# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_juh017
_database_code_depnum_ccdc_archive 'CCDC 1454697'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-04-12 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            'C20 H34 F12 N8 P2'
_chemical_formula_weight         676.49

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'
P P 0.1023 0.0942 '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                   9.0000(18)
_cell_length_b                   14.045(3)
_cell_length_c                   11.779(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.38(3)
_cell_angle_gamma                90
_cell_volume                     1487.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    7879
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.16

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_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 KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7879
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         29.156
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3998
_reflns_number_gt                2828
_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       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0819P)²+0.7221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3998
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
P1 P 0.68327(6) 0.86962(4) 0.19348(5) 0.03539(17) Uani 1 1 d . . . . .
F1 F 0.77189(17) 0.79092(11) 0.26498(12) 0.0539(4) Uani 1 1 d . . . . .
F2 F 0.78275(19) 0.95210(12) 0.24935(14) 0.0649(5) Uani 1 1 d . . . . .
F3 F 0.5917(3) 0.94603(13) 0.1221(2) 0.1029(9) Uani 1 1 d . . . . .
F4 F 0.5805(2) 0.78721(10) 0.13936(14) 0.0633(5) Uani 1 1 d . . . . .
F5 F 0.57483(18) 0.87953(12) 0.29609(17) 0.0692(5) Uani 1 1 d . . . . .
F6 F 0.7931(3) 0.85904(16) 0.09353(16) 0.0920(7) Uani 1 1 d . . . . .
N1 N 0.78886(17) 1.02613(12) 0.56667(13) 0.0271(3) Uani 1 1 d . . . . .
N2 N 0.86186(18) 0.99833(12) 0.75471(14) 0.0290(4) Uani 1 1 d . . . . .
N3 N 0.92778(17) 0.88956(12) 0.61306(14) 0.0286(4) Uani 1 1 d . . . . .
C1 C 0.6506(2) 1.01184(13) 0.53777(15) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.5796(2) 1.07831(13) 0.45709(15) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.6339 1.1294 0.4305 0.031 Uiso 1 1 calc R U . . .
C4 C 0.86003(19) 0.96704(14) 0.64842(16) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.8861(2) 0.93766(16) 0.85544(17) 0.0372(5) Uani 1 1 d . . . . .
H5A H 0.8702 0.8722 0.8346 0.056 Uiso 1 1 calc R U . . .
H5B H 0.8177 0.9554 0.9122 0.056 Uiso 1 1 calc R U . . .
H5C H 0.9862 0.9457 0.8853 0.056 Uiso 1 1 calc R U . . .
C6 C 0.8217(3) 1.09715(16) 0.78023(19) 0.0382(5) Uani 1 1 d . . . . .
H6A H 0.8349 1.1361 0.7144 0.057 Uiso 1 1 calc R U . . .
H6B H 0.8844 1.1202 0.8422 0.057 Uiso 1 1 calc R U . . .
H6C H 0.7197 1.0997 0.8007 0.057 Uiso 1 1 calc R U . . .
C7 C 1.0512(2) 0.84358(15) 0.67762(19) 0.0331(4) Uani 1 1 d . . . . .
H7A H 1.0995 0.8894 0.7271 0.050 Uiso 1 1 calc R U . . .
H7B H 1.1214 0.8190 0.6259 0.050 Uiso 1 1 calc R U . . .
H7C H 1.0133 0.7924 0.7220 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8923(2) 0.84996(16) 0.49957(18) 0.0341(4) Uani 1 1 d . . . . .
H8A H 0.7934 0.8243 0.4973 0.051 Uiso 1 1 calc R U . . .
H8B H 0.9618 0.8003 0.4837 0.051 Uiso 1 1 calc R U . . .
H8C H 0.8987 0.8994 0.4437 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4383(2) 1.06702(13) 0.42087(15) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.3958 1.1098 0.3687 0.030 Uiso 1 1 calc R U . . .
N11 N 1.2144(2) 0.79501(16) 0.95222(18) 0.0472(5) Uani 1 1 d . . . . .
C11 C 1.3277(3) 0.81410(15) 0.91935(18) 0.0357(5) Uani 1 1 d . . . . .
C12 C 1.4727(3) 0.8378(2) 0.8772(2) 0.0490(6) Uani 1 1 d . . . . .
H12A H 1.4954 0.7952 0.8165 0.073 Uiso 1 1 calc R U . . .
H12B H 1.5470 0.8318 0.9376 0.073 Uiso 1 1 calc R U . . .
H12C H 1.4714 0.9021 0.8494 0.073 Uiso 1 1 calc R U . . .


_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
P1 F3 1.5749(17) . ?
P1 F6 1.5754(19) . ?
P1 F1 1.5847(15) . ?
P1 F2 1.5898(16) . ?
P1 F5 1.5908(17) . ?
P1 F4 1.5977(16) . ?
N1 C1 1.292(2) . ?
N1 C4 1.405(2) . ?
N2 C4 1.326(2) . ?
N2 C6 1.468(3) . ?
N2 C5 1.470(3) . ?
N3 C4 1.323(2) . ?
N3 C7 1.469(2) . ?
N3 C8 1.471(3) . ?
C1 C2 1.460(2) . ?
C1 C3 1.461(2) 3_676 ?
C2 C3 1.334(3) . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C3 C1 1.461(2) 3_676 ?
C3 H3 0.9300 . ?
N11 C11 1.138(3) . ?
C11 C12 1.455(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
F3 P1 F6 89.75(14) . . ?
F3 P1 F1 178.53(11) . . ?
F6 P1 F1 90.79(11) . . ?
F3 P1 F2 89.87(10) . . ?
F6 P1 F2 91.03(11) . . ?
F1 P1 F2 91.49(10) . . ?
F3 P1 F5 91.28(13) . . ?
F6 P1 F5 178.88(12) . . ?
F1 P1 F5 88.19(10) . . ?
F2 P1 F5 88.54(9) . . ?
F3 P1 F4 89.95(10) . . ?
F6 P1 F4 90.24(12) . . ?
F1 P1 F4 88.68(9) . . ?
F2 P1 F4 178.71(10) . . ?
F5 P1 F4 90.19(10) . . ?
C1 N1 C4 119.69(16) . . ?
C4 N2 C6 120.86(16) . . ?
C4 N2 C5 124.45(17) . . ?
C6 N2 C5 114.34(16) . . ?
C4 N3 C7 123.16(16) . . ?
C4 N3 C8 120.78(16) . . ?
C7 N3 C8 115.79(16) . . ?
N1 C1 C2 117.55(16) . . ?
N1 C1 C3 124.35(17) . 3_676 ?
C2 C1 C3 118.10(16) . 3_676 ?
C3 C2 C1 121.16(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N3 C4 N2 125.58(17) . . ?
N3 C4 N1 118.22(17) . . ?
N2 C4 N1 116.01(17) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 C1 120.74(17) . 3_676 ?
C2 C3 H3 119.6 . . ?
C1 C3 H3 119.6 3_676 . ?
N11 C11 C12 179.6(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 N1 C1 C2 176.77(16) . . . . ?
C4 N1 C1 C3 -4.2(3) . . . 3_676 ?
N1 C1 C2 C3 178.30(18) . . . . ?
C3 C1 C2 C3 -0.8(3) 3_676 . . . ?
C7 N3 C4 N2 -19.8(3) . . . . ?
C8 N3 C4 N2 166.46(18) . . . . ?
C7 N3 C4 N1 155.04(17) . . . . ?
C8 N3 C4 N1 -18.7(3) . . . . ?
C6 N2 C4 N3 161.97(18) . . . . ?
C5 N2 C4 N3 -25.2(3) . . . . ?
C6 N2 C4 N1 -13.0(3) . . . . ?
C5 N2 C4 N1 159.82(17) . . . . ?
C1 N1 C4 N3 90.5(2) . . . . ?
C1 N1 C4 N2 -94.2(2) . . . . ?
C1 C2 C3 C1 0.8(3) . . . 3_676 ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_juh004
_database_code_depnum_ccdc_archive 'CCDC 1454698'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-04-12 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            'C16 H28 N6'
_chemical_formula_weight         304.44

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'

_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                   6.9120(14)
_cell_length_b                   8.3560(17)
_cell_length_c                   8.8440(18)
_cell_angle_alpha                110.90(3)
_cell_angle_beta                 97.94(3)
_cell_angle_gamma                111.50(3)
_cell_volume                     422.20(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4364
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.05

_exptl_crystal_description       'box shaped'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             166
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_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 KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4364
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         30.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2451
_reflns_number_gt                1800
_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       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0586P)²+0.1176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.03046(16) 0.73351(15) 0.82948(13) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.30490(17) 0.69239(15) 0.70448(14) 0.0182(2) Uani 1 1 d . . . . .
N3 N 0.23876(17) 0.95681(15) 0.74915(13) 0.0166(2) Uani 1 1 d . . . . .
C1 C 0.02129(19) 0.61423(17) 0.91039(15) 0.0150(3) Uani 1 1 d . . . . .
C2 C -0.18281(19) 0.47351(17) 0.88918(16) 0.0166(3) Uani 1 1 d . . . . .
H2 H -0.3072 0.4547 0.8151 0.020 Uiso 1 1 calc R U . . .
C3 C -0.20455(19) 0.36123(17) 0.97567(15) 0.0167(3) Uani 1 1 d . . . . .
H3 H -0.3425 0.2684 0.9579 0.020 Uiso 1 1 calc R U . . .
C4 C 0.18599(19) 0.78825(17) 0.76511(15) 0.0153(2) Uani 1 1 d . . . . .
C5 C 0.5354(2) 0.7895(2) 0.72245(19) 0.0243(3) Uani 1 1 d . . . . .
H5A H 0.5528 0.7688 0.6122 0.036 Uiso 1 1 calc R U . . .
H5B H 0.6146 0.7394 0.7743 0.036 Uiso 1 1 calc R U . . .
H5C H 0.5911 0.9245 0.7926 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2136(2) 0.48607(18) 0.63928(17) 0.0224(3) Uani 1 1 d . . . . .
H6A H 0.2779 0.4548 0.7211 0.034 Uiso 1 1 calc R U . . .
H6B H 0.2440 0.4338 0.5348 0.034 Uiso 1 1 calc R U . . .
H6C H 0.0583 0.4328 0.6186 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2839(2) 0.97043(19) 0.59715(17) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.3027 0.8612 0.5304 0.032 Uiso 1 1 calc R U . . .
H7B H 0.4150 1.0856 0.6295 0.032 Uiso 1 1 calc R U . . .
H7C H 0.1638 0.9735 0.5313 0.032 Uiso 1 1 calc R U . . .
C8 C 0.1478(2) 1.08303(19) 0.83326(17) 0.0206(3) Uani 1 1 d . . . . .
H8A H 0.0044 1.0415 0.7615 0.031 Uiso 1 1 calc R U . . .
H8B H 0.2406 1.2118 0.8545 0.031 Uiso 1 1 calc R U . . .
H8C H 0.1383 1.0790 0.9392 0.031 Uiso 1 1 calc R U . . .


_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 C4 1.2975(16) . ?
N1 C1 1.4087(15) . ?
N2 C4 1.3794(16) . ?
N2 C6 1.4476(17) . ?
N2 C5 1.4535(17) . ?
N3 C4 1.3843(16) . ?
N3 C7 1.4549(16) . ?
N3 C8 1.4550(16) . ?
C1 C2 1.4006(17) . ?
C1 C3 1.4040(18) 2_567 ?
C2 C3 1.3886(17) . ?
C2 H2 0.9300 . ?
C3 C1 1.4040(18) 2_567 ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C4 N1 C1 121.63(11) . . ?
C4 N2 C6 121.04(11) . . ?
C4 N2 C5 123.22(11) . . ?
C6 N2 C5 115.21(11) . . ?
C4 N3 C7 121.18(11) . . ?
C4 N3 C8 118.60(10) . . ?
C7 N3 C8 113.50(10) . . ?
C2 C1 C3 117.22(11) . 2_567 ?
C2 C1 N1 118.98(11) . . ?
C3 C1 N1 123.56(11) 2_567 . ?
C3 C2 C1 121.81(11) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C1 120.97(11) . 2_567 ?
C2 C3 H3 119.5 . . ?
C1 C3 H3 119.5 2_567 . ?
N1 C4 N2 126.69(11) . . ?
N1 C4 N3 118.59(11) . . ?
N2 C4 N3 114.69(11) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C4 N1 C1 C2 -142.75(12) . . . . ?
C4 N1 C1 C3 43.10(18) . . . 2_567 ?
C3 C1 C2 C3 -0.5(2) 2_567 . . . ?
N1 C1 C2 C3 -175.00(11) . . . . ?
C1 C2 C3 C1 0.5(2) . . . 2_567 ?
C1 N1 C4 N2 27.10(19) . . . . ?
C1 N1 C4 N3 -154.84(11) . . . . ?
C6 N2 C4 N1 26.74(19) . . . . ?
C5 N2 C4 N1 -144.50(13) . . . . ?
C6 N2 C4 N3 -151.38(11) . . . . ?
C5 N2 C4 N3 37.38(16) . . . . ?
C7 N3 C4 N1 -138.06(13) . . . . ?
C8 N3 C4 N1 11.35(17) . . . . ?
C7 N3 C4 N2 40.22(16) . . . . ?
C8 N3 C4 N2 -170.37(10) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053

