Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal SOciety of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Milko van der Boom'
_publ_contact_author_address     
;
Organic Chemistry
Weizmann Institute of Science
Herzl st 26
Rehovot
76100
ISRAEL
;

_publ_contact_author_email       MILKO.VANDERBOOM@WEIZMANN.AC.IL

_publ_section_title              
;
Design, synthesis and crystal structure of a multiple
donor-acceptor halogen bonded stilbazole: assembly of unimolecular
interconnected helices
;
loop_
_publ_author_name
'M.van der Boom'
'Andre C. Lucassen'
'Linda Shimon'
'Tatiana Zubkov'

data_v32
_database_code_depnum_ccdc_archive 'CCDC 637114'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 F3 I2 N'
_chemical_formula_weight         486.99

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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.2290(8)
_cell_length_b                   14.112(3)
_cell_length_c                   23.312(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1391.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1909
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    4.539
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.2099
_exptl_absorpt_correction_T_max  0.8049
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1897
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1897
_reflns_number_gt                1654
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect package (Bruker Nonius)'
_computing_cell_refinement       HKL
_computing_data_reduction        HKL
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0262P)^2^+1.3859P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.59(5)
_refine_ls_number_reflns         1897
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 -0.05474(10) -0.18602(3) -0.353294(19) 0.01765(11) Uani 1 1 d . . .
I2 I -0.67455(10) -0.44027(3) -0.17751(2) 0.02031(12) Uani 1 1 d . . .
F1 F -0.3891(10) -0.2774(3) -0.09922(16) 0.0249(10) Uani 1 1 d . . .
F2 F -0.4465(10) -0.3536(3) -0.29451(16) 0.0220(9) Uani 1 1 d . . .
F3 F 0.1380(9) -0.0879(3) -0.23503(17) 0.0236(10) Uani 1 1 d . . .
C1 C 0.2685(18) 0.0077(5) -0.0635(3) 0.0217(17) Uani 1 1 d . . .
C2 C 0.180(2) -0.0174(6) -0.0080(3) 0.034(2) Uani 1 1 d . . .
H2 H 0.0629 -0.0738 -0.0016 0.041 Uiso 1 1 calc R . .
C3 C 0.2623(18) 0.0394(5) 0.0372(3) 0.030(2) Uani 1 1 d . . .
H3 H 0.1928 0.0210 0.0744 0.036 Uiso 1 1 calc R . .
N1 N 0.4336(16) 0.1192(4) 0.0330(3) 0.0257(14) Uani 1 1 d . . .
C4 C 0.5260(19) 0.1412(5) -0.0198(3) 0.0235(17) Uani 1 1 d . . .
H4 H 0.6529 0.1961 -0.0246 0.028 Uiso 1 1 calc R . .
C5 C 0.450(2) 0.0892(5) -0.0682(3) 0.0274(17) Uani 1 1 d . . .
H5 H 0.5216 0.1095 -0.1048 0.033 Uiso 1 1 calc R . .
C6 C 0.1790(17) -0.0468(5) -0.1156(3) 0.0217(16) Uani 1 1 d . . .
H6 H 0.2685 -0.0280 -0.1512 0.026 Uiso 1 1 calc R . .
C7 C -0.0166(18) -0.1196(5) -0.1156(3) 0.0210(17) Uani 1 1 d . . .
H7 H -0.0997 -0.1368 -0.0792 0.025 Uiso 1 1 calc R . .
C8 C -0.1253(14) -0.1785(5) -0.1649(3) 0.0170(15) Uani 1 1 d . . .
C9 C -0.3151(17) -0.2567(5) -0.1542(3) 0.0165(14) Uani 1 1 d . . .
C10 C -0.4261(16) -0.3171(5) -0.1966(3) 0.0195(14) Uani 1 1 d . . .
C11 C -0.3436(17) -0.2950(4) -0.2525(3) 0.0164(15) Uani 1 1 d . . .
C12 C -0.1578(17) -0.2175(5) -0.2674(3) 0.0193(15) Uani 1 1 d . . .
C13 C -0.0523(17) -0.1622(4) -0.2226(3) 0.0185(15) Uani 1 1 d . . .

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 0.0189(2) 0.0200(2) 0.0140(2) -0.00007(19) 0.0014(2) 0.00013(19)
I2 0.0190(2) 0.0187(2) 0.0232(3) 0.0030(2) -0.0003(2) -0.00206(19)
F1 0.034(3) 0.031(2) 0.010(2) 0.0020(17) 0.0032(19) -0.0048(19)
F2 0.030(2) 0.022(2) 0.014(2) -0.0045(17) -0.003(2) -0.0068(19)
F3 0.028(2) 0.026(2) 0.017(2) -0.0003(17) -0.0012(19) -0.0096(19)
C1 0.027(4) 0.024(4) 0.014(4) -0.001(3) -0.001(3) 0.002(3)
C2 0.045(5) 0.038(5) 0.019(4) 0.001(3) 0.000(4) -0.022(4)
C3 0.037(5) 0.043(5) 0.010(4) -0.007(3) 0.007(3) -0.017(4)
N1 0.028(3) 0.034(4) 0.016(3) -0.008(3) -0.004(3) -0.001(3)
C4 0.033(4) 0.024(4) 0.014(4) -0.004(3) 0.005(3) -0.005(3)
C5 0.037(4) 0.021(4) 0.024(4) 0.002(3) -0.002(4) -0.007(4)
C6 0.026(3) 0.031(4) 0.008(3) -0.001(3) -0.002(3) 0.004(4)
C7 0.027(4) 0.025(4) 0.012(4) 0.000(3) 0.001(3) 0.005(3)
C8 0.015(3) 0.019(3) 0.017(3) 0.006(3) 0.003(3) 0.006(3)
C9 0.021(3) 0.022(4) 0.006(3) 0.002(3) 0.003(3) 0.005(3)
C10 0.015(3) 0.016(3) 0.028(4) 0.003(3) 0.003(3) 0.005(3)
C11 0.022(3) 0.009(3) 0.019(4) 0.001(3) -0.005(3) -0.002(3)
C12 0.017(3) 0.023(4) 0.017(4) 0.001(3) 0.003(3) 0.003(3)
C13 0.015(3) 0.021(4) 0.020(4) -0.001(3) 0.003(3) -0.004(3)

_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 C12 2.096(7) . ?
I2 C10 2.080(7) . ?
F1 C9 1.351(7) . ?
F2 C11 1.355(7) . ?
F3 C13 1.353(7) . ?
C1 C5 1.387(10) . ?
C1 C2 1.391(10) . ?
C1 C6 1.488(9) . ?
C2 C3 1.370(10) . ?
C2 H2 0.9500 . ?
C3 N1 1.342(9) . ?
C3 H3 0.9500 . ?
N1 C4 1.328(9) . ?
C4 C5 1.383(9) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.319(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.490(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(9) . ?
C8 C13 1.400(9) . ?
C9 C10 1.387(9) . ?
C10 C11 1.384(9) . ?
C11 C12 1.391(9) . ?
C12 C13 1.379(9) . ?

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
C5 C1 C2 115.6(7) . . ?
C5 C1 C6 120.3(6) . . ?
C2 C1 C6 124.0(7) . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C3 C2 124.8(7) . . ?
N1 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
C4 N1 C3 115.0(6) . . ?
N1 C4 C5 124.3(7) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C1 C5 C4 120.3(7) . . ?
C1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C1 124.2(7) . . ?
C7 C6 H6 117.9 . . ?
C1 C6 H6 117.9 . . ?
C6 C7 C8 128.9(7) . . ?
C6 C7 H7 115.5 . . ?
C8 C7 H7 115.5 . . ?
C9 C8 C13 115.5(6) . . ?
C9 C8 C7 119.0(6) . . ?
C13 C8 C7 125.5(6) . . ?
F1 C9 C10 117.7(6) . . ?
F1 C9 C8 118.4(6) . . ?
C10 C9 C8 123.8(6) . . ?
C11 C10 C9 116.6(6) . . ?
C11 C10 I2 121.1(5) . . ?
C9 C10 I2 122.1(5) . . ?
F2 C11 C10 117.5(6) . . ?
F2 C11 C12 118.7(6) . . ?
C10 C11 C12 123.8(6) . . ?
C13 C12 C11 115.9(6) . . ?
C13 C12 I1 122.5(5) . . ?
C11 C12 I1 121.6(5) . . ?
F3 C13 C12 117.9(6) . . ?
F3 C13 C8 117.7(6) . . ?
C12 C13 C8 124.4(6) . . ?

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
C5 C1 C2 C3 2.5(12) . . . . ?
C6 C1 C2 C3 -177.2(8) . . . . ?
C1 C2 C3 N1 -1.7(13) . . . . ?
C2 C3 N1 C4 -0.4(12) . . . . ?
C3 N1 C4 C5 1.7(11) . . . . ?
C2 C1 C5 C4 -1.3(11) . . . . ?
C6 C1 C5 C4 178.4(7) . . . . ?
N1 C4 C5 C1 -0.8(12) . . . . ?
C5 C1 C6 C7 -173.2(7) . . . . ?
C2 C1 C6 C7 6.4(12) . . . . ?
C1 C6 C7 C8 179.3(7) . . . . ?
C6 C7 C8 C9 175.2(7) . . . . ?
C6 C7 C8 C13 -4.8(12) . . . . ?
C13 C8 C9 F1 178.7(6) . . . . ?
C7 C8 C9 F1 -1.3(9) . . . . ?
C13 C8 C9 C10 0.9(10) . . . . ?
C7 C8 C9 C10 -179.1(6) . . . . ?
F1 C9 C10 C11 -179.2(6) . . . . ?
C8 C9 C10 C11 -1.3(10) . . . . ?
F1 C9 C10 I2 -3.7(9) . . . . ?
C8 C9 C10 I2 174.1(5) . . . . ?
C9 C10 C11 F2 179.2(6) . . . . ?
I2 C10 C11 F2 3.7(9) . . . . ?
C9 C10 C11 C12 0.5(10) . . . . ?
I2 C10 C11 C12 -175.0(5) . . . . ?
F2 C11 C12 C13 -178.0(6) . . . . ?
C10 C11 C12 C13 0.7(10) . . . . ?
F2 C11 C12 I1 3.2(9) . . . . ?
C10 C11 C12 I1 -178.0(5) . . . . ?
C11 C12 C13 F3 177.8(5) . . . . ?
I1 C12 C13 F3 -3.5(9) . . . . ?
C11 C12 C13 C8 -1.2(11) . . . . ?
I1 C12 C13 C8 177.5(5) . . . . ?
C9 C8 C13 F3 -178.6(5) . . . . ?
C7 C8 C13 F3 1.4(10) . . . . ?
C9 C8 C13 C12 0.5(10) . . . . ?
C7 C8 C13 C12 -179.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.165


