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_7160741
_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         'C49 H44 O4'
_chemical_formula_sum            'C49 H44 O4'
_chemical_formula_weight         696.84
_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             2025-07-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-10 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                72.2690(10)
_cell_angle_beta                 75.1630(10)
_cell_angle_gamma                73.7080(10)
_cell_formula_units_Z            2
_cell_length_a                   11.4926(3)
_cell_length_b                   12.0281(3)
_cell_length_c                   16.1002(5)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.341
_cell_measurement_theta_min      2.933
_cell_volume                     1999.00(10)
_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 0.988
_diffrn_measured_fraction_theta_max 0.976
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27268
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.731
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0841 after correction.
The Ratio of minimum to maximum transmission is 0.5843.
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    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.5116
_exptl_crystal_size_mid          0.3753
_exptl_crystal_size_min          0.1391
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         7770
_refine_ls_number_restraints     398
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0789
_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^)+(0.1529P)^2^+0.2392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2283
_refine_ls_wR_factor_ref         0.2618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5535
_reflns_number_total             7770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01117e2.cif
_cod_data_source_block           20250709e
_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_database_code               7160741
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.761
_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
 C39A, C35A, C36A, C38A, C34A, C37A, C40A, C6
 with sigma of 0.01
 C36, C34, C39, C37, C35, C38, C40, C6
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C6 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim
C34A \\sim C35A \\sim C36A \\sim C37A \\sim C38A \\sim C39A \\sim C40A: 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
C13 \\sim O3 \\sim O4 \\sim C14 \\sim C15 \\sim O3A \\sim O4A \\sim C14A \\sim
C15A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
4. Same fragment restrains
{O2, C11A, C12A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{O2, C11, C12}
{C6, C34A, C35A, C36A, C37A, C38A, C39A, C40A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C6, C34, C35, C36, C37, C38, C39, C40}
{C13, O3A, O4A, C14A, C15A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C13, O3, O4, C14, C15}
5. Others
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(O3A)=Sof(O4A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=1-FVAR(2)
 Sof(O3)=Sof(O4)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=FVAR(2)
 Sof(C34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(C37A)=Sof(H37A)=Sof(C38A)=
 Sof(H38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(3)
 Sof(C34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=
 Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C27(H27)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C14(H14A,H14B), C22(H22A,H22B), C14A(H14C,H14D),
 C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C35(H35), C37(H37), C38(H38), C39(H39), 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), C44(H44), C46(H46), C47(H47), C48(H48), C35A(H35A),
 C37A(H37A), C38A(H38A), C39A(H39A)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C40(H40A,H40B,H40C), C15(H15A,H15B,H15C), C49(H49A,H49B,
 H49C), C15A(H15D,H15E,H15F), C12A(H12D,H12E,H12F), C40A(H40D,H40E,H40F)
;
_shelx_res_checksum              49936
_olex2_submission_special_instructions 'No special instructions were received'