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_7123209
_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         'C36 H34 O5'
_chemical_formula_sum            'C36 H34 O5'
_chemical_formula_weight         546.63
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6175(2)
_cell_length_b                   13.9358(3)
_cell_length_c                   20.2592(5)
_cell_measurement_reflns_used    3918
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7880
_cell_measurement_theta_min      3.8520
_cell_volume                     2973.46(11)
_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  -25.00    1.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 26

  2 omega  -99.00  -16.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 83

  3 omega    0.00   33.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 33

  4 omega  -28.00   11.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 39

  5 omega   34.00   76.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 42

  6 omega  -35.00   -9.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 26

  7 omega   83.00  109.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 26

  8 omega   39.00   74.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 35

  9 omega   43.00   69.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 26

 10 omega   16.00   46.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 30

 11 omega  -32.00   40.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 72

 12 omega   48.00   86.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 38

 13 omega   48.00   74.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 26

 14 omega  101.00  176.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 75

 15 omega   90.00  173.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 83

 16 omega   49.00   83.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 34

 17 omega   39.00  115.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 76

 18 omega   98.00  124.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 26

 19 omega   39.00  102.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 63

 20 omega   58.00   89.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 31

 21 omega   51.00   77.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 26

 22 omega   38.00   99.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 61

 23 omega  121.00  167.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0651290000
_diffrn_orient_matrix_UB_12      0.0623852000
_diffrn_orient_matrix_UB_13      -0.0571868000
_diffrn_orient_matrix_UB_21      0.0523133000
_diffrn_orient_matrix_UB_22      0.0911343000
_diffrn_orient_matrix_UB_23      0.0369122000
_diffrn_orient_matrix_UB_31      0.1199907000
_diffrn_orient_matrix_UB_32      -0.0058306000
_diffrn_orient_matrix_UB_33      -0.0352789000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.860
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95437
_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    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00163(18)
_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   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5317
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0684P)^2^+0.6536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4042
_reflns_number_total             5317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02170a2.cif
_cod_data_source_block           201805258
_cod_original_cell_volume        2973.48(12)
_cod_database_code               7123209
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 99.95
_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(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\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), C33(H33A,H33B), C35(H35A,H35B)
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), C27(H27), C28(H28), C29(H29),
  C30(H30), C26(H26)
3.d Fitted hexagon refined as free rotating group:
 C27(C28,C29,C30,C25,C26)
3.e Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_olex2_submission_special_instructions 'No special instructions were received'