Unexpected multi-component one-pot cascade to access furanobenzodihydropyran-fused polycyclic heterocycles
Guo, Jiao-Mei; Miao, Hongjie; Zhao, Yang; Bai, Xu-Guan; Zhu, Yan-Shuo; Wang, Qi-Lin; Bu, Zhanwei; Chemical Communications  (2019) –; doi:10.1039/C9CC02170A

data_7123207
_publ_section_title
;
 Unexpected multi-component one-pot cascade to access
 furanobenzodihydropyran-fused polycyclic heterocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02170A
_journal_year                    2019
_chemical_formula_moiety         'C35 H32 O4'
_chemical_formula_sum            'C35 H32 O4'
_chemical_formula_weight         516.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                68.945(4)
_cell_angle_beta                 86.325(4)
_cell_angle_gamma                89.998(4)
_cell_formula_units_Z            4
_cell_length_a                   13.0451(6)
_cell_length_b                   13.1383(6)
_cell_length_c                   17.7650(9)
_cell_measurement_reflns_used    5987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7040
_cell_measurement_theta_min      3.6200
_cell_volume                     2834.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -105.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000 -180.0000 106

  2 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 83

  3 omega   -6.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 26

  4 omega   78.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 31

  5 omega   28.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 47

  6 omega   -3.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 26

  7 omega   12.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -90.0000 34

  8 omega   42.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 25

  9 omega   36.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 38

 10 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -90.0000 25

 11 omega  -36.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  -30.0000 100

 12 omega   57.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

 13 omega   23.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 28

 14 omega   21.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 86

 15 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 26

 16 omega    9.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 26

 17 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 27

 18 omega   59.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 47

 19 omega   69.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 34

 20 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 26

 21 omega   37.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 25

 22 omega   57.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 58

 23 omega   42.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 48

 24 omega   44.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 26

 25 omega   56.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 35

 26 omega   39.00  134.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

 27 omega   46.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 67

 28 omega   38.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

 29 omega   37.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 54

 30 omega   42.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 62

 31 omega   39.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 59

 32 omega   38.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 38

 33 omega  123.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 26

 34 omega   78.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 26

 35 omega   58.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 35

 36 omega   40.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 26

 37 omega  145.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 25

 38 omega   63.00  138.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 75

 39 omega   57.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 34

 40 omega   79.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 70

 41 omega   36.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0605161000
_diffrn_orient_matrix_UB_12      0.0243792000
_diffrn_orient_matrix_UB_13      0.0687145000
_diffrn_orient_matrix_UB_21      -0.0812372000
_diffrn_orient_matrix_UB_22      -0.0878806000
_diffrn_orient_matrix_UB_23      0.0053646000
_diffrn_orient_matrix_UB_31      0.0612440000
_diffrn_orient_matrix_UB_32      -0.0864814000
_diffrn_orient_matrix_UB_33      0.0626503000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.396
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00188(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         10123
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0682P)^2^+0.2586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7559
_reflns_number_total             10123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02170a2.cif
_cod_data_source_block           201809378
_cod_database_code               7123207
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_chemical_oxdiff_usercomment     1
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.902
_reflns_odcompleteness_completeness 99.94
_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. Restrained distances
 C34-C35
 1.75 with sigma of 0.02
 C34'-C35'
 1.75 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C7'(H7'), C8'(H8'), C10'(H10'), C11'(H11')
3.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C34'(H34C,H34D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C1'(H1'), C2'(H2'), C3'(H3'),
 C4'(H4'), C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'),
 C19'(H19'), C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'),
 C27'(H27'), C28'(H28'), C29'(H29'), C30'(H30'), C31'(H31')
3.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C33'(H33D,H33E,H33F), C35'(H35D,
 H35E,H35F)
;
_olex2_submission_special_instructions 'No special instructions were received'