# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_bo669

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H16 N22'
_chemical_formula_weight         396.41

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'

_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                   5.4170(12)
_cell_length_b                   11.956(3)
_cell_length_c                   24.503(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.202(3)
_cell_angle_gamma                90.00
_cell_volume                     1585.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4033
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12353
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3550
_reflns_number_gt                2664
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0495P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_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
N1 N 0.1435(3) 0.47782(12) 0.79339(6) 0.0155(3) Uani 1 1 d . . .
N2 N 0.2103(3) 0.56435(12) 0.76141(6) 0.0157(3) Uani 1 1 d . . .
N3 N 0.4088(3) 0.53916(12) 0.73519(6) 0.0158(3) Uani 1 1 d . . .
N4 N 0.4799(3) 0.43365(12) 0.74850(6) 0.0148(3) Uani 1 1 d . . .
N5 N 0.3098(3) 0.29353(12) 0.80682(6) 0.0142(3) Uani 1 1 d . . .
N6 N 0.5470(3) 0.25472(14) 0.82357(7) 0.0195(4) Uani 1 1 d . . .
N7 N 0.8841(3) 0.27064(12) 0.88914(6) 0.0156(3) Uani 1 1 d . . .
N8 N 0.9339(3) 0.34519(13) 0.93004(6) 0.0164(3) Uani 1 1 d . . .
N9 N 0.7539(3) 0.41765(13) 0.93206(6) 0.0159(3) Uani 1 1 d . . .
N10 N 0.5772(3) 0.39402(12) 0.89322(6) 0.0156(3) Uani 1 1 d . . .
N11 N 0.9539(3) 0.92108(12) 0.84908(6) 0.0124(3) Uani 1 1 d . . .
N12 N 0.7541(3) 0.91755(13) 0.88143(6) 0.0162(3) Uani 1 1 d . . .
N13 N 0.6580(3) 0.82094(13) 0.87725(6) 0.0154(3) Uani 1 1 d . . .
N14 N 0.7926(3) 0.76023(12) 0.84204(6) 0.0129(3) Uani 1 1 d . . .
N15 N 0.7334(3) 0.64909(13) 0.83186(7) 0.0175(3) Uani 1 1 d . . .
N16 N 1.1516(3) 0.79194(13) 0.79093(6) 0.0134(3) Uani 1 1 d . . .
N17 N 0.5350(3) 0.29459(12) 0.50076(6) 0.0138(3) Uani 1 1 d . . .
N18 N 0.7473(3) 0.34164(13) 0.52240(6) 0.0169(3) Uani 1 1 d . . .
N19 N 0.8415(3) 0.27390(12) 0.55751(6) 0.0153(3) Uani 1 1 d . . .
N20 N 0.6929(3) 0.18206(12) 0.55893(6) 0.0130(3) Uani 1 1 d . . .
N21 N 0.7431(3) 0.10165(14) 0.59865(7) 0.0166(3) Uani 1 1 d . . .
N22 N 0.3087(3) 0.12720(13) 0.51545(6) 0.0145(3) Uani 1 1 d . . .
C1 C 0.3136(3) 0.40064(14) 0.78406(7) 0.0123(4) Uani 1 1 d . . .
C2 C 0.6654(3) 0.30446(14) 0.86821(7) 0.0128(4) Uani 1 1 d . . .
C3 C 0.9818(3) 0.82220(14) 0.82427(7) 0.0114(4) Uani 1 1 d . . .
C4 C 1.1176(3) 1.01744(15) 0.84804(7) 0.0168(4) Uani 1 1 d . . .
H4A H 1.2770 0.9982 0.8658 0.020 Uiso 1 1 calc R . .
H4B H 1.0435 1.0799 0.8675 0.020 Uiso 1 1 calc R . .
H4C H 1.1425 1.0392 0.8101 0.020 Uiso 1 1 calc R . .
C5 C 0.4953(3) 0.19499(14) 0.52412(7) 0.0123(4) Uani 1 1 d . . .
C6 C 0.3780(3) 0.35626(16) 0.46173(7) 0.0189(4) Uani 1 1 d . . .
H6A H 0.2956 0.3037 0.4363 0.023 Uiso 1 1 calc R . .
H6B H 0.4793 0.4084 0.4413 0.023 Uiso 1 1 calc R . .
H6C H 0.2535 0.3982 0.4813 0.023 Uiso 1 1 calc R . .
H5N H 0.205(4) 0.2901(17) 0.8334(8) 0.020(6) Uiso 1 1 d . . .
H6N H 0.575(4) 0.1811(19) 0.8147(8) 0.025(6) Uiso 1 1 d . . .
H15A H 0.860(4) 0.6042(19) 0.8411(9) 0.028(6) Uiso 1 1 d . . .
H15B H 0.694(5) 0.642(2) 0.7956(10) 0.041(7) Uiso 1 1 d . . .
H16A H 1.147(4) 0.720(2) 0.7780(8) 0.025(6) Uiso 1 1 d . . .
H16B H 1.263(4) 0.844(2) 0.7780(9) 0.039(7) Uiso 1 1 d . . .
H21A H 0.615(4) 0.1007(18) 0.6196(9) 0.027(6) Uiso 1 1 d . . .
H21B H 0.749(4) 0.037(2) 0.5830(9) 0.035(7) Uiso 1 1 d . . .
H22A H 0.299(4) 0.060(2) 0.5348(10) 0.044(7) Uiso 1 1 d . . .
H22B H 0.200(4) 0.147(2) 0.4884(10) 0.040(7) Uiso 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 C1 1.330(2) . ?
N1 N2 1.356(2) . ?
N2 N3 1.309(2) . ?
N3 N4 1.355(2) . ?
N4 C1 1.337(2) . ?
N5 C1 1.397(2) . ?
N5 N6 1.412(2) . ?
N5 H5N 0.88(2) . ?
N6 C2 1.381(2) . ?
N6 H6N 0.92(2) . ?
N7 C2 1.335(2) . ?
N7 N8 1.360(2) . ?
N8 N9 1.307(2) . ?
N9 N10 1.353(2) . ?
N10 C2 1.332(2) . ?
N11 C3 1.341(2) . ?
N11 N12 1.366(2) . ?
N11 C4 1.455(2) . ?
N12 N13 1.270(2) . ?
N13 N14 1.361(2) . ?
N14 C3 1.350(2) . ?
N14 N15 1.387(2) . ?
N15 H15A 0.89(2) . ?
N15 H15B 0.91(3) . ?
N16 C3 1.305(2) . ?
N16 H16A 0.91(2) . ?
N16 H16B 0.93(3) . ?
N17 C5 1.342(2) . ?
N17 N18 1.369(2) . ?
N17 C6 1.456(2) . ?
N18 N19 1.274(2) . ?
N19 N20 1.363(2) . ?
N20 C5 1.352(2) . ?
N20 N21 1.387(2) . ?
N21 H21A 0.88(2) . ?
N21 H21B 0.87(3) . ?
N22 C5 1.306(2) . ?
N22 H22A 0.94(3) . ?
N22 H22B 0.90(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 N2 103.17(13) . . ?
N3 N2 N1 110.55(14) . . ?
N2 N3 N4 109.10(14) . . ?
C1 N4 N3 103.85(14) . . ?
C1 N5 N6 112.97(14) . . ?
C1 N5 H5N 110.9(13) . . ?
N6 N5 H5N 112.0(13) . . ?
C2 N6 N5 118.58(15) . . ?
C2 N6 H6N 121.5(13) . . ?
N5 N6 H6N 113.7(13) . . ?
C2 N7 N8 103.44(14) . . ?
N9 N8 N7 109.58(14) . . ?
N8 N9 N10 110.10(14) . . ?
C2 N10 N9 103.59(14) . . ?
C3 N11 N12 109.96(14) . . ?
C3 N11 C4 127.67(14) . . ?
N12 N11 C4 122.11(14) . . ?
N13 N12 N11 108.24(14) . . ?
N12 N13 N14 107.95(14) . . ?
C3 N14 N13 110.10(14) . . ?
C3 N14 N15 129.86(15) . . ?
N13 N14 N15 119.93(14) . . ?
N14 N15 H15A 111.1(15) . . ?
N14 N15 H15B 107.8(16) . . ?
H15A N15 H15B 110(2) . . ?
C3 N16 H16A 117.9(13) . . ?
C3 N16 H16B 120.6(14) . . ?
H16A N16 H16B 121.2(19) . . ?
C5 N17 N18 110.22(14) . . ?
C5 N17 C6 129.08(15) . . ?
N18 N17 C6 120.48(15) . . ?
N19 N18 N17 108.01(14) . . ?
N18 N19 N20 107.93(14) . . ?
C5 N20 N19 110.25(14) . . ?
C5 N20 N21 130.61(15) . . ?
N19 N20 N21 118.44(14) . . ?
N20 N21 H21A 106.3(14) . . ?
N20 N21 H21B 108.7(15) . . ?
H21A N21 H21B 107(2) . . ?
C5 N22 H22A 120.7(15) . . ?
C5 N22 H22B 116.2(15) . . ?
H22A N22 H22B 123(2) . . ?
N1 C1 N4 113.32(16) . . ?
N1 C1 N5 123.13(16) . . ?
N4 C1 N5 123.45(16) . . ?
N10 C2 N7 113.29(15) . . ?
N10 C2 N6 123.15(16) . . ?
N7 C2 N6 123.50(16) . . ?
N16 C3 N11 128.53(16) . . ?
N16 C3 N14 127.72(16) . . ?
N11 C3 N14 103.74(14) . . ?
N11 C4 H4A 109.5 . . ?
N11 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N11 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N22 C5 N17 128.08(17) . . ?
N22 C5 N20 128.36(16) . . ?
N17 C5 N20 103.55(15) . . ?
N17 C6 H6A 109.5 . . ?
N17 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N17 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C1 N1 N2 N3 -0.33(18) . . . . ?
N1 N2 N3 N4 0.65(19) . . . . ?
N2 N3 N4 C1 -0.68(18) . . . . ?
C1 N5 N6 C2 69.8(2) . . . . ?
C2 N7 N8 N9 -0.27(18) . . . . ?
N7 N8 N9 N10 0.51(19) . . . . ?
N8 N9 N10 C2 -0.52(18) . . . . ?
C3 N11 N12 N13 -0.31(19) . . . . ?
C4 N11 N12 N13 -174.88(16) . . . . ?
N11 N12 N13 N14 -0.24(18) . . . . ?
N12 N13 N14 C3 0.71(19) . . . . ?
N12 N13 N14 N15 177.22(15) . . . . ?
C5 N17 N18 N19 1.05(19) . . . . ?
C6 N17 N18 N19 176.10(15) . . . . ?
N17 N18 N19 N20 0.32(18) . . . . ?
N18 N19 N20 C5 -1.57(19) . . . . ?
N18 N19 N20 N21 -172.93(15) . . . . ?
N2 N1 C1 N4 -0.12(19) . . . . ?
N2 N1 C1 N5 -176.65(16) . . . . ?
N3 N4 C1 N1 0.50(19) . . . . ?
N3 N4 C1 N5 177.01(15) . . . . ?
N6 N5 C1 N1 -140.30(17) . . . . ?
N6 N5 C1 N4 43.5(2) . . . . ?
N9 N10 C2 N7 0.36(19) . . . . ?
N9 N10 C2 N6 -176.98(16) . . . . ?
N8 N7 C2 N10 -0.07(19) . . . . ?
N8 N7 C2 N6 177.26(16) . . . . ?
N5 N6 C2 N10 -6.4(3) . . . . ?
N5 N6 C2 N7 176.52(15) . . . . ?
N12 N11 C3 N16 -179.02(16) . . . . ?
C4 N11 C3 N16 -4.8(3) . . . . ?
N12 N11 C3 N14 0.71(18) . . . . ?
C4 N11 C3 N14 174.90(16) . . . . ?
N13 N14 C3 N16 178.87(16) . . . . ?
N15 N14 C3 N16 2.8(3) . . . . ?
N13 N14 C3 N11 -0.85(18) . . . . ?
N15 N14 C3 N11 -176.91(17) . . . . ?
N18 N17 C5 N22 177.68(17) . . . . ?
C6 N17 C5 N22 3.2(3) . . . . ?
N18 N17 C5 N20 -1.91(18) . . . . ?
C6 N17 C5 N20 -176.43(16) . . . . ?
N19 N20 C5 N22 -177.48(16) . . . . ?
N21 N20 C5 N22 -7.5(3) . . . . ?
N19 N20 C5 N17 2.11(18) . . . . ?
N21 N20 C5 N17 172.10(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053

_database_code_depnum_ccdc_archive 'CCDC 779222'
