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_7123205
_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 O5'
_chemical_formula_sum            'C35 H32 O5'
_chemical_formula_weight         532.60
_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             2017-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                98.139(2)
_cell_angle_beta                 106.093(3)
_cell_angle_gamma                106.176(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5346(3)
_cell_length_b                   10.6065(3)
_cell_length_c                   15.8593(5)
_cell_measurement_reflns_used    3930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6430
_cell_measurement_theta_min      4.7430
_cell_volume                     1437.77(9)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00  -32.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 152

  2 omega -102.00  -15.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 174

  3 omega -108.00  -32.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 152

  4 omega -103.00   -5.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -90.0000 196

  5 omega   57.00  110.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 106

  6 omega  -36.00   74.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  -60.0000 220

  7 omega   57.00  110.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 106

  8 omega  -25.00   17.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 84

  9 omega   49.00   77.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 56

 10 omega   64.00   90.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000    0.0000 52

 11 omega  -27.00   14.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  120.0000 82

 12 omega   61.00  106.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 90

 13 omega   58.00  109.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 102

 14 omega   57.00   93.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 72

 15 omega   28.00   63.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  120.0000 70

 16 omega   70.00   96.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 52

 17 omega  103.00  166.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 126

 18 omega   67.00  174.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 214

 19 omega   63.00  112.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 98

 20 omega   38.00   90.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 104

 21 omega   51.00   85.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 68

 22 omega   42.00  108.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 132

 23 omega   47.00  104.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 114

 24 omega   43.00  127.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 168

 25 omega   42.00   72.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 60

 26 omega   91.00  169.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 156

 27 omega   77.00  124.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 94

 28 omega   81.00  109.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 56

 29 omega   51.00   87.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 72

 30 omega   62.00   89.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 54

 31 omega  135.00  176.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 82

 32 omega   95.00  123.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0661396000
_diffrn_orient_matrix_UB_12      0.1420596000
_diffrn_orient_matrix_UB_13      -0.0146725000
_diffrn_orient_matrix_UB_21      0.0357766000
_diffrn_orient_matrix_UB_22      0.0620127000
_diffrn_orient_matrix_UB_23      0.1006621000
_diffrn_orient_matrix_UB_31      0.1618037000
_diffrn_orient_matrix_UB_32      -0.0144173000
_diffrn_orient_matrix_UB_33      0.0219605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10297
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.468
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67785
_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    1.230
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5142
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0770P)^2^+0.1440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3985
_reflns_number_total             5142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02170a2.cif
_cod_data_source_block           201711217
_cod_original_cell_volume        1437.76(8)
_cod_database_code               7123205
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N1O5
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.909
_reflns_odcompleteness_completeness 99.98
_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. Uiso/Uaniso restraints and constraints
Uanis(C35) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(C34) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C22(H22), C23(H23), C31(H31)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30)
3.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'