Visible-light-enabled cascade cross-dehydrogenative-coupling/cyclization to construct α-chromone substituted α-amino acid derivatives.
Zhu, Zhi-Qiang; Hu, Jia-Yu; Xie, Zong-Bo; Le, Zhang-Gao; Chemical communications (Cambridge, England) 60 (2023) 106–109; doi:10.1039/d3cc04107g

data_7132390
_publ_section_title
;
 Visible-light-enabled cascade cross-dehydrogenative-coupling/cyclization
 to construct &#x3b1;-chromone substituted &#x3b1;-amino acid derivatives.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              106
_journal_page_last               109
_journal_paper_doi               10.1039/d3cc04107g
_journal_volume                  60
_journal_year                    2023
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C19 H17 N2 O3'
_chemical_formula_weight         321.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-24 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.169(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6169(4)
_cell_length_b                   15.6243(6)
_cell_length_c                   23.3222(12)
_cell_measurement_reflns_used    6128
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8360
_cell_measurement_theta_min      3.3880
_cell_volume                     4221.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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     90.00 128.00   0.50    0.50    --   42.30  54.00  30.00   76
  2  \w     83.00 130.00   0.50    0.50    --   42.30  77.00-150.00   94
  3  \w    -25.00  56.00   0.50    0.50    --   42.30 -65.00 -60.00  162
  4  \w     -6.00  68.00   0.50    0.50    --   42.30 -82.00  60.00  148
  5  \w    -47.00  17.00   0.50    0.50    --   42.30 -65.00 120.00  128
  6  \w    -10.00  15.00   0.50    0.50    --   42.30 -82.00 -30.00   50
  7  \w     32.00  63.00   0.50    0.50    --   42.30  54.00-180.00   62
  8  \w     36.00  61.00   0.50    0.50    --   42.30 -77.00-180.00   50
  9  \w     19.00  56.00   0.50    0.50    --   42.30  77.00-150.00   74
 10  \w    -25.00  56.00   0.50    0.50    --   42.30 -65.00 -90.00  162
 11  \w    -46.00  -9.00   0.50    0.50    --   42.30 -82.00  60.00   74
 12  \w     34.00  76.00   0.50    0.50    --   42.30  54.00  30.00   84
 13  \w     70.00 132.00   0.50    0.50    --   42.30  54.00-180.00  124
 14  \w     45.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00   50
 15  \w    -39.00  27.00   0.50    0.50    --   42.30 -77.00-180.00  132
 16  \w     20.00  59.00   0.50    0.50    --   42.30  77.00 -90.00   78
 17  \w     13.00  70.00   0.50    0.50    --   42.30 -82.00 150.00  114
 18  \w    100.00 126.00   0.50    0.50    --   42.30  77.00 -90.00   52
 19  \w     12.00  58.00   0.50    0.50    --   93.70 -33.00-150.00   92
 20  \w     48.00 101.00   0.50    0.50    --   93.70 -82.00-180.00  106
 21  \w      4.00  83.00   0.50    0.50    --   93.70 -82.00   0.00  158
 22  \w     73.00 114.00   0.50    0.50    --   93.70 -82.00 -30.00   82
 23  \w    108.00 157.00   0.50    0.50    --   93.70  59.00 150.00   98
 24  \w     71.00  97.00   0.50    0.50    --   93.70 -82.00-150.00   52
 25  \w     33.00  73.00   0.50    0.50    --   93.70 -82.00 -90.00   80
 26  \w     17.00  54.00   0.50    0.50    --   93.70   8.00 120.00   74
 27  \w      9.00 101.00   0.50    0.50    --   93.70 -82.00-120.00  184
 28  \w    115.00 182.00   0.50    0.50    --   93.70  68.00-120.00  134
 29  \w      5.00  96.00   0.50    0.50    --   93.70 -82.00  60.00  182
 30  \w     85.00 111.00   0.50    0.50    --   93.70 -33.00-150.00   52
 31  \w     51.00 120.00   0.50    0.50    --   93.70 -82.00 120.00  138
 32  \w      4.00  73.00   0.50    0.50    --   93.70 -59.00 120.00  138
 33  \w      4.00  93.00   0.50    0.50    --   93.70 -82.00  90.00  178
 34  \w     75.00 145.00   0.50    0.50    --   93.70  33.00-150.00  140
 35  \w      7.00  96.00   0.50    0.50    --   93.70 -82.00 -60.00  178
 36  \w     69.00 183.00   0.50    0.50    --   93.70   8.00 120.00  228
 37  \w     18.00  66.00   0.50    0.50    --   93.70 -82.00  30.00   96
 38  \w     75.00 101.00   0.50    0.50    --   93.70 -82.00  30.00   52
 39  \w     13.00  40.00   0.50    0.50    --   93.70 -42.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0746867000
_diffrn_orient_matrix_UB_12      -0.0778286000
_diffrn_orient_matrix_UB_13      0.0189513000
_diffrn_orient_matrix_UB_21      0.0501581000
_diffrn_orient_matrix_UB_22      0.0500879000
_diffrn_orient_matrix_UB_23      0.0529666000
_diffrn_orient_matrix_UB_31      -0.0979280000
_diffrn_orient_matrix_UB_32      -0.0337833000
_diffrn_orient_matrix_UB_33      0.0350340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.723
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_F_000             1352
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1168
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3166
_refine_ls_wR_factor_ref         0.3320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2759
_reflns_number_total             3844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04107g2.cif
_cod_data_source_block           20220117_auto
_cod_depositor_comments          'Adding full bibliography for 7132390.cif.'
_cod_database_code               7132390
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01c68e6de2693625d43b8bc894860a3930000309c47
;
_diffrn_oxdiff_digest_hkl
;
01159673d3759cf470d77b807392e3c5cd5141
;
_reflns_odcompleteness_completeness 99.90
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N16(H16), C10(H10), C23(H23), C22(H22), C4(H4), C19(H19), C7(H7), C20(H20),
 C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              59902
_shelx_hkl_checksum              93196
_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 6.752
_oxdiff_exptl_absorpt_empirical_full_min 0.422