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_1566148
_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         'C19 H16 Cl N O'
_chemical_formula_sum            'C19 H16 Cl N O'
_chemical_formula_weight         309.78
_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             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                102.666(7)
_cell_angle_beta                 94.860(7)
_cell_angle_gamma                105.758(7)
_cell_formula_units_Z            2
_cell_length_a                   5.8886(5)
_cell_length_b                   10.0297(9)
_cell_length_c                   13.4799(11)
_cell_measurement_reflns_used    2476
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.203
_cell_measurement_theta_min      3.401
_cell_volume                     738.69(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_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  0.0843
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8836
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         3.401
_diffrn_source                   microfocus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1239 before and 0.0801 after correction. The Ratio of minimum to maximum transmission is 0.7627. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0687
_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^)+(0.0961P)^2^+0.2432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1907
_reflns_number_total             2763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06719b2.cif
_cod_data_source_block           cu_as495_f13_rd_0m
_cod_original_cell_volume        738.69(11)
_cod_database_code               1566148
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.044) H2(0.047) H12(0.051) H6(0.045) H19(0.046) H15(0.048)
 H17A(0.053) H17B(0.053) H13(0.052) H3(0.046) H7(0.048) H8(0.045) H14(0.052)
 H16(0.047) H10A(0.052) H10B(0.052)
 Fixed X: H5(0.8916) H2(0.069) H12(0.3577) H6(0.6377) H19(1.163) H15(0.6347)
 H17A(0.9868) H17B(1.073) H13(0.4283) H3(0.3231) H7(0.9649) H8(0.5812)
 H14(0.7261) H16(0.5644) H10A(0.577) H10B(0.4901)
 Fixed Y: H5(0.1749) H2(-0.0192) H12(0.2051) H6(0.0847) H19(0.3753)
 H15(0.6714) H17A(0.3757) H17B(0.5412) H13(0.2758) H3(0.0773) H7(0.2064)
 H8(0.2366) H14(0.5017) H16(0.6032) H10A(0.4198) H10B(0.2544)
 Fixed Z: H5(0.8063) H2(0.6902) H12(0.1667) H6(0.9158) H19(0.3216) H15(0.167)
 H17A(0.1003) H17B(0.1634) H13(0.0152) H3(0.5831) H7(0.637) H8(0.5154)
 H14(0.0312) H16(0.3203) H10A(0.4187) H10B(0.3544)
;
_shelx_res_checksum              86721
_olex2_exptl_crystal_mounting_method CryoLoop
_olex2_submission_special_instructions 'No special instructions were received'