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_7126875
_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_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc251kjb
_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
;
2020-04-17 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.188(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3935(6)
_cell_length_b                   25.0493(16)
_cell_length_c                   8.8978(6)
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.4760
_cell_measurement_theta_min      5.5940
_cell_volume                     1536.5(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_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     25.00  71.00   1.00    1.00    --   40.98-125.00  60.00   46
  2  \w     35.00 113.00   1.00    1.00    --  106.95-125.00 -30.00   78
  3  \w     58.00  87.00   1.00    1.00    --   40.98-125.00-120.00   29
  4  \w     23.00  95.00   1.00    1.00    --   40.98-125.00-180.00   72
  5  \w     58.00 103.00   1.00    1.00    --  106.95 -95.00-180.00   45
  6  \w     60.00 157.00   1.00    1.00    --  106.95  15.00 120.00   97
  7  \w    104.00 156.00   1.00    1.00    --  106.95 125.00 150.00   52
  8  \w    105.00 158.00   1.00    1.00    --  106.95 125.00 -90.00   53
  9  \w     37.00 119.00   1.00    1.00    --  106.95-125.00 150.00   82
 10  \w   -116.00 -22.00   1.00    1.00    --  -40.98 -77.00 -30.00   94
;
_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      -0.1704711000
_diffrn_orient_matrix_UB_12      0.0359039000
_diffrn_orient_matrix_UB_13      -0.0032850000
_diffrn_orient_matrix_UB_21      0.1408590000
_diffrn_orient_matrix_UB_22      0.0357104000
_diffrn_orient_matrix_UB_23      0.1316737000
_diffrn_orient_matrix_UB_31      0.0312575000
_diffrn_orient_matrix_UB_32      0.0349249000
_diffrn_orient_matrix_UB_33      -0.1310381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5741
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.358
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74325
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0519P)^2^+0.6125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2488
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04309e2.cif
_cod_data_source_block           2l
_cod_depositor_comments
'Adding full bibliography for 7126875--7126877.cif.'
_cod_database_code               7126875
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.61
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C18(H18), C2(H2), C19(H19), C3(H3), C6(H6), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.682