Organocatalytic enantio- and diastereoselective assembly of cyclopropane-incorporated polycyclic molecules <i>via</i> isobenzopyrylium ions.
Liu, Shuxuan; Zhang, Chaoshen; Han, Zhengyu; Huang, Hai; Sun, Jianwei; Chemical science 15 (2024) 15274–15279; doi:10.1039/d4sc03746d

data_1572384
_publ_section_title
;
 Organocatalytic enantio- and diastereoselective assembly of
 cyclopropane-incorporated polycyclic molecules <i>via</i>
 isobenzopyrylium ions.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              15274
_journal_page_last               15279
_journal_paper_doi               10.1039/d4sc03746d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H18 O'
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-10-21
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2024-05-19 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.33817(7)
_cell_length_b                   10.45428(8)
_cell_length_c                   14.51868(10)
_cell_measurement_reflns_used    9042
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9520
_cell_measurement_theta_min      4.2760
_cell_volume                     1569.152(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    108.00 174.00   1.00    5.00    --  112.00 111.00   0.00   66
  2  \w     20.00 116.00   1.00    2.00    --   41.13  37.00-180.00   96
  3  \w     15.00 111.00   1.00    2.00    --   41.13  57.00  60.00   96
  4  \w     40.00  97.00   1.00    2.00    --   41.13-125.00-180.00   57
  5  \w    -19.00  73.00   1.00    2.00    --   41.13 -77.00 -90.00   92
  6  \w     37.00 140.00   1.00    5.00    --  112.00 -30.00  30.00  103
  7  \w     37.00 109.00   1.00    5.00    --  112.00-111.00 -60.00   72
  8  \w     50.00 109.00   1.00    5.00    --  112.00-111.00-150.00   59
  9  \w    111.00 164.00   1.00    5.00    --  112.00 111.00 -30.00   53
 10  \w     86.00 176.00   1.00    5.00    --  112.00  45.00  60.00   90
 11  \w     43.00 108.00   1.00    5.00    --  112.00-111.00  30.00   65
 12  \w     39.00 140.00   1.00    5.00    --  112.00 -30.00-120.00  101
 13  \w     37.00 141.00   1.00    5.00    --  112.00 -77.00  30.00  104
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0392724000
_diffrn_orient_matrix_UB_12      -0.1124585000
_diffrn_orient_matrix_UB_13      0.0626094000
_diffrn_orient_matrix_UB_21      -0.0689853000
_diffrn_orient_matrix_UB_22      0.0939258000
_diffrn_orient_matrix_UB_23      0.0653330000
_diffrn_orient_matrix_UB_31      -0.1260468000
_diffrn_orient_matrix_UB_32      -0.0164154000
_diffrn_orient_matrix_UB_33      -0.0553849000
_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  0.0139
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.904
_diffrn_reflns_theta_min         5.214
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0035(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0503P)^2^+0.2747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3215
_reflns_number_total             3252
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03746d2.cif
_cod_data_source_block           sliu3cult_auto
_cod_depositor_comments          'Adding full bibliography for 1572384.cif.'
_cod_original_cell_volume        1569.15(2)
_cod_database_code               1572384
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 H18 O'
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.888
_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:
 C1(H1), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              53931
_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 1.645
_oxdiff_exptl_absorpt_empirical_full_min 0.855