Copper(I)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals.
Wang, Guanghui; Jia, Jian; Liu, Gang; Yu, Mingwu; Chu, Xiaoxiao; Liu, Xiguang; Zhao, Ximei; Chemical communications (Cambridge, England) 57 (2021) 11811–11814; doi:10.1039/d1cc05612c

data_7129217
_publ_section_title
;
 Copper(I)-catalyzed tandem synthesis of 2-acylquinolines from
 2-ethynylanilines and glyoxals.
;
_journal_issue                   89
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11811
_journal_page_last               11814
_journal_paper_doi               10.1039/d1cc05612c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H19 Cl N2 O'
_chemical_formula_sum            'C21 H19 Cl N2 O'
_chemical_formula_weight         350.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-04 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.243(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9491(3)
_cell_length_b                   8.2942(2)
_cell_length_c                   11.5280(4)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2860
_cell_measurement_theta_min      4.0710
_cell_volume                     886.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.986
_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    109.00 167.00   1.00    0.46    --  106.49  19.00  90.00   58
  2  \w    101.00 177.00   1.00    0.46    --  106.49  90.00 137.00   76
  3  \w     95.00 165.00   1.00    0.46    --  106.49 125.00-120.00   70
  4  \w    144.00 178.00   1.00    0.46    --  106.49  19.00-180.00   34
  5  \w     94.00 119.00   1.00    0.46    --  106.49  19.00-180.00   25
  6  \w    -39.00 -14.00   1.00    0.46    --  -86.25  38.00 -30.00   25
  7  \w    -69.00 -43.00   1.00    0.46    --  -86.25  90.00 137.00   26
  8  \w    -74.00 -28.00   1.00    0.10    --  -48.45  90.00 137.00   46
  9  \w   -123.00 -87.00   1.00    0.46    --  -86.25 -38.00  60.00   36
 10  \w   -159.00-126.00   1.00    0.46    --  -86.25 -38.00  60.00   33
 11  \w   -144.00-118.00   1.00    0.46    --  -86.25 -90.00  23.00   26
 12  \w   -117.00 -73.00   1.00    0.10    --  -48.45-125.00  60.00   44
 13  \w     11.00  66.00   1.00    0.10    --   48.45 -90.00  23.00   55
 14  \w    -18.00   8.00   1.00    0.10    --   48.45 -90.00  23.00   26
 15  \w     34.00 105.00   1.00    0.46    --  106.49 -77.00  30.00   71
 16  \w     62.00  87.00   1.00    0.46    --  106.49 -90.00  23.00   25
 17  \w    -23.00  40.00   1.00    0.10    --   48.45 -38.00 120.00   63
 18  \w     34.00  60.00   1.00    0.46    --  106.49 -57.00 -90.00   26
 19  \w     39.00  65.00   1.00    0.46    --  106.49 -57.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0993981000
_diffrn_orient_matrix_UB_12      -0.0274418000
_diffrn_orient_matrix_UB_13      0.0742716000
_diffrn_orient_matrix_UB_21      0.0686004000
_diffrn_orient_matrix_UB_22      -0.1671548000
_diffrn_orient_matrix_UB_23      0.0406809000
_diffrn_orient_matrix_UB_31      0.1140841000
_diffrn_orient_matrix_UB_32      0.0761312000
_diffrn_orient_matrix_UB_33      0.1156356000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4700
_diffrn_reflns_point_group_measured_fraction_full 0.764
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.991
_diffrn_reflns_theta_min         4.114
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.038(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0458P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.458
_reflns_Friedel_fraction_full    0.519
_reflns_Friedel_fraction_max     0.525
_reflns_number_gt                2364
_reflns_number_total             2445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05612c2.cif
_cod_data_source_block           20210629pmf-1
_cod_database_code               7129217
_shelxl_version_number           2013-4
_diffrn_oxdiff_digest_frames
;
01ab8c1a49781bbfd656f82170ca4e485b00791e7ca
;
_diffrn_oxdiff_digest_hkl
;
0191ab2e84bda9e05a63d1c066bdac154d4f48
;
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00F(H00A,H00D), C00I(H00F,H00G), C00J(H00I,H00J), C00K(H00K,H00L), C00N(H00O,
 H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00C(H00C), C00E(H00E), C00H(H00H), C00L(H00M),
 C00M(H00N), C00O(H00Q), C00P(H00R)
;
_shelx_res_checksum              87881
_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 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.505