#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230369.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_2230369
loop_
_publ_author_name
'Ma, Yanni'
'Sun, Yifang'
'Zheng, Feng'
'Sun, Wenwen'
'Zhou, Le'
_publ_section_title
;
 2-(2-Iodophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
;
_journal_coeditor_code           IS2698
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1484
_journal_paper_doi               10.1107/S1600536811015212
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 I N2'
_chemical_formula_moiety         'C16 H13 I N2'
_chemical_formula_sum            'C16 H13 I N2'
_chemical_formula_weight         360.18
_chemical_name_systematic
;
2-(2-Iodophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 107.6620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7607(12)
_cell_length_b                   8.4473(9)
_cell_length_c                   15.2601(15)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.61
_cell_volume                     1444.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10311
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  0.5980
_exptl_absorpt_correction_T_min  0.4578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.508
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0558P)²+2.5461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                2359
_reflns_number_total             2689
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2698.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230369
_cod_database_fobs_code          2230369
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_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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1617(4) 1.1100(5) 0.0837(3) 0.0552(10) Uani d . 1 1 . .
C C2 0.0577(4) 1.1981(7) 0.0437(5) 0.0757(15) Uani d . 1 1 . .
H H2 0.0056 1.2177 0.0778 0.091 Uiso calc R 1 1 . .
C C3 0.0307(5) 1.2559(7) -0.0439(5) 0.0821(17) Uani d . 1 1 . .
H H3 -0.0380 1.3159 -0.0682 0.098 Uiso calc R 1 1 . .
C C4 0.1052(5) 1.2253(7) -0.0962(4) 0.0785(15) Uani d . 1 1 . .
H H4 0.0867 1.2636 -0.1560 0.094 Uiso calc R 1 1 . .
C C5 0.2082(4) 1.1369(6) -0.0589(3) 0.0612(12) Uani d . 1 1 . .
H H5 0.2594 1.1170 -0.0936 0.073 Uiso calc R 1 1 . .
C C6 0.2349(4) 1.0783(5) 0.0296(3) 0.0470(9) Uani d . 1 1 . .
C C7 0.3478(4) 0.9792(5) 0.0678(3) 0.0412(8) Uani d . 1 1 . .
H H7 0.3501 0.9004 0.0213 0.049 Uiso calc R 1 1 . .
C C8 0.3220(4) 1.0020(6) 0.2187(3) 0.0535(10) Uani d . 1 1 . .
H H8A 0.3721 1.0956 0.2282 0.064 Uiso calc R 1 1 . .
H H8B 0.3359 0.9488 0.2774 0.064 Uiso calc R 1 1 . .
C C9 0.1920(5) 1.0483(6) 0.1804(4) 0.0655(13) Uani d . 1 1 . .
H H9A 0.1426 0.9568 0.1815 0.079 Uiso calc R 1 1 . .
H H9B 0.1740 1.1291 0.2194 0.079 Uiso calc R 1 1 . .
C C10 0.4559(4) 1.0835(5) 0.0839(3) 0.0457(9) Uani d . 1 1 . .
C C11 0.4559(3) 0.7998(4) 0.1851(3) 0.0417(8) Uani d . 1 1 . .
C C12 0.4616(4) 0.6511(5) 0.1462(3) 0.0440(8) Uani d . 1 1 . .
C C13 0.5645(5) 0.5622(5) 0.1734(4) 0.0588(11) Uani d . 1 1 . .
H H13 0.5677 0.4651 0.1454 0.071 Uiso calc R 1 1 . .
C C14 0.6628(4) 0.6160(6) 0.2419(3) 0.0622(12) Uani d . 1 1 . .
H H14 0.7324 0.5559 0.2596 0.075 Uiso calc R 1 1 . .
C C15 0.6579(4) 0.7576(6) 0.2839(3) 0.0615(11) Uani d . 1 1 . .
H H15 0.7230 0.7923 0.3317 0.074 Uiso calc R 1 1 . .
C C16 0.5558(4) 0.8495(5) 0.2549(3) 0.0531(10) Uani d . 1 1 . .
H H16 0.5539 0.9469 0.2829 0.064 Uiso calc R 1 1 . .
I I1 0.31094(3) 0.55223(3) 0.05008(2) 0.05981(15) Uani d . 1 1 . .
N N1 0.3511(3) 0.8951(4) 0.1520(2) 0.0425(7) Uani d . 1 1 . .
N N2 0.5385(4) 1.1593(5) 0.0987(3) 0.0632(10) Uani d . 1 1 . .
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'
I I -0.4742 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 117.4(5) ?
C6 C1 C9 . . 120.8(4) ?
C2 C1 C9 . . 121.7(4) ?
C3 C2 C1 . . 121.8(5) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
C2 C3 C4 . . 120.0(5) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.5(5) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 120.3(5) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 121.0(4) ?
C5 C6 C7 . . 118.8(4) ?
C1 C6 C7 . . 120.2(4) ?
N1 C7 C10 . . 110.3(3) ?
N1 C7 C6 . . 113.0(3) ?
C10 C7 C6 . . 109.6(3) ?
N1 C7 H7 . . 107.9 ?
C10 C7 H7 . . 107.9 ?
C6 C7 H7 . . 107.9 ?
N1 C8 C9 . . 108.0(4) ?
N1 C8 H8A . . 110.1 ?
C9 C8 H8A . . 110.1 ?
N1 C8 H8B . . 110.1 ?
C9 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
C1 C9 C8 . . 112.3(4) ?
C1 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C1 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
N2 C10 C7 . . 177.7(5) ?
C16 C11 C12 . . 117.3(4) ?
C16 C11 N1 . . 122.6(3) ?
C12 C11 N1 . . 120.2(3) ?
C13 C12 C11 . . 120.8(4) ?
C13 C12 I1 . . 118.1(3) ?
C11 C12 I1 . . 120.9(3) ?
C12 C13 C14 . . 120.5(4) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.9(4) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 119.8(4) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C11 . . 121.6(4) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
C11 N1 C7 . . 112.0(3) ?
C11 N1 C8 . . 117.1(3) ?
C7 N1 C8 . . 111.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.387(6) ?
C1 C2 . 1.403(7) ?
C1 C9 . 1.503(7) ?
C2 C3 . 1.368(9) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.390(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.528(6) ?
C7 N1 . 1.458(5) ?
C7 C10 . 1.505(6) ?
C7 H7 . 0.9800 ?
C8 N1 . 1.477(5) ?
C8 C9 . 1.513(7) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N2 . 1.128(5) ?
C11 C16 . 1.390(6) ?
C11 C12 . 1.400(5) ?
C11 N1 . 1.430(5) ?
C12 C13 . 1.377(6) ?
C12 I1 . 2.100(4) ?
C13 C14 . 1.380(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.367(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.386(7) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7 N2 3_675 0.98 2.60 3.418(5) 141
C7 H7 I1 . 0.98 3.03 3.633(4) 121
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -2.3(8) ?
C9 C1 C2 C3 . . . . 179.2(5) ?
C1 C2 C3 C4 . . . . 1.4(9) ?
C2 C3 C4 C5 . . . . -0.6(9) ?
C3 C4 C5 C6 . . . . 0.8(8) ?
C4 C5 C6 C1 . . . . -1.8(7) ?
C4 C5 C6 C7 . . . . 179.0(4) ?
C2 C1 C6 C5 . . . . 2.5(7) ?
C9 C1 C6 C5 . . . . -179.0(4) ?
C2 C1 C6 C7 . . . . -178.3(4) ?
C9 C1 C6 C7 . . . . 0.2(6) ?
C5 C6 C7 N1 . . . . -166.6(4) ?
C1 C6 C7 N1 . . . . 14.2(5) ?
C5 C6 C7 C10 . . . . 70.0(5) ?
C1 C6 C7 C10 . . . . -109.2(4) ?
C6 C1 C9 C8 . . . . 19.0(6) ?
C2 C1 C9 C8 . . . . -162.6(4) ?
N1 C8 C9 C1 . . . . -51.5(5) ?
C16 C11 C12 C13 . . . . -3.1(6) ?
N1 C11 C12 C13 . . . . 176.0(4) ?
C16 C11 C12 I1 . . . . 173.5(3) ?
N1 C11 C12 I1 . . . . -7.4(5) ?
C11 C12 C13 C14 . . . . 2.1(7) ?
I1 C12 C13 C14 . . . . -174.6(4) ?
C12 C13 C14 C15 . . . . 0.7(7) ?
C13 C14 C15 C16 . . . . -2.5(7) ?
C14 C15 C16 C11 . . . . 1.5(7) ?
C12 C11 C16 C15 . . . . 1.3(6) ?
N1 C11 C16 C15 . . . . -177.8(4) ?
C16 C11 N1 C7 . . . . 98.6(4) ?
C12 C11 N1 C7 . . . . -80.4(4) ?
C16 C11 N1 C8 . . . . -31.4(5) ?
C12 C11 N1 C8 . . . . 149.5(4) ?
C10 C7 N1 C11 . . . . -58.6(4) ?
C6 C7 N1 C11 . . . . 178.4(3) ?
C10 C7 N1 C8 . . . . 74.5(4) ?
C6 C7 N1 C8 . . . . -48.5(4) ?
C9 C8 N1 C11 . . . . -161.5(4) ?
C9 C8 N1 C7 . . . . 68.1(4) ?
