[4 + 1] annulation reaction of cyclic pyridinium ylides with in situ generated azoalkenes for the construction of spirocyclic skeletons.
Quan, Bao-Xue; Zhuo, Jun-Rui; Zhao, Jian-Qiang; Zhang, Ming-Liang; Zhou, Ming-Qiang; Zhang, Xiao-Mei; Yuan, Wei-Cheng; Organic & biomolecular chemistry 18 (2020) 1886–1891; doi:10.1039/c9ob02733e

data_7157360
_publ_section_title
;
 [4 + 1] annulation reaction of cyclic pyridinium ylides with in situ
 generated azoalkenes for the construction of spirocyclic skeletons.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1886
_journal_page_last               1891
_journal_paper_doi               10.1039/c9ob02733e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C25 H23 N3 O3 S'
_chemical_formula_sum            'C25 H23 N3 O3 S'
_chemical_formula_weight         445.52
_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     direct
_audit_creation_date             2019-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-16 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.819(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3770(5)
_cell_length_b                   23.6227(13)
_cell_length_c                   12.1418(7)
_cell_measurement_reflns_used    2570
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8870
_cell_measurement_theta_min      4.2930
_cell_volume                     2260.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   11.00   37.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 26

  2 omega  -66.00  -34.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 32

  3 omega -100.00  -72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 28

  4 omega  -49.00   -7.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 42

  5 omega   78.00  106.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 28

  6 omega  -24.00    8.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 32

  7 omega   13.00   39.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 26

  8 omega   72.00  105.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 33

  9 omega   18.00   68.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 50

 10 omega   79.00  110.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 31

 11 omega   20.00   53.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 33

 12 omega   13.00   39.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 26

 13 omega   57.00   82.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 25

 14 omega   80.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 45

 15 omega  108.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 68

 16 omega   62.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

 17 omega   48.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 59

 18 omega  102.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 64

 19 omega   88.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 88

 20 omega  119.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 34

 21 omega   38.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 48

 22 omega   56.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 51

 23 omega   38.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0284780000
_diffrn_orient_matrix_UB_12      -0.0314785000
_diffrn_orient_matrix_UB_13      0.1029424000
_diffrn_orient_matrix_UB_21      0.0297243000
_diffrn_orient_matrix_UB_22      0.0556036000
_diffrn_orient_matrix_UB_23      0.0705264000
_diffrn_orient_matrix_UB_31      -0.1911226000
_diffrn_orient_matrix_UB_32      0.0133704000
_diffrn_orient_matrix_UB_33      -0.0512411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.742
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0549P)^2^+0.3063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3133
_reflns_number_total             4023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02733e2.cif
_cod_data_source_block           201905118
_cod_depositor_comments
'Adding full bibliography for 7157360--7157361.cif.'
_cod_database_code               7157360
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Co1
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.803
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'