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_7158943
_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         'C35 H32 O9 S3'
_chemical_formula_sum            'C35 H32 O9 S3'
_chemical_formula_weight         692.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-12-08 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.187(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6949(6)
_cell_length_b                   12.8939(4)
_cell_length_c                   17.0029(7)
_cell_measurement_reflns_used    11164
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.5970
_cell_measurement_theta_min      2.0320
_cell_volume                     3208.3(2)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     -6.00  22.00   0.50   72.16    --   10.60  82.00  30.00   56
  2  \w     28.00  99.00   0.50   72.16    --   10.60  82.00  30.00  142
  3  \w    -69.00  34.00   0.50   72.16    --   10.60 -77.00-120.00  206
  4  \w    -15.00 100.00   0.50   72.16    --   10.60  82.00 -30.00  230
  5  \w     -9.00  17.00   0.50   72.16    --   10.60  82.00-180.00   52
  6  \w     47.00  84.00   0.50   72.16    --   10.60  82.00-180.00   74
  7  \w     -2.00  31.00   0.50   72.16    --   10.60  82.00  60.00   66
  8  \w     35.00  64.00   0.50   72.16    --  -10.90  38.00   0.00   58
  9  \w     46.00  72.00   0.50   72.16    --  -10.90  77.00  60.00   52
 10  \w    -34.00  52.00   0.50   72.16    --  -10.90  57.00 -30.00  172
;
_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      -0.0086250000
_diffrn_orient_matrix_UB_12      0.0493492000
_diffrn_orient_matrix_UB_13      0.0141084000
_diffrn_orient_matrix_UB_21      -0.0293128000
_diffrn_orient_matrix_UB_22      -0.0234067000
_diffrn_orient_matrix_UB_23      0.0182697000
_diffrn_orient_matrix_UB_31      0.0375553000
_diffrn_orient_matrix_UB_32      -0.0069129000
_diffrn_orient_matrix_UB_33      0.0383380000
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26586
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68806
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.379
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5595
_refine_ls_number_restraints     1434
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0852
_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^)+(0.1155P)^2^+7.7502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2219
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3932
_reflns_number_total             5595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01703b2.cif
_cod_data_source_block           k10911-myc-a
_cod_database_code               7158943
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H28 O9 S3'
_diffrn_oxdiff_digest_frames
;
01c5498c83eab05de7792241a2f2814e36000251768
;
_diffrn_oxdiff_digest_hkl
;
0197fd177c3916c1ee6aa2f9a36c16a207518a
;
_reflns_odcompleteness_completeness 98.34
_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, All O(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 O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim
O7 \\sim O8 \\sim O9 \\sim S1 \\sim S2 \\sim S3: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C25(H25), C26(H26), C30(H30), C31(H31), C33(H33),
  C34(H34)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C27(H27B,H27A,H27C), C28(H28C,H28A,H28B), C35(H35B,H35A,
 H35C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              81811
_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 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.622