[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_7157361
_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         'C24 H20 N2 O3 S'
_chemical_formula_sum            'C24 H20 N2 O3 S'
_chemical_formula_weight         416.48
_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             2019-12-10
_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                 96.103(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3284(5)
_cell_length_b                   8.7436(6)
_cell_length_c                   20.6742(9)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2250
_cell_measurement_theta_min      4.2640
_cell_volume                     2036.19(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 150.00   76
  2  \w   -102.00 -44.00   1.00    1.00    --  -33.50 -57.00 120.00   58
  3  \w    -72.00 -19.00   1.00    1.00    --  -33.50 -37.00-150.00   53
  4  \w     71.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   39
  5  \w     36.00 103.00   1.00    1.00    --   36.47  57.00  60.00   67
  6  \w     -3.00  75.00   1.00    1.00    --   36.47 -99.00 -30.00   78
  7  \w     59.00  94.00   1.00    1.00    --   36.47  57.00   0.00   35
  8  \w    139.00 172.00   1.00    2.50    --  108.00  45.00-180.00   33
  9  \w     38.00 123.00   1.00    2.50    --  108.00 -30.00-120.00   85
 10  \w     88.00 119.00   1.00    2.50    --  108.00  45.00-180.00   31
 11  \w     49.00 105.00   1.00    2.50    --  108.00 -94.00 -90.00   56
 12  \w     99.00 128.00   1.00    2.50    --  108.00 -15.00   0.00   29
 13  \w    113.00 141.00   1.00    2.50    --  108.00  61.00-150.00   28
 14  \w     51.00 109.00   1.00    2.50    --  108.00 -94.00-180.00   58
 15  \w     36.00  96.00   1.00    2.50    --  108.00 -15.00   0.00   60
 16  \w    113.00 139.00   1.00    2.50    --  108.00 111.00 -90.00   26
 17  \w     51.00 128.00   1.00    2.50    --  108.00 -61.00 -30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134691000
_diffrn_orient_matrix_UB_12      0.0435411000
_diffrn_orient_matrix_UB_13      0.0726445000
_diffrn_orient_matrix_UB_21      -0.1357542000
_diffrn_orient_matrix_UB_22      -0.0069431000
_diffrn_orient_matrix_UB_23      0.0003141000
_diffrn_orient_matrix_UB_31      0.0088524000
_diffrn_orient_matrix_UB_32      -0.1708763000
_diffrn_orient_matrix_UB_33      0.0185101000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.053
_diffrn_reflns_theta_max         67.053
_diffrn_reflns_theta_min         4.270
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.359
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00134(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0633P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2656
_reflns_number_total             3620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02733e2.cif
_cod_data_source_block           201912317
_cod_depositor_comments
'Adding full bibliography for 7157360--7157361.cif.'
_cod_original_cell_volume        2036.18(18)
_cod_database_code               7157361
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4S1
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.745
_reflns_odcompleteness_completeness 99.87
_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:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              22893
_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.896