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_7159064
_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         'C39 H34 O4 S2'
_chemical_formula_sum            'C39 H34 O4 S2'
_chemical_formula_weight         630.78
_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             2021-04-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                71.2298(14)
_cell_angle_beta                 77.3026(13)
_cell_angle_gamma                82.5521(14)
_cell_formula_units_Z            2
_cell_length_a                   10.03496(17)
_cell_length_b                   12.9944(2)
_cell_length_c                   13.45263(20)
_cell_measurement_reflns_used    22756
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9200
_cell_measurement_theta_min      1.6740
_cell_volume                     1616.99(5)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(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 0.951
_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    -17.00 100.00   0.50   10.45    --   10.60  82.00   0.00  234
  2  \w    -15.00 100.00   0.50   10.45    --   10.60  77.00 -90.00  230
  3  \w    -79.00  36.00   0.50   10.45    --   10.60 -77.00 -30.00  230
  4  \w    -15.00 100.00   0.50   10.45    --   10.60  77.00 150.00  230
  5  \w    -17.00 100.00   0.50   10.45    --   10.60  82.00  60.00  234
  6  \w    -17.00 100.00   0.50   10.45    --   10.60  82.00-120.00  234
  7  \w     -5.00  92.00   0.50   10.45    --   10.60  82.00 -30.00  194
  8  \w    -17.00  99.00   0.50   10.45    --   10.60  82.00 120.00  232
  9  \w    -79.00   2.00   0.50   10.45    --   10.60 -79.00  41.39  162
 10  \w     -9.00  40.00   0.50   10.45    --   10.60  82.00-180.00   98
 11  \w    -56.00 -26.00   0.50   10.45    --   10.60 -57.00  60.00   60
 12  \w      1.00  27.00   0.50   10.45    --   10.60 -57.00  60.00   52
 13  \w    -11.00  38.00   0.50   10.45    --   10.60  82.00 -60.00   98
 14  \w    -83.00 -11.00   0.50   10.45    --  -10.90 -57.00 -30.00  144
 15  \w    -38.00  57.00   0.50   10.45    --  -10.90  82.00-150.00  190
;
_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      0.0674933000
_diffrn_orient_matrix_UB_12      -0.0000366000
_diffrn_orient_matrix_UB_13      0.0081261000
_diffrn_orient_matrix_UB_21      0.0205874000
_diffrn_orient_matrix_UB_22      0.0287262000
_diffrn_orient_matrix_UB_23      -0.0549085000
_diffrn_orient_matrix_UB_31      -0.0170865000
_diffrn_orient_matrix_UB_32      0.0501202000
_diffrn_orient_matrix_UB_33      0.0116562000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37103
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.074
_diffrn_reflns_theta_min         1.940
_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  0.25822
_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            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0434P)^2^+0.5166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5953
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02188a2.cif
_cod_data_source_block           k11004-myc-d
_cod_depositor_comments
'Adding full bibliography for 7159064--7159067.cif.'
_cod_database_code               7159064
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01f84cc8ca7daa873f61dbc55a3a3551b5000254973
;
_diffrn_oxdiff_digest_hkl
;
01180f90574b58ae6a9537274add33d2a9d8af
;
_reflns_odcompleteness_completeness 99.49
_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:
 C2(H2), C3(H3), C4(H4), C11(H11), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18B,H18A)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31),
  C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C25(H25B,H25A,H25C), C32(H32A,H32C,H32B)
;
_shelx_res_checksum              30667
_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 2.911
_oxdiff_exptl_absorpt_empirical_full_min 0.456