# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

 
data_p2(1)-c 
 
_audit_creation_method            SHELXTL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C28 H10 Br2 F12 N2' 
_chemical_formula_weight          762.20 
 
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            monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    20.1093(5) 
_cell_length_b                    4.67830(10) 
_cell_length_c                    14.0181(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.8770(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1311.85(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.930 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              740 
_exptl_absorpt_coefficient_mu     3.199 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5671 
_exptl_absorpt_correction_T_max   0.7403 
_exptl_absorpt_process_details    'SADABS (Bruker, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(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 APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15746 
_diffrn_reflns_av_R_equivalents   0.0276 
_diffrn_reflns_av_sigmaI/netI     0.0205 
_diffrn_reflns_limit_h_min        -24 
_diffrn_reflns_limit_h_max        24 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          2.04 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              2531 
_reflns_number_gt                 2320 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker APEX-II' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
 
_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)+(0.0276P)²+0.6022P] 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_number_reflns          2531 
_refine_ls_number_parameters      199 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0233 
_refine_ls_R_factor_gt            0.0200 
_refine_ls_wR_factor_ref          0.0524 
_refine_ls_wR_factor_gt           0.0513 
_refine_ls_goodness_of_fit_ref    1.068 
_refine_ls_restrained_S_all       1.068 
_refine_ls_shift/su_max           0.004 
_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 
Br1 Br 0.573157(8) -0.19511(4) 0.812771(11) 0.01725(7) Uani 1 1 d . . . 
C1 C 0.87200(8) 0.6062(4) 0.98640(12) 0.0164(4) Uani 1 1 d . . . 
H1 H 0.9138 0.6834 0.9733 0.020 Uiso 1 1 calc R . . 
C2 C 0.86805(8) 0.4208(4) 1.06305(12) 0.0156(4) Uani 1 1 d . . . 
C3 C 0.80698(8) 0.3073(4) 1.08266(12) 0.0147(4) Uani 1 1 d . . . 
H3 H 0.8049 0.1820 1.1356 0.018 Uiso 1 1 calc R . . 
C4 C 0.74877(8) 0.3778(4) 1.02444(12) 0.0143(4) Uani 1 1 d . . . 
C5 C 0.75242(8) 0.5656(4) 0.94758(11) 0.0145(3) Uani 1 1 d . . . 
H5 H 0.7130 0.6170 0.9081 0.017 Uiso 1 1 calc R . . 
C6 C 0.81383(9) 0.6765(4) 0.92925(12) 0.0154(4) Uani 1 1 d . . . 
C7 C 0.68340(8) 0.2492(4) 1.04206(12) 0.0149(4) Uani 1 1 d . . . 
C8 C 0.63164(8) 0.2198(4) 0.97445(12) 0.0148(4) Uani 1 1 d . . . 
H8 H 0.6386 0.2779 0.9113 0.018 Uiso 1 1 calc R . . 
C9 C 0.56490(8) 0.1061(4) 0.98850(12) 0.0142(3) Uani 1 1 d . . . 
C10 C 0.53044(8) -0.0728(4) 0.92007(11) 0.0141(3) Uani 1 1 d . . . 
C11 C 0.46750(8) -0.1782(4) 0.93112(12) 0.0156(4) Uani 1 1 d . . . 
H11 H 0.4460 -0.3011 0.8836 0.019 Uiso 1 1 calc R . . 
C12 C 0.93184(9) 0.3374(4) 1.12175(13) 0.0200(4) Uani 1 1 d . . . 
C13 C 0.81824(9) 0.8655(4) 0.84367(13) 0.0195(4) Uani 1 1 d . . . 
C14 C 0.67912(8) 0.1347(4) 1.13738(13) 0.0208(4) Uani 1 1 d . . . 
F1 F 0.97131(6) 0.1853(3) 1.06909(9) 0.0343(3) Uani 1 1 d . . . 
F2 F 0.96738(6) 0.5618(3) 1.15373(11) 0.0508(4) Uani 1 1 d . . . 
F3 F 0.92158(5) 0.1749(3) 1.19649(8) 0.0356(3) Uani 1 1 d . . . 
F4 F 0.83001(6) 0.7142(2) 0.76572(8) 0.0283(3) Uani 1 1 d . . . 
F5 F 0.86732(6) 1.0569(3) 0.85792(8) 0.0322(3) Uani 1 1 d . . . 
F6 F 0.76153(6) 1.0107(2) 0.81968(8) 0.0296(3) Uani 1 1 d . . . 
N1 N 0.67695(8) 0.0403(4) 1.21195(12) 0.0348(5) Uani 1 1 d . . . 
 
 
_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 
Br1 C10 1.8953(16) . ? 
C1 C6 1.388(2) . ? 
C1 C2 1.389(3) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.391(2) . ? 
C2 C12 1.503(2) . ? 
C3 C4 1.396(2) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.398(2) . ? 
C4 C7 1.489(2) . ? 
C5 C6 1.388(2) . ? 
C5 H5 0.9500 . ? 
C6 C13 1.500(2) . ? 
C7 C8 1.341(2) . ? 
C7 C14 1.450(2) . ? 
C8 C9 1.475(2) . ? 
C8 H8 0.9500 . ? 
C9 C11 1.399(2) 3_657 ? 
C9 C10 1.402(2) . ? 
C10 C11 1.382(2) . ? 
C11 C9 1.399(2) 3_657 ? 
C11 H11 0.9500 . ? 
C12 F2 1.322(2) . ? 
C12 F3 1.328(2) . ? 
C12 F1 1.342(2) . ? 
C13 F5 1.332(2) . ? 
C13 F6 1.340(2) . ? 
C13 F4 1.343(2) . ? 
C14 N1 1.140(2) . ? 
 
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 
C6 C1 C2 118.86(16) . . ? 
C6 C1 H1 120.6 . . ? 
C2 C1 H1 120.6 . . ? 
C1 C2 C3 120.85(16) . . ? 
C1 C2 C12 118.18(15) . . ? 
C3 C2 C12 120.93(16) . . ? 
C2 C3 C4 119.91(16) . . ? 
C2 C3 H3 120.0 . . ? 
C4 C3 H3 120.0 . . ? 
C3 C4 C5 119.47(15) . . ? 
C3 C4 C7 120.61(15) . . ? 
C5 C4 C7 119.90(15) . . ? 
C6 C5 C4 119.71(15) . . ? 
C6 C5 H5 120.1 . . ? 
C4 C5 H5 120.1 . . ? 
C5 C6 C1 121.19(16) . . ? 
C5 C6 C13 119.68(16) . . ? 
C1 C6 C13 119.07(16) . . ? 
C8 C7 C14 119.89(16) . . ? 
C8 C7 C4 123.96(16) . . ? 
C14 C7 C4 116.02(15) . . ? 
C7 C8 C9 126.40(16) . . ? 
C7 C8 H8 116.8 . . ? 
C9 C8 H8 116.8 . . ? 
C11 C9 C10 117.17(15) 3_657 . ? 
C11 C9 C8 121.69(15) 3_657 . ? 
C10 C9 C8 121.11(15) . . ? 
C11 C10 C9 122.06(16) . . ? 
C11 C10 Br1 118.43(13) . . ? 
C9 C10 Br1 119.40(12) . . ? 
C10 C11 C9 120.77(16) . 3_657 ? 
C10 C11 H11 119.6 . . ? 
C9 C11 H11 119.6 3_657 . ? 
F2 C12 F3 108.03(15) . . ? 
F2 C12 F1 106.14(15) . . ? 
F3 C12 F1 106.20(15) . . ? 
F2 C12 C2 112.38(15) . . ? 
F3 C12 C2 112.82(15) . . ? 
F1 C12 C2 110.86(15) . . ? 
F5 C13 F6 107.18(15) . . ? 
F5 C13 F4 106.65(15) . . ? 
F6 C13 F4 106.22(14) . . ? 
F5 C13 C6 112.31(15) . . ? 
F6 C13 C6 112.39(15) . . ? 
F4 C13 C6 111.70(15) . . ? 
N1 C14 C7 178.4(2) . . ? 
 
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 
C6 C1 C2 C3 -0.1(3) . . . . ? 
C6 C1 C2 C12 177.54(15) . . . . ? 
C1 C2 C3 C4 0.5(3) . . . . ? 
C12 C2 C3 C4 -177.07(16) . . . . ? 
C2 C3 C4 C5 -0.9(3) . . . . ? 
C2 C3 C4 C7 177.55(16) . . . . ? 
C3 C4 C5 C6 0.9(2) . . . . ? 
C7 C4 C5 C6 -177.58(16) . . . . ? 
C4 C5 C6 C1 -0.5(3) . . . . ? 
C4 C5 C6 C13 176.73(16) . . . . ? 
C2 C1 C6 C5 0.1(3) . . . . ? 
C2 C1 C6 C13 -177.14(16) . . . . ? 
C3 C4 C7 C8 -155.20(17) . . . . ? 
C5 C4 C7 C8 23.2(3) . . . . ? 
C3 C4 C7 C14 20.6(2) . . . . ? 
C5 C4 C7 C14 -160.93(16) . . . . ? 
C14 C7 C8 C9 7.2(3) . . . . ? 
C4 C7 C8 C9 -177.13(17) . . . . ? 
C7 C8 C9 C11 41.4(3) . . . 3_657 ? 
C7 C8 C9 C10 -140.51(18) . . . . ? 
C11 C9 C10 C11 -0.8(3) 3_657 . . . ? 
C8 C9 C10 C11 -179.02(16) . . . . ? 
C11 C9 C10 Br1 -176.75(12) 3_657 . . . ? 
C8 C9 C10 Br1 5.1(2) . . . . ? 
C9 C10 C11 C9 0.9(3) . . . 3_657 ? 
Br1 C10 C11 C9 176.82(13) . . . 3_657 ? 
C1 C2 C12 F2 53.5(2) . . . . ? 
C3 C2 C12 F2 -128.88(18) . . . . ? 
C1 C2 C12 F3 175.91(16) . . . . ? 
C3 C2 C12 F3 -6.4(2) . . . . ? 
C1 C2 C12 F1 -65.1(2) . . . . ? 
C3 C2 C12 F1 112.53(18) . . . . ? 
C5 C6 C13 F5 149.88(16) . . . . ? 
C1 C6 C13 F5 -32.8(2) . . . . ? 
C5 C6 C13 F6 28.9(2) . . . . ? 
C1 C6 C13 F6 -153.79(16) . . . . ? 
C5 C6 C13 F4 -90.34(19) . . . . ? 
C1 C6 C13 F4 86.9(2) . . . . ? 
C8 C7 C14 N1 116(8) . . . . ? 
C4 C7 C14 N1 -60(8) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.982 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.982 
_refine_diff_density_max    0.365 
_refine_diff_density_min   -0.295 
_refine_diff_density_rms    0.056 
