Formation of complex cyclic compounds <i>via</i> a dehydrogenative Diels-Alder reaction.
Xu, Zhongwei; Lei, Yu; Chang, Meng; Qiang, Ruihua; Hu, Qiong; Hu, Yimin; Organic & biomolecular chemistry 23 (2025) 9330–9335; doi:10.1039/d5ob01117e

data_7160739
_publ_section_title
;
 Formation of complex cyclic compounds <i>via</i> a dehydrogenative
 Diels-Alder reaction.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9330
_journal_page_last               9335
_journal_paper_doi               10.1039/d5ob01117e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C51 H48 O4'
_chemical_formula_sum            'C51 H48 O4'
_chemical_formula_weight         724.89
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-12-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-06-26 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                94.418(4)
_cell_angle_beta                 98.514(4)
_cell_angle_gamma                109.861(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5564(15)
_cell_length_b                   11.9079(18)
_cell_length_c                   20.159(3)
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.351
_cell_measurement_theta_min      2.666
_cell_volume                     2113.7(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Bruker PHOTON-II area detector'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CMOS-PHOTONII area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            72621
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_min         2.524
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.7276.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     698
_refine_ls_number_reflns         10284
_refine_ls_number_restraints     643
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0600
_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^)+(0.0728P)^2^+0.5206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6908
_reflns_number_total             10284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01117e2.cif
_cod_data_source_block           20241202a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160738--7160742.cif.
;
_cod_original_cell_volume        2113.7(5)
_cod_database_code               7160739
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.983
_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. Restrained planarity
 C48A, C46A, C45A, C49A, C47A, C44, C50A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim
C45A \\sim C46A \\sim C47A \\sim C48A \\sim C49A \\sim C50A \\sim C51A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O2 \\sim C11 \\sim C12 \\sim C11A \\sim C12A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C37 \\sim C40 \\sim C41 \\sim C40A \\sim C41A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C28A
\\sim C29A \\sim C30A \\sim C31A \\sim C32A \\sim C33A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C13 \\sim C14 \\sim C15 \\sim O3 \\sim O4 \\sim C14A \\sim C15A \\sim O3A \\sim
O4A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{C13, C14A, C15A, O3A, O4A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C13, C14, C15, O3, O4}
{C27, C28A, C29A, C30A, C31A, C32A, C33A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C27, C28, C29, C30, C31, C32, C33}
{C37, C40A, C41A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C37, C40, C41}
{C44, C45A, C46A, C47A, C48A, C49A, C50A, C51A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C44, C45, C46, C47, C48, C49, C50, C51}
{O2, C11A, C12A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{O2, C11, C12}
5. Others
 Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=Sof(C47A)=Sof(C48A)=Sof(H48A)=
 Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51D)=
 Sof(H51E)=Sof(H51F)=1-FVAR(1)
 Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(C48)=Sof(H48)=Sof(C49)=
 Sof(H49)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=
 FVAR(1)
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 Sof(O3A)=Sof(O4A)=1-FVAR(2)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(O3)=
 Sof(O4)=FVAR(2)
 Sof(C40A)=Sof(H40C)=Sof(H40D)=Sof(C41A)=Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(3)
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=FVAR(3)
 Sof(H27A)=Sof(C28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=
 Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=1-FVAR(4)
 Sof(H27)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=FVAR(4)
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(5)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(5)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C27(H27), C27(H27A)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C22(H22A,H22B), C40(H40A,H40B), C50(H50A,H50B),
 C11(H11A,H11B), C11A(H11C,H11D), C14A(H14C,H14D), C40A(H40C,H40D), C50A(H50C,
 H50D)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
 C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
  C38(H38), C39(H39), C45(H45), C46(H46), C48(H48), C49(H49), C29A(H29A),
 C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A), C45A(H45A), C46A(H46A),
 C48A(H48A), C49A(H49A)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C41(H41A,H41B,H41C), C51(H51A,H51B,H51C), C12(H12A,H12B,
 H12C), C12A(H12D,H12E,H12F), C15A(H15D,H15E,H15F), C41A(H41D,H41E,H41F),
 C51A(H51D,H51E,H51F)
;
_shelx_res_checksum              73655
_olex2_submission_special_instructions 'No special instructions were received'