#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/66/2016617.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_2016617
loop_
_publ_author_name
'Fallahpour, Reza-Ali'
'Linden, Anthony'
_publ_section_title
;
 4'-Iodo-2,2':6',2''-terpyridine
;
_journal_coeditor_code           SK3224
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o283
_journal_page_last               o285
_journal_paper_doi               10.1107/S0108270108010354
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H10 I N3'
_chemical_formula_moiety         'C15 H10 I N3'
_chemical_formula_sum            'C15 H10 I N3'
_chemical_formula_weight         359.17
_chemical_name_systematic
;
4'-iodo-2,2':6',2''-terpyridine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4518(2)
_cell_length_b                   17.2432(3)
_cell_length_c                   10.0691(2)
_cell_measurement_reflns_used    15271
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1293.81(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19500
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_T_max  0.544
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.788
_refine_diff_density_min         -1.867
_refine_ls_abs_structure_details
'Flack & Bernardinelli (1999, 2000), 1738 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0449P)²+5.4428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                3524
_reflns_number_total             3713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3224.cif
_cod_data_source_block           I
_cod_database_code               2016617
_cod_database_fobs_code          2016617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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 0.34425(3) 0.559690(13) 0.39444(6) 0.01972(9) Uani d . 1
N N1 0.4181(5) 0.7922(2) 0.6643(4) 0.0135(6) Uani d . 1
N N8 0.3567(6) 0.8850(3) 0.3472(5) 0.0174(10) Uani d . 1
N N14 0.5254(5) 0.6454(2) 0.9086(5) 0.0198(8) Uani d . 1
C C2 0.3750(6) 0.7977(3) 0.5350(4) 0.0142(8) Uani d . 1
C C3 0.3506(6) 0.7337(3) 0.4524(5) 0.0171(8) Uani d . 1
H H3 0.3195 0.7396 0.3615 0.021 Uiso calc R 1
C C4 0.3740(6) 0.6607(2) 0.5088(4) 0.0135(7) Uani d . 1
C C5 0.4212(6) 0.6536(2) 0.6412(4) 0.0156(8) Uani d . 1
H H5 0.4404 0.6041 0.6801 0.019 Uiso calc R 1
C C6 0.4397(6) 0.7210(2) 0.7153(4) 0.0140(7) Uani d . 1
C C7 0.3595(7) 0.8778(4) 0.4813(5) 0.0170(11) Uani d . 1
C C9 0.3459(6) 0.9560(3) 0.2967(6) 0.0208(10) Uani d . 1
H H9 0.3452 0.9612 0.2028 0.025 Uiso calc R 1
C C10 0.3356(6) 1.0230(3) 0.3725(5) 0.0197(12) Uani d . 1
H H10 0.3314 1.0726 0.3315 0.024 Uiso calc R 1
C C11 0.3315(7) 1.0156(3) 0.5119(5) 0.0213(9) Uani d . 1
H H11 0.3213 1.0600 0.5674 0.026 Uiso calc R 1
C C12 0.3426(7) 0.9417(3) 0.5658(6) 0.0217(10) Uani d . 1
H H12 0.3389 0.9346 0.6593 0.026 Uiso calc R 1
C C13 0.4838(6) 0.7162(2) 0.8607(4) 0.0142(8) Uani d . 1
C C15 0.5594(7) 0.6399(3) 1.0357(5) 0.0231(10) Uani d . 1
H H15 0.5885 0.5902 1.0702 0.028 Uiso calc R 1
C C16 0.5559(7) 0.7025(3) 1.1246(4) 0.0206(9) Uani d . 1
H H16 0.5833 0.6954 1.2159 0.025 Uiso calc R 1
C C17 0.5116(7) 0.7748(3) 1.0754(5) 0.0211(9) Uani d . 1
H H17 0.5068 0.8187 1.1324 0.025 Uiso calc R 1
C C18 0.4738(6) 0.7819(3) 0.9398(5) 0.0188(8) Uani d . 1
H H18 0.4421 0.8307 0.9027 0.023 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 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
I I -0.4742 1.8119
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
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
C6 N1 C2 117.7(4)
C9 N8 C7 117.8(6)
C15 N14 C13 117.3(4)
N1 C2 C3 123.6(4)
N1 C2 C7 115.8(4)
C3 C2 C7 120.5(4)
C4 C3 C2 117.1(4)
C4 C3 H3 121.4
C2 C3 H3 121.4
C5 C4 C3 120.3(4)
C5 C4 I1 118.8(3)
C3 C4 I1 120.9(3)
C4 C5 C6 117.9(4)
C4 C5 H5 121.0
C6 C5 H5 121.0
N1 C6 C5 123.3(4)
N1 C6 C13 116.8(4)
C5 C6 C13 119.9(4)
N8 C7 C12 122.2(6)
N8 C7 C2 116.6(6)
C12 C7 C2 121.2(5)
N8 C9 C10 124.1(5)
N8 C9 H9 117.9
C10 C9 H9 117.9
C9 C10 C11 118.3(4)
C9 C10 H10 120.9
C11 C10 H10 120.9
C12 C11 C10 118.1(5)
C12 C11 H11 121.0
C10 C11 H11 121.0
C11 C12 C7 119.4(5)
C11 C12 H12 120.3
C7 C12 H12 120.3
N14 C13 C18 123.2(4)
N14 C13 C6 116.7(4)
C18 C13 C6 120.1(4)
N14 C15 C16 124.5(5)
N14 C15 H15 117.8
C16 C15 H15 117.8
C17 C16 C15 118.0(4)
C17 C16 H16 121.0
C15 C16 H16 121.0
C16 C17 C18 118.5(4)
C16 C17 H17 120.8
C18 C17 H17 120.8
C13 C18 C17 118.5(4)
C13 C18 H18 120.8
C17 C18 H18 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C4 2.100(4)
N1 C6 1.340(5)
N1 C2 1.344(6)
N8 C9 1.328(7)
N8 C7 1.356(7)
N14 C15 1.308(7)
N14 C13 1.349(5)
C2 C3 1.393(6)
C2 C7 1.487(7)
C3 C4 1.391(6)
C3 H3 0.9500
C4 C5 1.384(6)
C5 C6 1.388(6)
C5 H5 0.9500
C6 C13 1.503(5)
C7 C12 1.398(8)
C9 C10 1.386(8)
C9 H9 0.9500
C10 C11 1.410(7)
C10 H10 0.9500
C11 C12 1.388(7)
C11 H11 0.9500
C12 H12 0.9500
C13 C18 1.387(6)
C15 C16 1.402(7)
C15 H15 0.9500
C16 C17 1.382(7)
C16 H16 0.9500
C17 C18 1.400(6)
C17 H17 0.9500
C18 H18 0.9500
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
_geom_hbond_publ_flag
C15 H15 I1 2_665 0.95 3.17 3.793(5) 125 yes
C17 H17 N8 1_556 0.95 2.69 3.526(6) 147 yes
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
C6 N1 C2 C3 0.5(6)
C6 N1 C2 C7 -177.6(4)
N1 C2 C3 C4 -0.4(7)
C7 C2 C3 C4 177.6(4)
C2 C3 C4 C5 -0.7(6)
C2 C3 C4 I1 -179.3(3)
C3 C4 C5 C6 1.6(6)
I1 C4 C5 C6 -179.8(3)
C2 N1 C6 C5 0.5(6)
C2 N1 C6 C13 -178.7(4)
C4 C5 C6 N1 -1.5(7)
C4 C5 C6 C13 177.6(4)
C9 N8 C7 C12 3.2(9)
C9 N8 C7 C2 -178.9(4)
N1 C2 C7 N8 165.6(5)
C3 C2 C7 N8 -12.6(7)
N1 C2 C7 C12 -16.6(7)
C3 C2 C7 C12 165.3(5)
C7 N8 C9 C10 -0.7(8)
N8 C9 C10 C11 -1.8(7)
C9 C10 C11 C12 1.6(7)
C10 C11 C12 C7 0.7(7)
N8 C7 C12 C11 -3.3(8)
C2 C7 C12 C11 179.0(5)
C15 N14 C13 C18 -0.7(7)
C15 N14 C13 C6 -178.2(4)
N1 C6 C13 N14 -172.7(4)
C5 C6 C13 N14 8.1(6)
N1 C6 C13 C18 9.7(6)
C5 C6 C13 C18 -169.5(4)
C13 N14 C15 C16 -0.2(8)
N14 C15 C16 C17 0.8(8)
C15 C16 C17 C18 -0.5(8)
N14 C13 C18 C17 1.0(7)
C6 C13 C18 C17 178.5(4)
C16 C17 C18 C13 -0.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8793792
