Dimerizing Cascades of Enallenamides Reveal the Visible-Light- Promoted Activation of Cumulated C-C Double Bonds
Maestri, Giovanni; Serafino, Andrea; Chiminelli, Maurizio; Balestri, Davide; Marchiò, Luciano; Bigi, Franca; Maggi, Raimondo; Malacria, Max; Chemical Science  (2022) –; doi:10.1039/D1SC06719B

data_1566147
_publ_section_title
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 Dimerizing Cascades of Enallenamides Reveal the Visible-Light- Promoted
 Activation of Cumulated C-C Double Bonds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06719B
_journal_year                    2022
_chemical_formula_moiety         'C40 H38 N2 O2'
_chemical_formula_sum            'C40 H38 N2 O2'
_chemical_formula_weight         578.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                107.2720(10)
_cell_angle_beta                 102.9910(10)
_cell_angle_gamma                90.2390(10)
_cell_formula_units_Z            2
_cell_length_a                   10.4645(2)
_cell_length_b                   12.4559(2)
_cell_length_c                   12.5578(2)
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    200
_cell_measurement_theta_max      70.293
_cell_measurement_theta_min      3.794
_cell_volume                     1518.60(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      200
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 venture PhotonII area detector'
_diffrn_measurement_method       'omega and theta scans'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            48468
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.436
_diffrn_reflns_theta_min         3.794
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0668 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.8902.
The \l/2 correction factor is Not present.
;
_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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0744P)^2^+0.4552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4824
_reflns_number_total             5765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06719b2.cif
_cod_data_source_block           as520a_0m
_cod_database_code               1566147
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H34C)=Sof(H34D)=Sof(C40A)=Sof(H40A)=Sof(C39A)=Sof(H39A)=Sof(C38A)=
 Sof(H38A)=Sof(C37A)=Sof(H37A)=Sof(C36A)=Sof(H36A)=Sof(C35A)=1-FVAR(1)
 Sof(C35)=Sof(C40)=Sof(H40)=Sof(C39)=Sof(H39)=Sof(C38)=Sof(H38)=Sof(C37)=
 Sof(H37)=Sof(C36)=Sof(H36)=Sof(H34A)=Sof(H34B)=FVAR(1)
 Sof(H27C)=Sof(H27D)=Sof(C31A)=Sof(H31A)=Sof(C30A)=Sof(H30A)=Sof(C29A)=
 Sof(H29A)=Sof(C28A)=Sof(C33A)=Sof(H33A)=Sof(C32A)=Sof(H32A)=1-FVAR(2)
 Sof(H27A)=Sof(H27B)=Sof(C30)=Sof(H30)=Sof(C29)=Sof(H29)=Sof(C28)=Sof(C33)=
 Sof(H33)=Sof(C32)=Sof(H32)=Sof(C31)=Sof(H31)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C2(H2), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C27(H27A,H27B), C27(H27C,H27D), C34(H34A,H34B), C34(H34C,H34D)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C22(H22), C26(H26), C40(H40), C39(H39), C38(H38), C37(H37), C36(H36),
 C15(H15), C23(H23), C24(H24), C25(H25), C19(H19), C17(H17), C18(H18), C16(H16),
  C30(H30), C29(H29), C33(H33), C32(H32), C31(H31), C40A(H40A), C39A(H39A),
 C38A(H38A), C37A(H37A), C36A(H36A), C31A(H31A), C30A(H30A), C29A(H29A),
 C33A(H33A), C32A(H32A)
3.d Fitted hexagon refined as free rotating group:
 C35(C40,C39,C38,C37,C36), C30(C29,C28,C33,C32,C31), C40A(C39A,C38A,C37A,C36A,
 C35A), C31A(C30A,C29A,C28A,C33A,C32A)
3.e X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.f Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'