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_4036954
_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         'C22 H29 N O3'
_chemical_formula_sum            'C22 H29 N O3'
_chemical_formula_weight         355.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2407(5)
_cell_length_b                   18.9857(6)
_cell_length_c                   12.4646(4)
_cell_measurement_reflns_used    8813
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      66.78
_cell_measurement_theta_min      4.66
_cell_volume                     3843.3(2)
_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      100.94
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18521
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.885
_diffrn_reflns_theta_max         66.885
_diffrn_reflns_theta_min         4.658
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9203.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0479P)^2^+1.4023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3053
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01066_si_002.cif
_cod_data_source_block           cc-2a
_cod_database_code               4036954
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.818
_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.a Ternary CH refined with riding coordinates:
 C11(H11), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              25530
_shelx_hkl_checksum              13646
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'