#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/46/2214614.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214614
loop_
_publ_author_name
'Ben Ali, Karim'
'Chiaroni, Angèle'
'Bohe, Luis'
_publ_section_title
;(3R,4S)-2-Isopropyl-3-methyl-4-phenyl-3,4-dihydroisoquinolinium
 iodide
;
_journal_coeditor_code           DN2204
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3355
_journal_page_last               o3355
_journal_paper_doi               10.1107/S1600536807030565
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H22 N +, I -'
_chemical_formula_moiety         'C19 H22 N +, I -'
_chemical_formula_sum            'C19 H22 I N'
_chemical_formula_weight         391.28
_chemical_melting_point          457
_chemical_name_systematic
;
(3R,4S)-2-Isopropyl-3-methyl-4-phenyl-3,4-dihydroisoquinolinium iodide
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.773(4)
_cell_length_b                   9.773(4)
_cell_length_c                   32.630(12)
_cell_measurement_reflns_used    3639
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2699.0(19)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            6545
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         .553
_refine_diff_density_min         -1.013
_refine_ls_abs_structure_details 'Flack (1983), 1602 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0277P)²+2.172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2992
_reflns_number_total             3694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2204.cif
_cod_data_source_block           I
_cod_database_code               2214614
_cod_database_fobs_code          2214614
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
I I1 0.64454(5) 0.68377(4) 0.139072(16) 0.1060(2) Uani d . 1
C C1 0.7788(5) 0.4692(5) 0.20412(13) 0.0535(10) Uani d . 1
H H1 0.8142 0.5730 0.2121 0.060 Uiso calc R 1
N N2 0.8719(4) 0.4388(4) 0.18374(10) 0.0528(8) Uani d . 1
C C3 0.8106(5) 0.2778(5) 0.16614(15) 0.0599(11) Uani d . 1
H H3 0.9006 0.2622 0.1610 0.067 Uiso calc R 1
C C4 0.7003(5) 0.1521(5) 0.19702(15) 0.0606(11) Uani d . 1
H H4 0.6446 0.0516 0.1822 0.068 Uiso calc R 1
C C5 0.4251(6) 0.0766(6) 0.22239(18) 0.0740(14) Uani d . 1
H H5 0.3941 -0.0298 0.2198 0.083 Uiso calc R 1
C C6 0.3199(6) 0.1186(8) 0.23685(19) 0.0853(17) Uani d . 1
H H6 0.2183 0.0406 0.2440 0.096 Uiso calc R 1
C C7 0.3627(6) 0.2737(9) 0.24090(19) 0.0837(17) Uani d . 1
H H7 0.2898 0.3009 0.2505 0.094 Uiso calc R 1
C C8 0.5150(6) 0.3917(6) 0.23068(16) 0.0692(13) Uani d . 1
H H8 0.5454 0.4976 0.2341 0.078 Uiso calc R 1
C C9 0.6205(5) 0.3492(5) 0.21536(13) 0.0508(9) Uani d . 1
C C10 0.5777(5) 0.1908(5) 0.21141(14) 0.0543(10) Uani d . 1
C C11 0.7318(7) 0.2690(7) 0.12538(15) 0.0827(16) Uani d . 1
H H11A 0.6999 0.1688 0.1127 0.099 Uiso calc R 1
H H11B 0.8049 0.3525 0.1078 0.099 Uiso calc R 1
H H11C 0.6407 0.2800 0.1298 0.099 Uiso calc R 1
C C12 0.7885(5) 0.1284(5) 0.23205(16) 0.0582(11) Uani d . 1
C C13 0.8437(6) 0.2279(6) 0.26558(16) 0.0666(12) Uani d . 1
H H13 0.8217 0.3098 0.2678 0.075 Uiso calc R 1
C C14 0.9315(6) 0.2078(7) 0.29619(18) 0.0766(14) Uani d . 1
H H14 0.9722 0.2789 0.3179 0.086 Uiso calc R 1
C C15 0.9572(7) 0.0836(9) 0.2941(2) 0.094(2) Uani d . 1
H H15 1.0137 0.0679 0.3147 0.105 Uiso calc R 1
C C16 0.8997(7) -0.0179(8) 0.2617(3) 0.096(2) Uani d . 1
H H16 0.9167 -0.1033 0.2605 0.108 Uiso calc R 1
C C17 0.8179(6) 0.0037(6) 0.2311(2) 0.0740(14) Uani d . 1
H H17 0.7812 -0.0663 0.2091 0.083 Uiso calc R 1
C C18 1.0400(5) 0.5578(6) 0.17395(16) 0.0718(13) Uani d . 1
H H18 1.0601 0.5393 0.1456 0.080 Uiso calc R 1
C C19 1.0690(7) 0.7252(6) 0.1764(2) 0.097(2) Uani d . 1
H H19A 1.1722 0.7972 0.1659 0.116 Uiso calc R 1
H H19B 1.0622 0.7510 0.2044 0.116 Uiso calc R 1
H H19C 0.9908 0.7333 0.1604 0.116 Uiso calc R 1
C C20 1.1482(6) 0.5291(9) 0.2014(2) 0.097(2) Uani d . 1
H H20A 1.1392 0.5570 0.2291 0.116 Uiso calc R 1
H H20B 1.2554 0.5927 0.1923 0.116 Uiso calc R 1
H H20C 1.1185 0.4196 0.2003 0.116 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -.4742 1.8119 '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
N2 C1 C9 122.8(4)
N2 C1 H1 118.6
C9 C1 H1 118.6
C1 N2 C3 119.3(4)
C1 N2 C18 124.3(4)
C3 N2 C18 116.3(4)
N2 C3 C11 108.8(4)
N2 C3 C4 110.0(3)
C11 C3 C4 113.3(4)
N2 C3 H3 108.2
C11 C3 H3 108.2
C4 C3 H3 108.2
C10 C4 C12 112.9(4)
C10 C4 C3 109.4(4)
C12 C4 C3 113.0(4)
C10 C4 H4 107.1
C12 C4 H4 107.1
C3 C4 H4 107.1
C6 C5 C10 120.9(5)
C6 C5 H5 119.5
C10 C5 H5 119.5
C7 C6 C5 120.6(5)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 120.2(5)
C6 C7 H7 119.9
C8 C7 H7 119.9
C9 C8 C7 119.1(5)
C9 C8 H8 120.4
C7 C8 H8 120.4
C8 C9 C10 120.8(4)
C8 C9 C1 120.2(4)
C10 C9 C1 118.9(4)
C5 C10 C9 118.3(4)
C5 C10 C4 123.3(4)
C9 C10 C4 118.4(4)
C3 C11 H11A 109.5
C3 C11 H11B 109.5
H11A C11 H11B 109.5
C3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 117.2(5)
C13 C12 C4 122.8(4)
C17 C12 C4 120.0(5)
C12 C13 C14 121.3(5)
C12 C13 H13 119.3
C14 C13 H13 119.3
C15 C14 C13 119.5(6)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 119.7(6)
C14 C15 H15 120.2
C16 C15 H15 120.2
C17 C16 C15 121.1(5)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C12 121.0(6)
C16 C17 H17 119.5
C12 C17 H17 119.5
N2 C18 C20 109.0(4)
N2 C18 C19 111.5(4)
C20 C18 C19 113.4(5)
N2 C18 H18 107.5
C20 C18 H18 107.5
C19 C18 H18 107.5
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.276(5)
C1 C9 1.445(6)
C1 H1 0.9300
N2 C3 1.491(5)
N2 C18 1.497(5)
C3 C11 1.517(7)
C3 C4 1.537(7)
C3 H3 0.9800
C4 C10 1.501(6)
C4 C12 1.518(7)
C4 H4 0.9800
C5 C6 1.367(8)
C5 C10 1.391(6)
C5 H5 0.9300
C6 C7 1.362(8)
C6 H6 0.9300
C7 C8 1.393(8)
C7 H7 0.9300
C8 C9 1.383(6)
C8 H8 0.9300
C9 C10 1.393(6)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.381(7)
C12 C17 1.385(6)
C13 C14 1.393(7)
C13 H13 0.9300
C14 C15 1.359(8)
C14 H14 0.9300
C15 C16 1.364(9)
C15 H15 0.9300
C16 C17 1.361(9)
C16 H16 0.9300
C17 H17 0.9300
C18 C20 1.516(8)
C18 C19 1.516(8)
C18 H18 0.9800
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 N2 C3 7.8(6)
C9 C1 N2 C18 -175.7(4)
C1 N2 C3 C11 83.8(5)
C18 N2 C3 C11 -92.9(5)
C1 N2 C3 C4 -40.9(5)
C18 N2 C3 C4 142.4(4)
N2 C3 C4 C10 51.6(5)
C11 C3 C4 C10 -70.5(5)
N2 C3 C4 C12 -75.1(5)
C11 C3 C4 C12 162.8(4)
C10 C5 C6 C7 -0.1(9)
C5 C6 C7 C8 -0.7(9)
C6 C7 C8 C9 1.8(9)
C7 C8 C9 C10 -2.2(7)
C7 C8 C9 C1 179.3(5)
N2 C1 C9 C8 -168.1(5)
N2 C1 C9 C10 13.4(6)
C6 C5 C10 C9 -0.3(8)
C6 C5 C10 C4 177.4(5)
C8 C9 C10 C5 1.5(7)
C1 C9 C10 C5 179.9(4)
C8 C9 C10 C4 -176.3(4)
C1 C9 C10 C4 2.1(6)
C12 C4 C10 C5 -85.0(6)
C3 C4 C10 C5 148.2(5)
C12 C4 C10 C9 92.6(5)
C3 C4 C10 C9 -34.1(5)
C10 C4 C12 C13 -44.2(6)
C3 C4 C12 C13 80.7(5)
C10 C4 C12 C17 136.4(4)
C3 C4 C12 C17 -98.8(5)
C17 C12 C13 C14 2.9(7)
C4 C12 C13 C14 -176.6(5)
C12 C13 C14 C15 -3.2(8)
C13 C14 C15 C16 1.4(8)
C14 C15 C16 C17 0.6(9)
C15 C16 C17 C12 -0.9(9)
C13 C12 C17 C16 -0.9(7)
C4 C12 C17 C16 178.6(5)
C1 N2 C18 C20 104.5(5)
C3 N2 C18 C20 -79.0(5)
C1 N2 C18 C19 -21.5(6)
C3 N2 C18 C19 155.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184619
