Synthesis of <i>N</i>-sulfonyl acetamidines using calcium carbide as an alkyne source.
Chen, Wei; Wang, Zhiqiang; Yang, Jinhui; Li, Zheng; Organic & biomolecular chemistry 23 (2025) 9001–9007; doi:10.1039/d5ob01072a

data_7160732
_publ_section_title
;
 Synthesis of <i>N</i>-sulfonyl acetamidines using calcium carbide as an
 alkyne source.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9001
_journal_page_last               9007
_journal_paper_doi               10.1039/d5ob01072a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C15 H24 N2 O2 S'
_chemical_formula_sum            'C15 H24 N2 O2 S'
_chemical_formula_weight         296.42
_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             2024-10-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-10-22 deposited with the CCDC.	2025-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.258(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8198(2)
_cell_length_b                   25.8453(4)
_cell_length_c                   8.26570(10)
_cell_measurement_reflns_used    7788
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      76.6960
_cell_measurement_theta_min      5.1340
_cell_volume                     1638.40(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.932
_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    -26.00  23.00   0.50    0.05    --   44.63 -19.00   0.00   98
  2  \w     -2.00  23.00   0.50    0.05    --   44.63 -78.00  -4.00   50
  3  \w     40.00  71.00   0.50    0.05    --  111.16 -78.00  -4.00   62
  4  \w     42.00  67.00   0.50    0.05    --  111.16 -61.00 -60.00   50
  5  \w     73.00  99.00   0.50    0.05    --  111.16 -77.00-150.00   52
  6  \w    -30.00  10.00   0.50    0.05    --   44.63 -19.00-180.00   80
  7  \w     42.00  67.00   0.50    0.05    --  111.16 -61.00   0.00   50
  8  \w     43.00  68.00   0.50    0.05    --  111.16 -61.00 120.00   50
  9  \w     92.00 139.00   0.50    0.05    --  111.16  45.00 -60.00   94
 10  \w     93.00 171.00   0.50    0.05    --  111.16  77.00  30.00  156
 11  \w    105.00 130.00   0.50    0.05    --  111.16  78.00 120.00   50
 12  \w     43.00  68.00   0.50    0.05    --   44.63  78.00 120.00   50
 13  \w    -57.00  10.00   0.50    0.05    --  -44.63  78.00 120.00  134
 14  \w   -112.00 -27.00   0.50    0.05    -- -100.00  78.00 120.00  170
 15  \w    -53.00 -27.00   0.50    0.05    -- -100.00  45.00  90.00   52
 16  \w    -54.00 -26.00   0.50    0.05    -- -100.00  45.00  60.00   56
 17  \w    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -60.00   50
 18  \w    -53.00 -28.00   0.50    0.05    -- -100.00  45.00 -90.00   50
 19  \w   -177.00 -83.00   0.50    0.05    -- -100.00 -30.00  60.00  188
 20  \w   -154.00 -78.00   0.50    0.05    -- -100.00 -78.00  -4.00  152
 21  \w   -171.00 -83.00   0.50    0.05    -- -100.00-125.00  60.00  176
 22  \w   -116.00 -18.00   0.50    0.05    --  -44.63 -78.00  -4.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0521216000
_diffrn_orient_matrix_UB_12      0.0265538000
_diffrn_orient_matrix_UB_13      -0.1694683000
_diffrn_orient_matrix_UB_21      0.1356296000
_diffrn_orient_matrix_UB_22      0.0428257000
_diffrn_orient_matrix_UB_23      0.0564959000
_diffrn_orient_matrix_UB_31      0.1385572000
_diffrn_orient_matrix_UB_32      -0.0318169000
_diffrn_orient_matrix_UB_33      -0.0652363000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9787
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.916
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0962P)^2^+0.4713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3041
_reflns_number_total             3224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01072a2.cif
_cod_data_source_block           wc101_1021_auto
_cod_depositor_comments          'Adding full bibliography for 7160732.cif.'
_cod_database_code               7160732
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              67131
_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 2.767
_oxdiff_exptl_absorpt_empirical_full_min 0.359