Heterocycle-Heterocycle Strategies: (2-Nitrophenyl)isoxazole Precursors to 4-Aminoquinolines, 1H-Indoles, and Quinolin-4(1H)-ones.
Coffman, Keith C.; Palazzo, Teresa A.; Hartley, Timothy P.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.; Organic letters 15 (2013) 2062–2065; doi:10.1021/ol400787y

data_1511965
_publ_section_title
;
 Heterocycle-Heterocycle Strategies: (2-Nitrophenyl)isoxazole Precursors
 to 4-Aminoquinolines, 1H-Indoles, and Quinolin-4(1H)-ones.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2062
_journal_page_last               2065
_journal_paper_doi               10.1021/ol400787y
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 106.3440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7298(8)
_cell_length_b                   7.4458(3)
_cell_length_c                   14.6820(5)
_cell_measurement_reflns_used    9174
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      6.28
_cell_volume                     2384.39(15)
_computing_cell_refinement       'SAINT (8.18C) (Bruker, 2012)'
_computing_data_collection       'Apex2 (2012.2-0) (Bruker, 2012)'
_computing_data_reduction        'SAINT (8.18C) (Bruker, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6343
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.373
_diffrn_reflns_theta_min         6.281
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.8649
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       Plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.386
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0502P)^2^+1.5504P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2213
_reflns_number_total             2248
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol400787y_si_003.cif
_cod_data_source_block           KC1FMI
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1511965
_shelx_estimated_absorpt_t_min   0.757
_shelx_estimated_absorpt_t_max   0.951
_shelxl_version_number           2012-6
_shelx_res_checksum              55405
_shelx_hkl_checksum              49500