# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_auto
_database_code_depnum_ccdc_archive 'CCDC 1027851'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-07T14:27:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C12 H18 N4'
_chemical_formula_moiety         'C12 H18 N4'
_chemical_formula_weight         218.3

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.770(3)
_cell_length_b                   7.311(2)
_cell_length_c                   11.141(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.425(4)
_cell_angle_gamma                90
_cell_volume                     596.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.57
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_number            4382
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_reflns_number_total             1344
_reflns_number_gt                1183
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0525P)²+0.0926P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1344
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.19
_refine_ls_restrained_S_all      1.19
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.27007(11) 0.22721(12) 0.51765(8) 0.0169(2) Uani 1 1 d . . .
N2 N 0.15660(11) 0.18684(11) 0.59006(7) 0.0160(2) Uani 1 1 d . . .
C6 C 0.01582(12) 0.05980(12) 0.55497(9) 0.0139(2) Uani 1 1 d . . .
C3 C 0.15692(13) 0.27998(14) 0.69712(9) 0.0187(3) Uani 1 1 d . . .
H3 H 0.2378 0.3719 0.7382 0.022 Uiso 1 1 calc R . .
C5 C -0.07236(12) 0.07562(13) 0.64404(9) 0.0163(2) Uani 1 1 d . . .
H5 H -0.1728 0.0076 0.6455 0.02 Uiso 1 1 calc R . .
C4 C 0.01654(14) 0.21278(14) 0.73234(9) 0.0188(2) Uani 1 1 d . . .
H4 H -0.0149 0.2506 0.802 0.023 Uiso 1 1 calc R . .
C1 C 0.46207(13) 0.20890(15) 0.59565(10) 0.0223(3) Uani 1 1 d . . .
H1A H 0.4838 0.0878 0.6308 0.033 Uiso 1 1 calc R . .
H1B H 0.4912 0.2969 0.6634 0.033 Uiso 1 1 calc R . .
H1C H 0.5373 0.2299 0.5439 0.033 Uiso 1 1 calc R . .
C2 C 0.22518(15) 0.40852(15) 0.46011(10) 0.0241(3) Uani 1 1 d . . .
H2A H 0.098 0.4129 0.4102 0.036 Uiso 1 1 calc R . .
H2B H 0.2971 0.4323 0.4065 0.036 Uiso 1 1 calc R . .
H2C H 0.251 0.4994 0.5259 0.036 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 1.4101(11) . ?
N1 C1 1.4617(13) . ?
N1 C2 1.4631(14) . ?
N2 C3 1.3728(13) . ?
N2 C6 1.3884(12) . ?
C6 C5 1.3856(14) . ?
C6 C6 1.4576(18) 3_556 ?
C3 H3 0.930 . ?
C3 C4 1.3675(14) . ?
C5 H5 0.930 . ?
C5 C4 1.4137(14) . ?
C4 H4 0.930 . ?
C1 H1A 0.960 . ?
C1 H1B 0.960 . ?
C1 H1C 0.960 . ?
C2 H2A 0.960 . ?
C2 H2B 0.960 . ?
C2 H2C 0.960 . ?

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
N2 N1 C1 110.45(8) . . ?
N2 N1 C2 109.69(8) . . ?
C1 N1 C2 113.01(8) . . ?
C3 N2 C6 110.49(8) . . ?
C3 N2 N1 124.92(8) . . ?
C6 N2 N1 124.26(8) . . ?
C5 C6 N2 105.87(8) . . ?
C5 C6 C6 131.79(11) . 3_556 ?
N2 C6 C6 122.33(10) . 3_556 ?
C4 C3 N2 107.46(9) . . ?
C6 C5 C4 108.30(8) . . ?
C3 C4 C5 107.88(9) . . ?
N2 C3 H3 126.3 . . ?
H3 C3 C4 126.3 . . ?
C6 C5 H5 125.8 . . ?
H5 C5 C4 125.9 . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
N1 C1 H1A 109.47 . . ?
N1 C1 H1B 109.47 . . ?
N1 C1 H1C 109.46 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.4 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.4 . . ?
H2B C2 H2C 109.4 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_auto
_database_code_depnum_ccdc_archive 'CCDC 1027852'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-07T14:15:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C18 H26 N6'
_chemical_formula_moiety         'C18 H26 N6'
_chemical_formula_weight         326.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   14.8107(13)
_cell_length_b                   7.9825(5)
_cell_length_c                   15.3064(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.4630(10)
_cell_angle_gamma                90
_cell_volume                     1809.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.57
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_number            13892
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             4139
_reflns_number_gt                3410
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0566P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.12
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.53795(7) -0.12509(13) -0.09589(7) 0.0182(2) Uani 1 1 d . . .
N5 N 0.80696(7) 0.01402(13) 0.15330(7) 0.0203(2) Uani 1 1 d . . .
N2 N 0.58339(7) -0.10141(13) -0.17527(7) 0.0179(2) Uani 1 1 d . . .
N6 N 0.85437(7) 0.16266(13) 0.13365(7) 0.0184(2) Uani 1 1 d . . .
N3 N 0.81666(7) -0.02244(13) -0.05553(7) 0.0209(3) Uani 1 1 d . . .
N4 N 0.75006(7) 0.10359(12) -0.05566(7) 0.0168(2) Uani 1 1 d . . .
C1 C 0.44669(9) -0.05632(18) -0.10295(9) 0.0251(3) Uani 1 1 d . . .
H1A H 0.4497 0.0603 -0.1179 0.038 Uiso 1 1 calc R . .
H1B H 0.4175 -0.0686 -0.048 0.038 Uiso 1 1 calc R . .
H1C H 0.4129 -0.1154 -0.1475 0.038 Uiso 1 1 calc R . .
C12 C 0.75933(8) 0.23868(15) -0.00020(8) 0.0173(3) Uani 1 1 d . . .
C6 C 0.65105(9) 0.01528(15) -0.18501(8) 0.0180(3) Uani 1 1 d . . .
C5 C 0.67903(9) 0.00184(16) -0.27004(8) 0.0220(3) Uani 1 1 d . . .
H5 H 0.7238 0.0655 -0.2956 0.026 Uiso 1 1 calc R . .
C2 C 0.53626(9) -0.30289(17) -0.07299(9) 0.0253(3) Uani 1 1 d . . .
H2A H 0.597 -0.3449 -0.0688 0.038 Uiso 1 1 calc R . .
H2B H 0.503 -0.3637 -0.1173 0.038 Uiso 1 1 calc R . .
H2C H 0.5077 -0.3168 -0.0179 0.038 Uiso 1 1 calc R . .
C10 C 0.64238(9) 0.28363(16) -0.09411(8) 0.0191(3) Uani 1 1 d . . .
H10 H 0.5929 0.3337 -0.1222 0.023 Uiso 1 1 calc R . .
C16 C 0.89380(9) 0.39451(16) 0.06582(9) 0.0242(3) Uani 1 1 d . . .
H16 H 0.8964 0.4821 0.0259 0.029 Uiso 1 1 calc R . .
C15 C 0.83413(8) 0.26313(15) 0.06222(8) 0.0180(3) Uani 1 1 d . . .
C9 C 0.67882(8) 0.13114(15) -0.11465(8) 0.0167(3) Uani 1 1 d . . .
C4 C 0.62748(9) -0.12579(17) -0.31137(8) 0.0239(3) Uani 1 1 d . . .
H4 H 0.6325 -0.1617 -0.3688 0.029 Uiso 1 1 calc R . .
C7 C 0.88054(10) 0.0055(2) -0.12522(10) 0.0350(4) Uani 1 1 d . . .
H7A H 0.9033 0.118 -0.1215 0.052 Uiso 1 1 calc R . .
H7B H 0.8505 -0.0108 -0.1809 0.052 Uiso 1 1 calc R . .
H7C H 0.9298 -0.0722 -0.119 0.052 Uiso 1 1 calc R . .
C14 C 0.86746(10) -0.13036(17) 0.14960(9) 0.0260(3) Uani 1 1 d . . .
H14A H 0.8932 -0.1365 0.0928 0.039 Uiso 1 1 calc R . .
H14B H 0.834 -0.2309 0.1605 0.039 Uiso 1 1 calc R . .
H14C H 0.9149 -0.1184 0.1931 0.039 Uiso 1 1 calc R . .
C17 C 0.95069(9) 0.37418(17) 0.14059(9) 0.0264(3) Uani 1 1 d . . .
H17 H 0.9971 0.4456 0.1588 0.032 Uiso 1 1 calc R . .
C11 C 0.69276(9) 0.35153(16) -0.02306(8) 0.0192(3) Uani 1 1 d . . .
H11 H 0.6827 0.4544 0.0036 0.023 Uiso 1 1 calc R . .
C8 C 0.77815(10) -0.19001(16) -0.05537(10) 0.0292(3) Uani 1 1 d . . .
H8A H 0.737 -0.1999 -0.0082 0.044 Uiso 1 1 calc R . .
H8B H 0.8257 -0.271 -0.048 0.044 Uiso 1 1 calc R . .
H8C H 0.7464 -0.2098 -0.1099 0.044 Uiso 1 1 calc R . .
C3 C 0.56873(9) -0.18707(16) -0.25161(8) 0.0219(3) Uani 1 1 d . . .
H3 H 0.5265 -0.2717 -0.2612 0.026 Uiso 1 1 calc R . .
C18 C 0.92505(9) 0.23052(17) 0.18115(9) 0.0228(3) Uani 1 1 d . . .
H18 H 0.9509 0.1863 0.2321 0.027 Uiso 1 1 calc R . .
C13 C 0.76623(10) 0.02800(18) 0.23915(9) 0.0267(3) Uani 1 1 d . . .
H13A H 0.7269 0.1236 0.2398 0.04 Uiso 1 1 calc R . .
H13B H 0.813 0.0411 0.2833 0.04 Uiso 1 1 calc R . .
H13C H 0.7321 -0.0715 0.2507 0.04 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 1.4166(14) . ?
N1 C1 1.4603(16) . ?
N1 C2 1.4623(16) . ?
N5 N6 1.4149(15) . ?
N5 C14 1.4619(17) . ?
N5 C13 1.4641(17) . ?
N2 C3 1.3663(16) . ?
N2 C6 1.3791(16) . ?
N6 C18 1.3707(16) . ?
N6 C15 1.3826(16) . ?
N3 N4 1.4088(14) . ?
N3 C8 1.4542(17) . ?
N3 C7 1.4609(18) . ?
N4 C12 1.3771(15) . ?
N4 C9 1.3886(15) . ?
C12 C11 1.3742(18) . ?
C12 C15 1.4575(17) . ?
C6 C5 1.3801(17) . ?
C6 C9 1.4703(17) . ?
C5 C4 1.4130(19) . ?
C2 H2A 0.961 . ?
C2 H2B 0.960 . ?
C2 H2C 0.959 . ?
C10 H10 0.930 . ?
C10 C9 1.3712(17) . ?
C10 C11 1.4114(18) . ?
C16 H16 0.930 . ?
C16 C15 1.3716(18) . ?
C16 C17 1.4130(19) . ?
C4 H4 0.929 . ?
C4 C3 1.3688(19) . ?
C7 H7A 0.960 . ?
C7 H7B 0.960 . ?
C7 H7C 0.960 . ?
C14 H14A 0.959 . ?
C14 H14B 0.960 . ?
C14 H14C 0.960 . ?
C17 H17 0.930 . ?
C17 C18 1.3627(19) . ?
C11 H11 0.931 . ?
C8 H8A 0.960 . ?
C8 H8B 0.961 . ?
C8 H8C 0.961 . ?
C3 H3 0.930 . ?
C18 H18 0.930 . ?
C13 H13A 0.960 . ?
C13 H13B 0.961 . ?
C13 H13C 0.960 . ?

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
N2 N1 C1 110.21(9) . . ?
N2 N1 C2 110.27(10) . . ?
C1 N1 C2 111.17(11) . . ?
N6 N5 C14 110.17(10) . . ?
N6 N5 C13 110.18(10) . . ?
C14 N5 C13 111.21(10) . . ?
C3 N2 C6 110.22(10) . . ?
C3 N2 N1 126.74(11) . . ?
C6 N2 N1 123.04(10) . . ?
C18 N6 C15 109.72(11) . . ?
C18 N6 N5 126.52(11) . . ?
C15 N6 N5 123.76(10) . . ?
N4 N3 C8 112.47(10) . . ?
N4 N3 C7 110.87(10) . . ?
C8 N3 C7 113.78(12) . . ?
C12 N4 C9 109.81(10) . . ?
C12 N4 N3 119.97(10) . . ?
C9 N4 N3 129.37(10) . . ?
C11 C12 N4 107.26(11) . . ?
C11 C12 C15 127.41(11) . . ?
N4 C12 C15 124.83(11) . . ?
N2 C6 C5 106.62(11) . . ?
N2 C6 C9 122.42(11) . . ?
C5 C6 C9 130.89(12) . . ?
C6 C5 C4 107.84(12) . . ?
C9 C10 C11 108.31(11) . . ?
C15 C16 C17 108.36(12) . . ?
C16 C15 N6 106.58(11) . . ?
C16 C15 C12 127.36(12) . . ?
N6 C15 C12 125.91(11) . . ?
C10 C9 N4 106.77(10) . . ?
C10 C9 C6 128.46(12) . . ?
N4 C9 C6 124.77(11) . . ?
C3 C4 C5 107.70(12) . . ?
C18 C17 C16 107.35(12) . . ?
C12 C11 C10 107.83(11) . . ?
N2 C3 C4 107.62(11) . . ?
C17 C18 N6 107.99(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.4 . . ?
H1A C1 H1B 109.4 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 H5 126.1 . . ?
H5 C5 C4 126.1 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.4 . . ?
H10 C10 C9 125.8 . . ?
H10 C10 C11 125.9 . . ?
H16 C16 C15 125.9 . . ?
H16 C16 C17 125.8 . . ?
C5 C4 H4 126.2 . . ?
H4 C4 C3 126.1 . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.4 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.4 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17 126.4 . . ?
H17 C17 C18 126.3 . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.4 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.4 . . ?
N2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N6 C18 H18 126.0 . . ?
C17 C18 H18 126.0 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_auto
_database_code_depnum_ccdc_archive 'CCDC 1027853'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-07T14:02:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C24 H34 N8'
_chemical_formula_moiety         'C24 H34 N8'
_chemical_formula_weight         434.59

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.414(12)
_cell_length_b                   7.947(3)
_cell_length_c                   15.216(8)
_cell_angle_alpha                90
_cell_angle_beta                 126.073(2)
_cell_angle_gamma                90
_cell_volume                     2288.3(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.57
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_number            8732
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             2609
_reflns_number_gt                2299
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0523P)²+1.4889P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2609
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
N4 N 0.95595(5) 0.16048(11) 0.11900(7) 0.0136(2) Uani 1 1 d . . .
N3 N 1.00444(5) 0.29338(11) 0.14895(8) 0.0163(2) Uani 1 1 d . . .
N2 N 0.81495(5) 0.33303(12) -0.11912(7) 0.0159(2) Uani 1 1 d . . .
N1 N 0.78049(5) 0.35818(12) -0.06857(8) 0.0180(2) Uani 1 1 d . . .
C12 C 0.97012(6) 0.03536(13) 0.19234(9) 0.0134(2) Uani 1 1 d . . .
C10 C 0.87643(6) -0.04071(14) 0.02460(9) 0.0160(2) Uani 1 1 d . . .
H10 H 0.8387 -0.1024 -0.0319 0.019 Uiso 1 1 calc R . .
C9 C 0.89830(6) 0.11418(13) 0.01514(9) 0.0139(2) Uani 1 1 d . . .
C6 C 0.86871(6) 0.21736(13) -0.08315(9) 0.0145(2) Uani 1 1 d . . .
C1 C 0.70712(6) 0.29925(16) -0.14097(10) 0.0229(3) Uani 1 1 d . . .
H1A H 0.7066 0.1824 -0.1575 0.034 Uiso 1 1 calc R . .
H1B H 0.6824 0.3635 -0.2071 0.034 Uiso 1 1 calc R . .
H1C H 0.6843 0.3133 -0.1057 0.034 Uiso 1 1 calc R . .
C5 C 0.88444(6) 0.22003(14) -0.15742(9) 0.0175(2) Uani 1 1 d . . .
H5 H 0.9184 0.1546 -0.1546 0.021 Uiso 1 1 calc R . .
C7 C 0.96980(6) 0.45746(14) 0.12068(10) 0.0205(3) Uani 1 1 d . . .
H7A H 0.9445 0.4685 0.1521 0.031 Uiso 1 1 calc R . .
H7B H 0.9374 0.4671 0.043 0.031 Uiso 1 1 calc R . .
H7C H 1.0048 0.5447 0.1483 0.031 Uiso 1 1 calc R . .
C2 C 0.78200(7) 0.53668(16) -0.04269(11) 0.0244(3) Uani 1 1 d . . .
H2A H 0.8301 0.5742 0.0046 0.037 Uiso 1 1 calc R . .
H2B H 0.7594 0.5512 -0.0072 0.037 Uiso 1 1 calc R . .
H2C H 0.7575 0.6015 -0.1086 0.037 Uiso 1 1 calc R . .
C11 C 0.92113(6) -0.09052(14) 0.13511(9) 0.0153(2) Uani 1 1 d . . .
H11 H 0.918 -0.1904 0.1639 0.018 Uiso 1 1 calc R . .
C4 C 0.83986(6) 0.33973(15) -0.23859(9) 0.0191(3) Uani 1 1 d . . .
H4 H 0.8396 0.3679 -0.2981 0.023 Uiso 1 1 calc R . .
C8 C 1.04429(6) 0.26763(16) 0.10347(10) 0.0210(3) Uani 1 1 d . . .
H8A H 1.0661 0.1586 0.1242 0.032 Uiso 1 1 calc R . .
H8B H 1.0801 0.3526 0.1308 0.032 Uiso 1 1 calc R . .
H8C H 1.0128 0.2748 0.0256 0.032 Uiso 1 1 calc R . .
C3 C 0.79705(6) 0.40670(15) -0.21367(9) 0.0187(2) Uani 1 1 d . . .
H3 H 0.7622 0.4875 -0.2537 0.022 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N4 C12 1.3813(14) . ?
N4 C9 1.3938(15) . ?
N4 N3 1.4152(13) . ?
N3 C7 1.4601(15) . ?
N3 C8 1.4669(16) . ?
N2 C3 1.3705(16) . ?
N2 C6 1.3849(15) . ?
N2 N1 1.4188(14) . ?
N1 C2 1.4670(16) . ?
N1 C1 1.4681(16) . ?
C12 C11 1.3778(15) . ?
C12 C12 1.465(2) 2_755 ?
C10 C9 1.3728(16) . ?
C10 C11 1.4167(17) . ?
C9 C6 1.4727(16) . ?
C6 C5 1.3795(16) . ?
C5 C4 1.4148(17) . ?
C4 C3 1.3709(17) . ?
C10 H10 0.930 . ?
C1 H1A 0.960 . ?
C1 H1B 0.960 . ?
C1 H1C 0.961 . ?
C5 H5 0.930 . ?
C7 H7A 0.960 . ?
C7 H7B 0.960 . ?
C7 H7C 0.961 . ?
C2 H2A 0.960 . ?
C2 H2B 0.960 . ?
C2 H2C 0.961 . ?
C11 H11 0.930 . ?
C4 H4 0.929 . ?
C8 H8A 0.960 . ?
C8 H8B 0.960 . ?
C8 H8C 0.960 . ?
C3 H3 0.929 . ?
C10 H10 0.930 . ?

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
C12 N4 C9 109.72(9) . . ?
C12 N4 N3 120.77(9) . . ?
C9 N4 N3 128.30(9) . . ?
N4 N3 C7 111.75(9) . . ?
N4 N3 C8 110.89(9) . . ?
C7 N3 C8 112.51(9) . . ?
C3 N2 C6 110.08(9) . . ?
C3 N2 N1 126.08(10) . . ?
C6 N2 N1 123.64(9) . . ?
N2 N1 C2 110.50(9) . . ?
N2 N1 C1 109.63(9) . . ?
C2 N1 C1 110.02(9) . . ?
C11 C12 N4 107.31(10) . . ?
C11 C12 C12 127.57(8) . 2_755 ?
N4 C12 C12 124.98(8) . 2_755 ?
C9 C10 C11 108.33(10) . . ?
C10 C9 N4 106.84(10) . . ?
C10 C9 C6 128.62(10) . . ?
N4 C9 C6 124.53(10) . . ?
C5 C6 N2 106.56(10) . . ?
C5 C6 C9 130.36(10) . . ?
N2 C6 C9 123.05(10) . . ?
C6 C5 C4 108.05(11) . . ?
C12 C11 C10 107.79(10) . . ?
C3 C4 C5 107.66(11) . . ?
N2 C3 C4 107.64(10) . . ?
H10 C10 C9 125.8 . . ?
H10 C10 C11 125.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.4 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 H5 126.0 . . ?
H5 C5 C4 126.0 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.4 . . ?
N3 C7 H7C 109.4 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.4 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.4 . . ?
H2B C2 H2C 109.6 . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
C5 C4 H4 126.2 . . ?
H4 C4 C3 126.1 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.4 . . ?
H8A C8 H8C 109.4 . . ?
H8B C8 H8C 109.5 . . ?
N2 C3 H3 126.2 . . ?
C4 C3 H3 126.1 . . ?
H10 C10 C9 125.8 . . ?
H10 C10 C11 125.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.4 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 H5 126.0 . . ?
H5 C5 C4 126.0 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.4 . . ?
N3 C7 H7C 109.4 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.4 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.4 . . ?
H2B C2 H2C 109.6 . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
C5 C4 H4 126.2 . . ?
H4 C4 C3 126.1 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.4 . . ?
H8A C8 H8C 109.4 . . ?
H8B C8 H8C 109.5 . . ?
N2 C3 H3 126.2 . . ?
C4 C3 H3 126.1 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_auto
_database_code_depnum_ccdc_archive 'CCDC 1027854'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-04T17:08:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C30 H42 N10'
_chemical_formula_moiety         'C30 H42 N10'
_chemical_formula_weight         542.74

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.347(5)
_cell_length_b                   13.899(9)
_cell_length_c                   14.203(9)
_cell_angle_alpha                106.524(6)
_cell_angle_beta                 95.771(6)
_cell_angle_gamma                105.689(6)
_cell_volume                     1492.6(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.57
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_number            11917
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_reflns_number_total             6569
_reflns_number_gt                4952
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0674P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6569
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.38
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
N8 N 0.62735(15) 0.40067(9) 0.10492(8) 0.0177(3) Uani 1 1 d . . .
N4 N 0.88603(15) 0.76987(9) 0.53839(9) 0.0184(3) Uani 1 1 d . . .
N6 N 0.67411(15) 0.53482(9) 0.33806(9) 0.0178(3) Uani 1 1 d . . .
N10 N 0.76382(15) 0.21577(10) -0.06353(9) 0.0207(3) Uani 1 1 d . . .
N005 N 0.76709(15) 0.48988(10) 0.11743(9) 0.0197(3) Uani 1 1 d . . .
N3 N 0.92697(16) 0.84241(9) 0.48500(9) 0.0206(3) Uani 1 1 d . . .
N2 N 1.24958(16) 0.93593(10) 0.69579(10) 0.0252(3) Uani 1 1 d . . .
N5 N 0.79136(16) 0.47828(10) 0.34112(9) 0.0223(3) Uani 1 1 d . . .
C21 C 0.52137(18) 0.40151(12) 0.17368(10) 0.0185(3) Uani 1 1 d . . .
N9 N 0.81080(17) 0.17762(11) 0.01412(10) 0.0254(3) Uani 1 1 d . . .
C27 C 0.65199(17) 0.27393(11) -0.05720(11) 0.0188(3) Uani 1 1 d . . .
C9 C 0.96262(18) 0.79861(11) 0.63774(10) 0.0196(3) Uani 1 1 d . . .
N1 N 1.33541(18) 0.86980(11) 0.64199(12) 0.0361(4) Uani 1 1 d . . .
C12 C 0.76243(18) 0.67182(11) 0.51068(10) 0.0185(3) Uani 1 1 d . . .
C22 C 0.40194(19) 0.30429(13) 0.14370(11) 0.0243(3) Uani 1 1 d . . .
H22 H 0.3143 0.2827 0.1761 0.029 Uiso 1 1 calc R . .
C15 C 0.64964(18) 0.61662(11) 0.41278(10) 0.0180(3) Uani 1 1 d . . .
C16 C 0.49639(18) 0.62659(12) 0.37788(11) 0.0209(3) Uani 1 1 d . . .
H16 H 0.4475 0.6757 0.4115 0.025 Uiso 1 1 calc R . .
C8 C 0.7970(2) 0.89296(12) 0.47546(13) 0.0275(4) Uani 1 1 d . . .
H8A H 0.7713 0.921 0.5401 0.041 Uiso 1 1 calc R . .
H8B H 0.6964 0.8419 0.4312 0.041 Uiso 1 1 calc R . .
H8C H 0.8377 0.9493 0.4488 0.041 Uiso 1 1 calc R . .
C23 C 0.43478(19) 0.24206(13) 0.05447(11) 0.0245(3) Uani 1 1 d . . .
H23 H 0.3728 0.1722 0.0183 0.029 Uiso 1 1 calc R . .
C10 C 0.88991(19) 0.71791(12) 0.67191(11) 0.0218(3) Uani 1 1 d . . .
H10 H 0.9183 0.7153 0.7359 0.026 Uiso 1 1 calc R . .
C18 C 0.53878(17) 0.49428(11) 0.25943(10) 0.0181(3) Uani 1 1 d . . .
C29 C 0.7286(2) 0.24518(12) -0.20776(11) 0.0247(3) Uani 1 1 d . . .
H29 H 0.7375 0.2462 -0.2722 0.03 Uiso 1 1 calc R . .
C6 C 1.07871(19) 0.90393(12) 0.69317(11) 0.0219(3) Uani 1 1 d . . .
C28 C 0.62799(19) 0.29187(12) -0.14659(11) 0.0224(3) Uani 1 1 d . . .
H28 H 0.5578 0.3283 -0.1641 0.027 Uiso 1 1 calc R . .
C19 C 0.92430(18) 0.46309(13) 0.11168(12) 0.0240(3) Uani 1 1 d . . .
H19A H 0.9376 0.4245 0.1566 0.036 Uiso 1 1 calc R . .
H19B H 1.0186 0.5268 0.1301 0.036 Uiso 1 1 calc R . .
H19C H 0.9199 0.4205 0.0445 0.036 Uiso 1 1 calc R . .
C24 C 0.57371(18) 0.30242(11) 0.03059(10) 0.0180(3) Uani 1 1 d . . .
C11 C 0.76464(19) 0.63948(12) 0.59369(11) 0.0218(3) Uani 1 1 d . . .
H11 H 0.6951 0.5764 0.5974 0.026 Uiso 1 1 calc R . .
C17 C 0.42654(18) 0.54983(11) 0.28266(11) 0.0199(3) Uani 1 1 d . . .
H17 H 0.3234 0.5388 0.2429 0.024 Uiso 1 1 calc R . .
C3 C 1.3209(2) 1.03928(12) 0.75652(12) 0.0285(4) Uani 1 1 d . . .
H3 H 1.4349 1.0786 0.7699 0.034 Uiso 1 1 calc R . .
C13 C 0.7487(2) 0.40996(13) 0.40161(12) 0.0320(4) Uani 1 1 d . . .
H13A H 0.6311 0.3687 0.3806 0.048 Uiso 1 1 calc R . .
H13B H 0.7697 0.4523 0.4707 0.048 Uiso 1 1 calc R . .
H13C H 0.8171 0.3637 0.3935 0.048 Uiso 1 1 calc R . .
C14 C 0.9672(2) 0.54513(13) 0.36592(12) 0.0299(4) Uani 1 1 d . . .
H14A H 0.9848 0.5876 0.3228 0.045 Uiso 1 1 calc R . .
H14B H 1.0401 0.5017 0.3571 0.045 Uiso 1 1 calc R . .
H14C H 0.9927 0.5903 0.4343 0.045 Uiso 1 1 calc R . .
C26 C 0.9924(2) 0.19346(15) 0.03199(13) 0.0316(4) Uani 1 1 d . . .
H26A H 1.0532 0.2672 0.0483 0.047 Uiso 1 1 calc R . .
H26B H 1.0221 0.154 -0.0271 0.047 Uiso 1 1 calc R . .
H26C H 1.0217 0.1697 0.0866 0.047 Uiso 1 1 calc R . .
C20 C 0.7354(2) 0.54933(12) 0.05140(12) 0.0259(3) Uani 1 1 d . . .
H20A H 0.6309 0.5645 0.0588 0.039 Uiso 1 1 calc R . .
H20B H 0.7278 0.5081 -0.0168 0.039 Uiso 1 1 calc R . .
H20C H 0.8268 0.6143 0.0688 0.039 Uiso 1 1 calc R . .
C30 C 0.81050(19) 0.19826(12) -0.15490(11) 0.0231(3) Uani 1 1 d . . .
H30 H 0.8845 0.1612 -0.1771 0.028 Uiso 1 1 calc R . .
C5 C 1.0427(2) 0.98860(13) 0.75440(12) 0.0287(4) Uani 1 1 d . . .
H5 H 0.9363 0.9897 0.7678 0.034 Uiso 1 1 calc R . .
C7 C 0.9734(2) 0.79802(14) 0.38990(12) 0.0295(4) Uani 1 1 d . . .
H7A H 1.059 0.7659 0.4003 0.044 Uiso 1 1 calc R . .
H7B H 1.0165 0.8532 0.3623 0.044 Uiso 1 1 calc R . .
H7C H 0.8753 0.7457 0.3444 0.044 Uiso 1 1 calc R . .
C2 C 1.3992(3) 0.91069(16) 0.56310(17) 0.0516(6) Uani 1 1 d . . .
H2A H 1.3064 0.9147 0.5203 0.077 Uiso 1 1 calc R . .
H2B H 1.4525 0.8641 0.5244 0.077 Uiso 1 1 calc R . .
H2C H 1.4803 0.9799 0.5934 0.077 Uiso 1 1 calc R . .
C25 C 0.7151(2) 0.06711(16) -0.01072(17) 0.0467(5) Uani 1 1 d . . .
H25A H 0.596 0.0586 -0.0222 0.07 Uiso 1 1 calc R . .
H25B H 0.7426 0.0426 0.0436 0.07 Uiso 1 1 calc R . .
H25C H 0.7432 0.0268 -0.0701 0.07 Uiso 1 1 calc R . .
C4 C 1.1953(2) 1.07364(13) 0.79343(12) 0.0286(4) Uani 1 1 d . . .
H4 H 1.2073 1.1407 0.8364 0.034 Uiso 1 1 calc R . .
C1 C 1.4703(3) 0.86203(18) 0.7092(2) 0.0677(8) Uani 1 1 d . . .
H1A H 1.4239 0.8352 0.7592 0.102 Uiso 1 1 calc R . .
H1B H 1.5521 0.9307 0.741 0.102 Uiso 1 1 calc R . .
H1C H 1.5244 0.815 0.6719 0.102 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N8 C21 1.3818(18) . ?
N8 C24 1.3908(19) . ?
N8 N005 1.4073(17) . ?
N4 C9 1.385(2) . ?
N4 C12 1.3891(19) . ?
N4 N3 1.4174(17) . ?
N6 C18 1.3729(19) . ?
N6 C15 1.3941(19) . ?
N6 N5 1.4157(17) . ?
N10 C30 1.367(2) . ?
N10 C27 1.3844(19) . ?
N10 N9 1.4176(18) . ?
N005 C19 1.461(2) . ?
N005 C20 1.463(2) . ?
N3 C7 1.455(2) . ?
N3 C8 1.458(2) . ?
N2 C6 1.368(2) . ?
N2 C3 1.375(2) . ?
N2 N1 1.4173(19) . ?
N5 C14 1.454(2) . ?
N5 C13 1.452(2) . ?
C21 C22 1.364(2) . ?
C21 C18 1.462(2) . ?
N9 C25 1.447(2) . ?
N9 C26 1.457(2) . ?
C27 C28 1.367(2) . ?
C27 C24 1.470(2) . ?
C9 C10 1.365(2) . ?
C9 C6 1.458(2) . ?
N1 C1 1.449(3) . ?
N1 C2 1.477(3) . ?
C12 C11 1.376(2) . ?
C12 C15 1.466(2) . ?
C22 C23 1.416(2) . ?
C15 C16 1.382(2) . ?
C16 C17 1.411(2) . ?
C23 C24 1.371(2) . ?
C10 C11 1.406(2) . ?
C18 C17 1.375(2) . ?
C29 C30 1.368(2) . ?
C29 C28 1.415(2) . ?
C6 C5 1.376(2) . ?
C3 C4 1.357(2) . ?
C5 C4 1.413(2) . ?
C22 H22 0.930 . ?
C16 H16 0.930 . ?
C8 H8A 0.960 . ?
C8 H8B 0.960 . ?
C8 H8C 0.961 . ?
C23 H23 0.930 . ?
C10 H10 0.929 . ?
C29 H29 0.929 . ?
C28 H28 0.930 . ?
C19 H19A 0.959 . ?
C19 H19B 0.960 . ?
C19 H19C 0.960 . ?
C11 H11 0.930 . ?
C17 H17 0.930 . ?
C3 H3 0.929 . ?
C13 H13A 0.960 . ?
C13 H13B 0.960 . ?
C13 H13C 0.960 . ?
C14 H14A 0.960 . ?
C14 H14B 0.960 . ?
C14 H14C 0.960 . ?
C26 H26A 0.960 . ?
C26 H26B 0.959 . ?
C26 H26C 0.960 . ?
C20 H20A 0.960 . ?
C20 H20B 0.961 . ?
C20 H20C 0.960 . ?
C30 H30 0.930 . ?
C5 H5 0.930 . ?
C7 H7A 0.959 . ?
C7 H7B 0.960 . ?
C7 H7C 0.960 . ?
C2 H2A 0.959 . ?
C2 H2B 0.960 . ?
C2 H2C 0.960 . ?
C25 H25A 0.960 . ?
C25 H25B 0.959 . ?
C25 H25C 0.960 . ?
C4 H4 0.930 . ?
C1 H1A 0.960 . ?
C1 H1B 0.960 . ?
C1 H1C 0.961 . ?

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
C21 N8 C24 109.56(12) . . ?
C21 N8 N005 120.77(12) . . ?
C24 N8 N005 129.66(11) . . ?
C9 N4 C12 109.71(11) . . ?
C9 N4 N3 119.88(12) . . ?
C12 N4 N3 130.06(12) . . ?
C18 N6 C15 109.86(12) . . ?
C18 N6 N5 118.59(12) . . ?
C15 N6 N5 130.13(12) . . ?
C30 N10 C27 109.91(12) . . ?
C30 N10 N9 127.48(13) . . ?
C27 N10 N9 122.53(12) . . ?
N8 N005 C19 111.86(12) . . ?
N8 N005 C20 112.30(12) . . ?
C19 N005 C20 113.60(11) . . ?
N4 N3 C7 113.33(12) . . ?
N4 N3 C8 112.28(11) . . ?
C7 N3 C8 112.78(13) . . ?
C6 N2 C3 110.02(13) . . ?
C6 N2 N1 123.37(13) . . ?
C3 N2 N1 126.61(14) . . ?
N6 N5 C14 113.29(13) . . ?
N6 N5 C13 110.84(12) . . ?
C14 N5 C13 114.69(13) . . ?
C22 C21 N8 107.50(13) . . ?
C22 C21 C18 128.93(13) . . ?
N8 C21 C18 123.53(13) . . ?
N10 N9 C25 109.71(13) . . ?
N10 N9 C26 111.09(12) . . ?
C25 N9 C26 110.97(14) . . ?
C28 C27 N10 106.87(12) . . ?
C28 C27 C24 129.98(14) . . ?
N10 C27 C24 123.08(13) . . ?
C10 C9 N4 107.17(13) . . ?
C10 C9 C6 129.43(14) . . ?
N4 C9 C6 122.74(13) . . ?
N2 N1 C1 110.57(16) . . ?
N2 N1 C2 109.24(14) . . ?
C1 N1 C2 112.00(18) . . ?
C11 C12 N4 106.42(13) . . ?
C11 C12 C15 127.54(14) . . ?
N4 C12 C15 126.01(12) . . ?
C21 C22 C23 107.96(13) . . ?
C16 C15 N6 106.24(13) . . ?
C16 C15 C12 129.14(13) . . ?
N6 C15 C12 124.44(13) . . ?
C15 C16 C17 108.57(13) . . ?
C24 C23 C22 108.24(14) . . ?
C9 C10 C11 108.26(14) . . ?
C17 C18 N6 107.84(13) . . ?
C17 C18 C21 129.51(13) . . ?
N6 C18 C21 122.41(13) . . ?
C30 C29 C28 107.64(14) . . ?
N2 C6 C5 106.58(14) . . ?
N2 C6 C9 125.21(13) . . ?
C5 C6 C9 128.19(15) . . ?
C27 C28 C29 108.01(14) . . ?
C23 C24 N8 106.73(12) . . ?
C23 C24 C27 128.40(14) . . ?
N8 C24 C27 124.84(12) . . ?
C12 C11 C10 108.42(14) . . ?
C18 C17 C16 107.49(13) . . ?
C4 C3 N2 107.89(15) . . ?
C29 C30 N10 107.57(13) . . ?
C6 C5 C4 108.23(15) . . ?
C3 C4 C5 107.29(15) . . ?
C21 C22 H22 126.0 . . ?
H22 C22 C23 126.0 . . ?
C15 C16 H16 125.7 . . ?
H16 C16 C17 125.7 . . ?
N3 C8 H8A 109.4 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.4 . . ?
C22 C23 H23 125.9 . . ?
H23 C23 C24 125.9 . . ?
C9 C10 H10 125.8 . . ?
H10 C10 C11 125.9 . . ?
H29 C29 C28 126.2 . . ?
H29 C29 C30 126.2 . . ?
C27 C28 H28 126.0 . . ?
C29 C28 H28 126.0 . . ?
N005 C19 H19A 109.4 . . ?
N005 C19 H19B 109.4 . . ?
N005 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C11 H11 125.8 . . ?
C10 C11 H11 125.8 . . ?
C16 C17 H17 126.3 . . ?
C18 C17 H17 126.3 . . ?
N2 C3 H3 126.1 . . ?
H3 C3 C4 126.1 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
N5 C14 H14C 109.4 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.4 . . ?
H14B C14 H14C 109.5 . . ?
N9 C26 H26A 109.5 . . ?
N9 C26 H26B 109.5 . . ?
N9 C26 H26C 109.5 . . ?
H26A C26 H26B 109.4 . . ?
H26A C26 H26C 109.4 . . ?
H26B C26 H26C 109.5 . . ?
N005 C20 H20A 109.5 . . ?
N005 C20 H20B 109.4 . . ?
N005 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.4 . . ?
N10 C30 H30 126.2 . . ?
C29 C30 H30 126.2 . . ?
C6 C5 H5 125.9 . . ?
H5 C5 C4 125.9 . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.4 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.4 . . ?
H2B C2 H2C 109.5 . . ?
N9 C25 H25A 109.5 . . ?
N9 C25 H25B 109.5 . . ?
N9 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.3 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.4 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_auto
_database_code_depnum_ccdc_archive 'CCDC 1027855'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-04T17:26:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C36 H50 N12'
_chemical_formula_moiety         'C36 H50 N12'
_chemical_formula_weight         650.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.659(5)
_cell_length_b                   13.191(5)
_cell_length_c                   18.976(5)
_cell_angle_alpha                77.128(5)
_cell_angle_beta                 83.248(5)
_cell_angle_gamma                79.800(5)
_cell_volume                     1833.3(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.57
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_number            14764
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_reflns_number_total             8016
_reflns_number_gt                4320
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1076P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8016
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2305
_refine_ls_wR_factor_gt          0.2028
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.5949(5) 1.1075(3) 0.51281(18) 0.0343(8) Uani 1 1 d . . .
H1A H 0.7038 1.0849 0.486 0.051 Uiso 1 1 calc R . .
H1B H 0.5987 1.175 0.5232 0.051 Uiso 1 1 calc R . .
H1C H 0.4964 1.1127 0.4846 0.051 Uiso 1 1 calc R . .
C2 C 0.4080(5) 1.0632(3) 0.6230(2) 0.0350(8) Uani 1 1 d . . .
H2A H 0.3963 1.0121 0.6674 0.052 Uiso 1 1 calc R . .
H2B H 0.3086 1.0681 0.5953 0.052 Uiso 1 1 calc R . .
H2C H 0.4106 1.1306 0.6339 0.052 Uiso 1 1 calc R . .
C3 C 0.7636(5) 1.0905(2) 0.65785(17) 0.0286(7) Uani 1 1 d . . .
H3 H 0.6962 1.1551 0.6621 0.034 Uiso 1 1 calc R . .
C4 C 0.9227(5) 1.0485(2) 0.68663(18) 0.0317(8) Uani 1 1 d . . .
H4 H 0.9823 1.079 0.7144 0.038 Uiso 1 1 calc R . .
C5 C 0.9804(4) 0.9496(2) 0.66637(17) 0.0281(7) Uani 1 1 d . . .
H5 H 1.085 0.9042 0.6783 0.034 Uiso 1 1 calc R . .
C6 C 0.8545(4) 0.9331(2) 0.62604(16) 0.0228(6) Uani 1 1 d . . .
C7 C 0.5638(5) 0.8020(2) 0.71581(18) 0.0308(8) Uani 1 1 d . . .
H7A H 0.476 0.8234 0.681 0.046 Uiso 1 1 calc R . .
H7B H 0.6146 0.8619 0.7196 0.046 Uiso 1 1 calc R . .
H7C H 0.5088 0.7726 0.7622 0.046 Uiso 1 1 calc R . .
C8 C 0.8443(5) 0.6851(3) 0.74173(17) 0.0318(8) Uani 1 1 d . . .
H8A H 0.9315 0.6336 0.7232 0.048 Uiso 1 1 calc R . .
H8B H 0.7942 0.6537 0.7886 0.048 Uiso 1 1 calc R . .
H8C H 0.8998 0.7431 0.7459 0.048 Uiso 1 1 calc R . .
C9 C 0.8496(4) 0.8467(2) 0.58893(15) 0.0205(6) Uani 1 1 d . . .
C10 C 0.9135(4) 0.8368(2) 0.51960(15) 0.0212(6) Uani 1 1 d . . .
H10 H 0.97 0.8855 0.4856 0.025 Uiso 1 1 calc R . .
C11 C 0.8787(4) 0.7400(2) 0.50873(16) 0.0215(6) Uani 1 1 d . . .
H11 H 0.9082 0.7138 0.4665 0.026 Uiso 1 1 calc R . .
C12 C 0.7928(4) 0.6912(2) 0.57204(16) 0.0194(6) Uani 1 1 d . . .
C13 C 0.3441(4) 0.6231(3) 0.5504(2) 0.0373(9) Uani 1 1 d . . .
H13A H 0.4261 0.6268 0.5079 0.056 Uiso 1 1 calc R . .
H13B H 0.2475 0.6805 0.5425 0.056 Uiso 1 1 calc R . .
H13C H 0.2985 0.5576 0.5603 0.056 Uiso 1 1 calc R . .
C14 C 0.3191(5) 0.6243(3) 0.6791(2) 0.0414(10) Uani 1 1 d . . .
H14A H 0.3849 0.6285 0.7181 0.062 Uiso 1 1 calc R . .
H14B H 0.2727 0.5591 0.6903 0.062 Uiso 1 1 calc R . .
H14C H 0.2225 0.682 0.6727 0.062 Uiso 1 1 calc R . .
C15 C 0.7565(4) 0.5827(2) 0.59199(15) 0.0190(6) Uani 1 1 d . . .
C16 C 0.8758(4) 0.4927(2) 0.58987(16) 0.0217(6) Uani 1 1 d . . .
H16 H 0.9957 0.4892 0.5737 0.026 Uiso 1 1 calc R . .
C17 C 0.7838(4) 0.4057(2) 0.61678(16) 0.0233(6) Uani 1 1 d . . .
H17 H 0.833 0.3351 0.6211 0.028 Uiso 1 1 calc R . .
C18 C 0.6095(4) 0.4438(2) 0.63530(15) 0.0202(6) Uani 1 1 d . . .
C19 C 0.5616(5) 0.4383(2) 0.80908(19) 0.0318(8) Uani 1 1 d . . .
H19A H 0.4444 0.4778 0.8136 0.048 Uiso 1 1 calc R . .
H19B H 0.6296 0.4743 0.7684 0.048 Uiso 1 1 calc R . .
H19C H 0.6193 0.4313 0.8525 0.048 Uiso 1 1 calc R . .
C20 C 0.7233(4) 0.2696(3) 0.79033(18) 0.0315(8) Uani 1 1 d . . .
H20A H 0.7081 0.2021 0.783 0.047 Uiso 1 1 calc R . .
H20B H 0.7833 0.2605 0.8335 0.047 Uiso 1 1 calc R . .
H20C H 0.793 0.3038 0.7494 0.047 Uiso 1 1 calc R . .
C21 C 0.4651(4) 0.3838(2) 0.66734(15) 0.0197(6) Uani 1 1 d . . .
C22 C 0.3335(4) 0.3587(2) 0.63427(16) 0.0226(6) Uani 1 1 d . . .
H22 H 0.3172 0.3779 0.585 0.027 Uiso 1 1 calc R . .
C23 C 0.2263(4) 0.2988(2) 0.68775(16) 0.0228(6) Uani 1 1 d . . .
H23 H 0.1267 0.2725 0.6801 0.027 Uiso 1 1 calc R . .
C24 C 0.2970(4) 0.2866(2) 0.75316(16) 0.0216(6) Uani 1 1 d . . .
C25 C 0.0141(5) 0.4227(3) 0.8870(2) 0.0397(9) Uani 1 1 d . . .
H25A H -0.0376 0.417 0.8446 0.06 Uiso 1 1 calc R . .
H25B H 0.0262 0.4947 0.8841 0.06 Uiso 1 1 calc R . .
H25C H -0.0614 0.3993 0.9295 0.06 Uiso 1 1 calc R . .
C26 C 0.2779(5) 0.3613(3) 0.95418(18) 0.0358(8) Uani 1 1 d . . .
H26A H 0.3921 0.3173 0.9539 0.054 Uiso 1 1 calc R . .
H26B H 0.2069 0.3366 0.9977 0.054 Uiso 1 1 calc R . .
H26C H 0.2935 0.4325 0.9524 0.054 Uiso 1 1 calc R . .
C27 C 0.2393(4) 0.2198(2) 0.82112(16) 0.0243(7) Uani 1 1 d . . .
C28 C 0.2062(4) 0.1182(2) 0.83071(16) 0.0246(7) Uani 1 1 d . . .
H28 H 0.23 0.0762 0.7963 0.029 Uiso 1 1 calc R . .
C29 C 0.1298(4) 0.0893(2) 0.90218(17) 0.0265(7) Uani 1 1 d . . .
H29 H 0.0954 0.0243 0.9231 0.032 Uiso 1 1 calc R . .
C30 C 0.1144(4) 0.1727(2) 0.93586(17) 0.0261(7) Uani 1 1 d . . .
C31 C 0.4458(5) 0.1226(3) 1.0975(2) 0.0419(9) Uani 1 1 d . . .
H31A H 0.4368 0.1976 1.0819 0.063 Uiso 1 1 calc R . .
H31B H 0.5665 0.0903 1.0882 0.063 Uiso 1 1 calc R . .
H31C H 0.4113 0.1053 1.1485 0.063 Uiso 1 1 calc R . .
C32 C 0.3393(5) -0.0303(3) 1.0799(2) 0.0399(9) Uani 1 1 d . . .
H32A H 0.2613 -0.0538 1.0529 0.06 Uiso 1 1 calc R . .
H32B H 0.3041 -0.0488 1.1307 0.06 Uiso 1 1 calc R . .
H32C H 0.4593 -0.0634 1.0704 0.06 Uiso 1 1 calc R . .
C33 C 0.0474(4) 0.1792(3) 1.01060(17) 0.0299(7) Uani 1 1 d . . .
C34 C -0.1166(5) 0.2175(3) 1.0396(2) 0.0382(8) Uani 1 1 d . . .
H34 H -0.2135 0.2517 1.0136 0.046 Uiso 1 1 calc R . .
C35 C -0.1131(5) 0.1961(3) 1.1162(2) 0.0448(10) Uani 1 1 d . . .
H35 H -0.2061 0.2145 1.1494 0.054 Uiso 1 1 calc R . .
C36 C 0.0537(5) 0.1429(3) 1.13206(19) 0.0382(9) Uani 1 1 d . . .
H36 H 0.0934 0.1176 1.1781 0.046 Uiso 1 1 calc R . .
N1 N 0.5734(3) 1.03088(19) 0.58098(14) 0.0251(6) Uani 1 1 d . . .
N2 N 0.7214(3) 1.01992(18) 0.62154(14) 0.0240(6) Uani 1 1 d . . .
N3 N 0.7037(3) 0.72294(19) 0.69236(13) 0.0248(6) Uani 1 1 d . . .
N4 N 0.7736(3) 0.75644(18) 0.62056(13) 0.0207(5) Uani 1 1 d . . .
N5 N 0.4361(3) 0.62952(19) 0.61249(15) 0.0271(6) Uani 1 1 d . . .
N6 N 0.5935(3) 0.55361(18) 0.61974(13) 0.0205(5) Uani 1 1 d . . .
N7 N 0.5488(3) 0.3344(2) 0.79797(14) 0.0253(6) Uani 1 1 d . . .
N8 N 0.4424(3) 0.33846(19) 0.74113(13) 0.0209(5) Uani 1 1 d . . .
N9 N 0.1890(4) 0.3575(2) 0.89136(15) 0.0291(6) Uani 1 1 d . . .
N10 N 0.1844(3) 0.25293(19) 0.88566(14) 0.0254(6) Uani 1 1 d . . .
N11 N 0.3288(4) 0.0839(2) 1.05775(14) 0.0288(6) Uani 1 1 d . . .
N12 N 0.1507(4) 0.1339(2) 1.06775(14) 0.0311(6) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.466(4) . ?
C2 N1 1.465(4) . ?
C3 C4 1.368(5) . ?
C3 N2 1.375(4) . ?
C4 C5 1.422(5) . ?
C5 C6 1.373(4) . ?
C6 N2 1.386(4) . ?
C6 C9 1.476(4) . ?
C7 N3 1.460(4) . ?
C8 N3 1.458(4) . ?
C9 C10 1.375(4) . ?
C9 N4 1.400(3) . ?
C10 C11 1.412(4) . ?
C11 C12 1.382(4) . ?
C12 N4 1.373(4) . ?
C12 C15 1.465(4) . ?
C13 N5 1.467(4) . ?
C14 N5 1.457(4) . ?
C15 C16 1.368(4) . ?
C15 N6 1.381(3) . ?
C16 C17 1.420(4) . ?
C17 C18 1.375(4) . ?
C18 N6 1.398(4) . ?
C18 C21 1.469(4) . ?
C19 N7 1.453(4) . ?
C20 N7 1.464(4) . ?
C21 C22 1.371(4) . ?
C21 N8 1.398(3) . ?
C22 C23 1.416(4) . ?
C23 C24 1.377(4) . ?
C24 N8 1.379(4) . ?
C24 C27 1.460(4) . ?
C25 N9 1.458(4) . ?
C26 N9 1.455(4) . ?
C27 C28 1.376(4) . ?
C27 N10 1.386(4) . ?
C28 C29 1.411(4) . ?
C29 C30 1.372(5) . ?
C30 N10 1.395(4) . ?
C30 C33 1.466(4) . ?
C31 N11 1.457(4) . ?
C32 N11 1.461(4) . ?
C33 C34 1.368(5) . ?
C33 N12 1.380(4) . ?
C34 C35 1.420(5) . ?
C35 C36 1.376(5) . ?
C36 N12 1.369(4) . ?
N1 N2 1.413(3) . ?
N3 N4 1.408(3) . ?
N5 N6 1.423(3) . ?
N7 N8 1.413(3) . ?
N9 N10 1.414(4) . ?
N11 N12 1.417(4) . ?
C1 H1A 0.961 . ?
C1 H1B 0.960 . ?
C1 H1C 0.960 . ?
C2 H2A 0.961 . ?
C2 H2B 0.960 . ?
C2 H2C 0.961 . ?
C3 H3 0.930 . ?
C4 H4 0.930 . ?
C5 H5 0.930 . ?
C7 H7A 0.960 . ?
C7 H7B 0.960 . ?
C7 H7C 0.960 . ?
C8 H8A 0.960 . ?
C8 H8B 0.960 . ?
C8 H8C 0.960 . ?
C10 H10 0.930 . ?
C11 H11 0.930 . ?
C13 H13A 0.960 . ?
C13 H13B 0.959 . ?
C13 H13C 0.961 . ?
C14 H14A 0.959 . ?
C14 H14B 0.959 . ?
C14 H14C 0.960 . ?
C16 H16 0.930 . ?
C17 H17 0.930 . ?
C19 H19A 0.960 . ?
C19 H19B 0.960 . ?
C19 H19C 0.959 . ?
C20 H20A 0.960 . ?
C20 H20B 0.960 . ?
C20 H20C 0.961 . ?
C22 H22 0.930 . ?
C23 H23 0.930 . ?
C25 H25A 0.960 . ?
C25 H25B 0.959 . ?
C25 H25C 0.961 . ?
C26 H26A 0.960 . ?
C26 H26B 0.960 . ?
C26 H26C 0.960 . ?
C28 H28 0.929 . ?
C29 H29 0.931 . ?
C31 H31A 0.960 . ?
C31 H31B 0.961 . ?
C31 H31C 0.960 . ?
C32 H32A 0.961 . ?
C32 H32B 0.959 . ?
C32 H32C 0.960 . ?
C34 H34 0.931 . ?
C35 H35 0.930 . ?
C36 H36 0.929 . ?

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 C3 N2 107.7(3) . . ?
C3 C4 C5 107.6(3) . . ?
C6 C5 C4 108.0(3) . . ?
C5 C6 N2 106.9(3) . . ?
C5 C6 C9 131.1(3) . . ?
N2 C6 C9 121.9(3) . . ?
C10 C9 N4 106.7(3) . . ?
C10 C9 C6 129.1(3) . . ?
N4 C9 C6 124.2(3) . . ?
C9 C10 C11 108.4(2) . . ?
C12 C11 C10 107.7(3) . . ?
N4 C12 C11 107.6(2) . . ?
N4 C12 C15 123.3(2) . . ?
C11 C12 C15 128.2(3) . . ?
C16 C15 N6 107.9(2) . . ?
C16 C15 C12 127.2(3) . . ?
N6 C15 C12 124.9(3) . . ?
C15 C16 C17 107.8(3) . . ?
C18 C17 C16 108.2(3) . . ?
C17 C18 N6 106.8(2) . . ?
C17 C18 C21 128.1(3) . . ?
N6 C18 C21 125.1(3) . . ?
C22 C21 N8 107.0(2) . . ?
C22 C21 C18 129.4(3) . . ?
N8 C21 C18 123.6(3) . . ?
C21 C22 C23 108.6(3) . . ?
C24 C23 C22 107.3(3) . . ?
C23 C24 N8 108.1(2) . . ?
C23 C24 C27 125.2(3) . . ?
N8 C24 C27 126.4(3) . . ?
C28 C27 N10 107.4(3) . . ?
C28 C27 C24 126.8(3) . . ?
N10 C27 C24 125.3(3) . . ?
C27 C28 C29 107.7(3) . . ?
C30 C29 C28 108.8(3) . . ?
C29 C30 N10 106.6(3) . . ?
C29 C30 C33 128.8(3) . . ?
N10 C30 C33 124.6(3) . . ?
C34 C33 N12 107.1(3) . . ?
C34 C33 C30 131.5(3) . . ?
N12 C33 C30 121.1(3) . . ?
C33 C34 C35 108.1(3) . . ?
C36 C35 C34 107.1(3) . . ?
N12 C36 C35 107.6(3) . . ?
N2 N1 C1 109.7(2) . . ?
N2 N1 C2 110.6(3) . . ?
C1 N1 C2 110.7(3) . . ?
C3 N2 C6 109.8(3) . . ?
C3 N2 N1 128.1(3) . . ?
C6 N2 N1 121.9(2) . . ?
N4 N3 C8 111.5(2) . . ?
N4 N3 C7 112.2(2) . . ?
C8 N3 C7 113.8(3) . . ?
C12 N4 C9 109.6(2) . . ?
C12 N4 N3 120.2(2) . . ?
C9 N4 N3 129.8(2) . . ?
N6 N5 C14 113.1(2) . . ?
N6 N5 C13 110.7(3) . . ?
C14 N5 C13 112.4(3) . . ?
C15 N6 C18 109.3(2) . . ?
C15 N6 N5 120.0(2) . . ?
C18 N6 N5 128.6(2) . . ?
N8 N7 C19 112.7(2) . . ?
N8 N7 C20 112.6(2) . . ?
C19 N7 C20 112.5(3) . . ?
C24 N8 C21 109.1(2) . . ?
C24 N8 N7 120.9(2) . . ?
C21 N8 N7 129.9(2) . . ?
N10 N9 C26 112.0(2) . . ?
N10 N9 C25 112.4(3) . . ?
C26 N9 C25 113.4(3) . . ?
C27 N10 C30 109.5(3) . . ?
C27 N10 N9 120.9(2) . . ?
C30 N10 N9 129.3(3) . . ?
N12 N11 C31 110.7(3) . . ?
N12 N11 C32 110.3(3) . . ?
C31 N11 C32 111.1(3) . . ?
C36 N12 C33 110.0(3) . . ?
C36 N12 N11 127.4(3) . . ?
C33 N12 N11 122.6(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.4 . . ?
H1A C1 N1 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 N1 109.4 . . ?
H1C C1 N1 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2A C2 N1 109.5 . . ?
H2B C2 H2C 109.4 . . ?
H2B C2 N1 109.5 . . ?
H2C C2 N1 109.5 . . ?
H3 C3 C4 126.2 . . ?
H3 C3 N2 126.2 . . ?
C3 C4 H4 126.2 . . ?
H4 C4 C5 126.2 . . ?
C4 C5 H5 126.0 . . ?
H5 C5 C6 126.0 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7A C7 N3 109.4 . . ?
H7B C7 H7C 109.5 . . ?
H7B C7 N3 109.5 . . ?
H7C C7 N3 109.5 . . ?
H8A C8 H8B 109.4 . . ?
H8A C8 H8C 109.5 . . ?
H8A C8 N3 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H8B C8 N3 109.5 . . ?
H8C C8 N3 109.4 . . ?
C9 C10 H10 125.9 . . ?
H10 C10 C11 125.7 . . ?
C10 C11 H11 126.1 . . ?
H11 C11 C12 126.1 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13A C13 N5 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13B C13 N5 109.5 . . ?
H13C C13 N5 109.3 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14A C14 N5 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14B C14 N5 109.5 . . ?
H14C C14 N5 109.4 . . ?
C15 C16 H16 126.1 . . ?
H16 C16 C17 126.1 . . ?
C16 C17 H17 125.9 . . ?
H17 C17 C18 125.9 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19A C19 N7 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19B C19 N7 109.4 . . ?
H19C C19 N7 109.4 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20A C20 N7 109.5 . . ?
H20B C20 H20C 109.4 . . ?
H20B C20 N7 109.5 . . ?
H20C C20 N7 109.5 . . ?
C21 C22 H22 125.7 . . ?
H22 C22 C23 125.7 . . ?
C22 C23 H23 126.3 . . ?
H23 C23 C24 126.4 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25A C25 N9 109.5 . . ?
H25B C25 H25C 109.4 . . ?
H25B C25 N9 109.4 . . ?
H25C C25 N9 109.4 . . ?
H26A C26 H26B 109.4 . . ?
H26A C26 H26C 109.5 . . ?
H26A C26 N9 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H26B C26 N9 109.5 . . ?
H26C C26 N9 109.5 . . ?
C27 C28 H28 126.2 . . ?
H28 C28 C29 126.2 . . ?
C28 C29 H29 125.6 . . ?
H29 C29 C30 125.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31A C31 N11 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H31B C31 N11 109.4 . . ?
H31C C31 N11 109.5 . . ?
H32A C32 H32B 109.4 . . ?
H32A C32 H32C 109.4 . . ?
H32A C32 N11 109.4 . . ?
H32B C32 H32C 109.5 . . ?
H32B C32 N11 109.6 . . ?
H32C C32 N11 109.5 . . ?
C33 C34 H34 125.9 . . ?
H34 C34 C35 126.0 . . ?
C34 C35 H35 126.4 . . ?
H35 C35 C36 126.4 . . ?
C35 C36 H36 126.2 . . ?
H36 C36 N12 126.1 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
