Rapid access to molecular complexity from bioderived 5-HMF derivatives via cascade cycloadditions
Averochkin, Gleb M.; Gordeev, Evgeniy G.; Kucherov, Fedor A.; Ananikov, Valentine P.; Green Chemistry 25 (2023) 1045–1055; doi:10.1039/D2GC04197A

data_7246145
_publ_section_title
;
 Rapid access to molecular complexity from bioderived 5-HMF derivatives
 via cascade cycloadditions
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1045
_journal_page_last               1055
_journal_paper_doi               10.1039/D2GC04197A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C37 H30 O10'
_chemical_formula_sum            'C37 H30 O10'
_chemical_formula_weight         634.61
_chemical_name_systematic
'(5-Benzoyl-4-(methoxycarbonyl)-3a1,6a-dihydro-1H,3H,6H,7H-3a,6:7,9adiepoxybenzo[ de]isochromene-6,7-diyl)bis(methylene) dibenzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-04-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                62.271(2)
_cell_angle_beta                 70.487(2)
_cell_angle_gamma                70.729(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3610(2)
_cell_length_b                   13.3550(3)
_cell_length_c                   13.4649(3)
_cell_measurement_reflns_used    14975
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8870
_cell_measurement_theta_min      3.7970
_cell_volume                     1520.04(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.944
_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   -120.00 -47.00   0.50    0.50    --  -48.76-165.00  11.00  146
  2  \w    -97.00 -72.00   0.50    0.50    --  -48.76 165.00  34.00   50
  3  \w    -61.00 -35.00   0.50    0.50    --  -48.76 116.00-113.00   52
  4  \w     71.00  96.00   0.50    0.50    --   48.76 165.00  34.00   50
  5  \w     59.00  88.00   0.50    0.50    --   48.76-116.00 158.00   58
  6  \w     64.00  89.00   0.50    0.50    --   48.76-165.00  11.00   50
  7  \w   -144.00-119.00   0.50    1.50    --  -90.00-116.00 158.00   50
  8  \w   -117.00 -92.00   0.50    1.50    --  -90.00-165.00  11.00   50
  9  \w    114.00 139.00   0.50    1.50    --  111.50-165.00  11.00   50
 10  \w    115.00 140.00   0.50    1.50    --  111.50 116.00-113.00   50
 11  \w     72.00 109.00   0.50    1.50    --  111.50-116.00 158.00   74
 12  \w     44.00  69.00   0.50    1.50    --  111.50-116.00 158.00   50
 13  \w    -18.00  24.00   0.50    0.50    --  -48.76  19.00   0.00   84
 14  \w   -117.00 -76.00   0.50    0.50    --  -48.76-125.00-150.00   82
 15  \w   -120.00 -76.00   0.50    0.50    --  -48.76-125.00 -90.00   88
 16  \w    -26.00  25.00   0.50    0.50    --  -48.76  19.00 -90.00  102
 17  \w    -24.00  12.00   0.50    0.50    --  -48.76  19.00 -30.00   72
 18  \w    -51.00 -25.00   0.50    1.50    --  -90.00  45.00 120.00   52
 19  \w    -47.00 -22.00   0.50    1.50    --  -90.00  45.00 150.00   50
 20  \w    141.00 167.00   0.50    1.50    --  111.50  45.00  30.00   52
 21  \w     79.00 105.00   0.50    1.50    --  111.50 -95.00 166.27   52
 22  \w    106.00 132.00   0.50    1.50    --  111.50  45.00  30.00   52
 23  \w     42.00  70.00   0.50    1.50    --  111.50 -61.00  60.00   56
 24  \w    102.00 178.00   0.50    1.50    --  111.50  45.00  90.00  152
 25  \w     41.00 107.00   0.50    1.50    --  111.50-102.00  -0.85  132
 26  \w     62.00 107.00   0.50    1.50    --  111.50-125.00-120.00   90
 27  \w     46.00  72.00   0.50    1.50    --  111.50 -87.00-167.66   52
 28  \w     74.00 104.00   0.50    1.50    --  111.50 -95.00 -30.00   60
 29  \w     48.00  77.00   0.50    1.50    --  111.50 -68.00 148.46   58
 30  \w     77.00 103.00   0.50    1.50    --  111.50 -95.00 150.00   52
 31  \w     40.00  71.00   0.50    1.50    --  111.50 -61.00-120.00   62
 32  \w     43.00  68.00   0.50    1.50    --  111.50 -77.00-120.00   50
 33  \w     42.00  72.00   0.50    1.50    --  111.50 -77.00  90.00   60
 34  \w     95.00 121.00   0.50    1.50    --  111.50 -87.00-167.66   52
 35  \w     84.00 109.00   0.50    1.50    --  111.50-125.00   0.00   50
 36  \w     94.00 137.00   0.50    1.50    --  111.50  70.00 -89.41   86
 37  \w    152.00 178.00   0.50    1.50    --  111.50  70.00 -89.41   52
 38  \w    102.00 154.00   0.50    1.50    --  111.50  30.00  90.00  104
 39  \w     58.00 107.00   0.50    1.50    --  111.50-110.00-107.52   98
 40  \w     48.00  74.00   0.50    1.50    --  111.50-125.00 -60.00   52
 41  \w     48.00  74.00   0.50    1.50    --  111.50 -81.00   2.67   52
 42  \w     90.00 135.00   0.50    1.50    --  111.50 -81.00   2.67   90
 43  \w    102.00 171.00   0.50    1.50    --  111.50  15.00   0.00  138
 44  \w     40.00  69.00   0.50    1.50    --  111.50 -95.00 -30.00   58
 45  \w     41.00  70.00   0.50    1.50    --  111.50 -61.00  90.00   58
 46  \w    141.00 167.00   0.50    1.50    --  111.50  77.00-150.00   52
 47  \w     91.00 117.00   0.50    1.50    --  111.50  77.00-150.00   52
 48  \w     73.00 108.00   0.50    1.50    --  111.50-109.00 -91.54   70
 49  \w     69.00 111.00   0.50    1.50    --  111.50-125.00  90.00   84
 50  \w     94.00 139.00   0.50    1.50    --  111.50  70.00-179.51   90
 51  \w    153.00 178.00   0.50    1.50    --  111.50  70.00-179.51   50
 52  \w     87.00 113.00   0.50    1.50    --  111.50 -85.00 137.79   52
 53  \w    145.00 171.00   0.50    1.50    --  111.50  91.00 -71.76   52
 54  \w     51.00  91.00   0.50    1.50    --  111.50 -77.00 -90.00   80
 55  \w     46.00  71.00   0.50    1.50    --  111.50 -61.00   0.00   50
 56  \w     69.00 105.00   0.50    1.50    --  111.50 -95.00-120.00   72
 57  \w     72.00  97.00   0.50    1.50    --  111.50 -95.00  30.00   50
 58  \w     46.00  71.00   0.50    1.50    --  111.50-125.00   0.00   50
 59  \w     42.00  67.00   0.50    1.50    --  111.50 -61.00 -30.00   50
 60  \w    133.00 178.00   0.50    1.50    --  111.50  45.00 120.00   90
 61  \w    114.00 147.00   0.50    1.50    --  111.50  61.00 -30.00   66
 62  \w    102.00 176.00   0.50    1.50    --  111.50  77.00 150.00  148
 63  \w     90.00 116.00   0.50    1.50    --  111.50 -85.00 -91.93   52
 64  \w     88.00 113.00   0.50    1.50    --  111.50 165.00  34.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0219006000
_diffrn_orient_matrix_UB_12      0.0714388000
_diffrn_orient_matrix_UB_13      -0.1307350000
_diffrn_orient_matrix_UB_21      -0.1022237000
_diffrn_orient_matrix_UB_22      0.1056803000
_diffrn_orient_matrix_UB_23      0.0206763000
_diffrn_orient_matrix_UB_31      0.1228770000
_diffrn_orient_matrix_UB_32      0.0385924000
_diffrn_orient_matrix_UB_33      0.0029212000
_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  0.0533
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21798
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.670
_diffrn_reflns_theta_min         3.798
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0564
_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^)+(0.1120P)^2^+0.6411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5872
_reflns_number_total             6239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04197a2.cif
_cod_data_source_block           gf632
_cod_depositor_comments
'Adding full bibliography for 7246144--7246147.cif.'
_cod_original_cell_volume        1520.04(7)
_cod_database_code               7246145
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     GF632
_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:
 C6(H6), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C16(H16), C17(H17), C19(H19), C18(H18), C20(H20), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_shelx_res_checksum              68861
_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 4.400
_oxdiff_exptl_absorpt_empirical_full_min 0.525