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_7246147
_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         'C39 H35 N O10'
_chemical_formula_sum            'C39 H35 N O10'
_chemical_formula_weight         677.68
_chemical_name_systematic
'Dimethyl 6,7-bis((benzoyloxy)methyl)-2-benzyl-2,3,3a1,6a-tetrahydro-1H,6H,7H- 3a,6:7,9a-diepoxybenzo[de]isoquinoline-4,5-dicarboxylate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_audit_update_record
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.19560(10)
_cell_length_b                   33.6799(5)
_cell_length_c                   10.50800(10)
_cell_measurement_reflns_used    17610
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3560
_cell_measurement_theta_min      2.6160
_cell_volume                     3224.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.978
_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 -38.00   0.40    1.50    --  -48.51 -44.00 -72.00  205
  2  \w    -50.00  22.00   0.40    1.50    --  -48.51  44.00  78.00  180
  3  \w     38.00 120.00   0.40    1.50    --   48.51  44.00  78.00  205
  4  \w    -23.00  49.00   0.40    1.50    --   48.51 -44.00 -72.00  180
  5  \w   -161.00 -79.00   0.40    1.50    --  -90.00 -44.00 -72.00  205
  6  \w    -50.00 -20.00   0.40    1.50    --  -90.00  44.00  78.00   75
  7  \w    101.00 177.00   0.40    1.50    --  111.50  44.00  78.00  190
  8  \w   -120.00 -74.00   0.40    1.50    --  -48.51-125.00  90.00  115
  9  \w    -25.00  25.00   0.40    1.50    --   48.51 -19.00-180.00  125
 10  \w    -71.00 -19.00   0.40    1.50    --  -90.00  61.00-120.00  130
 11  \w     40.00 104.00   0.40    1.50    --  111.50 -77.00-180.00  160
 12  \w     40.00  70.00   0.40    1.50    --  111.50 -61.00 -90.00   75
 13  \w     40.00  70.00   0.40    1.50    --  111.50 -61.00  90.00   75
 14  \w     40.00  70.00   0.40    1.50    --  111.50 -61.00 -60.00   75
 15  \w     40.00 104.00   0.40    1.50    --  111.50 -95.00-180.00  160
 16  \w     40.00  70.00   0.40    1.50    --  111.50 -61.00 -30.00   75
 17  \w     40.00  70.00   0.40    1.50    --  111.50 -61.00-150.00   75
 18  \w    101.00 177.00   0.40    1.50    --  111.50  30.00 120.00  190
 19  \w    101.00 177.00   0.40    1.50    --  111.50  45.00 120.00  190
 20  \w     40.00 104.00   0.40    1.50    --  111.50 -95.00  60.00  160
 21  \w    101.00 177.00   0.40    1.50    --  111.50  45.00 150.00  190
 22  \w    101.00 177.00   0.40    1.50    --  111.50  15.00-150.00  190
 23  \w     40.00 104.00   0.40    1.50    --  111.50 -95.00 -30.00  160
 24  \w     95.00 177.00   0.40    1.50    --  111.50 125.00   0.00  205
 25  \w     95.00 177.00   0.40    1.50    --  111.50 125.00 -30.00  205
 26  \w     40.00 104.00   0.40    1.50    --  111.50 -77.00   0.00  160
 27  \w     27.00  63.00   0.40    1.50    --   48.51  77.00 -30.00   90
;
_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      -0.0110601000
_diffrn_orient_matrix_UB_12      -0.0251610000
_diffrn_orient_matrix_UB_13      0.1208231000
_diffrn_orient_matrix_UB_21      0.1687513000
_diffrn_orient_matrix_UB_22      -0.0013131000
_diffrn_orient_matrix_UB_23      0.0287575000
_diffrn_orient_matrix_UB_31      -0.0013911000
_diffrn_orient_matrix_UB_32      0.0381860000
_diffrn_orient_matrix_UB_33      0.0803937000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.693
_diffrn_reflns_theta_min         2.624
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00065(11)
_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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0457P)^2^+6.5162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6100
_reflns_number_total             6867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04197a2.cif
_cod_data_source_block           ga-465
_cod_depositor_comments
'Adding full bibliography for 7246144--7246147.cif.'
_cod_database_code               7246147
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H35 N O10'
_chemical_oxdiff_usercomment     GA-465
_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:
 C3(H3), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C13(H13A,H13B), C20(H20A,H20B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              33817
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.766