Photocatalyst-free H2O-regulated and regiodivergent multicomponent hydrogenation/bifunctional sulfonylation of alkynes
Sun, Jie; Wang, Chaodong; Wu, Chunlei; Wang, Wenjian; Zeng, Yue; Song, Shengjie; Chen, Zhiwei; Li, Jianjun; Green Chemistry 26 (2024) 3301–3307; doi:10.1039/D3GC04960D

data_7248381
_publ_section_title
;
 Photocatalyst-free H2O-regulated and regiodivergent multicomponent
 hydrogenation/bifunctional sulfonylation of alkynes
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              3301
_journal_page_last               3307
_journal_paper_doi               10.1039/D3GC04960D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C27 H21 F2 N O6 S'
_chemical_formula_sum            'C27 H21 F2 N O6 S'
_chemical_formula_weight         525.534
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-13 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2939(4)
_cell_length_b                   9.7381(4)
_cell_length_c                   25.5602(11)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.50
_cell_volume                     2561.06(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            61900
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9992
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.50
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.9547.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1089.319
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3399
_refine_diff_density_min         -0.4370
_refine_diff_density_rms         0.0742
_refine_ls_d_res_high            0.7693
_refine_ls_d_res_low             8.1340
_refine_ls_goodness_of_fit_ref   1.0574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5903
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      1.0368
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          1.4494
_refine_ls_shift/su_mean         0.0719
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+1.2739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                4458
_reflns_number_total             5903
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3gc04960d2.cif
_cod_data_source_block           mo_230411_SJ_P_OCH3_0m
_cod_original_formula_sum        'C27 H21 F2 N1 O6 S1'
_cod_database_code               7248381
_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. Restrained distances
 N1-C22 \\sim N1-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 C22-C27 \\sim C22A-C27A
 with sigma of 0.02
 C25-C27 \\sim C25A-C27A
 with sigma of 0.04
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C24-C26 \\sim C24A-C26A
 with sigma of 0.04
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C25-C23 \\sim C25A-C23A
 with sigma of 0.04
 C27-C26 \\sim C27A-C26A
 with sigma of 0.02
 C23-C27 \\sim C23A-C27A
 with sigma of 0.04
 N1-C23 \\sim N1-C23A
 with sigma of 0.04
 N1-C27 \\sim N1-C27A
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
 C22-C26 \\sim C22A-C26A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N1 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C22A \\sim
C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=1-FVAR(1)
 Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=
 Sof(H26)=Sof(C27)=Sof(H27)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C21(H21a,H21b)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A)
5.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'