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_7123208
_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             2017-11-02
_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                101.137(5)
_cell_angle_beta                 109.082(6)
_cell_angle_gamma                107.852(5)
_cell_formula_units_Z            2
_cell_length_a                   10.3803(6)
_cell_length_b                   12.1686(7)
_cell_length_c                   13.3420(9)
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5240
_cell_measurement_theta_min      4.0280
_cell_volume                     1433.10(19)
_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 -108.00  -32.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 76

  2 omega -105.00   38.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -60.0000 143

  3 omega  -49.00   37.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  150.0000 86

  4 omega  -31.00   46.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 77

  5 omega   40.00   75.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 35

  6 omega   69.00  101.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 32

  7 omega    0.00   34.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  120.0000 34

  8 omega  -26.00   65.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 91

  9 omega   58.00  102.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 44

 10 omega   33.00   59.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -30.0000 26

 11 omega   79.00  105.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 26

 12 omega   44.00  104.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  120.0000 60

 13 omega   47.00   74.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 27

 14 omega   24.00   60.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 36

 15 omega   60.00  102.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 42

 16 omega   47.00   75.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 28

 17 omega    0.00   27.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -30.0000 27

 18 omega   39.00  109.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 19 omega   43.00  108.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 65

 20 omega   42.00  112.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 70

 21 omega   88.00  177.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 89

 22 omega  105.00  165.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 60

 23 omega  106.00  164.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 58

 24 omega   40.00   91.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 51

 25 omega   52.00   86.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 34

 26 omega   67.00  105.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 38

 27 omega   40.00   89.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 49

 28 omega   44.00   73.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 29

 29 omega   48.00   96.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 48

 30 omega   88.00  178.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 90

 31 omega   69.00  109.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 40

 32 omega   43.00   99.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 56

 33 omega   64.00  126.00   1.0000   18.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0750198000
_diffrn_orient_matrix_UB_12      0.0673987000
_diffrn_orient_matrix_UB_13      0.1274208000
_diffrn_orient_matrix_UB_21      0.1428977000
_diffrn_orient_matrix_UB_22      0.0720491000
_diffrn_orient_matrix_UB_23      -0.0104579000
_diffrn_orient_matrix_UB_31      -0.0572831000
_diffrn_orient_matrix_UB_32      0.1003191000
_diffrn_orient_matrix_UB_33      -0.0189755000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10676
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.708
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90012
_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    1.234
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0609P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3642
_reflns_number_total             5118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02170a2.cif
_cod_data_source_block           201711215
_cod_original_cell_volume        1433.09(16)
_cod_database_code               7123208
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N1O5
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.880
_reflns_odcompleteness_completeness 99.92
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C22(H22), C23(H23), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C34(H34A,H34B)
2.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)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'