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_7159059
_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         'C25 H19 N O5'
_chemical_formula_sum            'C25 H19 N O5'
_chemical_formula_weight         413.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-19 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                104.255(2)
_cell_angle_beta                 103.185(3)
_cell_angle_gamma                102.624(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6080(3)
_cell_length_b                   10.7491(3)
_cell_length_c                   13.6882(4)
_cell_measurement_reflns_used    6091
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7540
_cell_measurement_theta_min      4.6890
_cell_volume                     1010.59(6)
_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 (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.947
_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   -107.00 -82.00   0.50    0.05    --  -46.62-163.00-132.00   50
  2  \w    -74.00 -38.00   0.50    0.05    --  -46.62 116.00 104.00   72
  3  \w     41.00  89.00   0.50    0.05    --   46.62-116.00  16.00   96
  4  \w     77.00 107.00   0.50    0.05    --   46.62-163.00-132.00   60
  5  \w     51.00 103.00   0.50    0.05    --   46.62 163.00-107.00  104
  6  \w   -138.00-112.00   0.50    0.10    -- -100.00-116.00  16.00   52
  7  \w   -111.00 -48.00   0.50    0.10    -- -100.00 116.00 104.00  126
  8  \w    -87.00 -48.00   0.50    0.10    -- -100.00 163.00-107.00   78
  9  \w   -130.00 -92.00   0.50    0.10    -- -100.00 163.00-107.00   76
 10  \w   -128.00-103.00   0.50    0.10    -- -100.00-163.00-132.00   50
 11  \w     91.00 117.00   0.50    0.10    --  105.44 163.00-107.00   52
 12  \w     98.00 124.00   0.50    0.10    --  105.44 116.00 104.00   52
 13  \w     91.00 142.00   0.50    0.10    --  105.44-163.00-132.00  102
 14  \w     34.00 109.00   0.50    0.10    --  105.44-116.00  16.00  150
 15  \w    -79.00 -54.00   0.50    0.05    --  -46.62 163.00-107.00   50
 16  \w   -117.00 -82.00   0.50    0.05    --  -46.62-125.00  60.00   70
 17  \w   -119.00 -25.00   0.50    0.05    --  -46.62 -77.00   0.00  188
 18  \w   -119.00 -90.00   0.50    0.05    --  -46.62-125.00 150.00   58
 19  \w   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 -30.00   92
 20  \w   -118.00 -76.00   0.50    0.05    --  -46.62-125.00-180.00   84
 21  \w     89.00 120.00   0.50    0.05    --   46.62  38.00 -30.00   62
 22  \w   -120.00 -82.00   0.50    0.10    -- -100.00 -61.00 -60.00   76
 23  \w   -162.00-130.00   0.50    0.10    -- -100.00 -61.00 -60.00   64
 24  \w   -108.00 -82.00   0.50    0.10    -- -100.00 -61.00  90.00   52
 25  \w    -70.00 -27.00   0.50    0.10    -- -100.00  61.00 -60.00   86
 26  \w   -117.00 -78.00   0.50    0.10    -- -100.00  61.00 -60.00   78
 27  \w   -172.00-125.00   0.50    0.10    -- -100.00 -61.00  90.00   94
 28  \w    -98.00 -29.00   0.50    0.10    -- -100.00  61.00 120.00  138
 29  \w     90.00 150.00   0.50    0.10    --  105.44 125.00  60.00  120
 30  \w     31.00 121.00   0.50    0.10    --  105.44 -30.00  90.00  180
 31  \w     34.00 120.00   0.50    0.10    --  105.44 -45.00 -30.00  172
 32  \w    117.00 176.00   0.50    0.10    --  105.44  30.00-120.00  118
 33  \w     42.00  97.00   0.50    0.10    --  105.44 -30.00 -60.00  110
 34  \w     33.00  93.00   0.50    0.10    --  105.44 -94.00-150.00  120
 35  \w     71.00 105.00   0.50    0.10    --  105.44 -94.00-120.00   68
 36  \w     60.00 120.00   0.50    0.10    --  105.44 -45.00 150.00  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      -0.1861286000
_diffrn_orient_matrix_UB_12      -0.1122894000
_diffrn_orient_matrix_UB_13      -0.0604616000
_diffrn_orient_matrix_UB_21      0.0500163000
_diffrn_orient_matrix_UB_22      -0.0095763000
_diffrn_orient_matrix_UB_23      -0.1039826000
_diffrn_orient_matrix_UB_31      0.1005686000
_diffrn_orient_matrix_UB_32      -0.1057869000
_diffrn_orient_matrix_UB_33      0.0181983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11939
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.086
_diffrn_reflns_theta_min         4.714
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90227
_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    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0021(5)
_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   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0564P)^2^+0.2797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3357
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02075k2.cif
_cod_data_source_block           zhangmch_02_200821
_cod_depositor_comments
'Adding full bibliography for 7159057--7159059.cif.'
_cod_original_cell_volume        1010.58(6)
_cod_database_code               7159059
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.828
_diffrn_oxdiff_digest_frames
;
01dd42b14ffe357d95f4bc33780d1d7e3e00050666e
;
_diffrn_oxdiff_digest_hkl
;
015f89d9fab975cdedb965be2bc635ba21b1d5
;
_reflns_odcompleteness_completeness 99.67
_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:
 C21(H21), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C5(H5), C30(H30), C6(H6), C3(H3), C15(H15), C26(H26),
 C29(H29), C28(H28), C27(H27), C19(H19), C18(H18), C17(H17), C16(H16)
;
_shelx_res_checksum              46077
_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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.828