Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives.
Yu, Liu-Zhu; Hu, Xu-Bo; Xu, Qin; Shi, Min; Chemical communications (Cambridge, England) 52 (2016) 2701–2704; doi:10.1039/c5cc09218c

data_7118420
_publ_section_title
;
 Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered
 alkylidenecyclopropanes: facile synthesis of furoquinoline and
 thienoquinoline derivatives.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2701
_journal_page_last               2704
_journal_paper_doi               10.1039/c5cc09218c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C17 H12 Cl N O'
_chemical_formula_weight         281.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-08 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                78.278(3)
_cell_angle_beta                 83.751(3)
_cell_angle_gamma                64.580(3)
_cell_formula_units_Z            4
_cell_length_a                   8.2770(12)
_cell_length_b                   8.8610(13)
_cell_length_c                   20.949(3)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.012
_cell_measurement_theta_min      5.451
_cell_volume                     1358.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.986
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0572P)^2^+0.2393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3796
_reflns_number_total             5322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09218c2.cif
_cod_data_source_block           cd15160
_cod_depositor_comments
'Adding full bibliography for 7118419--7118421.cif.'
_cod_original_cell_volume        1358.4(4)
_cod_database_code               7118420
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2013-4
_shelx_res_checksum              5341