Visible-light-induced bifunctionalisation of (homo)propargylic amines with CO<sub>2</sub> and arylsulfinates.
Reddy, Mandapati Bhargava; McGarrigle, Eoghan M.; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc04160c

data_7132290
_publ_section_title
;
 Visible-light-induced bifunctionalisation of (homo)propargylic amines
 with CO<sub>2</sub> and arylsulfinates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04160c
_journal_year                    2023
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-08-08 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.30520(10)
_cell_length_b                   7.33200(10)
_cell_length_c                   18.7530(2)
_cell_measurement_reflns_used    11707
_cell_measurement_temperature    104.4(5)
_cell_measurement_theta_max      72.6420
_cell_measurement_theta_min      3.6500
_cell_volume                     1653.14(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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      104.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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   -104.00 -17.00   1.00    4.34    --  -42.33 149.00 -59.00   87
  2  \w   -115.00 -62.00   1.00    4.34    --  -42.33-149.00-106.00   53
  3  \w    -85.00  -3.00   1.00    4.34    --  -42.33 122.00 137.00   82
  4  \w     39.00 114.00   1.00    4.34    --   42.33-149.00-106.00   75
  5  \w     39.00 129.00   1.00   17.34    --  104.49-149.00-106.00   90
  6  \w     99.00 176.00   1.00   17.34    --  104.49 122.00 137.00   77
  7  \w     33.00 111.00   1.00   17.34    --  104.49-122.00  56.00   78
  8  \w     83.00 167.00   1.00   17.34    --  104.49 149.00 -59.00   84
  9  \w   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00-150.00  101
 10  \w   -117.00 -18.00   1.00    4.34    --  -42.33 -37.00 -60.00   99
 11  \w    103.00 178.00   1.00   17.34    --  104.49  77.00   0.00   75
 12  \w     31.00 109.00   1.00   17.34    --  104.49-111.00 150.00   78
 13  \w     28.00 137.00   1.00   17.34    --  104.49 -77.00  60.00  109
 14  \w    103.00 178.00   1.00   17.34    --  104.49  77.00-120.00   75
 15  \w    103.00 178.00   1.00   17.34    --  104.49  77.00-180.00   75
 16  \w    103.00 178.00   1.00   17.34    --  104.49  77.00 -30.00   75
 17  \w    103.00 178.00   1.00   17.34    --  104.49  77.00  30.00   75
 18  \w   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00   0.00  101
 19  \w   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00 -90.00  101
 20  \w   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00  90.00  101
 21  \w   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00 150.00  101
 22  \w    -67.00  32.00   1.00    4.34    --  -42.33  37.00   0.00   99
 23  \w     75.00 177.00   1.00   17.34    --  104.49  61.00 -60.00  102
 24  \w     76.00 178.00   1.00   17.34    --  104.49  30.00 120.00  102
 25  \w     76.00 178.00   1.00   17.34    --  104.49  30.00-150.00  102
 26  \w     31.00 109.00   1.00   17.34    --  104.49-111.00 -30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1136838000
_diffrn_orient_matrix_UB_12      0.0232937000
_diffrn_orient_matrix_UB_13      -0.0208689000
_diffrn_orient_matrix_UB_21      0.0071415000
_diffrn_orient_matrix_UB_22      -0.2078534000
_diffrn_orient_matrix_UB_23      -0.0101651000
_diffrn_orient_matrix_UB_31      -0.0586322000
_diffrn_orient_matrix_UB_32      0.0202750000
_diffrn_orient_matrix_UB_33      -0.0808155000
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.687
_diffrn_reflns_theta_min         3.676
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0443P)^2^+0.8343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2873
_reflns_number_total             3235
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04160c3.cif
_cod_data_source_block           BR-2-44A_exp_1233
_cod_database_code               7132290
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H17NO4S
_chemical_oxdiff_usercomment     BR-2-44A_BhargavaReddy_McGarribleGroup
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.722
_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.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              95047
_shelx_hkl_checksum              14928
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.432