Cation-directed enantioselective synthesis of quaternary-substituted indolenines
Li, Meiling; Woods, Philip A.; Smith, Martin D.; Chemical Science 4 (2013) 2907–; doi:10.1039/c3sc50592h

data_1514506
_publ_section_title
;
 Cation-directed enantioselective synthesis of quaternary-substituted
 indolenines
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              2907
_journal_paper_doi               10.1039/c3sc50592h
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C26 H19 Br1 N2 O2 S1'
_chemical_formula_sum            'C26 H19 Br N2 O2 S'
_chemical_formula_weight         503.42
_chemical_melting_point          'see supporting information'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-08-12
_audit_creation_method           CRYSTALS_ver_14.23
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.61820(10)
_cell_length_b                   12.42540(10)
_cell_length_c                   20.8694(2)
_cell_measurement_reflns_used    2909
_cell_measurement_temperature    150
_cell_measurement_theta_max      1
_cell_measurement_theta_min      1
_cell_volume                     2234.79(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5078
_diffrn_reflns_theta_full        26.954
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         5.103
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.79
_refine_ls_abs_structure_details 'Flack (1983), 2190 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9781
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.0003645
_refine_ls_shift/su_mean         0.0000199
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
41.8 70.1 44.8 20.1 5.07
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0804
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0804
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                4362
_reflns_number_total             5078
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.50
_oxford_diffrn_Wilson_scale      9.30
_oxford_refine_ls_r_factor_ref   0.0522
_oxford_refine_ls_scale          0.3364(3)
_oxford_reflns_number_all        5078
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 024RWD12
_cod_data_source_file            c3sc50592h.txt
_cod_data_source_block           publication_text
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C26 H19 Br1 N2 O2 S1'
_cod_database_code               1514506
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT ENANTIO
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 27,X'S) H ( 271,X'S)
RIDE C ( 28,X'S) H ( 283,X'S) H ( 281,X'S) H ( 282,X'S)
RIDE C ( 31,X'S) H ( 311,X'S)
RIDE C ( 32,X'S) H ( 321,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;