Catalyst-controlled divergent synthesis of 2,8-dioxabicyclo[3.3.1]nonanes and benzo[c]chromen-6-ones
Zhang, Yichi; Wu, Qingling; Zhang, Qingxiao; Zhao, Yang; Wang, Qilin; New Journal of Chemistry 50 (2026) 3580–3584; doi:10.1039/D5NJ04524J

data_7064224
_publ_section_title
;
 Catalyst-controlled divergent synthesis of 2,8-dioxabicyclo[3.3.1]nonanes
 and benzo[c]chromen-6-ones
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3580
_journal_page_last               3584
_journal_paper_doi               10.1039/D5NJ04524J
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C21 H14 O4'
_chemical_formula_sum            'C21 H14 O4'
_chemical_formula_weight         330.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-14
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2025-11-14 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.165(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4615(3)
_cell_length_b                   7.4413(3)
_cell_length_c                   22.9597(7)
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1940
_cell_measurement_theta_min      4.8650
_cell_volume                     1603.87(10)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.980
_diffrn_measurement_details
;
  1 omega  -36.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  113.0000 -168.0000 32

  2 omega  -69.00  -42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  113.0000 -168.0000 27

  3 omega  -45.00    8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 53

  4 omega  -38.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 26

  5 omega   12.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 27

  6 omega   46.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 31

  7 omega   27.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 72

  8 omega   -1.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 36

  9 omega  -36.00   16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   90.0000 52

 10 omega   57.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 48

 11 omega   40.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 33

 12 omega   39.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 31

 13 omega   39.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 49

 14 omega   76.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 30

 15 omega   69.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 46

 16 omega   41.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 59

 17 omega   45.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 32

 18 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

 19 omega   48.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 26

 20 omega   91.00  162.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 71

 21 omega   50.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 33

 22 omega   93.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 64

 23 omega  119.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0047590000
_diffrn_orient_matrix_UB_12      -0.1180519000
_diffrn_orient_matrix_UB_13      -0.0548212000
_diffrn_orient_matrix_UB_21      -0.0112281000
_diffrn_orient_matrix_UB_22      -0.1698267000
_diffrn_orient_matrix_UB_23      0.0375348000
_diffrn_orient_matrix_UB_31      -0.1636768000
_diffrn_orient_matrix_UB_32      0.0081515000
_diffrn_orient_matrix_UB_33      -0.0126350000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6385
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.781
_diffrn_reflns_theta_min         3.881
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88561
_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    1.368
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0774P)^2^+0.1056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             3019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04524j2.cif
_cod_data_source_block           201905122
_cod_depositor_comments
'Adding full bibliography for 7064222--7064224.cif.'
_cod_database_code               7064224
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.879
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'