Cascade reaction of o-enoyl arylisocyanide and o-hydroxy aromatic aldimine: a diastereoselective access to polycyclic spirobenzoxazine chromeno[4,3-b]pyrrole derivative
Li, Jian; Xiao, Yao; Peng, Xin; Shen, Jie; Cui, Lei; Lu, Shanya; Jia, Xueshun; Li, Chunju; Chemical Communications  (2022) –; doi:10.1039/D2CC02454C

data_7130603
_publ_section_title
;
 Cascade reaction of o-enoyl arylisocyanide and o-hydroxy aromatic
 aldimine: a diastereoselective access to polycyclic spirobenzoxazine
 chromeno[4,3-b]pyrrole derivative
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02454C
_journal_year                    2022
_chemical_formula_moiety         'C27 H24 N2 O4'
_chemical_formula_sum            'C27 H24 N2 O4'
_chemical_formula_weight         440.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-10 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.0632(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.35547(13)
_cell_length_b                   16.38420(16)
_cell_length_c                   12.90723(15)
_cell_measurement_reflns_used    21670
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3690
_cell_measurement_theta_min      4.3990
_cell_volume                     2209.46(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.970
_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     36.00 119.00   0.50    0.05    --   47.98  77.00 -30.00  166
  2  \w     91.00 117.00   0.50    0.20    --  104.70  61.00  60.00   52
  3  \w    136.00 176.00   0.50    0.20    --  104.70  61.00  60.00   80
  4  \w    133.00 176.00   0.50    0.20    --  104.70  77.00 120.00   86
  5  \w     87.00 115.00   0.50    0.20    --  104.70  77.00 120.00   56
  6  \w     35.00 120.00   0.50    0.05    --   47.98  57.00  90.00  170
  7  \w    100.00 134.00   0.50    0.20    --  104.70  61.00-120.00   68
  8  \w     98.00 178.00   0.50    0.20    --  104.70  15.00 -30.00  160
  9  \w     42.00 100.00   0.50    0.20    --  104.70 -95.00-120.00  116
 10  \w     91.00 128.00   0.50    0.20    --  104.70-148.00 -91.00   74
 11  \w     69.00  94.00   0.50    0.05    --   47.98-148.00 -91.00   50
 12  \w     41.00 105.00   0.50    0.20    --  104.70 -95.00-180.00  128
 13  \w     67.00 100.00   0.50    0.20    --  104.70 -95.00 -90.00   66
 14  \w     37.00 104.00   0.50    0.20    --  104.70 -95.00 -60.00  134
 15  \w     17.00  71.00   0.50    0.05    --   47.98-124.00  73.00  108
 16  \w     59.00  84.00   0.50    0.20    --  104.70-124.00  73.00   50
 17  \w     38.00 101.00   0.50    0.20    --  104.70-125.00 120.00  126
 18  \w     35.00  69.00   0.50    0.20    --  104.70 -77.00 120.00   68
 19  \w     35.00  60.00   0.50    0.20    --  104.70 -61.00  90.00   50
 20  \w     39.00  64.00   0.50    0.20    --  104.70 -61.00  30.00   50
 21  \w    -23.00   9.00   0.50    0.05    --   47.98 -38.00  30.00   64
 22  \w     17.00  45.00   0.50    0.05    --   47.98 -38.00  30.00   56
 23  \w     91.00 119.00   0.50    0.05    --   47.98 148.00 -43.00   56
 24  \w     78.00 127.00   0.50    0.20    --  104.70 148.00 -43.00   98
 25  \w    127.00 152.00   0.50    0.20    --  104.70 124.00 152.00   50
 26  \w    -94.00 -22.00   0.50    0.05    --  -47.98 124.00 152.00  144
 27  \w    -93.00 -68.00   0.50    0.20    --  -99.00 124.00 152.00   50
 28  \w   -126.00 -27.00   0.50    0.20    --  -99.00 148.00 -43.00  198
 29  \w   -125.00 -56.00   0.50    0.20    --  -99.00 143.00  88.13  138
 30  \w    -53.00 -28.00   0.50    0.20    --  -99.00 109.00  72.07   50
 31  \w   -108.00 -64.00   0.50    0.20    --  -99.00 109.00  72.07   88
 32  \w    -91.00 -66.00   0.50    0.05    --  -47.98 148.00 -43.00   50
 33  \w   -100.00 -71.00   0.50    0.20    --  -99.00  77.00-180.00   58
 34  \w    -64.00 -27.00   0.50    0.20    --  -99.00  61.00-180.00   74
 35  \w    -69.00 -29.00   0.50    0.20    --  -99.00  61.00 -90.00   80
 36  \w    -63.00 -29.00   0.50    0.20    --  -99.00  61.00   0.00   68
 37  \w    -54.00 -28.00   0.50    0.20    --  -99.00  61.00  60.00   52
 38  \w   -136.00 -88.00   0.50    0.20    --  -99.00 -30.00 -90.00   96
 39  \w   -171.00-146.00   0.50    0.20    --  -99.00 -30.00 -90.00   50
 40  \w   -168.00 -96.00   0.50    0.20    --  -99.00 -61.00  90.00  144
 41  \w   -113.00 -75.00   0.50    0.05    --  -47.98-125.00  90.00   76
 42  \w   -143.00 -82.00   0.50    0.20    --  -99.00-124.00  73.00  122
 43  \w    -84.00 -58.00   0.50    0.05    --  -47.98-148.00 -91.00   52
 44  \w   -137.00-112.00   0.50    0.20    --  -99.00-148.00 -91.00   50
 45  \w   -155.00-129.00   0.50    0.20    --  -99.00 -95.00-180.00   52
 46  \w   -128.00-101.00   0.50    0.20    --  -99.00 -95.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0793883000
_diffrn_orient_matrix_UB_12      -0.0362432000
_diffrn_orient_matrix_UB_13      0.0621082000
_diffrn_orient_matrix_UB_21      -0.0440471000
_diffrn_orient_matrix_UB_22      0.0863795000
_diffrn_orient_matrix_UB_23      0.0157053000
_diffrn_orient_matrix_UB_31      -0.1161930000
_diffrn_orient_matrix_UB_32      -0.0079642000
_diffrn_orient_matrix_UB_33      -0.1127838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.694
_diffrn_reflns_theta_min         4.407
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.7710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4129
_reflns_number_total             4518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02454c2.cif
_cod_data_source_block           exp_1800_auto
_cod_database_code               7130603
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C O N'
_chemical_oxdiff_usercomment     2207244299
_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:
 C9(H9), C12(H12), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C28(H28), C15(H15), C21(H21), C27(H27), C6(H6), C4(H4), C16(H16),
 C17(H17), C5(H5), C18(H18), C24(H24), C26(H26), C25(H25)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              92359
_shelx_hkl_checksum              45031
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.788