Visible light-induced selenylative spirocyclization of biaryl ynones toward the formation of selenated spiro[5.5]trienones.
Chen, Zhichao; Zheng, Xinran; Zhou, Shu-Feng; Cui, Xiuling; Organic & biomolecular chemistry 20 (2022) 5779–5783; doi:10.1039/d2ob01006b

data_7158745
_publ_section_title
;
 Visible light-induced selenylative spirocyclization of biaryl ynones
 toward the formation of selenated spiro[5.5]trienones.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5779
_journal_page_last               5783
_journal_paper_doi               10.1039/d2ob01006b
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C47 H49 Dy N6 O2, 3(C4 H8 O)'
_chemical_formula_sum            'C59 H73 Dy N6 O5'
_chemical_formula_weight         1108.73
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2b6q9l
_audit_creation_date             2022-02-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-11 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.70(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.124(3)
_cell_length_b                   14.155(3)
_cell_length_c                   22.873(5)
_cell_measurement_reflns_used    8779
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     5310(2)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            48842
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.713
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    1.462
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             2300
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.887
_refine_diff_density_min         -1.816
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.0055(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         8779
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0346P)^2^+88.5088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8070
_reflns_number_total             8779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01006b2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7158745--7158746.cif.'
_cod_database_code               7158745
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Others
 Fixed Sof: H47A(0.6) H47B(0.6) H47C(0.4) H47D(0.4) H44A(0.7) H44B(0.7)
 H44C(0.3) H44D(0.3) C46(0.6) H46A(0.6) H46B(0.6) C45(0.7) H45A(0.7) H45B(0.7)
 C52(0.7) H52A(0.7) H52B(0.7) H54A(0.7) H54B(0.7) H54C(0.3) H54D(0.3) C53(0.7)
 H53A(0.7) H53B(0.7) C46A(0.4) H46C(0.4) H46D(0.4) C45A(0.3) H45C(0.3)
 H45D(0.3) C52A(0.3) H52C(0.3) H52D(0.3) C53A(0.3) H53C(0.3) H53D(0.3)
 Fixed Uiso: H3(0.033) H2(0.029) H9(0.033) H21(0.036) H17(0.033) H1(0.028)
 H5(0.032) H24(0.036) H23(0.032) H27(0.034) H29(0.032) H20(0.037) H12(0.043)
 H15(0.037) H8(0.039) H19(0.04) H35(0.035) H30(0.037) H11(0.038) H6(0.041)
 H25(0.043) H33(0.039) H39(0.035) H32(0.045) H7(0.039) H38(0.039) H37(0.041)
 H56A(0.064) H56B(0.064) H49A(0.061) H49B(0.061) H26(0.039) H48A(0.051)
 H48B(0.051) H31(0.038) H36(0.041) H58A(0.067) H58B(0.067) H13(0.048)
 H14(0.045) H59A(0.057) H59B(0.057) H57A(0.061) H57B(0.061) H50A(0.065)
 H50B(0.065) H47A(0.044) H47B(0.044) H47C(0.044) H47D(0.044) H43A(0.049)
 H43B(0.049) H44A(0.041) H44B(0.041) H44C(0.041) H44D(0.041) H42A(0.058)
 H42B(0.058) H41A(0.064) H41B(0.064) H51A(0.067) H51B(0.067) H40A(0.065)
 H40B(0.065) H46A(0.046) H46B(0.046) H18(0.037) H45A(0.038) H45B(0.038)
 H52A(0.079) H52B(0.079) H55A(0.071) H55B(0.071) H54A(0.072) H54B(0.072)
 H54C(0.072) H54D(0.072) H53A(0.093) H53B(0.093) H46C(0.03) H46D(0.03)
 H45C(0.036) H45D(0.036) H52C(0.073) H52D(0.073) H53C(0.099) H53D(0.099)
 Fixed X: H3(0.242486) H2(0.373149) H9(0.575089) H21(0.41244) H17(0.552807)
 H1(0.450806) H5(0.485568) H24(0.241672) H23(0.331465) H27(0.16731)
 H29(0.288116) H20(0.510645) H12(0.294161) H15(0.287185) H8(0.682489)
 H19(0.631342) H35(0.329604) H30(0.227757) H11(0.351705) H6(0.597872)
 H25(0.117521) H33(0.146603) H39(0.285235) H32(0.089042) H7(0.695453)
 H38(0.313901) H37(0.35189) H56A(0.018317) H56B(0.079804) H49A(0.250795)
 H49B(0.238878) H26(0.081539) H48A(0.136808) H48B(0.160216) H31(0.126924)
 H36(0.355413) H58A(0.000976) H58B(0.084949) H13(0.23002) H14(0.225877)
 H59A(0.138935) H59B(0.056057) H57A(-0.039866) H57B(0.039043) H50A(0.187971)
 H50B(0.160298) H47A(0.476722) H47B(0.388086) H47C(0.395242) H47D(0.440483)
 H43A(0.198207) H43B(0.129511) H44A(0.43919) H44B(0.50906) H44C(0.441963)
 H44D(0.521434) H42A(0.05166) H42B(0.12409) H41A(0.028746) H41B(0.046607)
 H51A(0.074245) H51B(0.040044) H40A(0.135618) H40B(0.175408) H46A(0.440798)
 H46B(0.518638) H18(0.651559) H45A(0.538793) H45B(0.583522) H52A(-0.13652)
 H52B(-0.106245) H55A(0.033823) H55B(0.068806) H54A(-0.030121) H54B(-0.034479)
 H54C(-0.049013) H54D(-0.016755) H53A(-0.153651) H53B(-0.151414) H46C(0.563886)
 H46D(0.518168) H45C(0.561076) H45D(0.468032) H52C(-0.150473) H52D(-0.113844)
 H53C(-0.139495) H53D(-0.168508)
 Fixed Y: H3(0.934081) H2(1.093702) H9(0.945246) H21(0.988261) H17(0.908992)
 H1(0.711502) H5(0.684217) H24(1.360716) H23(1.23653) H27(1.113019)
 H29(1.185752) H20(0.931756) H12(0.493232) H15(0.812918) H8(0.916518)
 H19(0.865205) H35(0.828258) H30(1.325324) H11(0.603849) H6(0.654154)
 H25(1.366836) H33(1.039375) H39(0.692819) H32(1.182316) H7(0.769961)
 H38(0.548571) H37(0.544113) H56A(0.952285) H56B(0.959825) H49A(1.047306)
 H49B(1.087819) H26(1.245611) H48A(1.119205) H48B(1.193706) H31(1.324118)
 H36(0.683891) H58A(0.714274) H58B(0.708014) H13(0.542395) H14(0.704211)
 H59A(0.760264) H59B(0.81393) H57A(0.838106) H57B(0.82388) H50A(0.941457)
 H50B(0.929103) H47A(1.005487) H47B(1.053489) H47C(1.092653) H47D(0.992317)
 H43A(0.933857) H43B(0.992147) H44A(1.172455) H44B(1.096495) H44C(1.166664)
 H44D(1.098426) H42A(0.873908) H42B(0.797275) H41A(0.874511) H41B(0.764111)
 H51A(1.006663) H51B(0.966289) H40A(0.854989) H40B(0.773897) H46A(1.207436)
 H46B(1.157916) H18(0.853457) H45A(1.237489) H45B(1.137479) H52A(1.061334)
 H52B(1.155243) H55A(1.129636) H55B(1.025691) H54A(0.955123) H54B(1.056552)
 H54C(1.069565) H54D(0.964949) H53A(1.085816) H53B(0.982452) H46C(1.060871)
 H46D(1.127169) H45C(1.208619) H45D(1.225129) H52C(1.063816) H52D(0.960306)
 H53C(0.934298) H53D(1.041823)
 Fixed Z: H3(0.914231) H2(0.653338) H9(0.883277) H21(0.594955) H17(0.761959)
 H1(0.789907) H5(0.896823) H24(0.616268) H23(0.6504) H27(0.724877)
 H29(0.824939) H20(0.552164) H12(0.678016) H15(0.627732) H8(0.96703)
 H19(0.613453) H35(0.978246) H30(0.841587) H11(0.75299) H6(0.980722)
 H25(0.639216) H33(0.90821) H39(0.816105) H32(0.926979) H7(1.017349)
 H38(0.867544) H37(0.972835) H56A(0.940629) H56B(1.008355) H49A(0.560067)
 H49B(0.492136) H26(0.694954) H48A(0.568948) H48B(0.523549) H31(0.89283)
 H36(1.029402) H58A(0.934311) H58B(0.988806) H13(0.577275) H14(0.55349)
 H59A(0.913641) H59B(0.877492) H57A(0.978354) H57B(1.036359) H50A(0.465458)
 H50B(0.526611) H47A(0.937949) H47B(0.926232) H47C(0.924487) H47D(0.933024)
 H43A(0.634073) H43B(0.654348) H44A(0.807216) H44B(0.80786) H44C(0.800648)
 H44D(0.818829) H42A(0.599317) H42B(0.620581) H41A(0.693993) H41B(0.685637)
 H51A(0.417131) H51B(0.470576) H40A(0.777539) H40B(0.745945) H46A(0.928376)
 H46B(0.975323) H18(0.718615) H45A(0.880815) H45B(0.901531) H52A(0.653643)
 H52B(0.692977) H55A(0.772645) H55B(0.767391) H54A(0.798998) H54B(0.830228)
 H54C(0.820988) H54D(0.813114) H53A(0.762734) H53B(0.733729) H46C(0.948602)
 H46D(0.98647) H45C(0.904616) H45D(0.904366) H52C(0.666967) H52D(0.666552)
 H53C(0.74004) H53D(0.743793)
;
_shelx_res_checksum              18597
_olex2_submission_special_instructions 'No special instructions were received'