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_7158940
_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         'C17 H18 O7 S2'
_chemical_formula_sum            'C17 H18 O7 S2'
_chemical_formula_weight         398.43
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-14
_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                100.946(3)
_cell_angle_beta                 96.419(2)
_cell_angle_gamma                118.360(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8981(3)
_cell_length_b                   9.9008(3)
_cell_length_c                   10.6735(3)
_cell_measurement_reflns_used    8160
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8950
_cell_measurement_theta_min      2.3890
_cell_volume                     878.66(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -30.00  -5.00   0.50    4.44    --   10.60 -80.00 -93.00   50
  2  \w     42.00  67.00   0.50    4.44    --   10.60  80.00  29.00   50
  3  \w      4.00  78.00   0.50    4.44    --  -10.90  80.00  29.00  148
  4  \w    -47.00  13.00   0.50    4.44    --  -10.90 -80.00 -93.00  120
  5  \w     44.00  70.00   0.50    4.44    --   10.60  77.00  90.00   52
  6  \w    -78.00  12.00   0.50    4.44    --   10.60 -57.00 -60.00  180
  7  \w     -2.00  24.00   0.50    4.44    --   10.60  82.00-180.00   52
  8  \w    -15.00  11.00   0.50    4.44    --   10.60 -82.00  60.00   52
  9  \w    -78.00  36.00   0.50    4.44    --   10.60 -77.00-150.00  228
 10  \w    -15.00  98.00   0.50    4.44    --   10.60  82.00  90.00  226
 11  \w    -62.00 -36.00   0.50    4.44    --   10.60 -82.00  60.00   52
 12  \w     21.00  77.00   0.50    4.44    --   10.60  77.00 150.00  112
 13  \w    -17.00  11.00   0.50    4.44    --   10.60  82.00 -30.00   56
 14  \w     15.00  41.00   0.50    4.44    --   10.60  82.00 -30.00   52
 15  \w     -8.00  85.00   0.50    4.44    --   10.60  82.00   0.00  186
 16  \w    -40.00  17.00   0.50    4.44    --  -10.90 -82.00  90.00  114
 17  \w    -98.00 -73.00   0.50    4.44    --  -10.90 -82.00  90.00   50
 18  \w    -83.00  14.00   0.50    4.44    --  -10.90 -77.00 150.00  194
;
_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      -0.0146163000
_diffrn_orient_matrix_UB_12      0.0457962000
_diffrn_orient_matrix_UB_13      0.0504114000
_diffrn_orient_matrix_UB_21      0.0228980000
_diffrn_orient_matrix_UB_22      0.0613957000
_diffrn_orient_matrix_UB_23      -0.0320303000
_diffrn_orient_matrix_UB_31      -0.0792272000
_diffrn_orient_matrix_UB_32      -0.0362725000
_diffrn_orient_matrix_UB_33      -0.0357625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14656
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.00
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50235
_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            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0429P)^2^+0.4777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                2966
_reflns_number_total             3438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01703b2.cif
_cod_data_source_block           mcomebs48
_cod_original_cell_volume        878.66(5)
_cod_database_code               7158940
_chemical_oxdiff_formula         'C16 H18 O7 S2'
_diffrn_oxdiff_digest_frames
;
01460424db12a05e967eab8acdd91f252800025753f
;
_diffrn_oxdiff_digest_hkl
;
0180005e5917b0d7321502cf754f1aff94c38d
;
_reflns_odcompleteness_completeness 99.11
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17A,H17B,H17C)
;
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.689