Visible-Light-Triggered Selective Intermolecular [2+2] Cycloaddition of Extended Enones: 2-Oxo-3-enoates and 2,4-Dien-1-ones with Olefins.
Zhao, Lei-Min; Lei, Tao; Liao, Rong-Zhen; Xiao, Hongyan; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; The Journal of organic chemistry 84 (2019) 9257–9269; doi:10.1021/acs.joc.9b01273

data_4034207
_publ_section_title
;
 Visible-Light-Triggered Selective Intermolecular [2+2] Cycloaddition of
 Extended Enones: 2-Oxo-3-enoates and 2,4-Dien-1-ones with Olefins.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9257
_journal_page_last               9269
_journal_paper_doi               10.1021/acs.joc.9b01273
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H25 Br O'
_chemical_formula_sum            'C27 H25 Br O'
_chemical_formula_weight         445.38
_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
_audit_creation_date             2016-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-07-20 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                67.84(3)
_cell_angle_beta                 79.96(3)
_cell_angle_gamma                73.35(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0295(18)
_cell_length_b                   10.820(2)
_cell_length_c                   12.555(3)
_cell_measurement_reflns_used    2264
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.6360
_cell_measurement_theta_min      3.9310
_cell_volume                     1085.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -56.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000   60.0000 91

  2 omega  -20.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -99.0000  -30.0000 73

  3 omega  -16.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000 -150.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0142724000
_diffrn_orient_matrix_UB_12      0.0582005000
_diffrn_orient_matrix_UB_13      -0.0472490000
_diffrn_orient_matrix_UB_21      -0.0721925000
_diffrn_orient_matrix_UB_22      0.0098405000
_diffrn_orient_matrix_UB_23      -0.0208015000
_diffrn_orient_matrix_UB_31      -0.0366727000
_diffrn_orient_matrix_UB_32      0.0428676000
_diffrn_orient_matrix_UB_33      0.0328154000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6858
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.410
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.095
_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     264
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0421P)^2^+0.3429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01273_si_002.cif
_cod_data_source_block           exp_7172a
_cod_original_cell_volume        1085.4(5)
_cod_database_code               4034207
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C27 H25 Br1 O1'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.832
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'