Divergent synthesis of selenide-containing spirocarbocycles and phenanthrenes through Cu(OTf)2-promoted selenylation of alkyne-containing phenol-based biaryls
Guo, Le; Liu, Anjia; Qi, Hongbo; Gu, Lei; Yuan, Xingyu; Chi, Dongmei; Chen, Shufeng; New Journal of Chemistry 49 (2025) 5989–5994; doi:10.1039/D5NJ00253B

data_7063688
_publ_section_title
;
 Divergent synthesis of selenide-containing spirocarbocycles and
 phenanthrenes through Cu(OTf)2-promoted selenylation of alkyne-containing
 phenol-based biaryls
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5989
_journal_page_last               5994
_journal_paper_doi               10.1039/D5NJ00253B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C26 H18 O Se'
_chemical_formula_sum            'C26 H18 O Se'
_chemical_formula_weight         425.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-09-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.221(16)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.615(3)
_cell_length_b                   9.7502(10)
_cell_length_c                   35.915(6)
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    219.99(10)
_cell_measurement_theta_max      21.5900
_cell_measurement_theta_min      2.2240
_cell_volume                     8628(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -29.00  67.00   1.00    6.00    --  -11.43  19.00 -30.00   96
  2  \w    -42.00  66.00   1.00    6.00    --  -11.43  19.00-120.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0097600000
_diffrn_orient_matrix_UB_12      0.0503271000
_diffrn_orient_matrix_UB_13      0.0098821000
_diffrn_orient_matrix_UB_21      0.0162334000
_diffrn_orient_matrix_UB_22      -0.0287527000
_diffrn_orient_matrix_UB_23      0.0188566000
_diffrn_orient_matrix_UB_31      0.0216968000
_diffrn_orient_matrix_UB_32      0.0439793000
_diffrn_orient_matrix_UB_33      0.0010228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.1385
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19366
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.245
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0392P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3699
_reflns_number_total             7580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00253b2.cif
_cod_data_source_block           1196-2
_cod_depositor_comments
'Adding full bibliography for 7063687--7063688.cif.'
_cod_database_code               7063688
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C29(H29), C30(H30), C32(H32), C37(H37), C38(H38), C39(H39),
 C40(H40), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C49(H49),
  C50(H50), C51(H51), C52(H52)
2.b Tetrahedral OH refined with riding coordinates:
 O1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              47740
_shelx_hkl_checksum              6780
_shelx_fab_checksum              25776
_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 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.586