Two Routes to 4-Fluorobenzisoxazol-3-one in the Synthesis of a 5-HT4Partial Agonist
Widlicka, Daniel W.; Murray, John C.; Coffman, Karen J.; Xiao, Chunguang; Brodney, Michael A.; Rainville, Joseph P.; Samas, Brian; Organic Process Research & Development 20 (2016) 233–; doi:10.1021/acs.oprd.5b00389

data_1542352
_publ_section_title
;
 Two Routes to 4-Fluorobenzisoxazol-3-one in the Synthesis of a
 5-HT4Partial Agonist
;
_journal_issue                   2
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              233
_journal_paper_doi               10.1021/acs.oprd.5b00389
_journal_volume                  20
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C52 H72 N4 O19'
_chemical_formula_weight         1057.13
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                66.7200(10)
_cell_angle_beta                 86.9500(10)
_cell_angle_gamma                71.5480(10)
_cell_formula_units_Z            2
_cell_length_a                   11.4197(2)
_cell_length_b                   15.8645(3)
_cell_length_c                   16.2611(4)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.64
_cell_measurement_theta_min      2.97
_cell_volume                     2558.26(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.8780
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'D8 QUEST diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28493
_diffrn_reflns_point_group_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.475
_diffrn_reflns_theta_min         2.968
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8780
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
; 
 Flack x determined using 4369 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.16(7)
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1415
_refine_ls_number_reflns         13908
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.8377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.535
_reflns_Friedel_fraction_max     0.526
_reflns_number_gt                13180
_reflns_number_total             13908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op5b00389_si_001.cif
_cod_data_source_block           z629_brian_p1
_cod_depositor_comments          'Adding full bibliography for 1542352.cif.'
_cod_database_code               1542352
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.873
_shelx_res_checksum              60649
_shelx_hkl_checksum              3572