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_7159067
_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         'C33 H30 O3 S'
_chemical_formula_sum            'C33 H30 O3 S'
_chemical_formula_weight         506.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-25
_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                90
_cell_angle_beta                 99.682(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4129(3)
_cell_length_b                   9.4208(2)
_cell_length_c                   20.8615(4)
_cell_measurement_reflns_used    23532
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9370
_cell_measurement_theta_min      1.9800
_cell_volume                     2598.52(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  41.00   0.50   16.09    --   10.60 -57.00  30.00  240
  2  \w    -15.00 100.00   0.50   16.09    --   10.60  77.00  30.00  230
  3  \w    -20.00 100.00   0.50   16.09    --   10.60  57.00  30.00  240
  4  \w    -79.00  48.00   0.50   16.09    --   10.60 -38.00  90.00  254
  5  \w    -20.00 100.00   0.50   16.09    --   10.60  57.00 150.00  240
  6  \w   -100.00  27.00   0.50   16.09    --  -10.90 -38.00  30.00  254
  7  \w   -100.00  15.00   0.50   16.09    --  -10.90 -77.00 -30.00  230
  8  \w    -41.00  79.00   0.50   16.09    --  -10.90  57.00 -90.00  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      -0.0483559000
_diffrn_orient_matrix_UB_12      -0.0205353000
_diffrn_orient_matrix_UB_13      0.0062893000
_diffrn_orient_matrix_UB_21      -0.0204964000
_diffrn_orient_matrix_UB_22      0.0100375000
_diffrn_orient_matrix_UB_23      -0.0333015000
_diffrn_orient_matrix_UB_31      0.0109908000
_diffrn_orient_matrix_UB_32      -0.0717114000
_diffrn_orient_matrix_UB_33      -0.0063825000
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38649
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36112
_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    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0498P)^2^+0.9890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4112
_reflns_number_total             4582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02188a2.cif
_cod_data_source_block           k11005-myc-g
_cod_depositor_comments
'Adding full bibliography for 7159064--7159067.cif.'
_cod_database_code               7159067
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
011d921008789c9e64688cd7fc3f22e43100025b54f
;
_diffrn_oxdiff_digest_hkl
;
019ed252f824d4c7bfcc4cfa95ecf0e1d3bcb5
;
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C13(H13), C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              38001
_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 1.798
_oxdiff_exptl_absorpt_empirical_full_min 0.381