A Concise Synthesis of Quinolinium, and Biquinolinium Salts and Biquinolines from Benzylic Azides and Alkenes Promoted by Copper(II) Species
Chen, Wei-Chen; Parthasarathy, Gandeepan; Tsai, Chia-Hung; Luo, Ching-Zong; Rajamalli, Pachaiyappan; Cheng, Chien Hong; RSC Adv.  (2016) –; doi:10.1039/C6RA11840B

data_7225658
_publ_section_title
;
 A Concise Synthesis of Quinolinium, and Biquinolinium Salts and
 Biquinolines from Benzylic Azides and Alkenes Promoted by Copper(II)
 Species
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA11840B
_journal_year                    2016
_chemical_formula_sum            'C20 H20 B F4 N'
_chemical_formula_weight         361.18
_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-2014/6
_audit_update_record
;
2015-11-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                78.224(2)
_cell_angle_beta                 65.746(2)
_cell_angle_gamma                73.570(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0489(7)
_cell_length_b                   10.2453(9)
_cell_length_c                   10.8052(9)
_cell_measurement_reflns_used    1780
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.0267
_cell_measurement_theta_min      2.7908
_cell_volume                     871.59(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_min         2.078
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.012(9)
_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   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     255
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1795P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2507
_refine_ls_wR_factor_ref         0.2990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1342
_reflns_number_total             3512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra11840b2.cif
_cod_data_source_block           mo_150929_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7225658
_shelxl_version_number           2014/6
_shelx_res_checksum              59471