Construction of Tetrahydropyranoquinoline Derivatives via an Asymmetric Organocatalytic aza-Michael-IED/HAD Cascade Reaction
Dai, Lu; Hou, Yuxuan; Zhang, Lvye; Chen, Zhangtao; Zeng, Xiaofei; Zhong, Guofu; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02231J

data_7155923
_publ_section_title
;
 Construction of Tetrahydropyranoquinoline Derivatives via an Asymmetric
 Organocatalytic aza-Michael-IED/HAD Cascade Reaction
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02231J
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H26 Br N O6 S, 2.5(C H Cl3)'
_chemical_formula_sum            'C30.5 H28.5 Br Cl7.5 N O6 S'
_chemical_formula_weight         882.89
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-16 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.783(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6708(8)
_cell_length_b                   24.094(2)
_cell_length_c                   15.4897(14)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.27
_cell_volume                     3605.0(5)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18305
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_T_max  0.5333
_exptl_absorpt_correction_T_min  0.5333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1780
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.097(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     871
_refine_ls_number_reflns         18305
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+10.1732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                15829
_reflns_number_total             18305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02231j2.cif
_cod_data_source_block           pcm15s_0t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C30.50 H28.50 Br Cl7.50 N O6 S'
_cod_database_code               7155923