Highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides
Guan, Xiao-Yu; Tang, Min; Liu, Zhang-Qin; Hu, WenHao; Chemical Communications  (2019) –; doi:10.1039/C9CC04890A

data_7123901
_publ_section_title
;
 Highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted
 tetrahydroquinoxalines via intramolecular Mannich-type trapping of
 ammonium ylides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04890A
_journal_year                    2019
_chemical_formula_sum            'C26 H26 N4 O9'
_chemical_formula_weight         538.51
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-02-21 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                97.079(3)
_cell_angle_beta                 99.017(3)
_cell_angle_gamma                105.178(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9231(9)
_cell_length_b                   12.3032(12)
_cell_length_c                   14.0647(13)
_cell_measurement_reflns_used    7842
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.04
_cell_volume                     1287.3(2)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12625
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.1088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1360P)^2^+13.8960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3702
_refine_ls_wR_factor_ref         0.3790
_reflns_number_gt                4310
_reflns_number_total             5851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc04890a2.cif
_cod_data_source_block           y2455
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7123901