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_7064223
_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_absolute_configuration unk
_chemical_formula_moiety         'C21 H19 Cl O3'
_chemical_formula_sum            'C21 H19 Cl O3'
_chemical_formula_weight         354.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2026-01-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2026-01-14 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.699(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2354(5)
_cell_length_b                   5.1466(2)
_cell_length_c                   30.3740(12)
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    100.08(14)
_cell_measurement_theta_max      72.3190
_cell_measurement_theta_min      4.0620
_cell_volume                     1740.52(12)
_computing_cell_refinement       'CrysAlisPro 1.171.44.129a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.129a 64-bit (release 14-11-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.129a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.08(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     61.00 103.00   0.50    0.08    --   61.92  15.00-120.00   84
  2  \w     57.00  99.00   0.50    0.08    --   61.92  15.00 -30.00   84
  3  \w     59.00  97.00   0.50    0.08    --   61.92  15.00   0.00   76
  4  \w     54.00  89.00   0.50    0.08    --   61.92  15.00 -60.00   70
  5  \w     62.00  87.00   0.50    0.08    --   61.92  15.00  30.00   50
  6  \w     75.00 100.00   0.50    0.08    --   71.24  15.00   0.00   50
  7  \w     60.00  96.00   0.50    0.08    --   61.92  15.00  60.00   72
  8  \w     75.00 103.00   0.50    0.08    --   74.15  15.00 120.00   56
  9  \w     58.00  86.00   0.50    0.08    --   61.92  15.00 150.00   56
 10  \w     72.00 110.00   0.50    0.08    --   74.15  15.00 150.00   76
 11  \w     59.00  85.00   0.50    0.08    --   61.92  15.00 120.00   52
 12  \w     60.00  96.00   0.50    0.08    --   61.92  15.00  90.00   72
 13  \w     85.00 111.00   0.50    0.08    --   74.15  15.00 -60.00   52
 14  \w     77.00 115.00   0.50    0.08    --   74.15  15.00 -90.00   76
 15  \w     63.00 109.00   0.50    0.08    --   71.24  15.00-120.00   92
 16  \w     80.00 114.00   0.50    0.08    --   74.15  15.00-180.00   68
 17  \w     73.00 107.00   0.50    0.08    --   74.15  15.00  30.00   68
 18  \w     35.00  82.00   0.50    0.08    --   74.15-125.00  90.00   94
 19  \w     24.00  75.00   0.50    0.08    --   61.92-125.00 150.00  102
 20  \w     49.00  80.00   0.50    0.08    --   61.92-125.00   0.00   62
 21  \w     46.00  78.00   0.50    0.08    --   61.92-125.00  60.00   64
 22  \w     39.00  71.00   0.50    0.08    --   61.92-125.00 -60.00   64
 23  \w     44.00  77.00   0.50    0.08    --   61.92-125.00-120.00   66
 24  \w     23.00  80.00   0.50    0.08    --   61.92-125.00-150.00  114
 25  \w     28.00  53.00   0.50    0.08    --   61.92-125.00-180.00   50
 26  \w     33.00  58.00   0.50    0.08    --   71.24-125.00-120.00   50
 27  \w     64.00  89.00   0.50    0.08    --   71.24-125.00-120.00   50
 28  \w     53.00  87.00   0.50    0.08    --   71.24-125.00   0.00   68
 29  \w     36.00  92.00   0.50    0.08    --   74.15-125.00  60.00  112
 30  \w     36.00  65.00   0.50    0.08    --   61.92-125.00  90.00   58
 31  \w     48.00  89.00   0.50    0.08    --   71.24-125.00 120.00   82
 32  \w     58.00  92.00   0.50    0.08    --   74.15-125.00 150.00   68
 33  \w     37.00  92.00   0.50    0.08    --   74.15-125.00 -30.00  110
 34  \w     46.00  92.00   0.50    0.08    --   74.15-125.00 -60.00   92
 35  \w     50.00  92.00   0.50    0.08    --   74.15-125.00 -90.00   84
 36  \w     59.00  85.00   0.50    0.08    --   74.15-125.00-150.00   52
 37  \w     39.00  81.00   0.50    0.08    --   74.15-125.00-180.00   84
 38  \w     46.00  72.00   0.50    0.08    --   74.15-125.00  30.00   52
 39  \w     66.00  91.00   0.50    0.08    --   74.15-125.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1341983500
_diffrn_orient_matrix_UB_12      0.0732205500
_diffrn_orient_matrix_UB_13      0.0068050500
_diffrn_orient_matrix_UB_21      0.0021584000
_diffrn_orient_matrix_UB_22      -0.0147465000
_diffrn_orient_matrix_UB_23      -0.0505337000
_diffrn_orient_matrix_UB_31      -0.0338886000
_diffrn_orient_matrix_UB_32      0.2897968000
_diffrn_orient_matrix_UB_33      -0.0042994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            8907
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.045
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.129a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(3)
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.658
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     247
_refine_ls_restrained_S_all      1.588
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.1242
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3376
_refine_ls_wR_factor_ref         0.3428
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.641
_reflns_Friedel_fraction_max     0.641
_reflns_number_gt                2398
_reflns_number_total             2560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04524j2.cif
_cod_data_source_block           zy_168
_cod_depositor_comments
'Adding full bibliography for 7064222--7064224.cif.'
_cod_database_code               7064223
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S P Cl'
_diffrn_oxdiff_digest_od_ed
;

;
_diffrn_oxdiff_measurement_exp_name ZY_168.par
_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, All O(H) groups
2. Rigid body (RIGU) restrains
 Cl1, O1, O2, O3, C1, C2, H2, C3, C4, H4, C5, H5, C6, C10, C11, C12, H12, C13,
 H13, C14, H14A, H14B, H14C, C15, H15A, H15B, C16, C17, C18, H18A, H18B, C19,
 H19, C20, C21, C22, C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
3. Others
 Sof(H22A)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=
 Sof(H28)=1-FVAR(1)
 Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)=Sof(C24)=Sof(H24)=Sof(C23)=
 Sof(H23)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C22(H22), C22(H22A), C21(H21),
 C20(H20), C24(H24), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28)
4.d Fitted hexagon refined as free rotating group:
 C22(C21,C20,C16,C24,C23)
4.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.858
_oxdiff_exptl_absorpt_empirical_full_min 0.553