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_7158944
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-12-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-12-08 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.673(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5860(3)
_cell_length_b                   12.8979(2)
_cell_length_c                   16.9919(3)
_cell_measurement_reflns_used    21454
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9020
_cell_measurement_theta_min      2.1450
_cell_volume                     3151.85(11)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -27.00 100.00   0.50   30.65    --   10.60  38.00   0.00  254
  2  \w    -20.00 100.00   0.50   30.65    --   10.60  57.00 -60.00  240
  3  \w    -17.00 100.00   0.50   30.65    --   10.60  82.00   0.00  234
  4  \w    -17.00 100.00   0.50   30.65    --   10.60  82.00  30.00  234
  5  \w    -15.00 100.00   0.50   30.65    --   10.60  77.00 -90.00  230
  6  \w    -41.00  75.00   0.50   30.65    --  -10.90  57.00-120.00  232
  7  \w    -54.00  19.00   0.50   30.65    --  -10.90 -57.00-120.00  146
  8  \w    -94.00 -61.00   0.50   30.65    --  -10.90 -57.00-120.00   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      -0.0317394000
_diffrn_orient_matrix_UB_12      -0.0335325000
_diffrn_orient_matrix_UB_13      0.0081500000
_diffrn_orient_matrix_UB_21      -0.0193115000
_diffrn_orient_matrix_UB_22      0.0429573000
_diffrn_orient_matrix_UB_23      0.0134032000
_diffrn_orient_matrix_UB_31      -0.0324793000
_diffrn_orient_matrix_UB_32      0.0071859000
_diffrn_orient_matrix_UB_33      -0.0424291000
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40771
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.121
_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  0.89356
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.437
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         5551
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0897
_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^)+(0.0586P)^2^+12.0123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4909
_reflns_number_total             5551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01703b2.cif
_cod_data_source_block           k10912-myc-b
_cod_original_cell_volume        3151.85(10)
_cod_database_code               7158944
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.70
_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. Rigid bond restraints
 C11, C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 7.7
 C18, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 12
3. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4.a Riding coordinates:
 O1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20), C23(H23), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33),
  C34(H34)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              723
_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 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.880