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_4037854
_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         'C10 H9 N O3 S'
_chemical_formula_sum            'C10 H9 N O3 S'
_chemical_formula_weight         223.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.837(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.29000(9)
_cell_length_b                   16.4483(2)
_cell_length_c                   12.6312(2)
_cell_measurement_reflns_used    7999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.4600
_cell_measurement_theta_min      4.4010
_cell_volume                     1096.60(3)
_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      293(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.842
_diffrn_reflns_theta_min         4.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.580
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0750P)^2^+0.1729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2016
_reflns_number_total             2303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03399_si_002.cif
_cod_data_source_block           bau12
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037854
_shelxl_version_number           2014-3
_shelx_res_checksum              56917
_shelx_hkl_checksum              62072