#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024156.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024156
loop_
_publ_author_name
'Konstantin Yu. Koltunov'
'G.K. Surya Prakash'
'Golam Rasul'
'George A. Olah'
_publ_contact_author_address
;Boreskov Institute of Catalysis, Pr. Akademika Lavrentieva, 5, 
Novosibirsk, 630090, Russia

;
_publ_contact_author_email       koltunov@catalysis.ru
_publ_contact_author_fax         7(383)3308056
_publ_contact_author_name        'Konstantin Yu. Koltunov'
_publ_contact_author_phone       7(383)3397296
_publ_section_title
;
 Superacidic Activation of Quinoline and Isoquinoline; Their
 Reactions with Cyclohexane and Benzene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7394
_journal_page_last               7397
_journal_paper_doi               10.1021/jo070875x
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_compound_source        'firstly synthesized '
_chemical_formula_moiety         'C21 H20 N 1+, Cl 1-'
_chemical_formula_sum            'C21 H20 Cl N'
_chemical_formula_weight         321.83
_chemical_name_common
'trans 5,6,7,8-tetrahydro-6,8-diphenylisoquinoline hydrochloride'
_chemical_name_systematic
'trans 5,6,7,8-tetrahydro-6,8-diphenylisoquinoline hydrochloride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.490(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.549(2)
_cell_length_b                   8.8710(10)
_cell_length_c                   15.167(3)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.18
_cell_measurement_theta_min      2.68
_cell_volume                     1720.5(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.1250
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12021
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.68
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method 'from suturated toluene solution'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.797
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.797
_refine_ls_R_factor_all          0.1734
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1442
_reflns_number_total             3507
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo070875x-File003.cif
_cod_data_source_block           k2
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.05215(6) 1.47894(7) 0.33680(6) 0.0589(3) Uani 1 1 d . . .
N1 N 0.06584(19) 1.2170(3) 0.4675(2) 0.0615(8) Uani 1 1 d . . .
H1 H 0.0332 1.2992 0.4405 0.074 Uiso 1 1 calc R . .
C1 C 0.0897(3) 1.1871(3) 0.5618(3) 0.0636(10) Uani 1 1 d . . .
H1A H 0.0714 1.2543 0.5979 0.076 Uiso 1 1 calc R . .
C2 C 0.1413(2) 1.0570(3) 0.6052(2) 0.0557(9) Uani 1 1 d . . .
H2 H 0.1566 1.0346 0.6707 0.067 Uiso 1 1 calc R . .
C3 C 0.1718(2) 0.9559(3) 0.5523(2) 0.0429(7) Uani 1 1 d . . .
C4 C 0.2316(2) 0.8161(3) 0.6030(2) 0.0503(8) Uani 1 1 d . . .
H4A H 0.1845 0.7443 0.6089 0.060 Uiso 1 1 calc R . .
H4B H 0.2854 0.8414 0.6702 0.060 Uiso 1 1 calc R . .
C5 C 0.2823(2) 0.7434(3) 0.5460(2) 0.0404(7) Uani 1 1 d . . .
H5 H 0.3371 0.8122 0.5506 0.048 Uiso 1 1 calc R . .
C6 C 0.2022(2) 0.7315(3) 0.4359(2) 0.0482(8) Uani 1 1 d . . .
H6A H 0.1413 0.6776 0.4293 0.058 Uiso 1 1 calc R . .
H6B H 0.2317 0.6745 0.4008 0.058 Uiso 1 1 calc R . .
C7 C 0.1690(2) 0.8880(3) 0.3876(2) 0.0466(8) Uani 1 1 d . . .
H7 H 0.1047 0.8749 0.3239 0.056 Uiso 1 1 calc R . .
C8 C 0.1432(2) 0.9901(3) 0.4528(2) 0.0419(7) Uani 1 1 d . . .
C9 C 0.0906(2) 1.1244(3) 0.4141(2) 0.0544(8) Uani 1 1 d . . .
H9 H 0.0722 1.1501 0.3483 0.065 Uiso 1 1 calc R . .
C51 C 0.3339(2) 0.5919(3) 0.5869(2) 0.0416(7) Uani 1 1 d . . .
C52 C 0.2905(2) 0.4844(3) 0.6217(2) 0.0533(8) Uani 1 1 d . . .
H52 H 0.2285 0.5053 0.6230 0.064 Uiso 1 1 calc R . .
C53 C 0.3383(3) 0.3462(3) 0.6546(2) 0.0607(9) Uani 1 1 d . . .
H53 H 0.3088 0.2762 0.6793 0.073 Uiso 1 1 calc R . .
C54 C 0.4277(3) 0.3104(3) 0.6515(2) 0.0574(9) Uani 1 1 d . . .
H54 H 0.4581 0.2159 0.6723 0.069 Uiso 1 1 calc R . .
C55 C 0.4723(3) 0.4148(4) 0.6174(3) 0.0721(10) Uani 1 1 d . . .
H55 H 0.5334 0.3920 0.6149 0.086 Uiso 1 1 calc R . .
C56 C 0.4259(3) 0.5547(3) 0.5867(3) 0.0652(10) Uani 1 1 d . . .
H56 H 0.4578 0.6261 0.5653 0.078 Uiso 1 1 calc R . .
C71 C 0.2513(2) 0.9534(3) 0.3638(2) 0.0454(7) Uani 1 1 d . . .
C72 C 0.2571(3) 0.9012(3) 0.2802(3) 0.0651(10) Uani 1 1 d . . .
H72 H 0.2077 0.8327 0.2372 0.078 Uiso 1 1 calc R . .
C73 C 0.3363(3) 0.9505(4) 0.2599(3) 0.0737(11) Uani 1 1 d . . .
H73 H 0.3386 0.9159 0.2031 0.088 Uiso 1 1 calc R . .
C74 C 0.4101(3) 1.0491(4) 0.3232(3) 0.0748(11) Uani 1 1 d . . .
H74 H 0.4634 1.0812 0.3104 0.090 Uiso 1 1 calc R . .
C75 C 0.4049(3) 1.1004(4) 0.4054(3) 0.0708(10) Uani 1 1 d . . .
H75 H 0.4553 1.1678 0.4486 0.085 Uiso 1 1 calc R . .
C76 C 0.3265(3) 1.0544(3) 0.4258(2) 0.0561(9) Uani 1 1 d . . .
H76 H 0.3243 1.0918 0.4820 0.067 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 122.0(3) . . ?
C9 N1 H1 119.0 . . ?
C1 N1 H1 119.0 . . ?
N1 C1 C2 119.4(3) . . ?
N1 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C8 C3 C2 117.8(3) . . ?
C8 C3 C4 122.4(2) . . ?
C2 C3 C4 119.8(3) . . ?
C3 C4 C5 112.2(2) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C51 111.0(2) . . ?
C6 C5 C4 109.2(2) . . ?
C51 C5 C4 115.0(2) . . ?
C6 C5 H5 107.1 . . ?
C51 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C5 C6 C7 111.3(2) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C71 113.3(2) . . ?
C8 C7 C6 110.5(2) . . ?
C71 C7 C6 110.7(2) . . ?
C8 C7 H7 107.4 . . ?
C71 C7 H7 107.4 . . ?
C6 C7 H7 107.4 . . ?
C3 C8 C9 117.7(3) . . ?
C3 C8 C7 122.5(2) . . ?
C9 C8 C7 119.8(3) . . ?
N1 C9 C8 122.2(3) . . ?
N1 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C52 C51 C56 117.2(3) . . ?
C52 C51 C5 122.7(3) . . ?
C56 C51 C5 120.1(2) . . ?
C53 C52 C51 120.6(3) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C54 C53 C52 121.3(3) . . ?
C54 C53 H53 119.3 . . ?
C52 C53 H53 119.3 . . ?
C53 C54 C55 119.2(3) . . ?
C53 C54 H54 120.4 . . ?
C55 C54 H54 120.4 . . ?
C54 C55 C56 119.5(3) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C55 C56 C51 122.1(3) . . ?
C55 C56 H56 118.9 . . ?
C51 C56 H56 118.9 . . ?
C76 C71 C72 117.7(3) . . ?
C76 C71 C7 122.9(3) . . ?
C72 C71 C7 119.2(3) . . ?
C71 C72 C73 120.9(3) . . ?
C71 C72 H72 119.6 . . ?
C73 C72 H72 119.6 . . ?
C74 C73 C72 120.0(3) . . ?
C74 C73 H73 120.0 . . ?
C72 C73 H73 120.0 . . ?
C75 C74 C73 119.4(4) . . ?
C75 C74 H74 120.3 . . ?
C73 C74 H74 120.3 . . ?
C74 C75 C76 121.3(4) . . ?
C74 C75 H75 119.4 . . ?
C76 C75 H75 119.4 . . ?
C71 C76 C75 120.8(3) . . ?
C71 C76 H76 119.6 . . ?
C75 C76 H76 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.320(4) . ?
N1 C1 1.327(4) . ?
N1 H1 0.8600 . ?
C1 C2 1.363(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.408(4) . ?
C2 H2 0.9300 . ?
C3 C8 1.394(4) . ?
C3 C4 1.499(3) . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(4) . ?
C5 C51 1.520(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.536(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.513(4) . ?
C7 C71 1.521(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.386(4) . ?
C9 H9 0.9300 . ?
C51 C52 1.380(3) . ?
C51 C56 1.380(4) . ?
C52 C53 1.380(4) . ?
C52 H52 0.9300 . ?
C53 C54 1.362(4) . ?
C53 H53 0.9300 . ?
C54 C55 1.365(4) . ?
C54 H54 0.9300 . ?
C55 C56 1.383(4) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C71 C76 1.380(4) . ?
C71 C72 1.389(4) . ?
C72 C73 1.397(4) . ?
C72 H72 0.9300 . ?
C73 C74 1.363(5) . ?
C73 H73 0.9300 . ?
C74 C75 1.362(4) . ?
C74 H74 0.9300 . ?
C75 C76 1.379(4) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.86 2.17 3.005(3) 164.8 .
