Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in the reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one with malononitrile
Liu, Jie-Jie; Cheng, Liang; Huang, Hong-Yan; Wei, Feng; Wang, Dong; Liu, Li; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00904F

data_7155658
_publ_section_title
;
 Unprecedented formation of 3-(tetrahydrofuran-2-yl)-4H-chromen-4-one in
 the reaction between 3,3a-dihydro-9H-furo[3,4-b]chromen-9-one with
 malononitrile
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00904F
_journal_year                    2017
_chemical_formula_moiety         'C21 H18 O7'
_chemical_formula_sum            'C21 H18 O7'
_chemical_formula_weight         382.35
_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     dual
_audit_creation_date             2016-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-05-23 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                103.557(8)
_cell_angle_beta                 95.557(9)
_cell_angle_gamma                108.701(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6133(15)
_cell_length_b                   10.8331(17)
_cell_length_c                   11.794(2)
_cell_measurement_reflns_used    2501
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4762
_cell_measurement_theta_min      1.8080
_cell_volume                     879.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 99.4000
_diffrn_measured_fraction_theta_max 27.4762
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9382
              2theta: -19.8823
scan:
    Number of images: 350
               Slice: -110.0000 - 65.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9382
              2theta: -19.8823
scan:
    Number of images: 281
               Slice: -75.5000 - 65.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 44.9382
              2theta: -19.8823
scan:
    Number of images: 286
               Slice: -80.0000 - 63.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9382
              2theta: -19.8823
;
_diffrn_measurement_device
;
?
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0545
_diffrn_orient_matrix_UB_12      -0.1092
_diffrn_orient_matrix_UB_13      0.0719
_diffrn_orient_matrix_UB_21      -0.0011
_diffrn_orient_matrix_UB_22      -0.0175
_diffrn_orient_matrix_UB_23      -0.1000
_diffrn_orient_matrix_UB_31      0.0808
_diffrn_orient_matrix_UB_32      -0.0233
_diffrn_orient_matrix_UB_33      0.0285
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12308
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.808
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0446P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3648
_reflns_number_total             4002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00904f2.cif
_cod_data_source_block           a
_cod_original_cell_volume        880.0(3)
_cod_database_code               7155658
_diffrn_number_total             4006
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              16529
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'