Enantioselective one-pot synthesis of dihydroquinolones via BINOL-derived Lewis acid catalysis.
Knipe, Peter C.; Smith, Martin D.; Organic & biomolecular chemistry 12 (2014) 5094–5097; doi:10.1039/c4ob00627e

data_7153913
_publ_section_title
;
 Enantioselective one-pot synthesis of dihydroquinolones via BINOL-derived
 Lewis acid catalysis.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5094
_journal_page_last               5097
_journal_paper_doi               10.1039/c4ob00627e
_journal_volume                  12
_journal_year                    2014
_chemical_compound_source        syn
_chemical_formula_moiety         'C18 H19 Cl1 N2 O3'
_chemical_formula_sum            'C18 H19 Cl N2 O3'
_chemical_formula_weight         346.81
_chemical_melting_point          'see SI'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2014-02-01
_audit_creation_method           CRYSTALS_ver_14.43
_cell_angle_alpha                90
_cell_angle_beta                 98.3672(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5878(2)
_cell_length_b                   9.3875(2)
_cell_length_c                   14.5609(3)
_cell_measurement_reflns_used    7088
_cell_measurement_temperature    150
_cell_measurement_theta_max      1
_cell_measurement_theta_min      1
_cell_volume                     1702.32(6)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.028
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29097
_diffrn_reflns_theta_full        27.483
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.000
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.91
_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    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9508
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.0003402
_refine_ls_shift/su_mean         0.0000371
_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: 
 47.6 77.7 46.4 18.9 3.99 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1104
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1104
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3029
_reflns_number_total             3898
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      1.67
_oxford_refine_ls_r_factor_ref   0.0572
_oxford_refine_ls_scale          0.6339(15)
_oxford_reflns_number_all        3888
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 016RWD12
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 153,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 163,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) H   (   2,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c4ob00627e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 

 Adding full bibliography for 7153913.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C18 H19 Cl1 N2 O3'
_cod_database_code               7153913