Dioxane promoted photochemical <i>O</i>-alkylation of 1,3-dicarbonyl compounds beyond carbene insertion into C-H and C-C bonds.
Zhou, Xinlong; Jiang, Jingjing; Zhang, Min; Wu, Qingqing; Zhu, Keyong; Shi, Dongjie; Hou, Sensen; Zhao, Jingjing; Li, Pan; Chemical communications (Cambridge, England) 60 (2024) 4330–4333; doi:10.1039/d4cc00778f

data_7132877
_publ_section_title
;
 Dioxane promoted photochemical <i>O</i>-alkylation of 1,3-dicarbonyl
 compounds beyond carbene insertion into C-H and C-C bonds.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4330
_journal_page_last               4333
_journal_paper_doi               10.1039/d4cc00778f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C25 H22 O4'
_chemical_formula_sum            'C25 H22 O4'
_chemical_formula_weight         386.42
_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     dual
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-11 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.406(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2833(18)
_cell_length_b                   10.038(2)
_cell_length_c                   20.688(4)
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.774
_cell_measurement_theta_min      2.260
_cell_volume                     2112.6(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20567
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.990
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1095 before and 0.0869 after correction. The Ratio of minimum to maximum transmission is 0.8005. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0623P)^2^+0.7084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2702
_reflns_number_total             4160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00778f2.cif
_cod_data_source_block           m12242_0m
_cod_depositor_comments
'Adding full bibliography for 7132875--7132877.cif.'
_cod_original_cell_volume        2112.7(7)
_cod_database_code               7132877
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.982
_diffrn_source_source            'Incoatc Ius 3.0 '
_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. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              96359
_shelx_hkl_checksum              83955
_olex2_submission_special_instructions 'No special instructions were received'