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_7159065
_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 H33 F O4 S2'
_chemical_formula_sum            'C39 H33 F O4 S2'
_chemical_formula_weight         648.77
_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             2021-05-26
_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                70.533(2)
_cell_angle_beta                 77.497(2)
_cell_angle_gamma                82.6410(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0372(2)
_cell_length_b                   13.1158(2)
_cell_length_c                   13.3176(3)
_cell_measurement_reflns_used    41091
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9960
_cell_measurement_theta_min      1.6830
_cell_volume                     1610.80(6)
_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 0.998
_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    -79.00  36.00   0.50    6.93    --   10.60 -77.00 -90.00  230
  2  \w    -17.00 100.00   0.50    6.93    --   10.60  82.00  90.00  234
  3  \w    -17.00 100.00   0.50    6.93    --   10.60  82.00 150.00  234
  4  \w    -17.00 100.00   0.50    6.93    --   10.60  82.00   0.00  234
  5  \w    -17.00 100.00   0.50    6.93    --   10.60  82.00  60.00  234
  6  \w    -79.00  41.00   0.50    6.93    --   10.60 -57.00-180.00  240
  7  \w    -20.00 100.00   0.50    6.93    --   10.60  57.00-120.00  240
  8  \w   -100.00  17.00   0.50    6.93    --  -10.90 -82.00  90.00  234
  9  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00-120.00  234
 10  \w   -100.00  17.00   0.50    6.93    --  -10.90 -82.00-180.00  234
 11  \w    -36.00  78.00   0.50    6.93    --  -10.90  75.00 112.58  228
 12  \w    -38.00  78.00   0.50    6.93    --  -10.90  82.00 -71.92  232
 13  \w    -79.00  38.00   0.50    6.93    --   10.60 -82.00 150.00  234
 14  \w    -15.00 100.00   0.50    6.93    --   10.60  77.00 -60.00  230
 15  \w    -79.00 -54.00   0.50    6.93    --   10.60 -82.00-180.00   50
 16  \w    -79.00  38.00   0.50    6.93    --   10.60 -82.00 120.00  234
 17  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00-180.00  234
 18  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00 -30.00  234
 19  \w    -36.00  79.00   0.50    6.93    --  -10.90  77.00   0.00  230
 20  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00  60.00  234
 21  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00-150.00  234
 22  \w    -38.00  79.00   0.50    6.93    --  -10.90  82.00  30.00  234
 23  \w    -41.00  79.00   0.50    6.93    --  -10.90  57.00  60.00  240
;
_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      -0.0199981000
_diffrn_orient_matrix_UB_12      0.0262751000
_diffrn_orient_matrix_UB_13      0.0401202000
_diffrn_orient_matrix_UB_21      -0.0411368000
_diffrn_orient_matrix_UB_22      -0.0434415000
_diffrn_orient_matrix_UB_23      0.0330089000
_diffrn_orient_matrix_UB_31      0.0562729000
_diffrn_orient_matrix_UB_32      -0.0269203000
_diffrn_orient_matrix_UB_33      0.0246179000
_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  0.1042
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            68143
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.931
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40141
_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    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5657
_refine_ls_number_restraints     1302
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0473P)^2^+0.7328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5139
_reflns_number_total             5657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02188a2.cif
_cod_data_source_block           k11005-myc-h
_cod_depositor_comments
'Adding full bibliography for 7159064--7159067.cif.'
_cod_database_code               7159065
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
016c4a7e495caff3ee62b67a3dbd43824300025e571
;
_diffrn_oxdiff_digest_hkl
;
01051b8ba0d7b32226c68004653ec5ade5f99b
;
_reflns_odcompleteness_completeness 99.74
_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. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim O1 \\sim O2
\\sim O3 \\sim O4 \\sim S1 \\sim S2 \\sim F1: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C18(H18), C19(H19), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16),
 C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31),
  C34(H34), C35(H35), C37(H37), C38(H38)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C39(H39A,H39B,H39C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              77631
_shelx_fab_checksum              89574
_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 2.655
_oxdiff_exptl_absorpt_empirical_full_min 0.361