Two-component symmetrical diarylation of ynamides
Sahoo, Aradhana; Dutta, Shubham; Sahoo, Akhila K.; Organic & Biomolecular Chemistry 21 (2023) 5737–5741; doi:10.1039/D3OB00793F

data_7159410
_publ_section_title
;
 Two-component symmetrical diarylation of ynamides
;
_journal_issue                   28
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              5737
_journal_page_last               5741
_journal_paper_doi               10.1039/D3OB00793F
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C34 H31 N O4 S'
_chemical_formula_sum            'C34 H31 N O4 S'
_chemical_formula_weight         549.66
_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             2023-01-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-05-11 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.282(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3009(3)
_cell_length_b                   11.1099(3)
_cell_length_c                   19.7682(5)
_cell_measurement_reflns_used    10323
_cell_measurement_temperature    258
_cell_measurement_theta_max      22.9340
_cell_measurement_theta_min      2.0540
_cell_volume                     2916.39(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      258
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_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    -37.00  21.00   0.50    2.00    --  -15.60 -94.00   0.00  116
  2  \w      5.00  66.00   0.50    2.00    --   16.22-118.00 -23.00  122
  3  \w    -54.00  41.00   0.50    2.00    --   16.22 -45.00 -60.00  190
  4  \w     -8.00  86.00   0.50    2.00    --   16.22  45.00 -90.00  188
  5  \w    -40.00  55.00   0.50    2.00    --  -15.60  45.00-180.00  190
  6  \w    -43.00  -9.00   0.50    2.00    --  -15.60  61.00-120.00   68
  7  \w    -90.00 -28.00   0.50    2.00    --  -15.60 158.00-143.00  124
  8  \w    -88.00  16.00   0.50    2.00    --  -15.60 -77.00 -60.00  208
  9  \w     28.00  91.00   0.50    2.00    --   16.22-158.00-177.00  126
 10  \w    -66.00  -5.00   0.50    2.00    --  -15.60 118.00  62.00  122
 11  \w    -88.00  16.00   0.50    2.00    --  -15.60 -77.00 120.00  208
 12  \w    -88.00  16.00   0.50    2.00    --  -15.60 -77.00 150.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075745000
_diffrn_orient_matrix_UB_12      -0.0595935000
_diffrn_orient_matrix_UB_13      -0.0121195000
_diffrn_orient_matrix_UB_21      0.0003378000
_diffrn_orient_matrix_UB_22      -0.0213053000
_diffrn_orient_matrix_UB_23      0.0338417000
_diffrn_orient_matrix_UB_31      -0.0528681000
_diffrn_orient_matrix_UB_32      0.0083550000
_diffrn_orient_matrix_UB_33      -0.0000995000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.257
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0646P)^2^+0.8311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3511
_reflns_number_total             6241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00793f2.cif
_cod_data_source_block           aks145
_cod_depositor_comments
'Adding full bibliography for 7159410--7159411.cif.'
_cod_database_code               7159410
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C20(H20), C24(H24), C17(H17), C16(H16), C13(H13), C21(H21), C14(H14),
 C23(H23), C2(H2), C9(H9), C26(H26), C30(H30), C27(H27), C29(H29), C5(H5),
 C7(H7), C3(H3), C8(H8), C4(H4)
2.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_res_checksum              67657
_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 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.659