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_7063687
_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         'C27 H20 O Se'
_chemical_formula_sum            'C27 H20 O Se'
_chemical_formula_weight         439.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.016(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2238(3)
_cell_length_b                   10.1572(3)
_cell_length_c                   21.0271(8)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    249.99(10)
_cell_measurement_theta_max      73.7090
_cell_measurement_theta_min      2.1630
_cell_volume                     2118.55(13)
_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      249.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -58.00   9.00   1.00    1.00    --  -40.73  19.00  90.00   67
  2  \w     29.00  71.00   1.00    1.00    --   40.73 -99.00-150.00   42
  3  \w     23.00  95.00   1.00    1.00    --   40.73-125.00-180.00   72
  4  \w     52.00  99.00   1.00    1.00    --  106.95 -95.00  60.00   47
  5  \w     81.00 175.00   1.00    1.00    --  106.95  45.00 120.00   94
  6  \w    143.00 178.00   1.00    1.00    --  106.95 125.00 -30.00   35
  7  \w     88.00 175.00   1.00    1.00    --  106.95  77.00   0.00   87
  8  \w    -42.00  -8.00   1.00    1.00    --  -40.98 125.00-150.00   34
  9  \w      4.00  76.00   1.00    1.00    --   40.98 -99.00 -30.00   72
 10  \w    144.00 177.00   1.00    1.00    --  106.95  77.00 -90.00   33
 11  \w     80.00 106.00   1.00    1.00    --  106.95  77.00  60.00   26
 12  \w    121.00 178.00   1.00    1.00    --  106.95  77.00  60.00   57
 13  \w     92.00 117.00   1.00    1.00    --  106.95  45.00 -30.00   25
 14  \w    129.00 163.00   1.00    1.00    --  106.95  45.00 -30.00   34
 15  \w     99.00 125.00   1.00    1.00    --  106.95 -61.00 150.00   26
 16  \w     36.00  62.00   1.00    1.00    --  106.95 -61.00 150.00   26
;
_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      0.0512476000
_diffrn_orient_matrix_UB_12      -0.0079212000
_diffrn_orient_matrix_UB_13      0.0751394000
_diffrn_orient_matrix_UB_21      0.1158874000
_diffrn_orient_matrix_UB_22      0.0948610000
_diffrn_orient_matrix_UB_23      -0.0029428000
_diffrn_orient_matrix_UB_31      -0.0898300000
_diffrn_orient_matrix_UB_32      0.1180373000
_diffrn_orient_matrix_UB_33      0.0074056000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_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            9346
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.626
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78869
_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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.4791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3798
_reflns_number_total             4179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00253b2.cif
_cod_data_source_block           55
_cod_depositor_comments
'Adding full bibliography for 7063687--7063688.cif.'
_cod_original_cell_volume        2118.56(13)
_cod_database_code               7063687
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              93811
_shelx_hkl_checksum              90331
_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 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.864