# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1585914'
_audit_update_record             
;
2017-11-19 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        HNIW-N2O
_chemical_name_common            
'hexanitrohexaazaisowurtzitane and nitrous oxide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N26 O25'
_chemical_formula_weight         920.48

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.5768(17)
_cell_length_b                   13.256(2)
_cell_length_c                   23.625(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2999.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3687
_cell_measurement_theta_max      22.78
_cell_measurement_theta_min      2.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.038
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0604 before and 0.0417 after correction. 
The Ratio of minimum to maximum transmission is 0.8849. 
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24454
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.724
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3722
_reflns_number_gt                2283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0943P)²+3.3601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0025(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     284
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4171(3) 0.2073(2) 0.22432(11) 0.0523(7) Uani 1 1 d . . . . .
O2 O 0.3067(2) 0.07298(17) 0.25276(11) 0.0414(6) Uani 1 1 d . . . . .
N1 N 0.4016(3) 0.13382(19) 0.25502(11) 0.0334(6) Uani 1 1 d . . . . .
N2 N 0.5030(2) 0.11794(18) 0.29517(10) 0.0283(5) Uani 1 1 d . . . . .
C1 C 0.4743(3) 0.0460(2) 0.34056(12) 0.0298(6) Uani 1 1 d . . . . .
H1 H 0.453543 -0.021370 0.325698 0.036 Uiso 1 1 calc R U . . .
N3 N 0.6080(3) 0.04860(18) 0.36965(10) 0.0298(5) Uani 1 1 d . . . . .
N4 N 0.7045(3) -0.0300(2) 0.35758(11) 0.0358(6) Uani 1 1 d . . . . .
O3 O 0.6576(3) -0.10773(17) 0.33904(13) 0.0518(7) Uani 1 1 d . . . . .
O4 O 0.8244(3) -0.01251(19) 0.37024(12) 0.0503(7) Uani 1 1 d . . . . .
C2 C 0.6626(3) 0.1524(2) 0.36783(12) 0.0274(6) Uani 1 1 d . . . . .
H2 H 0.763794 0.152694 0.361571 0.033 Uiso 1 1 calc R U . . .
N5 N 0.6268(3) 0.20649(18) 0.41907(10) 0.0291(5) Uani 1 1 d . . . . .
N6 N 0.7239(3) 0.2059(2) 0.46307(11) 0.0353(6) Uani 1 1 d . . . . .
O5 O 0.8397(3) 0.1756(2) 0.45235(11) 0.0476(6) Uani 1 1 d . . . . .
O6 O 0.6850(3) 0.2408(2) 0.50805(10) 0.0520(7) Uani 1 1 d . . . . .
C3 C 0.4801(3) 0.2105(2) 0.43352(12) 0.0310(6) Uani 1 1 d . . . . .
H3 H 0.464819 0.248219 0.468648 0.037 Uiso 1 1 calc R U . . .
N7 N 0.4185(3) 0.1100(2) 0.43663(11) 0.0381(6) Uani 1 1 d . . . . .
N8 N 0.3688(3) 0.0704(2) 0.48589(13) 0.0464(7) Uani 1 1 d . . . . .
O7 O 0.2937(4) -0.0027(2) 0.48199(14) 0.0755(10) Uani 1 1 d . . . . .
O8 O 0.4088(4) 0.1098(2) 0.52973(11) 0.0648(9) Uani 1 1 d . . . . .
C4 C 0.3557(3) 0.0845(2) 0.38217(13) 0.0327(7) Uani 1 1 d . . . . .
H4 H 0.280632 0.034821 0.386278 0.039 Uiso 1 1 calc R U . . .
N9 N 0.3030(3) 0.18160(19) 0.36195(11) 0.0327(6) Uani 1 1 d . . . . .
N10 N 0.1576(3) 0.2012(3) 0.37280(13) 0.0448(7) Uani 1 1 d . . . . .
O9 O 0.1231(3) 0.2888(2) 0.37049(13) 0.0597(8) Uani 1 1 d . . . . .
O10 O 0.0837(3) 0.1284(2) 0.37946(16) 0.0696(9) Uani 1 1 d . . . . .
C5 C 0.4004(3) 0.2604(2) 0.38233(13) 0.0316(6) Uani 1 1 d . . . . .
H5 H 0.349224 0.320484 0.394707 0.038 Uiso 1 1 calc R U . . .
N11 N 0.4997(3) 0.28557(18) 0.33931(11) 0.0312(6) Uani 1 1 d . . . . .
N12 N 0.4729(3) 0.3699(2) 0.30459(14) 0.0452(7) Uani 1 1 d . . . . .
O11 O 0.5549(3) 0.3838(2) 0.26625(12) 0.0586(8) Uani 1 1 d . . . . .
O12 O 0.3753(3) 0.4225(2) 0.31805(15) 0.0709(9) Uani 1 1 d . . . . .
C6 C 0.5838(3) 0.2043(2) 0.31723(12) 0.0279(6) Uani 1 1 d . . . . .
H6 H 0.649901 0.229157 0.288809 0.033 Uiso 1 1 calc R U . . .
O13 O 0.988(2) -0.0636(14) 0.4629(8) 0.167(3) Uani 0.5 1 d D . P . .
N13 N 1.000000 0.000000 0.500000 0.167(3) Uani 1 2 d DS . P . .
N14 N 1.002(3) 0.0591(16) 0.5333(9) 0.167(3) Uani 0.5 1 d D . P . .


_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 N1 1.223(3) . ?
O2 N1 1.216(3) . ?
N1 N2 1.374(3) . ?
N2 C1 1.461(4) . ?
N2 C6 1.477(4) . ?
C1 N3 1.453(4) . ?
C1 C4 1.587(4) . ?
C1 H1 0.9800 . ?
N3 N4 1.422(3) . ?
N3 C2 1.473(4) . ?
N4 O3 1.206(3) . ?
N4 O4 1.209(4) . ?
C2 N5 1.448(4) . ?
C2 C6 1.572(4) . ?
C2 H2 0.9800 . ?
N5 N6 1.395(3) . ?
N5 C3 1.447(4) . ?
N6 O5 1.206(4) . ?
N6 O6 1.217(4) . ?
C3 N7 1.459(4) . ?
C3 C5 1.575(4) . ?
C3 H3 0.9800 . ?
N7 N8 1.362(4) . ?
N7 C4 1.460(4) . ?
N8 O7 1.210(4) . ?
N8 O8 1.222(4) . ?
C4 N9 1.463(4) . ?
C4 H4 0.9800 . ?
N9 N10 1.439(4) . ?
N9 C5 1.481(4) . ?
N10 O10 1.207(4) . ?
N10 O9 1.207(4) . ?
C5 N11 1.431(4) . ?
C5 H5 0.9800 . ?
N11 N12 1.410(4) . ?
N11 C6 1.442(4) . ?
N12 O12 1.209(4) . ?
N12 O11 1.213(4) . ?
C6 H6 0.9800 . ?
O13 N13 1.2208(10) . ?
N13 N14 1.1107(10) 5_756 ?
N13 N14 1.1107(10) . ?

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
O2 N1 O1 126.3(3) . . ?
O2 N1 N2 117.2(2) . . ?
O1 N1 N2 116.5(2) . . ?
N1 N2 C1 118.3(2) . . ?
N1 N2 C6 119.7(2) . . ?
C1 N2 C6 110.2(2) . . ?
N3 C1 N2 99.5(2) . . ?
N3 C1 C4 109.3(2) . . ?
N2 C1 C4 112.3(2) . . ?
N3 C1 H1 111.7 . . ?
N2 C1 H1 111.7 . . ?
C4 C1 H1 111.7 . . ?
N4 N3 C1 117.4(2) . . ?
N4 N3 C2 116.6(2) . . ?
C1 N3 C2 108.7(2) . . ?
O3 N4 O4 127.4(3) . . ?
O3 N4 N3 117.2(3) . . ?
O4 N4 N3 115.3(2) . . ?
N5 C2 N3 110.7(2) . . ?
N5 C2 C6 107.8(2) . . ?
N3 C2 C6 105.1(2) . . ?
N5 C2 H2 111.0 . . ?
N3 C2 H2 111.0 . . ?
C6 C2 H2 111.0 . . ?
N6 N5 C3 118.1(2) . . ?
N6 N5 C2 117.5(2) . . ?
C3 N5 C2 116.5(2) . . ?
O5 N6 O6 126.2(3) . . ?
O5 N6 N5 117.3(3) . . ?
O6 N6 N5 116.4(3) . . ?
N5 C3 N7 111.8(2) . . ?
N5 C3 C5 107.7(2) . . ?
N7 C3 C5 103.1(2) . . ?
N5 C3 H3 111.3 . . ?
N7 C3 H3 111.3 . . ?
C5 C3 H3 111.3 . . ?
N8 N7 C4 121.3(3) . . ?
N8 N7 C3 122.4(3) . . ?
C4 N7 C3 109.5(2) . . ?
O7 N8 O8 126.4(3) . . ?
O7 N8 N7 116.8(3) . . ?
O8 N8 N7 116.8(3) . . ?
N7 C4 N9 103.1(2) . . ?
N7 C4 C1 109.0(2) . . ?
N9 C4 C1 109.2(2) . . ?
N7 C4 H4 111.7 . . ?
N9 C4 H4 111.7 . . ?
C1 C4 H4 111.7 . . ?
N10 N9 C4 115.8(3) . . ?
N10 N9 C5 115.1(2) . . ?
C4 N9 C5 107.3(2) . . ?
O10 N10 O9 127.9(3) . . ?
O10 N10 N9 116.5(3) . . ?
O9 N10 N9 115.5(3) . . ?
N11 C5 N9 110.6(2) . . ?
N11 C5 C3 108.7(2) . . ?
N9 C5 C3 105.0(2) . . ?
N11 C5 H5 110.8 . . ?
N9 C5 H5 110.8 . . ?
C3 C5 H5 110.8 . . ?
N12 N11 C5 118.5(3) . . ?
N12 N11 C6 118.9(3) . . ?
C5 N11 C6 117.0(2) . . ?
O12 N12 O11 127.5(3) . . ?
O12 N12 N11 116.4(3) . . ?
O11 N12 N11 115.9(3) . . ?
N11 C6 N2 114.5(2) . . ?
N11 C6 C2 108.6(2) . . ?
N2 C6 C2 100.4(2) . . ?
N11 C6 H6 110.9 . . ?
N2 C6 H6 110.9 . . ?
C2 C6 H6 110.9 . . ?
O13 N13 O13 180.0 5_756 . ?
O13 N13 N14 176(2) 5_756 5_756 ?
O13 N13 N14 176(2) . . ?
N14 N13 N14 180.0(16) 5_756 . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_cd17182
_database_code_depnum_ccdc_archive 'CCDC 1585915'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        HNIW-CO2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6.50 H6 N12 O13'
_chemical_formula_weight         460.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.6731(10)
_cell_length_b                   13.2031(12)
_cell_length_c                   23.553(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3008.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5137
_cell_measurement_theta_min      5.450
_cell_measurement_theta_max      53.774

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16088
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2793
_reflns_number_gt                2466
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+1.6858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2793
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.00041(14) 0.88091(11) 0.29480(6) 0.0222(3) Uani 1 1 d . . . . .
N2 N 0.89892(15) 0.86486(11) 0.25493(6) 0.0276(3) Uani 1 1 d . . . . .
N3 N 0.80468(14) 0.81735(11) 0.36280(6) 0.0265(3) Uani 1 1 d . . . . .
N4 N 0.66072(16) 0.79773(14) 0.37422(7) 0.0377(4) Uani 1 1 d . . . . .
N5 N 0.99802(15) 0.71304(10) 0.33916(6) 0.0251(3) Uani 1 1 d . . . . .
N6 N 0.97212(19) 0.62798(12) 0.30482(7) 0.0374(4) Uani 1 1 d . . . . .
N7 N 1.12618(14) 0.79251(10) 0.41847(6) 0.0223(3) Uani 1 1 d . . . . .
N8 N 1.22379(15) 0.79323(11) 0.46191(6) 0.0263(3) Uani 1 1 d . . . . .
N9 N 0.92053(16) 0.88930(12) 0.43697(6) 0.0298(4) Uani 1 1 d . . . . .
N10 N 0.87198(17) 0.92894(12) 0.48679(7) 0.0332(4) Uani 1 1 d . . . . .
N11 N 1.10639(15) 0.95051(10) 0.36892(6) 0.0243(3) Uani 1 1 d . . . . .
N12 N 1.20201(17) 1.02890(12) 0.35608(6) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.80441(13) 0.92549(10) 0.25339(6) 0.0352(3) Uani 1 1 d . . . . .
O2 O 0.91419(16) 0.79198(11) 0.22378(6) 0.0467(4) Uani 1 1 d . . . . .
O3 O 0.58876(15) 0.87066(14) 0.38245(9) 0.0625(5) Uani 1 1 d . . . . .
O4 O 0.62632(15) 0.71059(13) 0.37095(7) 0.0522(4) Uani 1 1 d . . . . .
O5 O 0.8762(2) 0.57478(12) 0.31902(8) 0.0633(5) Uani 1 1 d . . . . .
O6 O 1.05121(18) 0.61383(11) 0.26621(6) 0.0501(4) Uani 1 1 d . . . . .
O7 O 1.18686(14) 0.75894(12) 0.50738(5) 0.0412(4) Uani 1 1 d . . . . .
O8 O 1.33804(13) 0.82308(11) 0.45008(6) 0.0390(3) Uani 1 1 d . . . . .
O9 O 0.91194(18) 0.88944(12) 0.53033(6) 0.0491(4) Uani 1 1 d . . . . .
O10 O 0.79754(18) 1.00286(12) 0.48293(7) 0.0535(4) Uani 1 1 d . . . . .
O11 O 1.32099(14) 1.01118(11) 0.36785(6) 0.0447(4) Uani 1 1 d . . . . .
O12 O 1.15497(16) 1.10725(10) 0.33796(7) 0.0465(4) Uani 1 1 d . . . . .
O13 O 0.9928(2) 0.06000(14) 0.03472(9) 0.0689(5) Uani 1 1 d . . . . .
C1 C 1.08105(17) 0.79421(12) 0.31662(7) 0.0230(4) Uani 1 1 d . . . . .
H1 H 1.1458 0.7691 0.2879 0.028 Uiso 1 1 calc R U . . .
C2 C 1.15991(17) 0.84645(12) 0.36692(7) 0.0217(3) Uani 1 1 d . . . . .
H2A H 1.2599 0.8462 0.3602 0.026 Uiso 1 1 calc R U . . .
C3 C 0.90113(17) 0.73823(13) 0.38281(7) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.8506 0.6780 0.3955 0.030 Uiso 1 1 calc R U . . .
C4 C 0.98156(17) 0.78843(13) 0.43372(7) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.9675 0.7506 0.4691 0.028 Uiso 1 1 calc R U . . .
C5 C 0.97361(17) 0.95323(12) 0.34051(7) 0.0229(4) Uani 1 1 d . . . . .
H5 H 0.9527 1.0209 0.3257 0.028 Uiso 1 1 calc R U . . .
C6 C 0.85716(18) 0.91461(13) 0.38279(7) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.7829 0.9645 0.3872 0.031 Uiso 1 1 calc R U . . .
C7 C 1.0000 0.0000 0.0000 0.0485(8) Uani 1 2 d S . P . .


_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 1.3750(19) . ?
N1 C5 1.462(2) . ?
N1 C1 1.478(2) . ?
N2 O1 1.2157(19) . ?
N2 O2 1.219(2) . ?
N3 N4 1.442(2) . ?
N3 C6 1.459(2) . ?
N3 C3 1.478(2) . ?
N4 O4 1.200(2) . ?
N4 O3 1.204(2) . ?
N5 N6 1.406(2) . ?
N5 C3 1.430(2) . ?
N5 C1 1.441(2) . ?
N6 O6 1.203(2) . ?
N6 O5 1.211(2) . ?
N7 N8 1.3922(19) . ?
N7 C2 1.445(2) . ?
N7 C4 1.445(2) . ?
N8 O8 1.206(2) . ?
N8 O7 1.216(2) . ?
N9 N10 1.368(2) . ?
N9 C6 1.455(2) . ?
N9 C4 1.459(2) . ?
N10 O9 1.214(2) . ?
N10 O10 1.216(2) . ?
N11 N12 1.421(2) . ?
N11 C5 1.449(2) . ?
N11 C2 1.469(2) . ?
N12 O11 1.207(2) . ?
N12 O12 1.208(2) . ?
O13 C7 1.141(2) . ?
C1 C2 1.569(2) . ?
C1 H1 0.9800 . ?
C2 H2A 0.9800 . ?
C3 C4 1.576(2) . ?
C3 H3 0.9800 . ?
C4 H4 0.9800 . ?
C5 C6 1.588(2) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 O13 1.141(2) 5_755 ?

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 C5 118.48(13) . . ?
N2 N1 C1 119.67(13) . . ?
C5 N1 C1 110.09(12) . . ?
O1 N2 O2 126.36(15) . . ?
O1 N2 N1 117.12(14) . . ?
O2 N2 N1 116.50(14) . . ?
N4 N3 C6 115.73(14) . . ?
N4 N3 C3 115.04(14) . . ?
C6 N3 C3 107.43(13) . . ?
O4 N4 O3 128.08(17) . . ?
O4 N4 N3 115.35(17) . . ?
O3 N4 N3 116.41(17) . . ?
N6 N5 C3 118.83(15) . . ?
N6 N5 C1 118.78(14) . . ?
C3 N5 C1 117.20(13) . . ?
O6 N6 O5 127.31(17) . . ?
O6 N6 N5 116.45(17) . . ?
O5 N6 N5 116.16(18) . . ?
N8 N7 C2 117.46(13) . . ?
N8 N7 C4 118.29(13) . . ?
C2 N7 C4 116.47(13) . . ?
O8 N8 O7 126.45(15) . . ?
O8 N8 N7 116.99(14) . . ?
O7 N8 N7 116.45(14) . . ?
N10 N9 C6 121.33(14) . . ?
N10 N9 C4 122.22(14) . . ?
C6 N9 C4 109.53(13) . . ?
O9 N10 O10 126.63(17) . . ?
O9 N10 N9 116.81(16) . . ?
O10 N10 N9 116.49(16) . . ?
N12 N11 C5 117.43(13) . . ?
N12 N11 C2 116.43(13) . . ?
C5 N11 C2 108.71(13) . . ?
O11 N12 O12 127.33(16) . . ?
O11 N12 N11 115.51(15) . . ?
O12 N12 N11 116.99(15) . . ?
N5 C1 N1 114.22(14) . . ?
N5 C1 C2 108.67(13) . . ?
N1 C1 C2 100.29(12) . . ?
N5 C1 H1 111.1 . . ?
N1 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
N7 C2 N11 110.75(13) . . ?
N7 C2 C1 107.94(13) . . ?
N11 C2 C1 105.32(13) . . ?
N7 C2 H2A 110.9 . . ?
N11 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
N5 C3 N3 110.41(13) . . ?
N5 C3 C4 108.74(13) . . ?
N3 C3 C4 104.90(13) . . ?
N5 C3 H3 110.9 . . ?
N3 C3 H3 110.9 . . ?
C4 C3 H3 110.9 . . ?
N7 C4 N9 111.76(14) . . ?
N7 C4 C3 107.73(13) . . ?
N9 C4 C3 102.95(13) . . ?
N7 C4 H4 111.4 . . ?
N9 C4 H4 111.4 . . ?
C3 C4 H4 111.4 . . ?
N11 C5 N1 99.59(13) . . ?
N11 C5 C6 109.35(13) . . ?
N1 C5 C6 112.20(13) . . ?
N11 C5 H5 111.7 . . ?
N1 C5 H5 111.7 . . ?
C6 C5 H5 111.7 . . ?
N9 C6 N3 103.15(13) . . ?
N9 C6 C5 108.97(14) . . ?
N3 C6 C5 109.10(13) . . ?
N9 C6 H6 111.7 . . ?
N3 C6 H6 111.7 . . ?
C5 C6 H6 111.7 . . ?
O13 C7 O13 180.00(15) . 5_755 ?

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
C5 N1 N2 O1 14.1(2) . . . . ?
C1 N1 N2 O1 153.47(15) . . . . ?
C5 N1 N2 O2 -167.28(15) . . . . ?
C1 N1 N2 O2 -27.9(2) . . . . ?
C6 N3 N4 O4 -162.20(16) . . . . ?
C3 N3 N4 O4 -35.9(2) . . . . ?
C6 N3 N4 O3 22.0(2) . . . . ?
C3 N3 N4 O3 148.35(17) . . . . ?
C3 N5 N6 O6 175.00(15) . . . . ?
C1 N5 N6 O6 21.1(2) . . . . ?
C3 N5 N6 O5 -8.2(2) . . . . ?
C1 N5 N6 O5 -162.03(17) . . . . ?
C2 N7 N8 O8 -12.7(2) . . . . ?
C4 N7 N8 O8 -160.92(15) . . . . ?
C2 N7 N8 O7 170.80(15) . . . . ?
C4 N7 N8 O7 22.6(2) . . . . ?
C6 N9 N10 O9 165.98(17) . . . . ?
C4 N9 N10 O9 18.2(2) . . . . ?
C6 N9 N10 O10 -16.9(2) . . . . ?
C4 N9 N10 O10 -164.73(17) . . . . ?
C5 N11 N12 O11 -161.16(15) . . . . ?
C2 N11 N12 O11 -29.7(2) . . . . ?
C5 N11 N12 O12 23.1(2) . . . . ?
C2 N11 N12 O12 154.52(16) . . . . ?
N6 N5 C1 N1 99.15(17) . . . . ?
C3 N5 C1 N1 -55.15(18) . . . . ?
N6 N5 C1 C2 -149.83(14) . . . . ?
C3 N5 C1 C2 55.88(18) . . . . ?
N2 N1 C1 N5 -54.13(19) . . . . ?
C5 N1 C1 N5 88.31(16) . . . . ?
N2 N1 C1 C2 -170.14(13) . . . . ?
C5 N1 C1 C2 -27.69(16) . . . . ?
N8 N7 C2 N11 -93.15(16) . . . . ?
C4 N7 C2 N11 55.66(18) . . . . ?
N8 N7 C2 C1 152.04(13) . . . . ?
C4 N7 C2 C1 -59.15(18) . . . . ?
N12 N11 C2 N7 129.03(14) . . . . ?
C5 N11 C2 N7 -95.61(15) . . . . ?
N12 N11 C2 C1 -114.53(14) . . . . ?
C5 N11 C2 C1 20.83(16) . . . . ?
N5 C1 C2 N7 2.19(17) . . . . ?
N1 C1 C2 N7 122.28(13) . . . . ?
N5 C1 C2 N11 -116.16(14) . . . . ?
N1 C1 C2 N11 3.93(15) . . . . ?
N6 N5 C3 N3 -97.03(17) . . . . ?
C1 N5 C3 N3 57.26(18) . . . . ?
N6 N5 C3 C4 148.40(14) . . . . ?
C1 N5 C3 C4 -57.32(18) . . . . ?
N4 N3 C3 N5 132.86(15) . . . . ?
C6 N3 C3 N5 -96.69(15) . . . . ?
N4 N3 C3 C4 -110.16(16) . . . . ?
C6 N3 C3 C4 20.29(16) . . . . ?
N8 N7 C4 N9 93.79(17) . . . . ?
C2 N7 C4 N9 -54.75(18) . . . . ?
N8 N7 C4 C3 -153.82(13) . . . . ?
C2 N7 C4 C3 57.64(18) . . . . ?
N10 N9 C4 N7 -115.12(17) . . . . ?
C6 N9 C4 N7 93.75(16) . . . . ?
N10 N9 C4 C3 129.53(16) . . . . ?
C6 N9 C4 C3 -21.60(17) . . . . ?
N5 C3 C4 N7 0.47(18) . . . . ?
N3 C3 C4 N7 -117.64(14) . . . . ?
N5 C3 C4 N9 118.69(14) . . . . ?
N3 C3 C4 N9 0.58(16) . . . . ?
N12 N11 C5 N1 98.32(15) . . . . ?
C2 N11 C5 N1 -36.53(15) . . . . ?
N12 N11 C5 C6 -143.93(14) . . . . ?
C2 N11 C5 C6 81.22(15) . . . . ?
N2 N1 C5 N11 -176.65(13) . . . . ?
C1 N1 C5 N11 40.40(15) . . . . ?
N2 N1 C5 C6 67.77(18) . . . . ?
C1 N1 C5 C6 -75.19(16) . . . . ?
N10 N9 C6 N3 -116.86(17) . . . . ?
C4 N9 C6 N3 34.57(17) . . . . ?
N10 N9 C6 C5 127.31(16) . . . . ?
C4 N9 C6 C5 -81.25(16) . . . . ?
N4 N3 C6 N9 96.76(16) . . . . ?
C3 N3 C6 N9 -33.31(16) . . . . ?
N4 N3 C6 C5 -147.51(14) . . . . ?
C3 N3 C6 C5 82.43(16) . . . . ?
N11 C5 C6 N9 0.40(18) . . . . ?
N1 C5 C6 N9 109.92(15) . . . . ?
N11 C5 C6 N3 -111.54(15) . . . . ?
N1 C5 C6 N3 -2.02(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O5 0.98 2.66 3.438(2) 136.8 8_765
C5 H5 O6 0.98 2.49 3.297(2) 139.7 3_755
C4 H4 O13 0.98 2.55 3.116(3) 116.9 3_755
C4 H4 O8 0.98 2.48 3.404(2) 157.3 4_466
C2 H2A O2 0.98 2.58 3.336(2) 134.1 6_656
C1 H1 O2 0.98 2.63 3.360(2) 131.7 6_656

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

