Alkylaluminium-catalyzed regioselective hydrophosphinylation of α,β-unsaturated ketones into γ-ketophosphine oxides
Chen, Yiwen; Pang, Ziyuan; Li, Gege; Yang, Xiaobo; Yan, Wenliang; Li, Qifeng; Dong, Xuan; Ma, Xiaoli; Yang, Zhi; Chemical Communications 61 (2025) 9666–9669; doi:10.1039/D5CC01440A

data_7134642
_publ_section_title
;
 Alkylaluminium-catalyzed regioselective hydrophosphinylation of
 \a,\b-unsaturated ketones into \g-ketophosphine oxides
;
_journal_issue                   53
_journal_name_full               'Chemical Communications'
_journal_page_first              9666
_journal_page_last               9669
_journal_paper_doi               10.1039/D5CC01440A
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C25 H27 O2 P)'
_chemical_formula_sum            'C50 H54 O4 P2'
_chemical_formula_weight         780.87
_chemical_name_systematic        P21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-23 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.347(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7275(3)
_cell_length_b                   20.7047(12)
_cell_length_c                   17.3578(11)
_cell_measurement_reflns_used    5969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0240
_cell_measurement_theta_min      3.5450
_cell_volume                     2057.8(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12550
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         3.522
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.308
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Flack x determined using 2271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(8)
_refine_ls_extinction_coef       0.013(5)
_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   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     984
_refine_ls_number_reflns         7069
_refine_ls_number_restraints     1875
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.1083
_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^)+(0.1476P)^2^+11.7141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2806
_refine_ls_wR_factor_ref         0.2867
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                6217
_reflns_number_total             7069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01440a2.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7134639--7134642.cif.'
_cod_database_code               7134642
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 C50-C47 \\sim C1B-C57
 with sigma of 0.02
 C50-C48 \\sim C1B-C01L
 with sigma of 0.04
 C47-C48 \\sim C57-C01L
 with sigma of 0.02
 C22-C23 \\sim C1X-C62
 with sigma of 0.02
 C46-C48 \\sim C51-C01L
 with sigma of 0.04
 C49-C48 \\sim C1A-C01L
 with sigma of 0.04
 C23-C25 \\sim C62-C63
 with sigma of 0.04
 C21-C23 \\sim C1S-C62
 with sigma of 0.04
 C24-C23 \\sim C1Z-C62
 with sigma of 0.04
 C46-C50 \\sim C51-C1B
 with sigma of 0.04
 C49-C50 \\sim C1A-C1B
 with sigma of 0.04
 C17-C18 \\sim C1T-C1N
 with sigma of 0.02
 P2-C32 \\sim P0-C65
 with sigma of 0.02
 O4-C46 \\sim O7-C51
 with sigma of 0.02
 C1-C3 \\sim C1Q-C1Y
 with sigma of 0.04
 P1-C19 \\sim P3-C1H
 with sigma of 0.04
 C44-C38 \\sim C0-C68
 with sigma of 0.02
 C16-C18 \\sim C1M-C1N
 with sigma of 0.04
 C44-C45 \\sim C0-C67
 with sigma of 0.02
 C35-C36 \\sim C60-C53
 with sigma of 0.02
 C13-C12 \\sim C1I-C1O
 with sigma of 0.02
 C45-C46 \\sim C67-C51
 with sigma of 0.02
 O1-C7 \\sim O5-C1F
 with sigma of 0.04
 C37-C32 \\sim C69-C65
 with sigma of 0.02
 C37-C36 \\sim C69-C53
 with sigma of 0.02
 C13-C9 \\sim C1I-C1J
 with sigma of 0.04
 C38-C39 \\sim C68-C00{
 with sigma of 0.02
 C2-C4 \\sim C1V-C1W
 with sigma of 0.04
 C38-C43 \\sim C68-C52
 with sigma of 0.02
 C35-C34 \\sim C60-C54
 with sigma of 0.02
 C32-C33 \\sim C65-C70
 with sigma of 0.02
 C7-C6 \\sim C1F-C1K
 with sigma of 0.02
 C1-C6 \\sim C1Q-C1K
 with sigma of 0.02
 C10-C11 \\sim C1P-C1U
 with sigma of 0.02
 P2-O3 \\sim P0-O0
 with sigma of 0.02
 C29-C28 \\sim C66-C71
 with sigma of 0.02
 O2-C20 \\sim O6-C1L
 with sigma of 0.04
 C14-C7 \\sim C1D-C1F
 with sigma of 0.04
 C33-C34 \\sim C70-C54
 with sigma of 0.02
 C8-C10 \\sim C1E-C1P
 with sigma of 0.04
 C7-C5 \\sim C1F-C1R
 with sigma of 0.04
 C21-C25 \\sim C1S-C63
 with sigma of 0.04
 P2-C44 \\sim P0-C0
 with sigma of 0.02
 P2-C29 \\sim P0-C66
 with sigma of 0.02
 C8-C9 \\sim C1E-C1J
 with sigma of 0.02
 C15-C14 \\sim C1G-C1D
 with sigma of 0.02
 C26-C27 \\sim C61-C56
 with sigma of 0.02
 C16-C17 \\sim C1M-C1T
 with sigma of 0.02
 C26-C31 \\sim C61-C55
 with sigma of 0.02
 C39-C40 \\sim C00{-C58
 with sigma of 0.02
 C19-C18 \\sim C1H-C1N
 with sigma of 0.02
 C43-C42 \\sim C52-C59
 with sigma of 0.02
 C21-C22 \\sim C1S-C1X
 with sigma of 0.02
 C49-C47 \\sim C1A-C57
 with sigma of 0.02
 C42-C41 \\sim C59-C1C
 with sigma of 0.02
 P1-C13 \\sim P3-C1I
 with sigma of 0.04
 C40-C41 \\sim C58-C1C
 with sigma of 0.02
 P1-C20 \\sim P3-C1L
 with sigma of 0.04
 O1-C14 \\sim O5-C1D
 with sigma of 0.04
 P2-C45 \\sim P0-C67
 with sigma of 0.04
 P2-C37 \\sim P0-C69
 with sigma of 0.04
 C29-C30 \\sim C66-C64
 with sigma of 0.02
 P2-C38 \\sim P0-C68
 with sigma of 0.04
 P2-C33 \\sim P0-C70
 with sigma of 0.04
 C8-C7 \\sim C1E-C1F
 with sigma of 0.04
 P2-C30 \\sim P0-C64
 with sigma of 0.04
 P2-C28 \\sim P0-C71
 with sigma of 0.04
 C7-C1 \\sim C1F-C1Q
 with sigma of 0.04
 C21-C24 \\sim C1S-C1Z
 with sigma of 0.04
 O3-C44 \\sim O0-C0
 with sigma of 0.04
 O3-C32 \\sim O0-C65
 with sigma of 0.04
 C6-C20 \\sim C1K-C1L
 with sigma of 0.04
 O3-C29 \\sim O0-C66
 with sigma of 0.04
 C12-C10 \\sim C1O-C1P
 with sigma of 0.04
 C24-C25 \\sim C1Z-C63
 with sigma of 0.04
 C30-C31 \\sim C64-C55
 with sigma of 0.02
 O4-C45 \\sim O7-C67
 with sigma of 0.04
 C15-C19 \\sim C1G-C1H
 with sigma of 0.04
 C14-C8 \\sim C1D-C1E
 with sigma of 0.04
 C46-C47 \\sim C51-C57
 with sigma of 0.02
 C28-C27 \\sim C71-C56
 with sigma of 0.02
 O2-C21 \\sim O6-C1S
 with sigma of 0.02
 C44-C46 \\sim C0-C51
 with sigma of 0.04
 C15-C16 \\sim C1G-C1M
 with sigma of 0.02
 C44-C39 \\sim C0-C00{
 with sigma of 0.04
 C14-C19 \\sim C1D-C1H
 with sigma of 0.02
 C44-C43 \\sim C0-C52
 with sigma of 0.04
 C8-C13 \\sim C1E-C1I
 with sigma of 0.02
 C7-C20 \\sim C1F-C1L
 with sigma of 0.02
 C35-C37 \\sim C60-C69
 with sigma of 0.04
 C35-C33 \\sim C60-C70
 with sigma of 0.04
 C9-C10 \\sim C1J-C1P
 with sigma of 0.02
 C1-C2 \\sim C1Q-C1V
 with sigma of 0.02
 C45-C38 \\sim C67-C68
 with sigma of 0.04
 C21-C20 \\sim C1S-C1L
 with sigma of 0.02
 C45-C47 \\sim C67-C57
 with sigma of 0.04
 C2-C3 \\sim C1V-C1Y
 with sigma of 0.02
 C6-C5 \\sim C1K-C1R
 with sigma of 0.02
 C37-C33 \\sim C69-C70
 with sigma of 0.04
 C12-C11 \\sim C1O-C1U
 with sigma of 0.02
 C5-C4 \\sim C1R-C1W
 with sigma of 0.02
 C22-C24 \\sim C1X-C1Z
 with sigma of 0.02
 C22-C25 \\sim C1X-C63
 with sigma of 0.02
 C38-C42 \\sim C68-C59
 with sigma of 0.04
 C4-C3 \\sim C1W-C1Y
 with sigma of 0.02
 C38-C40 \\sim C68-C58
 with sigma of 0.04
 P1-C15 \\sim P3-C1G
 with sigma of 0.04
 P1-C9 \\sim P3-C1J
 with sigma of 0.04
 P1-C6 \\sim P3-C1K
 with sigma of 0.04
 C32-C36 \\sim C65-C53
 with sigma of 0.04
 C32-C29 \\sim C65-C66
 with sigma of 0.04
 C32-C34 \\sim C65-C54
 with sigma of 0.04
 O1-C8 \\sim O5-C1E
 with sigma of 0.04
 O2-C22 \\sim O6-C1X
 with sigma of 0.04
 C15-C17 \\sim C1G-C1T
 with sigma of 0.04
 C36-C34 \\sim C53-C54
 with sigma of 0.04
 C29-C27 \\sim C66-C56
 with sigma of 0.04
 C14-C16 \\sim C1D-C1M
 with sigma of 0.04
 C29-C31 \\sim C66-C55
 with sigma of 0.04
 C14-C18 \\sim C1D-C1N
 with sigma of 0.04
 C8-C12 \\sim C1E-C1O
 with sigma of 0.04
 C7-C21 \\sim C1F-C1S
 with sigma of 0.04
 C30-C28 \\sim C64-C71
 with sigma of 0.04
 C30-C26 \\sim C64-C61
 with sigma of 0.04
 C13-C11 \\sim C1I-C1U
 with sigma of 0.04
 C9-C11 \\sim C1J-C1U
 with sigma of 0.04
 C46-C49 \\sim C51-C1A
 with sigma of 0.04
 C19-C17 \\sim C1H-C1T
 with sigma of 0.04
 C1-C5 \\sim C1Q-C1R
 with sigma of 0.04
 C28-C26 \\sim C71-C61
 with sigma of 0.04
 C27-C31 \\sim C56-C55
 with sigma of 0.04
 C2-C6 \\sim C1V-C1K
 with sigma of 0.04
 C39-C43 \\sim C00{-C52
 with sigma of 0.04
 C39-C41 \\sim C00{-C1C
 with sigma of 0.04
 C6-C4 \\sim C1K-C1W
 with sigma of 0.04
 C43-C41 \\sim C52-C1C
 with sigma of 0.04
 C5-C3 \\sim C1R-C1Y
 with sigma of 0.04
 C20-C22 \\sim C1L-C1X
 with sigma of 0.04
 C42-C40 \\sim C59-C58
 with sigma of 0.04
 O4-C47 \\sim O7-C57
 with sigma of 0.04
 P1-O1 \\sim P3-O5
 with sigma of 0.02
 P1-C14 \\sim P3-C1D
 with sigma of 0.02
 P1-C8 \\sim P3-C1E
 with sigma of 0.02
 C44-C32 \\sim C0-C65
 with sigma of 0.04
 P1-C7 \\sim P3-C1F
 with sigma of 0.02
 C44-C29 \\sim C0-C66
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C71 \\sim P2 \\sim O3 \\sim C44 \\sim C32 \\sim C29 \\sim C45 \\sim C38 \\sim
C37 \\sim C33 \\sim C30 \\sim C28 \\sim P0 \\sim O0 \\sim C0 \\sim C65 \\sim
C66 \\sim C46 \\sim C39 \\sim C43 \\sim C36 \\sim C34 \\sim C31 \\sim C27 \\sim
C67 \\sim C68 \\sim C69 \\sim C70 \\sim C64 \\sim O4 \\sim C47 \\sim C40 \\sim
C42 \\sim C35 \\sim C26 \\sim C51 \\sim C00{ \\sim C52 \\sim C53 \\sim C54
\\sim C55 \\sim C56 \\sim C49 \\sim C50 \\sim C48 \\sim C41 \\sim O7 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C1A \\sim C1B \\sim C01L \\sim
C1C: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
P1 \\sim P2 \\sim O3 \\sim O1 \\sim O2 \\sim O4 \\sim C44 \\sim C15 \\sim C35
\\sim C45 \\sim C14 \\sim C8 \\sim C37 \\sim C16 \\sim C7 \\sim C13 \\sim C38
\\sim C32 \\sim C36 \\sim C29 \\sim C9 \\sim C19 \\sim C1 \\sim C33 \\sim C34
\\sim C30 \\sim C46 \\sim C21 \\sim C28 \\sim C2 \\sim C26 \\sim C17 \\sim C6
\\sim C27 \\sim C39 \\sim C12 \\sim C10 \\sim C5 \\sim C18 \\sim C20 \\sim C43
\\sim C22 \\sim C4 \\sim C11 \\sim C49 \\sim C3 \\sim C42 \\sim C40 \\sim C41
\\sim C31 \\sim C50 \\sim C47 \\sim C24 \\sim C23 \\sim C25 \\sim C48: within
2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A
C10 \\sim P1 \\sim O1 \\sim C14 \\sim C8 \\sim C7 \\sim C15 \\sim C19 \\sim C13
\\sim C9 \\sim C6 \\sim C20 \\sim C16 \\sim C18 \\sim C12 \\sim C1 \\sim C5
\\sim C21 \\sim C17 \\sim C11 \\sim C2 \\sim C4 \\sim O2 \\sim C22 \\sim C3
\\sim C24 \\sim C23 \\sim C25 \\sim P3 \\sim O5 \\sim C1D \\sim C1E \\sim C1F
\\sim C1G \\sim C1H \\sim C1I \\sim C1J \\sim C1K \\sim C1L \\sim C1M \\sim C1N
\\sim C1O \\sim C1P \\sim C1Q \\sim C1R \\sim C1S \\sim C1T \\sim C1U \\sim C1V
\\sim C1W \\sim O6 \\sim C1X \\sim C1Y \\sim C1Z \\sim C62 \\sim C63: within 2A
with sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A
Uanis(C16) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C42) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C10) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C38) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C26) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(C64)=Sof(H64)=Sof(C66)=Sof(C71)=Sof(H71)=Sof(C56)=Sof(H56)=Sof(C61)=
 Sof(H61)=Sof(C55)=Sof(H55)=Sof(P0)=Sof(O0)=Sof(C0)=Sof(H0)=Sof(C65)=Sof(C67)=
 Sof(H67a)=Sof(H67b)=Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C51)=Sof(C53)=
 Sof(H53)=Sof(C54)=Sof(H54)=Sof(O7)=Sof(C57)=Sof(C59)=Sof(H59)=Sof(C52)=
 Sof(H52)=Sof(C68)=Sof(C00{)=Sof(H00{)=Sof(C58)=Sof(H58)=Sof(C1C)=Sof(H1C)=
 Sof(C60)=Sof(H60)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=Sof(C1B)=Sof(H1Ba)=
 Sof(H1Bb)=Sof(H1Bc)=Sof(C01L)=Sof(H01z)=Sof(H)=Sof(Ha)=1-FVAR(1)
 Sof(P2)=Sof(O3)=Sof(O4)=Sof(C44)=Sof(H007)=Sof(C35)=Sof(H009)=Sof(C45)=
 Sof(H00a)=Sof(H00b)=Sof(C37)=Sof(H00D)=Sof(C38)=Sof(C32)=Sof(C36)=Sof(H00J)=
 Sof(C29)=Sof(C33)=Sof(H00O)=Sof(C34)=Sof(H00P)=Sof(C30)=Sof(H00Q)=Sof(C46)=
 Sof(C28)=Sof(H00T)=Sof(C26)=Sof(H00V)=Sof(C27)=Sof(H00Y)=Sof(C39)=Sof(H00Z)=
 Sof(C43)=Sof(H015)=Sof(C49)=Sof(H01m)=Sof(H01n)=Sof(H01o)=Sof(C42)=Sof(H01p)=
 Sof(C40)=Sof(H01q)=Sof(C41)=Sof(H01r)=Sof(C31)=Sof(H01s)=Sof(C50)=Sof(H01t)=
 Sof(H01u)=Sof(H01v)=Sof(C47)=Sof(C48)=Sof(H01w)=Sof(H01x)=Sof(H01y)=FVAR(1)
 Sof(P3)=Sof(O5)=Sof(C1D)=Sof(C1E)=Sof(C1F)=Sof(H1F)=Sof(C1G)=Sof(H1G)=
 Sof(C1H)=Sof(H1H)=Sof(C1I)=Sof(H1I)=Sof(C1J)=Sof(H1J)=Sof(C1L)=Sof(H1La)=
 Sof(H1Lb)=Sof(C1M)=Sof(H1M)=Sof(C1N)=Sof(H1N)=Sof(C1O)=Sof(H1O)=Sof(C1P)=
 Sof(H1P)=Sof(C1S)=Sof(C1T)=Sof(H1T)=Sof(C1U)=Sof(H1U)=Sof(C1W)=Sof(H1W)=
 Sof(C1R)=Sof(H1R)=Sof(C1K)=Sof(C1Q)=Sof(H1Q)=Sof(C1V)=Sof(H1V)=Sof(C1Y)=
 Sof(H1Y)=Sof(O6)=Sof(C1X)=Sof(C1Z)=Sof(H1Za)=Sof(H1Zb)=Sof(H1Zc)=Sof(C62)=
 Sof(H62a)=Sof(H62b)=Sof(H62c)=Sof(C63)=Sof(H63a)=Sof(H63b)=Sof(H63c)=1-FVAR(2)
 Sof(P1)=Sof(O1)=Sof(O2)=Sof(C15)=Sof(H008)=Sof(C14)=Sof(C8)=Sof(C16)=
 Sof(H00E)=Sof(C7)=Sof(H00F)=Sof(C13)=Sof(H00G)=Sof(C9)=Sof(H00L)=Sof(C19)=
 Sof(H00M)=Sof(C1)=Sof(H00N)=Sof(C21)=Sof(C2)=Sof(H00U)=Sof(C17)=Sof(H00W)=
 Sof(C6)=Sof(C12)=Sof(H010)=Sof(C10)=Sof(H011)=Sof(C5)=Sof(H012)=Sof(C18)=
 Sof(H013)=Sof(C20)=Sof(H01a)=Sof(H01b)=Sof(C22)=Sof(C4)=Sof(H017)=Sof(C11)=
 Sof(H018)=Sof(C3)=Sof(H01c)=Sof(C24)=Sof(H01d)=Sof(H01e)=Sof(H01f)=Sof(C23)=
 Sof(H01g)=Sof(H01h)=Sof(H01i)=Sof(C25)=Sof(H01j)=Sof(H01k)=Sof(H01l)=FVAR(2)
5.a Riding coordinates:
 C48(H01w,H01x,H01y), C1B(H1Ba,H1Bb,H1Bc), C01L(H01z,H,Ha), C62(H62a,H62b,H62c)
5.b Ternary CH refined with riding coordinates:
 C44(H007), C7(H00F), C0(H0), C1F(H1F)
5.c Secondary CH2 refined with riding coordinates:
 C45(H00a,H00b), C20(H01a,H01b), C67(H67a,H67b), C1L(H1La,H1Lb)
5.d Aromatic/amide H refined with riding coordinates:
 C15(H008), C35(H009), C37(H00D), C16(H00E), C13(H00G), C36(H00J), C9(H00L),
 C19(H00M), C1(H00N), C33(H00O), C34(H00P), C30(H00Q), C28(H00T), C2(H00U),
 C26(H00V), C17(H00W), C27(H00Y), C39(H00Z), C12(H010), C10(H011), C5(H012),
 C18(H013), C43(H015), C4(H017), C11(H018), C3(H01c), C42(H01p), C40(H01q),
 C41(H01r), C31(H01s), C64(H64), C71(H71), C56(H56), C61(H61), C55(H55),
 C69(H69), C70(H70), C53(H53), C54(H54), C59(H59), C52(H52), C00{(H00{),
 C58(H58), C1C(H1C), C60(H60), C1G(H1G), C1H(H1H), C1I(H1I), C1J(H1J), C1M(H1M),
  C1N(H1N), C1O(H1O), C1P(H1P), C1T(H1T), C1U(H1U), C1W(H1W), C1R(H1R),
 C1Q(H1Q), C1V(H1V), C1Y(H1Y)
5.e Fitted hexagon refined as free rotating group:
 C64(C66,C71,C56,C61,C55), C59(C52,C68,C00{,C58,C1C), C1W(C1R,C1K,C1Q,C1V,C1Y)
5.f Idealised Me refined as rotating group:
 C49(H01m,H01n,H01o), C50(H01t,H01u,H01v), C24(H01d,H01e,H01f), C23(H01g,H01h,
 H01i), C25(H01j,H01k,H01l), C1A(H1Aa,H1Ab,H1Ac), C1Z(H1Za,H1Zb,H1Zc), C63(H63a,
 H63b,H63c)
;
_shelx_res_checksum              6380
_shelx_hkl_checksum              22013
_olex2_submission_special_instructions 'No special instructions were received'