One-pot construction of dispirocyclohexanes via K<sub>2</sub>CO<sub>3</sub>-mediated desulfonylative Michael-Michael-aldol (2 + 2 + 2) annulation of sulfonyl 2-pyridyl flavanones and methylketones.
Chang, Meng-Yang; Chen, Kuan-Ting; Chen, Han-Yu; Organic & biomolecular chemistry 18 (2020) 6297–6311; doi:10.1039/d0ob01404d

data_7157619
_publ_section_title
;
 One-pot construction of dispirocyclohexanes via
 K<sub>2</sub>CO<sub>3</sub>-mediated desulfonylative
 Michael-Michael-aldol (2 + 2 + 2) annulation of sulfonyl 2-pyridyl
 flavanones and methylketones.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6297
_journal_page_last               6311
_journal_paper_doi               10.1039/d0ob01404d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H22 Cl2 N2 O5'
_chemical_formula_sum            'C31 H22 Cl2 N2 O5'
_chemical_formula_weight         573.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-15 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                89.110(4)
_cell_angle_beta                 67.910(4)
_cell_angle_gamma                68.542(5)
_cell_formula_units_Z            2
_cell_length_a                   10.8001(6)
_cell_length_b                   11.3693(6)
_cell_length_c                   13.4193(5)
_cell_measurement_reflns_used    6820
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7930
_cell_measurement_theta_min      2.1580
_cell_volume                     1406.67(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_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  62.00   0.50   21.80    --   10.60  82.00 150.00   58
  2  \w     -4.00  25.00   0.50   21.80    --   10.60  82.00 150.00   58
  3  \w    -12.00  92.00   0.50   21.80    --   10.60  82.00 120.00  208
  4  \w    -17.00  28.00   0.50   21.80    --   10.60  82.00 -30.00   90
  5  \w     31.00  63.00   0.50   21.80    --   10.60  82.00 -30.00   64
  6  \w     -2.00  25.00   0.50   21.80    --   10.60  77.00  60.00   54
  7  \w     57.00  82.00   0.50   21.80    --   10.60  77.00  60.00   50
  8  \w    -78.00 -29.00   0.50   21.80    --   10.60 -77.00 150.00   98
  9  \w    -14.00  11.00   0.50   21.80    --   10.60 -77.00 150.00   50
 10  \w    -78.00  35.00   0.50   21.80    --   10.60 -77.00  60.00  226
 11  \w    -13.00  29.00   0.50   21.80    --   10.60  82.00-150.00   84
 12  \w     46.00  73.00   0.50   21.80    --   10.60  82.00-150.00   54
 13  \w     -4.00  35.00   0.50   21.80    --   10.60  82.00   0.00   78
 14  \w     44.00  71.00   0.50   21.80    --   10.60  82.00   0.00   54
 15  \w    -19.00   9.00   0.50   21.80    --   10.60  57.00 -90.00   56
 16  \w     64.00  99.00   0.50   21.80    --   10.60  57.00 -90.00   70
 17  \w     -3.00  86.00   0.50   21.80    --   10.60  82.00-120.00  178
 18  \w     26.00  51.00   0.50   21.80    --  -10.90   0.00 -60.00   50
 19  \w    -16.00  11.00   0.50   21.80    --  -10.90   0.00 -60.00   54
 20  \w    -99.00 -45.00   0.50   21.80    --  -10.90   0.00 -60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II 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      0.0457289000
_diffrn_orient_matrix_UB_12      0.0261805000
_diffrn_orient_matrix_UB_13      0.0092946000
_diffrn_orient_matrix_UB_21      -0.0430367000
_diffrn_orient_matrix_UB_22      0.0114758000
_diffrn_orient_matrix_UB_23      0.0565982000
_diffrn_orient_matrix_UB_31      0.0444271000
_diffrn_orient_matrix_UB_32      -0.0613865000
_diffrn_orient_matrix_UB_33      0.0055484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.038
_diffrn_reflns_theta_min         2.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0846
_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^)+(0.1081P)^2^+0.9612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3616
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01404d2.cif
_cod_data_source_block           exp_58
_cod_depositor_comments
'Adding full bibliography for 7157612--7157619.cif.'
_cod_original_cell_volume        1406.67(13)
_cod_database_code               7157619
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c31 H22 Cl2 N2 O5'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.947
_diffrn_oxdiff_digest_frames
;
019e15e91ccf508ea9d196f154fbb962fd00025a4d5
;
_diffrn_oxdiff_digest_hkl
;
016a9c088065780df397c47a58367bdacdff6e
;
_reflns_odcompleteness_completeness 98.94
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.05
3.a Ternary CH refined with riding coordinates:
 C16(H16), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C7(H7), C25(H25), C10(H10), C13(H13), C18(H18), C6(H6), C5(H5A),
 C27(H27), C12(H12), C11(H11), C26(H26), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 1.533
_oxdiff_exptl_absorpt_empirical_full_min 0.572