Sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to biscyclopropane-fused tetralins.
Hsueh, Nai-Chen; Wang, Yu-Han; Chang, Meng-Yang; Organic & biomolecular chemistry 21 (2023) 1206–1221; doi:10.1039/d2ob02188a

data_7159066
_publ_section_title
;
 Sequential condensation and double desulfonylative cyclopropanation of
 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to
 biscyclopropane-fused tetralins.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1206
_journal_page_last               1221
_journal_paper_doi               10.1039/d2ob02188a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C40 H36 O5 S2'
_chemical_formula_sum            'C40 H36 O5 S2'
_chemical_formula_weight         660.81
_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             2021-05-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                76.000(2)
_cell_angle_beta                 76.377(3)
_cell_angle_gamma                83.538(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1215(3)
_cell_length_b                   12.7300(3)
_cell_length_c                   13.7066(4)
_cell_measurement_reflns_used    10798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8720
_cell_measurement_theta_min      1.6900
_cell_volume                     1662.49(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.954
_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    -20.00 100.00   0.50    4.60    --   10.60  57.00-120.00  240
  2  \w    -20.00 100.00   0.50    4.60    --   10.60  57.00  60.00  240
  3  \w    -17.00 100.00   0.50    4.60    --   10.60  82.00  30.00  234
  4  \w    -15.00 100.00   0.50    4.60    --   10.60  77.00-120.00  230
  5  \w    -79.00  38.00   0.50    4.60    --   10.60 -81.00 135.29  234
;
_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      -0.0191532000
_diffrn_orient_matrix_UB_12      -0.0472818000
_diffrn_orient_matrix_UB_13      -0.0105941000
_diffrn_orient_matrix_UB_21      0.0071036000
_diffrn_orient_matrix_UB_22      -0.0297823000
_diffrn_orient_matrix_UB_23      0.0495513000
_diffrn_orient_matrix_UB_31      -0.0693835000
_diffrn_orient_matrix_UB_32      0.0135991000
_diffrn_orient_matrix_UB_33      0.0202710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.038
_diffrn_reflns_theta_min         2.008
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0063(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0449P)^2^+0.5455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6197
_reflns_number_total             6935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02188a2.cif
_cod_data_source_block           k11005-myc-b
_cod_depositor_comments
'Adding full bibliography for 7159064--7159067.cif.'
_cod_original_cell_volume        1662.50(8)
_cod_database_code               7159066
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 86.61
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12), C10(H10), C11(H11), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C39(H39), C17(H17), C35(H35), C28(H28), C14(H14), C4(H4), C38(H38),
 C36(H36), C7(H7), C32(H32), C5(H5), C24(H24), C6(H6), C31(H31), C23(H23),
 C29(H29), C18(H18), C15(H15), C22(H22)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C19(H19A,H19B,H19C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              12402
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.643