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_7159411
_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         'C25 H17 F6 N O4'
_chemical_formula_sum            'C25 H17 F6 N O4'
_chemical_formula_weight         509.39
_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             2023-01-05
_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                 92.202(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0723(4)
_cell_length_b                   9.1985(3)
_cell_length_c                   16.7522(4)
_cell_measurement_reflns_used    11924
_cell_measurement_temperature    297.92
_cell_measurement_theta_max      23.9000
_cell_measurement_theta_min      2.5170
_cell_volume                     2320.85(11)
_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      air
_diffrn_ambient_temperature      297.92
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -102.00  67.00   0.50    1.82    --  -15.60   3.00   4.00  338
  2  \w    -68.00  99.00   0.50    1.82    --   16.22  -3.00-174.00  334
  3  \w    -70.00 -10.00   0.50    1.82    --  -15.60 125.00 -30.00  120
  4  \w    -89.00   9.00   0.50    1.82    --  -15.60 -30.00  90.00  196
  5  \w   -100.00   4.00   0.50    1.82    --  -15.60  -3.00-174.00  208
  6  \w    -52.00 -21.00   0.50    1.82    --  -15.60 125.00-180.00   62
  7  \w    -63.00 -11.00   0.50    1.82    --  -15.60 125.00  60.00  104
  8  \w    -85.00   9.00   0.50    1.82    --  -15.60 -45.00   0.00  188
  9  \w     11.00  45.00   0.50    1.82    --   16.22-125.00-150.00   68
 10  \w     32.00  66.00   0.50    1.82    --   16.22  45.00-150.00   68
 11  \w    -39.00 -13.00   0.50    1.82    --   16.22 130.00 131.90   52
 12  \w    -37.00  25.00   0.50    1.82    --   16.22 -94.00-150.00  124
 13  \w    -10.00  15.00   0.50    1.82    --   16.22   3.00   4.00   50
;
_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      0.0296031000
_diffrn_orient_matrix_UB_12      -0.0000166000
_diffrn_orient_matrix_UB_13      -0.0319038000
_diffrn_orient_matrix_UB_21      -0.0366047000
_diffrn_orient_matrix_UB_22      0.0018936000
_diffrn_orient_matrix_UB_23      -0.0278777000
_diffrn_orient_matrix_UB_31      0.0009292000
_diffrn_orient_matrix_UB_32      0.0770983000
_diffrn_orient_matrix_UB_33      0.0006970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81076
_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    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0876
_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^)+(0.1647P)^2^+1.4507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2657
_refine_ls_wR_factor_ref         0.2919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             4087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00793f2.cif
_cod_data_source_block           aks146
_cod_depositor_comments
'Adding full bibliography for 7159410--7159411.cif.'
_cod_database_code               7159411
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C23(H23), C19(H19), C10(H10), C8(H8), C9(H9), C22(H22),
 C13(H13), C20(H20), C17(H17), C14(H14), C16(H16)
;
_shelx_res_checksum              35954
_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.770