# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1480697'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        
"9,9'-(1,2-ethanediyl)bis-9H-purin-6-amine tetra-1,1,1,3,3,3-hexafluoro-2-propanol solvate"
_chemical_name_common            ethylene-9,9'-diadenine
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N10, 4(C3 H2 F6 O)'
_chemical_formula_sum            'C24 H20 F24 N10 O4'
_chemical_formula_weight         968.5

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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.1752(7)
_cell_length_b                   10.3078(10)
_cell_length_c                   12.3995(12)
_cell_angle_alpha                86.613(2)
_cell_angle_beta                 87.488(2)
_cell_angle_gamma                71.906(2)
_cell_volume                     869.89(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18906
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.64

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_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_method       
'Sets of exposures each taken over 0.5° ω rotation'
_diffrn_measurement_device_type  'Bruker D8 Advance single crystal CCD'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            21096
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         29.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4878
_reflns_number_gt                3936
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.4485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4878
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
N1 N 0.92967(15) 0.34004(10) 0.53002(8) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.92398(18) 0.22507(13) 0.58379(10) 0.0158(2) Uani 1 1 d . . . . .
H2 H 1.022(2) 0.1885(16) 0.6341(13) 0.019 Uiso 1 1 d . U . . .
N3 N 0.79782(15) 0.15486(10) 0.57514(8) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.65722(17) 0.21849(12) 0.50458(9) 0.0133(2) Uani 1 1 d . . . . .
C5 C 0.64437(17) 0.33707(12) 0.44320(9) 0.0138(2) Uani 1 1 d . . . . .
C6 C 0.79239(17) 0.39835(12) 0.45501(9) 0.0142(2) Uani 1 1 d . . . . .
N7 N 0.47846(15) 0.37354(10) 0.38085(8) 0.0149(2) Uani 1 1 d . . . . .
C8 C 0.39489(18) 0.27878(12) 0.40537(10) 0.0155(2) Uani 1 1 d . . . . .
H8 H 0.277(2) 0.2735(15) 0.3773(12) 0.017(4) Uiso 1 1 d . . . . .
N9 N 0.49609(15) 0.18179(10) 0.47996(8) 0.0144(2) Uani 1 1 d . . . . .
N10 N 0.80337(17) 0.50932(11) 0.39766(9) 0.0179(2) Uani 1 1 d . . . . .
H10 H 0.888(2) 0.5457(16) 0.4122(13) 0.018(4) Uiso 1 1 d . . . . .
H11 H 0.719(3) 0.5462(18) 0.3501(14) 0.027(4) Uiso 1 1 d . . . . .
C11 C 0.44133(18) 0.06534(12) 0.52697(10) 0.0155(2) Uani 1 1 d . . . . .
H12 H 0.304(2) 0.0816(15) 0.5151(12) 0.015(4) Uiso 1 1 d . . . . .
H13 H 0.462(2) 0.0566(15) 0.6020(12) 0.015(4) Uiso 1 1 d . . . . .
O1B O 0.88411(15) -0.09848(10) 0.67281(7) 0.0218(2) Uani 1 1 d . . . . .
H1B H 0.856(3) -0.019(2) 0.6381(16) 0.043(5) Uiso 1 1 d . . . . .
C1B C 1.11855(19) -0.11919(14) 0.80887(11) 0.0216(3) Uani 1 1 d . . . . .
C2B C 0.90224(18) -0.07704(12) 0.78151(10) 0.0166(2) Uani 1 1 d . . . . .
H21B H 0.851(2) 0.0156(15) 0.7978(12) 0.012(3) Uiso 1 1 d . . . . .
C3B C 0.7874(2) -0.15492(14) 0.84977(11) 0.0216(3) Uani 1 1 d . . . . .
F1B F 1.21006(13) -0.25185(9) 0.79837(7) 0.0328(2) Uani 1 1 d . . . . .
F2B F 1.14607(12) -0.08916(10) 0.90840(7) 0.0306(2) Uani 1 1 d . . . . .
F3B F 1.20967(13) -0.05116(11) 0.74004(8) 0.0361(2) Uani 1 1 d . . . . .
F4B F 0.59772(12) -0.10607(10) 0.82561(8) 0.0345(2) Uani 1 1 d . . . . .
F5B F 0.80150(14) -0.14299(10) 0.95494(7) 0.0333(2) Uani 1 1 d . . . . .
F6B F 0.84499(14) -0.28752(8) 0.83102(7) 0.0333(2) Uani 1 1 d . . . . .
O1C O 0.42937(14) 0.60850(9) 0.26997(7) 0.01872(19) Uani 1 1 d . . . . .
H1C H 0.429(3) 0.533(2) 0.3053(18) 0.053(6) Uiso 1 1 d . . . . .
C1C C 0.52762(19) 0.68188(13) 0.10009(11) 0.0209(3) Uani 1 1 d . . . . .
C2C C 0.41571(18) 0.59465(12) 0.15970(10) 0.0165(2) Uani 1 1 d . . . . .
H2C H 0.474(2) 0.5026(16) 0.1374(12) 0.016(4) Uiso 1 1 d . . . . .
C3C C 0.20044(19) 0.63477(13) 0.12935(10) 0.0195(3) Uani 1 1 d . . . . .
F1C F 0.46448(13) 0.81166(8) 0.12750(7) 0.0292(2) Uani 1 1 d . . . . .
F2C F 0.51487(13) 0.68097(9) -0.00677(7) 0.0308(2) Uani 1 1 d . . . . .
F3C F 0.71692(12) 0.63329(9) 0.12393(8) 0.0323(2) Uani 1 1 d . . . . .
F4C F 0.11022(13) 0.56288(9) 0.19347(7) 0.0309(2) Uani 1 1 d . . . . .
F5C F 0.17920(13) 0.60916(9) 0.02749(7) 0.0312(2) Uani 1 1 d . . . . .
F6C F 0.10425(12) 0.76684(8) 0.14274(7) 0.02459(18) 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
N1 C2 1.3360(15) . ?
N1 C6 1.3576(15) . ?
C2 N3 1.3339(16) . ?
C2 H2 0.935(16) . ?
N3 C4 1.3461(15) . ?
C4 N9 1.3745(15) . ?
C4 C5 1.3813(16) . ?
C5 N7 1.3873(15) . ?
C5 C6 1.4105(16) . ?
C6 N10 1.3324(15) . ?
N7 C8 1.3110(15) . ?
C8 N9 1.3715(15) . ?
C8 H8 0.948(15) . ?
N9 C11 1.4577(15) . ?
N10 H10 0.840(17) . ?
N10 H11 0.850(18) . ?
C11 C11 1.524(2) 2_656 ?
C11 H12 0.965(15) . ?
C11 H13 0.944(15) . ?
O1B C2B 1.3966(15) . ?
O1B H1B 0.87(2) . ?
C1B F2B 1.3274(15) . ?
C1B F1B 1.3319(16) . ?
C1B F3B 1.3464(16) . ?
C1B C2B 1.5240(18) . ?
C2B C3B 1.5198(18) . ?
C2B H21B 0.942(15) . ?
C3B F5B 1.3282(16) . ?
C3B F6B 1.3309(16) . ?
C3B F4B 1.3369(16) . ?
O1C C2C 1.3938(15) . ?
O1C H1C 0.87(2) . ?
C1C F1C 1.3320(15) . ?
C1C F2C 1.3329(16) . ?
C1C F3C 1.3336(15) . ?
C1C C2C 1.5223(18) . ?
C2C C3C 1.5278(18) . ?
C2C H2C 0.962(15) . ?
C3C F5C 1.3301(15) . ?
C3C F4C 1.3355(15) . ?
C3C F6C 1.3380(15) . ?

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 C6 118.86(10) . . ?
N3 C2 N1 128.86(11) . . ?
N3 C2 H2 115.5(9) . . ?
N1 C2 H2 115.7(10) . . ?
C2 N3 C4 111.13(10) . . ?
N3 C4 N9 127.79(10) . . ?
N3 C4 C5 126.40(11) . . ?
N9 C4 C5 105.80(10) . . ?
C4 C5 N7 110.31(10) . . ?
C4 C5 C6 117.31(11) . . ?
N7 C5 C6 132.38(11) . . ?
N10 C6 N1 118.94(11) . . ?
N10 C6 C5 123.80(11) . . ?
N1 C6 C5 117.25(10) . . ?
C8 N7 C5 104.61(10) . . ?
N7 C8 N9 112.99(11) . . ?
N7 C8 H8 126.5(9) . . ?
N9 C8 H8 120.5(9) . . ?
C8 N9 C4 106.30(10) . . ?
C8 N9 C11 127.16(10) . . ?
C4 N9 C11 126.50(10) . . ?
C6 N10 H10 119.6(11) . . ?
C6 N10 H11 119.6(12) . . ?
H10 N10 H11 120.6(16) . . ?
N9 C11 C11 110.57(12) . 2_656 ?
N9 C11 H12 108.3(9) . . ?
C11 C11 H12 108.7(9) 2_656 . ?
N9 C11 H13 109.7(9) . . ?
C11 C11 H13 110.4(9) 2_656 . ?
H12 C11 H13 109.1(13) . . ?
C2B O1B H1B 107.2(13) . . ?
F2B C1B F1B 107.88(11) . . ?
F2B C1B F3B 107.51(11) . . ?
F1B C1B F3B 106.79(11) . . ?
F2B C1B C2B 112.52(11) . . ?
F1B C1B C2B 113.15(11) . . ?
F3B C1B C2B 108.70(10) . . ?
O1B C2B C3B 108.41(10) . . ?
O1B C2B C1B 109.65(11) . . ?
C3B C2B C1B 113.17(11) . . ?
O1B C2B H21B 112.7(9) . . ?
C3B C2B H21B 107.3(9) . . ?
C1B C2B H21B 105.7(9) . . ?
F5B C3B F6B 107.82(11) . . ?
F5B C3B F4B 107.88(11) . . ?
F6B C3B F4B 106.76(11) . . ?
F5B C3B C2B 112.29(11) . . ?
F6B C3B C2B 112.47(11) . . ?
F4B C3B C2B 109.37(11) . . ?
C2C O1C H1C 109.6(14) . . ?
F1C C1C F2C 107.64(11) . . ?
F1C C1C F3C 107.10(11) . . ?
F2C C1C F3C 107.76(11) . . ?
F1C C1C C2C 112.66(11) . . ?
F2C C1C C2C 111.88(11) . . ?
F3C C1C C2C 109.57(11) . . ?
O1C C2C C1C 107.25(10) . . ?
O1C C2C C3C 109.96(10) . . ?
C1C C2C C3C 113.29(10) . . ?
O1C C2C H2C 113.7(9) . . ?
C1C C2C H2C 107.1(9) . . ?
C3C C2C H2C 105.7(9) . . ?
F5C C3C F4C 107.98(11) . . ?
F5C C3C F6C 107.62(10) . . ?
F4C C3C F6C 106.81(11) . . ?
F5C C3C C2C 112.32(11) . . ?
F4C C3C C2C 108.85(10) . . ?
F6C C3C C2C 113.00(10) . . ?

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 N1 C2 N3 -0.1(2) . . . . ?
N1 C2 N3 C4 -3.16(18) . . . . ?
C2 N3 C4 N9 -175.50(12) . . . . ?
C2 N3 C4 C5 3.12(17) . . . . ?
N3 C4 C5 N7 -179.15(11) . . . . ?
N9 C4 C5 N7 -0.28(13) . . . . ?
N3 C4 C5 C6 0.00(18) . . . . ?
N9 C4 C5 C6 178.86(10) . . . . ?
C2 N1 C6 N10 -176.82(11) . . . . ?
C2 N1 C6 C5 3.59(16) . . . . ?
C4 C5 C6 N10 176.95(12) . . . . ?
N7 C5 C6 N10 -4.1(2) . . . . ?
C4 C5 C6 N1 -3.49(17) . . . . ?
N7 C5 C6 N1 175.43(12) . . . . ?
C4 C5 N7 C8 0.28(13) . . . . ?
C6 C5 N7 C8 -178.70(13) . . . . ?
C5 N7 C8 N9 -0.17(14) . . . . ?
N7 C8 N9 C4 0.00(14) . . . . ?
N7 C8 N9 C11 178.08(11) . . . . ?
N3 C4 N9 C8 179.02(12) . . . . ?
C5 C4 N9 C8 0.17(13) . . . . ?
N3 C4 N9 C11 0.92(19) . . . . ?
C5 C4 N9 C11 -177.93(11) . . . . ?
C8 N9 C11 C11 101.44(16) . . . 2_656 ?
C4 N9 C11 C11 -80.84(17) . . . 2_656 ?
F2B C1B C2B O1B 173.99(10) . . . . ?
F1B C1B C2B O1B -63.41(14) . . . . ?
F3B C1B C2B O1B 55.04(14) . . . . ?
F2B C1B C2B C3B -64.84(15) . . . . ?
F1B C1B C2B C3B 57.76(15) . . . . ?
F3B C1B C2B C3B 176.21(11) . . . . ?
O1B C2B C3B F5B 178.25(10) . . . . ?
C1B C2B C3B F5B 56.38(15) . . . . ?
O1B C2B C3B F6B 56.41(14) . . . . ?
C1B C2B C3B F6B -65.45(15) . . . . ?
O1B C2B C3B F4B -62.03(14) . . . . ?
C1B C2B C3B F4B 176.11(11) . . . . ?
F1C C1C C2C O1C -55.39(14) . . . . ?
F2C C1C C2C O1C -176.83(10) . . . . ?
F3C C1C C2C O1C 63.73(13) . . . . ?
F1C C1C C2C C3C 66.13(14) . . . . ?
F2C C1C C2C C3C -55.31(15) . . . . ?
F3C C1C C2C C3C -174.75(10) . . . . ?
O1C C2C C3C F5C -173.09(10) . . . . ?
C1C C2C C3C F5C 66.92(14) . . . . ?
O1C C2C C3C F4C -53.57(13) . . . . ?
C1C C2C C3C F4C -173.56(10) . . . . ?
O1C C2C C3C F6C 64.92(13) . . . . ?
C1C C2C C3C F6C -55.07(15) . . . . ?

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
N10 H10 N1 0.840(17) 2.177(17) 3.0078(15) 170.0(15) 2_766
N10 H11 O1C 0.850(18) 2.233(18) 3.0382(15) 158.1(16) .
O1B H1B N3 0.87(2) 1.84(2) 2.7124(14) 175.5(19) .
O1C H1C N7 0.87(2) 1.79(2) 2.6456(14) 169(2) .

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 'Vapour diffusion'
####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 1480698'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        
;
9-methyladenine di-1,1,1,3,3,3-hexafluoro-2-propanol solvate
;
_chemical_name_common            
;
9-methyladenine dihexafluoro-2-propanol solvate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N5, 2(C3 H2 F6 O)'
_chemical_formula_sum            'C12 H11 F12 N5 O2'
_chemical_formula_weight         485.26

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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   12.150(3)
_cell_length_b                   12.921(3)
_cell_length_c                   13.546(3)
_cell_angle_alpha                113.938(5)
_cell_angle_beta                 101.075(6)
_cell_angle_gamma                96.166(6)
_cell_volume                     1866.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9507
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.65

_exptl_crystal_description       'elongated plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
Crystals decay within seconds after removal from the mother liquor.
A selected specimen was shock-frozen in N2(l) prior to data collection.
;

_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_method       
'Sets of exposures each taken over 0.5° ω rotation'
_diffrn_measurement_device_type  'Bruker D8 Advance single crystal CCD'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            25822
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.099
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6581
_reflns_number_gt                4445
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0369P)²+1.7887P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6581
_refine_ls_number_parameters     573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N1A N 0.48653(19) 0.19091(18) 0.09419(18) 0.0181(5) Uani 1 1 d . . . . .
C2A C 0.4503(2) 0.1754(2) -0.0115(2) 0.0209(7) Uani 1 1 d . . . . .
H2A H 0.3835 0.2039 -0.0276 0.025 Uiso 1 1 calc R U . . .
N3A N 0.49511(19) 0.12555(19) -0.09697(18) 0.0204(5) Uani 1 1 d . . . . .
C4A C 0.5884(2) 0.0872(2) -0.0666(2) 0.0173(6) Uani 1 1 d . . . . .
C5A C 0.6354(2) 0.0975(2) 0.0388(2) 0.0177(6) Uani 1 1 d . . . . .
C6A C 0.5822(2) 0.1533(2) 0.1234(2) 0.0172(6) Uani 1 1 d . . . . .
N7A N 0.73107(19) 0.04807(19) 0.04007(18) 0.0202(5) Uani 1 1 d . . . . .
C8A C 0.7390(2) 0.0094(2) -0.0636(2) 0.0206(7) Uani 1 1 d . . . . .
H8A H 0.7975 -0.0294 -0.0886 0.025 Uiso 1 1 calc R U . . .
N9A N 0.65565(19) 0.03019(19) -0.13208(18) 0.0185(5) Uani 1 1 d . . . . .
N10A N 0.61906(19) 0.1712(2) 0.22895(18) 0.0222(6) Uani 1 1 d . . . . .
H10A H 0.5816 0.2068 0.2781 0.027 Uiso 1 1 calc R U . . .
H11A H 0.6809 0.1476 0.2497 0.027 Uiso 1 1 calc R U . . .
C11A C 0.6402(3) -0.0034(2) -0.2513(2) 0.0248(7) Uani 1 1 d . . . . .
H12A H 0.7105 -0.0237 -0.2722 0.037 Uiso 1 1 calc R U . . .
H13A H 0.6231 0.0614 -0.2676 0.037 Uiso 1 1 calc R U . . .
H14A H 0.5764 -0.0703 -0.2943 0.037 Uiso 1 1 calc R U . . .
N1B N 0.50194(19) 0.29918(19) 0.39685(18) 0.0182(5) Uani 1 1 d . . . . .
C2B C 0.5505(2) 0.3361(2) 0.5061(2) 0.0194(6) Uani 1 1 d . . . . .
H2B H 0.6219 0.3155 0.5238 0.023 Uiso 1 1 calc R U . . .
N3B N 0.51245(19) 0.39739(18) 0.59263(18) 0.0183(5) Uani 1 1 d . . . . .
C4B C 0.4105(2) 0.4220(2) 0.5600(2) 0.0171(6) Uani 1 1 d . . . . .
C5B C 0.3504(2) 0.3897(2) 0.4504(2) 0.0181(6) Uani 1 1 d . . . . .
C6B C 0.3992(2) 0.3251(2) 0.3659(2) 0.0185(6) Uani 1 1 d . . . . .
N7B N 0.25042(19) 0.43215(19) 0.44843(19) 0.0209(6) Uani 1 1 d . . . . .
C8B C 0.2518(2) 0.4864(2) 0.5546(2) 0.0219(7) Uani 1 1 d . . . . .
H8B H 0.1925 0.5238 0.5794 0.026 Uiso 1 1 calc R U . . .
N9B N 0.34653(19) 0.48377(18) 0.62546(18) 0.0182(5) Uani 1 1 d . . . . .
N10B N 0.3512(2) 0.2876(2) 0.25731(18) 0.0241(6) Uani 1 1 d . . . . .
H10B H 0.3859 0.2472 0.2076 0.029 Uiso 1 1 calc R U . . .
H11B H 0.2847 0.3033 0.2351 0.029 Uiso 1 1 calc R U . . .
C11B C 0.3708(3) 0.5302(3) 0.7471(2) 0.0272(7) Uani 1 1 d . . . . .
H12B H 0.3163 0.5790 0.7735 0.041 Uiso 1 1 calc R U . . .
H13B H 0.4490 0.5767 0.7810 0.041 Uiso 1 1 calc R U . . .
H14B H 0.3634 0.4663 0.7683 0.041 Uiso 1 1 calc R U . . .
O1C O 0.42425(18) 0.17940(19) -0.26908(17) 0.0354(6) Uani 1 1 d . . . . .
H1C H 0.445(3) 0.155(3) -0.218(3) 0.053 Uiso 1 1 d . U . . .
C1C C 0.2348(3) 0.1886(3) -0.3430(3) 0.0350(8) Uani 1 1 d . . . . .
C2C C 0.3174(2) 0.1113(2) -0.3402(2) 0.0237(7) Uani 1 1 d . . . . .
H2C H 0.2882 0.0578 -0.3102 0.028 Uiso 1 1 calc R U . . .
C3C C 0.3365(3) 0.0405(3) -0.4533(3) 0.0381(9) Uani 1 1 d . . . . .
F1C F 0.2274(2) 0.25337(19) -0.24108(18) 0.0720(7) Uani 1 1 d . . . . .
F2C F 0.12930(15) 0.12906(16) -0.40415(17) 0.0460(5) Uani 1 1 d . . . . .
F3C F 0.26535(17) 0.26019(17) -0.38593(19) 0.0573(6) Uani 1 1 d . . . . .
F4C F 0.39329(18) 0.1044(2) -0.49056(16) 0.0617(7) Uani 1 1 d . . . . .
F5C F 0.23818(16) -0.01685(16) -0.53191(14) 0.0444(5) Uani 1 1 d . . . . .
F6C F 0.39576(19) -0.0382(2) -0.44769(18) 0.0685(7) Uani 1 1 d . . . . .
O1D O 0.82617(16) 0.05604(17) 0.23894(16) 0.0240(5) Uani 1 1 d . . . . .
H1D H 0.812(3) 0.052(3) 0.178(3) 0.036 Uiso 1 1 d . U . . .
C1D C 0.9331(3) 0.2064(3) 0.4098(3) 0.0288(7) Uani 1 1 d . . . . .
C2D C 0.9346(2) 0.1319(2) 0.2910(2) 0.0221(7) Uani 1 1 d . . . . .
H2D H 0.9449 0.1821 0.2521 0.027 Uiso 1 1 calc R U . . .
C3D C 1.0271(3) 0.0619(3) 0.2823(3) 0.0315(8) Uani 1 1 d . . . . .
F1D F 0.85309(16) 0.27021(16) 0.41001(15) 0.0481(6) Uani 1 1 d . . . . .
F2D F 1.03312(15) 0.28069(16) 0.46889(15) 0.0443(5) Uani 1 1 d . . . . .
F3D F 0.90939(16) 0.14703(16) 0.46523(14) 0.0402(5) Uani 1 1 d . . . . .
F4D F 1.01666(15) -0.01250(16) 0.32487(16) 0.0435(5) Uani 1 1 d . . . . .
F5D F 1.13222(14) 0.13001(17) 0.33293(17) 0.0456(5) Uani 1 1 d . . . . .
F6D F 1.02455(17) 0.00268(18) 0.17488(16) 0.0513(6) Uani 1 1 d . . . . .
O1E O 0.67861(17) 0.47949(17) 0.78345(17) 0.0272(5) Uani 1 1 d . . . . .
H1E H 0.627(3) 0.464(3) 0.728(3) 0.041 Uiso 1 1 d . U . . .
C1E C 0.7457(3) 0.3306(3) 0.8193(3) 0.0350(8) Uani 1 1 d . . . . .
C2E C 0.6596(3) 0.4078(3) 0.8351(2) 0.0257(7) Uani 1 1 d . . . . .
H2E H 0.5807 0.3585 0.7985 0.031 Uiso 1 1 calc R U . . .
C3E C 0.6676(3) 0.4833(3) 0.9560(3) 0.0357(8) Uani 1 1 d . . . . .
F1E F 0.72529(19) 0.25803(17) 0.71110(16) 0.0551(6) Uani 1 1 d . . . . .
F2E F 0.74116(17) 0.26577(15) 0.87502(16) 0.0453(5) Uani 1 1 d . . . . .
F3E F 0.85359(15) 0.38958(16) 0.85189(17) 0.0442(5) Uani 1 1 d . . . . .
F4E F 0.77011(17) 0.55221(17) 1.01072(15) 0.0505(6) Uani 1 1 d . . . . .
F5E F 0.64579(19) 0.42144(18) 1.01101(16) 0.0544(6) Uani 1 1 d . . . . .
F6E F 0.59119(18) 0.55122(18) 0.96371(17) 0.0538(6) Uani 1 1 d . . . . .
O1F O 0.09455(18) 0.31973(18) 0.25123(17) 0.0282(5) Uani 1 1 d . . . . .
H1F H 0.127(3) 0.363(3) 0.311(3) 0.042 Uiso 1 1 d . U . . .
C1F C 0.0452(3) 0.2839(3) 0.0646(3) 0.0379(9) Uani 1 1 d . . . . .
C2F C 0.0621(2) 0.3737(3) 0.1835(2) 0.0248(7) Uani 1 1 d . . . . .
H2F H 0.1259 0.4392 0.2008 0.030 Uiso 1 1 calc R U . . .
C3F C -0.0434(3) 0.4206(3) 0.2045(3) 0.0425(9) Uani 1 1 d . . . . .
F1F F 0.14371(16) 0.24962(17) 0.05090(15) 0.0467(5) Uani 1 1 d . . . . .
F2F F 0.01103(17) 0.3217(2) -0.01019(17) 0.0655(7) Uani 1 1 d . . . . .
F3F F -0.03147(18) 0.18893(18) 0.04065(16) 0.0616(7) Uani 1 1 d . . . . .
F4F F -0.13257(16) 0.33783(19) 0.18710(19) 0.0579(6) Uani 1 1 d . . . . .
F5F F -0.07855(17) 0.4731(2) 0.1424(2) 0.0670(7) Uani 1 1 d . . . . .
F6F F -0.02213(19) 0.49630(19) 0.3117(2) 0.0649(7) 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
N1A C2A 1.338(3) . ?
N1A C6A 1.358(3) . ?
C2A N3A 1.328(4) . ?
C2A H2A 0.9500 . ?
N3A C4A 1.344(3) . ?
C4A N9A 1.369(3) . ?
C4A C5A 1.378(4) . ?
C5A N7A 1.386(3) . ?
C5A C6A 1.401(4) . ?
C6A N10A 1.328(3) . ?
N7A C8A 1.313(3) . ?
C8A N9A 1.363(3) . ?
C8A H8A 0.9500 . ?
N9A C11A 1.460(3) . ?
N10A H10A 0.8800 . ?
N10A H11A 0.8800 . ?
C11A H12A 0.9800 . ?
C11A H13A 0.9800 . ?
C11A H14A 0.9800 . ?
N1B C2B 1.341(3) . ?
N1B C6B 1.360(3) . ?
C2B N3B 1.322(3) . ?
C2B H2B 0.9500 . ?
N3B C4B 1.349(3) . ?
C4B N9B 1.360(3) . ?
C4B C5B 1.388(4) . ?
C5B N7B 1.386(3) . ?
C5B C6B 1.397(4) . ?
C6B N10B 1.330(3) . ?
N7B C8B 1.315(3) . ?
C8B N9B 1.363(3) . ?
C8B H8B 0.9500 . ?
N9B C11B 1.461(3) . ?
N10B H10B 0.8800 . ?
N10B H11B 0.8800 . ?
C11B H12B 0.9800 . ?
C11B H13B 0.9800 . ?
C11B H14B 0.9800 . ?
O1C C2C 1.405(3) . ?
O1C H1C 0.87(4) . ?
C1C F1C 1.319(4) . ?
C1C F3C 1.333(4) . ?
C1C F2C 1.335(4) . ?
C1C C2C 1.496(4) . ?
C2C C3C 1.511(4) . ?
C2C H2C 1.0000 . ?
C3C F6C 1.325(4) . ?
C3C F4C 1.326(4) . ?
C3C F5C 1.338(3) . ?
O1D C2D 1.413(3) . ?
O1D H1D 0.79(3) . ?
C1D F3D 1.318(4) . ?
C1D F2D 1.338(3) . ?
C1D F1D 1.341(3) . ?
C1D C2D 1.509(4) . ?
C2D C3D 1.509(4) . ?
C2D H2D 1.0000 . ?
C3D F4D 1.314(4) . ?
C3D F6D 1.333(4) . ?
C3D F5D 1.345(3) . ?
O1E C2E 1.395(3) . ?
O1E H1E 0.82(3) . ?
C1E F3E 1.336(4) . ?
C1E F1E 1.336(4) . ?
C1E F2E 1.339(4) . ?
C1E C2E 1.506(4) . ?
C2E C3E 1.505(4) . ?
C2E H2E 1.0000 . ?
C3E F4E 1.329(4) . ?
C3E F5E 1.333(4) . ?
C3E F6E 1.335(4) . ?
O1F C2F 1.386(3) . ?
O1F H1F 0.77(3) . ?
C1F F2F 1.313(4) . ?
C1F F3F 1.339(4) . ?
C1F F1F 1.340(4) . ?
C1F C2F 1.512(4) . ?
C2F C3F 1.502(4) . ?
C2F H2F 1.0000 . ?
C3F F5F 1.319(4) . ?
C3F F6F 1.334(4) . ?
C3F F4F 1.350(4) . ?

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
C2A N1A C6A 118.8(2) . . ?
N3A C2A N1A 128.7(3) . . ?
N3A C2A H2A 115.7 . . ?
N1A C2A H2A 115.7 . . ?
C2A N3A C4A 111.4(2) . . ?
N3A C4A N9A 128.0(2) . . ?
N3A C4A C5A 126.1(3) . . ?
N9A C4A C5A 105.9(2) . . ?
C4A C5A N7A 110.6(2) . . ?
C4A C5A C6A 117.8(2) . . ?
N7A C5A C6A 131.6(2) . . ?
N10A C6A N1A 118.4(2) . . ?
N10A C6A C5A 124.4(2) . . ?
N1A C6A C5A 117.2(2) . . ?
C8A N7A C5A 103.6(2) . . ?
N7A C8A N9A 113.8(3) . . ?
N7A C8A H8A 123.1 . . ?
N9A C8A H8A 123.1 . . ?
C8A N9A C4A 106.0(2) . . ?
C8A N9A C11A 127.0(2) . . ?
C4A N9A C11A 127.1(2) . . ?
C6A N10A H10A 120.0 . . ?
C6A N10A H11A 120.0 . . ?
H10A N10A H11A 120.0 . . ?
N9A C11A H12A 109.5 . . ?
N9A C11A H13A 109.5 . . ?
H12A C11A H13A 109.5 . . ?
N9A C11A H14A 109.5 . . ?
H12A C11A H14A 109.5 . . ?
H13A C11A H14A 109.5 . . ?
C2B N1B C6B 118.6(2) . . ?
N3B C2B N1B 128.8(3) . . ?
N3B C2B H2B 115.6 . . ?
N1B C2B H2B 115.6 . . ?
C2B N3B C4B 111.7(2) . . ?
N3B C4B N9B 128.1(2) . . ?
N3B C4B C5B 125.9(3) . . ?
N9B C4B C5B 106.0(2) . . ?
N7B C5B C4B 110.1(2) . . ?
N7B C5B C6B 132.6(2) . . ?
C4B C5B C6B 117.3(2) . . ?
N10B C6B N1B 118.3(2) . . ?
N10B C6B C5B 123.9(2) . . ?
N1B C6B C5B 117.8(2) . . ?
C8B N7B C5B 103.9(2) . . ?
N7B C8B N9B 113.5(2) . . ?
N7B C8B H8B 123.2 . . ?
N9B C8B H8B 123.2 . . ?
C4B N9B C8B 106.4(2) . . ?
C4B N9B C11B 126.5(2) . . ?
C8B N9B C11B 127.0(2) . . ?
C6B N10B H10B 120.0 . . ?
C6B N10B H11B 120.0 . . ?
H10B N10B H11B 120.0 . . ?
N9B C11B H12B 109.5 . . ?
N9B C11B H13B 109.5 . . ?
H12B C11B H13B 109.5 . . ?
N9B C11B H14B 109.5 . . ?
H12B C11B H14B 109.5 . . ?
H13B C11B H14B 109.5 . . ?
C2C O1C H1C 108(2) . . ?
F1C C1C F3C 107.1(3) . . ?
F1C C1C F2C 107.4(3) . . ?
F3C C1C F2C 106.4(3) . . ?
F1C C1C C2C 110.5(3) . . ?
F3C C1C C2C 112.8(3) . . ?
F2C C1C C2C 112.3(3) . . ?
O1C C2C C1C 109.1(2) . . ?
O1C C2C C3C 107.3(3) . . ?
C1C C2C C3C 113.5(3) . . ?
O1C C2C H2C 109.0 . . ?
C1C C2C H2C 109.0 . . ?
C3C C2C H2C 109.0 . . ?
F6C C3C F4C 108.0(3) . . ?
F6C C3C F5C 106.8(3) . . ?
F4C C3C F5C 106.6(3) . . ?
F6C C3C C2C 109.9(3) . . ?
F4C C3C C2C 112.8(3) . . ?
F5C C3C C2C 112.4(3) . . ?
C2D O1D H1D 103(2) . . ?
F3D C1D F2D 107.5(2) . . ?
F3D C1D F1D 106.9(3) . . ?
F2D C1D F1D 106.7(2) . . ?
F3D C1D C2D 113.8(3) . . ?
F2D C1D C2D 111.9(3) . . ?
F1D C1D C2D 109.6(2) . . ?
O1D C2D C3D 109.3(2) . . ?
O1D C2D C1D 106.4(2) . . ?
C3D C2D C1D 113.6(2) . . ?
O1D C2D H2D 109.2 . . ?
C3D C2D H2D 109.2 . . ?
C1D C2D H2D 109.2 . . ?
F4D C3D F6D 107.7(3) . . ?
F4D C3D F5D 107.5(2) . . ?
F6D C3D F5D 106.5(3) . . ?
F4D C3D C2D 113.8(3) . . ?
F6D C3D C2D 109.2(2) . . ?
F5D C3D C2D 111.8(3) . . ?
C2E O1E H1E 113(2) . . ?
F3E C1E F1E 107.0(3) . . ?
F3E C1E F2E 107.0(2) . . ?
F1E C1E F2E 107.0(3) . . ?
F3E C1E C2E 112.9(3) . . ?
F1E C1E C2E 109.7(3) . . ?
F2E C1E C2E 112.8(3) . . ?
O1E C2E C3E 108.1(2) . . ?
O1E C2E C1E 108.4(3) . . ?
C3E C2E C1E 113.3(2) . . ?
O1E C2E H2E 109.0 . . ?
C3E C2E H2E 109.0 . . ?
C1E C2E H2E 109.0 . . ?
F4E C3E F5E 107.3(3) . . ?
F4E C3E F6E 107.0(3) . . ?
F5E C3E F6E 107.2(3) . . ?
F4E C3E C2E 112.8(3) . . ?
F5E C3E C2E 112.1(3) . . ?
F6E C3E C2E 110.1(3) . . ?
C2F O1F H1F 113(3) . . ?
F2F C1F F3F 107.8(3) . . ?
F2F C1F F1F 107.7(3) . . ?
F3F C1F F1F 106.4(3) . . ?
F2F C1F C2F 113.2(3) . . ?
F3F C1F C2F 111.4(3) . . ?
F1F C1F C2F 110.0(2) . . ?
O1F C2F C3F 110.5(3) . . ?
O1F C2F C1F 106.1(2) . . ?
C3F C2F C1F 113.3(3) . . ?
O1F C2F H2F 109.0 . . ?
C3F C2F H2F 109.0 . . ?
C1F C2F H2F 109.0 . . ?
F5F C3F F6F 108.1(3) . . ?
F5F C3F F4F 107.3(3) . . ?
F6F C3F F4F 105.7(3) . . ?
F5F C3F C2F 113.3(3) . . ?
F6F C3F C2F 109.4(3) . . ?
F4F C3F C2F 112.6(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
C6A N1A C2A N3A 0.7(4) . . . . ?
N1A C2A N3A C4A 0.5(4) . . . . ?
C2A N3A C4A N9A 178.9(3) . . . . ?
C2A N3A C4A C5A -0.7(4) . . . . ?
N3A C4A C5A N7A 179.9(2) . . . . ?
N9A C4A C5A N7A 0.2(3) . . . . ?
N3A C4A C5A C6A -0.3(4) . . . . ?
N9A C4A C5A C6A -180.0(2) . . . . ?
C2A N1A C6A N10A 178.6(2) . . . . ?
C2A N1A C6A C5A -1.6(4) . . . . ?
C4A C5A C6A N10A -178.7(2) . . . . ?
N7A C5A C6A N10A 1.1(5) . . . . ?
C4A C5A C6A N1A 1.4(4) . . . . ?
N7A C5A C6A N1A -178.8(3) . . . . ?
C4A C5A N7A C8A -0.2(3) . . . . ?
C6A C5A N7A C8A -180.0(3) . . . . ?
C5A N7A C8A N9A 0.1(3) . . . . ?
N7A C8A N9A C4A 0.1(3) . . . . ?
N7A C8A N9A C11A -179.0(2) . . . . ?
N3A C4A N9A C8A -179.8(3) . . . . ?
C5A C4A N9A C8A -0.2(3) . . . . ?
N3A C4A N9A C11A -0.8(4) . . . . ?
C5A C4A N9A C11A 178.9(2) . . . . ?
C6B N1B C2B N3B -0.4(4) . . . . ?
N1B C2B N3B C4B 0.5(4) . . . . ?
C2B N3B C4B N9B -179.4(3) . . . . ?
C2B N3B C4B C5B -0.5(4) . . . . ?
N3B C4B C5B N7B -178.6(2) . . . . ?
N9B C4B C5B N7B 0.5(3) . . . . ?
N3B C4B C5B C6B 0.5(4) . . . . ?
N9B C4B C5B C6B 179.6(2) . . . . ?
C2B N1B C6B N10B -179.7(2) . . . . ?
C2B N1B C6B C5B 0.4(4) . . . . ?
N7B C5B C6B N10B -1.5(5) . . . . ?
C4B C5B C6B N10B 179.6(3) . . . . ?
N7B C5B C6B N1B 178.5(3) . . . . ?
C4B C5B C6B N1B -0.4(4) . . . . ?
C4B C5B N7B C8B -0.9(3) . . . . ?
C6B C5B N7B C8B -179.8(3) . . . . ?
C5B N7B C8B N9B 1.0(3) . . . . ?
N3B C4B N9B C8B 179.2(3) . . . . ?
C5B C4B N9B C8B 0.1(3) . . . . ?
N3B C4B N9B C11B -5.0(4) . . . . ?
C5B C4B N9B C11B 175.9(3) . . . . ?
N7B C8B N9B C4B -0.7(3) . . . . ?
N7B C8B N9B C11B -176.5(3) . . . . ?
F1C C1C C2C O1C -56.4(3) . . . . ?
F3C C1C C2C O1C 63.4(3) . . . . ?
F2C C1C C2C O1C -176.3(2) . . . . ?
F1C C1C C2C C3C -175.9(3) . . . . ?
F3C C1C C2C C3C -56.1(4) . . . . ?
F2C C1C C2C C3C 64.1(4) . . . . ?
O1C C2C C3C F6C 69.2(3) . . . . ?
C1C C2C C3C F6C -170.2(3) . . . . ?
O1C C2C C3C F4C -51.4(3) . . . . ?
C1C C2C C3C F4C 69.2(3) . . . . ?
O1C C2C C3C F5C -172.0(3) . . . . ?
C1C C2C C3C F5C -51.5(4) . . . . ?
F3D C1D C2D O1D 56.4(3) . . . . ?
F2D C1D C2D O1D 178.6(2) . . . . ?
F1D C1D C2D O1D -63.3(3) . . . . ?
F3D C1D C2D C3D -63.9(3) . . . . ?
F2D C1D C2D C3D 58.3(3) . . . . ?
F1D C1D C2D C3D 176.5(2) . . . . ?
O1D C2D C3D F4D -56.6(3) . . . . ?
C1D C2D C3D F4D 62.0(3) . . . . ?
O1D C2D C3D F6D 63.8(3) . . . . ?
C1D C2D C3D F6D -177.6(3) . . . . ?
O1D C2D C3D F5D -178.5(2) . . . . ?
C1D C2D C3D F5D -60.0(3) . . . . ?
F3E C1E C2E O1E 52.7(3) . . . . ?
F1E C1E C2E O1E -66.5(3) . . . . ?
F2E C1E C2E O1E 174.2(2) . . . . ?
F3E C1E C2E C3E -67.3(4) . . . . ?
F1E C1E C2E C3E 173.5(3) . . . . ?
F2E C1E C2E C3E 54.2(4) . . . . ?
O1E C2E C3E F4E -61.3(3) . . . . ?
C1E C2E C3E F4E 58.9(4) . . . . ?
O1E C2E C3E F5E 177.4(2) . . . . ?
C1E C2E C3E F5E -62.4(4) . . . . ?
O1E C2E C3E F6E 58.2(3) . . . . ?
C1E C2E C3E F6E 178.4(3) . . . . ?
F2F C1F C2F O1F 178.3(2) . . . . ?
F3F C1F C2F O1F 56.6(3) . . . . ?
F1F C1F C2F O1F -61.2(3) . . . . ?
F2F C1F C2F C3F 56.9(4) . . . . ?
F3F C1F C2F C3F -64.7(4) . . . . ?
F1F C1F C2F C3F 177.5(3) . . . . ?
O1F C2F C3F F5F 180.0(3) . . . . ?
C1F C2F C3F F5F -61.2(4) . . . . ?
O1F C2F C3F F6F 59.3(3) . . . . ?
C1F C2F C3F F6F 178.1(3) . . . . ?
O1F C2F C3F F4F -58.0(4) . . . . ?
C1F C2F C3F F4F 60.9(4) . . . . ?

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
N10A H10A N1B 0.88 2.06 2.937(3) 176.4 .
N10A H11A O1D 0.88 2.22 3.066(3) 160.3 .
N10A H11A F1D 0.88 2.52 3.119(3) 125.9 .
N10B H10B N1A 0.88 2.10 2.957(3) 166.0 .
N10B H11B O1F 0.88 2.39 3.180(3) 150.1 .
N10B H11B F1F 0.88 2.52 3.213(3) 136.4 .
O1C H1C N3A 0.87(4) 1.84(4) 2.708(3) 172(3) .
O1D H1D N7A 0.79(3) 1.91(3) 2.675(3) 162(3) .
O1E H1E N3B 0.82(3) 1.88(3) 2.682(3) 169(3) .
O1F H1F N7B 0.77(3) 1.94(3) 2.674(3) 158(4) .

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-2

