Catalytic Enantioselective Aza-Diels-Alder Reactions of Unactivated Acyclic 1,3-Dienes with Aryl-, Alkenyl-, and Alkyl-Substituted Imines
Hatanaka, Yasuo; Nantaku, Shuuto; Nishimura, Yuhki; Otsuka, Tomoyuki; Sekikawa, Tohru; Chem. Commun.  (2017) –; doi:10.1039/C7CC03010J

data_7120478
_publ_section_title
;
 Catalytic Enantioselective Aza-Diels-Alder Reactions of Unactivated
 Acyclic 1,3-Dienes with Aryl-, Alkenyl-, and Alkyl-Substituted Imines
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03010J
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 Cl N O2 S'
_chemical_formula_sum            'C19 H20 Cl N O2 S'
_chemical_formula_weight         361.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_block_doi                 10.5517/ccdc.csd.cc1mm7t9
_audit_creation_date             2016-10-4
_audit_creation_method
'generated by ACTA instruction via SHELXL-2014/7'
_audit_update_record
;
2016-10-04 deposited with the CCDC.
2017-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4650(11)
_cell_length_b                   10.6780(10)
_cell_length_c                   16.0955(17)
_cell_measurement_reflns_used    8193
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.4662
_cell_measurement_theta_min      3.1698
_cell_volume                     1798.6(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 7.32
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -80.0000 - 100.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Phi
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 35.1706
              2theta: 9.7913
scan:
    Number of images: 100
               Slice: -30.0000 - 20.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 90.0000
                 Phi: 0.0000
                 XTD: 35.1706
              2theta: 9.7913
scan:
    Number of images: 100
               Slice: -30.0000 - 20.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 90.0000
                 Phi: 90.0000
                 XTD: 35.1706
              2theta: 9.7913
scan:
    Number of images: 100
               Slice: -30.0000 - 20.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 90.0000
                 Phi: 180.0000
                 XTD: 35.1706
              2theta: 9.7913

;
_diffrn_measurement_device       'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_device_details 'AFC7: Eulerian 3-circle'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17245
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         3.170
_diffrn_source_current           250.0000
_diffrn_source_power             15.0000
_diffrn_source_voltage           60.0000
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_preparation
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0580P)^2^+0.0138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3866
_reflns_number_total             4049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03010j2.cif
_cod_data_source_block           Compound_3ai
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7120478
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.905
_shelx_res_checksum              15499