Asymmetric higher-order [10 + n] cycloadditions of palladium-containing 10π-cycloaddends
Li, Ao; Gao, Yang; Lu, Jian-Bin; Chen, Zhi-Chao; Du, Wei; Chen, Ying-Chun; Chemical Science 13 (2022) 9265–9270; doi:10.1039/D2SC02985E

data_1567414
_publ_section_title
;
 Asymmetric higher-order [10 + n] cycloadditions of palladium-containing
 10\p-cycloaddends
;
_journal_issue                   32
_journal_name_full               'Chemical Science'
_journal_page_first              9265
_journal_page_last               9270
_journal_paper_doi               10.1039/D2SC02985E
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H18 N2 O3'
_chemical_formula_sum            'C26 H18 N2 O3'
_chemical_formula_weight         406.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-24 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4861(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.34570(7)
_cell_length_b                   12.49324(16)
_cell_length_c                   29.7405(4)
_cell_measurement_reflns_used    9759
_cell_measurement_temperature    296.0(9)
_cell_measurement_theta_max      71.0010
_cell_measurement_theta_min      3.8020
_cell_volume                     2353.41(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.0(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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   -106.00 -13.00   1.00    1.86    --  -34.98 -38.00  90.00   93
  2  \w    -53.00  33.00   1.00    1.86    --  -34.98  57.00 120.00   86
  3  \w    -53.00  33.00   1.00    1.86    --  -34.98  57.00 -30.00   86
  4  \w    -33.00  53.00   1.00    1.86    --   34.98 -57.00-150.00   86
  5  \w     23.00  90.00   1.00    1.86    --   34.98-125.00   0.00   67
  6  \w    -33.00  53.00   1.00    1.86    --   34.98 -57.00 -60.00   86
  7  \w    -33.00  53.00   1.00    1.86    --   34.98 -57.00  90.00   86
  8  \w     16.00 103.00   1.00    1.86    --   34.98  57.00 -60.00   87
  9  \w     16.00 103.00   1.00    1.86    --   34.98  57.00  90.00   87
 10  \w    -33.00  53.00   1.00    1.86    --   34.98 -57.00  30.00   86
 11  \w     23.00  90.00   1.00    1.86    --   34.98-125.00-180.00   67
 12  \w     37.00 127.00   1.00    7.44    --  106.90 -45.00 -60.00   90
 13  \w     39.00 127.00   1.00    7.44    --  106.90 -61.00-180.00   88
 14  \w     87.00 175.00   1.00    7.44    --  106.90  61.00-120.00   88
 15  \w     37.00 110.00   1.00    7.44    --  106.90 -94.00 -60.00   73
 16  \w     37.00 110.00   1.00    7.44    --  106.90 -94.00  30.00   73
 17  \w     38.00 136.00   1.00    7.44    --  106.90 -77.00 -60.00   98
 18  \w     38.00 136.00   1.00    7.44    --  106.90 -77.00  60.00   98
 19  \w     37.00 127.00   1.00    7.44    --  106.90 -45.00  30.00   90
 20  \w     35.00 133.00   1.00    7.44    --  106.90 -30.00  60.00   98
 21  \w     36.00 113.00   1.00    7.44    --  106.90-111.00 -60.00   77
 22  \w     35.00 133.00   1.00    7.44    --  106.90 -30.00 120.00   98
 23  \w     57.00 151.00   1.00    7.44    --  106.90 178.00   0.00   94
 24  \w     35.00 152.00   1.00    7.44    --  106.90 -15.00-150.00  117
 25  \w     37.00 110.00   1.00    7.44    --  106.90 -94.00 150.00   73
 26  \w     16.00 103.00   1.00    1.86    --   34.98  57.00-150.00   87
 27  \w      6.00 104.00   1.00    1.86    --   34.98  77.00 150.00   98
 28  \w      6.00 102.00   1.00    1.86    --   34.98  77.00  30.00   96
 29  \w     16.00 103.00   1.00    1.86    --   34.98  57.00   0.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0394235000
_diffrn_orient_matrix_UB_12      0.0751410000
_diffrn_orient_matrix_UB_13      0.0407295000
_diffrn_orient_matrix_UB_21      -0.0373529000
_diffrn_orient_matrix_UB_22      0.0977461000
_diffrn_orient_matrix_UB_23      -0.0310490000
_diffrn_orient_matrix_UB_31      -0.2370255000
_diffrn_orient_matrix_UB_32      -0.0028816000
_diffrn_orient_matrix_UB_33      0.0084253000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25763
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.413
_diffrn_reflns_theta_min         3.839
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9006
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.0257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                8175
_reflns_number_total             9006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02985e2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 1567414.cif.'
_cod_database_code               1567414
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.770
_reflns_odcompleteness_completeness 99.95
_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:
 C007(H007), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00C,H00D), C00Q(H00E,H00F), C00Z(H00A,H00B), C01A(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00L(H00L), C00P(H00P), C00V(H00V), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C017(H017), C018(H018), C019(H019), C01B(H01F),
 C01C(H01C), C01D(H01D), C01E(H01E), C01G(H01G), C01I(H01I), C01J(H01J),
 C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P),
 C01Q(H01Q), C1(H1)
;
_shelx_res_checksum              69149
_shelx_fab_checksum              20126
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.126
_oxdiff_exptl_absorpt_empirical_full_min 0.682