Copper-catalyzed multicomponent assembly of γ-butenolides <i>via</i> the interception of carbonyl ylides with iminium ions.
Zhang, Mengchu; Yu, Sifan; Hua, Ruyu; Zhang, Dan; Qiu, Huang; Hu, Wenhao; Organic & biomolecular chemistry 21 (2023) 783–788; doi:10.1039/d2ob02075k

data_7159057
_publ_section_title
;
 Copper-catalyzed multicomponent assembly of &#x3b3;-butenolides
 <i>via</i> the interception of carbonyl ylides with iminium ions.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              783
_journal_page_last               788
_journal_paper_doi               10.1039/d2ob02075k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C27 H19 Cl O3'
_chemical_formula_sum            'C27 H19 Cl O3'
_chemical_formula_weight         426.87
_chemical_name_systematic
3-(2-chlorophenyl)-5-(5-oxo-1,5-diphenylpent-1-yn-3-yl)furan-2(5H)-one
_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             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.697(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4913(2)
_cell_length_b                   11.5055(2)
_cell_length_c                   19.8764(4)
_cell_measurement_reflns_used    7176
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.7810
_cell_measurement_theta_min      4.4290
_cell_volume                     2159.82(7)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_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    -57.00 -27.00   0.50    3.00    -- -100.00  61.00  60.00   60
  2  \w    -56.00 -31.00   0.50    3.00    -- -100.00  61.00   0.00   50
  3  \w    -27.00  15.00   0.50    0.50    --  -46.62  30.00   7.00   84
  4  \w    -57.00 -27.00   0.50    3.00    -- -100.00  61.00  90.00   60
  5  \w    -55.00 -27.00   0.50    3.00    -- -100.00  61.00 120.00   56
  6  \w    -65.00 -28.00   0.50    3.00    -- -100.00  61.00 150.00   74
  7  \w    -39.00  22.00   0.50    0.50    --  -46.62  38.00 150.00  122
  8  \w    -12.00  18.00   0.50    0.50    --  -46.62  19.00 150.00   60
  9  \w     38.00 112.00   0.50    0.50    --   46.62  30.00   7.00  148
 10  \w     94.00 178.00   0.50    3.00    --  105.44  30.00   7.00  168
 11  \w     57.00  84.00   0.50    3.00    --  105.44 -94.00  60.00   54
 12  \w     68.00 107.00   0.50    3.00    --  105.44 -77.00  30.00   78
 13  \w     41.00  66.00   0.50    3.00    --  105.44 -61.00  90.00   50
 14  \w     36.00  64.00   0.50    3.00    --  105.44 -77.00  30.00   56
 15  \w     35.00  68.00   0.50    3.00    --  105.44 -61.00 -60.00   66
 16  \w     33.00 105.00   0.50    3.00    --  105.44 -94.00-120.00  144
 17  \w     34.00  73.00   0.50    3.00    --  105.44 -61.00-120.00   78
 18  \w     34.00  73.00   0.50    3.00    --  105.44 -61.00 -90.00   78
 19  \w     34.00  73.00   0.50    3.00    --  105.44 -61.00-150.00   78
 20  \w    -20.00   5.00   0.50    0.50    --   46.62 -30.00-153.00   50
 21  \w   -106.00 -35.00   0.50    0.50    --  -46.62 -30.00-153.00  142
 22  \w    -67.00 -28.00   0.50    3.00    -- -100.00  61.00-180.00   78
 23  \w    -63.00 -27.00   0.50    3.00    -- -100.00  77.00-180.00   72
 24  \w    -82.00 -40.00   0.50    3.00    -- -100.00 125.00 -90.00   84
 25  \w    -99.00 -74.00   0.50    3.00    -- -100.00  77.00-180.00   50
 26  \w   -114.00 -89.00   0.50    3.00    -- -100.00 -30.00-153.00   50
 27  \w   -119.00 -94.00   0.50    0.50    --  -46.62-125.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520803000
_diffrn_orient_matrix_UB_12      0.0153086000
_diffrn_orient_matrix_UB_13      -0.0753855000
_diffrn_orient_matrix_UB_21      0.1415876000
_diffrn_orient_matrix_UB_22      -0.0484738000
_diffrn_orient_matrix_UB_23      -0.0195723000
_diffrn_orient_matrix_UB_31      -0.0619032000
_diffrn_orient_matrix_UB_32      -0.1238933000
_diffrn_orient_matrix_UB_33      -0.0016563000
_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  0.0709
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.100
_diffrn_reflns_theta_min         4.446
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77929
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1188P)^2^+0.9771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3698
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02075k2.cif
_cod_data_source_block           zhangmch_210125_3
_cod_depositor_comments
'Adding full bibliography for 7159057--7159059.cif.'
_cod_database_code               7159057
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.80
_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 Ternary CH refined with riding coordinates:
 C12(H12), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C25(H25), C6(H6), C21(H21), C5(H5), C24(H24), C23(H23), C3(H3),
 C4(H4), C22(H22), C29(H29), C31(H31), C30(H30), C27(H27), C28(H28)
;
_shelx_res_checksum              71939
_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 3.642
_oxdiff_exptl_absorpt_empirical_full_min 0.655