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_7159058
_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 H20 O3'
_chemical_formula_sum            'C27 H20 O3'
_chemical_formula_weight         392.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.115(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.3680(5)
_cell_length_b                   13.3744(3)
_cell_length_c                   12.7991(3)
_cell_measurement_reflns_used    4615
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8920
_cell_measurement_theta_min      3.7780
_cell_volume                     3984.21(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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    -32.00  -5.00   0.50    0.10    --  -46.62  27.00 -66.00   54
  2  \w   -121.00 -32.00   0.50    0.10    --  -46.62 -27.00 130.00  178
  3  \w     58.00  88.00   0.50    0.10    --   46.62  27.00 -66.00   60
  4  \w    -18.00  60.00   0.50    0.10    --   46.62 -27.00 130.00  156
  5  \w   -174.00 -87.00   0.50    0.50    -- -100.00 -27.00 130.00  174
  6  \w   -106.00 -25.00   0.50    0.50    -- -100.00  27.00 -66.00  162
  7  \w     52.00  77.00   0.50    0.50    --  107.00 -27.00 130.00   50
  8  \w    101.00 134.00   0.50    0.50    --  107.00  27.00 -66.00   66
  9  \w    -14.00  27.00   0.50    0.10    --  -46.62  38.00 -60.00   82
 10  \w     33.00  95.00   0.50    0.10    --   46.62-125.00   0.00  124
 11  \w    -88.00 -30.00   0.50    0.50    -- -100.00  77.00 120.00  116
 12  \w   -122.00 -92.00   0.50    0.50    -- -100.00  77.00 120.00   60
 13  \w     34.00  89.00   0.50    0.50    --  107.00 -94.00 -60.00  110
 14  \w     37.00 123.00   0.50    0.50    --  107.00 -30.00 -60.00  172
 15  \w     94.00 175.00   0.50    0.50    --  107.00  61.00-120.00  162
 16  \w     32.00 123.00   0.50    0.50    --  107.00 -15.00 -90.00  182
 17  \w     73.00 103.00   0.50    0.50    --  107.00 -94.00 -30.00   60
 18  \w     83.00 108.00   0.50    0.50    --  107.00 -94.00-150.00   50
 19  \w     44.00 104.00   0.50    0.50    --  107.00 -94.00  90.00  120
;
_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      -0.0214765000
_diffrn_orient_matrix_UB_12      -0.0344831000
_diffrn_orient_matrix_UB_13      0.1044966000
_diffrn_orient_matrix_UB_21      -0.0597188000
_diffrn_orient_matrix_UB_22      -0.0214343000
_diffrn_orient_matrix_UB_23      -0.0565252000
_diffrn_orient_matrix_UB_31      0.0187686000
_diffrn_orient_matrix_UB_32      -0.1078042000
_diffrn_orient_matrix_UB_33      -0.0221852000
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14734
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.816
_diffrn_reflns_theta_min         3.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00015(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0567P)^2^+1.4726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             4057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02075k2.cif
_cod_data_source_block           zhangmch_201103
_cod_depositor_comments
'Adding full bibliography for 7159057--7159059.cif.'
_cod_database_code               7159058
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C9(H9), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C6(H6), C2(H2), C16(H16), C5(H5), C14(H14), C18(H18), C24(H24),
 C17(H17), C3(H3), C15(H15), C20(H20), C4(H4), C23(H23), C21(H21), C22(H22)
;
_shelx_res_checksum              84046
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.895