Cascade reaction involving Diels–Alder cascade: modular synthesis of amino α-pyrones, indolines and anilines
Shen, Yangyong; Wang, Chaorong; Chen, Wei; Cui, Sunliang; Organic Chemistry Frontiers 5 (2018) 3574–; doi:10.1039/C8QO00939B

data_1554469
_publ_section_title
;
 Cascade reaction involving Diels--Alder cascade: modular synthesis of
 amino \a-pyrones, indolines and anilines
;
_journal_issue                   24
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3574
_journal_paper_doi               10.1039/C8QO00939B
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C33 H26 Cl N O2 S'
_chemical_formula_sum            'C33 H26 Cl N O2 S'
_chemical_formula_weight         536.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-22
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2018-03-22 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.660(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2302(8)
_cell_length_b                   24.9417(18)
_cell_length_c                   10.5320(7)
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3114
_cell_measurement_theta_min      3.0029
_cell_volume                     2678.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -41.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  101.0000 -151.0000 56

  2 omega  -11.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000    0.0000 60

  3 omega  -11.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  120.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0335795000
_diffrn_orient_matrix_UB_12      -0.0247886000
_diffrn_orient_matrix_UB_13      -0.0032253000
_diffrn_orient_matrix_UB_21      -0.0546517000
_diffrn_orient_matrix_UB_22      -0.0109896000
_diffrn_orient_matrix_UB_23      -0.0368037000
_diffrn_orient_matrix_UB_31      0.0269068000
_diffrn_orient_matrix_UB_32      0.0085789000
_diffrn_orient_matrix_UB_33      -0.0565761000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11836
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.6266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3528
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00939b2.cif
_cod_data_source_block           180321_syy_11_77_a
_cod_database_code               1554469
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N S Cl'
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.59
_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.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C29(H29), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              67581
_shelx_hkl_checksum              71447
_olex2_submission_special_instructions 'No special instructions were received'