Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo compounds.
He, Fengya; Sun, Ziyi; Li, Chenyue; Jiang, Zibin; Miao, Hui; Li, Qinglin; Wu, Chenggui; Organic & biomolecular chemistry 21 (2023) 8273–8278; doi:10.1039/d3ob01354e

data_7159580
_publ_section_title
;
 Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo
 compounds.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8273
_journal_page_last               8278
_journal_paper_doi               10.1039/d3ob01354e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dnkd1
_audit_creation_date             2022-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-12-05 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.344(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1369(7)
_cell_length_b                   11.3965(8)
_cell_length_c                   15.5049(11)
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1100
_cell_measurement_theta_min      2.2280
_cell_volume                     1772.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.873
_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    -50.00 107.00   0.50    4.58    --   24.18  22.00 -51.00  314
  2  \w     43.00 106.00   0.50    4.58    --   24.18 178.00  90.00  126
  3  \w     49.00 103.00   0.50    4.58    --   24.18 178.00 150.00  108
  4  \w     42.00 106.00   0.50    4.58    --   24.18 178.00 -60.00  128
  5  \w    -48.00 -23.00   0.50    4.58    --   24.18 -22.00 142.00   50
  6  \w   -110.00 -84.00   0.50    4.58    --  -23.24 -22.00 142.00   52
  7  \w    -17.00   8.00   0.50    4.58    --  -23.24 -99.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0343104000
_diffrn_orient_matrix_UB_12      0.0124797000
_diffrn_orient_matrix_UB_13      -0.0356724000
_diffrn_orient_matrix_UB_21      -0.0614839000
_diffrn_orient_matrix_UB_22      0.0125623000
_diffrn_orient_matrix_UB_23      -0.0263589000
_diffrn_orient_matrix_UB_31      0.0057695000
_diffrn_orient_matrix_UB_32      0.0597508000
_diffrn_orient_matrix_UB_33      0.0130035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12761
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         2.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             704
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0694P)^2^+0.2161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3140
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01354e2.cif
_cod_data_source_block           mh-01
_cod_depositor_comments
'Adding full bibliography for 7159580--7159581.cif.'
_cod_database_code               7159580
_shelx_shelxl_version_number     2018/3
_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:
 C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C15(H15), C10(H10), C9(H9), C16(H16), C18(H18), C17(H17), C3(H3),
 C5(H5), C2(H2), C1(H1), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              7794
_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 1.837
_oxdiff_exptl_absorpt_empirical_full_min 0.309