# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1479096'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H18 F14 N2'
_chemical_formula_weight         720.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   9.539(5)
_cell_length_b                   5.738(3)
_cell_length_c                   29.193(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.613(17)
_cell_angle_gamma                90
_cell_volume                     1580.0(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4657
_cell_measurement_theta_min      2.7512
_cell_measurement_theta_max      26.7407

_exptl_crystal_description       tabular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8732
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'REQAB, CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC8S, Mercury CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12052
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.751
_diffrn_reflns_theta_max         25.142
_diffrn_reflns_theta_full        25.142
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2817
_reflns_number_gt                2089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          '70/30 disorder of F4A/F4B'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.8966P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2817
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1239(2) 0.3660(4) 0.02762(6) 0.0721(6) Uani 1 1 d . . . . .
N1 N 0.3534(2) 0.4215(5) 0.11163(8) 0.0516(6) Uani 1 1 d . . . . .
C6 C 0.3933(3) 0.5852(5) 0.07870(9) 0.0483(7) Uani 1 1 d . . . . .
C9 C 0.4785(3) 0.9141(5) 0.01642(9) 0.0474(7) Uani 1 1 d . . . . .
C8 C 0.3411(3) 0.9096(6) 0.02713(10) 0.0537(7) Uani 1 1 d . . . . .
H8A H 0.2754 1.0178 0.0133 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2995(3) 0.7488(6) 0.05779(10) 0.0551(8) Uani 1 1 d . . . . .
H7A H 0.2070 0.7514 0.0643 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5307(3) 0.5863(6) 0.06897(11) 0.0626(9) Uani 1 1 d . . . . .
H11A H 0.5958 0.4779 0.0830 0.075 Uiso 1 1 calc R U . . .
F2 F -0.1314(2) 0.3460(6) 0.06540(10) 0.1163(10) Uani 1 1 d . . . . .
F6 F 0.1903(3) 0.3658(6) 0.18708(8) 0.1113(10) Uani 1 1 d . . . . .
C12 C 0.4619(3) 0.3567(6) 0.14988(9) 0.0508(7) Uani 1 1 d . . . . .
C10 C 0.5715(3) 0.7475(7) 0.03854(11) 0.0654(9) Uani 1 1 d . . . . .
H10A H 0.6645 0.7452 0.0325 0.079 Uiso 1 1 calc R U . . .
F7 F 0.2272(2) 0.0232(5) 0.16286(9) 0.0991(8) Uani 1 1 d . . . . .
C1 C 0.2193(3) 0.3321(6) 0.10819(10) 0.0519(7) Uani 1 1 d . . . . .
C2 C 0.1159(3) 0.3107(6) 0.07191(11) 0.0594(8) Uani 1 1 d . . . . .
C17 C 0.5316(3) 0.1467(6) 0.14912(12) 0.0631(9) Uani 1 1 d . . . . .
H17A H 0.5063 0.0411 0.1251 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4979(4) 0.5133(7) 0.18544(11) 0.0641(9) Uani 1 1 d . . . . .
H13A H 0.4496 0.6539 0.1856 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1658(4) 0.2317(8) 0.14983(12) 0.0707(10) Uani 1 1 d . . . . .
C16 C 0.6414(4) 0.0957(7) 0.18530(15) 0.0772(11) Uani 1 1 d . . . . .
H16A H 0.6901 -0.0448 0.1853 0.093 Uiso 1 1 calc R U . . .
C14 C 0.6065(4) 0.4602(9) 0.22100(12) 0.0845(12) Uani 1 1 d . . . . .
H14A H 0.6313 0.5657 0.2450 0.101 Uiso 1 1 calc R U . . .
C3 C -0.0181(4) 0.2151(8) 0.08138(15) 0.0771(11) Uani 1 1 d . . . . .
F4A F -0.0465(9) 0.017(2) 0.1529(4) 0.122(3) Uani 0.7 1 d . . P A 1
F4B F -0.009(2) -0.058(5) 0.1376(8) 0.141(8) Uani 0.3 1 d . . P A 2
C15 C 0.6774(4) 0.2528(9) 0.22080(14) 0.0832(13) Uani 1 1 d . . . . .
H15A H 0.7502 0.2178 0.2447 0.100 Uiso 1 1 calc R U . . .
C4 C 0.0063(4) 0.1940(9) 0.13383(17) 0.0903(13) Uani 1 1 d . . . . .
F5 F -0.0647(3) 0.3670(8) 0.15213(12) 0.1501(14) Uani 1 1 d . . . . .
F3 F -0.0481(3) 0.0023(5) 0.06158(11) 0.1188(10) 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
F1 C2 1.344(4) . ?
N1 C1 1.368(4) . ?
N1 C6 1.436(4) . ?
N1 C12 1.453(4) . ?
C6 C7 1.376(4) . ?
C6 C11 1.381(4) . ?
C9 C8 1.392(4) . ?
C9 C10 1.395(4) . ?
C9 C9 1.476(5) 3_675 ?
C8 C7 1.385(4) . ?
C8 H8A 0.9300 . ?
C7 H7A 0.9300 . ?
C11 C10 1.379(4) . ?
C11 H11A 0.9300 . ?
F2 C3 1.341(4) . ?
F6 C5 1.324(4) . ?
C12 C13 1.377(4) . ?
C12 C17 1.378(5) . ?
C10 H10A 0.9300 . ?
F7 C5 1.361(5) . ?
C1 C2 1.340(4) . ?
C1 C5 1.502(4) . ?
C2 C3 1.456(5) . ?
C17 C16 1.403(5) . ?
C17 H17A 0.9300 . ?
C13 C14 1.386(5) . ?
C13 H13A 0.9300 . ?
C5 C4 1.539(5) . ?
C16 C15 1.378(6) . ?
C16 H16A 0.9300 . ?
C14 C15 1.369(6) . ?
C14 H14A 0.9300 . ?
C3 F3 1.363(5) . ?
C3 C4 1.519(6) . ?
F4A C4 1.298(11) . ?
F4B C4 1.46(3) . ?
C15 H15A 0.9300 . ?
C4 F5 1.355(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
C1 N1 C6 122.4(2) . . ?
C1 N1 C12 120.8(2) . . ?
C6 N1 C12 116.8(2) . . ?
C7 C6 C11 118.7(3) . . ?
C7 C6 N1 121.5(3) . . ?
C11 C6 N1 119.7(3) . . ?
C8 C9 C10 116.0(3) . . ?
C8 C9 C9 121.4(3) . 3_675 ?
C10 C9 C9 122.6(3) . 3_675 ?
C7 C8 C9 121.9(3) . . ?
C7 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
C13 C12 C17 121.1(3) . . ?
C13 C12 N1 118.8(3) . . ?
C17 C12 N1 120.1(3) . . ?
C11 C10 C9 122.4(3) . . ?
C11 C10 H10A 118.8 . . ?
C9 C10 H10A 118.8 . . ?
C2 C1 N1 131.4(3) . . ?
C2 C1 C5 107.8(3) . . ?
N1 C1 C5 120.8(3) . . ?
C1 C2 F1 126.7(3) . . ?
C1 C2 C3 116.6(3) . . ?
F1 C2 C3 116.7(3) . . ?
C12 C17 C16 118.6(3) . . ?
C12 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
F6 C5 F7 105.4(3) . . ?
F6 C5 C1 113.7(3) . . ?
F7 C5 C1 112.3(3) . . ?
F6 C5 C4 112.1(3) . . ?
F7 C5 C4 109.0(3) . . ?
C1 C5 C4 104.4(3) . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
F2 C3 F3 104.3(3) . . ?
F2 C3 C2 114.1(3) . . ?
F3 C3 C2 113.0(3) . . ?
F2 C3 C4 112.9(4) . . ?
F3 C3 C4 110.3(4) . . ?
C2 C3 C4 102.4(3) . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
F4A C4 F5 99.0(5) . . ?
F5 C4 F4B 129.3(9) . . ?
F4A C4 C3 119.0(6) . . ?
F5 C4 C3 109.2(4) . . ?
F4B C4 C3 98.8(10) . . ?
F4A C4 C5 114.2(6) . . ?
F5 C4 C5 107.9(4) . . ?
F4B C4 C5 102.9(10) . . ?
C3 C4 C5 106.9(3) . . ?

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
C1 N1 C6 C7 34.1(4) . . . . ?
C12 N1 C6 C7 -144.8(3) . . . . ?
C1 N1 C6 C11 -148.6(3) . . . . ?
C12 N1 C6 C11 32.5(4) . . . . ?
C10 C9 C8 C7 -0.2(5) . . . . ?
C9 C9 C8 C7 179.8(3) 3_675 . . . ?
C11 C6 C7 C8 0.8(5) . . . . ?
N1 C6 C7 C8 178.1(3) . . . . ?
C9 C8 C7 C6 -0.4(5) . . . . ?
C7 C6 C11 C10 -0.6(5) . . . . ?
N1 C6 C11 C10 -177.9(3) . . . . ?
C1 N1 C12 C13 -103.7(4) . . . . ?
C6 N1 C12 C13 75.2(4) . . . . ?
C1 N1 C12 C17 79.3(4) . . . . ?
C6 N1 C12 C17 -101.8(3) . . . . ?
C6 C11 C10 C9 -0.1(6) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C9 C10 C11 -179.6(4) 3_675 . . . ?
C6 N1 C1 C2 22.4(5) . . . . ?
C12 N1 C1 C2 -158.8(3) . . . . ?
C6 N1 C1 C5 -158.6(3) . . . . ?
C12 N1 C1 C5 20.3(5) . . . . ?
N1 C1 C2 F1 3.5(6) . . . . ?
C5 C1 C2 F1 -175.6(3) . . . . ?
N1 C1 C2 C3 -177.2(3) . . . . ?
C5 C1 C2 C3 3.6(4) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
N1 C12 C17 C16 176.4(3) . . . . ?
C17 C12 C13 C14 0.4(5) . . . . ?
N1 C12 C13 C14 -176.5(3) . . . . ?
C2 C1 C5 F6 -133.3(3) . . . . ?
N1 C1 C5 F6 47.4(5) . . . . ?
C2 C1 C5 F7 107.1(3) . . . . ?
N1 C1 C5 F7 -72.1(4) . . . . ?
C2 C1 C5 C4 -10.8(4) . . . . ?
N1 C1 C5 C4 169.9(3) . . . . ?
C12 C17 C16 C15 0.4(5) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C1 C2 C3 F2 127.8(4) . . . . ?
F1 C2 C3 F2 -52.9(5) . . . . ?
C1 C2 C3 F3 -113.3(4) . . . . ?
F1 C2 C3 F3 66.0(4) . . . . ?
C1 C2 C3 C4 5.4(5) . . . . ?
F1 C2 C3 C4 -175.3(3) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C17 C16 C15 C14 -0.2(6) . . . . ?
F2 C3 C4 F4A 93.9(7) . . . . ?
F3 C3 C4 F4A -22.3(7) . . . . ?
C2 C3 C4 F4A -142.9(6) . . . . ?
F2 C3 C4 F5 -18.5(5) . . . . ?
F3 C3 C4 F5 -134.8(4) . . . . ?
C2 C3 C4 F5 104.6(4) . . . . ?
F2 C3 C4 F4B 118.6(9) . . . . ?
F3 C3 C4 F4B 2.4(10) . . . . ?
C2 C3 C4 F4B -118.2(9) . . . . ?
F2 C3 C4 C5 -134.9(4) . . . . ?
F3 C3 C4 C5 108.8(4) . . . . ?
C2 C3 C4 C5 -11.8(5) . . . . ?
F6 C5 C4 F4A -88.7(7) . . . . ?
F7 C5 C4 F4A 27.6(7) . . . . ?
C1 C5 C4 F4A 147.8(6) . . . . ?
F6 C5 C4 F5 20.2(5) . . . . ?
F7 C5 C4 F5 136.5(4) . . . . ?
C1 C5 C4 F5 -103.3(4) . . . . ?
F6 C5 C4 F4B -118.9(10) . . . . ?
F7 C5 C4 F4B -2.6(10) . . . . ?
C1 C5 C4 F4B 117.5(10) . . . . ?
F6 C5 C4 C3 137.5(4) . . . . ?
F7 C5 C4 C3 -106.2(4) . . . . ?
C1 C5 C4 C3 14.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A F1 0.93 2.54 3.341(4) 144.8 1_565

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.049

