# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_bo2979

_audit_creation_method           SHELXL-97
_chemical_name_systematic        HANTT
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H5 N9 O3'
_chemical_formula_weight         215.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.830(4)
_cell_length_b                   5.0641(18)
_cell_length_c                   15.865(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.122(4)
_cell_angle_gamma                90.00
_cell_volume                     835.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2855
_cell_measurement_theta_min      2.659
_cell_measurement_theta_max      29.123

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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            8220
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         29.13
_reflns_number_total             2245
_reflns_number_gt                1916
_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)+(0.0671P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2245
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44264(11) 0.3517(2) 0.28998(7) 0.0358(3) Uani 1 1 d . . .
O2 O 0.29507(11) 0.6529(2) 0.26381(7) 0.0402(3) Uani 1 1 d . . .
N1 N 0.26959(10) 0.4518(2) 0.50264(7) 0.0213(3) Uani 1 1 d . . .
N2 N 0.25678(10) 0.5696(2) 0.42227(7) 0.0222(3) Uani 1 1 d . . .
N3 N 0.41016(10) 0.2482(2) 0.44805(7) 0.0220(3) Uani 1 1 d . . .
N4 N 0.39890(13) 0.1108(3) 0.58860(8) 0.0297(3) Uani 1 1 d . . .
N5 N 0.36125(11) 0.4853(2) 0.31016(8) 0.0253(3) Uani 1 1 d . . .
N6 N 0.18900(11) 0.3844(2) 0.62649(7) 0.0236(3) Uani 1 1 d . . .
N7 N 0.10351(10) 0.5094(2) 0.65783(7) 0.0239(3) Uani 1 1 d . . .
N8 N 0.06075(10) 0.7096(2) 0.60553(7) 0.0232(3) Uani 1 1 d . . .
N9 N 0.11294(11) 0.7304(2) 0.53877(8) 0.0231(3) Uani 1 1 d . . .
C1 C 0.36223(12) 0.2585(3) 0.51728(8) 0.0210(3) Uani 1 1 d . . .
C2 C 0.34215(12) 0.4367(3) 0.39611(8) 0.0211(3) Uani 1 1 d . . .
C3 C 0.19121(12) 0.5237(3) 0.55526(8) 0.0203(3) Uani 1 1 d . . .
O3 O -0.11192(11) 0.9749(2) 0.65608(8) 0.0306(3) Uani 1 1 d . . .
H3A H -0.105(2) 0.984(4) 0.7098(16) 0.052(6) Uiso 1 1 d . . .
H3B H -0.146(2) 1.121(5) 0.6313(14) 0.054(6) Uiso 1 1 d . . .
H4A H 0.4605(18) -0.017(4) 0.5908(12) 0.038(5) Uiso 1 1 d . . .
H4B H 0.3654(17) 0.129(4) 0.6291(12) 0.036(5) Uiso 1 1 d . . .
H8 H -0.0044(19) 0.832(4) 0.6212(13) 0.053(6) 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
O1 N5 1.2222(15) . ?
O2 N5 1.2176(16) . ?
N1 C1 1.3746(16) . ?
N1 N2 1.3793(15) . ?
N1 C3 1.3939(15) . ?
N2 C2 1.3013(16) . ?
N3 C1 1.3399(16) . ?
N3 C2 1.3400(17) . ?
N4 C1 1.3220(18) . ?
N4 H4A 0.924(19) . ?
N4 H4B 0.827(18) . ?
N5 C2 1.4558(17) . ?
N6 N7 1.3270(15) . ?
N6 C3 1.3381(17) . ?
N7 N8 1.3105(17) . ?
N8 N9 1.3360(15) . ?
N8 H8 1.02(2) . ?
N9 C3 1.3267(17) . ?
O3 H3A 0.84(2) . ?
O3 H3B 0.87(2) . ?

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 110.21(10) . . ?
C1 N1 C3 128.46(12) . . ?
N2 N1 C3 121.27(11) . . ?
C2 N2 N1 99.98(10) . . ?
C1 N3 C2 101.78(10) . . ?
C1 N4 H4A 118.1(11) . . ?
C1 N4 H4B 120.7(13) . . ?
H4A N4 H4B 121.2(17) . . ?
O2 N5 O1 125.05(12) . . ?
O2 N5 C2 118.07(11) . . ?
O1 N5 C2 116.88(11) . . ?
N7 N6 C3 104.06(11) . . ?
N8 N7 N6 107.00(10) . . ?
N7 N8 N9 114.22(11) . . ?
N7 N8 H8 117.5(11) . . ?
N9 N8 H8 128.3(11) . . ?
C3 N9 N8 99.73(11) . . ?
N4 C1 N3 125.92(12) . . ?
N4 C1 N1 125.40(11) . . ?
N3 C1 N1 108.67(11) . . ?
N2 C2 N3 119.36(12) . . ?
N2 C2 N5 120.64(11) . . ?
N3 C2 N5 119.97(11) . . ?
N9 C3 N6 114.99(11) . . ?
N9 C3 N1 123.36(12) . . ?
N6 C3 N1 121.65(12) . . ?
H3A O3 H3B 108.5(19) . . ?

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 C2 0.13(14) . . . . ?
C3 N1 N2 C2 -177.22(12) . . . . ?
C3 N6 N7 N8 0.00(14) . . . . ?
N6 N7 N8 N9 -0.10(15) . . . . ?
N7 N8 N9 C3 0.16(14) . . . . ?
C2 N3 C1 N4 -179.26(14) . . . . ?
C2 N3 C1 N1 -0.23(14) . . . . ?
N2 N1 C1 N4 179.10(14) . . . . ?
C3 N1 C1 N4 -3.8(2) . . . . ?
N2 N1 C1 N3 0.07(15) . . . . ?
C3 N1 C1 N3 177.17(13) . . . . ?
N1 N2 C2 N3 -0.31(16) . . . . ?
N1 N2 C2 N5 177.73(12) . . . . ?
C1 N3 C2 N2 0.36(16) . . . . ?
C1 N3 C2 N5 -177.70(12) . . . . ?
O2 N5 C2 N2 -0.1(2) . . . . ?
O1 N5 C2 N2 -179.59(13) . . . . ?
O2 N5 C2 N3 177.92(13) . . . . ?
O1 N5 C2 N3 -1.6(2) . . . . ?
N8 N9 C3 N6 -0.16(15) . . . . ?
N8 N9 C3 N1 179.15(12) . . . . ?
N7 N6 C3 N9 0.11(15) . . . . ?
N7 N6 C3 N1 -179.21(12) . . . . ?
C1 N1 C3 N9 173.46(13) . . . . ?
N2 N1 C3 N9 -9.7(2) . . . . ?
C1 N1 C3 N6 -7.3(2) . . . . ?
N2 N1 C3 N6 169.55(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 1017630'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_bo3184

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 N12 O2.50'
_chemical_formula_weight         265.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0181(17)
_cell_length_b                   8.833(2)
_cell_length_c                   18.795(6)
_cell_angle_alpha                84.760(9)
_cell_angle_beta                 84.240(8)
_cell_angle_gamma                68.063(9)
_cell_volume                     1073.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    4312
_cell_measurement_theta_min      2.182
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            16124
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         31.51
_reflns_number_total             7031
_reflns_number_gt                5120
_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)+(0.0391P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7031
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O 0.56137(13) 0.80783(11) 0.31962(4) 0.0343(2) Uani 1 1 d . . .
O2 O 0.60579(13) 0.70424(10) 0.42898(4) 0.03183(19) Uani 1 1 d . . .
O3 O 0.76348(15) -0.11342(11) 0.18073(5) 0.0410(2) Uani 1 1 d . . .
O4 O 0.75631(14) -0.16037(10) 0.06969(5) 0.0371(2) Uani 1 1 d . . .
O5 O 0.90860(15) 0.52267(11) 0.25443(5) 0.02940(19) Uani 1 1 d . . .
N1 N 0.26655(13) 1.08861(11) 0.36486(5) 0.02172(18) Uani 1 1 d . . .
N2 N 0.29966(13) 0.96876(10) 0.47817(5) 0.02074(18) Uani 1 1 d . . .
N3 N 0.15022(13) 1.12327(10) 0.47782(4) 0.02011(18) Uani 1 1 d . . .
N4 N 0.00064(16) 1.34304(12) 0.39298(5) 0.0259(2) Uani 1 1 d . . .
N5 N 0.52095(14) 0.81253(11) 0.38451(5) 0.02353(19) Uani 1 1 d . . .
N6 N 0.06171(14) 1.10305(11) 0.60350(5) 0.0244(2) Uani 1 1 d . . .
N7 N -0.08091(15) 1.20679(12) 0.64828(5) 0.0283(2) Uani 1 1 d . . .
N8 N -0.18197(15) 1.34239(12) 0.61206(5) 0.0290(2) Uani 1 1 d . . .
N9 N -0.11128(14) 1.33445(11) 0.54234(5) 0.0263(2) Uani 1 1 d . . .
N10 N 0.75304(14) 0.19406(11) 0.14358(5) 0.0245(2) Uani 1 1 d . . .
N11 N 0.75818(14) 0.13608(11) 0.02755(5) 0.02366(19) Uani 1 1 d . . .
N12 N 0.75848(14) 0.29064(11) 0.03150(4) 0.02203(19) Uani 1 1 d . . .
N13 N 0.74916(16) 0.46579(13) 0.12223(6) 0.0298(2) Uani 1 1 d . . .
N14 N 0.75839(15) -0.07363(12) 0.11673(5) 0.0280(2) Uani 1 1 d . . .
N15 N 0.78026(16) 0.34182(12) -0.09578(5) 0.0296(2) Uani 1 1 d . . .
N16 N 0.76921(17) 0.47720(13) -0.13763(5) 0.0337(2) Uani 1 1 d . . .
N17 N 0.74207(16) 0.59796(13) -0.09725(5) 0.0333(2) Uani 1 1 d . . .
N18 N 0.73393(15) 0.54696(12) -0.02754(5) 0.0297(2) Uani 1 1 d . . .
N19 N 0.53145(16) 0.30838(13) 0.40125(5) 0.0267(2) Uani 1 1 d . . .
N20 N 0.70800(16) 0.16537(12) 0.30382(6) 0.0294(2) Uani 1 1 d . . .
N21 N 0.44897(17) 0.41614(13) 0.28799(6) 0.0328(2) Uani 1 1 d . . .
N22 N 0.25136(18) 0.13683(14) 0.20904(5) 0.0328(2) Uani 1 1 d . . .
N23 N 0.26095(17) 0.05252(14) 0.09688(5) 0.0300(2) Uani 1 1 d . . .
N24 N 0.23359(18) -0.11325(14) 0.19571(6) 0.0334(2) Uani 1 1 d . . .
C1 C 0.13191(16) 1.19389(13) 0.40948(5) 0.0200(2) Uani 1 1 d . . .
C2 C 0.35868(16) 0.96038(13) 0.40992(5) 0.0199(2) Uani 1 1 d . . .
C3 C 0.03549(16) 1.18649(12) 0.54095(5) 0.0198(2) Uani 1 1 d . . .
C4 C 0.75523(16) 0.32387(13) 0.10154(5) 0.0223(2) Uani 1 1 d . . .
C5 C 0.75574(16) 0.08950(13) 0.09521(5) 0.0228(2) Uani 1 1 d . . .
C6 C 0.75785(16) 0.39161(13) -0.03044(5) 0.0214(2) Uani 1 1 d . . .
C7 C 0.56442(17) 0.29531(13) 0.33069(5) 0.0219(2) Uani 1 1 d . . .
C8 C 0.24844(17) 0.02481(14) 0.16771(6) 0.0241(2) Uani 1 1 d . . .
H4A H -0.009(2) 1.3851(16) 0.3470(7) 0.034(4) Uiso 1 1 d . . .
H4B H -0.076(2) 1.4033(18) 0.4251(8) 0.041(4) Uiso 1 1 d . . .
H13A H 0.755(2) 0.5486(17) 0.0890(7) 0.038(4) Uiso 1 1 d . . .
H13B H 0.766(2) 0.4733(19) 0.1666(9) 0.052(5) Uiso 1 1 d . . .
H19A H 0.435(2) 0.3992(19) 0.4168(8) 0.045(4) Uiso 1 1 d . . .
H19B H 0.597(2) 0.2320(19) 0.4304(8) 0.046(4) Uiso 1 1 d . . .
H20A H 0.783(2) 0.0811(19) 0.3333(8) 0.052(5) Uiso 1 1 d . . .
H20B H 0.728(2) 0.1609(16) 0.2579(8) 0.037(4) Uiso 1 1 d . . .
H21A H 0.350(2) 0.503(2) 0.3076(8) 0.051(4) Uiso 1 1 d . . .
H21B H 0.466(2) 0.4158(18) 0.2408(8) 0.046(4) Uiso 1 1 d . . .
H22A H 0.261(2) 0.1164(17) 0.2578(8) 0.042(4) Uiso 1 1 d . . .
H22B H 0.259(2) 0.225(2) 0.1891(8) 0.052(5) Uiso 1 1 d . . .
H23A H 0.258(2) -0.0213(18) 0.0701(8) 0.043(4) Uiso 1 1 d . . .
H23B H 0.266(2) 0.149(2) 0.0787(8) 0.061(5) Uiso 1 1 d . . .
H24A H 0.231(2) -0.1833(18) 0.1664(8) 0.044(4) Uiso 1 1 d . . .
H24B H 0.211(2) -0.1260(19) 0.2409(9) 0.049(4) Uiso 1 1 d . . .
H05A H 0.820(3) 0.615(2) 0.2672(9) 0.058(5) Uiso 1 1 d . . .
H05B H 0.994(3) 0.540(2) 0.2284(9) 0.062(6) 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
O1 N5 1.2250(12) . ?
O2 N5 1.2233(12) . ?
O3 N14 1.2223(12) . ?
O4 N14 1.2262(13) . ?
O5 H05A 0.858(17) . ?
O5 H05B 0.785(17) . ?
N1 C1 1.3371(13) . ?
N1 C2 1.3439(13) . ?
N2 C2 1.3078(13) . ?
N2 N3 1.3759(12) . ?
N3 C1 1.3721(13) . ?
N3 C3 1.4004(13) . ?
N4 C1 1.3253(14) . ?
N4 H4A 0.907(14) . ?
N4 H4B 0.847(15) . ?
N5 C2 1.4574(14) . ?
N6 C3 1.3203(13) . ?
N6 N7 1.3551(13) . ?
N7 N8 1.3094(14) . ?
N8 N9 1.3523(13) . ?
N9 C3 1.3285(13) . ?
N10 C4 1.3359(14) . ?
N10 C5 1.3479(14) . ?
N11 C5 1.3008(13) . ?
N11 N12 1.3748(13) . ?
N12 C4 1.3709(13) . ?
N12 C6 1.3997(13) . ?
N13 C4 1.3305(15) . ?
N13 H13A 0.929(14) . ?
N13 H13B 0.865(16) . ?
N14 C5 1.4544(15) . ?
N15 C6 1.3171(14) . ?
N15 N16 1.3513(14) . ?
N16 N17 1.3104(15) . ?
N17 N18 1.3488(14) . ?
N18 C6 1.3243(14) . ?
N19 C7 1.3313(14) . ?
N19 H19A 0.886(15) . ?
N19 H19B 0.847(16) . ?
N20 C7 1.3143(14) . ?
N20 H20A 0.911(16) . ?
N20 H20B 0.863(14) . ?
N21 C7 1.3295(14) . ?
N21 H21A 0.901(16) . ?
N21 H21B 0.883(15) . ?
N22 C8 1.3198(15) . ?
N22 H22A 0.923(15) . ?
N22 H22B 0.855(16) . ?
N23 C8 1.3315(14) . ?
N23 H23A 0.867(15) . ?
N23 H23B 0.901(17) . ?
N24 C8 1.3198(15) . ?
N24 H24A 0.872(16) . ?
N24 H24B 0.853(16) . ?

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
H05A O5 H05B 108.2(17) . . ?
C1 N1 C2 101.89(9) . . ?
C2 N2 N3 99.99(8) . . ?
C1 N3 N2 110.44(8) . . ?
C1 N3 C3 128.50(9) . . ?
N2 N3 C3 121.01(8) . . ?
C1 N4 H4A 121.3(9) . . ?
C1 N4 H4B 121.1(10) . . ?
H4A N4 H4B 117.6(13) . . ?
O2 N5 O1 125.35(9) . . ?
O2 N5 C2 118.10(9) . . ?
O1 N5 C2 116.55(9) . . ?
C3 N6 N7 103.18(9) . . ?
N8 N7 N6 109.33(9) . . ?
N7 N8 N9 110.40(9) . . ?
C3 N9 N8 102.46(9) . . ?
C4 N10 C5 101.82(9) . . ?
C5 N11 N12 100.32(9) . . ?
C4 N12 N11 110.28(8) . . ?
C4 N12 C6 128.73(9) . . ?
N11 N12 C6 120.97(9) . . ?
C4 N13 H13A 121.2(9) . . ?
C4 N13 H13B 118.8(10) . . ?
H13A N13 H13B 118.8(13) . . ?
O3 N14 O4 125.19(11) . . ?
O3 N14 C5 116.91(10) . . ?
O4 N14 C5 117.90(9) . . ?
C6 N15 N16 103.17(9) . . ?
N17 N16 N15 109.56(9) . . ?
N16 N17 N18 109.89(10) . . ?
C6 N18 N17 102.89(9) . . ?
C7 N19 H19A 117.3(10) . . ?
C7 N19 H19B 121.7(10) . . ?
H19A N19 H19B 120.9(13) . . ?
C7 N20 H20A 120.3(9) . . ?
C7 N20 H20B 118.7(9) . . ?
H20A N20 H20B 120.9(12) . . ?
C7 N21 H21A 119.1(10) . . ?
C7 N21 H21B 122.8(10) . . ?
H21A N21 H21B 118.1(14) . . ?
C8 N22 H22A 121.5(9) . . ?
C8 N22 H22B 118.3(10) . . ?
H22A N22 H22B 119.8(14) . . ?
C8 N23 H23A 118.5(10) . . ?
C8 N23 H23B 118.8(10) . . ?
H23A N23 H23B 122.6(14) . . ?
C8 N24 H24A 117.8(10) . . ?
C8 N24 H24B 119.9(10) . . ?
H24A N24 H24B 121.7(14) . . ?
N4 C1 N1 127.42(10) . . ?
N4 C1 N3 123.79(10) . . ?
N1 C1 N3 108.79(9) . . ?
N2 C2 N1 118.89(9) . . ?
N2 C2 N5 119.45(9) . . ?
N1 C2 N5 121.66(9) . . ?
N6 C3 N9 114.64(9) . . ?
N6 C3 N3 122.83(9) . . ?
N9 C3 N3 122.53(9) . . ?
N13 C4 N10 127.12(10) . . ?
N13 C4 N12 124.01(10) . . ?
N10 C4 N12 108.85(9) . . ?
N11 C5 N10 118.73(10) . . ?
N11 C5 N14 119.53(10) . . ?
N10 C5 N14 121.75(9) . . ?
N15 C6 N18 114.50(10) . . ?
N15 C6 N12 123.55(10) . . ?
N18 C6 N12 121.96(10) . . ?
N20 C7 N21 120.71(10) . . ?
N20 C7 N19 120.62(10) . . ?
N21 C7 N19 118.67(10) . . ?
N24 C8 N22 120.87(11) . . ?
N24 C8 N23 120.02(11) . . ?
N22 C8 N23 119.10(11) . . ?

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
C2 N2 N3 C1 0.24(11) . . . . ?
C2 N2 N3 C3 178.05(9) . . . . ?
C3 N6 N7 N8 -0.09(12) . . . . ?
N6 N7 N8 N9 -0.01(13) . . . . ?
N7 N8 N9 C3 0.10(12) . . . . ?
C5 N11 N12 C4 -0.28(11) . . . . ?
C5 N11 N12 C6 -179.06(10) . . . . ?
C6 N15 N16 N17 0.12(13) . . . . ?
N15 N16 N17 N18 -0.09(13) . . . . ?
N16 N17 N18 C6 0.03(12) . . . . ?
C2 N1 C1 N4 179.36(11) . . . . ?
C2 N1 C1 N3 -0.27(11) . . . . ?
N2 N3 C1 N4 -179.62(9) . . . . ?
C3 N3 C1 N4 2.78(17) . . . . ?
N2 N3 C1 N1 0.02(11) . . . . ?
C3 N3 C1 N1 -177.57(9) . . . . ?
N3 N2 C2 N1 -0.46(12) . . . . ?
N3 N2 C2 N5 179.98(9) . . . . ?
C1 N1 C2 N2 0.49(12) . . . . ?
C1 N1 C2 N5 -179.96(9) . . . . ?
O2 N5 C2 N2 -4.42(14) . . . . ?
O1 N5 C2 N2 175.82(9) . . . . ?
O2 N5 C2 N1 176.03(9) . . . . ?
O1 N5 C2 N1 -3.73(14) . . . . ?
N7 N6 C3 N9 0.17(12) . . . . ?
N7 N6 C3 N3 -178.66(9) . . . . ?
N8 N9 C3 N6 -0.17(12) . . . . ?
N8 N9 C3 N3 178.66(9) . . . . ?
C1 N3 C3 N6 176.82(10) . . . . ?
N2 N3 C3 N6 -0.55(15) . . . . ?
C1 N3 C3 N9 -1.91(16) . . . . ?
N2 N3 C3 N9 -179.28(9) . . . . ?
C5 N10 C4 N13 178.30(11) . . . . ?
C5 N10 C4 N12 0.16(11) . . . . ?
N11 N12 C4 N13 -178.13(10) . . . . ?
C6 N12 C4 N13 0.53(18) . . . . ?
N11 N12 C4 N10 0.07(12) . . . . ?
C6 N12 C4 N10 178.74(10) . . . . ?
N12 N11 C5 N10 0.43(12) . . . . ?
N12 N11 C5 N14 -178.87(9) . . . . ?
C4 N10 C5 N11 -0.39(13) . . . . ?
C4 N10 C5 N14 178.88(10) . . . . ?
O3 N14 C5 N11 177.42(10) . . . . ?
O4 N14 C5 N11 -2.26(15) . . . . ?
O3 N14 C5 N10 -1.85(15) . . . . ?
O4 N14 C5 N10 178.47(10) . . . . ?
N16 N15 C6 N18 -0.10(13) . . . . ?
N16 N15 C6 N12 179.79(10) . . . . ?
N17 N18 C6 N15 0.05(13) . . . . ?
N17 N18 C6 N12 -179.84(10) . . . . ?
C4 N12 C6 N15 173.54(10) . . . . ?
N11 N12 C6 N15 -7.92(16) . . . . ?
C4 N12 C6 N18 -6.58(17) . . . . ?
N11 N12 C6 N18 171.96(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        31.51
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 1017631'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_bo3182

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5.46 H9.92 N14 O2.50'
_chemical_formula_weight         311.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   17.869(6)
_cell_length_b                   7.864(2)
_cell_length_c                   18.347(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.227(4)
_cell_angle_gamma                90.00
_cell_volume                     2499.2(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    4909
_cell_measurement_theta_min      2.349
_cell_measurement_theta_max      31.487

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1286
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9327
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            14198
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         31.00
_reflns_number_total             3929
_reflns_number_gt                3462
_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)+(0.0786P)²+1.2600P] 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         3929
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O 0.22954(7) 0.63158(15) 0.19210(7) 0.0398(3) Uani 1 1 d . . .
O2 O 0.17347(7) 0.38966(14) 0.20114(6) 0.0375(3) Uani 1 1 d . . .
N1 N 0.21447(7) 0.58799(14) 0.04318(7) 0.0262(2) Uani 1 1 d . . .
N2 N 0.16422(6) 0.32447(14) 0.05519(6) 0.0224(2) Uani 1 1 d . . .
N3 N 0.16884(6) 0.35372(14) -0.01807(6) 0.0219(2) Uani 1 1 d . . .
N4 N 0.21080(8) 0.57633(18) -0.08761(8) 0.0343(3) Uani 1 1 d . . .
N5 N 0.19897(7) 0.49826(15) 0.16583(7) 0.0266(2) Uani 1 1 d . . .
N6 N 0.11564(7) 0.08250(14) -0.06012(6) 0.0239(2) Uani 1 1 d . . .
N7 N 0.09823(7) 0.00471(15) -0.12779(7) 0.0277(3) Uani 1 1 d . . .
N8 N 0.11501(7) 0.10607(16) -0.17813(7) 0.0289(3) Uani 1 1 d . . .
N9 N 0.14445(7) 0.25496(15) -0.14541(7) 0.0277(3) Uani 1 1 d . . .
N10 N 0.07854(7) 0.89716(14) 0.05059(6) 0.0230(2) Uani 1 1 d . . .
N11 N 0.05586(7) 0.75180(14) 0.14196(7) 0.0265(2) Uani 1 1 d . . .
N12 N 0.02932(7) 0.65140(14) 0.07729(7) 0.0258(2) Uani 1 1 d . . .
N13 N 0.11571(9) 1.02216(17) 0.17242(8) 0.0354(3) Uani 1 1 d . . .
N14 N 0.02891(8) 0.70646(17) -0.05006(7) 0.0321(3) Uani 1 1 d . . .
C1 C 0.19930(7) 0.51205(16) -0.02413(8) 0.0245(3) Uani 1 1 d . . .
C2 C 0.19212(7) 0.46812(16) 0.08602(8) 0.0222(2) Uani 1 1 d . . .
C3 C 0.14309(7) 0.23239(16) -0.07401(7) 0.0204(2) Uani 1 1 d . . .
C4 C 0.08530(8) 0.89831(17) 0.12551(7) 0.0241(3) Uani 1 1 d . . .
C5 C 0.04453(7) 0.74565(16) 0.02352(8) 0.0232(3) Uani 1 1 d . . .
O3 O 0.01724(11) 0.5649(3) 0.25909(16) 0.0242(6) Uani 0.4612(18) 1 d P A 1
H3 H 0.0596 0.5778 0.2909 0.029 Uiso 0.4612(18) 1 calc PR A 1
C6 C 0.0000 0.3905(4) 0.2500 0.0514(8) Uani 0.922(4) 2 d SP A 1
H6A H 0.0407 0.3326 0.2322 0.062 Uiso 0.4612(18) 1 calc PR A 1
H6B H -0.0495 0.3755 0.2131 0.062 Uiso 0.4612(18) 1 calc PR A 1
H6C H -0.0032 0.3418 0.2983 0.062 Uiso 0.4612(18) 1 calc PR A 1
O3' O 0.0000 0.2313(17) 0.2500 0.019(4) Uani 0.078(4) 2 d SP B 2
H4A H 0.2006(12) 0.514(3) -0.1273(12) 0.042(5) Uiso 1 1 d . . .
H4B H 0.2310(12) 0.679(3) -0.0850(12) 0.049(6) Uiso 1 1 d . . .
H10 H 0.0980(11) 0.971(3) 0.0222(11) 0.041(5) Uiso 1 1 d . . .
H11 H 0.0464(12) 0.716(3) 0.1901(13) 0.051(6) Uiso 1 1 d . . .
H13A H 0.1191(14) 1.003(3) 0.2241(13) 0.061(7) Uiso 1 1 d . . .
H13B H 0.1350(11) 1.110(3) 0.1521(12) 0.043(5) Uiso 1 1 d . . .
H14A H 0.0473(12) 0.770(3) -0.0836(12) 0.048(6) Uiso 1 1 d . . .
H14B H 0.0113(10) 0.605(3) -0.0654(11) 0.034(5) 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
O1 N5 1.2250(16) . ?
O2 N5 1.2255(16) . ?
N1 C1 1.3381(19) . ?
N1 C2 1.3492(17) . ?
N2 C2 1.3063(17) . ?
N2 N3 1.3860(16) . ?
N3 C1 1.3744(16) . ?
N3 C3 1.3940(17) . ?
N4 C1 1.3310(19) . ?
N4 H4A 0.86(2) . ?
N4 H4B 0.88(2) . ?
N5 C2 1.4584(18) . ?
N6 C3 1.3254(16) . ?
N6 N7 1.3500(16) . ?
N7 N8 1.3095(16) . ?
N8 N9 1.3612(17) . ?
N9 C3 1.3281(17) . ?
N10 C4 1.3500(17) . ?
N10 C5 1.3739(17) . ?
N10 H10 0.90(2) . ?
N11 C4 1.3318(17) . ?
N11 N12 1.4069(17) . ?
N11 H11 0.98(2) . ?
N12 C5 1.3147(17) . ?
N13 C4 1.3247(19) . ?
N13 H13A 0.95(2) . ?
N13 H13B 0.89(2) . ?
N14 C5 1.3454(19) . ?
N14 H14A 0.91(2) . ?
N14 H14B 0.88(2) . ?
O3 C6 1.407(3) . ?
O3 H3 0.8400 . ?
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 C2 101.78(11) . . ?
C2 N2 N3 99.73(10) . . ?
C1 N3 N2 110.37(11) . . ?
C1 N3 C3 128.77(12) . . ?
N2 N3 C3 120.85(10) . . ?
C1 N4 H4A 118.6(14) . . ?
C1 N4 H4B 116.7(15) . . ?
H4A N4 H4B 125(2) . . ?
O1 N5 O2 125.19(13) . . ?
O1 N5 C2 116.96(12) . . ?
O2 N5 C2 117.85(11) . . ?
C3 N6 N7 103.81(11) . . ?
N8 N7 N6 109.39(11) . . ?
N7 N8 N9 110.07(11) . . ?
C3 N9 N8 102.79(11) . . ?
C4 N10 C5 107.15(11) . . ?
C4 N10 H10 129.2(13) . . ?
C5 N10 H10 123.1(13) . . ?
C4 N11 N12 111.37(11) . . ?
C4 N11 H11 128.3(13) . . ?
N12 N11 H11 119.9(13) . . ?
C5 N12 N11 103.15(11) . . ?
C4 N13 H13A 116.6(15) . . ?
C4 N13 H13B 115.8(13) . . ?
H13A N13 H13B 127(2) . . ?
C5 N14 H14A 122.1(14) . . ?
C5 N14 H14B 120.0(13) . . ?
H14A N14 H14B 116.1(18) . . ?
N4 C1 N1 126.74(13) . . ?
N4 C1 N3 124.35(13) . . ?
N1 C1 N3 108.91(12) . . ?
N2 C2 N1 119.21(12) . . ?
N2 C2 N5 120.28(11) . . ?
N1 C2 N5 120.51(12) . . ?
N6 C3 N9 113.95(12) . . ?
N6 C3 N3 122.55(12) . . ?
N9 C3 N3 123.50(11) . . ?
N13 C4 N11 127.64(13) . . ?
N13 C4 N10 125.89(12) . . ?
N11 C4 N10 106.47(12) . . ?
N12 C5 N14 126.42(13) . . ?
N12 C5 N10 111.86(12) . . ?
N14 C5 N10 121.71(12) . . ?

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
C2 N2 N3 C1 0.17(13) . . . . ?
C2 N2 N3 C3 -178.64(11) . . . . ?
C3 N6 N7 N8 -0.05(14) . . . . ?
N6 N7 N8 N9 0.18(15) . . . . ?
N7 N8 N9 C3 -0.23(15) . . . . ?
C4 N11 N12 C5 -0.08(14) . . . . ?
C2 N1 C1 N4 179.95(14) . . . . ?
C2 N1 C1 N3 0.29(14) . . . . ?
N2 N3 C1 N4 -179.98(13) . . . . ?
C3 N3 C1 N4 -1.3(2) . . . . ?
N2 N3 C1 N1 -0.31(15) . . . . ?
C3 N3 C1 N1 178.38(12) . . . . ?
N3 N2 C2 N1 0.02(15) . . . . ?
N3 N2 C2 N5 180.00(11) . . . . ?
C1 N1 C2 N2 -0.20(16) . . . . ?
C1 N1 C2 N5 179.81(11) . . . . ?
O1 N5 C2 N2 176.05(12) . . . . ?
O2 N5 C2 N2 -4.39(18) . . . . ?
O1 N5 C2 N1 -3.97(18) . . . . ?
O2 N5 C2 N1 175.59(12) . . . . ?
N7 N6 C3 N9 -0.11(15) . . . . ?
N7 N6 C3 N3 -179.46(11) . . . . ?
N8 N9 C3 N6 0.21(15) . . . . ?
N8 N9 C3 N3 179.55(12) . . . . ?
C1 N3 C3 N6 179.12(12) . . . . ?
N2 N3 C3 N6 -2.30(18) . . . . ?
C1 N3 C3 N9 -0.2(2) . . . . ?
N2 N3 C3 N9 178.41(11) . . . . ?
N12 N11 C4 N13 -179.64(14) . . . . ?
N12 N11 C4 N10 0.17(15) . . . . ?
C5 N10 C4 N13 179.62(14) . . . . ?
C5 N10 C4 N11 -0.19(14) . . . . ?
N11 N12 C5 N14 -179.02(13) . . . . ?
N11 N12 C5 N10 -0.04(14) . . . . ?
C4 N10 C5 N12 0.15(15) . . . . ?
C4 N10 C5 N14 179.18(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 1017632'
