Metal-free visible-light induced cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones and diselenides: access to 5-hydroxy-3-selenyl-4a,8a-dihydro-2H-chromen-6(5H)-ones
Ma, Xian-Li; Wang, Qian; Feng, Xi-Yuan; Mo, Zu-Yu; Pan, Ying-Ming; Chen, Yan-Yan; Xin, Mao; Xu, Yan-Li; Green Chemistry 21 (2019) 3547–; doi:10.1039/C9GC00570F

data_7232870
_publ_section_title
;
 Metal-free visible-light induced cyclization/substitution cascade
 reaction of alkyne-tethered cyclohexadienones and diselenides: access to
 5-hydroxy-3-selenyl-4a,8a-dihydro-2H-chromen-6(5H)-ones
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3547
_journal_paper_doi               10.1039/C9GC00570F
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C29 H23 F3 O2 Se2'
_chemical_formula_sum            'C29 H23 F3 O2 Se2'
_chemical_formula_weight         618.39
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-21 deposited with the CCDC.    2019-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.488(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2456(8)
_cell_length_b                   11.4003(6)
_cell_length_c                   15.7834(9)
_cell_measurement_reflns_used    3966
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.9290
_cell_measurement_theta_min      2.4710
_cell_volume                     2481.8(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 (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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     35.00  63.00   1.00   11.00    --   11.74 178.00-180.00   28
  2  \w    -38.00  34.00   1.00   11.00    --   11.74 -37.00   0.00   72
  3  \w    -58.00  47.00   1.00   11.00    --   11.74 -19.00 120.00  105
;
_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      0.0282836000
_diffrn_orient_matrix_UB_12      0.0420502000
_diffrn_orient_matrix_UB_13      0.0284288000
_diffrn_orient_matrix_UB_21      0.0424880000
_diffrn_orient_matrix_UB_22      -0.0222063000
_diffrn_orient_matrix_UB_23      -0.0099811000
_diffrn_orient_matrix_UB_31      -0.0061391000
_diffrn_orient_matrix_UB_32      0.0401059000
_diffrn_orient_matrix_UB_33      -0.0353349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11197
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90924
_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    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+2.7177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             4362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc00570f2.cif
_cod_data_source_block           283shang
_cod_depositor_comments
'Adding full bibliography for 7232870--7232871.cif.'
_cod_database_code               7232870
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C6(H6), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C11(H11), C14(H14), C28(H28), C24(H24), C18(H18),
 C27(H27), C3(H3), C19(H19), C4(H4), C26(H26), C25(H25), C22(H22), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.898