Catalytic regio- and stereoselective intermolecular [5+2] cycloaddition via conjugative activation of oxidopyrylium.
Zhang, Ling; Shi, Qiu; Cao, Tongxiang; Zhu, Shifa; Chemical communications (Cambridge, England) 56 (2020) 9533–9536; doi:10.1039/d0cc04309e

data_7126876
_publ_section_title
;
 Catalytic regio- and stereoselective intermolecular [5+2] cycloaddition
 via conjugative activation of oxidopyrylium.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9533
_journal_page_last               9536
_journal_paper_doi               10.1039/d0cc04309e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_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             2019-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.123(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9097(6)
_cell_length_b                   20.9012(19)
_cell_length_c                   16.8201(14)
_cell_measurement_reflns_used    2330
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.0920
_cell_measurement_theta_min      2.6060
_cell_volume                     1716.2(3)
_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 (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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.949
_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    -56.00  26.00   1.00    1.00    --  -40.73  38.00 -90.00   82
  2  \w      2.00  46.00   1.00    1.00    --   40.73 -99.00  90.00   44
  3  \w     34.00 135.00   1.00    1.00    --  106.95 -30.00  30.00  101
  4  \w     59.00  97.00   1.00    1.00    --   40.73-125.00-120.00   38
  5  \w     26.00 105.00   1.00    1.00    --  106.95 -95.00-150.00   79
  6  \w    110.00 137.00   1.00    1.00    --  106.95  45.00-180.00   27
  7  \w     95.00 122.00   1.00    1.00    --  106.95 125.00 -90.00   27
  8  \w     98.00 178.00   1.00    1.00    --  106.95 123.00  54.00   80
  9  \w     61.00 125.00   1.00    1.00    --  106.95 -45.00 150.00   64
 10  \w     41.00  97.00   1.00    1.00    --  106.95 -95.00  60.00   56
 11  \w   -111.00 -60.00   1.00    1.00    --  -40.73 -57.00 -60.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064178000
_diffrn_orient_matrix_UB_12      0.0710222000
_diffrn_orient_matrix_UB_13      0.0241484000
_diffrn_orient_matrix_UB_21      -0.0894730000
_diffrn_orient_matrix_UB_22      0.0185592000
_diffrn_orient_matrix_UB_23      -0.0875877000
_diffrn_orient_matrix_UB_31      -0.3026063000
_diffrn_orient_matrix_UB_32      -0.0069786000
_diffrn_orient_matrix_UB_33      0.0149212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6214
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.741
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33640
_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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0795P)^2^+0.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.401
_reflns_Friedel_fraction_max     0.375
_reflns_number_gt                4143
_reflns_number_total             4638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04309e2.cif
_cod_data_source_block           yinduo
_cod_depositor_comments
'Adding full bibliography for 7126875--7126877.cif.'
_cod_database_code               7126876
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15B(H15B), C13(H13), C14(H14), C13B(H13B), C14B(H14B), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C8B(H8B), C2(H2), C21(H21), C21B(H21B), C4(H4), C6(H6), C3(H3),
 C18(H18), C6B(H6B), C2B(H2B), C4B(H4B), C19(H19), C20(H20), C20B(H20B),
 C18B(H18B), C3B(H3B), C5(H5), C19B(H19B), C5B(H5B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C23B(H23D,H23E,H23F), C22B(H22D,
 H22E,H22F)
;
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.560