Lewis Acid Catalyzed [4 + 2] Cycloaddition of <i>N</i>-Tosylhydrazones with <i>ortho</i>-Quinone Methides.
Wang, Chun-Ying; Han, Jia-Bin; Wang, Long; Tang, Xiang-Ying; The Journal of organic chemistry 84 (2019) 14258–14269; doi:10.1021/acs.joc.9b02040

data_4033611
_publ_section_title
;
 Lewis Acid Catalyzed [4 + 2] Cycloaddition of <i>N</i>-Tosylhydrazones
 with <i>ortho</i>-Quinone Methides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14258
_journal_page_last               14269
_journal_paper_doi               10.1021/acs.joc.9b02040
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H24 N2 O3 S'
_chemical_formula_sum            'C27 H24 N2 O3 S'
_chemical_formula_weight         456.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                109.332(2)
_cell_angle_beta                 95.5050(10)
_cell_angle_gamma                113.013(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1662(2)
_cell_length_b                   11.1972(2)
_cell_length_c                   13.2680(2)
_cell_measurement_reflns_used    20967
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5520
_cell_measurement_theta_min      3.6610
_cell_volume                     1142.22(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -33.00  30.00   0.50    0.50    --    0.00 -82.00-150.00  126
  2  \w      6.00  50.00   0.50    0.50    --   32.00  71.00-129.67   88
  3  \w     70.00 118.00   0.50    0.50    --   32.00  71.00-129.67   96
  4  \w      4.00  57.00   0.50    0.50    --   40.00 -44.00 -59.79  106
  5  \w    -45.00  -2.00   0.50    0.50    --   40.00 -44.00 -59.79   86
  6  \w     17.00  47.00   0.50    0.50    --   44.00  72.00 -65.75   60
  7  \w     67.00  95.00   0.50    0.50    --   44.00  72.00 -65.75   56
  8  \w     32.00  58.00   0.50    0.50    --   52.00  74.00  52.18   52
  9  \w     31.00  56.00   0.50    0.50    --   52.00  74.00 -44.64   50
 10  \w     28.00  54.00   0.50    0.50    --   52.00  73.00  22.69   52
 11  \w     29.00  59.00   0.50    0.50    --   56.00  72.00 103.19   60
 12  \w     29.00  54.00   0.50    0.50    --   56.00  72.00 -80.34   50
 13  \w    113.00 140.00   0.50    0.50    --   56.00  72.00 -80.34   54
 14  \w     32.00  73.00   0.50    0.50    --   60.00  74.00 131.10   82
 15  \w     37.00  66.00   0.50    0.50    --   64.00  73.00-133.68   58
 16  \w     36.00  66.00   0.50    0.50    --   64.00  74.00 171.35   60
 17  \w     93.00 118.00   0.50    0.50    --   64.00  74.00 171.35   50
 18  \w     36.00  67.00   0.50    0.50    --   64.00  75.00 -29.40   62
 19  \w     86.00 115.00   0.50    0.50    --   68.00  75.00  69.42   58
 20  \w     40.00  68.00   0.50    0.50    --   68.00  75.00  69.42   56
 21  \w    132.00 157.00   0.50    0.50    --   68.00  75.00  69.42   50
 22  \w     45.00  72.00   0.50    0.50    --   72.00  71.00  27.13   54
 23  \w    118.00 160.00   0.50    0.50    --   72.00  75.00 -15.01   84
 24  \w     45.00  71.00   0.50    0.50    --   72.00  75.00 -15.01   52
 25  \w     49.00  75.00   0.50    0.50    --   72.00  69.00  48.78   52
 26  \w     49.00  85.00   0.50    0.50    --   76.00  71.00-153.42   72
 27  \w     51.00  79.00   0.50    0.50    --   76.00  69.00 -58.97   56
 28  \w    108.00 165.00   0.50    0.50    --   76.00  74.00 -93.20  114
 29  \w     49.00  75.00   0.50    0.50    --   76.00  74.00 -93.20   52
 30  \w     48.00  74.00   0.50    0.50    --   76.00  74.00-179.14   52
 31  \w    123.00 151.00   0.50    0.50    --   76.00  74.00-179.14   56
 32  \w     84.00 115.00   0.50    0.50    --   76.00  74.00-179.14   62
 33  \w    124.00 152.00   0.50    0.50    --   80.00  68.00 -49.62   56
 34  \w     61.00  97.00   0.50    0.50    --   80.00  68.00 -49.62   72
 35  \w    105.00 152.00   0.50    0.50    --   80.00  66.00 123.07   94
 36  \w     55.00 100.00   0.50    0.50    --   80.00  66.00 123.07   90
 37  \w     59.00 108.00   0.50    0.50    --   84.00  68.00 145.18   98
 38  \w     92.00 117.00   0.50    0.50    --   94.60 -77.00  60.00   50
 39  \w     52.00  78.00   0.50    0.50    --   94.60 -82.00  90.00   52
 40  \w      6.00  71.00   0.50    0.50    --   94.60 -77.00  60.00  130
 41  \w      5.00 101.00   0.50    0.50    --   94.60 -61.00 -60.00  192
 42  \w    131.00 182.00   0.50    0.50    --   94.60  61.00-120.00  102
 43  \w     73.00 123.00   0.50    0.50    --   94.60  61.00-120.00  100
 44  \w     27.00 124.00   0.50    0.50    --   94.60 -82.00 -60.00  194
 45  \w     69.00 183.00   0.50    0.50    --   94.60  67.00 -11.16  228
 46  \w    133.00 176.00   0.50    0.50    --   94.60  61.00 -90.00   86
 47  \w     67.00 173.00   0.50    0.50    --   94.60  73.00-149.92  212
 48  \w     72.00 116.00   0.50    0.50    --   94.60  61.00 -90.00   88
 49  \w     71.00 152.00   0.50    0.50    --   94.60  61.00  90.00  162
 50  \w    146.00 172.00   0.50    0.50    --   94.60  61.00  30.00   52
 51  \w     73.00 124.00   0.50    0.50    --   94.60  61.00  30.00  102
 52  \w     85.00 119.00   0.50    0.50    --   94.60 -82.00  30.00   68
 53  \w      5.00  77.00   0.50    0.50    --   94.60 -82.00-120.00  144
 54  \w    101.00 126.00   0.50    0.50    --   94.60 -82.00-120.00   50
 55  \w      6.00  42.00   0.50    0.50    --   94.60 -82.00  30.00   72
 56  \w     74.00 155.00   0.50    0.50    --   94.60  61.00  60.00  162
 57  \w     87.00 128.00   0.50    0.50    --   94.60  82.00 -90.00   82
 58  \w    157.00 183.00   0.50    0.50    --   94.60  82.00 -90.00   52
 59  \w    120.00 164.00   0.50    0.50    --   94.60  30.00 150.00   88
 60  \w     82.00 107.00   0.50    0.50    --   94.60  30.00 150.00   50
 61  \w     94.00 125.00   0.50    0.50    --   94.60 -82.00  90.00   62
 62  \w     72.00 140.00   0.50    0.50    --   94.60  61.00-180.00  136
 63  \w     72.00 168.00   0.50    0.50    --   94.60  61.00 -30.00  192
 64  \w     45.00 111.00   0.50    0.50    --   94.60 -82.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1881243000
_diffrn_orient_matrix_UB_12      0.0753954000
_diffrn_orient_matrix_UB_13      0.0220309000
_diffrn_orient_matrix_UB_21      -0.0146314000
_diffrn_orient_matrix_UB_22      -0.0797420000
_diffrn_orient_matrix_UB_23      -0.1228626000
_diffrn_orient_matrix_UB_31      -0.0120578000
_diffrn_orient_matrix_UB_32      0.1208925000
_diffrn_orient_matrix_UB_33      -0.0255606000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.909
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0430P)^2^+0.6614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4405
_reflns_number_total             4498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02040_si_002.cif
_cod_data_source_block           20181127-1
_cod_depositor_comments          'Adding full bibliography for 4033611.cif.'
_cod_original_cell_volume        1142.22(4)
_cod_database_code               4033611
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.659
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00X(H00B,H00C,H00P)
;
_shelx_res_checksum              77127
_shelx_hkl_checksum              64850
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.331
_oxdiff_exptl_absorpt_empirical_full_min 0.545