Dynamic kinetic asymmetric transfer hydrogenation-cyclization tandem reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles
Zheng, Dongsong; Zhao, Qiankun; Hu, Xiaoying; Cheng, Tanyu; Liu, Guohua; Wang, Wei; Chem. Commun.  (2017) –; doi:10.1039/C7CC02156A

data_7120119
_publ_section_title
;
 Dynamic kinetic asymmetric transfer hydrogenation-cyclization tandem
 reaction: an easy access to chiral 3,4-dihydro-2H-pyran-carbonitriles
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02156A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-10-30 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.1100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.1608(7)
_cell_length_b                   6.9059(2)
_cell_length_c                   21.9106(9)
_cell_measurement_reflns_used    3528
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      137.042
_cell_measurement_theta_min      8.164
_cell_volume                     3277.45(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7732
_diffrn_reflns_point_group_measured_fraction_full 0.663
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.485
_diffrn_reflns_theta_min         4.164
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
; 
 Flack x determined using 871 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0590P)^2^+1.3240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.324
_reflns_Friedel_fraction_full    0.357
_reflns_Friedel_fraction_max     0.378
_reflns_number_gt                3709
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02156a2.cif
_cod_data_source_block           dm15453
_cod_depositor_comments
;

2017-11-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C38 H36 N4 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     612.71
_cod_database_code               7120119
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.932
_shelxl_version_number           2013-4
_shelx_res_checksum              87294