Metal-Free Visible Light-Mediated Photocatalysis: Controlling Intramolecular [2 + 2] Photocycloaddition of Enones through Axial Chirality.
Clay, Anthony; Vallavoju, Nandini; Krishnan, Retheesh; Ugrinov, Angel; Sivaguru, Jayaraman; The Journal of organic chemistry 81 (2016) 7191–7200; doi:10.1021/acs.joc.6b01066

data_4036958
_publ_section_title
;
 Metal-Free Visible Light-Mediated Photocatalysis: Controlling
 Intramolecular [2 + 2] Photocycloaddition of Enones through Axial
 Chirality.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7191
_journal_page_last               7200
_journal_paper_doi               10.1021/acs.joc.6b01066
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H33 N O4'
_chemical_formula_sum            'C24 H33 N O4'
_chemical_formula_weight         399.51
_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     direct
_audit_creation_date             2016-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                101.858(2)
_cell_angle_beta                 99.6140(10)
_cell_angle_gamma                105.0390(10)
_cell_formula_units_Z            4
_cell_length_a                   11.7956(4)
_cell_length_b                   12.4371(4)
_cell_length_c                   16.1837(5)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.656
_cell_measurement_theta_min      2.869
_cell_volume                     2182.13(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.95
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27433
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.798
_diffrn_reflns_theta_max         66.797
_diffrn_reflns_theta_min         2.869
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.9368.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       chunk
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         7541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0399P)^2^+1.0265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6486
_reflns_number_total             7541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01066_si_002.cif
_cod_data_source_block           ct-2c
_cod_original_cell_volume        2182.12(12)
_cod_database_code               4036958
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.870
_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. Others
 Sof(C26B)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C28B)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C30B)=Sof(H30A)=Sof(H30B)=Sof(H30C)=1-FVAR(1)
 Sof(C25B)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C29B)=Sof(H29A)=Sof(H29B)=
 Sof(H29C)=Sof(C27B)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
 Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(O30A)=1-FVAR(2)
 Sof(O28A)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C6A(H6A), C12A(H12A), C12B(H12B), C6B(H6B)
3.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11C,H11D), C13A(H13C,
 H13D), C4B(H4BA,H4BB), C9B(H9BA,H9BB), C10B(H10A,H10B), C11B(H11A,H11B),
 C13B(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C20A(H20A), C22A(H22A), C22B(H22B), C20B(H20B), C19B(H19B)
3.d Idealised Me refined as rotating group:
 C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F), C27A(H27D,H27E,H27F), C25A(H25D,
 H25E,H25F), C26A(H26D,H26E,H26F), C14B(H14A,H14B,H14C), C32B(H32A,H32B,H32C),
 C15B(H15A,H15B,H15C), C31A(H31A,H31B,H31C), C25B(H25A,H25B,H25C), C29B(H29A,
 H29B,H29C), C27B(H27A,H27B,H27C), C26B(H26A,H26B,H26C), C28B(H28A,H28B,H28C),
 C30B(H30A,H30B,H30C), C29A(H29D,H29E,H29F)
;
_shelx_res_checksum              26191
_shelx_hkl_checksum              94000
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 'Sep 6, 2014'
_olex2_date_sample_submission    'Sep 3, 2014'
_olex2_submission_special_instructions 'No special instructions were received'