Iron-catalyzed or iodine-induced intramolecular halocyclization of N-vinyl-tethered methylenecyclopropanes: facile access to halogenated 1,2-dihydroquinolines
Wang, Qiang; Jiang, Bo; Yu, Liu-Zhu; Wei, Yin; Shi, Min; Organic Chemistry Frontiers 4 (2017) 1294–; doi:10.1039/C7QO00177K

data_1553764
_publ_section_title
;
 Iron-catalyzed or iodine-induced intramolecular halocyclization of
 N-vinyl-tethered methylenecyclopropanes: facile access to halogenated
 1,2-dihydroquinolines
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1294
_journal_paper_doi               10.1039/C7QO00177K
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C25 H22 F I2 N O2 S'
_chemical_formula_weight         673.29
_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_method           SHELXL-2013
_audit_update_record
;
2017-02-24 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                82.330(2)
_cell_angle_beta                 79.359(2)
_cell_angle_gamma                79.100(2)
_cell_formula_units_Z            2
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_cell_length_b                   10.5461(13)
_cell_length_c                   13.9946(17)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      5.187
_cell_volume                     1233.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
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_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7115
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.488
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_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
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_exptl_crystal_description       prismatic
_exptl_crystal_F_000             652
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_refine_diff_density_max         0.415
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_refine_ls_extinction_coef       0.0074(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4011
_reflns_number_total             4586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00177k2.cif
_cod_data_source_block           cd17086
_cod_database_code               1553764
_shelx_estimated_absorpt_t_min   0.618
_shelx_estimated_absorpt_t_max   0.723
_shelxl_version_number           2013-4
_shelx_res_checksum              91050
_shelx_hkl_checksum              27283