Synthesis and X-ray crystallographic analysis of free base and hexafluorophosphate salts of 3,4-dihydroisoquinolines from the Bischler–Napieralski reaction
Puerto Galvis, Carlos E.; Granados, Cristian C.; Kouznetsov, Vladimir V.; Macías, Mario A.; New Journal of Chemistry 45 (2021) 1565–1572; doi:10.1039/D0NJ05235C

data_7060153
_publ_section_title
;
 Synthesis and X-ray crystallographic analysis of free base and
 hexafluorophosphate salts of 3,4-dihydroisoquinolines from the
 Bischler--Napieralski reaction
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1565
_journal_page_last               1572
_journal_paper_doi               10.1039/D0NJ05235C
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H18 N O, F6 P'
_chemical_formula_sum            'C18 H18 F6 N O P'
_chemical_formula_weight         409.30
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.8217(9)
_cell_length_b                   9.8217(9)
_cell_length_c                   32.600(5)
_cell_measurement_reflns_used    9257
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.8130
_cell_measurement_theta_min      4.2520
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            32276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.090
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_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36868
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.7154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1866
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3153
_reflns_number_total             4016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05235c2.cif
_cod_data_source_block           shelxs
_cod_depositor_comments
'Adding full bibliography for 7060153--7060154.cif.'
_cod_original_cell_volume        2723.4(7)
_cod_database_code               7060153
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              35802
_shelx_hkl_checksum              99144