Visible Light-Mediated Decarboxylation Rearrangement Cascade of ω-Aryl- N-(acyloxy)phthalimides.
Faderl, Christian; Budde, Simon; Kachkovskyi, Georgiy; Rackl, Daniel; Reiser, Oliver; The Journal of organic chemistry 83 (2018) 12192–12206; doi:10.1021/acs.joc.8b01538

data_4035206
_publ_section_title
;
 Visible Light-Mediated Decarboxylation Rearrangement Cascade of \w-Aryl-
 N-(acyloxy)phthalimides.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12192
_journal_page_last               12206
_journal_paper_doi               10.1021/acs.joc.8b01538
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H23 N O4'
_chemical_formula_sum            'C16 H23 N O4'
_chemical_formula_weight         293.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7745(2)
_cell_length_b                   9.69517(16)
_cell_length_c                   23.1634(4)
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    162.46(10)
_cell_measurement_theta_max      73.5310
_cell_measurement_theta_min      5.5560
_cell_volume                     3093.38(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.12a (release 12-09-2013 CrysAlis171 .NET)
(compiled Sep 12 2013,13:51:24)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.12a (release 12-09-2013 CrysAlis171 .NET)
(compiled Sep 12 2013,13:51:24)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.12a (release 12-09-2013 CrysAlis171 .NET)
(compiled Sep 12 2013,13:51:24)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      162.46(10)
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega -109.00  -16.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  -57.0000   30.0000 186

  2 omega  -13.00   75.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2064  -99.0000 -150.0000 176

  3 omega   36.00   65.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -180.0000 58

  4 omega   79.00  154.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   61.0000  -30.0000 150

  5 omega   36.00   64.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -150.0000 56

  6 omega   29.00   56.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -94.0000   90.0000 54

  7 omega   34.00   67.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  150.0000 66

  8 omega   81.00  108.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -94.0000   90.0000 54

  9 omega   49.00  127.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -61.0000   60.0000 156

 10 omega   35.00   69.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -120.0000 68

 11 omega   24.00  105.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -94.0000   30.0000 162

 12 omega -117.00  -55.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064 -154.0000 -108.0000 124

 13 omega -120.00   -8.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  -77.0000  -90.0000 224

 14 omega -117.00  -15.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  -37.0000  120.0000 204

 15 omega   76.00  101.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000   90.0000 50

 16 omega   76.00  158.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000 -180.0000 164

 17 omega   76.00  158.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000  -90.0000 164
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0982965000
_diffrn_orient_matrix_UB_12      0.0033153000
_diffrn_orient_matrix_UB_13      0.0317080000
_diffrn_orient_matrix_UB_21      0.0082717000
_diffrn_orient_matrix_UB_22      -0.1578986000
_diffrn_orient_matrix_UB_23      -0.0062904000
_diffrn_orient_matrix_UB_31      0.0527112000
_diffrn_orient_matrix_UB_32      0.0185914000
_diffrn_orient_matrix_UB_33      -0.0580648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17335
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.533
_diffrn_reflns_theta_min         3.817
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.12a (release 12-09-2013 CrysAlis171 .NET)
(compiled Sep 12 2013,13:51:24)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1317
_exptl_crystal_size_min          0.0702
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5726
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0516
_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^)+(0.1050P)^2^+0.5233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                4998
_reflns_number_total             5726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01538_si_002.cif
_cod_data_source_block           m096
_cod_database_code               4035206
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C16 H23 N1 O4'
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4A) = Uanis(O4)
Uanis(C11) = Uanis(C11A)
Uanis(O8) = Uanis(O7A)
Uanis(C27A) = Uanis(C27)
Uanis(C26A) = Uanis(C26)
Uanis(C15) = Uanis(C15A)
Uanis(C10A) = Uanis(C10)
Uanis(C19) = Uanis(C19A)
Uanis(C31A) = Uanis(C31)
Uanis(C4A) = Uanis(C4)
Uanis(O3A) = Uanis(O3)
Uanis(C15) = Uanis(C16A) = Uanis(C16)
Uanis(O8) = Uanis(O8A)
Uanis(C32) = Uanis(C32A)
Uanis(C30A) = Uanis(C30)
Uanis(C13) = Uanis(C13A)
Uanis(C3) = Uanis(C3A)
3. Others
 Sof(H5BC)=Sof(H5BD)=Sof(C3A)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C10A)=Sof(C11A)=
 Sof(C13A)=Sof(H13A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C14A)=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(O2A)=
 Sof(O3A)=Sof(O4A)=Sof(H21C)=Sof(H21D)=Sof(O7A)=Sof(O8A)=Sof(C27A)=Sof(C19A)=
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C26A)=Sof(C29A)=Sof(H29A)=Sof(C32A)=
 Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(O6A)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=
 Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(H5A)=Sof(H5B)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C10)=Sof(C11)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(O2)=Sof(O3)=
 Sof(O4)=Sof(H21A)=Sof(H21B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=
 Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(O6)=Sof(C19)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 Sof(C26)=Sof(C27)=Sof(C29)=Sof(H29)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=
 Sof(O7)=Sof(O8)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C5(H5BC,H5BD), C4(H4A,H4B), C4A(H4AA,H4AB), C21(H21A,H21B),
 C21(H21C,H21D), C20(H20A,H20B), C20A(H20C,H20D)
4.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C14A(H14D,H14E,
 H14F), C15A(H15D,H15E,H15F), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C32A(H32D,H32E,H32F), C31A(H31D,H31E,H31F)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C13A(H13A), C29(H29), C29A(H29A)
4.d Idealised Me refined as rotating group:
 C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              13504
_shelx_hkl_checksum              41
_olex2_submission_special_instructions 'No special instructions were received'