# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv364
_database_code_depnum_ccdc_archive 'CCDC 1474898'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Cl N9 O4'
_chemical_formula_sum            'C6 H6 Cl N9 O4'
_chemical_formula_weight         303.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   18.302(7)
_cell_length_b                   5.631(2)
_cell_length_c                   11.142(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.094(10)
_cell_angle_gamma                90
_cell_volume                     1139.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      27.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7893
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         27.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2537
_reflns_number_gt                2042
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1422P)²+4.1011P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2396
_refine_ls_wR_factor_gt          0.2088
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9560(3) 0.8785(10) 0.8387(5) 0.0281(12) Uani 1 1 d . . . . .
H1A H 0.976(4) 1.004(16) 0.872(7) 0.034 Uiso 1 1 d . U . . .
H1B H 0.935(5) 0.900(14) 0.773(8) 0.034 Uiso 1 1 d . U . . .
C2 C 0.9311(3) 0.7275(10) 0.9177(4) 0.0196(10) Uani 1 1 d . . . . .
N3 N 0.9427(3) 0.7410(10) 1.0367(4) 0.0255(10) Uani 1 1 d . . . . .
N4 N 0.9095(3) 0.5485(10) 1.0794(4) 0.0264(11) Uani 1 1 d . . . . .
N5 N 0.8771(3) 0.4211(9) 0.9922(4) 0.0256(11) Uani 1 1 d . . . . .
N6 N 0.8908(3) 0.5309(8) 0.8877(4) 0.0198(9) Uani 1 1 d . . . . .
C7 C 0.8663(3) 0.4257(11) 0.7701(5) 0.0243(12) Uani 1 1 d . . . . .
H7A H 0.8527 0.2577 0.7816 0.029 Uiso 1 1 calc R U . . .
H7B H 0.9075 0.4281 0.7203 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8005(3) 0.5553(10) 0.7026(4) 0.0202(11) Uani 1 1 d . . . . .
H8A H 0.8132 0.7248 0.6939 0.024 Uiso 1 1 calc R U . . .
H8B H 0.7895 0.4872 0.6204 0.024 Uiso 1 1 calc R U . . .
N9 N 0.7347(2) 0.5379(8) 0.7650(4) 0.0178(9) Uani 1 1 d . . . . .
N10 N 0.7225(3) 0.7166(8) 0.8383(4) 0.0197(9) Uani 1 1 d . . . . .
C11 C 0.6575(3) 0.6661(10) 0.8749(5) 0.0205(10) Uani 1 1 d . . . . .
N12 N 0.6291(3) 0.8312(9) 0.9564(4) 0.0248(11) Uani 1 1 d . . . . .
O13 O 0.6694(3) 0.9946(9) 0.9956(4) 0.0355(11) Uani 1 1 d . . . . .
O14 O 0.5660(3) 0.8006(9) 0.9790(5) 0.0396(12) Uani 1 1 d . . . . .
C15 C 0.6261(3) 0.4568(10) 0.8252(5) 0.0207(11) Uani 1 1 d . . . . .
Cl16 Cl 0.54546(8) 0.3304(3) 0.84765(15) 0.0313(4) Uani 1 1 d . . . . .
C17 C 0.6789(3) 0.3784(9) 0.7560(5) 0.0179(10) Uani 1 1 d . . . . .
N18 N 0.6787(3) 0.1646(8) 0.6839(4) 0.0227(10) Uani 1 1 d . . . . .
O19 O 0.6220(3) 0.0526(8) 0.6686(5) 0.0363(11) Uani 1 1 d . . . . .
O20 O 0.7369(2) 0.1082(8) 0.6477(4) 0.0280(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.344(7) . ?
N1 H1A 0.86(9) . ?
N1 H1B 0.80(9) . ?
C2 N3 1.319(6) . ?
C2 N6 1.349(7) . ?
N3 N4 1.357(7) . ?
N4 N5 1.292(7) . ?
N5 N6 1.368(6) . ?
N6 C7 1.457(7) . ?
C7 C8 1.525(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N9 1.466(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N9 N10 1.332(6) . ?
N9 C17 1.354(7) . ?
N10 C11 1.334(7) . ?
C11 C15 1.396(8) . ?
C11 N12 1.441(7) . ?
N12 O14 1.224(7) . ?
N12 O13 1.225(7) . ?
C15 C17 1.381(8) . ?
C15 Cl16 1.685(6) . ?
C17 N18 1.447(7) . ?
N18 O19 1.209(7) . ?
N18 O20 1.226(7) . ?

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
C2 N1 H1A 113(5) . . ?
C2 N1 H1B 122(6) . . ?
H1A N1 H1B 114(8) . . ?
N3 C2 N1 126.6(6) . . ?
N3 C2 N6 108.2(5) . . ?
N1 C2 N6 125.2(5) . . ?
C2 N3 N4 106.4(5) . . ?
N5 N4 N3 111.3(4) . . ?
N4 N5 N6 105.9(5) . . ?
C2 N6 N5 108.2(4) . . ?
C2 N6 C7 130.9(5) . . ?
N5 N6 C7 120.8(5) . . ?
N6 C7 C8 112.7(5) . . ?
N6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N9 C8 C7 112.3(4) . . ?
N9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N10 N9 C17 111.4(4) . . ?
N10 N9 C8 116.8(4) . . ?
C17 N9 C8 131.7(5) . . ?
N9 N10 C11 104.5(4) . . ?
N10 C11 C15 113.4(5) . . ?
N10 C11 N12 117.4(5) . . ?
C15 C11 N12 129.2(5) . . ?
O14 N12 O13 125.0(5) . . ?
O14 N12 C11 117.5(5) . . ?
O13 N12 C11 117.4(5) . . ?
C17 C15 C11 102.1(5) . . ?
C17 C15 Cl16 129.4(5) . . ?
C11 C15 Cl16 128.5(4) . . ?
N9 C17 C15 108.6(5) . . ?
N9 C17 N18 122.9(5) . . ?
C15 C17 N18 128.4(5) . . ?
O19 N18 O20 125.8(5) . . ?
O19 N18 C17 117.1(5) . . ?
O20 N18 C17 117.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N3 N4 -178.0(6) . . . . ?
N6 C2 N3 N4 0.6(6) . . . . ?
C2 N3 N4 N5 -1.3(7) . . . . ?
N3 N4 N5 N6 1.5(6) . . . . ?
N3 C2 N6 N5 0.3(6) . . . . ?
N1 C2 N6 N5 178.9(6) . . . . ?
N3 C2 N6 C7 -176.3(5) . . . . ?
N1 C2 N6 C7 2.3(10) . . . . ?
N4 N5 N6 C2 -1.1(6) . . . . ?
N4 N5 N6 C7 175.9(5) . . . . ?
C2 N6 C7 C8 -77.6(7) . . . . ?
N5 N6 C7 C8 106.2(6) . . . . ?
N6 C7 C8 N9 -64.7(6) . . . . ?
C7 C8 N9 N10 94.9(5) . . . . ?
C7 C8 N9 C17 -90.7(7) . . . . ?
C17 N9 N10 C11 -0.2(6) . . . . ?
C8 N9 N10 C11 175.3(4) . . . . ?
N9 N10 C11 C15 -0.8(6) . . . . ?
N9 N10 C11 N12 -179.7(4) . . . . ?
N10 C11 N12 O14 171.7(5) . . . . ?
C15 C11 N12 O14 -7.1(8) . . . . ?
N10 C11 N12 O13 -6.8(7) . . . . ?
C15 C11 N12 O13 174.5(5) . . . . ?
N10 C11 C15 C17 1.4(6) . . . . ?
N12 C11 C15 C17 -179.8(5) . . . . ?
N10 C11 C15 Cl16 179.9(4) . . . . ?
N12 C11 C15 Cl16 -1.3(9) . . . . ?
N10 N9 C17 C15 1.1(6) . . . . ?
C8 N9 C17 C15 -173.4(5) . . . . ?
N10 N9 C17 N18 -178.9(4) . . . . ?
C8 N9 C17 N18 6.6(9) . . . . ?
C11 C15 C17 N9 -1.5(6) . . . . ?
Cl16 C15 C17 N9 -179.9(4) . . . . ?
C11 C15 C17 N18 178.5(5) . . . . ?
Cl16 C15 C17 N18 0.0(9) . . . . ?
N9 C17 N18 O19 -169.8(5) . . . . ?
C15 C17 N18 O19 10.2(8) . . . . ?
N9 C17 N18 O20 13.0(7) . . . . ?
C15 C17 N18 O20 -167.0(5) . . . . ?

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
N1 H1A N3 0.86(9) 2.22(9) 3.053(8) 162(7) 3_777
N1 H1B N4 0.80(9) 2.17(9) 2.937(7) 163(8) 4_575
C7 H7A O20 0.99 2.58 3.141(7) 116.0 .
C8 H8A N4 0.99 2.63 3.394(7) 134.1 4_575
C8 H8A O20 0.99 2.59 3.354(7) 134.0 1_565
C8 H8B O13 0.99 2.45 3.128(7) 125.0 4_575

_refine_diff_density_max         0.664
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.095



# start Validation Reply Form
_vrf_PLAT015_shrv364             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
_vrf_PLAT430_shrv364             
;
PROBLEM: Short Inter D...A Contact  O13    ..  N18     ..       2.83 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv389
_database_code_depnum_ccdc_archive 'CCDC 1474899'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N10 O4'
_chemical_formula_sum            'C5 H6 N10 O4'
_chemical_formula_weight         270.20

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9667(5)
_cell_length_b                   12.8656(9)
_cell_length_c                   10.6222(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.131(2)
_cell_angle_gamma                90
_cell_volume                     1034.68(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3206
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_T_max  0.7461

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12230
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2995
_reflns_number_gt                2230
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0402P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2995
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.80465(12) 0.49237(8) 0.62702(10) 0.0260(2) Uani 1 1 d . . . . .
O2 O 0.69878(14) 0.36379(8) 0.49287(10) 0.0302(2) Uani 1 1 d . . . . .
N3 N 0.68867(14) 0.42619(8) 0.57899(10) 0.0206(2) Uani 1 1 d . . . . .
N4 N 0.54094(14) 0.41899(8) 0.61624(10) 0.0190(2) Uani 1 1 d . . . . .
C5 C 0.53355(16) 0.48412(9) 0.71205(12) 0.0172(2) Uani 1 1 d . . . . .
N6 N 0.64001(16) 0.55496(9) 0.79060(11) 0.0215(2) Uani 1 1 d . . . . .
N7 N 0.55948(15) 0.59827(9) 0.87398(12) 0.0264(3) Uani 1 1 d . . . . .
N8 N 0.40766(16) 0.55658(8) 0.85068(12) 0.0238(3) Uani 1 1 d . . . . .
N9 N 0.38782(14) 0.48535(8) 0.75232(11) 0.0179(2) Uani 1 1 d . . . . .
C10 C 0.21742(16) 0.43421(9) 0.69370(13) 0.0187(3) Uani 1 1 d . . . . .
H10A H 0.1906 0.4326 0.5962 0.022 Uiso 1 1 calc R U . . .
H10B H 0.1243 0.4757 0.7139 0.022 Uiso 1 1 calc R U . . .
C11 C 0.21208(17) 0.32366(9) 0.74357(13) 0.0198(3) Uani 1 1 d . . . . .
H11A H 0.2552 0.3233 0.8416 0.024 Uiso 1 1 calc R U . . .
H11B H 0.0886 0.2984 0.7148 0.024 Uiso 1 1 calc R U . . .
N12 N 0.32091(14) 0.25406(8) 0.69308(10) 0.0165(2) Uani 1 1 d . . . . .
N13 N 0.28247(14) 0.23933(8) 0.56091(10) 0.0170(2) Uani 1 1 d . . . . .
C14 C 0.41599(16) 0.18094(9) 0.55830(12) 0.0164(2) Uani 1 1 d . . . . .
N15 N 0.53536(14) 0.15606(8) 0.67433(10) 0.0195(2) Uani 1 1 d . . . . .
C16 C 0.47063(17) 0.20509(10) 0.75887(13) 0.0192(3) Uani 1 1 d . . . . .
H16 H 0.5229 0.2054 0.8524 0.023 Uiso 1 1 calc R U . . .
N17 N 0.43590(14) 0.14758(8) 0.43361(11) 0.0194(2) Uani 1 1 d . . . . .
O18 O 0.33264(14) 0.18296(9) 0.33166(9) 0.0323(3) Uani 1 1 d . . . . .
O19 O 0.55682(13) 0.08719(7) 0.43853(10) 0.0255(2) Uani 1 1 d . . . . .
H6 H 0.742(2) 0.5769(12) 0.7896(16) 0.031 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2432(14) . ?
O2 N3 1.2384(14) . ?
N3 N4 1.3565(15) . ?
N4 C5 1.3336(16) . ?
C5 N6 1.3438(16) . ?
C5 N9 1.3566(16) . ?
N6 N7 1.3639(16) . ?
N6 H6 0.861(18) . ?
N7 N8 1.2750(16) . ?
N8 N9 1.3615(15) . ?
N9 C10 1.4620(16) . ?
C10 C11 1.5230(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.4596(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C16 1.3376(16) . ?
N12 N13 1.3539(14) . ?
N13 C14 1.3096(16) . ?
C14 N15 1.3403(16) . ?
C14 N17 1.4473(16) . ?
N15 C16 1.3261(16) . ?
C16 H16 0.9500 . ?
N17 O18 1.2256(14) . ?
N17 O19 1.2260(14) . ?

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 N3 O1 122.43(11) . . ?
O2 N3 N4 115.66(11) . . ?
O1 N3 N4 121.90(11) . . ?
C5 N4 N3 115.34(10) . . ?
N4 C5 N6 136.95(12) . . ?
N4 C5 N9 119.56(11) . . ?
N6 C5 N9 103.47(11) . . ?
C5 N6 N7 110.29(11) . . ?
C5 N6 H6 129.0(11) . . ?
N7 N6 H6 120.6(11) . . ?
N8 N7 N6 108.16(11) . . ?
N7 N8 N9 107.98(11) . . ?
C5 N9 N8 110.09(10) . . ?
C5 N9 C10 129.26(11) . . ?
N8 N9 C10 120.03(10) . . ?
N9 C10 C11 113.26(10) . . ?
N9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N12 C11 C10 111.16(10) . . ?
N12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C16 N12 N13 110.67(10) . . ?
C16 N12 C11 129.20(11) . . ?
N13 N12 C11 119.89(10) . . ?
C14 N13 N12 100.32(10) . . ?
N13 C14 N15 117.78(11) . . ?
N13 C14 N17 120.71(11) . . ?
N15 C14 N17 121.48(11) . . ?
C16 N15 C14 101.24(10) . . ?
N15 C16 N12 109.98(11) . . ?
N15 C16 H16 125.0 . . ?
N12 C16 H16 125.0 . . ?
O18 N17 O19 125.14(11) . . ?
O18 N17 C14 117.63(11) . . ?
O19 N17 C14 117.22(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
O2 N3 N4 C5 177.91(11) . . . . ?
O1 N3 N4 C5 -3.18(17) . . . . ?
N3 N4 C5 N6 -4.3(2) . . . . ?
N3 N4 C5 N9 177.49(10) . . . . ?
N4 C5 N6 N7 -179.24(14) . . . . ?
N9 C5 N6 N7 -0.83(14) . . . . ?
C5 N6 N7 N8 0.38(15) . . . . ?
N6 N7 N8 N9 0.26(14) . . . . ?
N4 C5 N9 N8 179.74(11) . . . . ?
N6 C5 N9 N8 0.99(13) . . . . ?
N4 C5 N9 C10 -9.49(19) . . . . ?
N6 C5 N9 C10 171.76(11) . . . . ?
N7 N8 N9 C5 -0.81(15) . . . . ?
N7 N8 N9 C10 -172.56(11) . . . . ?
C5 N9 C10 C11 87.44(15) . . . . ?
N8 N9 C10 C11 -102.58(13) . . . . ?
N9 C10 C11 N12 -70.29(14) . . . . ?
C10 C11 N12 C16 112.50(14) . . . . ?
C10 C11 N12 N13 -61.31(14) . . . . ?
C16 N12 N13 C14 0.10(13) . . . . ?
C11 N12 N13 C14 174.97(10) . . . . ?
N12 N13 C14 N15 0.39(14) . . . . ?
N12 N13 C14 N17 -177.65(10) . . . . ?
N13 C14 N15 C16 -0.70(14) . . . . ?
N17 C14 N15 C16 177.33(11) . . . . ?
C14 N15 C16 N12 0.69(13) . . . . ?
N13 N12 C16 N15 -0.53(14) . . . . ?
C11 N12 C16 N15 -174.80(11) . . . . ?
N13 C14 N17 O18 6.04(17) . . . . ?
N15 C14 N17 O18 -171.93(11) . . . . ?
N13 C14 N17 O19 -175.03(11) . . . . ?
N15 C14 N17 O19 7.00(17) . . . . ?

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
C10 H10A O1 0.99 2.57 3.4866(16) 153.7 3_666
C10 H10B O1 0.99 2.43 3.2289(16) 137.0 1_455
C11 H11A O19 0.99 2.43 2.9544(16) 112.6 4_566
C16 H16 N13 0.95 2.62 3.4664(16) 149.4 4_666
N6 H6 N15 0.861(18) 1.978(18) 2.8142(16) 163.2(15) 2_656

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.050

# start Validation Reply Form
_vrf_PLAT015_shrv389             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv388
_database_code_depnum_ccdc_archive 'CCDC 1474900'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N10 O2'
_chemical_formula_sum            'C4 H6 N10 O2'
_chemical_formula_weight         226.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.042(8)
_cell_length_b                   6.453(5)
_cell_length_c                   27.04(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.147(11)
_cell_angle_gamma                90
_cell_volume                     1730(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      5.5895
_cell_measurement_theta_max      26.303

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.5848
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10025
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         5.416
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3183
_reflns_number_gt                2403
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1611P)²+5.8815P] 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         3183
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0933
_refine_ls_wR_factor_ref         0.2974
_refine_ls_wR_factor_gt          0.2689
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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
O1A O 0.2840(6) 0.8159(9) 0.3043(2) 0.0291(14) Uani 1 1 d . . . . .
O2A O 0.4657(6) 0.6283(9) 0.3133(2) 0.0293(14) Uani 1 1 d . . . . .
N3A N 0.3743(7) 0.7240(10) 0.2879(2) 0.0233(15) Uani 1 1 d . . . . .
C4A C 0.3731(8) 0.7309(12) 0.2350(3) 0.0198(17) Uani 1 1 d . . . . .
N5A N 0.2799(7) 0.8314(10) 0.2039(3) 0.0239(15) Uani 1 1 d . . . . .
N6A N 0.3122(6) 0.7984(10) 0.1591(2) 0.0209(14) Uani 1 1 d . . . . .
N7A N 0.4224(6) 0.6813(10) 0.1668(2) 0.0173(14) Uani 1 1 d . . . . .
N8A N 0.4660(6) 0.6328(9) 0.2137(2) 0.0167(13) Uani 1 1 d . . . . .
C9A C 0.4895(8) 0.6041(13) 0.1263(3) 0.0217(18) Uani 1 1 d . . . . .
H8A H 0.4920 0.4508 0.1276 0.026 Uiso 1 1 calc R U . . .
H9A H 0.5838 0.6547 0.1315 0.026 Uiso 1 1 calc R U . . .
C10A C 0.4203(8) 0.6714(12) 0.0758(3) 0.0209(17) Uani 1 1 d . . . . .
H11A H 0.4571 0.5911 0.0498 0.025 Uiso 1 1 calc R U . . .
H10A H 0.3230 0.6390 0.0728 0.025 Uiso 1 1 calc R U . . .
N11A N 0.4362(6) 0.8933(10) 0.0664(2) 0.0186(14) Uani 1 1 d . . . . .
N12A N 0.5600(7) 0.9768(11) 0.0736(2) 0.0241(16) Uani 1 1 d . . . . .
N13A N 0.5453(7) 1.1632(10) 0.0547(2) 0.0240(15) Uani 1 1 d . . . . .
N14A N 0.4147(7) 1.1986(10) 0.0354(2) 0.0219(15) Uani 1 1 d . . . . .
C15A C 0.3514(7) 1.0273(12) 0.0417(3) 0.0154(15) Uani 1 1 d . . . . .
N16A N 0.2167(6) 0.9919(11) 0.0275(2) 0.0231(15) Uani 1 1 d . . . . .
H16A H 0.1644 1.0903 0.0126 0.028 Uiso 1 1 calc R U . . .
H17A H 0.1821 0.8707 0.0333 0.028 Uiso 1 1 calc R U . . .
O1B O 0.0213(6) 0.1176(10) 0.3154(2) 0.0314(15) Uani 1 1 d . . . . .
O2B O 0.1970(6) 0.3162(10) 0.3334(2) 0.0320(15) Uani 1 1 d . . . . .
N3B N 0.1144(7) 0.2185(11) 0.3041(2) 0.0242(16) Uani 1 1 d . . . . .
C4B C 0.1274(7) 0.2297(12) 0.2520(3) 0.0179(16) Uani 1 1 d . . . . .
N5B N 0.2270(6) 0.3294(11) 0.2358(2) 0.0225(15) Uani 1 1 d . . . . .
N6B N 0.2077(7) 0.2958(11) 0.1872(3) 0.0247(16) Uani 1 1 d . . . . .
N7B N 0.0976(6) 0.1808(10) 0.1772(2) 0.0167(13) Uani 1 1 d . . . . .
N8B N 0.0431(6) 0.1322(10) 0.2175(2) 0.0157(13) Uani 1 1 d . . . . .
C9B C 0.0469(8) 0.0956(12) 0.1284(3) 0.0198(17) Uani 1 1 d . . . . .
H8B H 0.0288 -0.0540 0.1322 0.024 Uiso 1 1 calc R U . . .
H9B H 0.1177 0.1085 0.1070 0.024 Uiso 1 1 calc R U . . .
C10C C -0.0794(8) 0.1978(12) 0.1024(3) 0.0209(17) Uani 1 1 d . . . . .
H11B H -0.1251 0.1040 0.0761 0.025 Uiso 1 1 calc R U . . .
H10B H -0.1413 0.2215 0.1269 0.025 Uiso 1 1 calc R U . . .
N11B N -0.0515(6) 0.3988(10) 0.0793(2) 0.0159(14) Uani 1 1 d . . . . .
N12B N 0.0770(6) 0.4664(11) 0.0785(2) 0.0202(14) Uani 1 1 d . . . . .
N13B N 0.0617(6) 0.6418(10) 0.0557(2) 0.0208(15) Uani 1 1 d . . . . .
N14B N -0.0694(6) 0.6871(11) 0.0402(2) 0.0222(15) Uani 1 1 d . . . . .
C15B C -0.1367(7) 0.5288(11) 0.0545(3) 0.0133(15) Uani 1 1 d . . . . .
N16B N -0.2726(6) 0.5125(12) 0.0480(3) 0.0292(18) Uani 1 1 d . . . . .
H16B H -0.3105 0.4072 0.0611 0.035 Uiso 1 1 calc R U . . .
H17B H -0.3231 0.6073 0.0308 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A N3A 1.224(9) . ?
O2A N3A 1.222(9) . ?
N3A C4A 1.430(10) . ?
C4A N5A 1.324(10) . ?
C4A N8A 1.332(10) . ?
N5A N6A 1.322(10) . ?
N6A N7A 1.328(9) . ?
N7A N8A 1.313(9) . ?
N7A C9A 1.461(10) . ?
C9A C10A 1.495(10) . ?
C9A H8A 0.9900 . ?
C9A H9A 0.9900 . ?
C10A N11A 1.467(10) . ?
C10A H11A 0.9900 . ?
C10A H10A 0.9900 . ?
N11A C15A 1.318(10) . ?
N11A N12A 1.341(9) . ?
N12A N13A 1.306(10) . ?
N13A N14A 1.352(10) . ?
N14A C15A 1.300(10) . ?
C15A N16A 1.365(10) . ?
N16A H16A 0.8800 . ?
N16A H17A 0.8800 . ?
O1B N3B 1.219(9) . ?
O2B N3B 1.228(9) . ?
N3B C4B 1.436(10) . ?
C4B N8B 1.316(10) . ?
C4B N5B 1.321(10) . ?
N5B N6B 1.315(10) . ?
N6B N7B 1.324(9) . ?
N7B N8B 1.331(8) . ?
N7B C9B 1.445(9) . ?
C9B C10C 1.502(11) . ?
C9B H8B 0.9900 . ?
C9B H9B 0.9900 . ?
C10C N11B 1.486(10) . ?
C10C H11B 0.9900 . ?
C10C H10B 0.9900 . ?
N11B C15B 1.304(10) . ?
N11B N12B 1.366(9) . ?
N12B N13B 1.286(9) . ?
N13B N14B 1.349(9) . ?
N14B C15B 1.317(10) . ?
C15B N16B 1.352(9) . ?
N16B H16B 0.8800 . ?
N16B H17B 0.8800 . ?

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
O2A N3A O1A 125.1(7) . . ?
O2A N3A C4A 117.6(6) . . ?
O1A N3A C4A 117.3(7) . . ?
N5A C4A N8A 115.6(7) . . ?
N5A C4A N3A 122.9(7) . . ?
N8A C4A N3A 121.5(7) . . ?
N6A N5A C4A 104.5(6) . . ?
N5A N6A N7A 105.5(6) . . ?
N8A N7A N6A 115.4(6) . . ?
N8A N7A C9A 121.3(6) . . ?
N6A N7A C9A 123.3(6) . . ?
N7A N8A C4A 98.9(6) . . ?
N7A C9A C10A 112.5(6) . . ?
N7A C9A H8A 109.1 . . ?
C10A C9A H8A 109.1 . . ?
N7A C9A H9A 109.1 . . ?
C10A C9A H9A 109.1 . . ?
H8A C9A H9A 107.8 . . ?
N11A C10A C9A 113.3(6) . . ?
N11A C10A H11A 108.9 . . ?
C9A C10A H11A 108.9 . . ?
N11A C10A H10A 108.9 . . ?
C9A C10A H10A 108.9 . . ?
H11A C10A H10A 107.7 . . ?
C15A N11A N12A 108.6(6) . . ?
C15A N11A C10A 130.5(7) . . ?
N12A N11A C10A 119.4(7) . . ?
N13A N12A N11A 105.6(7) . . ?
N12A N13A N14A 110.5(7) . . ?
C15A N14A N13A 105.7(6) . . ?
N14A C15A N11A 109.6(6) . . ?
N14A C15A N16A 126.1(7) . . ?
N11A C15A N16A 124.3(7) . . ?
C15A N16A H16A 120.0 . . ?
C15A N16A H17A 120.0 . . ?
H16A N16A H17A 120.0 . . ?
O1B N3B O2B 125.3(7) . . ?
O1B N3B C4B 117.8(6) . . ?
O2B N3B C4B 116.8(7) . . ?
N8B C4B N5B 115.7(7) . . ?
N8B C4B N3B 121.5(7) . . ?
N5B C4B N3B 122.7(7) . . ?
N6B N5B C4B 104.6(6) . . ?
N5B N6B N7B 106.4(6) . . ?
N6B N7B N8B 113.8(6) . . ?
N6B N7B C9B 124.2(6) . . ?
N8B N7B C9B 121.7(6) . . ?
C4B N8B N7B 99.5(6) . . ?
N7B C9B C10C 114.1(6) . . ?
N7B C9B H8B 108.7 . . ?
C10C C9B H8B 108.7 . . ?
N7B C9B H9B 108.7 . . ?
C10C C9B H9B 108.7 . . ?
H8B C9B H9B 107.6 . . ?
N11B C10C C9B 112.3(6) . . ?
N11B C10C H11B 109.2 . . ?
C9B C10C H11B 109.2 . . ?
N11B C10C H10B 109.2 . . ?
C9B C10C H10B 109.2 . . ?
H11B C10C H10B 107.9 . . ?
C15B N11B N12B 109.4(6) . . ?
C15B N11B C10C 128.7(6) . . ?
N12B N11B C10C 121.8(6) . . ?
N13B N12B N11B 104.3(6) . . ?
N12B N13B N14B 112.1(6) . . ?
C15B N14B N13B 105.1(6) . . ?
N11B C15B N14B 108.9(6) . . ?
N11B C15B N16B 125.6(7) . . ?
N14B C15B N16B 125.2(7) . . ?
C15B N16B H16B 120.0 . . ?
C15B N16B H17B 120.0 . . ?
H16B N16B H17B 120.0 . . ?

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
O2A N3A C4A N5A -179.4(7) . . . . ?
O1A N3A C4A N5A 0.2(11) . . . . ?
O2A N3A C4A N8A 1.6(11) . . . . ?
O1A N3A C4A N8A -178.9(7) . . . . ?
N8A C4A N5A N6A 0.1(9) . . . . ?
N3A C4A N5A N6A -179.0(7) . . . . ?
C4A N5A N6A N7A -0.1(8) . . . . ?
N5A N6A N7A N8A 0.2(8) . . . . ?
N5A N6A N7A C9A 178.2(7) . . . . ?
N6A N7A N8A C4A -0.1(8) . . . . ?
C9A N7A N8A C4A -178.2(7) . . . . ?
N5A C4A N8A N7A 0.0(8) . . . . ?
N3A C4A N8A N7A 179.2(7) . . . . ?
N8A N7A C9A C10A 177.8(7) . . . . ?
N6A N7A C9A C10A -0.1(10) . . . . ?
N7A C9A C10A N11A 70.9(9) . . . . ?
C9A C10A N11A C15A -144.0(8) . . . . ?
C9A C10A N11A N12A 51.7(9) . . . . ?
C15A N11A N12A N13A 2.4(8) . . . . ?
C10A N11A N12A N13A 169.8(6) . . . . ?
N11A N12A N13A N14A -0.3(8) . . . . ?
N12A N13A N14A C15A -1.8(8) . . . . ?
N13A N14A C15A N11A 3.3(8) . . . . ?
N13A N14A C15A N16A -179.6(7) . . . . ?
N12A N11A C15A N14A -3.6(8) . . . . ?
C10A N11A C15A N14A -169.2(7) . . . . ?
N12A N11A C15A N16A 179.3(7) . . . . ?
C10A N11A C15A N16A 13.7(12) . . . . ?
O1B N3B C4B N8B -0.9(11) . . . . ?
O2B N3B C4B N8B -179.3(7) . . . . ?
O1B N3B C4B N5B -177.8(7) . . . . ?
O2B N3B C4B N5B 3.8(11) . . . . ?
N8B C4B N5B N6B -0.1(9) . . . . ?
N3B C4B N5B N6B 177.0(7) . . . . ?
C4B N5B N6B N7B 0.8(8) . . . . ?
N5B N6B N7B N8B -1.2(8) . . . . ?
N5B N6B N7B C9B -175.0(7) . . . . ?
N5B C4B N8B N7B -0.6(8) . . . . ?
N3B C4B N8B N7B -177.7(7) . . . . ?
N6B N7B N8B C4B 1.1(8) . . . . ?
C9B N7B N8B C4B 175.0(7) . . . . ?
N6B N7B C9B C10C -108.2(8) . . . . ?
N8B N7B C9B C10C 78.5(9) . . . . ?
N7B C9B C10C N11B 78.7(8) . . . . ?
C9B C10C N11B C15B -179.1(7) . . . . ?
C9B C10C N11B N12B 5.8(10) . . . . ?
C15B N11B N12B N13B 3.8(8) . . . . ?
C10C N11B N12B N13B 179.7(6) . . . . ?
N11B N12B N13B N14B -2.2(8) . . . . ?
N12B N13B N14B C15B -0.1(8) . . . . ?
N12B N11B C15B N14B -4.0(8) . . . . ?
C10C N11B C15B N14B -179.6(7) . . . . ?
N12B N11B C15B N16B -179.1(7) . . . . ?
C10C N11B C15B N16B 5.3(12) . . . . ?
N13B N14B C15B N11B 2.5(8) . . . . ?
N13B N14B C15B N16B 177.7(7) . . . . ?

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
C9A H8A O2A 0.99 2.62 3.472(10) 144.7 2_645
C9A H9A O2B 0.99 2.48 3.447(10) 164.1 2_655
C10A H11A N14A 0.99 2.59 3.238(10) 123.3 1_545
C10A H10A N13B 0.99 2.59 3.561(11) 166.4 .
N16A H16A N14B 0.88 2.14 2.994(9) 164.0 3_575
N16A H17A N13B 0.88 2.06 2.913(9) 163.1 .
C9B H8B O1B 0.99 2.64 3.552(10) 153.0 2_545
C9B H9B N16A 0.99 2.62 3.503(10) 149.2 1_545
C10C H10B O1A 0.99 2.59 3.579(10) 173.4 2_545
N16B H16B N13A 0.88 2.13 2.926(10) 150.6 1_445
N16B H17B N14A 0.88 2.26 3.094(10) 159.2 3_575

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.117

# start Validation Reply Form
_vrf_PLAT015_shrv388             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless  specifically required.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv395
_database_code_depnum_ccdc_archive 'CCDC 1474901'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N14 O2'
_chemical_formula_sum            'C6 H6 N14 O2'
_chemical_formula_weight         306.25

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   14.8551(19)
_cell_length_b                   5.9407(7)
_cell_length_c                   28.617(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.001(9)
_cell_angle_gamma                90
_cell_volume                     2439.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      22.66

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_T_max  0.7461

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13809
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         30.627
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3524
_reflns_number_gt                1957
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0871P)²+0.1562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3524
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.10221(16) 0.2257(4) 0.01597(8) 0.0234(5) Uani 1 1 d . . . . .
H1A H 0.044(2) 0.219(5) 0.0035(11) 0.028 Uiso 1 1 d . U . . .
H1B H 0.126(2) 0.340(5) 0.0290(10) 0.028 Uiso 1 1 d . U . . .
C2 C 0.14372(17) 0.0303(4) 0.03275(9) 0.0190(5) Uani 1 1 d . . . . .
N3 N 0.10477(15) -0.1728(3) 0.02510(8) 0.0245(5) Uani 1 1 d . . . . .
N4 N 0.17336(16) -0.3191(3) 0.04686(8) 0.0275(5) Uani 1 1 d . . . . .
N5 N 0.25025(15) -0.2184(3) 0.06655(8) 0.0245(5) Uani 1 1 d . . . . .
N6 N 0.23318(14) 0.0060(3) 0.05779(7) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.30624(17) 0.1691(4) 0.07811(9) 0.0198(5) Uani 1 1 d . . . . .
H7A H 0.2882 0.3176 0.0629 0.024 Uiso 1 1 calc R U . . .
H7B H 0.3647 0.1220 0.0704 0.024 Uiso 1 1 calc R U . . .
C8 C 0.32384(17) 0.1920(4) 0.13275(9) 0.0209(5) Uani 1 1 d . . . . .
H8A H 0.3259 0.0403 0.1473 0.025 Uiso 1 1 calc R U . . .
H8B H 0.3853 0.2639 0.1460 0.025 Uiso 1 1 calc R U . . .
N9 N 0.25230(14) 0.3252(3) 0.14629(7) 0.0201(5) Uani 1 1 d . . . . .
N10 N 0.16111(14) 0.2563(4) 0.13010(8) 0.0242(5) Uani 1 1 d . . . . .
C11 C 0.11147(18) 0.4144(4) 0.14471(9) 0.0237(6) Uani 1 1 d . . . . .
N12 N 0.01414(15) 0.4026(4) 0.13379(9) 0.0300(5) Uani 1 1 d . . . . .
N13 N -0.01541(15) 0.2208(4) 0.11236(8) 0.0288(5) Uani 1 1 d . . . . .
N14 N -0.05025(17) 0.0687(4) 0.09228(9) 0.0379(6) Uani 1 1 d . . . . .
C15 C 0.16954(18) 0.5855(4) 0.17050(9) 0.0222(6) Uani 1 1 d . . . . .
N16 N 0.14309(16) 0.7802(4) 0.19197(8) 0.0276(5) Uani 1 1 d . . . . .
O17 O 0.05975(14) 0.8176(4) 0.18705(8) 0.0415(6) Uani 1 1 d . . . . .
O18 O 0.20671(14) 0.9045(3) 0.21516(7) 0.0365(5) Uani 1 1 d . . . . .
C19 C 0.26142(18) 0.5197(4) 0.17087(9) 0.0213(5) Uani 1 1 d . . . . .
N20 N 0.34898(15) 0.6081(4) 0.18479(8) 0.0294(5) Uani 1 1 d . . . . .
N21 N 0.37151(16) 0.7309(4) 0.22177(8) 0.0299(5) Uani 1 1 d . . . . .
N22 N 0.40572(19) 0.8421(5) 0.25289(10) 0.0496(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.343(3) . ?
N1 H1A 0.85(3) . ?
N1 H1B 0.81(3) . ?
C2 N3 1.332(3) . ?
C2 N6 1.344(3) . ?
N3 N4 1.361(3) . ?
N4 N5 1.283(3) . ?
N5 N6 1.368(3) . ?
N6 C7 1.459(3) . ?
C7 C8 1.523(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N9 1.456(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N9 C19 1.341(3) . ?
N9 N10 1.376(3) . ?
N10 C11 1.327(3) . ?
C11 N12 1.400(3) . ?
C11 C15 1.411(4) . ?
N12 N13 1.263(3) . ?
N13 N14 1.123(3) . ?
C15 N16 1.413(3) . ?
C15 C19 1.417(4) . ?
N16 O17 1.229(3) . ?
N16 O18 1.247(3) . ?
C19 N20 1.363(3) . ?
N20 N21 1.257(3) . ?
N21 N22 1.120(3) . ?

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
C2 N1 H1A 116(2) . . ?
C2 N1 H1B 117(2) . . ?
H1A N1 H1B 120(3) . . ?
N3 C2 N1 125.8(2) . . ?
N3 C2 N6 108.5(2) . . ?
N1 C2 N6 125.6(2) . . ?
C2 N3 N4 105.2(2) . . ?
N5 N4 N3 112.26(19) . . ?
N4 N5 N6 105.81(19) . . ?
C2 N6 N5 108.23(19) . . ?
C2 N6 C7 132.2(2) . . ?
N5 N6 C7 119.39(19) . . ?
N6 C7 C8 112.38(19) . . ?
N6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N9 C8 C7 112.26(19) . . ?
N9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C19 N9 N10 113.0(2) . . ?
C19 N9 C8 128.8(2) . . ?
N10 N9 C8 118.14(19) . . ?
C11 N10 N9 105.2(2) . . ?
N10 C11 N12 121.3(2) . . ?
N10 C11 C15 111.1(2) . . ?
N12 C11 C15 127.5(2) . . ?
N13 N12 C11 111.1(2) . . ?
N14 N13 N12 173.1(3) . . ?
C11 C15 N16 128.0(2) . . ?
C11 C15 C19 105.2(2) . . ?
N16 C15 C19 126.8(2) . . ?
O17 N16 O18 123.8(2) . . ?
O17 N16 C15 118.9(2) . . ?
O18 N16 C15 117.3(2) . . ?
N9 C19 N20 116.4(2) . . ?
N9 C19 C15 105.5(2) . . ?
N20 C19 C15 137.8(2) . . ?
N21 N20 C19 119.7(2) . . ?
N22 N21 N20 168.2(3) . . ?

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
N1 C2 N3 N4 177.3(2) . . . . ?
N6 C2 N3 N4 0.7(3) . . . . ?
C2 N3 N4 N5 -0.5(3) . . . . ?
N3 N4 N5 N6 0.0(3) . . . . ?
N3 C2 N6 N5 -0.8(3) . . . . ?
N1 C2 N6 N5 -177.4(2) . . . . ?
N3 C2 N6 C7 -176.1(2) . . . . ?
N1 C2 N6 C7 7.3(4) . . . . ?
N4 N5 N6 C2 0.5(3) . . . . ?
N4 N5 N6 C7 176.5(2) . . . . ?
C2 N6 C7 C8 104.0(3) . . . . ?
N5 N6 C7 C8 -71.0(3) . . . . ?
N6 C7 C8 N9 -76.7(3) . . . . ?
C7 C8 N9 C19 -118.6(3) . . . . ?
C7 C8 N9 N10 57.1(3) . . . . ?
C19 N9 N10 C11 0.6(3) . . . . ?
C8 N9 N10 C11 -175.8(2) . . . . ?
N9 N10 C11 N12 178.8(2) . . . . ?
N9 N10 C11 C15 -0.3(3) . . . . ?
N10 C11 N12 N13 4.5(4) . . . . ?
C15 C11 N12 N13 -176.6(2) . . . . ?
N10 C11 C15 N16 -179.5(2) . . . . ?
N12 C11 C15 N16 1.5(4) . . . . ?
N10 C11 C15 C19 -0.1(3) . . . . ?
N12 C11 C15 C19 -179.1(2) . . . . ?
C11 C15 N16 O17 -3.1(4) . . . . ?
C19 C15 N16 O17 177.6(2) . . . . ?
C11 C15 N16 O18 176.7(3) . . . . ?
C19 C15 N16 O18 -2.6(4) . . . . ?
N10 N9 C19 N20 -175.0(2) . . . . ?
C8 N9 C19 N20 0.9(4) . . . . ?
N10 N9 C19 C15 -0.6(3) . . . . ?
C8 N9 C19 C15 175.2(2) . . . . ?
C11 C15 C19 N9 0.4(3) . . . . ?
N16 C15 C19 N9 179.8(2) . . . . ?
C11 C15 C19 N20 172.9(3) . . . . ?
N16 C15 C19 N20 -7.7(5) . . . . ?
N9 C19 N20 N21 -152.4(2) . . . . ?
C15 C19 N20 N21 35.7(5) . . . . ?
C19 N20 N21 N22 179.7(13) . . . . ?

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
C8 H8B O17 0.99 2.57 3.526(3) 161.5 3_545
N1 H1A N3 0.85(3) 2.17(3) 3.010(3) 175(3) 5
N1 H1B N4 0.81(3) 2.16(3) 2.954(3) 166(3) 1_565

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.073

# start Validation Reply Form
_vrf_PLAT015_shrv395             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
