Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.
Evoniuk, Christopher J.; Gomes, Gabriel Dos Passos; Ly, Michelle; White, Frankie D.; Alabugin, Igor V.; The Journal of organic chemistry 82 (2017) 4265–4278; doi:10.1021/acs.joc.7b00262

data_4037477
_publ_section_title
;
 Coupling Radical Homoallylic Expansions with C-C Fragmentations for the
 Synthesis of Heteroaromatics: Quinolines from Reactions of
 o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4265
_journal_page_last               4278
_journal_paper_doi               10.1021/acs.joc.7b00262
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         '2(C19 H12 Br N)'
_chemical_formula_sum            'C38 H24 Br2 N2'
_chemical_formula_weight         668.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                103.756(2)
_cell_angle_beta                 94.792(2)
_cell_angle_gamma                109.637(2)
_cell_formula_units_Z            1
_cell_length_a                   4.0508(5)
_cell_length_b                   12.2873(15)
_cell_length_c                   15.1864(19)
_cell_measurement_reflns_used    5951
_cell_measurement_temperature    137(2)
_cell_measurement_theta_max      25.328
_cell_measurement_theta_min      2.607
_cell_volume                     680.37(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      137.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker apex II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'Imus microfocused'
_exptl_absorpt_coefficient_mu    3.012
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0795 before and 0.0411 after correction. The Ratio of minimum to maximum transmission is 0.8532. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0273P)^2^+0.4083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2310
_reflns_number_total             2477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00262_si_002.cif
_cod_data_source_block           chris_br_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'N/A' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037477
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   SCALE
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C007(H007), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D),
 C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L)
;
_olex2_submission_special_instructions 'No special instructions were received'