# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_js1016b
_database_code_depnum_ccdc_archive 'CCDC 1510571'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N5 O4, H4 N'
_chemical_formula_sum            'C3 H4 N6 O4'
_chemical_formula_weight         188.12
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   4.93750(10)
_cell_length_b                   7.6501(2)
_cell_length_c                   17.8893(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     675.72(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2111
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      6.29
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0530 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.8815. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2752
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.072
_diffrn_reflns_theta_min         4.944
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.544
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                1168
_reflns_number_total             1241
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.24(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.0407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0676
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.7017(4) 0.1061(2) 0.73032(9) 0.0281(4) Uani 1 1 d . . . . .
O2 O 0.5308(3) 0.67467(19) 0.56671(9) 0.0238(4) Uani 1 1 d . . . . .
O3 O 0.1056(3) 0.4892(2) 0.50930(8) 0.0230(4) Uani 1 1 d . . . . .
O4 O 0.0508(3) 0.22910(19) 0.55691(9) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.5574(4) 0.5368(2) 0.60507(10) 0.0179(4) Uani 1 1 d . . . . .
N2 N 0.7566(4) 0.5265(2) 0.65579(10) 0.0213(4) Uani 1 1 d . . . . .
N3 N 0.4872(4) 0.1100(2) 0.67784(11) 0.0246(4) Uani 1 1 d . . . . .
N4 N 0.8452(4) 0.2639(3) 0.73367(11) 0.0256(5) Uani 1 1 d . . . . .
N5 N 0.1734(4) 0.3705(2) 0.55217(10) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.3944(4) 0.3887(3) 0.59984(11) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.5039(4) 0.2687(3) 0.65082(12) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.7215(5) 0.3607(3) 0.68405(12) 0.0195(5) Uani 1 1 d . . . . .
N6 N 0.5373(5) 0.6388(3) 0.39763(12) 0.0196(4) Uani 1 1 d . . . . .
H6A H 0.533(7) 0.675(4) 0.355(2) 0.037(9) Uiso 1 1 d . . . . .
H6B H 0.672(7) 0.698(4) 0.4152(16) 0.029(8) Uiso 1 1 d . . . . .
H6C H 0.409(9) 0.670(6) 0.415(2) 0.074(15) Uiso 1 1 d . . . . .
H6D H 0.574(7) 0.533(5) 0.4017(19) 0.050(10) 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 N3 1.416(3) . ?
O1 N4 1.401(3) . ?
O2 N1 1.265(2) . ?
O3 N5 1.234(2) . ?
O4 N5 1.242(2) . ?
N1 N2 1.341(3) . ?
N1 C1 1.393(3) . ?
N2 C3 1.377(3) . ?
N3 C2 1.309(3) . ?
N4 C3 1.307(3) . ?
N5 C1 1.392(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.415(3) . ?
N6 H6A 0.81(4) . ?
N6 H6B 0.86(3) . ?
N6 H6C 0.75(5) . ?
N6 H6D 0.83(4) . ?

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
N4 O1 N3 112.84(16) . . ?
O2 N1 N2 119.51(18) . . ?
O2 N1 C1 125.57(18) . . ?
N2 N1 C1 114.92(17) . . ?
N1 N2 C3 102.14(17) . . ?
C2 N3 O1 102.57(18) . . ?
C3 N4 O1 102.88(18) . . ?
O3 N5 O4 123.42(18) . . ?
O3 N5 C1 121.30(17) . . ?
O4 N5 C1 115.28(17) . . ?
N1 C1 C2 105.45(18) . . ?
N5 C1 N1 125.12(18) . . ?
N5 C1 C2 129.43(19) . . ?
N3 C2 C1 145.4(2) . . ?
N3 C2 C3 110.7(2) . . ?
C1 C2 C3 103.90(18) . . ?
N2 C3 C2 113.55(19) . . ?
N4 C3 N2 135.4(2) . . ?
N4 C3 C2 111.0(2) . . ?
H6A N6 H6B 101(3) . . ?
H6A N6 H6C 106(4) . . ?
H6A N6 H6D 115(3) . . ?
H6B N6 H6C 109(3) . . ?
H6B N6 H6D 108(3) . . ?
H6C N6 H6D 117(4) . . ?

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
N6 H6A N2 0.81(4) 2.67(3) 3.064(3) 112(3) 4_466
N6 H6A N4 0.81(4) 2.30(4) 3.081(3) 162(3) 2_664
N6 H6B O2 0.86(3) 2.05(4) 2.894(3) 167(3) 4_566
N6 H6C O2 0.75(5) 2.24(5) 2.949(3) 159(4) 4_466
N6 H6D O4 0.83(4) 2.14(4) 2.931(3) 158(3) 4_556

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
O1 N3 C2 C1 179.0(3) . . . . ?
O1 N3 C2 C3 0.7(2) . . . . ?
O1 N4 C3 N2 -177.3(2) . . . . ?
O1 N4 C3 C2 0.8(2) . . . . ?
O2 N1 N2 C3 -179.15(18) . . . . ?
O2 N1 C1 N5 -1.1(3) . . . . ?
O2 N1 C1 C2 178.24(19) . . . . ?
O3 N5 C1 N1 0.5(3) . . . . ?
O3 N5 C1 C2 -178.7(2) . . . . ?
O4 N5 C1 N1 -178.71(19) . . . . ?
O4 N5 C1 C2 2.1(3) . . . . ?
N1 N2 C3 N4 178.5(2) . . . . ?
N1 N2 C3 C2 0.4(2) . . . . ?
N1 C1 C2 N3 -176.5(3) . . . . ?
N1 C1 C2 C3 1.8(2) . . . . ?
N2 N1 C1 N5 178.91(18) . . . . ?
N2 N1 C1 C2 -1.8(2) . . . . ?
N3 O1 N4 C3 -0.4(2) . . . . ?
N3 C2 C3 N2 177.55(19) . . . . ?
N3 C2 C3 N4 -1.0(3) . . . . ?
N4 O1 N3 C2 -0.2(2) . . . . ?
N5 C1 C2 N3 2.7(5) . . . . ?
N5 C1 C2 C3 -178.9(2) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
C1 C2 C3 N2 -1.4(3) . . . . ?
C1 C2 C3 N4 179.99(18) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TANG-66
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js1016c
_database_code_depnum_ccdc_archive 'CCDC 1510572'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_audit_creation_date             2016-10-18
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 K N5 O4'
_chemical_formula_sum            'C3 K N5 O4'
_chemical_formula_weight         209.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.0130(2)
_cell_length_b                   8.8704(2)
_cell_length_c                   10.5190(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.172(2)
_cell_angle_gamma                90
_cell_volume                     654.23(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3940
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      6.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.184
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0826 before and 0.0589 after correction. The Ratio of minimum to maximum transmission is 0.8361. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.124
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8193
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.353
_diffrn_reflns_theta_min         6.312
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1095
_reflns_number_total             1271
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.260
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0092P)²+3.6482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(C3B)
Uanis(C2B) = Uanis(C2A)
Uanis(C1A) = Uanis(C1B)
Uanis(N2B) = Uanis(N1A)
Uanis(N1B) = Uanis(N2A)
Uanis(O1B) = Uanis(O1A)
Uanis(N3B) = Uanis(N3A)
Uanis(N4B) = Uanis(N4A)
Uanis(O2A) = Uanis(O2B)
Uanis(O4A) = Uanis(O3B)
Uanis(O3A) = Uanis(O4B)
Uanis(N5B) = Uanis(N5A)
2. Others
 Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(N1B)=Sof(N2B)=Sof(N3B)=Sof(N4B)=
 Sof(N5B)=Sof(C1B)=Sof(C2B)=Sof(C3B)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(N4A)=
 Sof(N5A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=FVAR(1)
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
K1 K 0.76791(17) 0.74061(13) 0.26891(11) 0.0270(3) Uani 1 1 d . . . . .
O1A O 0.8257(7) -0.0198(5) 0.5692(4) 0.0211(11) Uani 0.843(4) 1 d . . P A 1
O2A O 0.5755(11) 0.4645(6) 0.3258(8) 0.0189(14) Uani 0.843(4) 1 d . . P A 1
O3A O 0.7626(7) 0.6218(6) 0.5200(4) 0.0157(10) Uani 0.843(4) 1 d . . P A 1
O4A O 0.9052(13) 0.4690(5) 0.6630(9) 0.0207(15) Uani 0.843(4) 1 d . . P A 1
N1A N 0.7157(9) -0.0159(7) 0.4549(7) 0.0245(15) Uani 0.843(4) 1 d . . P A 1
N2A N 0.8661(8) 0.1261(6) 0.6153(5) 0.0190(11) Uani 0.843(4) 1 d . . P A 1
N3A N 0.6028(7) 0.2161(5) 0.3437(5) 0.0180(10) Uani 0.843(4) 1 d . . P A 1
N4A N 0.6392(6) 0.3564(5) 0.3852(4) 0.0145(10) Uani 0.843(4) 1 d . . P A 1
N5A N 0.8057(6) 0.4932(5) 0.5599(4) 0.0159(10) Uani 0.843(4) 1 d . . P A 1
C1A C 0.6947(9) 0.1275(7) 0.4359(6) 0.0164(12) Uani 0.843(4) 1 d . . P A 1
C2A C 0.7853(7) 0.2143(6) 0.5313(5) 0.0121(11) Uani 0.843(4) 1 d . . P A 1
C3A C 0.750(3) 0.365(2) 0.4962(14) 0.014(2) Uani 0.843(4) 1 d . . P A 1
O1B O 0.656(4) -0.021(4) 0.434(4) 0.0211(11) Uani 0.157(4) 1 d . . P A 2
O2B O 0.905(8) 0.505(5) 0.659(6) 0.0189(14) Uani 0.157(4) 1 d . . P A 2
O3B O 0.729(5) 0.619(4) 0.482(3) 0.0207(15) Uani 0.157(4) 1 d . . P A 2
O4B O 0.589(8) 0.497(5) 0.339(5) 0.0157(10) Uani 0.157(4) 1 d . . P A 2
N1B N 0.766(5) -0.018(4) 0.537(4) 0.0190(11) Uani 0.157(4) 1 d . . P A 2
N2B N 0.624(5) 0.132(4) 0.390(3) 0.0245(15) Uani 0.157(4) 1 d . . P A 2
N3B N 0.882(4) 0.207(3) 0.659(3) 0.0180(10) Uani 0.157(4) 1 d . . P A 2
N4B N 0.846(3) 0.347(3) 0.618(2) 0.0145(10) Uani 0.157(4) 1 d . . P A 2
N5B N 0.686(3) 0.493(3) 0.447(2) 0.0159(10) Uani 0.157(4) 1 d . . P A 2
C1B C 0.780(5) 0.127(4) 0.564(4) 0.0164(12) Uani 0.157(4) 1 d . . P A 2
C2B C 0.702(4) 0.210(4) 0.474(3) 0.0121(11) Uani 0.157(4) 1 d . . P A 2
C3B C 0.74(2) 0.352(15) 0.517(10) 0.014(2) Uani 0.157(4) 1 d . . P A 2


_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
K1 O1A 2.907(5) 4_565 ?
K1 O2A 2.866(6) . ?
K1 O3A 2.845(5) . ?
K1 O3A 2.889(5) 4_575 ?
K1 N1A 2.942(7) 1_565 ?
K1 N3A 2.843(5) 2_655 ?
K1 O1B 2.86(4) 1_565 ?
K1 O2B 2.72(5) 4_575 ?
K1 O3B 2.51(4) . ?
K1 O4B 2.61(4) . ?
K1 N3B 2.60(3) 3_766 ?
K1 N5B 2.95(3) . ?
O1A K1 2.907(5) 4_566 ?
O1A N1A 1.415(7) . ?
O1A N2A 1.409(7) . ?
O2A K1 3.262(6) 2_645 ?
O2A N4A 1.223(9) . ?
O3A K1 2.889(5) 4_576 ?
O3A N5A 1.250(7) . ?
O4A K1 3.026(8) 3_766 ?
O4A K1 2.975(6) 4_576 ?
O4A N5A 1.296(10) . ?
N1A K1 2.942(7) 1_545 ?
N1A C1A 1.295(9) . ?
N2A K1 3.056(6) 3_766 ?
N2A C2A 1.302(8) . ?
N3A K1 2.843(5) 2_645 ?
N3A N4A 1.341(6) . ?
N3A C1A 1.396(8) . ?
N4A K1 3.412(5) 2_645 ?
N4A C3A 1.391(19) . ?
N5A K1 3.241(5) 4_576 ?
N5A C3A 1.37(2) . ?
C1A C2A 1.407(8) . ?
C2A C3A 1.41(2) . ?
O1B K1 2.86(4) 1_545 ?
O1B N1B 1.31(4) . ?
O1B N2B 1.45(5) . ?
O2B K1 3.24(5) 3_766 ?
O2B K1 2.72(5) 4_576 ?
O2B N4B 1.52(5) . ?
O3B K1 3.27(3) 4_576 ?
O3B N5B 1.22(5) . ?
O4B N5B 1.31(6) . ?
N1B K1 3.14(4) 4_566 ?
N1B C1B 1.32(5) . ?
N2B K1 3.33(4) 2_645 ?
N2B C2B 1.25(5) . ?
N3B K1 2.60(3) 3_766 ?
N3B N4B 1.33(4) . ?
N3B C1B 1.41(4) . ?
N4B K1 3.03(2) 3_766 ?
N4B C3B 1.29(12) . ?
N5B C3B 1.50(12) . ?
C1B C2B 1.31(5) . ?
C2B C3B 1.35(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
O1A K1 N1A 175.12(17) 4_565 1_565 ?
O2A K1 O1A 69.41(18) . 4_565 ?
O2A K1 O3A 123.59(19) . 4_575 ?
O2A K1 N1A 115.0(2) . 1_565 ?
O3A K1 O1A 115.22(14) . 4_565 ?
O3A K1 O1A 68.21(13) 4_575 4_565 ?
O3A K1 O2A 58.27(19) . . ?
O3A K1 O3A 176.43(12) . 4_575 ?
O3A K1 N1A 107.04(16) 4_575 1_565 ?
O3A K1 N1A 69.54(17) . 1_565 ?
N3A K1 O1A 77.70(15) 2_655 4_565 ?
N3A K1 O2A 65.88(18) 2_655 . ?
N3A K1 O3A 109.24(15) 2_655 . ?
N3A K1 O3A 70.11(14) 2_655 4_575 ?
N3A K1 N1A 102.02(16) 2_655 1_565 ?
O1B K1 N5B 96.1(9) 1_565 . ?
O2B K1 O1B 75.5(14) 4_575 1_565 ?
O2B K1 N5B 164.3(13) 4_575 . ?
O3B K1 O1B 74.7(11) . 1_565 ?
O3B K1 O2B 141.4(13) . 4_575 ?
O3B K1 O4B 48.0(14) . . ?
O3B K1 N3B 86.3(10) . 3_766 ?
O3B K1 N5B 24.1(9) . . ?
O4B K1 O1B 107.5(13) . 1_565 ?
O4B K1 O2B 169.2(19) . 4_575 ?
O4B K1 N5B 26.3(13) . . ?
N3B K1 O1B 87.7(9) 3_766 1_565 ?
N3B K1 O2B 68.7(13) 3_766 4_575 ?
N3B K1 O4B 121.4(14) 3_766 . ?
N3B K1 N5B 98.2(7) 3_766 . ?
N1A O1A K1 123.3(4) . 4_566 ?
N2A O1A K1 113.6(3) . 4_566 ?
N2A O1A N1A 111.8(4) . . ?
K1 O2A K1 143.6(3) . 2_645 ?
N4A O2A K1 127.4(5) . . ?
N4A O2A K1 86.5(3) . 2_645 ?
K1 O3A K1 133.23(18) . 4_576 ?
N5A O3A K1 129.9(4) . . ?
N5A O3A K1 94.7(3) . 4_576 ?
K1 O4A K1 133.9(3) 4_576 3_766 ?
N5A O4A K1 133.8(5) . 3_766 ?
N5A O4A K1 89.8(4) . 4_576 ?
O1A N1A K1 118.3(4) . 1_545 ?
C1A N1A K1 129.3(5) . 1_545 ?
C1A N1A O1A 102.4(6) . . ?
O1A N2A K1 130.9(4) . 3_766 ?
C2A N2A K1 112.8(4) . 3_766 ?
C2A N2A O1A 103.7(5) . . ?
N4A N3A K1 103.4(3) . 2_645 ?
N4A N3A C1A 102.4(4) . . ?
C1A N3A K1 137.6(4) . 2_645 ?
O2A N4A K1 72.6(3) . 2_645 ?
O2A N4A N3A 119.8(5) . . ?
O2A N4A C3A 125.1(9) . . ?
N3A N4A K1 54.2(3) . 2_645 ?
N3A N4A C3A 115.2(9) . . ?
C3A N4A K1 149.6(7) . 2_645 ?
O3A N5A K1 62.6(3) . 4_576 ?
O3A N5A O4A 123.7(5) . . ?
O3A N5A C3A 121.7(8) . . ?
O4A N5A K1 66.6(3) . 4_576 ?
O4A N5A C3A 114.6(8) . . ?
C3A N5A K1 155.2(8) . 4_576 ?
N1A C1A N3A 135.2(7) . . ?
N1A C1A C2A 112.3(6) . . ?
N3A C1A C2A 112.5(5) . . ?
N2A C2A C1A 109.8(5) . . ?
N2A C2A C3A 145.2(9) . . ?
C1A C2A C3A 105.0(9) . . ?
N4A C3A C2A 104.9(14) . . ?
N5A C3A N4A 127.4(14) . . ?
N5A C3A C2A 127.6(13) . . ?
N1B O1B K1 111(2) . 1_545 ?
N1B O1B N2B 109(3) . . ?
N2B O1B K1 123(2) . 1_545 ?
K1 O2B K1 135(2) 4_576 3_766 ?
N4B O2B K1 142(3) . 4_576 ?
N4B O2B K1 68.5(19) . 3_766 ?
K1 O3B K1 130.8(14) . 4_576 ?
N5B O3B K1 99(2) . . ?
N5B O3B K1 131(2) . 4_576 ?
N5B O4B K1 92(2) . . ?
O1B N1B K1 128(3) . 4_566 ?
O1B N1B C1B 104(4) . . ?
C1B N1B K1 116(3) . 4_566 ?
O1B N2B K1 124(2) . 2_645 ?
C2B N2B K1 123(2) . 2_645 ?
C2B N2B O1B 103(3) . . ?
N4B N3B K1 95.7(17) . 3_766 ?
N4B N3B C1B 99(2) . . ?
C1B N3B K1 139(2) . 3_766 ?
O2B N4B K1 84(2) . 3_766 ?
N3B N4B K1 58.4(14) . 3_766 ?
N3B N4B O2B 136(3) . . ?
C3B N4B K1 146(6) . 3_766 ?
C3B N4B O2B 111(6) . . ?
C3B N4B N3B 113(6) . . ?
O3B N5B K1 57.3(19) . . ?
O3B N5B O4B 111(3) . . ?
O3B N5B C3B 124(6) . . ?
O4B N5B K1 62(2) . . ?
O4B N5B C3B 125(6) . . ?
C3B N5B K1 152(5) . . ?
N1B C1B N3B 133(4) . . ?
C2B C1B N1B 111(4) . . ?
C2B C1B N3B 115(3) . . ?
N2B C2B C1B 112(4) . . ?
N2B C2B C3B 146(6) . . ?
C1B C2B C3B 102(6) . . ?
N4B C3B N5B 125(10) . . ?
N4B C3B C2B 111(9) . . ?
C2B C3B N5B 124(9) . . ?

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
K1 O1A N1A K1 -69.9(5) 4_566 . . 1_545 ?
K1 O1A N1A C1A 141.5(4) 4_566 . . . ?
K1 O1A N2A K1 76.6(5) 4_566 . . 3_766 ?
K1 O1A N2A C2A -145.7(4) 4_566 . . . ?
K1 O2A N4A K1 -165.4(6) . . . 2_645 ?
K1 O2A N4A N3A 27.6(5) 2_645 . . . ?
K1 O2A N4A N3A -137.8(5) . . . . ?
K1 O2A N4A C3A -152.2(11) 2_645 . . . ?
K1 O2A N4A C3A 42.4(13) . . . . ?
K1 O3A N5A K1 165.0(5) . . . 4_576 ?
K1 O3A N5A O4A 136.9(6) . . . . ?
K1 O3A N5A O4A -28.1(7) 4_576 . . . ?
K1 O3A N5A C3A -43.1(11) . . . . ?
K1 O3A N5A C3A 151.9(10) 4_576 . . . ?
K1 O4A N5A K1 -163.2(7) 3_766 . . 4_576 ?
K1 O4A N5A O3A 27.2(6) 4_576 . . . ?
K1 O4A N5A O3A -136.1(5) 3_766 . . . ?
K1 O4A N5A C3A -152.9(9) 4_576 . . . ?
K1 O4A N5A C3A 43.9(12) 3_766 . . . ?
K1 N1A C1A N3A 36.9(11) 1_545 . . . ?
K1 N1A C1A C2A -143.6(4) 1_545 . . . ?
K1 N2A C2A C1A 147.1(4) 3_766 . . . ?
K1 N2A C2A C3A -33.3(17) 3_766 . . . ?
K1 N3A N4A O2A -33.0(7) 2_645 . . . ?
K1 N3A N4A C3A 146.8(9) 2_645 . . . ?
K1 N3A C1A N1A 53.2(11) 2_645 . . . ?
K1 N3A C1A C2A -126.3(5) 2_645 . . . ?
K1 N4A C3A N5A -117.5(13) 2_645 . . . ?
K1 N4A C3A C2A 60(3) 2_645 . . . ?
K1 N5A C3A N4A 91.4(14) 4_576 . . . ?
K1 N5A C3A C2A -86(3) 4_576 . . . ?
K1 O1B N1B K1 -74(3) 1_545 . . 4_566 ?
K1 O1B N1B C1B 145(3) 1_545 . . . ?
K1 O1B N2B K1 77(3) 1_545 . . 2_645 ?
K1 O1B N2B C2B -137(2) 1_545 . . . ?
K1 O2B N4B K1 -138(5) 4_576 . . 3_766 ?
K1 O2B N4B N3B 29(4) 3_766 . . . ?
K1 O2B N4B N3B -108(5) 4_576 . . . ?
K1 O2B N4B C3B 74(8) 4_576 . . . ?
K1 O2B N4B C3B -148(6) 3_766 . . . ?
K1 O3B N5B K1 178(4) 4_576 . . . ?
K1 O3B N5B O4B 146(3) 4_576 . . . ?
K1 O3B N5B O4B -33(3) . . . . ?
K1 O3B N5B C3B 146(6) . . . . ?
K1 O3B N5B C3B -35(7) 4_576 . . . ?
K1 O4B N5B O3B 31(3) . . . . ?
K1 O4B N5B C3B -148(6) . . . . ?
K1 N1B C1B N3B 36(5) 4_566 . . . ?
K1 N1B C1B C2B -154(2) 4_566 . . . ?
K1 N2B C2B C1B 147(2) 2_645 . . . ?
K1 N2B C2B C3B -31(12) 2_645 . . . ?
K1 N3B N4B O2B -35(5) 3_766 . . . ?
K1 N3B N4B C3B 142(6) 3_766 . . . ?
K1 N3B C1B N1B 63(6) 3_766 . . . ?
K1 N3B C1B C2B -107(4) 3_766 . . . ?
K1 N4B C3B N5B -109(13) 3_766 . . . ?
K1 N4B C3B C2B 64(12) 3_766 . . . ?
K1 N5B C3B N4B 79(16) . . . . ?
K1 N5B C3B C2B -93(14) . . . . ?
O1A N1A C1A N3A -179.4(7) . . . . ?
O1A N1A C1A C2A 0.1(7) . . . . ?
O1A N2A C2A C1A 0.6(6) . . . . ?
O1A N2A C2A C3A -179.8(16) . . . . ?
O2A N4A C3A N5A 1(2) . . . . ?
O2A N4A C3A C2A 178.6(8) . . . . ?
O3A N5A C3A N4A -2(2) . . . . ?
O3A N5A C3A C2A -178.8(12) . . . . ?
O4A N5A C3A N4A 178.5(13) . . . . ?
O4A N5A C3A C2A 1(2) . . . . ?
N1A O1A N2A K1 -138.3(4) . . . 3_766 ?
N1A O1A N2A C2A -0.6(6) . . . . ?
N1A C1A C2A N2A -0.5(8) . . . . ?
N1A C1A C2A C3A 179.7(9) . . . . ?
N2A O1A N1A K1 148.9(4) . . . 1_545 ?
N2A O1A N1A C1A 0.3(6) . . . . ?
N2A C2A C3A N4A -178.6(8) . . . . ?
N2A C2A C3A N5A -1(3) . . . . ?
N3A N4A C3A N5A -179.0(13) . . . . ?
N3A N4A C3A C2A -1.2(15) . . . . ?
N3A C1A C2A N2A 179.1(5) . . . . ?
N3A C1A C2A C3A -0.7(10) . . . . ?
N4A N3A C1A N1A 179.5(7) . . . . ?
N4A N3A C1A C2A 0.0(6) . . . . ?
C1A N3A N4A K1 -146.0(5) . . . 2_645 ?
C1A N3A N4A O2A -179.0(6) . . . . ?
C1A N3A N4A C3A 0.8(10) . . . . ?
C1A C2A C3A N4A 1.0(13) . . . . ?
C1A C2A C3A N5A 178.8(15) . . . . ?
O1B N1B C1B N3B -177(4) . . . . ?
O1B N1B C1B C2B -7(4) . . . . ?
O1B N2B C2B C1B 1(4) . . . . ?
O1B N2B C2B C3B -177(11) . . . . ?
O2B N4B C3B N5B 1(13) . . . . ?
O2B N4B C3B C2B 174(6) . . . . ?
O3B N5B C3B N4B -4(14) . . . . ?
O3B N5B C3B C2B -176(7) . . . . ?
O4B N5B C3B N4B 175(8) . . . . ?
O4B N5B C3B C2B 3(14) . . . . ?
N1B O1B N2B K1 -151(2) . . . 2_645 ?
N1B O1B N2B C2B -5(4) . . . . ?
N1B C1B C2B N2B 4(4) . . . . ?
N1B C1B C2B C3B -177(6) . . . . ?
N2B O1B N1B K1 148(3) . . . 4_566 ?
N2B O1B N1B C1B 7(4) . . . . ?
N2B C2B C3B N4B -177(5) . . . . ?
N2B C2B C3B N5B -4(19) . . . . ?
N3B N4B C3B N5B -177(8) . . . . ?
N3B N4B C3B C2B -3(10) . . . . ?
N3B C1B C2B N2B 176(3) . . . . ?
N3B C1B C2B C3B -5(7) . . . . ?
N4B N3B C1B N1B 173(4) . . . . ?
N4B N3B C1B C2B 3(4) . . . . ?
C1B N3B N4B K1 -142(2) . . . 3_766 ?
C1B N3B N4B O2B -177(4) . . . . ?
C1B N3B N4B C3B 0(7) . . . . ?
C1B C2B C3B N4B 5(9) . . . . ?
C1B C2B C3B N5B 178(9) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TANG-67
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js1117a
_database_code_depnum_ccdc_archive 'CCDC 1527903'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N5 O4, C3 H7 N8, H2 O'
_chemical_formula_sum            'C6 H9 N13 O5'
_chemical_formula_weight         343.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   25.5961(3)
_cell_length_b                   6.68480(10)
_cell_length_c                   15.1714(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2595.90(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4065
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.92
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.688
_exptl_absorpt_coefficient_mu    1.330
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0723 before and 0.0617 after correction. The Ratio of minimum to maximum transmission is 0.8752. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15135
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.123
_diffrn_reflns_theta_min         3.453
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1872
_reflns_number_total             2461
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.5073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.35290(5) 0.6745(2) 0.54768(10) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.55700(5) 0.7721(3) 0.50037(10) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.37868(5) 0.6576(3) 0.72331(11) 0.0321(4) Uani 1 1 d . . . . .
O4 O 0.46242(6) 0.6648(3) 0.74983(11) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.40133(6) 0.7021(3) 0.54112(12) 0.0216(4) Uani 1 1 d . . . . .
N2 N 0.42241(6) 0.7346(3) 0.46085(12) 0.0234(4) Uani 1 1 d . . . . .
N3 N 0.51794(6) 0.7766(3) 0.43525(13) 0.0267(4) Uani 1 1 d . . . . .
N4 N 0.53617(6) 0.7419(3) 0.58551(13) 0.0256(4) Uani 1 1 d . . . . .
N5 N 0.42477(6) 0.6714(3) 0.69891(12) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.43685(7) 0.7000(3) 0.61057(14) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.48589(7) 0.7294(3) 0.57119(15) 0.0209(4) Uani 1 1 d . . . . .
C3 C 0.47487(7) 0.7508(3) 0.48011(14) 0.0207(4) Uani 1 1 d . . . . .
N6 N 0.14861(6) 0.3974(3) 0.63140(12) 0.0233(4) Uani 1 1 d . . . . .
N7 N 0.20046(6) 0.4538(3) 0.64717(11) 0.0211(4) Uani 1 1 d . . . . .
N8 N 0.28011(6) 0.5316(3) 0.66016(13) 0.0250(4) Uani 1 1 d . . . . .
N9 N 0.26210(6) 0.5135(3) 0.74743(12) 0.0235(4) Uani 1 1 d . . . . .
N10 N 0.16842(6) 0.4233(3) 0.77786(11) 0.0209(4) Uani 1 1 d . . . . .
N11 N 0.24705(7) 0.4994(3) 0.51278(14) 0.0325(5) Uani 1 1 d . . . . .
N12 N 0.16170(7) 0.4467(3) 0.86878(12) 0.0255(4) Uani 1 1 d . . . . .
N13 N 0.08174(7) 0.3430(3) 0.73507(14) 0.0295(5) Uani 1 1 d . . . . .
C4 C 0.13095(7) 0.3837(3) 0.71295(14) 0.0210(4) Uani 1 1 d . . . . .
C5 C 0.24348(7) 0.4966(3) 0.59925(15) 0.0231(5) Uani 1 1 d . . . . .
C6 C 0.21321(7) 0.4683(3) 0.73339(14) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.3116(10) 0.562(4) 0.6523(17) 0.029(7) Uiso 1 1 d . . . . .
H11A H 0.2766(11) 0.522(4) 0.4869(19) 0.044(8) Uiso 1 1 d . . . . .
H11B H 0.2197(11) 0.489(4) 0.4809(19) 0.043(8) Uiso 1 1 d . . . . .
H12A H 0.1356(10) 0.541(4) 0.8768(18) 0.040(7) Uiso 1 1 d . . . . .
H12B H 0.1547(10) 0.324(4) 0.8911(18) 0.038(8) Uiso 1 1 d . . . . .
H13A H 0.0592(9) 0.322(4) 0.6903(18) 0.029(7) Uiso 1 1 d . . . . .
H13B H 0.0723(10) 0.314(4) 0.7891(18) 0.032(7) Uiso 1 1 d . . . . .
O1S O 0.16259(7) 0.4805(3) 0.39412(12) 0.0330(4) Uani 1 1 d . . . . .
H1SA H 0.1761(12) 0.507(5) 0.346(2) 0.062(11) Uiso 1 1 d . . . . .
H1SB H 0.1353(14) 0.554(6) 0.402(3) 0.082(13) 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 N1 1.257(2) . ?
O2 N3 1.406(2) . ?
O2 N4 1.412(2) . ?
O3 N5 1.240(2) . ?
O4 N5 1.236(2) . ?
N1 N2 1.350(2) . ?
N1 C1 1.392(3) . ?
N2 C3 1.378(2) . ?
N3 C3 1.307(3) . ?
N4 C2 1.308(2) . ?
N5 C1 1.389(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.418(3) . ?
N6 N7 1.400(2) . ?
N6 C4 1.321(3) . ?
N7 C5 1.350(2) . ?
N7 C6 1.352(3) . ?
N8 N9 1.407(3) . ?
N8 C5 1.337(3) . ?
N8 H8 0.84(2) . ?
N9 C6 1.305(3) . ?
N10 N12 1.399(2) . ?
N10 C4 1.400(3) . ?
N10 C6 1.364(3) . ?
N11 C5 1.315(3) . ?
N11 H11A 0.87(3) . ?
N11 H11B 0.85(3) . ?
N12 H12A 0.93(3) . ?
N12 H12B 0.90(3) . ?
N13 C4 1.332(3) . ?
N13 H13A 0.90(3) . ?
N13 H13B 0.88(3) . ?
O1S H1SA 0.83(4) . ?
O1S H1SB 0.86(4) . ?

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
N3 O2 N4 112.18(13) . . ?
O1 N1 N2 119.29(17) . . ?
O1 N1 C1 125.64(17) . . ?
N2 N1 C1 115.07(16) . . ?
N1 N2 C3 102.16(16) . . ?
C3 N3 O2 103.36(17) . . ?
C2 N4 O2 103.21(17) . . ?
O3 N5 C1 120.68(17) . . ?
O4 N5 O3 123.56(19) . . ?
O4 N5 C1 115.75(16) . . ?
N1 C1 C2 105.09(18) . . ?
N5 C1 N1 125.92(17) . . ?
N5 C1 C2 128.98(19) . . ?
N4 C2 C1 144.9(2) . . ?
N4 C2 C3 110.58(19) . . ?
C1 C2 C3 104.53(17) . . ?
N2 C3 C2 113.12(17) . . ?
N3 C3 N2 136.2(2) . . ?
N3 C3 C2 110.66(18) . . ?
C4 N6 N7 100.55(16) . . ?
C5 N7 N6 137.56(18) . . ?
C5 N7 C6 108.00(17) . . ?
C6 N7 N6 114.43(16) . . ?
N9 N8 H8 118.0(18) . . ?
C5 N8 N9 113.93(16) . . ?
C5 N8 H8 128.1(18) . . ?
C6 N9 N8 100.40(16) . . ?
N12 N10 C4 129.09(16) . . ?
C6 N10 N12 124.52(17) . . ?
C6 N10 C4 105.64(17) . . ?
C5 N11 H11A 121.0(19) . . ?
C5 N11 H11B 120.4(19) . . ?
H11A N11 H11B 118(3) . . ?
N10 N12 H12A 107.1(17) . . ?
N10 N12 H12B 107.1(18) . . ?
H12A N12 H12B 115(2) . . ?
C4 N13 H13A 116.5(15) . . ?
C4 N13 H13B 122.8(17) . . ?
H13A N13 H13B 120(2) . . ?
N6 C4 N10 114.28(16) . . ?
N6 C4 N13 125.05(19) . . ?
N13 C4 N10 120.63(19) . . ?
N8 C5 N7 103.69(18) . . ?
N11 C5 N7 126.64(19) . . ?
N11 C5 N8 129.67(19) . . ?
N7 C6 N10 105.07(17) . . ?
N9 C6 N7 113.96(18) . . ?
N9 C6 N10 140.9(2) . . ?
H1SA O1S H1SB 110(3) . . ?

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
N8 H8 O1 0.84(2) 2.05(3) 2.701(2) 134(2) .
N8 H8 O3 0.84(2) 2.13(2) 2.827(2) 141(2) .
N11 H11A O1 0.87(3) 2.39(3) 2.998(2) 128(2) .
N11 H11B O1S 0.85(3) 1.97(3) 2.816(3) 172(3) .
N12 H12B O1S 0.90(3) 2.05(3) 2.882(3) 153(2) 7_566
N13 H13A N3 0.90(3) 2.20(3) 3.089(3) 169(2) 6_556
N13 H13B N4 0.88(3) 2.15(3) 3.015(3) 170(2) 4_466
O1S H1SA O3 0.83(4) 2.53(3) 3.038(2) 120(3) 8_655
O1S H1SA N9 0.83(4) 2.17(4) 2.952(3) 156(3) 8_655
O1S H1SB N2 0.86(4) 2.23(4) 3.063(2) 163(4) 2_565


_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'Tang 79'
_olex2_submission_special_instructions 'No special instructions were received'
