Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement.
Hossian, Asik; Jana, Ranjan; Organic & biomolecular chemistry 14 (2016) 9768–9779; doi:10.1039/c6ob01758d

data_7155280
_publ_section_title
;
 Carboxyl radical-assisted 1,5-aryl migration through Smiles
 rearrangement.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9768
_journal_page_last               9779
_journal_paper_doi               10.1039/c6ob01758d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C13 H9 N O5'
_chemical_formula_sum            'C13 H9 N O5'
_chemical_formula_weight         259.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-12 deposited with the CCDC.
2016-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.069(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7430(9)
_cell_length_b                   16.6008(14)
_cell_length_c                   6.9203(7)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.9
_cell_volume                     1215.17(19)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II (BRUKER,2010)'
_computing_data_reduction        'SAINT (BRUKER,2000)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11534
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         1.925
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.8789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.021(3)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0596P)^2^+0.1778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             2674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01758d2.cif
_cod_data_source_block           rj_ah421_0m
_cod_depositor_comments          'Adding full bibliography for 7155280.cif.'
_cod_database_code               7155280
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              19439
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'