Metal-Free [2 + 2]-Photocycloaddition of (Z)-4-Aryliden-5(4H)-Oxazolones as Straightforward Synthesis of 1,3-Diaminotruxillic Acid Precursors: Synthetic Scope and Mechanistic Studies
García-Montero, Angel; Rodriguez, Antonio M.; Juan, Alberto; Velders, Aldrik H.; Denisi, Antonio; Jiménez-Osés, Gonzalo; Gómez-Bengoa, Enrique; Cativiela, Carlos; Gómez, Maria Victoria; Urriolabeitia, Esteban P.; ACS Sustainable Chemistry & Engineering 5 (2017) 8370–; doi:10.1021/acssuschemeng.7b02140

data_4517020
_publ_section_title
;
 Metal-Free [2 + 2]-Photocycloaddition of (Z)-4-Aryliden-5(4H)-Oxazolones
 as Straightforward Synthesis of 1,3-Diaminotruxillic Acid Precursors:
 Synthetic Scope and Mechanistic Studies
;
_journal_issue                   9
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              8370
_journal_paper_doi               10.1021/acssuschemeng.7b02140
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C38 H36 N2 O7'
_chemical_formula_weight         632.69
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.204(3)
_cell_angle_beta                 93.969(3)
_cell_angle_gamma                112.787(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2185(3)
_cell_length_b                   13.1576(4)
_cell_length_c                   13.4400(5)
_cell_measurement_reflns_used    11291
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4650
_cell_measurement_theta_min      3.2040
_cell_volume                     1653.87(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29405
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         5816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0421
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.5306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                5054
_reflns_number_total             5816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sc7b02140_si_002.cif
_cod_data_source_block           '__2b1.OEt2'
_cod_original_cell_volume        1653.86(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4517020