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_1566149
_publ_section_title
;
 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         'C38 H34 N2 O2'
_chemical_formula_sum            'C38 H34 N2 O2'
_chemical_formula_weight         550.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-02
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6653(2)
_cell_length_b                   10.33692(10)
_cell_length_c                   28.5425(3)
_cell_measurement_reflns_used    9128
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      70.13
_cell_measurement_theta_min      3.09
_cell_volume                     5802.08(10)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      220.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 PhotonII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            97589
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.241
_diffrn_reflns_theta_min         3.096
_diffrn_source                   microfocus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1011 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.8219. 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    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0382P)^2^+1.5520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4699
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06719b2.cif
_cod_data_source_block           as295long_0ma_a
_cod_original_cell_volume        5802.10(11)
_cod_database_code               1566149
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.915
_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
2. Uiso/Uaniso restraints and constraints
C11A \\sim C11: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
3. Others
 Sof(H71C)=Sof(H71D)=Sof(C51A)=Sof(H51A)=Sof(C61A)=Sof(H61A)=Sof(C11A)=
 Sof(C21A)=Sof(H21A)=Sof(C31A)=Sof(H31A)=Sof(C41A)=Sof(H41A)=1-FVAR(1)
 Sof(H71A)=Sof(H71B)=Sof(C61)=Sof(H61)=Sof(C11)=Sof(C21)=Sof(H21)=Sof(C31)=
 Sof(H31)=Sof(C41)=Sof(H41)=Sof(C51)=Sof(H51)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C121(H121), C112(H112), C102(H102), C92(H92), C132(H132)
4.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C71(H71C,H71D), C122(H12A,H12B), C72(H72A,H72B), C151(H15A,
 H15B), C111(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C192(H192), C182(H182), C172(H172), C61(H61), C21(H21), C31(H31), C41(H41),
 C51(H51), C162(H162), C152(H152), C62(H62), C52(H52), C42(H42), C32(H32),
 C22(H22), C161(H161), C171(H171), C181(H181), C191(H191), C51A(H51A),
 C61A(H61A), C21A(H21A), C31A(H31A), C41A(H41A)
4.d Fitted hexagon refined as free rotating group:
 C61(C11,C21,C31,C41,C51), C51A(C61A,C11A,C21A,C31A,C41A)
;
_shelx_res_checksum              52098
_olex2_exptl_crystal_mounting_method CryoLoop
_olex2_submission_special_instructions 'No special instructions were received'