Harnessing structurally unbiased ortho-benzoquinone monoimine for biomimetic oxidative [4+2] cycloaddition with enamines.
Bashir, Muhammad Adnan; Zuo, Honghua; Lu, Xunbo; Wu, Yuzhou; Zhong, Fangrui; Chemical communications (Cambridge, England) 56 (2020) 5965–5968; doi:10.1039/d0cc01813a

data_7126374
_publ_section_title
;
 Harnessing structurally unbiased ortho-benzoquinone monoimine for
 biomimetic oxidative [4+2] cycloaddition with enamines.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5965
_journal_page_last               5968
_journal_paper_doi               10.1039/d0cc01813a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H23 N3 O5'
_chemical_formula_sum            'C21 H23 N3 O5'
_chemical_formula_weight         397.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-14 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                72.265(4)
_cell_angle_beta                 77.347(4)
_cell_angle_gamma                82.211(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9699(3)
_cell_length_b                   10.2021(3)
_cell_length_c                   14.9823(8)
_cell_measurement_reflns_used    9478
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4710
_cell_measurement_theta_min      3.1180
_cell_volume                     987.37(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.975
_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    -20.00  46.00   0.50    0.50    --    0.00  57.00 150.00  132
  2  \w    -10.00  27.00   0.50    0.50    --    0.00 -77.00 150.00   74
  3  \w    -89.00 -31.00   0.50    0.50    --    0.00 -38.00 -30.00  116
  4  \w     51.00  83.00   0.50    0.50    --    0.00  38.00-120.00   64
  5  \w     -5.00  25.00   0.50    0.50    --    0.00 -77.00  30.00   60
  6  \w     56.00  84.00   0.50    0.50    --    0.00  57.00 150.00   56
  7  \w    -45.00 -12.00   0.50    0.50    --    0.00 -77.00 150.00   66
  8  \w    -19.00  16.00   0.50    0.50    --    0.00 -38.00 -30.00   70
  9  \w    -14.00  45.00   0.50    0.50    --    0.00  38.00-120.00  118
 10  \w    -13.00  60.00   0.50    0.50    --    0.00  38.00   0.00  146
 11  \w     43.00  88.00   0.50    0.50    --    0.00  38.00 -90.00   90
 12  \w    -36.00 -11.00   0.50    0.50    --    0.00 -77.00  30.00   50
 13  \w     76.00 144.00   0.50    0.50    --   94.60  47.00  -0.87  136
 14  \w     71.00 179.00   0.50    0.50    --   94.60  64.00 156.95  216
 15  \w     69.00  95.00   0.50    0.50    --   94.60  67.00-137.28   52
 16  \w    134.00 160.00   0.50    0.50    --   94.60  58.00 -95.51   52
 17  \w     72.00  98.00   0.50    0.50    --   94.60  58.00 -95.51   52
 18  \w    103.00 129.00   0.50    0.50    --   94.60  71.00  61.52   52
 19  \w    147.00 173.00   0.50    0.50    --   94.60  64.00-111.77   52
 20  \w    104.00 184.00   0.50    0.50    --   94.60  73.00 -90.71  160
 21  \w     68.00  95.00   0.50    0.50    --   94.60  73.00 -90.71   54
 22  \w    156.00 182.00   0.50    0.50    --   94.60  63.00 -45.96   52
 23  \w     67.00  94.00   0.50    0.50    --   94.60  71.00 117.73   54
 24  \w     68.00 121.00   0.50    0.50    --   94.60  70.00 135.74  106
 25  \w    124.00 172.00   0.50    0.50    --   94.60  70.00 135.74   96
 26  \w     68.00  94.00   0.50    0.50    --   94.60  69.00-177.00   52
 27  \w      6.00 106.00   0.50    0.50    --   94.60 -61.00 -60.00  200
 28  \w      6.00 116.00   0.50    0.50    --   94.60 -82.00-180.00  220
 29  \w    100.00 126.00   0.50    0.50    --   94.60  74.00  31.41   52
 30  \w     30.00 124.00   0.50    0.50    --   94.60 -82.00  30.00  188
 31  \w     67.00  92.00   0.50    0.50    --   94.60  74.00  31.41   50
 32  \w    115.00 147.00   0.50    0.50    --   94.60  63.00 -45.96   64
 33  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  61.52   52
 34  \w      7.00 120.00   0.50    0.50    --   94.60 -82.00 -60.00  226
 35  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -89.35   52
 36  \w     71.00 144.00   0.50    0.50    --   94.60  62.00  31.07  146
 37  \w     71.00 106.00   0.50    0.50    --   94.60  63.00 -45.96   70
 38  \w     71.00  97.00   0.50    0.50    --   94.60  61.00   0.00   52
 39  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-180.00   50
 40  \w     73.00 154.00   0.50    0.50    --   94.60  61.00  60.00  162
 41  \w     71.00  98.00   0.50    0.50    --   94.60  61.00 -30.00   54
 42  \w     73.00 158.00   0.50    0.50    --   94.60  61.00  90.00  170
 43  \w    101.00 183.00   0.50    0.50    --   94.60  65.00   5.93  164
 44  \w     71.00 178.00   0.50    0.50    --   94.60  61.00-150.00  214
 45  \w     67.00  93.00   0.50    0.50    --   94.60  73.00-115.77   52
 46  \w     71.00 112.00   0.50    0.50    --   94.60  61.00-120.00   82
 47  \w     72.00 107.00   0.50    0.50    --   94.60  61.00 -90.00   70
 48  \w     48.00 106.00   0.50    0.50    --   94.60 -61.00-180.00  116
 49  \w     71.00 103.00   0.50    0.50    --   94.60  61.00 -60.00   64
 50  \w     76.00 103.00   0.50    0.50    --   94.60  45.00-150.00   54
 51  \w     70.00  96.00   0.50    0.50    --   94.60  65.00   5.93   52
 52  \w    125.00 164.00   0.50    0.50    --   94.60  67.00-137.28   78
 53  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  94.40   52
 54  \w    107.00 132.00   0.50    0.50    --   94.60  64.00-111.77   50
 55  \w     71.00 104.00   0.50    0.50    --   94.60  61.00 120.00   66
 56  \w     43.00 109.00   0.50    0.50    --   94.60 -82.00 120.00  132
 57  \w     71.00  96.00   0.50    0.50    --   94.60  64.00-111.77   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB 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      -0.0738004000
_diffrn_orient_matrix_UB_12      -0.0237117000
_diffrn_orient_matrix_UB_13      0.1080326000
_diffrn_orient_matrix_UB_21      -0.2131210000
_diffrn_orient_matrix_UB_22      0.0400559000
_diffrn_orient_matrix_UB_23      -0.0167893000
_diffrn_orient_matrix_UB_31      -0.0270590000
_diffrn_orient_matrix_UB_32      -0.1520073000
_diffrn_orient_matrix_UB_33      0.0114179000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19048
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.981
_diffrn_reflns_theta_min         3.153
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0717P)^2^+0.8539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             3913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01813a2.cif
_cod_data_source_block           20190505_ea
_cod_depositor_comments          'Adding full bibliography for 7126374.cif.'
_cod_database_code               7126374
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.796
_reflns_odcompleteness_completeness 99.60
_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 Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C20(H20a,H20b), C23(H23a,H23b), C27(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), N16(H16), C2(H2), C17(H17), C25(H25), C19(H19), C21(H21), C26(H26)
2.d Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C29(H29a,H29b,H29c)
;
_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 2.907
_oxdiff_exptl_absorpt_empirical_full_min 0.421