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_7158942
_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         'C19 H12 O4 S'
_chemical_formula_sum            'C19 H12 O4 S'
_chemical_formula_weight         336.35
_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             2020-09-09
_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                 91.9180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0549(2)
_cell_length_b                   7.12140(10)
_cell_length_c                   14.8120(2)
_cell_measurement_reflns_used    19120
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9750
_cell_measurement_theta_min      2.0550
_cell_volume                     1481.71(4)
_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 0.971
_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  38.00   0.50    2.82    --   10.60 -82.00 108.21  234
  2  \w    -17.00 100.00   0.50    2.82    --   10.60  82.00 150.00  234
  3  \w    -15.00 100.00   0.50    2.82    --   10.60  77.00  30.00  230
  4  \w    -79.00  36.00   0.50    2.82    --   10.60 -77.00 150.00  230
  5  \w    -79.00  41.00   0.50    2.82    --   10.60 -57.00-150.00  240
  6  \w    -15.00 100.00   0.50    2.82    --   10.60  77.00 -60.00  230
  7  \w    -68.00  35.00   0.50    2.82    --   10.60 -82.00-150.00  206
  8  \w      0.00 100.00   0.50    2.82    --   10.60  82.00  60.00  200
  9  \w     63.00  89.00   0.50    2.82    --   10.60  77.00  90.00   52
 10  \w    -12.00  76.00   0.50    2.82    --   10.60  82.00  30.00  176
 11  \w    -78.00  -3.00   0.50    2.82    --   10.60 -79.00  17.65  150
 12  \w     -7.00  54.00   0.50    2.82    --   10.60  82.00 -30.00  122
 13  \w    -62.00  10.00   0.50    2.82    --  -10.90 -82.00 120.00  144
 14  \w    -27.00   4.00   0.50    2.82    --  -10.90 -82.00  90.00   62
 15  \w   -100.00 -49.00   0.50    2.82    --  -10.90 -82.00  90.00  102
;
_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      -0.0372354000
_diffrn_orient_matrix_UB_12      0.0103336000
_diffrn_orient_matrix_UB_13      -0.0331166000
_diffrn_orient_matrix_UB_21      0.0336439000
_diffrn_orient_matrix_UB_22      0.0274082000
_diffrn_orient_matrix_UB_23      -0.0321242000
_diffrn_orient_matrix_UB_31      0.0056175000
_diffrn_orient_matrix_UB_32      -0.0952354000
_diffrn_orient_matrix_UB_33      -0.0128487000
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31306
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.965
_diffrn_reflns_theta_min         2.752
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47352
_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    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0400P)^2^+0.7198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01703b2.cif
_cod_data_source_block           k10909-myc-b
_cod_database_code               7158942
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C35 H24 S3 O8'
_diffrn_oxdiff_digest_frames
;
01cd1435356f3fc05eadad5ac103913a41000254f19
;
_diffrn_oxdiff_digest_hkl
;
01a76e0b9b112a5a949cad7299bfa69d9628ad
;
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              50099
_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 1.570
_oxdiff_exptl_absorpt_empirical_full_min 0.632