Diastereoselective construction of a library of structural bispiro[butyrolactone/valerolactone–pyrrolidine–indanedione] hybrids via 1,3-dipolar cycloaddition reactions
Zhang, Lei; Quan, Wei; Liu, Ren-Ming; Tian, You-Ping; Pan, Bo-Wen; Liu, Xiong-Li; New Journal of Chemistry 46 (2022) 11975–11979; doi:10.1039/D2NJ01571D

data_7061624
_publ_section_title
;
 Diastereoselective construction of a library of structural
 bispiro[butyrolactone/valerolactone--pyrrolidine--indanedione] hybrids
 via 1,3-dipolar cycloaddition reactions
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11975
_journal_page_last               11979
_journal_paper_doi               10.1039/D2NJ01571D
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H29 N O4'
_chemical_formula_sum            'C28 H29 N O4'
_chemical_formula_weight         443.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-21 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.1259(2)
_cell_length_b                   8.1259(2)
_cell_length_c                   67.712(2)
_cell_measurement_reflns_used    9665
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.9090
_cell_measurement_theta_min      2.5890
_cell_volume                     4471.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_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    -69.00  31.50   0.75    0.75    --  -40.73  57.00   0.00  134
  2  \w    -25.00  25.25   0.75    0.75    --  -40.73  38.00-180.00   67
  3  \w     58.00  84.25   0.75    0.75    --   40.73-125.00  30.00   35
  4  \w     42.00  78.00   0.75    0.75    --   40.73 -99.00 120.00   48
  5  \w     96.00 131.25   0.75    0.75    --  107.58 -45.00 150.00   47
  6  \w     84.00 166.50   0.75    0.75    --  107.58  30.00 150.00  110
  7  \w     66.00 129.00   0.75    0.75    --  107.58 -77.00 -30.00   84
  8  \w     68.00 131.00   0.75    0.75    --  107.58 -61.00-180.00   84
  9  \w     40.00 106.00   0.75    0.75    --  107.58 -45.00 -60.00   88
 10  \w     42.00 127.50   0.75    0.75    --  107.58 -61.00  60.00  114
 11  \w     92.00 120.50   0.75    0.75    --  107.58-125.00 120.00   38
 12  \w     36.00  83.25   0.75    0.75    --  107.58 -45.00 150.00   63
 13  \w     34.00 168.25   0.75    0.75    --  107.58   0.00 120.00  179
 14  \w     40.00  65.50   0.75    0.75    --  107.58-125.00 120.00   34
 15  \w     34.00 118.00   0.75    0.75    --  107.58-125.00   0.00  112
 16  \w     41.00 101.00   0.75    0.75    --  107.58 -95.00-180.00   80
 17  \w    -64.00   4.25   0.75    0.75    --  -40.73  38.00 150.00   91
 18  \w   -107.00 -21.50   0.75    0.75    --  -40.73 -57.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       78
_diffrn_reflns_limit_l_min       -84
_diffrn_reflns_number            30219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.293
_diffrn_reflns_theta_min         2.610
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_extinction_coef       0.00108(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0097P)^2^+4.5898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.600
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4302
_reflns_number_total             4505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01571d2.cif
_cod_data_source_block           4ea
_cod_original_cell_volume        4471.0(3)
_cod_database_code               7061624
_shelx_shelxl_version_number     2017/1
_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), C17(H17), C18(H18), C23(H23), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C19(H19A,
 H19B), C20(H20A,H20B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              24173
_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
;