Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones
Ren, Xiao-Rui; Lin, Jun-Bing; Hu, Xiu-Qin; Xu, Peng-Fei; Organic Chemistry Frontiers 6 (2019) 2280–; doi:10.1039/C9QO00357F

data_1554886
_publ_section_title
;
 Bifunctional Br\/onsted base catalyzed inverse-electron-demand
 aza-Diels--Alder reactions of saccharin-derived 1-azadienes with
 azlactones
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2280
_journal_paper_doi               10.1039/C9QO00357F
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H26 N2 O5 S, C H Cl3'
_chemical_formula_sum            'C33 H27 Cl3 N2 O5 S'
_chemical_formula_weight         669.98
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-25 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9357(5)
_cell_length_b                   11.7723(6)
_cell_length_c                   24.8931(9)
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7800
_cell_measurement_theta_min      3.7640
_cell_volume                     3204.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -15.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   60.0000 37

  2 omega   -1.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 41

  3 omega   -9.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  -60.0000 25

  4 omega   51.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  -60.0000 37

  5 omega  -50.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  120.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0096872000
_diffrn_orient_matrix_UB_12      -0.0595708000
_diffrn_orient_matrix_UB_13      -0.0001893000
_diffrn_orient_matrix_UB_21      -0.0574620000
_diffrn_orient_matrix_UB_22      -0.0082581000
_diffrn_orient_matrix_UB_23      0.0126209000
_diffrn_orient_matrix_UB_31      -0.0284677000
_diffrn_orient_matrix_UB_32      -0.0036601000
_diffrn_orient_matrix_UB_33      -0.0255486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12469
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6210
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.6295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                4721
_reflns_number_total             6210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00357f2.cif
_cod_data_source_block           renxr_0709
_cod_database_code               1554886
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl3B) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl1B) \\sim Ueq, Uanis(Cl2)
\\sim Ueq, Uanis(Cl2B) \\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: Cl1(0.5) Cl3(0.5) Cl2(0.5) H33A(0.5) H33(0.5) Cl1B(0.5) Cl2B(0.5)
 Cl3B(0.5)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C33(H33A), C33(H33)
4.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C25(H25), C4(H4), C14(H14), C32(H32), C24(H24), C21(H21),
 C17(H17), C15(H15), C31(H31), C1(H1), C22(H22), C30(H30), C23(H23), C29(H29),
 C2(H2A), C3(H3), C16(H16)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2018-07-09
_olex2_submission_special_instructions 'No special instructions were received'