Metal-free photocatalytic oxidative coupling of cyclic ethers and alcohols.
Li, Juncheng; Adelakun, Ibrahim O.; Wei, Zheng; Wang, Ting; Chemical communications (Cambridge, England) 61 (2025) 11818–11821; doi:10.1039/d5cc02030a

data_7134773
_publ_section_title
;
 Metal-free photocatalytic oxidative coupling of cyclic ethers and
 alcohols.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11818
_journal_page_last               11821
_journal_paper_doi               10.1039/d5cc02030a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H23 N O'
_chemical_formula_sum            'C23 H23 N O'
_chemical_formula_weight         329.42
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-04-02 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.594(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6833(10)
_cell_length_b                   7.9494(9)
_cell_length_c                   25.996(3)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      3.01
_cell_volume                     1769.3(4)
_computing_cell_refinement       'SAINT V8.38A (bruker, 2016)'
_computing_data_collection       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (bruker, 2016)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            68955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.170
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.6844
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used 
for absorption correction. wR2(int) was 0.0685 before 
and 0.0616 after correction. The Ratio of minimum to maximum 
transmission is 0.9411. The \l/2 correction factor is not present.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         6731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0637P)^2^+0.8647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5052
_reflns_number_total             6731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02030a2.cif
_cod_data_source_block           A-II
_cod_depositor_comments          'Adding full bibliography for 7134773.cif.'
_cod_database_code               7134773
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00J(H00J), C00L(H00M), C00N(H00Q), C00O(H00R)
2.c Idealised Me refined as rotating group:
 C00H(H00B,H00C,H00D), C00K(H00H,H00K,H00L), C00M(H00N,H00O,H00P), C00P(H00S,
 H00T,H00U)
;
_shelx_res_checksum              22167
_shelx_hkl_checksum              30216
_olex2_submission_special_instructions 'No special instructions were received'