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_7157618
_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     iterative
_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                69.112(11)
_cell_angle_beta                 87.877(10)
_cell_angle_gamma                65.530(12)
_cell_formula_units_Z            2
_cell_length_a                   10.9174(14)
_cell_length_b                   11.9111(14)
_cell_length_c                   12.3891(14)
_cell_measurement_reflns_used    4882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4050
_cell_measurement_theta_min      2.0220
_cell_volume                     1358.3(3)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.934
_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    -63.00  28.00   0.50   14.15    --   10.60   0.00-180.00  182
  2  \w    -14.00  24.00   0.50   14.15    --   10.60  77.00  30.00   76
  3  \w    -13.00  72.00   0.50   14.15    --   10.60  82.00 -30.00  170
  4  \w     54.00  88.00   0.50   14.15    --   10.60   0.00-180.00   68
  5  \w    -16.00  84.00   0.50   14.15    --   10.60  82.00  90.00  200
  6  \w    -16.00 100.00   0.50   14.15    --   10.60  82.00 150.00  232
  7  \w    -17.00  13.00   0.50   14.15    --   10.60  82.00-150.00   60
  8  \w     23.00  61.00   0.50   14.15    --   10.60  82.00-150.00   76
  9  \w     63.00  88.00   0.50   14.15    --   10.60  82.00-150.00   50
 10  \w     -8.00  80.00   0.50   14.15    --   10.60  57.00  90.00  176
 11  \w    -14.00  63.00   0.50   14.15    --   10.60  82.00-120.00  154
 12  \w    -81.00 -27.00   0.50   14.15    --  -10.90 -77.00 -60.00  108
 13  \w     44.00  69.00   0.50   14.15    --  -10.90  82.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1441
_diffrn_reflns_av_unetI/netI     0.1230
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17787
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.091
_diffrn_reflns_theta_min         2.026
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47499
_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            colorless
_exptl_crystal_density_diffrn    1.402
_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         0.576
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1930
_refine_ls_R_factor_gt           0.1112
_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^)+(0.1867P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2688
_refine_ls_wR_factor_ref         0.3225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2879
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01404d2.cif
_cod_data_source_block           kt6pc93
_cod_depositor_comments
'Adding full bibliography for 7157612--7157619.cif.'
_cod_database_code               7157618
_shelx_shelxl_version_number     2014/7
_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
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C23) \\sim
Ueq, Uanis(C14) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C31) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
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:
 C14(H14), C11(H11), C18(H18), C7(H7), C13(H13), C12(H12), C20(H20), C5(H5A),
 C6(H6), C19(H19), C25(H25), C28(H28), C26(H26), C27(H27)
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
;