Tandem cyclocondensation of 1,3-bis-sulfonylpropan-2-ones with arylaldehydes. One-pot synthesis of tris-sulfonyl 3-arylphenols
Hsueh, Nai-Chen; Chang, Meng-Yang; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01703B

data_7158946
_publ_section_title
;
 Tandem cyclocondensation of 1,3-bis-sulfonylpropan-2-ones with
 arylaldehydes. One-pot synthesis of tris-sulfonyl 3-arylphenols
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01703B
_journal_year                    2022
_chemical_formula_moiety         'C31 H24 O7 S3, C4 H8 O'
_chemical_formula_sum            'C35 H32 O8 S3'
_chemical_formula_weight         676.79
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-08 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                93.598(2)
_cell_angle_beta                 95.572(2)
_cell_angle_gamma                90.367(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3583(3)
_cell_length_b                   10.9812(3)
_cell_length_c                   17.0446(5)
_cell_measurement_reflns_used    17773
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7810
_cell_measurement_theta_min      1.8530
_cell_volume                     1553.84(8)
_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    '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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -79.00 100.00   0.50   17.31    --   10.60   0.00 -60.00  358
  2  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00 120.00  234
  3  \w    -15.00 100.00   0.50   17.31    --   10.60  77.00  30.00  230
  4  \w    -79.00  36.00   0.50   17.31    --   10.60 -77.00-180.00  230
  5  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00-150.00  234
  6  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00   0.00  234
  7  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00  60.00  234
  8  \w    -20.00 100.00   0.50   17.31    --   10.60  57.00 -30.00  240
  9  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00-180.00  234
 10  \w    -17.00 100.00   0.50   17.31    --   10.60  82.00 -60.00  234
 11  \w     -3.00  23.00   0.50   17.31    --   10.60  82.00  90.00   52
 12  \w     62.00  95.00   0.50   17.31    --   10.60  82.00  90.00   66
;
_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      -0.0039647000
_diffrn_orient_matrix_UB_12      0.0615283000
_diffrn_orient_matrix_UB_13      -0.0103857000
_diffrn_orient_matrix_UB_21      0.0101138000
_diffrn_orient_matrix_UB_22      0.0200458000
_diffrn_orient_matrix_UB_23      0.0405711000
_diffrn_orient_matrix_UB_31      0.0845762000
_diffrn_orient_matrix_UB_32      0.0013085000
_diffrn_orient_matrix_UB_33      -0.0012121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34076
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.86
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37078
_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            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+2.3850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                5314
_reflns_number_total             6090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01703b2.cif
_cod_data_source_block           mc0207
_cod_database_code               7158946
_chemical_oxdiff_formula         'C28 H20 S2 O5'
_diffrn_oxdiff_digest_frames
;
014d74f33d386d624237653a4882dfc1f5000251ba1
;
_diffrn_oxdiff_digest_hkl
;
01653f38509abee61c0f17b83e708da243681a
;
_reflns_odcompleteness_completeness 99.40
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.471