine_ls_shift/su_mean         0.0003
_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 = 0.03 and B = 0.0
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.036
_reflns_number_gt                5312
_reflns_number_total             6270
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b505220c.txt
_cod_data_source_block           wei-4d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 22 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

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

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

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

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

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

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/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_original_sg_symbol_Hall     'P 32 2'
_cod_original_formula_sum        'C9.80 H12 F6 N2 O4 S2'
_cod_database_code               7150182