# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Shishkin, Oleg'
'Dyakonenko, Viktoriya'
'Maleev, Andrey'
'Schollmeyer, Dieter'
'Vysotsky, Myroslav'

_publ_contact_author_name        'Shishkin, Oleg'
_publ_contact_author_email       shishkin@xray.isc.kharkov.com

_publ_section_title              
;
Columnar Supramolecular Architecture of Crystals
of 2-(4-Iodophenyl)-1,10-Phenanthroline Derived from Values
of Intermolecular Interaction Energy

;

# Attachment '- phth1.cif'

data_phth1
_database_code_depnum_ccdc_archive 'CCDC 779577'
#TrackingRef '- phth1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 I N2'
_chemical_formula_weight         382.19

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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'

_cell_length_a                   8.9604(3)
_cell_length_b                   17.5585(6)
_cell_length_c                   9.1950(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2519(17)
_cell_angle_gamma                90.00
_cell_volume                     1440.59(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    8463
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.45
_exptl_absorpt_process_details   'MULABS (Blessing, 1971)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_method       'CCD scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25765
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.08
_reflns_number_total             3497
_reflns_number_gt                3235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 V2.0 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 V2.0 (Bruker, 2006)'
_computing_data_reduction        'APEX2 V2.0 (Bruker, 2006)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.7140P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3497
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_obs         0.0595
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I 0.360939(15) 0.156395(8) 0.725246(14) 0.03333(6) Uani 1 1 d . . .
N1 N 0.58919(17) 0.47376(9) 0.32585(16) 0.0229(3) Uani 1 1 d . . .
C2 C 0.6161(2) 0.53333(10) 0.23872(19) 0.0228(3) Uani 1 1 d . . .
C3 C 0.7651(2) 0.56700(11) 0.2519(2) 0.0247(4) Uani 1 1 d . . .
N4 N 0.87170(19) 0.53635(10) 0.34940(19) 0.0296(3) Uani 1 1 d . . .
C5 C 1.0038(2) 0.57118(13) 0.3671(2) 0.0357(5) Uani 1 1 d . . .
H5 H 1.0788 0.5500 0.4349 0.043 Uiso 1 1 calc R . .
C6 C 1.0391(3) 0.63716(15) 0.2921(3) 0.0412(5) Uani 1 1 d . . .
H6 H 1.1345 0.6606 0.3109 0.049 Uiso 1 1 calc R . .
C7 C 0.9335(3) 0.66739(13) 0.1910(3) 0.0379(5) Uani 1 1 d . . .
H7 H 0.9551 0.7119 0.1379 0.045 Uiso 1 1 calc R . .
C8 C 0.7928(2) 0.63173(12) 0.1669(2) 0.0286(4) Uani 1 1 d . . .
C9 C 0.6784(3) 0.65968(11) 0.0606(2) 0.0312(4) Uani 1 1 d . . .
H9 H 0.6996 0.7014 -0.0001 0.037 Uiso 1 1 calc R . .
C10 C 0.5410(2) 0.62728(11) 0.0460(2) 0.0299(4) Uani 1 1 d . . .
H10 H 0.4675 0.6458 -0.0265 0.036 Uiso 1 1 calc R . .
C11 C 0.5048(2) 0.56557(10) 0.13804(19) 0.0253(4) Uani 1 1 d . . .
C12 C 0.3588(2) 0.53548(12) 0.1368(2) 0.0302(4) Uani 1 1 d . . .
H12 H 0.2799 0.5558 0.0722 0.036 Uiso 1 1 calc R . .
C13 C 0.3310(2) 0.47719(12) 0.2284(2) 0.0294(4) Uani 1 1 d . . .
H13 H 0.2323 0.4577 0.2303 0.035 Uiso 1 1 calc R . .
C14 C 0.4508(2) 0.44585(10) 0.32081(19) 0.0238(4) Uani 1 1 d . . .
C15 C 0.4287(2) 0.37913(10) 0.41638(19) 0.0231(3) Uani 1 1 d . . .
C16 C 0.5414(2) 0.35714(10) 0.5226(2) 0.0238(4) Uani 1 1 d . . .
H16 H 0.6325 0.3851 0.5336 0.029 Uiso 1 1 calc R . .
C17 C 0.5224(2) 0.29484(11) 0.6131(2) 0.0246(4) Uani 1 1 d . . .
H17 H 0.6000 0.2807 0.6854 0.029 Uiso 1 1 calc R . .
C18 C 0.3899(2) 0.25355(11) 0.5970(2) 0.0259(4) Uani 1 1 d . . .
C19 C 0.2765(2) 0.27469(13) 0.4919(2) 0.0351(5) Uani 1 1 d . . .
H19 H 0.1857 0.2465 0.4811 0.042 Uiso 1 1 calc R . .
C20 C 0.2957(2) 0.33676(12) 0.4028(2) 0.0337(4) Uani 1 1 d . . .
H20 H 0.2173 0.3509 0.3313 0.040 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03499(9) 0.03149(9) 0.03266(9) 0.00481(5) -0.00149(6) -0.01100(5)
N1 0.0243(7) 0.0207(7) 0.0240(7) -0.0008(6) 0.0034(6) 0.0029(6)
C2 0.0273(9) 0.0201(8) 0.0210(8) -0.0019(6) 0.0026(6) 0.0069(7)
C3 0.0279(9) 0.0224(8) 0.0245(8) 0.0024(7) 0.0055(7) 0.0048(7)
N4 0.0258(8) 0.0297(8) 0.0330(8) 0.0096(7) 0.0019(6) 0.0017(7)
C5 0.0271(10) 0.0375(11) 0.0421(11) 0.0131(9) 0.0012(8) -0.0001(8)
C6 0.0288(11) 0.0447(12) 0.0499(13) 0.0168(11) 0.0033(9) -0.0063(10)
C7 0.0376(12) 0.0348(11) 0.0425(12) 0.0168(9) 0.0104(9) -0.0017(9)
C8 0.0333(10) 0.0268(9) 0.0266(9) 0.0055(7) 0.0067(8) 0.0053(8)
C9 0.0426(12) 0.0265(10) 0.0253(9) 0.0075(7) 0.0062(8) 0.0080(8)
C10 0.0398(11) 0.0268(9) 0.0224(8) 0.0013(7) 0.0000(7) 0.0125(8)
C11 0.0319(9) 0.0224(8) 0.0214(8) -0.0031(7) 0.0008(7) 0.0088(7)
C12 0.0305(10) 0.0304(10) 0.0282(9) -0.0029(8) -0.0052(7) 0.0096(8)
C13 0.0244(9) 0.0296(10) 0.0331(10) -0.0036(7) -0.0024(7) 0.0026(7)
C14 0.0251(9) 0.0224(8) 0.0235(8) -0.0049(7) 0.0009(7) 0.0026(7)
C15 0.0222(8) 0.0225(8) 0.0246(8) -0.0037(7) 0.0025(6) -0.0002(7)
C16 0.0225(9) 0.0228(8) 0.0259(9) -0.0047(7) 0.0014(7) -0.0027(7)
C17 0.0242(9) 0.0242(9) 0.0250(8) -0.0027(7) 0.0004(7) -0.0013(7)
C18 0.0272(9) 0.0242(9) 0.0267(9) -0.0017(7) 0.0042(7) -0.0043(7)
C19 0.0240(9) 0.0382(11) 0.0423(11) 0.0049(9) -0.0015(8) -0.0105(8)
C20 0.0237(10) 0.0390(11) 0.0369(11) 0.0045(8) -0.0054(8) -0.0042(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
I1 C18 2.1034(19) . ?
N1 C14 1.331(2) . ?
N1 C2 1.353(2) . ?
C2 C11 1.415(2) . ?
C2 C3 1.455(3) . ?
C3 N4 1.360(2) . ?
C3 C8 1.414(3) . ?
N4 C5 1.329(3) . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(3) . ?
C9 C10 1.352(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.431(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(3) . ?
C12 C13 1.363(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.417(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.488(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.401(3) . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C14 N1 C2 118.70(16) . . ?
N1 C2 C11 122.93(17) . . ?
N1 C2 C3 118.48(16) . . ?
C11 C2 C3 118.57(17) . . ?
N4 C3 C8 122.33(18) . . ?
N4 C3 C2 118.54(16) . . ?
C8 C3 C2 119.10(17) . . ?
C5 N4 C3 117.54(17) . . ?
N4 C5 C6 124.1(2) . . ?
N4 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 119.17(19) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C3 118.04(18) . . ?
C7 C8 C9 121.90(19) . . ?
C3 C8 C9 120.06(19) . . ?
C10 C9 C8 120.68(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.94(18) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C2 116.96(17) . . ?
C12 C11 C10 122.67(17) . . ?
C2 C11 C10 120.35(18) . . ?
C13 C12 C11 119.87(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.41(19) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 122.01(18) . . ?
N1 C14 C15 116.28(16) . . ?
C13 C14 C15 121.70(17) . . ?
C16 C15 C20 118.10(17) . . ?
C16 C15 C14 120.35(16) . . ?
C20 C15 C14 121.54(17) . . ?
C15 C16 C17 121.05(17) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.75(17) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.97(18) . . ?
C19 C18 I1 119.20(14) . . ?
C17 C18 I1 120.80(14) . . ?
C20 C19 C18 120.05(18) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 121.08(19) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C2 C11 -2.5(3) . . . . ?
C14 N1 C2 C3 175.83(16) . . . . ?
N1 C2 C3 N4 1.1(3) . . . . ?
C11 C2 C3 N4 179.51(17) . . . . ?
N1 C2 C3 C8 -176.79(16) . . . . ?
C11 C2 C3 C8 1.6(3) . . . . ?
C8 C3 N4 C5 2.4(3) . . . . ?
C2 C3 N4 C5 -175.36(18) . . . . ?
C3 N4 C5 C6 0.2(3) . . . . ?
N4 C5 C6 C7 -1.7(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C3 1.8(3) . . . . ?
C6 C7 C8 C9 -178.8(2) . . . . ?
N4 C3 C8 C7 -3.4(3) . . . . ?
C2 C3 C8 C7 174.35(19) . . . . ?
N4 C3 C8 C9 177.09(18) . . . . ?
C2 C3 C8 C9 -5.1(3) . . . . ?
C7 C8 C9 C10 -175.8(2) . . . . ?
C3 C8 C9 C10 3.6(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
N1 C2 C11 C12 3.4(3) . . . . ?
C3 C2 C11 C12 -174.98(16) . . . . ?
N1 C2 C11 C10 -178.31(16) . . . . ?
C3 C2 C11 C10 3.3(3) . . . . ?
C9 C10 C11 C12 173.24(19) . . . . ?
C9 C10 C11 C2 -5.0(3) . . . . ?
C2 C11 C12 C13 -1.0(3) . . . . ?
C10 C11 C12 C13 -179.25(18) . . . . ?
C11 C12 C13 C14 -2.0(3) . . . . ?
C2 N1 C14 C13 -0.7(3) . . . . ?
C2 N1 C14 C15 178.54(15) . . . . ?
C12 C13 C14 N1 3.0(3) . . . . ?
C12 C13 C14 C15 -176.21(17) . . . . ?
N1 C14 C15 C16 11.1(2) . . . . ?
C13 C14 C15 C16 -169.68(17) . . . . ?
N1 C14 C15 C20 -168.94(18) . . . . ?
C13 C14 C15 C20 10.3(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 179.94(17) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 I1 177.32(14) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
I1 C18 C19 C20 -177.62(17) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C14 C15 C20 C19 179.80(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.119