#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:52:58 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246088 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311699.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_2311699
loop_
_publ_author_name
'Wijethunga, Tharanga K.'
'Đaković, Marijana'
'Desper, John'
'Aakeröy, Christer B'
_publ_section_title
;
 A new tecton with parallel halogen-bond donors: a path to supramolecular
 rectangles.
;
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              163
_journal_page_last               167
_journal_paper_doi               10.1107/S2052520616016450
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety
;
(C18 H8 I2) (C12 H12 N2)
;
_chemical_formula_sum            'C30 H20 I2 N2'
_chemical_formula_weight         662.28
_chemical_name_systematic
;
TW-10-14 1,8-di(iodoethynyl)anthracene, 1,2-bis(4-pyridyl)ethane
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                96.346(5)
_cell_angle_beta                 93.215(5)
_cell_angle_gamma                103.295(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5153(16)
_cell_length_b                   9.6261(16)
_cell_length_c                   14.368(3)
_cell_measurement_reflns_used    9607
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.45
_cell_measurement_theta_min      2.21
_cell_volume                     1268.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38542
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         32.488
_diffrn_reflns_theta_min         2.192
_exptl_absorpt_coefficient_mu    2.500
_exptl_absorpt_correction_T_max  0.721
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.484
_refine_diff_density_min         -0.845
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         8522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0254
_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)+(0.0300P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                7891
_reflns_number_total             8522
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao5017sup1.cif
_cod_data_source_block           DIEABpe
_cod_database_code               2311699
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.435
_shelx_estimated_absorpt_t_max   0.721
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
C C11 0.51557(19) -0.08715(19) 0.39395(12) 0.0216(3) Uani d 1
C C12 0.6412(2) 0.0273(2) 0.38789(12) 0.0235(3) Uani d 1
C C13 0.7757(2) 0.0183(2) 0.42377(14) 0.0281(4) Uani d 1
H H13 0.8579 0.0941 0.4195 0.034 Uiso calc 1
C C14 0.7926(2) -0.1029(2) 0.46702(15) 0.0313(4) Uani d 1
H H14 0.8859 -0.1069 0.4922 0.038 Uiso calc 1
C C15 0.6769(2) -0.2133(2) 0.47287(14) 0.0304(4) Uani d 1
H H15 0.6905 -0.2941 0.5015 0.036 Uiso calc 1
C C16 0.5348(2) -0.2100(2) 0.43662(13) 0.0251(3) Uani d 1
C C17 0.4150(2) -0.3220(2) 0.44240(14) 0.0273(4) Uani d 1
H H17 0.4282 -0.4039 0.4700 0.033 Uiso calc 1
C C18 0.2760(2) -0.31717(19) 0.40873(13) 0.0244(3) Uani d 1
C C19 0.1523(2) -0.4314(2) 0.41500(14) 0.0291(4) Uani d 1
H H19 0.1644 -0.5139 0.4422 0.035 Uiso calc 1
C C20 0.0175(2) -0.4239(2) 0.38256(15) 0.0298(4) Uani d 1
H H20 -0.0633 -0.5015 0.3867 0.036 Uiso calc 1
C C21 -0.0033(2) -0.3015(2) 0.34285(14) 0.0273(3) Uani d 1
H H21 -0.0982 -0.2979 0.3206 0.033 Uiso calc 1
C C22 0.1117(2) -0.18721(19) 0.33584(13) 0.0234(3) Uani d 1
C C23 0.25642(19) -0.19285(18) 0.36762(12) 0.0216(3) Uani d 1
C C24 0.37687(19) -0.08126(19) 0.36047(12) 0.0220(3) Uani d 1
H H24 0.3641 0.0002 0.3323 0.026 Uiso calc 1
C C31 0.6273(2) 0.1492(2) 0.34253(13) 0.0251(3) Uani d 1
C C32 0.6185(2) 0.2497(2) 0.30121(14) 0.0278(4) Uani d 1
I I1 0.61962(2) 0.41887(2) 0.22996(2) 0.02785(4) Uani d 1
C C41 0.0904(2) -0.0613(2) 0.29833(13) 0.0248(3) Uani d 1
C C42 0.0806(2) 0.0495(2) 0.26973(14) 0.0275(3) Uani d 1
I I2 0.07998(2) 0.23912(2) 0.22174(2) 0.02796(4) Uani d 1
N N51 0.6470(2) 0.66039(19) 0.13306(13) 0.0324(4) Uani d 1
C C52 0.6391(2) 0.6643(2) 0.04022(16) 0.0352(4) Uani d 1
H H52 0.6189 0.5758 -0.0002 0.042 Uiso calc 1
C C53 0.6589(2) 0.7913(3) 0.00002(15) 0.0351(4) Uani d 1
H H53 0.6515 0.7886 -0.0664 0.042 Uiso calc 1
C C54 0.6896(2) 0.9218(2) 0.05726(15) 0.0311(4) Uani d 1
C C55 0.7006(2) 0.9175(2) 0.15287(15) 0.0304(4) Uani d 1
H H55 0.7238 1.0044 0.1950 0.037 Uiso calc 1
C C56 0.6779(2) 0.7871(2) 0.18713(14) 0.0307(4) Uani d 1
H H56 0.6846 0.7872 0.2534 0.037 Uiso calc 1
C C57 0.7144(3) 1.0671(3) 0.0218(2) 0.0470(6) Uani d 1
H H57A 0.6192 1.0836 0.0012 0.056 Uiso calc 1
H H57B 0.7580 1.1423 0.0748 0.056 Uiso calc 1
N N61 0.8927(2) 1.50111(19) -0.15155(13) 0.0319(4) Uani d 1
C C62 0.9984(3) 1.4471(2) -0.11592(16) 0.0361(4) Uani d 1
H H62 1.0952 1.5031 -0.1121 0.043 Uiso calc 1
C C63 0.9737(3) 1.3136(3) -0.08434(17) 0.0395(5) Uani d 1
H H63 1.0527 1.2794 -0.0603 0.047 Uiso calc 1
C C64 0.8349(3) 1.2307(2) -0.08775(18) 0.0405(5) Uani d 1
C C65 0.7244(3) 1.2865(2) -0.12439(18) 0.0394(5) Uani d 1
H H65 0.6266 1.2331 -0.1281 0.047 Uiso calc 1
C C66 0.7576(3) 1.4201(2) -0.15542(16) 0.0347(4) Uani d 1
H H66 0.6807 1.4561 -0.1807 0.042 Uiso calc 1
C C67 0.8063(4) 1.0846(3) -0.0550(3) 0.0743(12) Uani d 1
H H67A 0.7608 1.0118 -0.1088 0.089 Uiso calc 1
H H67B 0.9003 1.0647 -0.0353 0.089 Uiso calc 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_3
_geom_angle
C24 C11 C16 . 119.39(17)
C24 C11 C12 . 122.15(16)
C16 C11 C12 . 118.46(16)
C13 C12 C31 . 119.71(18)
C13 C12 C11 . 120.15(17)
C31 C12 C11 . 120.12(16)
C12 C13 C14 . 120.74(19)
C12 C13 H13 . 119.6
C14 C13 H13 . 119.6
C15 C14 C13 . 120.60(18)
C15 C14 H14 . 119.7
C13 C14 H14 . 119.7
C14 C15 C16 . 121.11(18)
C14 C15 H15 . 119.4
C16 C15 H15 . 119.4
C17 C16 C15 . 121.79(17)
C17 C16 C11 . 119.28(17)
C15 C16 C11 . 118.92(18)
C16 C17 C18 . 121.67(17)
C16 C17 H17 . 119.2
C18 C17 H17 . 119.2
C17 C18 C19 . 121.97(17)
C17 C18 C23 . 119.01(17)
C19 C18 C23 . 119.02(17)
C20 C19 C18 . 121.03(17)
C20 C19 H19 . 119.5
C18 C19 H19 . 119.5
C19 C20 C21 . 120.46(18)
C19 C20 H20 . 119.8
C21 C20 H20 . 119.8
C22 C21 C20 . 121.14(18)
C22 C21 H21 . 119.4
C20 C21 H21 . 119.4
C21 C22 C41 . 121.28(17)
C21 C22 C23 . 119.89(16)
C41 C22 C23 . 118.83(16)
C24 C23 C18 . 119.40(16)
C24 C23 C22 . 122.16(15)
C18 C23 C22 . 118.44(16)
C11 C24 C23 . 121.24(16)
C11 C24 H24 . 119.4
C23 C24 H24 . 119.4
C32 C31 C12 . 177.2(2)
C31 C32 I1 . 175.61(17)
C32 I1 N51 . 175.14(7)
C42 C41 C22 . 175.9(2)
C41 C42 I2 . 175.83(17)
C56 N51 C52 . 116.38(18)
C56 N51 I1 . 115.29(13)
C52 N51 I1 . 128.26(14)
N51 C52 C53 . 123.2(2)
N51 C52 H52 . 118.4
C53 C52 H52 . 118.4
C54 C53 C52 . 119.61(19)
C54 C53 H53 . 120.2
C52 C53 H53 . 120.2
C55 C54 C53 . 117.03(18)
C55 C54 C57 . 118.5(2)
C53 C54 C57 . 124.5(2)
C56 C55 C54 . 119.76(19)
C56 C55 H55 . 120.1
C54 C55 H55 . 120.1
N51 C56 C55 . 123.97(19)
N51 C56 H56 . 118.0
C55 C56 H56 . 118.0
C67 C57 C54 . 115.2(2)
C67 C57 H57A . 108.5
C54 C57 H57A . 108.5
C67 C57 H57B . 108.5
C54 C57 H57B . 108.5
H57A C57 H57B . 107.5
C66 N61 C62 . 116.91(18)
C66 N61 I2 2_675 115.46(14)
C62 N61 I2 2_675 127.63(15)
N61 C62 C63 . 123.3(2)
N61 C62 H62 . 118.4
C63 C62 H62 . 118.4
C64 C63 C62 . 119.9(2)
C64 C63 H63 . 120.1
C62 C63 H63 . 120.1
C63 C64 C65 . 117.1(2)
C63 C64 C67 . 120.6(3)
C65 C64 C67 . 122.2(3)
C66 C65 C64 . 119.6(2)
C66 C65 H65 . 120.2
C64 C65 H65 . 120.2
N61 C66 C65 . 123.2(2)
N61 C66 H66 . 118.4
C65 C66 H66 . 118.4
C57 C67 C64 . 115.1(2)
C57 C67 H67A . 108.5
C64 C67 H67A . 108.5
C57 C67 H67B . 108.5
C64 C67 H67B . 108.5
H67A C67 H67B . 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C11 C24 . 1.395(2)
C11 C16 . 1.434(2)
C11 C12 . 1.441(3)
C12 C13 . 1.377(3)
C12 C31 . 1.432(3)
C13 C14 . 1.417(3)
C13 H13 . 0.9500
C14 C15 . 1.357(3)
C14 H14 . 0.9500
C15 C16 . 1.430(3)
C15 H15 . 0.9500
C16 C17 . 1.390(3)
C17 C18 . 1.396(3)
C17 H17 . 0.9500
C18 C19 . 1.428(3)
C18 C23 . 1.436(2)
C19 C20 . 1.361(3)
C19 H19 . 0.9500
C20 C21 . 1.412(3)
C20 H20 . 0.9500
C21 C22 . 1.379(3)
C21 H21 . 0.9500
C22 C41 . 1.430(2)
C22 C23 . 1.441(2)
C23 C24 . 1.396(3)
C24 H24 . 0.9500
C31 C32 . 1.206(3)
C32 I1 . 2.016(2)
I1 N51 . 2.8088(18)
C41 C42 . 1.206(3)
C42 I2 . 2.0219(19)
N51 C56 . 1.333(3)
N51 C52 . 1.337(3)
C52 C53 . 1.387(3)
C52 H52 . 0.9500
C53 C54 . 1.384(3)
C53 H53 . 0.9500
C54 C55 . 1.378(3)
C54 C57 . 1.513(3)
C55 C56 . 1.375(3)
C55 H55 . 0.9500
C56 H56 . 0.9500
C57 C67 . 1.446(4)
C57 H57A . 0.9900
C57 H57B . 0.9900
N61 C66 . 1.336(3)
N61 C62 . 1.336(3)
N61 I2 2_675 2.7614(17)
C62 C63 . 1.384(3)
C62 H62 . 0.9500
C63 C64 . 1.372(4)
C63 H63 . 0.9500
C64 C65 . 1.390(4)
C64 C67 . 1.502(3)
C65 C66 . 1.381(3)
C65 H65 . 0.9500
C66 H66 . 0.9500
C67 H67A . 0.9900
C67 H67B . 0.9900
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
C24 C11 C12 C13 . 178.56(17)
C16 C11 C12 C13 . -0.9(3)
C24 C11 C12 C31 . -2.9(3)
C16 C11 C12 C31 . 177.58(16)
C31 C12 C13 C14 . -178.52(17)
C11 C12 C13 C14 . 0.0(3)
C12 C13 C14 C15 . 0.8(3)
C13 C14 C15 C16 . -0.6(3)
C14 C15 C16 C17 . -179.75(19)
C14 C15 C16 C11 . -0.3(3)
C24 C11 C16 C17 . 1.0(3)
C12 C11 C16 C17 . -179.48(17)
C24 C11 C16 C15 . -178.41(17)
C12 C11 C16 C15 . 1.1(3)
C15 C16 C17 C18 . 178.63(18)
C11 C16 C17 C18 . -0.8(3)
C16 C17 C18 C19 . -179.57(18)
C16 C17 C18 C23 . -0.4(3)
C17 C18 C19 C20 . 179.35(19)
C23 C18 C19 C20 . 0.1(3)
C18 C19 C20 C21 . -0.8(3)
C19 C20 C21 C22 . 0.1(3)
C20 C21 C22 C41 . -178.04(18)
C20 C21 C22 C23 . 1.3(3)
C17 C18 C23 C24 . 1.3(3)
C19 C18 C23 C24 . -179.45(17)
C17 C18 C23 C22 . -178.06(16)
C19 C18 C23 C22 . 1.2(3)
C21 C22 C23 C24 . 178.76(17)
C41 C22 C23 C24 . -1.9(3)
C21 C22 C23 C18 . -1.9(3)
C41 C22 C23 C18 . 177.47(16)
C16 C11 C24 C23 . -0.1(3)
C12 C11 C24 C23 . -179.55(16)
C18 C23 C24 C11 . -1.1(3)
C22 C23 C24 C11 . 178.26(16)
C56 N51 C52 C53 . -1.1(3)
I1 N51 C52 C53 . -177.91(16)
N51 C52 C53 C54 . 0.5(3)
C52 C53 C54 C55 . 0.8(3)
C52 C53 C54 C57 . 179.5(2)
C53 C54 C55 C56 . -1.5(3)
C57 C54 C55 C56 . 179.7(2)
C52 N51 C56 C55 . 0.3(3)
I1 N51 C56 C55 . 177.58(16)
C54 C55 C56 N51 . 1.0(3)
C55 C54 C57 C67 . 134.6(3)
C53 C54 C57 C67 . -44.1(4)
C66 N61 C62 C63 . 0.4(3)
I2 N61 C62 C63 2_675 -178.46(17)
N61 C62 C63 C64 . -0.8(4)
C62 C63 C64 C65 . 0.5(4)
C62 C63 C64 C67 . 179.2(3)
C63 C64 C65 C66 . 0.1(4)
C67 C64 C65 C66 . -178.5(3)
C62 N61 C66 C65 . 0.3(3)
I2 N61 C66 C65 2_675 179.28(18)
C64 C65 C66 N61 . -0.5(4)
C54 C57 C67 C64 . -178.0(3)
C63 C64 C67 C57 . 119.9(4)
C65 C64 C67 C57 . -61.5(5)
