Development of a Continuous Flow Photoisomerization Reaction Converting Isoxazoles into Diverse Oxazole Products.
Bracken, Cormac; Baumann, Marcus; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03399

data_4037851
_publ_section_title
;
 Development of a Continuous Flow Photoisomerization Reaction Converting
 Isoxazoles into Diverse Oxazole Products.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03399
_journal_year                    2020
_chemical_formula_moiety         '2 (C17 H13 N3 O5), H2 O'
_chemical_formula_sum            'C34 H28 N6 O11'
_chemical_formula_weight         696.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.039(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0650(5)
_cell_length_b                   8.0448(2)
_cell_length_c                   21.6927(5)
_cell_measurement_reflns_used    5473
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7560
_cell_measurement_theta_min      3.7840
_cell_volume                     3213.14(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11474
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.916
_diffrn_reflns_theta_min         2.832
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0454P)^2^+2.2340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3839
_reflns_number_total             4529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03399_si_002.cif
_cod_data_source_block           bau01
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4037851
_shelxl_version_number           2014-3
_shelx_res_checksum              96743
_shelx_hkl_checksum              36463