# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jesus Valdes-Martinez'
_publ_contact_author_email       JVALDES@SERVIDOR.UNAM.MX

_publ_section_title              
;
Bottom-up design and construction of a
non-centrosymmetric network through pi-pi stacking interactions
;
loop_
_publ_author_name
'Jesus Valdes-Martinez'
'Simon Hernandez-Ortega'
'David Morales-Morales'
;
J.M.Serrano-Becerra
;

# Attachment 'B814639J.cif'

data_074mmd05
_database_code_depnum_ccdc_archive 'CCDC 698873'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide
;
_chemical_name_common            
'1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide'
_chemical_melting_point_gt       444
_chemical_melting_point_lt       446
_chemical_formula_moiety         'C17 H12 F5 N2+, Br-'
_chemical_formula_sum            'C17 H12 Br F5 N2'
_chemical_formula_weight         419.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.4341(12)
_cell_length_b                   7.3046(14)
_cell_length_c                   8.8257(17)
_cell_angle_alpha                85.980(4)
_cell_angle_beta                 88.527(4)
_cell_angle_gamma                83.187(4)
_cell_volume                     410.79(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2237
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.70

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_T_max  0.7161
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker Smart APEX AXS CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3387
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2776
_reflns_number_gt                2406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625'
_computing_cell_refinement       'SMART V 5.625'
_computing_data_reduction        'SAINT V 6.23C'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL V 6.10'
_computing_publication_material  'SHELXTL V 6.10'
#_solved_by SimonHO

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0383P)²] where P=(Fo²+2Fc²)/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   -0.006(7)
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     226
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.000
_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
Br Br 0.88614(4) 0.79616(4) 0.70350(4) 0.07038(19) Uani 1 1 d . . .
F1 F 0.1388(4) 0.5420(4) 0.3812(3) 0.0797(8) Uani 1 1 d . . .
F2 F 0.2301(6) 0.4859(5) 0.0881(3) 0.1026(12) Uani 1 1 d . . .
F3 F 0.6176(7) 0.3436(5) 0.0057(3) 0.1121(13) Uani 1 1 d . . .
F4 F 0.9125(7) 0.2500(4) 0.2174(5) 0.1021(13) Uani 1 1 d . . .
F5 F 0.8223(5) 0.3063(4) 0.5105(4) 0.0872(9) Uani 1 1 d . . .
N1 N 0.3187(7) 0.0639(6) 0.8308(4) 0.0464(10) Uani 1 1 d . . .
C2 C 0.4447(8) 0.1580(7) 0.7493(5) 0.0481(11) Uani 1 1 d . . .
H2 H 0.5825 0.1158 0.7242 0.058 Uiso 1 1 calc R . .
N3 N 0.3485(6) 0.3220(5) 0.7074(4) 0.0474(11) Uani 1 1 d . . .
C4 C 0.1480(7) 0.3310(6) 0.7631(5) 0.0576(12) Uani 1 1 d . . .
H4 H 0.0440 0.4304 0.7499 0.069 Uiso 1 1 calc R . .
C5 C 0.1301(7) 0.1700(6) 0.8399(5) 0.0578(12) Uani 1 1 d . . .
H5 H 0.0106 0.1361 0.8905 0.069 Uiso 1 1 calc R . .
C6 C 0.4352(11) 0.4747(8) 0.6159(6) 0.0602(15) Uani 1 1 d . . .
H6A H 0.5634 0.5003 0.6615 0.072 Uiso 1 1 calc R . .
H6B H 0.3359 0.5855 0.6171 0.072 Uiso 1 1 calc R . .
C7 C 0.4806(7) 0.4282(5) 0.4538(4) 0.0474(10) Uani 1 1 d . . .
C8 C 0.3290(7) 0.4700(6) 0.3423(5) 0.0539(11) Uani 1 1 d . . .
C9 C 0.3733(9) 0.4409(7) 0.1932(5) 0.0612(12) Uani 1 1 d . . .
C10 C 0.5708(11) 0.3696(7) 0.1522(5) 0.0707(15) Uani 1 1 d . . .
C11 C 0.7212(9) 0.3248(6) 0.2576(6) 0.0657(13) Uani 1 1 d . . .
C12 C 0.6720(8) 0.3536(6) 0.4078(5) 0.0558(11) Uani 1 1 d . . .
C13 C 0.3709(7) -0.1242(5) 0.9057(5) 0.0517(10) Uani 1 1 d . . .
H13A H 0.4897 -0.1880 0.8535 0.062 Uiso 1 1 calc R . .
H13B H 0.2529 -0.1943 0.8989 0.062 Uiso 1 1 calc R . .
C14 C 0.4228(7) -0.1136(5) 1.0713(4) 0.0475(10) Uani 1 1 d . . .
C15 C 0.6273(7) -0.1537(6) 1.1193(5) 0.0585(11) Uani 1 1 d . . .
H15 H 0.7339 -0.1843 1.0492 0.070 Uiso 1 1 calc R . .
C16 C 0.6735(8) -0.1484(7) 1.2700(6) 0.0667(14) Uani 1 1 d . . .
H16 H 0.8110 -0.1762 1.3018 0.080 Uiso 1 1 calc R . .
C17 C 0.5171(10) -0.1024(7) 1.3731(6) 0.0709(15) Uani 1 1 d . . .
H17 H 0.5486 -0.0993 1.4751 0.085 Uiso 1 1 calc R . .
C18 C 0.3143(9) -0.0607(7) 1.3271(5) 0.0712(14) Uani 1 1 d . . .
H18 H 0.2081 -0.0277 1.3969 0.085 Uiso 1 1 calc R . .
C19 C 0.2700(8) -0.0684(6) 1.1763(5) 0.0606(12) Uani 1 1 d . . .
H19 H 0.1320 -0.0421 1.1452 0.073 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
Br 0.0653(3) 0.0637(3) 0.0793(3) -0.0159(2) -0.0157(2) 0.0143(2)
F1 0.0644(19) 0.0780(19) 0.094(2) 0.0023(16) -0.0060(15) -0.0008(15)
F2 0.133(3) 0.113(3) 0.0692(18) 0.0180(17) -0.0489(19) -0.050(2)
F3 0.178(4) 0.116(3) 0.0548(18) -0.0306(17) 0.033(2) -0.062(3)
F4 0.092(3) 0.074(3) 0.138(3) -0.021(3) 0.038(2) -0.001(2)
F5 0.076(2) 0.079(2) 0.102(2) 0.0103(17) -0.0286(18) 0.0053(16)
N1 0.053(2) 0.046(2) 0.039(2) 0.0035(17) -0.0080(18) -0.0002(19)
C2 0.055(3) 0.051(3) 0.036(2) -0.010(2) -0.008(2) 0.006(2)
N3 0.065(3) 0.041(3) 0.0364(16) -0.0034(17) -0.0039(18) -0.003(2)
C4 0.062(3) 0.053(3) 0.053(3) 0.002(2) -0.016(2) 0.010(2)
C5 0.053(3) 0.059(3) 0.060(3) 0.003(2) -0.006(2) 0.000(2)
C6 0.085(4) 0.048(3) 0.048(3) -0.007(2) -0.007(3) -0.004(3)
C7 0.062(3) 0.035(2) 0.045(2) 0.0025(18) -0.007(2) -0.007(2)
C8 0.062(3) 0.040(2) 0.060(3) 0.001(2) -0.006(2) -0.010(2)
C9 0.083(4) 0.059(3) 0.046(3) 0.004(2) -0.017(3) -0.025(3)
C10 0.110(5) 0.059(3) 0.049(3) -0.012(2) 0.011(3) -0.032(3)
C11 0.074(4) 0.046(3) 0.080(4) -0.012(3) 0.017(3) -0.014(3)
C12 0.065(3) 0.040(2) 0.062(3) 0.005(2) -0.014(2) -0.008(2)
C13 0.061(3) 0.038(2) 0.055(2) 0.0017(19) -0.010(2) 0.0001(19)
C14 0.058(3) 0.035(2) 0.049(2) 0.0043(18) -0.007(2) -0.0053(19)
C15 0.057(3) 0.053(3) 0.064(3) 0.009(2) -0.003(2) -0.005(2)
C16 0.066(3) 0.062(3) 0.073(3) 0.016(3) -0.032(3) -0.018(3)
C17 0.109(5) 0.053(3) 0.052(3) 0.007(2) -0.017(3) -0.018(3)
C18 0.090(4) 0.060(3) 0.060(3) 0.002(2) 0.001(3) 0.007(3)
C19 0.061(3) 0.058(3) 0.059(3) 0.005(2) -0.011(2) 0.009(2)

_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
F1 C8 1.320(5) . ?
F2 C9 1.321(5) . ?
F3 C10 1.342(5) . ?
F4 C11 1.336(7) . ?
F5 C12 1.341(5) . ?
N1 C2 1.296(6) . ?
N1 C5 1.364(6) . ?
N1 C13 1.487(5) . ?
C2 N3 1.315(7) . ?
N3 C4 1.365(6) . ?
N3 C6 1.485(7) . ?
C4 C5 1.331(6) . ?
C6 C7 1.507(7) . ?
C7 C12 1.351(6) . ?
C7 C8 1.396(6) . ?
C8 C9 1.365(6) . ?
C9 C10 1.365(7) . ?
C10 C11 1.355(8) . ?
C11 C12 1.380(7) . ?
C13 C14 1.517(5) . ?
C14 C19 1.361(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.374(6) . ?
C16 C17 1.367(8) . ?
C17 C18 1.370(7) . ?
C18 C19 1.374(6) . ?

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
C2 N1 C5 107.9(4) . . ?
C2 N1 C13 126.4(4) . . ?
C5 N1 C13 125.7(4) . . ?
N1 C2 N3 109.8(4) . . ?
C2 N3 C4 107.9(4) . . ?
C2 N3 C6 127.9(4) . . ?
C4 N3 C6 124.3(4) . . ?
C5 C4 N3 106.7(4) . . ?
C4 C5 N1 107.6(4) . . ?
N3 C6 C7 111.9(4) . . ?
C12 C7 C8 116.9(4) . . ?
C12 C7 C6 121.8(4) . . ?
C8 C7 C6 121.2(5) . . ?
F1 C8 C9 119.0(4) . . ?
F1 C8 C7 119.4(4) . . ?
C9 C8 C7 121.6(5) . . ?
F2 C9 C10 119.8(5) . . ?
F2 C9 C8 121.0(5) . . ?
C10 C9 C8 119.1(4) . . ?
F3 C10 C11 119.3(6) . . ?
F3 C10 C9 119.8(5) . . ?
C11 C10 C9 120.9(4) . . ?
F4 C11 C10 120.6(5) . . ?
F4 C11 C12 120.4(5) . . ?
C10 C11 C12 118.9(5) . . ?
F5 C12 C7 119.5(4) . . ?
F5 C12 C11 118.0(5) . . ?
C7 C12 C11 122.5(4) . . ?
N1 C13 C14 110.8(3) . . ?
C19 C14 C15 118.5(4) . . ?
C19 C14 C13 121.1(4) . . ?
C15 C14 C13 120.4(4) . . ?
C16 C15 C14 120.3(4) . . ?
C17 C16 C15 119.9(5) . . ?
C16 C17 C18 120.4(5) . . ?
C17 C18 C19 119.1(5) . . ?
C14 C19 C18 121.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050


