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_7123206
_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         'C23 H18 O3'
_chemical_formula_sum            'C23 H18 O3'
_chemical_formula_weight         342.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-24
_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                90
_cell_angle_beta                 135.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.984(2)
_cell_length_b                   10.1319(6)
_cell_length_c                   20.901(4)
_cell_measurement_reflns_used    2062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2820
_cell_measurement_theta_min      4.3290
_cell_volume                     1770.5(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  -20.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -60.0000 59

  2 omega  -49.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 53

  3 omega   22.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 42

  4 omega   58.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 49

  5 omega   26.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 67

  6 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 26

  7 omega   25.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   90.0000 80

  8 omega   58.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 51

  9 omega   81.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 92

 10 omega   54.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 37

 11 omega  107.00  152.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 45

 12 omega   38.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 33

 13 omega   90.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 34

 14 omega   48.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 33

 15 omega  148.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 29

 16 omega  103.00  129.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 26

 17 omega   38.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 40

 18 omega   41.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 45

 19 omega   67.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -150.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0365119000
_diffrn_orient_matrix_UB_12      -0.1161994000
_diffrn_orient_matrix_UB_13      0.0602325000
_diffrn_orient_matrix_UB_21      0.1769468000
_diffrn_orient_matrix_UB_22      0.0422837000
_diffrn_orient_matrix_UB_23      0.0752865000
_diffrn_orient_matrix_UB_31      -0.0365087000
_diffrn_orient_matrix_UB_32      0.0884506000
_diffrn_orient_matrix_UB_33      0.0431229000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6537
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.039
_diffrn_reflns_theta_max         67.039
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0085(5)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0583P)^2^+0.1852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2328
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02170a2.cif
_cod_data_source_block           201810410
_cod_original_cell_volume        1770.4(8)
_cod_database_code               7123206
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.866
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
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), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'