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

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1nptpv
_database_code_depnum_ccdc_archive 'CCDC 1540318'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2017-12-21 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 H3 N9 O4, C2 H3 N'
_chemical_formula_sum            'C6 H6 N10 O4'
_chemical_formula_weight         282.21

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.5053(5)
_cell_length_b                   10.4920(13)
_cell_length_c                   12.3817(17)
_cell_angle_alpha                83.323(4)
_cell_angle_beta                 82.161(5)
_cell_angle_gamma                85.293(4)
_cell_volume                     574.57(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      24.42

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5499
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2092
_reflns_number_gt                1241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.2649P] 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         2092
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.4382(7) 0.4326(3) 0.7324(3) 0.0224(8) Uani 1 1 d . . . . .
C2 C 0.5933(7) 0.3631(3) 0.8120(3) 0.0191(8) Uani 1 1 d . . . . .
C3 C 0.8497(6) 0.0327(3) 0.8709(3) 0.0177(8) Uani 1 1 d . . . . .
C4 C 0.7532(7) 0.2359(3) 0.8162(2) 0.0180(8) Uani 1 1 d . . . . .
C5 C 0.7233(8) 0.8918(4) 0.6174(3) 0.0333(10) Uani 1 1 d . . . . .
C6 C 0.9323(9) 0.7922(5) 0.5719(4) 0.0680(16) Uani 1 1 d . . . . .
H6A H 1.0408 0.8275 0.5023 0.102 Uiso 1 1 calc R U . . .
H6B H 0.8206 0.7201 0.5593 0.102 Uiso 1 1 calc R U . . .
H6C H 1.0758 0.7619 0.6236 0.102 Uiso 1 1 calc R U . . .
N1 N 0.5532(6) 0.4283(2) 0.8998(2) 0.0279(7) Uani 1 1 d . . . . .
N2 N 0.3825(7) 0.5318(3) 0.8681(3) 0.0317(8) Uani 1 1 d . . . . .
H2 H 0.325(7) 0.589(3) 0.913(3) 0.038 Uiso 1 1 d . U . . .
N3 N 0.3049(6) 0.5394(3) 0.7692(2) 0.0304(8) Uani 1 1 d . . . . .
N4 N 0.3989(6) 0.4005(3) 0.6254(2) 0.0293(7) Uani 1 1 d . . . . .
N5 N 0.9925(5) 0.2017(2) 0.7522(2) 0.0215(7) Uani 1 1 d . . . . .
N6 N 1.0519(6) 0.0736(2) 0.7887(2) 0.0203(7) Uani 1 1 d . . . . .
H6 H 1.205(7) 0.034(3) 0.753(3) 0.024 Uiso 1 1 d . U . . .
N7 N 0.6580(6) 0.1358(2) 0.8901(2) 0.0179(7) Uani 1 1 d . . . . .
H7 H 0.504(7) 0.135(3) 0.941(3) 0.022 Uiso 1 1 d . U . . .
N8 N 0.8035(5) -0.0796(2) 0.9343(2) 0.0202(7) Uani 1 1 d . . . . .
N9 N 1.0029(6) -0.1781(3) 0.9110(2) 0.0257(7) Uani 1 1 d . . . . .
N10 N 0.5645(7) 0.9690(3) 0.6529(3) 0.0418(9) Uani 1 1 d . . . . .
O1 O 0.2109(6) 0.4652(3) 0.5767(2) 0.0476(8) Uani 1 1 d . . . . .
O2 O 0.5520(5) 0.3081(2) 0.59274(19) 0.0352(7) Uani 1 1 d . . . . .
O3 O 1.2164(5) -0.1670(2) 0.8375(2) 0.0362(7) Uani 1 1 d . . . . .
O4 O 0.9580(5) -0.2802(2) 0.97105(19) 0.0318(6) 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
C1 N3 1.326(4) . ?
C1 C2 1.389(4) . ?
C1 N4 1.441(4) . ?
C2 N1 1.334(4) . ?
C2 C4 1.463(4) . ?
C3 N6 1.327(4) . ?
C3 N7 1.350(4) . ?
C3 N8 1.352(4) . ?
C4 N5 1.299(4) . ?
C4 N7 1.367(4) . ?
C5 N10 1.125(4) . ?
C5 C6 1.458(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N1 N2 1.330(3) . ?
N2 N3 1.310(4) . ?
N2 H2 0.87(3) . ?
N4 O2 1.218(3) . ?
N4 O1 1.222(3) . ?
N5 N6 1.384(3) . ?
N6 H6 0.87(3) . ?
N7 H7 0.87(3) . ?
N8 N9 1.343(3) . ?
N9 O3 1.234(3) . ?
N9 O4 1.246(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
N3 C1 C2 110.1(3) . . ?
N3 C1 N4 120.4(3) . . ?
C2 C1 N4 129.4(3) . . ?
N1 C2 C1 107.6(3) . . ?
N1 C2 C4 120.4(3) . . ?
C1 C2 C4 131.7(3) . . ?
N6 C3 N7 105.6(3) . . ?
N6 C3 N8 135.7(3) . . ?
N7 C3 N8 118.7(3) . . ?
N5 C4 N7 111.5(3) . . ?
N5 C4 C2 126.3(3) . . ?
N7 C4 C2 122.1(3) . . ?
N10 C5 C6 179.3(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 N1 C2 103.0(3) . . ?
N3 N2 N1 116.9(3) . . ?
N3 N2 H2 123(2) . . ?
N1 N2 H2 120(2) . . ?
N2 N3 C1 102.4(3) . . ?
O2 N4 O1 125.6(3) . . ?
O2 N4 C1 116.6(3) . . ?
O1 N4 C1 117.8(3) . . ?
C4 N5 N6 103.8(2) . . ?
C3 N6 N5 111.8(2) . . ?
C3 N6 H6 131(2) . . ?
N5 N6 H6 117(2) . . ?
C3 N7 C4 107.2(3) . . ?
C3 N7 H7 124.5(19) . . ?
C4 N7 H7 128.2(19) . . ?
N9 N8 C3 115.6(2) . . ?
O3 N9 O4 123.0(3) . . ?
O3 N9 N8 122.5(3) . . ?
O4 N9 N8 114.5(3) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.063

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1559066'
_audit_update_record             
;
2017-06-28 deposited with the CCDC.
2017-12-21 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 H2 N8 O4'
_chemical_formula_sum            'C4 H2 N8 O4'
_chemical_formula_weight         226.14

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   12.9567(12)
_cell_length_b                   6.4248(8)
_cell_length_c                   9.6417(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     802.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1763
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      24.15

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6931
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7638
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.144
_diffrn_reflns_theta_max         26.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1569
_reflns_number_gt                1151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.944

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.3937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1569
_refine_ls_number_parameters     151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.5920(4) 0.3900(8) 0.5838(5) 0.0146(12) Uani 1 1 d . . . . .
C2 C 0.6760(4) 0.4994(8) 0.6386(5) 0.0158(12) Uani 1 1 d . . . . .
C3 C 0.8253(4) 0.9491(7) 0.6185(5) 0.0132(12) Uani 1 1 d . . . . .
C4 C 0.7299(4) 0.6917(8) 0.6049(5) 0.0132(12) Uani 1 1 d . . . . .
N1 N 0.7069(3) 0.3937(6) 0.7520(5) 0.0176(9) Uani 1 1 d . . . . .
N2 N 0.6427(3) 0.2339(7) 0.7580(5) 0.0196(11) Uani 1 1 d . . . . .
H2 H 0.642(4) 0.151(8) 0.823(6) 0.024 Uiso 1 1 d . U . . .
N3 N 0.5716(3) 0.2215(7) 0.6591(4) 0.0189(11) Uani 1 1 d . . . . .
N4 N 0.5287(3) 0.4400(7) 0.4664(5) 0.0181(10) Uani 1 1 d . . . . .
N5 N 0.7316(3) 0.7915(6) 0.4828(4) 0.0152(10) Uani 1 1 d . . . . .
H5 H 0.704(4) 0.766(8) 0.406(6) 0.018 Uiso 1 1 d . U . . .
N6 N 0.7935(3) 0.9603(6) 0.4904(5) 0.0156(10) Uani 1 1 d . . . . .
N7 N 0.7890(3) 0.7909(6) 0.6956(4) 0.0131(10) Uani 1 1 d . . . . .
N8 N 0.8962(3) 1.1010(7) 0.6761(5) 0.0222(11) Uani 1 1 d . . . . .
O1 O 0.4441(3) 0.3566(6) 0.4558(4) 0.0254(10) Uani 1 1 d . . . . .
O2 O 0.5642(3) 0.5668(6) 0.3835(4) 0.0239(9) Uani 1 1 d . . . . .
O3 O 0.9335(4) 1.2265(6) 0.5963(5) 0.0387(12) Uani 1 1 d . . . . .
O4 O 0.9146(3) 1.0887(6) 0.8004(4) 0.0281(10) 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
C1 N3 1.330(6) . ?
C1 C2 1.400(7) . ?
C1 N4 1.435(7) . ?
C2 N1 1.347(6) . ?
C2 C4 1.456(7) . ?
C3 N6 1.304(6) . ?
C3 N7 1.344(6) . ?
C3 N8 1.451(6) . ?
C4 N7 1.326(6) . ?
C4 N5 1.341(7) . ?
N1 N2 1.323(6) . ?
N2 N3 1.329(6) . ?
N2 H2 0.82(5) . ?
N4 O1 1.223(5) . ?
N4 O2 1.231(5) . ?
N5 N6 1.351(5) . ?
N5 H5 0.84(5) . ?
N8 O3 1.215(6) . ?
N8 O4 1.224(5) . ?

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 C1 C2 111.0(5) . . ?
N3 C1 N4 120.0(4) . . ?
C2 C1 N4 129.1(4) . . ?
N1 C2 C1 106.5(4) . . ?
N1 C2 C4 117.8(4) . . ?
C1 C2 C4 135.6(5) . . ?
N6 C3 N7 117.1(4) . . ?
N6 C3 N8 121.7(4) . . ?
N7 C3 N8 121.2(4) . . ?
N7 C4 N5 109.9(4) . . ?
N7 C4 C2 122.5(4) . . ?
N5 C4 C2 127.6(4) . . ?
N2 N1 C2 103.9(4) . . ?
N1 N2 N3 116.8(4) . . ?
N1 N2 H2 123(4) . . ?
N3 N2 H2 120(4) . . ?
N2 N3 C1 101.8(4) . . ?
O1 N4 O2 124.8(4) . . ?
O1 N4 C1 118.7(4) . . ?
O2 N4 C1 116.5(4) . . ?
C4 N5 N6 110.2(4) . . ?
C4 N5 H5 132(4) . . ?
N6 N5 H5 117(4) . . ?
C3 N6 N5 101.2(4) . . ?
C4 N7 C3 101.5(4) . . ?
O3 N8 O4 125.8(5) . . ?
O3 N8 C3 117.1(5) . . ?
O4 N8 C3 117.0(4) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.071

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

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1572217'
_audit_update_record             
;
2017-09-02 deposited with the CCDC.
2017-12-21 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         '2(C H6 N3), C4 H N9 O4'
_chemical_formula_sum            'C6 H13 N15 O4'
_chemical_formula_weight         359.31

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   45.902(5)
_cell_length_b                   3.5862(4)
_cell_length_c                   8.3346(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1372.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2963
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      21.70


_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13773
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.021
_diffrn_reflns_theta_max         26.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2603
_reflns_number_gt                1643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.850
_reflns_Friedel_fraction_full    0.913

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.4572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 537 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2603
_refine_ls_number_parameters     265
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.91168(12) 1.0934(15) 1.2269(7) 0.0135(14) Uani 1 1 d . . . . .
C2 C 0.91078(12) 1.0225(15) 1.0638(7) 0.0159(15) Uani 1 1 d . . . . .
C3 C 0.84604(12) 0.8717(16) 0.8426(7) 0.0144(14) Uani 1 1 d . . . . .
C4 C 0.88728(12) 0.9231(16) 0.9524(7) 0.0156(14) Uani 1 1 d . . . . .
C5 C 0.78924(12) 0.3448(16) 0.2065(7) 0.0139(15) Uani 1 1 d . . . . .
C6 C 0.96847(12) 0.6946(15) 0.6191(7) 0.0145(14) Uani 1 1 d . . . . .
N1 N 0.93833(10) 1.0785(13) 1.0114(6) 0.0196(13) Uani 1 1 d . . . . .
N2 N 0.95468(10) 1.1824(14) 1.1392(6) 0.0251(14) Uani 1 1 d . . . . .
N3 N 0.93850(10) 1.1958(14) 1.2730(5) 0.0210(13) Uani 1 1 d . . . . .
N4 N 0.88912(11) 1.0586(14) 1.3461(6) 0.0199(13) Uani 1 1 d . . . . .
N5 N 0.89333(10) 0.7623(14) 0.8148(6) 0.0186(12) Uani 1 1 d . . . . .
N6 N 0.86653(10) 0.7328(15) 0.7453(6) 0.0170(13) Uani 1 1 d . . . . .
H6A H 0.8628(11) 0.619(15) 0.657(7) 0.020 Uiso 1 1 d . U . . .
N7 N 0.85843(10) 0.9996(13) 0.9772(6) 0.0148(11) Uani 1 1 d . . . . .
N8 N 0.81632(10) 0.9077(13) 0.8234(6) 0.0183(12) Uani 1 1 d . . . . .
N9 N 0.80552(11) 0.7808(13) 0.6880(6) 0.0203(13) Uani 1 1 d . . . . .
N10 N 0.77275(10) 0.4733(14) 0.3254(6) 0.0204(12) Uani 1 1 d D . . . .
H10A H 0.7806(9) 0.578(15) 0.415(5) 0.024 Uiso 1 1 d D U . . .
H10B H 0.7536(6) 0.518(13) 0.302(6) 0.024 Uiso 1 1 d D U . . .
N11 N 0.77723(10) 0.2200(13) 0.0744(6) 0.0191(12) Uani 1 1 d D . . . .
H11A H 0.7582(5) 0.162(13) 0.077(6) 0.023 Uiso 1 1 d D U . . .
H11B H 0.7891(8) 0.122(14) -0.002(5) 0.023 Uiso 1 1 d D U . . .
N12 N 0.81781(10) 0.3460(15) 0.2246(6) 0.0240(13) Uani 1 1 d D . . . .
H12A H 0.8295(9) 0.259(15) 0.143(4) 0.029 Uiso 1 1 d D U . . .
H12B H 0.8263(10) 0.456(15) 0.310(4) 0.029 Uiso 1 1 d D U . . .
N13 N 0.97810(10) 0.8659(14) 0.7482(6) 0.0188(12) Uani 1 1 d D . . . .
H13A H 0.9651(8) 0.954(14) 0.818(5) 0.023 Uiso 1 1 d D U . . .
H13B H 0.9968(6) 0.932(16) 0.748(7) 0.023 Uiso 1 1 d D U . . .
N14 N 0.98721(10) 0.6131(14) 0.5010(6) 0.0228(13) Uani 1 1 d D . . . .
H14A H 1.0061(7) 0.649(14) 0.524(7) 0.027 Uiso 1 1 d D U . . .
H14B H 0.9811(10) 0.447(14) 0.429(6) 0.027 Uiso 1 1 d D U . . .
N15 N 0.94109(11) 0.5990(16) 0.6063(6) 0.0224(14) Uani 1 1 d D . . . .
H15A H 0.9363(10) 0.466(14) 0.520(4) 0.027 Uiso 1 1 d D U . . .
H15B H 0.9293(10) 0.645(16) 0.689(4) 0.027 Uiso 1 1 d D U . . .
O1 O 0.89244(9) 1.2215(12) 1.4733(5) 0.0308(11) Uani 1 1 d . . . . .
O2 O 0.86834(9) 0.8615(12) 1.3140(5) 0.0288(11) Uani 1 1 d . . . . .
O3 O 0.77809(8) 0.8120(11) 0.6709(5) 0.0266(11) Uani 1 1 d . . . . .
O4 O 0.82047(8) 0.6323(12) 0.5788(4) 0.0268(11) 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
C1 N3 1.341(7) . ?
C1 C2 1.383(7) . ?
C1 N4 1.441(7) . ?
C2 N1 1.353(6) . ?
C2 C4 1.467(8) . ?
C3 N7 1.339(7) . ?
C3 N6 1.338(7) . ?
C3 N8 1.380(6) . ?
C4 N5 1.314(7) . ?
C4 N7 1.368(6) . ?
C5 N11 1.310(7) . ?
C5 N12 1.320(7) . ?
C5 N10 1.329(7) . ?
C6 N15 1.307(7) . ?
C6 N13 1.315(7) . ?
C6 N14 1.339(7) . ?
N1 N2 1.355(6) . ?
N2 N3 1.341(6) . ?
N4 O2 1.217(6) . ?
N4 O1 1.220(6) . ?
N5 N6 1.364(6) . ?
N6 H6A 0.86(6) . ?
N8 N9 1.314(6) . ?
N9 O4 1.258(6) . ?
N9 O3 1.272(5) . ?
N10 H10A 0.91(2) . ?
N10 H10B 0.92(2) . ?
N11 H11A 0.90(2) . ?
N11 H11B 0.91(2) . ?
N12 H12A 0.92(2) . ?
N12 H12B 0.90(2) . ?
N13 H13A 0.89(2) . ?
N13 H13B 0.89(2) . ?
N14 H14A 0.90(2) . ?
N14 H14B 0.89(3) . ?
N15 H15A 0.89(2) . ?
N15 H15B 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 111.1(5) . . ?
N3 C1 N4 119.1(5) . . ?
C2 C1 N4 129.8(5) . . ?
N1 C2 C1 105.2(5) . . ?
N1 C2 C4 121.3(5) . . ?
C1 C2 C4 133.5(5) . . ?
N7 C3 N6 109.7(5) . . ?
N7 C3 N8 119.0(5) . . ?
N6 C3 N8 131.3(5) . . ?
N5 C4 N7 115.1(5) . . ?
N5 C4 C2 120.2(5) . . ?
N7 C4 C2 124.6(5) . . ?
N11 C5 N12 121.0(5) . . ?
N11 C5 N10 120.4(5) . . ?
N12 C5 N10 118.7(5) . . ?
N15 C6 N13 120.8(5) . . ?
N15 C6 N14 120.0(5) . . ?
N13 C6 N14 119.2(5) . . ?
C2 N1 N2 107.8(5) . . ?
N3 N2 N1 110.9(4) . . ?
N2 N3 C1 105.1(4) . . ?
O2 N4 O1 124.5(5) . . ?
O2 N4 C1 117.5(5) . . ?
O1 N4 C1 117.9(5) . . ?
C4 N5 N6 102.4(4) . . ?
C3 N6 N5 110.4(5) . . ?
C3 N6 H6A 124(4) . . ?
N5 N6 H6A 125(4) . . ?
C3 N7 C4 102.4(5) . . ?
N9 N8 C3 116.1(5) . . ?
O4 N9 O3 119.7(5) . . ?
O4 N9 N8 124.2(5) . . ?
O3 N9 N8 116.0(5) . . ?
C5 N10 H10A 122(3) . . ?
C5 N10 H10B 116(3) . . ?
H10A N10 H10B 119(4) . . ?
C5 N11 H11A 118(3) . . ?
C5 N11 H11B 118(3) . . ?
H11A N11 H11B 121(4) . . ?
C5 N12 H12A 120(3) . . ?
C5 N12 H12B 121(3) . . ?
H12A N12 H12B 119(4) . . ?
C6 N13 H13A 118(3) . . ?
C6 N13 H13B 117(3) . . ?
H13A N13 H13B 123(4) . . ?
C6 N14 H14A 116(4) . . ?
C6 N14 H14B 116(3) . . ?
H14A N14 H14B 123(4) . . ?
C6 N15 H15A 116(3) . . ?
C6 N15 H15B 118(3) . . ?
H15A N15 H15B 125(4) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.074

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

data_1_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc1nv5l8
_database_code_depnum_ccdc_archive 'CCDC 1544500'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-12-21 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         'C H6 N3, C4 H2 N9 O4'
_chemical_formula_sum            'C5 H8 N12 O4'
_chemical_formula_weight         300.23

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

_space_group_crystal_system      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                   15.6882(15)
_cell_length_b                   4.8817(5)
_cell_length_c                   16.3623(17)
_cell_angle_alpha                90
_cell_angle_beta                 118.492(4)
_cell_angle_gamma                90
_cell_volume                     1101.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1327
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.00

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6054
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6723
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1933
_reflns_number_gt                1264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1933
_refine_ls_number_parameters     214
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.13712(18) 0.6686(5) 0.57184(19) 0.0166(6) Uani 1 1 d . . . . .
C2 C 0.27669(18) 0.5677(5) 0.58020(19) 0.0156(6) Uani 1 1 d . . . . .
C3 C 0.45886(17) 0.7251(5) 0.66695(19) 0.0178(6) Uani 1 1 d . . . . .
C4 C 0.37948(18) 0.5709(5) 0.60682(19) 0.0167(6) Uani 1 1 d . . . . .
C5 C 0.27319(19) -0.1531(6) 0.3789(2) 0.0195(6) Uani 1 1 d . . . . .
N1 N 0.21456(14) 0.4000(5) 0.51797(16) 0.0209(6) Uani 1 1 d . . . . .
N2 N 0.12756(15) 0.4697(5) 0.51355(17) 0.0203(6) Uani 1 1 d . . . . .
H2A H 0.074(2) 0.387(6) 0.477(2) 0.024 Uiso 1 1 d . U . . .
N3 N 0.23209(15) 0.7356(5) 0.61458(17) 0.0172(5) Uani 1 1 d . . . . .
H3A H 0.256(2) 0.856(6) 0.657(2) 0.021 Uiso 1 1 d . U . . .
N4 N 0.05922(15) 0.7653(5) 0.57723(16) 0.0197(5) Uani 1 1 d . . . . .
N5 N 0.07412(15) 0.9777(4) 0.63419(16) 0.0201(5) Uani 1 1 d . . . . .
N6 N 0.41321(15) 0.3823(4) 0.56888(16) 0.0204(6) Uani 1 1 d . . . . .
N7 N 0.50921(15) 0.4264(5) 0.60502(17) 0.0250(6) Uani 1 1 d . . . . .
N8 N 0.53870(15) 0.6323(5) 0.66522(17) 0.0234(6) Uani 1 1 d . . . . .
N9 N 0.46739(16) 0.9511(5) 0.72592(16) 0.0212(5) Uani 1 1 d . . . . .
N10 N 0.36245(16) -0.0656(5) 0.43155(18) 0.0236(6) Uani 1 1 d D . . . .
H10A H 0.4103(17) -0.154(5) 0.429(2) 0.028 Uiso 1 1 d D U . . .
H10B H 0.3729(19) 0.072(5) 0.4700(18) 0.028 Uiso 1 1 d D U . . .
N11 N 0.19957(16) -0.0300(5) 0.38172(19) 0.0277(6) Uani 1 1 d D . . . .
H11A H 0.1409(14) -0.086(6) 0.3463(18) 0.033 Uiso 1 1 d D U . . .
H11B H 0.209(2) 0.109(5) 0.4197(19) 0.033 Uiso 1 1 d D U . . .
N12 N 0.25696(17) -0.3630(5) 0.32177(18) 0.0259(6) Uani 1 1 d D . . . .
H12A H 0.1981(14) -0.429(6) 0.2898(19) 0.031 Uiso 1 1 d D U . . .
H12B H 0.3047(16) -0.456(5) 0.322(2) 0.031 Uiso 1 1 d D U . . .
O1 O 0.00001(13) 1.0687(4) 0.63338(14) 0.0263(5) Uani 1 1 d . . . . .
O2 O 0.15614(13) 1.0760(4) 0.68394(14) 0.0280(5) Uani 1 1 d . . . . .
O3 O 0.39294(13) 1.0502(4) 0.72145(14) 0.0234(5) Uani 1 1 d . . . . .
O4 O 0.54952(13) 1.0392(4) 0.77891(14) 0.0283(5) 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
C1 N2 1.319(3) . ?
C1 N3 1.350(3) . ?
C1 N4 1.352(3) . ?
C2 N1 1.308(3) . ?
C2 N3 1.362(3) . ?
C2 C4 1.456(3) . ?
C3 N8 1.345(3) . ?
C3 C4 1.384(4) . ?
C3 N9 1.429(3) . ?
C4 N6 1.352(3) . ?
C5 N10 1.317(3) . ?
C5 N11 1.322(3) . ?
C5 N12 1.327(4) . ?
N1 N2 1.375(3) . ?
N2 H2A 0.86(3) . ?
N3 H3A 0.84(3) . ?
N4 N5 1.338(3) . ?
N5 O1 1.239(3) . ?
N5 O2 1.245(3) . ?
N6 N7 1.347(3) . ?
N7 N8 1.326(3) . ?
N9 O3 1.234(3) . ?
N9 O4 1.237(3) . ?
N10 H10A 0.879(16) . ?
N10 H10B 0.881(17) . ?
N11 H11A 0.865(17) . ?
N11 H11B 0.883(17) . ?
N12 H12A 0.878(17) . ?
N12 H12B 0.878(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 105.7(2) . . ?
N2 C1 N4 120.7(2) . . ?
N3 C1 N4 133.7(3) . . ?
N1 C2 N3 111.1(2) . . ?
N1 C2 C4 123.2(2) . . ?
N3 C2 C4 125.7(2) . . ?
N8 C3 C4 109.5(2) . . ?
N8 C3 N9 119.1(2) . . ?
C4 C3 N9 131.5(2) . . ?
N6 C4 C3 106.3(2) . . ?
N6 C4 C2 118.4(2) . . ?
C3 C4 C2 135.3(2) . . ?
N10 C5 N11 120.3(3) . . ?
N10 C5 N12 119.9(2) . . ?
N11 C5 N12 119.9(3) . . ?
C2 N1 N2 103.8(2) . . ?
C1 N2 N1 112.1(2) . . ?
C1 N2 H2A 125.1(18) . . ?
N1 N2 H2A 122.8(18) . . ?
C1 N3 C2 107.3(2) . . ?
C1 N3 H3A 122.6(19) . . ?
C2 N3 H3A 130.0(19) . . ?
N5 N4 C1 116.9(2) . . ?
O1 N5 O2 122.7(2) . . ?
O1 N5 N4 114.8(2) . . ?
O2 N5 N4 122.5(2) . . ?
N7 N6 C4 106.9(2) . . ?
N8 N7 N6 111.6(2) . . ?
N7 N8 C3 105.8(2) . . ?
O3 N9 O4 123.0(2) . . ?
O3 N9 C3 118.8(2) . . ?
O4 N9 C3 118.2(2) . . ?
C5 N10 H10A 118.5(19) . . ?
C5 N10 H10B 119.5(18) . . ?
H10A N10 H10B 122(3) . . ?
C5 N11 H11A 120(2) . . ?
C5 N11 H11B 121.2(19) . . ?
H11A N11 H11B 119(3) . . ?
C5 N12 H12A 119.9(19) . . ?
C5 N12 H12B 121.7(19) . . ?
H12A N12 H12B 118(3) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.069

