# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_mo_dm16684_0m
_database_code_depnum_ccdc_archive 'CCDC 1524819'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H11 N10, C2 H N4 O3'
_chemical_formula_sum            'C8 H12 N14 O3'
_chemical_formula_weight         352.32
_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 0.0033 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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   12.8678(14)
_cell_length_b                   6.4849(7)
_cell_length_c                   33.243(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.281(2)
_cell_angle_gamma                90
_cell_volume                     2766.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3701
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.300
_cell_measurement_theta_min      3.18
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.8786.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            13235
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.470
_diffrn_reflns_theta_min         2.458
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3402
_reflns_number_total             4191
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+3.6571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          ?
_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
N1 N 0.39834(12) 0.8025(2) 0.57991(4) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.35162(12) 0.7754(2) 0.54108(4) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.42373(10) 1.0843(2) 0.54542(4) 0.0161(3) Uani 1 1 d . . . . .
N4 N 0.45171(13) 1.2805(2) 0.53236(4) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.4160(18) 1.378(4) 0.5464(7) 0.026(6) Uiso 1 1 d . . . . .
H4B H 0.520(2) 1.298(4) 0.5383(8) 0.043(7) Uiso 1 1 d . . . . .
N5 N 0.33940(12) 0.9858(3) 0.48176(4) 0.0223(3) Uani 1 1 d . . . . .
H5A H 0.2812(19) 0.923(4) 0.4731(7) 0.028(6) Uiso 1 1 d . . . . .
H5B H 0.3432(19) 1.113(4) 0.4737(7) 0.033(6) Uiso 1 1 d . . . . .
N6 N 0.62371(10) 1.1746(2) 0.74227(4) 0.0147(3) Uani 1 1 d . . . . .
H6 H 0.6355(18) 1.272(4) 0.7580(7) 0.031(6) Uiso 1 1 d . . . . .
N7 N 0.58294(11) 1.2027(2) 0.70283(4) 0.0156(3) Uani 1 1 d . . . . .
N8 N 0.59461(10) 0.8702(2) 0.71853(4) 0.0128(2) Uani 1 1 d . . . . .
N9 N 0.59084(11) 0.6539(2) 0.71704(4) 0.0161(3) Uani 1 1 d . . . . .
H9A H 0.6283(18) 0.615(4) 0.6975(7) 0.025(6) Uiso 1 1 d . . . . .
H9B H 0.5232(18) 0.610(3) 0.7098(7) 0.024(5) Uiso 1 1 d . . . . .
N10 N 0.66435(11) 0.8906(2) 0.78683(4) 0.0160(3) Uani 1 1 d . . . . .
H10A H 0.6640(18) 0.761(4) 0.7891(7) 0.028(6) Uiso 1 1 d . . . . .
H10B H 0.6877(19) 0.974(4) 0.8060(7) 0.035(6) Uiso 1 1 d . . . . .
C1 C 0.36827(13) 0.9480(3) 0.52099(5) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.44130(12) 0.9868(3) 0.58216(4) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.49513(12) 1.0725(2) 0.61810(5) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.5119(18) 1.217(4) 0.6188(7) 0.032(6) Uiso 1 1 d . . . . .
C4 C 0.52182(12) 0.9503(2) 0.64973(4) 0.0154(3) Uani 1 1 d . . . . .
H4 H 0.5091(16) 0.807(3) 0.6470(6) 0.019(5) Uiso 1 1 d . . . . .
C5 C 0.56648(11) 1.0156(2) 0.68883(4) 0.0136(3) Uani 1 1 d . . . . .
C6 C 0.63105(11) 0.9749(2) 0.75200(4) 0.0126(3) Uani 1 1 d . . . . .
O1 O 0.85268(10) 0.97072(19) 0.69698(3) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.65687(12) 0.5603(2) 0.56186(4) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.66735(16) 0.3945(3) 0.61885(5) 0.0535(5) Uani 1 1 d . . . . .
N11 N 0.82190(12) 0.9859(2) 0.62648(4) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.847(2) 1.107(4) 0.6188(8) 0.040(7) Uiso 1 1 d . . . . .
N12 N 0.77348(11) 0.8676(2) 0.59662(4) 0.0189(3) Uani 1 1 d . . . . .
N13 N 0.76152(10) 0.7166(2) 0.65814(4) 0.0160(3) Uani 1 1 d . . . . .
N14 N 0.68380(13) 0.5457(3) 0.59795(5) 0.0269(3) Uani 1 1 d . . . . .
C7 C 0.81500(13) 0.8970(2) 0.66377(5) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.74095(12) 0.7141(2) 0.61778(5) 0.0168(3) 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 N2 1.3941(18) . ?
N1 C2 1.317(2) . ?
N2 C1 1.329(2) . ?
N3 N4 1.4003(19) . ?
N3 C1 1.365(2) . ?
N3 C2 1.3786(19) . ?
N4 H4A 0.93(2) . ?
N4 H4B 0.90(3) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.87(3) . ?
N5 C1 1.352(2) . ?
N6 H6 0.83(3) . ?
N6 N7 1.3875(17) . ?
N6 C6 1.337(2) . ?
N7 C5 1.311(2) . ?
N8 N9 1.4041(18) . ?
N8 C5 1.3935(19) . ?
N8 C6 1.3568(18) . ?
N9 H9A 0.87(2) . ?
N9 H9B 0.93(2) . ?
N10 H10A 0.84(3) . ?
N10 H10B 0.87(3) . ?
N10 C6 1.3226(19) . ?
C2 C3 1.447(2) . ?
C3 H3 0.96(3) . ?
C3 C4 1.340(2) . ?
C4 H4 0.94(2) . ?
C4 C5 1.445(2) . ?
O1 C7 1.2661(19) . ?
O2 N14 1.2275(19) . ?
O3 N14 1.229(2) . ?
N11 H11 0.89(3) . ?
N11 N12 1.3669(19) . ?
N11 C7 1.376(2) . ?
N12 C8 1.306(2) . ?
N13 C7 1.363(2) . ?
N13 C8 1.3483(19) . ?
N14 C8 1.447(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
C2 N1 N2 108.49(13) . . ?
C1 N2 N1 106.53(13) . . ?
C1 N3 N4 122.61(13) . . ?
C1 N3 C2 105.93(13) . . ?
C2 N3 N4 131.46(13) . . ?
N3 N4 H4A 108.3(14) . . ?
N3 N4 H4B 108.4(18) . . ?
H4A N4 H4B 109(2) . . ?
H5A N5 H5B 114(2) . . ?
C1 N5 H5A 113.3(15) . . ?
C1 N5 H5B 116.8(16) . . ?
N7 N6 H6 122.4(17) . . ?
C6 N6 H6 125.5(17) . . ?
C6 N6 N7 111.77(12) . . ?
C5 N7 N6 104.69(12) . . ?
C5 N8 N9 130.12(12) . . ?
C6 N8 N9 122.54(12) . . ?
C6 N8 C5 107.34(13) . . ?
N8 N9 H9A 107.0(16) . . ?
N8 N9 H9B 110.1(14) . . ?
H9A N9 H9B 106(2) . . ?
H10A N10 H10B 124(2) . . ?
C6 N10 H10A 119.0(16) . . ?
C6 N10 H10B 117.0(18) . . ?
N2 C1 N3 110.06(13) . . ?
N2 C1 N5 126.46(15) . . ?
N5 C1 N3 123.43(15) . . ?
N1 C2 N3 108.99(13) . . ?
N1 C2 C3 124.64(14) . . ?
N3 C2 C3 126.34(14) . . ?
C2 C3 H3 119.1(14) . . ?
C4 C3 C2 119.99(15) . . ?
C4 C3 H3 120.9(14) . . ?
C3 C4 H4 118.2(13) . . ?
C3 C4 C5 126.42(15) . . ?
C5 C4 H4 115.3(13) . . ?
N7 C5 N8 110.38(13) . . ?
N7 C5 C4 129.30(14) . . ?
N8 C5 C4 120.26(13) . . ?
N6 C6 N8 105.82(13) . . ?
N10 C6 N6 128.67(14) . . ?
N10 C6 N8 125.50(14) . . ?
N12 N11 H11 116.2(17) . . ?
N12 N11 C7 111.27(13) . . ?
C7 N11 H11 132.4(17) . . ?
C8 N12 N11 100.59(12) . . ?
C8 N13 C7 101.91(13) . . ?
O2 N14 O3 124.48(17) . . ?
O2 N14 C8 118.94(15) . . ?
O3 N14 C8 116.57(15) . . ?
O1 C7 N11 125.56(15) . . ?
O1 C7 N13 126.88(14) . . ?
N13 C7 N11 107.56(13) . . ?
N12 C8 N13 118.67(14) . . ?
N12 C8 N14 120.16(14) . . ?
N13 C8 N14 121.17(14) . . ?

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 H6 O1 0.83(3) 1.97(3) 2.7866(18) 168(2) 4_656
N10 H10A O1 0.84(3) 1.96(3) 2.7875(19) 169(2) 4_646
N11 H11 N1 0.89(3) 1.96(3) 2.794(2) 155(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 N2 C1 N3 0.01(19) . . . . ?
N1 N2 C1 N5 177.56(17) . . . . ?
N1 C2 C3 C4 13.0(3) . . . . ?
N2 N1 C2 N3 0.24(19) . . . . ?
N2 N1 C2 C3 178.50(15) . . . . ?
N3 C2 C3 C4 -169.02(16) . . . . ?
N4 N3 C1 N2 -179.33(15) . . . . ?
N4 N3 C1 N5 3.0(3) . . . . ?
N4 N3 C2 N1 179.16(16) . . . . ?
N4 N3 C2 C3 0.9(3) . . . . ?
N6 N7 C5 N8 0.71(16) . . . . ?
N6 N7 C5 C4 177.93(15) . . . . ?
N7 N6 C6 N8 -0.01(17) . . . . ?
N7 N6 C6 N10 -178.74(15) . . . . ?
N9 N8 C5 N7 -179.71(15) . . . . ?
N9 N8 C5 C4 2.8(2) . . . . ?
N9 N8 C6 N6 179.50(13) . . . . ?
N9 N8 C6 N10 -1.7(2) . . . . ?
C1 N3 C2 N1 -0.23(18) . . . . ?
C1 N3 C2 C3 -178.45(15) . . . . ?
C2 N1 N2 C1 -0.16(19) . . . . ?
C2 N3 C1 N2 0.13(19) . . . . ?
C2 N3 C1 N5 -177.51(16) . . . . ?
C2 C3 C4 C5 -173.66(14) . . . . ?
C3 C4 C5 N7 5.7(3) . . . . ?
C3 C4 C5 N8 -177.27(15) . . . . ?
C5 N8 C6 N6 0.44(16) . . . . ?
C5 N8 C6 N10 179.22(14) . . . . ?
C6 N6 N7 C5 -0.44(17) . . . . ?
C6 N8 C5 N7 -0.75(17) . . . . ?
C6 N8 C5 C4 -178.26(13) . . . . ?
O2 N14 C8 N12 -7.8(3) . . . . ?
O2 N14 C8 N13 172.06(16) . . . . ?
O3 N14 C8 N12 170.91(19) . . . . ?
O3 N14 C8 N13 -9.2(3) . . . . ?
N11 N12 C8 N13 0.3(2) . . . . ?
N11 N12 C8 N14 -179.83(15) . . . . ?
N12 N11 C7 O1 179.83(15) . . . . ?
N12 N11 C7 N13 0.35(19) . . . . ?
C7 N11 N12 C8 -0.39(18) . . . . ?
C7 N13 C8 N12 -0.1(2) . . . . ?
C7 N13 C8 N14 -179.97(15) . . . . ?
C8 N13 C7 O1 -179.61(16) . . . . ?
C8 N13 C7 N11 -0.14(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_dm16714
_database_code_depnum_ccdc_archive 'CCDC 1524817'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 N10, 2(C3 H N4 O4), 1.5(H4 O2)'
_chemical_formula_sum            'C12 H20 N18 O11'
_chemical_formula_weight         592.46
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.413(2)
_cell_length_b                   10.1729(13)
_cell_length_c                   10.5386(13)
_cell_angle_alpha                117.773(2)
_cell_angle_beta                 100.209(3)
_cell_angle_gamma                97.012(3)
_cell_volume                     581.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3123
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.67
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0558 before and 0.0279 after correction.
The Ratio of minimum to maximum transmission is 0.8157.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.668
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3017
_reflns_number_total             3566
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O5-H5BB
 0.85 with sigma of 0.02
 O6-H6A
 0.85 with sigma of 0.02
3. Others
 Fixed Sof: O6(0.5) H5BB(0.5) H6A(0.5) H6B(0.5) H5C(0.5)
4.a Free rotating group:
 O5(H5AA)
;
_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
N1 N 0.67271(15) 0.27508(11) 0.58408(10) 0.01963(19) Uani 1 1 d . . . . .
H1 H 0.552(3) 0.267(2) 0.526(2) 0.039(5) Uiso 1 1 d . . . . .
N2 N 0.71556(15) 0.37488(11) 0.73557(9) 0.01868(19) Uani 1 1 d . . . . .
N3 N 1.00653(14) 0.29048(10) 0.67602(9) 0.01467(17) Uani 1 1 d . . . . .
N4 N 1.21351(15) 0.25913(12) 0.68232(10) 0.02056(19) Uani 1 1 d . . . . .
H4A H 1.233(3) 0.229(2) 0.7512(19) 0.037(5) Uiso 1 1 d . . . . .
H4B H 1.308(3) 0.345(2) 0.711(2) 0.042(5) Uiso 1 1 d . . . . .
N5 N 0.86865(17) 0.12782(12) 0.41473(10) 0.0227(2) Uani 1 1 d . . . . .
H5A H 0.757(3) 0.080(2) 0.3381(19) 0.037(5) Uiso 1 1 d . . . . .
H5B H 0.995(3) 0.106(2) 0.4100(19) 0.034(4) Uiso 1 1 d . . . . .
C1 C 0.84694(16) 0.22349(12) 0.54721(11) 0.01623(19) Uani 1 1 d . . . . .
C2 C 0.91900(16) 0.38122(11) 0.78940(10) 0.01410(18) Uani 1 1 d . . . . .
C3 C 1.04606(16) 0.46959(11) 0.94361(10) 0.01473(19) Uani 1 1 d . . . . .
H3 H 1.206(3) 0.4853(17) 0.9650(16) 0.024(4) Uiso 1 1 d . . . . .
O1 O 0.54887(14) 0.35547(11) 0.20256(10) 0.0301(2) Uani 1 1 d . . . . .
O2 O 0.49899(14) 0.31187(11) -0.02460(11) 0.0307(2) Uani 1 1 d . . . . .
O3 O -0.29007(14) -0.00648(10) -0.32633(9) 0.02569(19) Uani 1 1 d . . . . .
O4 O -0.46719(13) -0.01220(11) -0.16975(10) 0.02663(19) Uani 1 1 d . . . . .
N6 N 0.11739(15) 0.23430(11) 0.14811(10) 0.02033(19) Uani 1 1 d . . . . .
N7 N 0.08488(14) 0.15465(10) -0.09983(10) 0.01684(18) Uani 1 1 d . . . . .
N8 N 0.43395(15) 0.30230(11) 0.07494(11) 0.0213(2) Uani 1 1 d . . . . .
N9 N -0.29847(15) 0.02633(10) -0.19882(10) 0.01811(18) Uani 1 1 d . . . . .
C4 C 0.20896(17) 0.22649(12) 0.03962(11) 0.0176(2) Uani 1 1 d . . . . .
C5 C -0.10871(16) 0.11193(12) -0.07786(11) 0.01605(19) Uani 1 1 d . . . . .
C6 C -0.09227(18) 0.15959(13) 0.07181(12) 0.0192(2) Uani 1 1 d . . . . .
H6 H -0.200(3) 0.1464(18) 0.1177(17) 0.026(4) Uiso 1 1 d . . . . .
O5 O 0.34214(15) 0.36776(11) 0.45445(10) 0.0272(2) Uani 1 1 d D . . . .
H5AA H 0.290924 0.323700 0.358381 0.041 Uiso 1 1 d G . . . .
O6 O 0.0394(4) 0.5210(3) 0.5599(3) 0.0373(4) Uani 0.5 1 d D . P A 2
H5BB H 0.242(4) 0.415(3) 0.484(3) 0.020(7) Uiso 0.5 1 d D . P B 1
H6A H -0.088(3) 0.530(3) 0.527(3) 0.019(7) Uiso 0.5 1 d D . P C 2
H6B H 0.099(8) 0.600(5) 0.653(5) 0.065(13) Uiso 0.5 1 d . . P D 2
H5C H 0.446(8) 0.457(5) 0.494(5) 0.060(13) Uiso 0.5 1 d . . P E 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
N1 H1 0.866(19) . ?
N1 N2 1.3860(12) . ?
N1 C1 1.3349(14) . ?
N2 C2 1.3081(14) . ?
N3 N4 1.4000(13) . ?
N3 C1 1.3527(12) . ?
N3 C2 1.3897(13) . ?
N4 H4A 0.903(18) . ?
N4 H4B 0.89(2) . ?
N5 H5A 0.863(18) . ?
N5 H5B 0.870(19) . ?
N5 C1 1.3234(13) . ?
C2 C3 1.4504(13) . ?
C3 C3 1.3406(19) 2_767 ?
C3 H3 0.989(16) . ?
O1 N8 1.2321(12) . ?
O2 N8 1.2345(14) . ?
O3 N9 1.2378(12) . ?
O4 N9 1.2426(13) . ?
N6 C4 1.3503(14) . ?
N6 C6 1.3527(14) . ?
N7 C4 1.3303(13) . ?
N7 C5 1.3594(14) . ?
N8 C4 1.4442(14) . ?
N9 C5 1.4217(13) . ?
C5 C6 1.3963(14) . ?
C6 H6 0.939(16) . ?
O5 H5AA 0.8701 . ?
O5 H5BB 0.865(18) . ?
O5 H5C 0.92(4) . ?
O6 O6 1.118(5) 2_566 ?
O6 H6A 0.865(18) . ?
O6 H6B 0.90(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
N2 N1 H1 118.5(12) . . ?
C1 N1 H1 128.6(12) . . ?
C1 N1 N2 111.89(9) . . ?
C2 N2 N1 104.46(9) . . ?
C1 N3 N4 122.23(8) . . ?
C1 N3 C2 107.42(9) . . ?
C2 N3 N4 130.25(8) . . ?
N3 N4 H4A 104.3(11) . . ?
N3 N4 H4B 107.3(13) . . ?
H4A N4 H4B 111.9(16) . . ?
H5A N5 H5B 121.1(16) . . ?
C1 N5 H5A 120.8(12) . . ?
C1 N5 H5B 117.6(11) . . ?
N1 C1 N3 105.68(9) . . ?
N5 C1 N1 129.30(10) . . ?
N5 C1 N3 125.01(10) . . ?
N2 C2 N3 110.53(9) . . ?
N2 C2 C3 127.28(9) . . ?
N3 C2 C3 122.19(9) . . ?
C2 C3 H3 118.1(9) . . ?
C3 C3 C2 122.40(12) 2_767 . ?
C3 C3 H3 119.5(9) 2_767 . ?
C4 N6 C6 102.39(9) . . ?
C4 N7 C5 99.64(9) . . ?
O1 N8 O2 123.80(10) . . ?
O1 N8 C4 118.42(10) . . ?
O2 N8 C4 117.78(9) . . ?
O3 N9 O4 123.06(9) . . ?
O3 N9 C5 119.74(9) . . ?
O4 N9 C5 117.20(9) . . ?
N6 C4 N8 120.77(9) . . ?
N7 C4 N6 118.74(9) . . ?
N7 C4 N8 120.39(9) . . ?
N7 C5 N9 121.26(9) . . ?
N7 C5 C6 112.05(9) . . ?
C6 C5 N9 126.68(10) . . ?
N6 C6 C5 107.19(10) . . ?
N6 C6 H6 123.0(9) . . ?
C5 C6 H6 129.8(9) . . ?
H5AA O5 H5BB 100.9 . . ?
H5AA O5 H5C 113.0 . . ?
O6 O6 H6A 55(2) 2_566 . ?
O6 O6 H6B 149(3) 2_566 . ?
H6A O6 H6B 109(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
N1 H1 O5 0.866(19) 2.033(19) 2.8127(14) 149.5(17) .
O5 H5AA N6 0.87 1.99 2.8516(13) 168.2 .
O6 H6A O5 0.865(18) 2.03(2) 2.828(3) 154(3) 2_566
O5 H5C O5 0.92(4) 1.88(4) 2.799(2) 172(4) 2_666

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 N2 C2 N3 1.02(12) . . . . ?
N1 N2 C2 C3 -179.85(10) . . . . ?
N2 N1 C1 N3 -0.15(12) . . . . ?
N2 N1 C1 N5 -179.81(11) . . . . ?
N2 C2 C3 C3 15.7(2) . . . 2_767 ?
N3 C2 C3 C3 -165.32(12) . . . 2_767 ?
N4 N3 C1 N1 177.58(10) . . . . ?
N4 N3 C1 N5 -2.73(16) . . . . ?
N4 N3 C2 N2 -177.64(10) . . . . ?
N4 N3 C2 C3 3.18(16) . . . . ?
C1 N1 N2 C2 -0.55(12) . . . . ?
C1 N3 C2 N2 -1.16(12) . . . . ?
C1 N3 C2 C3 179.66(9) . . . . ?
C2 N3 C1 N1 0.75(11) . . . . ?
C2 N3 C1 N5 -179.56(10) . . . . ?
O1 N8 C4 N6 10.22(16) . . . . ?
O1 N8 C4 N7 -173.48(10) . . . . ?
O2 N8 C4 N6 -168.76(10) . . . . ?
O2 N8 C4 N7 7.54(16) . . . . ?
O3 N9 C5 N7 -2.16(15) . . . . ?
O3 N9 C5 C6 179.06(10) . . . . ?
O4 N9 C5 N7 177.82(10) . . . . ?
O4 N9 C5 C6 -0.96(16) . . . . ?
N7 C5 C6 N6 -0.28(13) . . . . ?
N9 C5 C6 N6 178.59(10) . . . . ?
C4 N6 C6 C5 0.35(12) . . . . ?
C4 N7 C5 N9 -178.87(10) . . . . ?
C4 N7 C5 C6 0.07(12) . . . . ?
C5 N7 C4 N6 0.19(12) . . . . ?
C5 N7 C4 N8 -176.19(9) . . . . ?
C6 N6 C4 N7 -0.36(13) . . . . ?
C6 N6 C4 N8 176.00(10) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_dm16712
_database_code_depnum_ccdc_archive 'CCDC 1524813'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 N10, 2(Cl O4)'
_chemical_formula_sum            'C6 H12 Cl2 N10 O8'
_chemical_formula_weight         423.16
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z+1/2'
'-x+1/2, y, -z'
'y+3/4, x+1/4, -z+1/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1'
'-x+1, y+1/2, -z+1/2'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z-1/2'
'x-1/2, -y, z'
'-y-3/4, -x-1/4, z-1/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-y-1/4, -x+1/4, z+1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   12.2856(7)
_cell_length_b                   12.2856(7)
_cell_length_c                   40.490(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6111.4(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5027
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.358
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9224.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            28870
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.660
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1920
_reflns_number_total             2368
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+7.1737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
N1 N -0.12818(10) 0.70822(10) 0.08843(3) 0.0128(2) Uani 1 1 d . . . . .
H1 H -0.0824(18) 0.6654(18) 0.0940(5) 0.028(6) Uiso 1 1 d . . . . .
N2 N -0.18611(10) 0.76460(10) 0.11232(3) 0.0138(2) Uani 1 1 d . . . . .
N3 N -0.24937(10) 0.79883(10) 0.06229(3) 0.0112(2) Uani 1 1 d . . . . .
N4 N -0.31164(10) 0.83496(10) 0.03549(3) 0.0132(2) Uani 1 1 d . . . . .
H4A H -0.2942(16) 0.9037(17) 0.0310(5) 0.023(5) Uiso 1 1 d . . . . .
H4B H -0.3812(19) 0.8268(17) 0.0405(5) 0.028(6) Uiso 1 1 d . . . . .
N5 N -0.13132(12) 0.69309(12) 0.02927(3) 0.0174(3) Uani 1 1 d . . . . .
H5A H -0.1545(18) 0.7225(18) 0.0121(5) 0.031(6) Uiso 1 1 d . . . . .
H5B H -0.0864(19) 0.6451(19) 0.0289(6) 0.032(6) Uiso 1 1 d . . . . .
C1 C -0.16618(11) 0.72847(11) 0.05814(3) 0.0118(3) Uani 1 1 d . . . . .
C2 C -0.25878(12) 0.81989(11) 0.09588(3) 0.0124(3) Uani 1 1 d . . . . .
C3 C -0.33911(12) 0.89544(12) 0.10888(3) 0.0139(3) Uani 1 1 d . . . . .
H3 H -0.3794(17) 0.9371(17) 0.0932(5) 0.021(5) Uiso 1 1 d . . . . .
Cl1 Cl 0.09442(3) 0.46682(3) 0.04750(2) 0.01536(10) Uani 1 1 d . . . . .
O1 O 0.01164(11) 0.53892(10) 0.06025(3) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.12943(13) 0.50754(13) 0.01602(3) 0.0371(4) Uani 1 1 d . . . . .
O3 O 0.04920(10) 0.35946(10) 0.04353(4) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.18461(11) 0.46301(11) 0.06991(4) 0.0339(3) 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 H1 0.80(2) . ?
N1 N2 1.3864(16) . ?
N1 C1 1.3359(18) . ?
N2 C2 1.3047(18) . ?
N3 N4 1.3998(16) . ?
N3 C1 1.3491(18) . ?
N3 C2 1.3892(17) . ?
N4 H4A 0.89(2) . ?
N4 H4B 0.88(2) . ?
N5 H5A 0.83(2) . ?
N5 H5B 0.81(2) . ?
N5 C1 1.3184(18) . ?
C2 C3 1.4536(19) . ?
C3 C3 1.332(3) 7_365 ?
C3 H3 0.95(2) . ?
Cl1 O1 1.4441(12) . ?
Cl1 O2 1.4350(13) . ?
Cl1 O3 1.4402(12) . ?
Cl1 O4 1.4329(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 119.5(16) . . ?
C1 N1 H1 128.6(16) . . ?
C1 N1 N2 111.61(12) . . ?
C2 N2 N1 104.79(12) . . ?
C1 N3 N4 121.38(11) . . ?
C1 N3 C2 107.72(11) . . ?
C2 N3 N4 130.86(12) . . ?
N3 N4 H4A 109.2(13) . . ?
N3 N4 H4B 108.3(14) . . ?
H4A N4 H4B 112.8(18) . . ?
H5A N5 H5B 122(2) . . ?
C1 N5 H5A 119.0(15) . . ?
C1 N5 H5B 118.6(17) . . ?
N1 C1 N3 105.65(12) . . ?
N5 C1 N1 129.73(14) . . ?
N5 C1 N3 124.59(13) . . ?
N2 C2 N3 110.23(12) . . ?
N2 C2 C3 127.74(13) . . ?
N3 C2 C3 122.02(12) . . ?
C2 C3 H3 117.0(12) . . ?
C3 C3 C2 122.86(17) 7_365 . ?
C3 C3 H3 120.1(12) 7_365 . ?
O2 Cl1 O1 108.34(9) . . ?
O2 Cl1 O3 109.62(9) . . ?
O3 Cl1 O1 109.27(8) . . ?
O4 Cl1 O1 109.77(8) . . ?
O4 Cl1 O2 110.00(9) . . ?
O4 Cl1 O3 109.82(8) . . ?

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 N2 C2 N3 0.83(15) . . . . ?
N1 N2 C2 C3 -178.10(14) . . . . ?
N2 N1 C1 N3 0.15(16) . . . . ?
N2 N1 C1 N5 177.96(15) . . . . ?
N2 C2 C3 C3 -6.08(19) . . . 7_365 ?
N3 C2 C3 C3 175.10(9) . . . 7_365 ?
N4 N3 C1 N1 -177.52(12) . . . . ?
N4 N3 C1 N5 4.5(2) . . . . ?
N4 N3 C2 N2 176.82(13) . . . . ?
N4 N3 C2 C3 -4.2(2) . . . . ?
C1 N1 N2 C2 -0.63(16) . . . . ?
C1 N3 C2 N2 -0.78(16) . . . . ?
C1 N3 C2 C3 178.23(13) . . . . ?
C2 N3 C1 N1 0.36(15) . . . . ?
C2 N3 C1 N5 -177.59(14) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_1
_database_code_depnum_ccdc_archive 'CCDC 1524818'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N10, 2(C3 N5 O6)'
_chemical_formula_sum            'C12 H12 N20 O12'
_chemical_formula_weight         628.42

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2/n  '
_symmetry_space_group_name_Hall  '-P 2yac'

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

_cell_length_a                   13.4466(13)
_cell_length_b                   5.9301(6)
_cell_length_c                   15.0419(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.917(4)
_cell_angle_gamma                90.00
_cell_volume                     1188.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1168
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      24.54

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6516
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2150
_reflns_number_gt                1403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49613(16) 0.9101(4) 0.47311(14) 0.0175(6) Uani 1 1 d . . .
H1 H 0.4683 0.7755 0.4934 0.021 Uiso 1 1 calc R . .
C2 C 0.54790(16) 0.7875(4) 0.25080(15) 0.0150(5) Uani 1 1 d . . .
C3 C 0.52820(16) 0.9111(4) 0.38552(14) 0.0151(5) Uani 1 1 d . . .
C4 C 0.14292(17) 1.0130(4) 0.48052(15) 0.0188(5) Uani 1 1 d . . .
C5 C 0.19968(16) 0.8286(4) 0.46521(14) 0.0160(5) Uani 1 1 d . . .
C6 C 0.21595(17) 0.7287(4) 0.54951(15) 0.0183(6) Uani 1 1 d . . .
N1 N 0.57909(14) 1.0681(3) 0.35125(12) 0.0172(5) Uani 1 1 d . . .
N2 N 0.59192(15) 0.9865(3) 0.26732(12) 0.0182(5) Uani 1 1 d . . .
H2A H 0.6274(16) 1.054(4) 0.2314(15) 0.022 Uiso 1 1 d . . .
N3 N 0.50749(14) 0.7359(3) 0.32538(12) 0.0150(4) Uani 1 1 d . . .
N4 N 0.54361(16) 0.6625(4) 0.17810(14) 0.0235(5) Uani 1 1 d . . .
H4A H 0.5072(19) 0.545(4) 0.1738(16) 0.028 Uiso 1 1 d . . .
H4B H 0.5667(18) 0.727(4) 0.1337(17) 0.028 Uiso 1 1 d . . .
N5 N 0.45637(16) 0.5374(3) 0.34235(14) 0.0233(5) Uani 1 1 d D . .
H5A H 0.4980(16) 0.426(3) 0.3389(16) 0.028 Uiso 1 1 d D . .
H5B H 0.3958(13) 0.533(4) 0.3079(14) 0.028 Uiso 1 1 d D . .
N6 N 0.17150(15) 0.8466(3) 0.60939(13) 0.0226(5) Uani 1 1 d . . .
N7 N 0.12537(14) 1.0235(3) 0.56576(13) 0.0241(5) Uani 1 1 d . . .
N8 N 0.09708(15) 1.1798(4) 0.41814(15) 0.0262(5) Uani 1 1 d . . .
N9 N 0.23627(15) 0.7644(4) 0.38226(13) 0.0217(5) Uani 1 1 d . . .
N10 N 0.27573(14) 0.5342(3) 0.57703(14) 0.0252(5) Uani 1 1 d . . .
O1 O 0.05872(14) 1.3447(3) 0.44936(13) 0.0400(5) Uani 1 1 d . . .
O2 O 0.09907(13) 1.1467(3) 0.33772(11) 0.0334(5) Uani 1 1 d . . .
O3 O 0.29547(13) 0.8911(3) 0.35392(11) 0.0316(5) Uani 1 1 d . . .
O4 O 0.20497(14) 0.5882(3) 0.34644(11) 0.0352(5) Uani 1 1 d . . .
O5 O 0.32282(14) 0.4515(3) 0.52068(12) 0.0380(5) Uani 1 1 d . . .
O6 O 0.27768(14) 0.4652(3) 0.65336(12) 0.0396(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 C1 1.333(4) 3_676 ?
C1 C3 1.442(3) . ?
C1 H1 0.9500 . ?
C2 N4 1.316(3) . ?
C2 N2 1.329(3) . ?
C2 N3 1.347(3) . ?
C3 N1 1.303(3) . ?
C3 N3 1.380(3) . ?
C4 N7 1.337(3) . ?
C4 C5 1.371(3) . ?
C4 N8 1.442(3) . ?
C5 C6 1.389(3) . ?
C5 N9 1.454(3) . ?
C6 N6 1.344(3) . ?
C6 N10 1.434(3) . ?
N1 N2 1.385(2) . ?
N2 H2A 0.87(2) . ?
N3 N5 1.404(3) . ?
N4 H4A 0.85(3) . ?
N4 H4B 0.86(3) . ?
N5 H5A 0.871(16) . ?
N5 H5B 0.903(16) . ?
N6 N7 1.343(3) . ?
N8 O2 1.229(2) . ?
N8 O1 1.229(2) . ?
N9 O3 1.214(2) . ?
N9 O4 1.223(2) . ?
N10 O6 1.216(2) . ?
N10 O5 1.228(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C3 122.9(3) 3_676 . ?
C1 C1 H1 118.6 3_676 . ?
C3 C1 H1 118.6 . . ?
N4 C2 N2 128.6(2) . . ?
N4 C2 N3 126.0(2) . . ?
N2 C2 N3 105.44(19) . . ?
N1 C3 N3 110.37(18) . . ?
N1 C3 C1 127.1(2) . . ?
N3 C3 C1 122.5(2) . . ?
N7 C4 C5 112.0(2) . . ?
N7 C4 N8 118.4(2) . . ?
C5 C4 N8 129.5(2) . . ?
C4 C5 C6 102.00(19) . . ?
C4 C5 N9 128.0(2) . . ?
C6 C5 N9 130.0(2) . . ?
N6 C6 C5 111.2(2) . . ?
N6 C6 N10 120.5(2) . . ?
C5 C6 N10 128.2(2) . . ?
C3 N1 N2 104.42(17) . . ?
C2 N2 N1 111.89(18) . . ?
C2 N2 H2A 124.2(16) . . ?
N1 N2 H2A 123.8(16) . . ?
C2 N3 C3 107.86(18) . . ?
C2 N3 N5 127.25(18) . . ?
C3 N3 N5 124.84(18) . . ?
C2 N4 H4A 118.9(16) . . ?
C2 N4 H4B 114.5(17) . . ?
H4A N4 H4B 125(2) . . ?
N3 N5 H5A 106.9(16) . . ?
N3 N5 H5B 110.2(16) . . ?
H5A N5 H5B 119(2) . . ?
C6 N6 N7 107.27(18) . . ?
C4 N7 N6 107.57(19) . . ?
O2 N8 O1 124.8(2) . . ?
O2 N8 C4 117.8(2) . . ?
O1 N8 C4 117.5(2) . . ?
O3 N9 O4 125.2(2) . . ?
O3 N9 C5 117.1(2) . . ?
O4 N9 C5 117.7(2) . . ?
O6 N10 O5 124.9(2) . . ?
O6 N10 C6 118.8(2) . . ?
O5 N10 C6 116.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1524814'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N10, O4 S'
_chemical_formula_sum            'C6 H12 N10 O4 S'
_chemical_formula_weight         320.32

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   6.4108(6)
_cell_length_b                   13.4566(14)
_cell_length_c                   14.2343(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.654(3)
_cell_angle_gamma                90.00
_cell_volume                     1213.98(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6913
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.33
_reflns_number_total             2187
_reflns_number_gt                1542
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.2235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     220
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8640(4) 0.08357(18) 0.18986(17) 0.0142(6) Uani 1 1 d . . .
H1 H 0.7180 0.0726 0.1691 0.017 Uiso 1 1 calc R . .
C2 C 0.9933(4) 0.09588(18) 0.12564(17) 0.0144(6) Uani 1 1 d . . .
H2 H 1.1410 0.0989 0.1466 0.017 Uiso 1 1 calc R . .
C3 C 0.9369(4) 0.11562(18) 0.44203(17) 0.0139(6) Uani 1 1 d . . .
C4 C 0.9420(4) 0.08669(18) 0.29056(18) 0.0125(6) Uani 1 1 d . . .
C5 C 0.9248(4) 0.14037(18) -0.12536(18) 0.0129(6) Uani 1 1 d . . .
C6 C 0.9163(4) 0.10480(17) 0.02520(17) 0.0122(6) Uani 1 1 d . . .
N1 N 1.1376(3) 0.08257(16) 0.32999(14) 0.0167(5) Uani 1 1 d . . .
N2 N 1.1336(4) 0.10083(16) 0.42511(15) 0.0172(5) Uani 1 1 d D . .
H2A H 1.246(3) 0.100(2) 0.4680(16) 0.021 Uiso 1 1 d D . .
N3 N 0.8116(3) 0.10624(15) 0.35789(14) 0.0125(5) Uani 1 1 d . . .
N4 N 0.8753(4) 0.13687(19) 0.52421(16) 0.0218(6) Uani 1 1 d D . .
H4A H 0.968(4) 0.159(2) 0.5697(16) 0.026 Uiso 1 1 d D . .
H4B H 0.745(3) 0.136(2) 0.528(2) 0.026 Uiso 1 1 d D . .
N5 N 0.5932(3) 0.12471(17) 0.34789(16) 0.0168(5) Uani 1 1 d D . .
H5A H 0.523(4) 0.0698(16) 0.3332(18) 0.020 Uiso 1 1 d D . .
H5B H 0.560(4) 0.1650(18) 0.2976(16) 0.020 Uiso 1 1 d D . .
N6 N 0.7224(3) 0.09509(16) -0.01675(14) 0.0154(5) Uani 1 1 d . . .
N7 N 0.7297(4) 0.11780(16) -0.11147(15) 0.0154(5) Uani 1 1 d D . .
H7A H 0.618(3) 0.113(2) -0.1567(15) 0.018 Uiso 1 1 d D . .
N8 N 1.0475(3) 0.13179(15) -0.04009(14) 0.0125(5) Uani 1 1 d . . .
N9 N 0.9881(4) 0.16701(17) -0.20556(16) 0.0192(5) Uani 1 1 d D . .
H9A H 0.893(4) 0.181(2) -0.2536(16) 0.023 Uiso 1 1 d D . .
H9B H 1.122(3) 0.169(2) -0.209(2) 0.023 Uiso 1 1 d D . .
N10 N 1.2662(4) 0.14989(19) -0.02843(17) 0.0192(5) Uani 1 1 d D . .
H10A H 1.332(4) 0.0931(15) -0.0132(19) 0.023 Uiso 1 1 d D . .
H10B H 1.294(4) 0.1922(18) 0.0199(16) 0.023 Uiso 1 1 d D . .
O1 O 0.4580(3) 0.41057(13) 0.07937(12) 0.0205(4) Uani 1 1 d . . .
O2 O 0.4108(3) 0.40623(13) 0.24444(12) 0.0201(5) Uani 1 1 d . . .
O3 O 0.6127(3) 0.27783(13) 0.18132(13) 0.0206(5) Uani 1 1 d . . .
O4 O 0.2355(3) 0.28615(13) 0.13449(13) 0.0205(5) Uani 1 1 d . . .
S1 S 0.43027(10) 0.34494(5) 0.15960(5) 0.01361(18) 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 C2 1.333(3) . ?
C1 C4 1.446(3) . ?
C1 H1 0.9500 . ?
C2 C6 1.446(3) . ?
C2 H2 0.9500 . ?
C3 N4 1.321(3) . ?
C3 N2 1.334(3) . ?
C3 N3 1.344(3) . ?
C4 N1 1.296(3) . ?
C4 N3 1.388(3) . ?
C5 N9 1.318(3) . ?
C5 N7 1.330(3) . ?
C5 N8 1.348(3) . ?
C6 N6 1.302(3) . ?
C6 N8 1.392(3) . ?
N1 N2 1.380(3) . ?
N2 H2A 0.873(17) . ?
N3 N5 1.408(3) . ?
N4 H4A 0.860(18) . ?
N4 H4B 0.844(17) . ?
N5 H5A 0.873(18) . ?
N5 H5B 0.898(18) . ?
N6 N7 1.390(3) . ?
N7 H7A 0.888(17) . ?
N8 N10 1.408(3) . ?
N9 H9A 0.865(18) . ?
N9 H9B 0.867(17) . ?
N10 H10A 0.883(18) . ?
N10 H10B 0.890(18) . ?
O1 S1 1.4755(18) . ?
O2 S1 1.4831(18) . ?
O3 S1 1.4730(18) . ?
O4 S1 1.4760(19) . ?

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 C1 C4 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C4 C1 H1 119.4 . . ?
C1 C2 C6 122.2(2) . . ?
C1 C2 H2 118.9 . . ?
C6 C2 H2 118.9 . . ?
N4 C3 N2 127.5(3) . . ?
N4 C3 N3 126.2(2) . . ?
N2 C3 N3 106.2(2) . . ?
N1 C4 N3 110.7(2) . . ?
N1 C4 C1 126.6(2) . . ?
N3 C4 C1 122.4(2) . . ?
N9 C5 N7 127.6(3) . . ?
N9 C5 N8 126.1(2) . . ?
N7 C5 N8 106.3(2) . . ?
N6 C6 N8 110.5(2) . . ?
N6 C6 C2 127.3(2) . . ?
N8 C6 C2 122.1(2) . . ?
C4 N1 N2 104.9(2) . . ?
C3 N2 N1 111.2(2) . . ?
C3 N2 H2A 125.6(18) . . ?
N1 N2 H2A 123.1(18) . . ?
C3 N3 C4 107.0(2) . . ?
C3 N3 N5 121.7(2) . . ?
C4 N3 N5 131.0(2) . . ?
C3 N4 H4A 118.4(19) . . ?
C3 N4 H4B 119(2) . . ?
H4A N4 H4B 122(3) . . ?
N3 N5 H5A 109.9(18) . . ?
N3 N5 H5B 107.6(17) . . ?
H5A N5 H5B 106(3) . . ?
C6 N6 N7 104.67(19) . . ?
C5 N7 N6 111.4(2) . . ?
C5 N7 H7A 125.4(17) . . ?
N6 N7 H7A 123.1(17) . . ?
C5 N8 C6 107.1(2) . . ?
C5 N8 N10 121.8(2) . . ?
C6 N8 N10 131.1(2) . . ?
C5 N9 H9A 118.0(19) . . ?
C5 N9 H9B 120(2) . . ?
H9A N9 H9B 122(3) . . ?
N8 N10 H10A 107.9(18) . . ?
N8 N10 H10B 106.2(18) . . ?
H10A N10 H10B 109(3) . . ?
O3 S1 O1 110.18(11) . . ?
O3 S1 O4 109.76(11) . . ?
O1 S1 O4 109.25(11) . . ?
O3 S1 O2 109.35(11) . . ?
O1 S1 O2 109.40(10) . . ?
O4 S1 O2 108.88(11) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_mo_dm16683_0m
_database_code_depnum_ccdc_archive 'CCDC 1524820'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 N10, C2 N10, 2(H2 O)'
_chemical_formula_sum            'C8 H16 N20 O2'
_chemical_formula_weight         424.41
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.755(2)
_cell_length_b                   8.863(4)
_cell_length_c                   9.154(4)
_cell_angle_alpha                77.761(7)
_cell_angle_beta                 80.303(7)
_cell_angle_gamma                78.757(7)
_cell_volume                     443.6(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1077
_cell_measurement_temperature    130
_cell_measurement_theta_max      27.756
_cell_measurement_theta_min      2.297
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.7924.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3481
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.199
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1349
_reflns_number_total             2092
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_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
N6 N 0.3151(3) 0.65881(19) 0.54674(19) 0.0266(4) Uani 1 1 d . . . . .
N7 N 0.4943(3) 0.7485(2) 0.4846(2) 0.0259(4) Uani 1 1 d . . . . .
H7 H 0.559(6) 0.778(3) 0.548(4) 0.061(9) Uiso 1 1 d . . . . .
N8 N 0.3686(3) 0.69241(18) 0.29663(18) 0.0221(4) Uani 1 1 d . . . . .
N9 N 0.3299(4) 0.6848(2) 0.1512(2) 0.0305(4) Uani 1 1 d . . . . .
H9A H 0.476(5) 0.641(3) 0.107(3) 0.044(7) Uiso 1 1 d . . . . .
H9B H 0.278(6) 0.781(4) 0.104(4) 0.075(10) Uiso 1 1 d . . . . .
N10 N 0.6864(3) 0.8436(2) 0.2388(2) 0.0281(4) Uani 1 1 d . . . . .
H10A H 0.702(5) 0.838(3) 0.147(3) 0.049(8) Uiso 1 1 d . . . . .
H10B H 0.776(5) 0.894(3) 0.267(3) 0.052(8) Uiso 1 1 d . . . . .
C2 C 0.5297(3) 0.7680(2) 0.3348(2) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.2414(4) 0.6262(2) 0.4304(2) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.0584(4) 0.5323(2) 0.4346(2) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.030(4) 0.515(3) 0.340(3) 0.032(6) Uiso 1 1 d . . . . .
N1 N 0.0982(3) 1.0533(2) 0.17432(19) 0.0297(4) Uani 1 1 d . . . . .
N2 N 0.2537(3) 1.1402(2) 0.0837(2) 0.0312(4) Uani 1 1 d . . . . .
N3 N 0.3621(3) 1.2058(2) 0.16507(19) 0.0294(4) Uani 1 1 d . . . . .
N4 N 0.2798(3) 1.1634(2) 0.31240(19) 0.0268(4) Uani 1 1 d . . . . .
N5 N -0.0204(3) 0.99102(19) 0.43675(18) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.1197(4) 1.0705(2) 0.3132(2) 0.0243(4) Uani 1 1 d . . . . .
O1 O 0.7939(4) 0.4746(3) 0.1183(2) 0.0576(6) Uani 1 1 d . . . . .
H1A H 0.756(7) 0.387(4) 0.176(4) 0.079(13) Uiso 1 1 d . . . . .
H1B H 0.876(13) 0.434(8) 0.040(9) 0.25(4) 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
N6 N7 1.396(3) . ?
N6 C3 1.315(3) . ?
N7 H7 0.85(3) . ?
N7 C2 1.331(3) . ?
N8 N9 1.404(2) . ?
N8 C2 1.371(3) . ?
N8 C3 1.393(2) . ?
N9 H9A 0.92(3) . ?
N9 H9B 0.89(3) . ?
N10 H10A 0.84(3) . ?
N10 H10B 0.84(3) . ?
N10 C2 1.324(3) . ?
C3 C4 1.456(3) . ?
C4 C4 1.342(4) 2_566 ?
C4 H4 0.95(2) . ?
N1 N2 1.353(3) . ?
N1 C1 1.340(3) . ?
N2 N3 1.328(3) . ?
N3 N4 1.351(2) . ?
N4 C1 1.347(3) . ?
N5 N5 1.267(3) 2_576 ?
N5 C1 1.415(3) . ?
O1 H1A 0.88(4) . ?
O1 H1B 0.89(8) . ?

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
C3 N6 N7 104.95(16) . . ?
N6 N7 H7 115(2) . . ?
C2 N7 N6 111.62(17) . . ?
C2 N7 H7 133(2) . . ?
C2 N8 N9 127.56(17) . . ?
C2 N8 C3 107.26(16) . . ?
C3 N8 N9 125.15(17) . . ?
N8 N9 H9A 104.5(16) . . ?
N8 N9 H9B 109(2) . . ?
H9A N9 H9B 114(3) . . ?
H10A N10 H10B 118(3) . . ?
C2 N10 H10A 119.0(19) . . ?
C2 N10 H10B 123(2) . . ?
N7 C2 N8 105.92(18) . . ?
N10 C2 N7 128.48(19) . . ?
N10 C2 N8 125.61(19) . . ?
N6 C3 N8 110.23(18) . . ?
N6 C3 C4 126.78(19) . . ?
N8 C3 C4 122.97(19) . . ?
C3 C4 H4 117.1(14) . . ?
C4 C4 C3 121.6(3) 2_566 . ?
C4 C4 H4 121.3(14) 2_566 . ?
C1 N1 N2 103.58(17) . . ?
N3 N2 N1 110.43(17) . . ?
N2 N3 N4 108.88(18) . . ?
C1 N4 N3 104.41(16) . . ?
N5 N5 C1 113.1(2) 2_576 . ?
N1 C1 N4 112.70(18) . . ?
N1 C1 N5 117.87(19) . . ?
N4 C1 N5 129.43(19) . . ?
H1A O1 H1B 99(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
N7 H7 N4 0.85(3) 1.90(3) 2.753(3) 177(3) 2_676
N10 H10A N2 0.84(3) 2.06(3) 2.890(3) 171(3) 2_675

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
N6 N7 C2 N8 1.1(2) . . . . ?
N6 N7 C2 N10 -178.86(18) . . . . ?
N6 C3 C4 C4 0.4(4) . . . 2_566 ?
N7 N6 C3 N8 0.1(2) . . . . ?
N7 N6 C3 C4 178.68(17) . . . . ?
N8 C3 C4 C4 178.8(2) . . . 2_566 ?
N9 N8 C2 N7 177.34(18) . . . . ?
N9 N8 C2 N10 -2.7(3) . . . . ?
N9 N8 C3 N6 -177.79(17) . . . . ?
N9 N8 C3 C4 3.5(3) . . . . ?
C2 N8 C3 N6 0.6(2) . . . . ?
C2 N8 C3 C4 -178.11(17) . . . . ?
C3 N6 N7 C2 -0.7(2) . . . . ?
C3 N8 C2 N7 -0.97(19) . . . . ?
C3 N8 C2 N10 178.94(18) . . . . ?
N1 N2 N3 N4 0.0(2) . . . . ?
N2 N1 C1 N4 0.1(2) . . . . ?
N2 N1 C1 N5 -179.28(16) . . . . ?
N2 N3 N4 C1 0.1(2) . . . . ?
N3 N4 C1 N1 -0.1(2) . . . . ?
N3 N4 C1 N5 179.16(18) . . . . ?
N5 N5 C1 N1 177.03(19) 2_576 . . . ?
N5 N5 C1 N4 -2.2(3) 2_576 . . . ?
C1 N1 N2 N3 0.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_cu_dm16685_0m
_database_code_depnum_ccdc_archive 'CCDC 1524816'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H2 N3 O9), C6 H12 N10'
_chemical_formula_sum            'C18 H16 N16 O18'
_chemical_formula_weight         744.47
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.2505(7)
_cell_length_b                   5.1854(3)
_cell_length_c                   23.7693(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.493(5)
_cell_angle_gamma                90
_cell_volume                     1358.86(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    540
_cell_measurement_temperature    296
_cell_measurement_theta_max      52.76
_cell_measurement_theta_min      7.61
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0892 before and 0.0433 after correction.
The Ratio of minimum to maximum transmission is 0.8214.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5230
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        65.988
_diffrn_reflns_theta_max         65.988
_diffrn_reflns_theta_min         4.080
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1433
_reflns_number_total             2292
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.156
_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)+(0.1532P)²+2.0226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
O8 \\sim O9 \\sim N3: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(O9) \\sim Ueq, Uanis(O8) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.5301(5) 0.1403(10) 0.54781(19) 0.0747(15) Uani 1 1 d . . . . .
H1 H 0.5352 -0.0082 0.5599 0.112 Uiso 1 1 calc R . . . .
O2 O 0.3471(6) -0.0131(12) 0.5812(2) 0.095(2) Uani 1 1 d . . . . .
O3 O 0.3404(5) 0.0276(10) 0.66801(18) 0.0708(15) Uani 1 1 d . . . . .
O4 O 0.4289(4) 0.4431(9) 0.71998(15) 0.0511(11) Uani 1 1 d . . . . .
O5 O 0.5916(5) 0.7565(10) 0.77954(17) 0.0687(14) Uani 1 1 d . . . . .
O6 O 0.6647(5) 1.0207(9) 0.72810(19) 0.0710(14) Uani 1 1 d . . . . .
O7 O 0.7456(4) 0.8348(10) 0.64501(19) 0.0580(12) Uani 1 1 d . . . . .
H7 H 0.738(10) 0.94(2) 0.673(5) 0.13(4) Uiso 1 1 d . . . . .
O8 O 0.8079(8) 0.581(2) 0.5630(3) 0.137(2) Uani 1 1 d . U . . .
O9 O 0.6773(8) 0.410(2) 0.5086(3) 0.143(2) Uani 1 1 d . U . . .
N1 N 0.3817(4) 0.0943(10) 0.62809(18) 0.0475(12) Uani 1 1 d . . . . .
N2 N 0.6147(4) 0.8132(10) 0.73348(18) 0.0429(11) Uani 1 1 d . . . . .
N3 N 0.7099(6) 0.4991(15) 0.5538(3) 0.0804(19) Uani 1 1 d . U . . .
C1 C 0.5452(5) 0.3013(12) 0.5912(2) 0.0459(14) Uani 1 1 d . . . . .
C2 C 0.4736(5) 0.2847(11) 0.6334(2) 0.0410(12) Uani 1 1 d . . . . .
C3 C 0.4934(5) 0.4534(11) 0.6835(2) 0.0385(12) Uani 1 1 d . . . . .
C4 C 0.5891(5) 0.6410(10) 0.6853(2) 0.0381(12) Uani 1 1 d . . . . .
C5 C 0.6599(5) 0.6613(11) 0.6431(2) 0.0432(13) Uani 1 1 d . . . . .
C6 C 0.6374(5) 0.4872(12) 0.5965(2) 0.0476(14) Uani 1 1 d . . . . .
N4 N 0.3371(5) 0.0701(12) 0.7949(2) 0.0557(14) Uani 1 1 d . . . . .
H4A H 0.360(9) 0.07(2) 0.761(4) 0.11(3) Uiso 1 1 d . . . . .
H4B H 0.260(8) -0.003(16) 0.799(3) 0.08(2) Uiso 1 1 d . . . . .
N5 N 0.4639(5) 0.4122(12) 0.83671(19) 0.0518(13) Uani 1 1 d . . . . .
H5 H 0.495(7) 0.483(15) 0.813(3) 0.07(2) Uiso 1 1 d . . . . .
N6 N 0.5017(5) 0.5216(11) 0.89015(19) 0.0556(14) Uani 1 1 d . . . . .
N7 N 0.3824(4) 0.1886(9) 0.89328(17) 0.0416(11) Uani 1 1 d . . . . .
N8 N 0.3054(6) 0.0071(12) 0.9110(2) 0.0583(14) Uani 1 1 d . . . . .
H8A H 0.351(10) -0.13(2) 0.930(4) 0.13(4) Uiso 1 1 d . . . . .
H8B H 0.243(10) 0.17(2) 0.916(4) 0.13(4) Uiso 1 1 d . . . . .
C7 C 0.3912(5) 0.2157(12) 0.8377(2) 0.0422(13) Uani 1 1 d . . . . .
C8 C 0.4509(5) 0.3819(12) 0.9236(2) 0.0436(13) Uani 1 1 d . . . . .
C9 C 0.4616(5) 0.4194(14) 0.9852(2) 0.0488(14) Uani 1 1 d . . . . .
H9 H 0.404(6) 0.315(12) 1.002(3) 0.055(17) 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 H1 0.8200 . ?
O1 C1 1.311(7) . ?
O2 N1 1.238(6) . ?
O3 N1 1.188(6) . ?
O4 C3 1.238(6) . ?
O5 N2 1.211(6) . ?
O6 N2 1.233(6) . ?
O7 H7 0.90(12) . ?
O7 C5 1.313(7) . ?
O8 N3 1.162(9) . ?
O9 N3 1.160(9) . ?
N1 C2 1.417(7) . ?
N2 C4 1.436(7) . ?
N3 C6 1.425(7) . ?
C1 C2 1.408(7) . ?
C1 C6 1.404(8) . ?
C2 C3 1.458(7) . ?
C3 C4 1.445(7) . ?
C4 C5 1.403(7) . ?
C5 C6 1.412(8) . ?
N4 H4A 0.90(10) . ?
N4 H4B 0.97(9) . ?
N4 C7 1.316(8) . ?
N5 H5 0.81(8) . ?
N5 N6 1.379(7) . ?
N5 C7 1.310(8) . ?
N6 C8 1.290(8) . ?
N7 N8 1.400(7) . ?
N7 C7 1.351(6) . ?
N7 C8 1.377(8) . ?
N8 H8A 0.95(12) . ?
N8 H8B 1.10(11) . ?
C8 C9 1.458(7) . ?
C9 C9 1.303(13) 3_667 ?
C9 H9 1.00(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
C1 O1 H1 109.5 . . ?
C5 O7 H7 106(7) . . ?
O2 N1 C2 119.1(5) . . ?
O3 N1 O2 119.0(5) . . ?
O3 N1 C2 121.8(5) . . ?
O5 N2 O6 119.3(5) . . ?
O5 N2 C4 121.7(5) . . ?
O6 N2 C4 118.9(4) . . ?
O8 N3 C6 122.5(6) . . ?
O9 N3 O8 115.7(6) . . ?
O9 N3 C6 121.6(7) . . ?
O1 C1 C2 121.3(5) . . ?
O1 C1 C6 119.0(5) . . ?
C6 C1 C2 119.7(5) . . ?
N1 C2 C3 118.7(4) . . ?
C1 C2 N1 119.3(5) . . ?
C1 C2 C3 121.9(5) . . ?
O4 C3 C2 122.1(5) . . ?
O4 C3 C4 123.0(5) . . ?
C4 C3 C2 114.8(4) . . ?
N2 C4 C3 118.2(4) . . ?
C5 C4 N2 118.1(5) . . ?
C5 C4 C3 123.7(5) . . ?
O7 C5 C4 123.0(5) . . ?
O7 C5 C6 118.7(5) . . ?
C4 C5 C6 118.3(5) . . ?
C1 C6 N3 118.9(5) . . ?
C1 C6 C5 121.5(5) . . ?
C5 C6 N3 119.5(6) . . ?
H4A N4 H4B 120(8) . . ?
C7 N4 H4A 122(7) . . ?
C7 N4 H4B 116(5) . . ?
N6 N5 H5 112(6) . . ?
C7 N5 H5 136(6) . . ?
C7 N5 N6 112.4(5) . . ?
C8 N6 N5 104.1(5) . . ?
C7 N7 N8 122.2(5) . . ?
C7 N7 C8 107.1(5) . . ?
C8 N7 N8 130.4(4) . . ?
N7 N8 H8A 110(7) . . ?
N7 N8 H8B 89(6) . . ?
H8A N8 H8B 144(8) . . ?
N4 C7 N7 125.8(6) . . ?
N5 C7 N4 128.8(5) . . ?
N5 C7 N7 105.5(5) . . ?
N6 C8 N7 110.9(5) . . ?
N6 C8 C9 125.9(6) . . ?
N7 C8 C9 123.2(5) . . ?
C8 C9 H9 114(4) . . ?
C9 C9 C8 122.8(7) 3_667 . ?
C9 C9 H9 123(4) 3_667 . ?

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
O7 H7 O6 0.90(12) 1.72(11) 2.525(6) 148(11) .
N5 H5 O4 0.81(8) 2.19(8) 2.728(6) 124(7) .
N5 H5 O5 0.81(8) 2.04(8) 2.806(7) 157(8) .

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 C1 C2 N1 -1.5(9) . . . . ?
O1 C1 C2 C3 176.7(6) . . . . ?
O1 C1 C6 N3 1.5(10) . . . . ?
O1 C1 C6 C5 -178.4(6) . . . . ?
O2 N1 C2 C1 -16.4(9) . . . . ?
O2 N1 C2 C3 165.3(6) . . . . ?
O3 N1 C2 C1 160.5(6) . . . . ?
O3 N1 C2 C3 -17.8(9) . . . . ?
O4 C3 C4 N2 3.7(8) . . . . ?
O4 C3 C4 C5 -177.5(5) . . . . ?
O5 N2 C4 C3 25.4(8) . . . . ?
O5 N2 C4 C5 -153.5(5) . . . . ?
O6 N2 C4 C3 -156.8(5) . . . . ?
O6 N2 C4 C5 24.4(8) . . . . ?
O7 C5 C6 N3 1.7(9) . . . . ?
O7 C5 C6 C1 -178.4(6) . . . . ?
O8 N3 C6 C1 -154.5(10) . . . . ?
O8 N3 C6 C5 25.4(13) . . . . ?
O9 N3 C6 C1 20.0(13) . . . . ?
O9 N3 C6 C5 -160.1(9) . . . . ?
N1 C2 C3 O4 -3.4(9) . . . . ?
N1 C2 C3 C4 179.9(5) . . . . ?
N2 C4 C5 O7 -2.1(8) . . . . ?
N2 C4 C5 C6 178.1(5) . . . . ?
C1 C2 C3 O4 178.3(5) . . . . ?
C1 C2 C3 C4 1.6(8) . . . . ?
C2 C1 C6 N3 179.2(6) . . . . ?
C2 C1 C6 C5 -0.6(9) . . . . ?
C2 C3 C4 N2 -179.6(5) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 O7 179.2(5) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 N3 -178.5(6) . . . . ?
C4 C5 C6 C1 1.4(9) . . . . ?
C6 C1 C2 N1 -179.2(5) . . . . ?
C6 C1 C2 C3 -1.0(9) . . . . ?
N5 N6 C8 N7 -0.1(7) . . . . ?
N5 N6 C8 C9 -179.5(5) . . . . ?
N6 N5 C7 N4 178.9(6) . . . . ?
N6 N5 C7 N7 -1.5(7) . . . . ?
N6 C8 C9 C9 -9.7(12) . . . 3_667 ?
N7 C8 C9 C9 170.9(8) . . . 3_667 ?
N8 N7 C7 N4 -4.7(9) . . . . ?
N8 N7 C7 N5 175.7(5) . . . . ?
N8 N7 C8 N6 -174.5(6) . . . . ?
N8 N7 C8 C9 4.9(9) . . . . ?
C7 N5 N6 C8 1.0(7) . . . . ?
C7 N7 C8 N6 -0.9(6) . . . . ?
C7 N7 C8 C9 178.6(5) . . . . ?
C8 N7 C7 N4 -179.0(6) . . . . ?
C8 N7 C7 N5 1.4(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_mo_dm16408_0m
_database_code_depnum_ccdc_archive 'CCDC 1524815'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2016-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H2 N3 O7), C6 H12 N10'
_chemical_formula_sum            'C18 H16 N16 O14'
_chemical_formula_weight         680.47
_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 0.0033 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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.804(2)
_cell_length_b                   8.943(3)
_cell_length_c                   21.067(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.639(6)
_cell_angle_gamma                90
_cell_volume                     1280.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    516
_cell_measurement_temperature    130
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0803 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.6636.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1557
_diffrn_reflns_av_unetI/netI     0.1613
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.651
_diffrn_reflns_theta_min         1.935
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1300
_reflns_number_total             2957
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1935
_refine_ls_R_factor_gt           0.0747
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.2130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), N4(H4), C9(H9)
2.c X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.6564(5) 0.7221(4) 0.37877(14) 0.0326(9) Uani 1 1 d . . . . .
O2 O 0.4478(5) 0.9281(4) 0.43684(14) 0.0344(9) Uani 1 1 d . . . . .
O3 O 0.1468(4) 0.9484(4) 0.40177(13) 0.0276(8) Uani 1 1 d . . . . .
O4 O -0.0429(5) 0.8633(4) 0.18610(14) 0.0312(9) Uani 1 1 d . . . . .
O5 O 0.1390(5) 0.7247(4) 0.12792(14) 0.0329(9) Uani 1 1 d . . . . .
O6 O 0.8852(4) 0.5985(4) 0.29393(15) 0.0351(10) Uani 1 1 d . . . . .
O7 O 0.7534(5) 0.5460(4) 0.20170(15) 0.0362(10) Uani 1 1 d . . . . .
N1 N 0.3176(5) 0.9064(5) 0.39527(16) 0.0236(10) Uani 1 1 d . . . . .
N2 N 0.1102(6) 0.7926(5) 0.17778(16) 0.0251(10) Uani 1 1 d . . . . .
N3 N 0.7468(6) 0.6069(5) 0.25436(18) 0.0268(10) Uani 1 1 d . . . . .
C1 C 0.5436(7) 0.7482(6) 0.3321(2) 0.0250(12) Uani 1 1 d . . . . .
C2 C 0.3623(6) 0.8319(6) 0.33579(19) 0.0221(11) Uani 1 1 d . . . . .
C3 C 0.2219(6) 0.8458(6) 0.28723(19) 0.0204(11) Uani 1 1 d . . . . .
H3 H 0.1019 0.8969 0.2935 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2598(6) 0.7832(6) 0.22864(19) 0.0222(11) Uani 1 1 d . . . . .
C5 C 0.4329(6) 0.7079(6) 0.2187(2) 0.0219(11) Uani 1 1 d . . . . .
H5 H 0.4571 0.6681 0.1780 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5701(6) 0.6911(6) 0.2682(2) 0.0228(11) Uani 1 1 d . . . . .
N4 N 0.9967(5) 0.6382(5) 0.43115(16) 0.0238(10) Uani 1 1 d . . . . .
H4 H 0.9061 0.6290 0.4002 0.029 Uiso 1 1 calc R . . . .
N5 N 1.1721(5) 0.5614(5) 0.43333(17) 0.0276(10) Uani 1 1 d . . . . .
N6 N 1.1467(5) 0.7086(5) 0.51692(16) 0.0226(9) Uani 1 1 d . . . . .
N7 N 1.1858(6) 0.7855(5) 0.57435(17) 0.0349(11) Uani 1 1 d . . . . .
H7A H 1.3010 0.8258 0.5736 0.042 Uiso 1 1 d GR . . . .
H7B H 1.0993 0.8550 0.5787 0.042 Uiso 1 1 d GR . . . .
N8 N 0.8324(5) 0.8175(5) 0.49373(17) 0.0279(11) Uani 1 1 d . . . . .
H8A H 0.7288 0.8230 0.4672 0.034 Uiso 1 1 calc R . . . .
H8B H 0.8377 0.8719 0.5286 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9787(6) 0.7284(6) 0.4813(2) 0.0227(11) Uani 1 1 d . . . . .
C8 C 1.2613(6) 0.6063(6) 0.4866(2) 0.0246(11) Uani 1 1 d . . . . .
C9 C 1.4506(6) 0.5554(6) 0.5121(2) 0.0250(11) Uani 1 1 d . . . . .
H9 H 1.5068 0.6051 0.5484 0.030 Uiso 1 1 calc R . . . .


_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 C1 1.241(5) . ?
O2 N1 1.232(4) . ?
O3 N1 1.235(4) . ?
O4 N2 1.238(5) . ?
O5 N2 1.236(5) . ?
O6 N3 1.231(5) . ?
O7 N3 1.239(5) . ?
N1 C2 1.463(5) . ?
N2 C4 1.446(5) . ?
N3 C6 1.459(6) . ?
C1 C2 1.448(7) . ?
C1 C6 1.458(6) . ?
C2 C3 1.373(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(6) . ?
C4 C5 1.381(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(6) . ?
N4 H4 0.8800 . ?
N4 N5 1.376(5) . ?
N4 C7 1.339(6) . ?
N5 C8 1.314(6) . ?
N6 N7 1.406(5) . ?
N6 C7 1.350(5) . ?
N6 C8 1.378(6) . ?
N7 H7A 0.8637 . ?
N7 H7B 0.8639 . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C7 1.311(6) . ?
C8 C9 1.446(6) . ?
C9 C9 1.314(9) 3_866 ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O3 121.5(4) . . ?
O2 N1 C2 120.6(4) . . ?
O3 N1 C2 117.8(3) . . ?
O4 N2 C4 119.5(4) . . ?
O5 N2 O4 122.6(4) . . ?
O5 N2 C4 117.8(4) . . ?
O6 N3 O7 121.4(4) . . ?
O6 N3 C6 120.5(4) . . ?
O7 N3 C6 118.0(4) . . ?
O1 C1 C2 123.5(4) . . ?
O1 C1 C6 124.6(4) . . ?
C2 C1 C6 111.9(4) . . ?
C1 C2 N1 119.5(4) . . ?
C3 C2 N1 115.6(4) . . ?
C3 C2 C1 124.9(4) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 N2 118.8(4) . . ?
C5 C4 N2 119.5(4) . . ?
C5 C4 C3 121.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 N3 120.2(4) . . ?
C5 C6 N3 116.2(4) . . ?
C5 C6 C1 123.6(4) . . ?
N5 N4 H4 123.7 . . ?
C7 N4 H4 123.7 . . ?
C7 N4 N5 112.7(4) . . ?
C8 N5 N4 104.0(4) . . ?
C7 N6 N7 122.4(4) . . ?
C7 N6 C8 108.2(4) . . ?
C8 N6 N7 129.4(4) . . ?
N6 N7 H7A 108.9 . . ?
N6 N7 H7B 109.9 . . ?
H7A N7 H7B 109.0 . . ?
H8A N8 H8B 120.0 . . ?
C7 N8 H8A 120.0 . . ?
C7 N8 H8B 120.0 . . ?
N4 C7 N6 104.7(4) . . ?
N8 C7 N4 128.5(4) . . ?
N8 C7 N6 126.9(4) . . ?
N5 C8 N6 110.5(4) . . ?
N5 C8 C9 126.1(4) . . ?
N6 C8 C9 123.4(4) . . ?
C8 C9 H9 118.1 . . ?
C9 C9 C8 123.8(5) 3_866 . ?
C9 C9 H9 118.1 3_866 . ?

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
N4 H4 O1 0.88 1.93 2.627(5) 135.4 .
N8 H8A O1 0.88 2.11 2.785(5) 133.2 .

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 C1 C2 N1 7.7(8) . . . . ?
O1 C1 C2 C3 -170.8(5) . . . . ?
O1 C1 C6 N3 -5.2(8) . . . . ?
O1 C1 C6 C5 172.8(5) . . . . ?
O2 N1 C2 C1 16.7(7) . . . . ?
O2 N1 C2 C3 -164.6(4) . . . . ?
O3 N1 C2 C1 -164.5(4) . . . . ?
O3 N1 C2 C3 14.2(6) . . . . ?
O4 N2 C4 C3 4.3(7) . . . . ?
O4 N2 C4 C5 -178.1(4) . . . . ?
O5 N2 C4 C3 -173.6(4) . . . . ?
O5 N2 C4 C5 4.0(7) . . . . ?
O6 N3 C6 C1 -8.8(7) . . . . ?
O6 N3 C6 C5 173.1(5) . . . . ?
O7 N3 C6 C1 171.9(4) . . . . ?
O7 N3 C6 C5 -6.2(6) . . . . ?
N1 C2 C3 C4 177.2(4) . . . . ?
N2 C4 C5 C6 -176.1(4) . . . . ?
C1 C2 C3 C4 -4.2(8) . . . . ?
C2 C1 C6 N3 178.4(4) . . . . ?
C2 C1 C6 C5 -3.6(7) . . . . ?
C2 C3 C4 N2 177.9(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C4 C5 C6 N3 178.4(4) . . . . ?
C4 C5 C6 C1 0.4(8) . . . . ?
C6 C1 C2 N1 -175.8(4) . . . . ?
C6 C1 C2 C3 5.6(7) . . . . ?
N4 N5 C8 N6 -0.3(5) . . . . ?
N4 N5 C8 C9 178.3(5) . . . . ?
N5 N4 C7 N6 -0.3(5) . . . . ?
N5 N4 C7 N8 179.4(5) . . . . ?
N5 C8 C9 C9 -7.5(10) . . . 3_866 ?
N6 C8 C9 C9 171.0(6) . . . 3_866 ?
N7 N6 C7 N4 179.6(4) . . . . ?
N7 N6 C7 N8 -0.1(8) . . . . ?
N7 N6 C8 N5 -179.3(4) . . . . ?
N7 N6 C8 C9 2.0(8) . . . . ?
C7 N4 N5 C8 0.4(5) . . . . ?
C7 N6 C8 N5 0.1(6) . . . . ?
C7 N6 C8 C9 -178.5(4) . . . . ?
C8 N6 C7 N4 0.1(5) . . . . ?
C8 N6 C7 N8 -179.6(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_mo_te-no3_0ma
_database_code_depnum_ccdc_archive 'CCDC 1526086'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H12 N10, 2(N O3)'
_chemical_formula_sum            'C6 H12 N12 O6'
_chemical_formula_weight         348.28
_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 0.0033 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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   15.095(3)
_cell_length_b                   6.7677(12)
_cell_length_c                   13.289(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1357.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.780
_cell_measurement_theta_min      2.699
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0768 before and 0.0636 after correction. The Ratio of minimum to maximum transmission is 0.8576. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9013
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.699
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1165
_reflns_number_total             1547
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.044
_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)+(0.0711P)²+0.1689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Rotating group:
 N5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.032
;
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 0.84503(11) -0.0007(3) 0.16352(12) 0.0346(4) Uani 1 1 d . . . . .
H1A H 0.8933 -0.0136 0.1973 0.042 Uiso 1 1 calc R . . . .
H1B H 0.8471 0.0265 0.1003 0.042 Uiso 1 1 calc R . . . .
O1 O 0.53939(11) 0.4127(3) 0.34264(10) 0.0487(4) Uani 1 1 d . U . . .
O2 O 0.49860(9) 0.2698(2) 0.48035(11) 0.0461(4) Uani 1 1 d . . . . .
O3 O 0.63587(9) 0.3517(2) 0.45879(9) 0.0380(4) Uani 1 1 d . . . . .
N4 N 0.68812(9) -0.0092(2) 0.16336(10) 0.0251(3) Uani 1 1 d . . . . .
N2 N 0.75104(10) -0.0643(2) 0.30470(11) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.7913 -0.0805 0.3498 0.036 Uiso 1 1 calc R . . . .
N5 N 0.68046(11) 0.0381(2) 0.06094(10) 0.0334(4) Uani 1 1 d . . . . .
H5A H 0.6637 -0.0645 0.0276 0.040 Uiso 1 1 d GR . . . .
H5B H 0.6419 0.1308 0.0536 0.040 Uiso 1 1 d GR . . . .
N6 N 0.55626(10) 0.3454(2) 0.42700(11) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.76781(12) -0.0226(2) 0.20860(13) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.62415(12) -0.0462(2) 0.23587(13) 0.0265(4) Uani 1 1 d . . . . .
C3 C 0.53045(12) -0.0480(3) 0.21429(14) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.5122 -0.0493 0.1474 0.037 Uiso 1 1 calc R . . . .
N3 N 0.66153(11) -0.0785(2) 0.32316(11) 0.0317(4) 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 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.319(2) . ?
O1 N6 1.237(2) . ?
O2 N6 1.2337(19) . ?
O3 N6 1.2746(19) . ?
N4 N5 1.4030(19) . ?
N4 C1 1.348(2) . ?
N4 C2 1.387(2) . ?
N2 H2 0.8600 . ?
N2 C1 1.332(2) . ?
N2 N3 1.376(2) . ?
N5 H5A 0.8613 . ?
N5 H5B 0.8611 . ?
C2 C3 1.443(3) . ?
C2 N3 1.308(2) . ?
C3 C3 1.321(4) 3_655 ?
C3 H3 0.9300 . ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C1 N4 N5 121.44(14) . . ?
C1 N4 C2 107.42(14) . . ?
C2 N4 N5 131.14(14) . . ?
C1 N2 H2 124.1 . . ?
C1 N2 N3 111.85(15) . . ?
N3 N2 H2 124.1 . . ?
N4 N5 H5A 109.8 . . ?
N4 N5 H5B 109.4 . . ?
H5A N5 H5B 109.3 . . ?
O1 N6 O3 118.84(15) . . ?
O2 N6 O1 121.91(16) . . ?
O2 N6 O3 119.24(15) . . ?
N1 C1 N4 125.35(16) . . ?
N1 C1 N2 128.84(17) . . ?
N2 C1 N4 105.80(15) . . ?
N4 C2 C3 123.08(15) . . ?
N3 C2 N4 110.24(16) . . ?
N3 C2 C3 126.68(17) . . ?
C2 C3 H3 118.7 . . ?
C3 C3 C2 122.6(2) 3_655 . ?
C3 C3 H3 118.7 3_655 . ?
C2 N3 N2 104.69(14) . . ?

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
N4 C2 C3 C3 -167.59(11) . . . 3_655 ?
N4 C2 N3 N2 -0.86(18) . . . . ?
N5 N4 C1 N1 -2.4(3) . . . . ?
N5 N4 C1 N2 178.54(15) . . . . ?
N5 N4 C2 C3 2.2(3) . . . . ?
N5 N4 C2 N3 -178.03(17) . . . . ?
C1 N4 C2 C3 -178.83(16) . . . . ?
C1 N4 C2 N3 0.89(19) . . . . ?
C1 N2 N3 C2 0.5(2) . . . . ?
C2 N4 C1 N1 178.55(17) . . . . ?
C2 N4 C1 N2 -0.51(18) . . . . ?
C3 C2 N3 N2 178.85(17) . . . . ?
N3 N2 C1 N1 -179.02(18) . . . . ?
N3 N2 C1 N4 -0.01(19) . . . . ?
N3 C2 C3 C3 12.7(2) . . . 3_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
