Metal-free hydroalkoxylation of ynesulfonamides with esters.
Gao, Erhui; Peng, Cheng; Zhang, Jingyi; Wang, Xiao-Na; Chang, Junbiao; Organic & biomolecular chemistry 19 (2021) 2182–2185; doi:10.1039/d0ob02575e

data_7157876
_publ_section_title
;
 Metal-free hydroalkoxylation of ynesulfonamides with esters.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2182
_journal_page_last               2185
_journal_paper_doi               10.1039/d0ob02575e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C34 H36 N2 O5 S2'
_chemical_formula_sum            'C34 H36 N2 O5 S2'
_chemical_formula_weight         616.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-02
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2019-11-23 deposited with the CCDC.	2021-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.86040(16)
_cell_length_b                   17.5424(3)
_cell_length_c                   28.9789(4)
_cell_measurement_reflns_used    4658
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.7470
_cell_measurement_theta_min      3.7680
_cell_volume                     6537.71(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -67.00  -33.80   0.4000    0.4000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   90.0000 83

  2 omega   10.00   42.00   0.4000    0.4000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 80

  3 omega   41.00   67.00   0.4000    0.4000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   60.0000 -158.0000 65

  4 omega  -32.00   28.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000    0.0000 150

  5 omega -111.00  -85.80   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -60.0000   62.0000 63

  6 omega  -73.00  -47.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 65

  7 omega -109.00  -17.00   0.4000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000   60.0000 230

  8 omega   43.00   73.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 75

  9 omega   63.00   89.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 65

 10 omega   47.00   72.20   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 63

 11 omega   41.00   79.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 95

 12 omega   43.00   69.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 65

 13 omega   44.00  114.00   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 175

 14 omega   40.00   87.20   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 118

 15 omega   88.00  164.80   0.4000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 192
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0555336000
_diffrn_orient_matrix_UB_12      -0.0410648000
_diffrn_orient_matrix_UB_13      -0.0400746000
_diffrn_orient_matrix_UB_21      0.0650960000
_diffrn_orient_matrix_UB_22      0.0457407000
_diffrn_orient_matrix_UB_23      -0.0349545000
_diffrn_orient_matrix_UB_31      0.0838940000
_diffrn_orient_matrix_UB_32      -0.0626315000
_diffrn_orient_matrix_UB_33      0.0006981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.528
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.35
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_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5841
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0686P)^2^+0.7371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                4652
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02575e4.cif
_cod_data_source_block           201509178
_cod_depositor_comments
'Adding full bibliography for 7157875--7157876.cif.'
_cod_original_cell_volume        6537.70(15)
_cod_database_code               7157876
_chemical_oxdiff_formula         C20H20N4
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.568
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C34) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C32(H32), C33(H33)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              80445
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'