# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shi_3008_iomi
_database_code_depnum_ccdc_archive 'CCDC 1435862'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2015-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H9 N3 O5, C4 H9 N O'
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N3 O3'
_chemical_oxdiff_usercomment     'SPS_1013 SCG_01a'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'

_cell_length_a                   13.0499(9)
_cell_length_b                   6.4263(4)
_cell_length_c                   10.3169(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.655(6)
_cell_angle_gamma                90.00
_cell_volume                     864.28(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    169.9(4)
_cell_measurement_theta_max      25.4020
_cell_measurement_theta_min      1.5740
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5906
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.56
_diffrn_ambient_temperature      169.9(4)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega   57.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  178.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -52.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -38.0000    0.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -99.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   44.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega  -53.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -19.0000 -180.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0232207000
_diffrn_orient_matrix_UB_12      0.0913061000
_diffrn_orient_matrix_UB_13      0.0264207000
_diffrn_orient_matrix_UB_21      -0.0414144000
_diffrn_orient_matrix_UB_22      0.0122993000
_diffrn_orient_matrix_UB_23      0.0414762000
_diffrn_orient_matrix_UB_31      0.0265656000
_diffrn_orient_matrix_UB_32      -0.0607318000
_diffrn_orient_matrix_UB_33      0.0481868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2306
_reflns_number_total             2684
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1264
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.9358(2) -0.6906(4) 0.5660(3) 0.0469(7) Uani 1 d . . .
H1 H 0.9755 -0.6510 0.6248 0.070 Uiso 1 calc . . GR
O2 O 0.63153(19) -0.0463(4) 0.2798(2) 0.0397(6) Uani 1 d . . .
O3 O 0.44491(16) 0.5873(3) 0.4066(2) 0.0281(5) Uani 1 d . . .
O4 O 0.3382(2) 0.7410(4) 0.2079(2) 0.0467(7) Uani 1 d . . .
O5 O 0.2980(2) 1.0189(4) 0.3175(3) 0.0520(8) Uani 1 d . . .
N1 N 0.62963(19) 0.0750(4) 0.4875(3) 0.0289(6) Uani 1 d . . .
H1A H 0.6478 0.0550 0.5677 0.035 Uiso 1 calc . . R
N2 N 0.5686(2) 0.2420(4) 0.4535(3) 0.0299(6) Uani 1 d . . .
N3 N 0.3410(2) 0.8492(4) 0.3073(3) 0.0355(7) Uani 1 d . . .
C1 C 0.8727(3) -0.5324(5) 0.5285(3) 0.0325(8) Uani 1 d . . .
C2 C 0.8095(3) -0.5603(5) 0.4180(4) 0.0346(8) Uani 1 d . . .
H2 H 0.8116 -0.6848 0.3723 0.042 Uiso 1 calc . . R
C3 C 0.7436(3) -0.4046(6) 0.3757(3) 0.0354(8) Uani 1 d . . .
H3 H 0.7037 -0.4233 0.2995 0.042 Uiso 1 calc . . R
C4 C 0.7357(2) -0.2200(5) 0.4446(3) 0.0276(7) Uani 1 d . . .
C5 C 0.7995(3) -0.1935(5) 0.5561(3) 0.0331(8) Uani 1 d . . .
H5 H 0.7960 -0.0709 0.6036 0.040 Uiso 1 calc . . R
C6 C 0.8677(3) -0.3479(5) 0.5963(3) 0.0342(8) Uani 1 d . . .
H6 H 0.9105 -0.3271 0.6697 0.041 Uiso 1 calc . . R
C7 C 0.6618(3) -0.0595(5) 0.3957(3) 0.0306(8) Uani 1 d . . .
C8 C 0.5468(3) 0.3595(5) 0.5488(3) 0.0330(8) Uani 1 d . . .
H8 H 0.5695 0.3230 0.6325 0.040 Uiso 1 calc . . R
C9 C 0.4878(2) 0.5470(5) 0.5288(3) 0.0279(7) Uani 1 d . . .
C10 C 0.4675(3) 0.7062(5) 0.6116(3) 0.0362(8) Uani 1 d . . .
H10 H 0.4882 0.7150 0.6989 0.043 Uiso 1 calc . . R
C11 C 0.4095(3) 0.8536(5) 0.5399(3) 0.0358(8) Uani 1 d . . .
H11 H 0.3847 0.9798 0.5694 0.043 Uiso 1 calc . . R
C12 C 0.3973(2) 0.7737(5) 0.4184(3) 0.0285(7) Uani 1 d . . .
O6 O 0.0589(2) 0.5843(5) 0.2618(2) 0.0522(8) Uani 1 d . . .
N4 N 0.1281(3) 0.6653(6) 0.4553(3) 0.0592(10) Uani 1 d . . .
C13 C 0.1795(3) 0.4579(6) 0.4604(4) 0.0502(10) Uani 1 d . . .
H13A H 0.2311 0.4566 0.5299 0.075 Uiso 1 calc . . GR
H13B H 0.2109 0.4320 0.3797 0.075 Uiso 1 calc . . GR
H13C H 0.1297 0.3517 0.4751 0.075 Uiso 1 calc . . GR
C14 C 0.1409(4) 0.8060(7) 0.5688(4) 0.0629(13) Uani 1 d . . .
H14A H 0.0804 0.8013 0.6181 0.094 Uiso 1 calc . . GR
H14B H 0.1518 0.9457 0.5394 0.094 Uiso 1 calc . . GR
H14C H 0.1990 0.7621 0.6224 0.094 Uiso 1 calc . . GR
C15 C 0.0696(3) 0.7166(7) 0.3545(4) 0.0563(12) Uani 1 d . . .
C16 C 0.0180(3) 0.9234(6) 0.3501(4) 0.0504(10) Uani 1 d . . .
H16A H -0.0102 0.9516 0.4325 0.076 Uiso 1 calc . . GR
H16B H -0.0360 0.9227 0.2837 0.076 Uiso 1 calc . . GR
H16C H 0.0671 1.0292 0.3312 0.076 Uiso 1 calc . . GR


_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 1.354(4) . ?
O2 C7 1.245(4) . ?
O3 C9 1.379(4) . ?
O3 C12 1.357(4) . ?
O4 N3 1.238(4) . ?
O5 N3 1.233(4) . ?
N1 H1A 0.8600 . ?
N1 N2 1.372(4) . ?
N1 C7 1.363(4) . ?
N2 C8 1.282(4) . ?
N3 C12 1.419(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(5) . ?
C4 C5 1.398(4) . ?
C4 C7 1.484(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.440(4) . ?
C9 C10 1.367(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.402(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.357(5) . ?
O6 C15 1.282(5) . ?
N4 C13 1.492(6) . ?
N4 C14 1.483(5) . ?
N4 C15 1.303(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.490(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 . . ?
C12 O3 C9 104.6(2) . . ?
N2 N1 H1A 119.6 . . ?
C7 N1 H1A 119.6 . . ?
C7 N1 N2 120.8(3) . . ?
C8 N2 N1 114.3(3) . . ?
O4 N3 C12 118.2(3) . . ?
O5 N3 O4 124.8(3) . . ?
O5 N3 C12 117.0(3) . . ?
O1 C1 C2 118.0(3) . . ?
O1 C1 C6 122.9(3) . . ?
C6 C1 C2 119.1(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 C7 118.8(3) . . ?
C5 C4 C7 123.2(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O2 C7 N1 122.0(3) . . ?
O2 C7 C4 123.1(3) . . ?
N1 C7 C4 114.9(3) . . ?
N2 C8 H8 119.4 . . ?
N2 C8 C9 121.3(3) . . ?
C9 C8 H8 119.4 . . ?
O3 C9 C8 118.7(3) . . ?
C10 C9 O3 110.4(3) . . ?
C10 C9 C8 130.9(3) . . ?
C9 C10 H10 126.5 . . ?
C9 C10 C11 106.9(3) . . ?
C11 C10 H10 126.5 . . ?
C10 C11 H11 127.2 . . ?
C12 C11 C10 105.6(3) . . ?
C12 C11 H11 127.2 . . ?
O3 C12 N3 116.8(3) . . ?
C11 C12 O3 112.5(3) . . ?
C11 C12 N3 130.6(3) . . ?
C14 N4 C13 118.8(4) . . ?
C15 N4 C13 120.0(4) . . ?
C15 N4 C14 121.1(4) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 N4 117.9(4) . . ?
O6 C15 C16 122.3(4) . . ?
N4 C15 C16 119.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 H1 O6 0.82 1.79 2.612(4) 174.8 2_655
N1 H1A O2 0.86 2.21 3.020(3) 157.3 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 C3 179.9(3) . . . . ?
O1 C1 C6 C5 -178.0(3) . . . . ?
O3 C9 C10 C11 0.0(4) . . . . ?
O4 N3 C12 O3 0.5(4) . . . . ?
O4 N3 C12 C11 -176.7(4) . . . . ?
O5 N3 C12 O3 -179.7(3) . . . . ?
O5 N3 C12 C11 3.1(5) . . . . ?
N1 N2 C8 C9 176.9(3) . . . . ?
N2 N1 C7 O2 -5.4(5) . . . . ?
N2 N1 C7 C4 174.1(3) . . . . ?
N2 C8 C9 O3 7.1(4) . . . . ?
N2 C8 C9 C10 -170.2(3) . . . . ?
C1 C2 C3 C4 -2.6(5) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C2 C3 C4 C7 -178.7(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C7 O2 -24.3(5) . . . . ?
C3 C4 C7 N1 156.2(3) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C5 C4 C7 O2 154.5(3) . . . . ?
C5 C4 C7 N1 -25.0(5) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C7 N1 N2 C8 -177.8(3) . . . . ?
C7 C4 C5 C6 -179.3(3) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C9 O3 C12 N3 -176.6(3) . . . . ?
C9 O3 C12 C11 1.1(3) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 O3 -1.1(4) . . . . ?
C10 C11 C12 N3 176.2(3) . . . . ?
C12 O3 C9 C8 -178.6(3) . . . . ?
C12 O3 C9 C10 -0.7(3) . . . . ?
C13 N4 C15 O6 -0.3(5) . . . . ?
C13 N4 C15 C16 179.7(3) . . . . ?
C14 N4 C15 O6 -177.4(4) . . . . ?
C14 N4 C15 C16 2.6(6) . . . . ?

_olex2_date_sample_data_collection 2015-01-26
_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_shi_3009_iomi
_database_code_depnum_ccdc_archive 'CCDC 1435863'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2015-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C12 H9 N3 O5), 2(C2 H6 O S), H2 O'
_chemical_formula_sum            'C28 H32 N6 O13 S2'
_chemical_formula_weight         724.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N3 O3 S1'
_chemical_oxdiff_usercomment     'sPS_1013 SCG_03b'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7327(7)
_cell_length_b                   10.8661(7)
_cell_length_c                   38.348(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.185(7)
_cell_angle_gamma                90.00
_cell_volume                     3217.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      26.4260
_cell_measurement_theta_min      2.1190
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11913
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   76.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -99.0000   60.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0480592000
_diffrn_orient_matrix_UB_12      0.0056523000
_diffrn_orient_matrix_UB_13      -0.0151231000
_diffrn_orient_matrix_UB_21      -0.0780917000
_diffrn_orient_matrix_UB_22      0.0082019000
_diffrn_orient_matrix_UB_23      -0.0103416000
_diffrn_orient_matrix_UB_31      0.0056586000
_diffrn_orient_matrix_UB_32      0.0645537000
_diffrn_orient_matrix_UB_33      0.0026665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3845
_reflns_number_total             5674
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1067
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1AA), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C8A(H8A), C10A(H10A),
 C11A(H11A), N1B(H1BA), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C8B(H8B),
 C10B(H10B), C11B(H11B)
2.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C13B(H13D,H13E,H13F), C14B(H14D,
 H14E,H14F)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1A O 1.1212(3) 0.49810(19) 0.09030(6) 0.0320(6) Uani 1 d . . .
H1A H 1.0914 0.4546 0.0736 0.048 Uiso 1 calc . . GR
O2A O 0.9228(3) 0.16410(17) 0.21871(6) 0.0284(6) Uani 1 d . . .
O3A O 0.7131(3) 0.44380(17) 0.35082(5) 0.0226(5) Uani 1 d . . .
O4A O 0.6529(3) 0.57366(19) 0.40548(6) 0.0388(7) Uani 1 d . . .
O5A O 0.5380(3) 0.4174(2) 0.43109(6) 0.0449(7) Uani 1 d . . .
N1A N 0.9080(3) 0.3548(2) 0.24241(7) 0.0222(7) Uani 1 d . . .
H1AA H 0.9288 0.4322 0.2405 0.027 Uiso 1 calc . . R
N2A N 0.8398(3) 0.3094(2) 0.27209(7) 0.0210(6) Uani 1 d . . .
N3A N 0.6089(4) 0.4650(2) 0.40683(7) 0.0301(7) Uani 1 d . . .
C1A C 1.0806(4) 0.4416(3) 0.12020(9) 0.0219(8) Uani 1 d . . .
C2A C 1.1183(4) 0.5024(3) 0.15148(9) 0.0227(8) Uani 1 d . . .
H2A H 1.1723 0.5789 0.1513 0.027 Uiso 1 calc . . R
C3A C 1.0770(4) 0.4513(3) 0.18277(8) 0.0216(8) Uani 1 d . . .
H3A H 1.1028 0.4935 0.2035 0.026 Uiso 1 calc . . R
C4A C 0.9963(4) 0.3363(3) 0.18357(8) 0.0198(7) Uani 1 d . . .
C5A C 0.9614(4) 0.2755(3) 0.15215(8) 0.0224(8) Uani 1 d . . .
H5A H 0.9103 0.1981 0.1523 0.027 Uiso 1 calc . . R
C6A C 1.0007(4) 0.3272(3) 0.12072(9) 0.0238(8) Uani 1 d . . .
H6A H 0.9738 0.2856 0.0999 0.029 Uiso 1 calc . . R
C7A C 0.9423(4) 0.2765(3) 0.21602(8) 0.0198(7) Uani 1 d . . .
C8A C 0.8093(4) 0.3894(3) 0.29517(8) 0.0209(8) Uani 1 d . . .
H8A H 0.8371 0.4716 0.2917 0.025 Uiso 1 calc . . R
C9A C 0.7316(4) 0.3514(3) 0.32655(8) 0.0221(8) Uani 1 d . . .
C10A C 0.6711(4) 0.2436(3) 0.33909(9) 0.0243(8) Uani 1 d . . .
H10A H 0.6691 0.1679 0.3277 0.029 Uiso 1 calc . . R
C11A C 0.6124(4) 0.2678(3) 0.37233(9) 0.0257(8) Uani 1 d . . .
H11A H 0.5636 0.2122 0.3874 0.031 Uiso 1 calc . . R
C12A C 0.6416(4) 0.3882(3) 0.37775(9) 0.0227(8) Uani 1 d . . .
O1B O 1.4110(3) 0.02289(18) 0.08143(6) 0.0310(6) Uani 1 d . . .
H1B H 1.4430 -0.0332 0.0690 0.046 Uiso 1 calc . . GR
O2B O 1.2134(3) -0.26557(18) 0.21708(6) 0.0295(6) Uani 1 d . . .
O3B O 0.9513(3) -0.01076(18) 0.34383(6) 0.0245(5) Uani 1 d . . .
O4B O 0.8994(3) 0.0979(2) 0.40295(6) 0.0394(7) Uani 1 d . . .
O5B O 0.8942(3) -0.0764(2) 0.43052(6) 0.0459(7) Uani 1 d . . .
N1B N 1.1177(3) -0.0765(2) 0.23093(7) 0.0255(7) Uani 1 d . . .
H1BA H 1.0998 -0.0010 0.2251 0.031 Uiso 1 calc . . R
N2B N 1.0717(3) -0.1202(2) 0.26235(7) 0.0242(7) Uani 1 d . . .
N3B N 0.9083(4) -0.0148(2) 0.40384(8) 0.0307(7) Uani 1 d . . .
C1B C 1.3587(4) -0.0240(3) 0.11175(9) 0.0224(8) Uani 1 d . . .
C2B C 1.2669(4) 0.0535(3) 0.13255(9) 0.0263(8) Uani 1 d . . .
H2B H 1.2408 0.1331 0.1251 0.032 Uiso 1 calc . . R
C3B C 1.2142(4) 0.0130(3) 0.16428(9) 0.0247(8) Uani 1 d . . .
H3B H 1.1538 0.0661 0.1782 0.030 Uiso 1 calc . . R
C4B C 1.2502(4) -0.1064(3) 0.17578(8) 0.0197(7) Uani 1 d . . .
C5B C 1.3429(4) -0.1829(3) 0.15443(8) 0.0213(8) Uani 1 d . . .
H5B H 1.3689 -0.2627 0.1617 0.026 Uiso 1 calc . . R
C6B C 1.3969(4) -0.1431(3) 0.12282(9) 0.0242(8) Uani 1 d . . .
H6B H 1.4587 -0.1956 0.1089 0.029 Uiso 1 calc . . R
C7B C 1.1935(4) -0.1571(3) 0.20905(8) 0.0217(8) Uani 1 d . . .
C8B C 1.0162(4) -0.0436(3) 0.28432(9) 0.0253(8) Uani 1 d . . .
H8B H 0.9991 0.0391 0.2790 0.030 Uiso 1 calc . . R
C9B C 0.9821(4) -0.0940(3) 0.31783(9) 0.0224(8) Uani 1 d . . .
C10B C 0.9833(4) -0.2100(3) 0.33083(9) 0.0288(8) Uani 1 d . . .
H10B H 0.9992 -0.2822 0.3184 0.035 Uiso 1 calc . . R
C11B C 0.9560(4) -0.2005(3) 0.36662(9) 0.0296(9) Uani 1 d . . .
H11B H 0.9511 -0.2645 0.3826 0.035 Uiso 1 calc . . R
C12B C 0.9383(4) -0.0798(3) 0.37288(9) 0.0233(8) Uani 1 d . . .
S1A S 1.18733(11) 0.30707(7) 0.01587(2) 0.0266(2) Uani 1 d . . .
O6A O 1.0353(3) 0.36066(18) 0.03401(6) 0.0300(6) Uani 1 d . . .
C13A C 1.1479(4) 0.3384(3) -0.02926(8) 0.0294(9) Uani 1 d . . .
H13A H 1.1467 0.4258 -0.0329 0.044 Uiso 1 calc . . GR
H13B H 1.0380 0.3044 -0.0371 0.044 Uiso 1 calc . . GR
H13C H 1.2378 0.3020 -0.0421 0.044 Uiso 1 calc . . GR
C14A C 1.1546(4) 0.1449(3) 0.01468(9) 0.0339(9) Uani 1 d . . .
H14A H 1.0417 0.1273 0.0042 0.051 Uiso 1 calc . . GR
H14B H 1.1633 0.1128 0.0380 0.051 Uiso 1 calc . . GR
H14C H 1.2411 0.1073 0.0012 0.051 Uiso 1 calc . . GR
S1B S 1.32911(11) -0.19824(7) 0.01974(2) 0.0273(2) Uani 1 d . . .
O6B O 1.4978(3) -0.14964(18) 0.03688(6) 0.0289(6) Uani 1 d . . .
C13B C 1.3424(4) -0.1745(3) -0.02581(8) 0.0343(9) Uani 1 d . . .
H13D H 1.4481 -0.2095 -0.0333 0.051 Uiso 1 calc . . GR
H13E H 1.3405 -0.0879 -0.0307 0.051 Uiso 1 calc . . GR
H13F H 1.2456 -0.2134 -0.0381 0.051 Uiso 1 calc . . GR
C14B C 1.3449(4) -0.3611(3) 0.02017(10) 0.0403(10) Uani 1 d . . .
H14D H 1.3375 -0.3906 0.0436 0.061 Uiso 1 calc . . GR
H14E H 1.4537 -0.3855 0.0115 0.061 Uiso 1 calc . . GR
H14F H 1.2520 -0.3955 0.0056 0.061 Uiso 1 calc . . GR
O1W O 0.9311(3) 0.61298(18) 0.24908(7) 0.0362(6) Uani 1 d . . .
H1WA H 1.0146 0.6600 0.2445 0.054 Uiso 1 d . . G
H1WB H 0.8366 0.6529 0.2470 0.054 Uiso 1 d . . G


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A H1A 0.8200 . ?
O1A C1A 1.353(3) . ?
O2A C7A 1.236(3) . ?
O3A C9A 1.382(3) . ?
O3A C12A 1.342(4) . ?
O4A N3A 1.231(3) . ?
O5A N3A 1.221(3) . ?
N1A H1AA 0.8600 . ?
N1A N2A 1.372(3) . ?
N1A C7A 1.359(4) . ?
N2A C8A 1.272(4) . ?
N3A C12A 1.426(4) . ?
C1A C2A 1.387(4) . ?
C1A C6A 1.388(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.376(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.398(4) . ?
C4A C5A 1.387(4) . ?
C4A C7A 1.484(4) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.379(4) . ?
C6A H6A 0.9300 . ?
C8A H8A 0.9300 . ?
C8A C9A 1.435(4) . ?
C9A C10A 1.360(4) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.402(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.342(4) . ?
O1B H1B 0.8200 . ?
O1B C1B 1.352(3) . ?
O2B C7B 1.226(3) . ?
O3B C9B 1.377(3) . ?
O3B C12B 1.352(4) . ?
O4B N3B 1.227(3) . ?
O5B N3B 1.232(3) . ?
N1B H1BA 0.8600 . ?
N1B N2B 1.361(3) . ?
N1B C7B 1.368(4) . ?
N2B C8B 1.276(4) . ?
N3B C12B 1.412(4) . ?
C1B C2B 1.383(4) . ?
C1B C6B 1.388(4) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.377(4) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.394(4) . ?
C4B C5B 1.393(4) . ?
C4B C7B 1.478(4) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.374(4) . ?
C6B H6B 0.9300 . ?
C8B H8B 0.9300 . ?
C8B C9B 1.434(4) . ?
C9B C10B 1.356(4) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.404(4) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.341(4) . ?
S1A O6A 1.515(2) . ?
S1A C13A 1.774(3) . ?
S1A C14A 1.780(3) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
S1B O6B 1.523(2) . ?
S1B C13B 1.774(3) . ?
S1B C14B 1.774(3) . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
O1W H1WA 0.8488 . ?
O1W H1WB 0.8499 . ?

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
C1A O1A H1A 109.5 . . ?
C12A O3A C9A 104.7(2) . . ?
N2A N1A H1AA 120.2 . . ?
C7A N1A H1AA 120.2 . . ?
C7A N1A N2A 119.5(2) . . ?
C8A N2A N1A 115.2(2) . . ?
O4A N3A C12A 117.8(3) . . ?
O5A N3A O4A 125.1(3) . . ?
O5A N3A C12A 117.1(3) . . ?
O1A C1A C2A 118.0(3) . . ?
O1A C1A C6A 122.9(3) . . ?
C2A C1A C6A 119.1(3) . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A C1A 120.9(3) . . ?
C3A C2A H2A 119.5 . . ?
C2A C3A H3A 119.8 . . ?
C2A C3A C4A 120.4(3) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A C7A 123.8(3) . . ?
C5A C4A C3A 118.2(3) . . ?
C5A C4A C7A 118.0(3) . . ?
C4A C5A H5A 119.2 . . ?
C6A C5A C4A 121.6(3) . . ?
C6A C5A H5A 119.2 . . ?
C1A C6A H6A 120.1 . . ?
C5A C6A C1A 119.8(3) . . ?
C5A C6A H6A 120.1 . . ?
O2A C7A N1A 121.7(3) . . ?
O2A C7A C4A 123.0(3) . . ?
N1A C7A C4A 115.2(3) . . ?
N2A C8A H8A 120.3 . . ?
N2A C8A C9A 119.3(3) . . ?
C9A C8A H8A 120.3 . . ?
O3A C9A C8A 114.8(3) . . ?
C10A C9A O3A 109.7(3) . . ?
C10A C9A C8A 135.5(3) . . ?
C9A C10A H10A 126.4 . . ?
C9A C10A C11A 107.2(3) . . ?
C11A C10A H10A 126.4 . . ?
C10A C11A H11A 127.4 . . ?
C12A C11A C10A 105.3(3) . . ?
C12A C11A H11A 127.4 . . ?
O3A C12A N3A 115.9(3) . . ?
O3A C12A C11A 113.1(3) . . ?
C11A C12A N3A 131.0(3) . . ?
C1B O1B H1B 109.5 . . ?
C12B O3B C9B 104.8(2) . . ?
N2B N1B H1BA 121.3 . . ?
N2B N1B C7B 117.5(2) . . ?
C7B N1B H1BA 121.3 . . ?
C8B N2B N1B 118.1(3) . . ?
O4B N3B O5B 123.9(3) . . ?
O4B N3B C12B 119.2(3) . . ?
O5B N3B C12B 116.9(3) . . ?
O1B C1B C2B 117.0(3) . . ?
O1B C1B C6B 123.1(3) . . ?
C2B C1B C6B 119.9(3) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B C1B 120.1(3) . . ?
C3B C2B H2B 119.9 . . ?
C2B C3B H3B 119.5 . . ?
C2B C3B C4B 120.9(3) . . ?
C4B C3B H3B 119.5 . . ?
C3B C4B C7B 123.8(3) . . ?
C5B C4B C3B 118.0(3) . . ?
C5B C4B C7B 118.2(3) . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B C4B 121.5(3) . . ?
C6B C5B H5B 119.2 . . ?
C1B C6B H6B 120.2 . . ?
C5B C6B C1B 119.5(3) . . ?
C5B C6B H6B 120.2 . . ?
O2B C7B N1B 120.9(3) . . ?
O2B C7B C4B 122.4(3) . . ?
N1B C7B C4B 116.6(3) . . ?
N2B C8B H8B 122.3 . . ?
N2B C8B C9B 115.4(3) . . ?
C9B C8B H8B 122.3 . . ?
O3B C9B C8B 116.5(3) . . ?
C10B C9B O3B 110.0(3) . . ?
C10B C9B C8B 133.3(3) . . ?
C9B C10B H10B 126.5 . . ?
C9B C10B C11B 107.0(3) . . ?
C11B C10B H10B 126.5 . . ?
C10B C11B H11B 127.2 . . ?
C12B C11B C10B 105.6(3) . . ?
C12B C11B H11B 127.2 . . ?
O3B C12B N3B 116.0(3) . . ?
C11B C12B O3B 112.5(3) . . ?
C11B C12B N3B 131.5(3) . . ?
O6A S1A C13A 106.19(14) . . ?
O6A S1A C14A 106.22(14) . . ?
C13A S1A C14A 98.53(15) . . ?
S1A C13A H13A 109.5 . . ?
S1A C13A H13B 109.5 . . ?
S1A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
S1A C14A H14A 109.5 . . ?
S1A C14A H14B 109.5 . . ?
S1A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O6B S1B C13B 106.25(14) . . ?
O6B S1B C14B 106.57(14) . . ?
C13B S1B C14B 98.41(16) . . ?
S1B C13B H13D 109.5 . . ?
S1B C13B H13E 109.5 . . ?
S1B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
S1B C14B H14D 109.5 . . ?
S1B C14B H14E 109.5 . . ?
S1B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?

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
O1A H1A O6A 0.82 1.86 2.678(3) 176.2 .
N1A H1AA O1W 0.86 1.99 2.822(3) 161.9 .
O1B H1B O6B 0.82 1.83 2.648(3) 172.9 .
N1B H1BA O2A 0.86 2.26 3.041(3) 150.8 .
O1W H1WA O2B 0.85 2.07 2.882(3) 158.8 1_565
O1W H1WA N2B 0.85 2.52 3.128(3) 129.7 1_565
O1W H1WB O2A 0.85 2.46 3.114(3) 134.3 2_655
O1W H1WB N2A 0.85 2.28 3.068(3) 155.3 2_655

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
O1A C1A C2A C3A 178.6(3) . . . . ?
O1A C1A C6A C5A -179.3(3) . . . . ?
O3A C9A C10A C11A 0.0(4) . . . . ?
O4A N3A C12A O3A -2.2(4) . . . . ?
O4A N3A C12A C11A 178.2(3) . . . . ?
O5A N3A C12A O3A 177.3(3) . . . . ?
O5A N3A C12A C11A -2.3(5) . . . . ?
N1A N2A C8A C9A 177.6(3) . . . . ?
N2A N1A C7A O2A -4.0(4) . . . . ?
N2A N1A C7A C4A 173.2(2) . . . . ?
N2A C8A C9A O3A 176.4(3) . . . . ?
N2A C8A C9A C10A -2.7(6) . . . . ?
C1A C2A C3A C4A 0.2(5) . . . . ?
C2A C1A C6A C5A -0.5(5) . . . . ?
C2A C3A C4A C5A 0.6(4) . . . . ?
C2A C3A C4A C7A -177.9(3) . . . . ?
C3A C4A C5A C6A -1.5(5) . . . . ?
C3A C4A C7A O2A -156.6(3) . . . . ?
C3A C4A C7A N1A 26.2(4) . . . . ?
C4A C5A C6A C1A 1.4(5) . . . . ?
C5A C4A C7A O2A 24.8(4) . . . . ?
C5A C4A C7A N1A -152.4(3) . . . . ?
C6A C1A C2A C3A -0.3(5) . . . . ?
C7A N1A N2A C8A -179.0(3) . . . . ?
C7A C4A C5A C6A 177.2(3) . . . . ?
C8A C9A C10A C11A 179.1(4) . . . . ?
C9A O3A C12A N3A 179.9(3) . . . . ?
C9A O3A C12A C11A -0.4(3) . . . . ?
C9A C10A C11A C12A -0.2(4) . . . . ?
C10A C11A C12A O3A 0.4(4) . . . . ?
C10A C11A C12A N3A -179.9(3) . . . . ?
C12A O3A C9A C8A -179.1(3) . . . . ?
C12A O3A C9A C10A 0.2(3) . . . . ?
O1B C1B C2B C3B -178.0(3) . . . . ?
O1B C1B C6B C5B 178.3(3) . . . . ?
O3B C9B C10B C11B -1.3(4) . . . . ?
O4B N3B C12B O3B -1.5(4) . . . . ?
O4B N3B C12B C11B 178.9(3) . . . . ?
O5B N3B C12B O3B 179.3(3) . . . . ?
O5B N3B C12B C11B -0.3(5) . . . . ?
N1B N2B C8B C9B -175.6(3) . . . . ?
N2B N1B C7B O2B 2.5(4) . . . . ?
N2B N1B C7B C4B -177.1(3) . . . . ?
N2B C8B C9B O3B 169.1(3) . . . . ?
N2B C8B C9B C10B -6.1(5) . . . . ?
C1B C2B C3B C4B -0.8(5) . . . . ?
C2B C1B C6B C5B 0.1(5) . . . . ?
C2B C3B C4B C5B 0.9(5) . . . . ?
C2B C3B C4B C7B -178.3(3) . . . . ?
C3B C4B C5B C6B -0.5(5) . . . . ?
C3B C4B C7B O2B 173.3(3) . . . . ?
C3B C4B C7B N1B -7.0(4) . . . . ?
C4B C5B C6B C1B 0.0(5) . . . . ?
C5B C4B C7B O2B -5.8(5) . . . . ?
C5B C4B C7B N1B 173.8(3) . . . . ?
C6B C1B C2B C3B 0.3(5) . . . . ?
C7B N1B N2B C8B 173.4(3) . . . . ?
C7B C4B C5B C6B 178.7(3) . . . . ?
C8B C9B C10B C11B 174.1(3) . . . . ?
C9B O3B C12B N3B 179.3(3) . . . . ?
C9B O3B C12B C11B -1.1(3) . . . . ?
C9B C10B C11B C12B 0.6(4) . . . . ?
C10B C11B C12B O3B 0.3(4) . . . . ?
C10B C11B C12B N3B 179.9(3) . . . . ?
C12B O3B C9B C8B -174.8(3) . . . . ?
C12B O3B C9B C10B 1.4(3) . . . . ?

_olex2_date_sample_data_collection 2015-01-26
_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_exp_3018
_database_code_depnum_ccdc_archive 'CCDC 1435861'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_audit_creation_date             2015-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H9 N3 O5, 2(C5 H9 N O)'
_chemical_formula_sum            'C22 H27 N5 O7'
_chemical_formula_weight         473.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H27 N5 O7'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.9119(8)
_cell_length_b                   11.5956(17)
_cell_length_c                   15.219(2)
_cell_angle_alpha                78.832(12)
_cell_angle_beta                 81.329(11)
_cell_angle_gamma                75.997(12)
_cell_volume                     1154.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1071
_cell_measurement_temperature    170.2(4)
_cell_measurement_theta_max      25.9490
_cell_measurement_theta_min      1.8910
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6598
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.83
_diffrn_ambient_temperature      170.2(4)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -71.00  -43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00    7.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   24.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   38.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  178.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   38.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   -9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -38.0000 -180.0000 41
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0095130000
_diffrn_orient_matrix_UB_12      0.0253854000
_diffrn_orient_matrix_UB_13      -0.0458663000
_diffrn_orient_matrix_UB_21      -0.0181047000
_diffrn_orient_matrix_UB_22      0.0586213000
_diffrn_orient_matrix_UB_23      0.0110894000
_diffrn_orient_matrix_UB_31      0.1044144000
_diffrn_orient_matrix_UB_32      -0.0018091000
_diffrn_orient_matrix_UB_33      -0.0075710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2126
_reflns_number_total             3317
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0916
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1525P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2584
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.7104(5) 0.0437(3) 0.59278(19) 0.0390(9) Uani 1 d . . .
H1 H 0.7017 -0.0271 0.6036 0.059 Uiso 1 d . . R
O2 O 0.8026(4) 0.3161(3) 0.90456(19) 0.0346(9) Uani 1 d . . .
O3 O 0.8073(4) 0.2280(3) 1.23677(18) 0.0303(8) Uani 1 d . . .
O4 O 0.8318(6) 0.4210(3) 1.2978(2) 0.0540(11) Uani 1 d . . .
O5 O 0.8335(5) 0.3247(3) 1.4365(2) 0.0455(9) Uani 1 d . . .
N1 N 0.7711(5) 0.1349(3) 0.9898(2) 0.0275(9) Uani 1 d . . .
H1A H 0.7568 0.0631 0.9903 0.033 Uiso 1 calc . . R
N2 N 0.7834(5) 0.1727(3) 1.0690(2) 0.0285(9) Uani 1 d . . .
N3 N 0.8282(5) 0.3296(4) 1.3549(2) 0.0366(10) Uani 1 d . . .
C1 C 0.7250(6) 0.0808(4) 0.6707(3) 0.0283(11) Uani 1 d . . .
C2 C 0.6877(6) 0.0131(4) 0.7554(3) 0.0291(11) Uani 1 d . . .
H2 H 0.6493 -0.0595 0.7599 0.035 Uiso 1 calc . . R
C3 C 0.7073(6) 0.0531(4) 0.8328(3) 0.0290(11) Uani 1 d . . .
H3 H 0.6836 0.0063 0.8886 0.035 Uiso 1 calc . . R
C4 C 0.7619(6) 0.1626(4) 0.8287(3) 0.0261(11) Uani 1 d . . .
C5 C 0.7966(6) 0.2304(4) 0.7434(3) 0.0286(11) Uani 1 d . . .
H5 H 0.8340 0.3033 0.7389 0.034 Uiso 1 calc . . R
C6 C 0.7762(7) 0.1906(4) 0.6656(3) 0.0329(12) Uani 1 d . . .
H6 H 0.7970 0.2379 0.6097 0.039 Uiso 1 calc . . R
C7 C 0.7820(6) 0.2138(4) 0.9101(3) 0.0268(11) Uani 1 d . . .
C8 C 0.7794(6) 0.0910(4) 1.1398(3) 0.0278(11) Uani 1 d . . .
H8 H 0.7689 0.0145 1.1339 0.033 Uiso 1 calc . . R
C9 C 0.7909(6) 0.1156(4) 1.2278(3) 0.0281(11) Uani 1 d . . .
C10 C 0.7872(7) 0.0426(4) 1.3104(3) 0.0357(12) Uani 1 d . . .
H10 H 0.7759 -0.0374 1.3220 0.043 Uiso 1 calc . . R
C11 C 0.8038(7) 0.1122(4) 1.3746(3) 0.0333(12) Uani 1 d . . .
H11 H 0.8065 0.0879 1.4364 0.040 Uiso 1 calc . . R
C12 C 0.8148(6) 0.2214(4) 1.3263(3) 0.0285(11) Uani 1 d . . .
O6 O 0.7433(5) -0.1182(3) 1.0371(2) 0.0359(9) Uani 1 d . . .
N4 N 0.7180(5) -0.3107(3) 1.1009(2) 0.0285(9) Uani 1 d . . .
C13 C 0.7369(6) -0.2215(4) 1.0308(3) 0.0284(11) Uani 1 d . . .
C14 C 0.7525(7) -0.2730(4) 0.9446(3) 0.0366(12) Uani 1 d . . .
H14A H 0.8893 -0.2865 0.9158 0.044 Uiso 1 calc . . R
H14B H 0.6658 -0.2188 0.9025 0.044 Uiso 1 calc . . R
C15 C 0.6851(7) -0.3919(4) 0.9753(3) 0.0386(13) Uani 1 d . . .
H15A H 0.5435 -0.3815 0.9701 0.046 Uiso 1 calc . . R
H15B H 0.7615 -0.4527 0.9403 0.046 Uiso 1 calc . . R
C16 C 0.7269(7) -0.4263(4) 1.0736(3) 0.0413(13) Uani 1 d . . .
H16A H 0.6262 -0.4661 1.1097 0.050 Uiso 1 calc . . R
H16B H 0.8582 -0.4792 1.0792 0.050 Uiso 1 calc . . R
C17 C 0.7346(7) -0.3012(4) 1.1928(3) 0.0381(13) Uani 1 d . . .
H17A H 0.8634 -0.3464 1.2094 0.057 Uiso 1 calc . . GR
H17B H 0.6310 -0.3329 1.2323 0.057 Uiso 1 calc . . GR
H17C H 0.7204 -0.2182 1.1976 0.057 Uiso 1 calc . . GR
O7 O 0.6975(5) -0.1850(3) 0.6417(2) 0.0475(10) Uani 1 d . . .
N5 N 0.6819(6) -0.3760(3) 0.6334(3) 0.0378(11) Uani 1 d . . .
C18 C 0.6954(6) -0.2633(4) 0.5970(3) 0.0338(12) Uani 1 d . . .
C19 C 0.7107(8) -0.2507(5) 0.4963(3) 0.0464(14) Uani 1 d . . .
H19A H 0.8408 -0.2364 0.4690 0.056 Uiso 1 calc . . R
H19B H 0.6072 -0.1845 0.4721 0.056 Uiso 1 calc . . R
C20 C 0.6826(10) -0.3699(5) 0.4787(4) 0.0661(18) Uani 1 d . . .
H20A H 0.5515 -0.3604 0.4592 0.079 Uiso 1 calc . . R
H20B H 0.7845 -0.4004 0.4326 0.079 Uiso 1 calc . . R
C21 C 0.7021(9) -0.4546(5) 0.5680(4) 0.0572(16) Uani 1 d . . .
H21A H 0.5973 -0.4999 0.5811 0.069 Uiso 1 calc . . R
H21B H 0.8316 -0.5106 0.5673 0.069 Uiso 1 calc . . R
C22 C 0.6763(8) -0.4201(5) 0.7292(3) 0.0542(16) Uani 1 d . . .
H22A H 0.6491 -0.3533 0.7612 0.081 Uiso 1 calc . . GR
H22B H 0.8034 -0.4717 0.7423 0.081 Uiso 1 calc . . GR
H22C H 0.5727 -0.4647 0.7477 0.081 Uiso 1 calc . . GR


_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 1.362(5) . ?
O2 C7 1.214(5) . ?
O3 C9 1.369(5) . ?
O3 C12 1.358(5) . ?
O4 N3 1.236(5) . ?
O5 N3 1.239(5) . ?
N1 H1A 0.8600 . ?
N1 N2 1.381(5) . ?
N1 C7 1.375(5) . ?
N2 C8 1.292(5) . ?
N3 C12 1.433(6) . ?
C1 C2 1.397(6) . ?
C1 C6 1.388(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(6) . ?
C4 C5 1.401(6) . ?
C4 C7 1.511(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.440(6) . ?
C9 C10 1.373(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.415(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.349(6) . ?
O6 C13 1.231(5) . ?
N4 C13 1.350(5) . ?
N4 C16 1.464(6) . ?
N4 C17 1.447(5) . ?
C13 C14 1.524(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.528(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.524(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O7 C18 1.239(6) . ?
N5 C18 1.337(6) . ?
N5 C21 1.445(6) . ?
N5 C22 1.446(6) . ?
C18 C19 1.502(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.519(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.518(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 . . ?
C12 O3 C9 104.7(3) . . ?
N2 N1 H1A 120.5 . . ?
C7 N1 H1A 120.5 . . ?
C7 N1 N2 118.9(4) . . ?
C8 N2 N1 114.5(4) . . ?
O4 N3 O5 124.5(4) . . ?
O4 N3 C12 118.8(4) . . ?
O5 N3 C12 116.7(4) . . ?
O1 C1 C2 122.4(4) . . ?
O1 C1 C6 118.7(4) . . ?
C6 C1 C2 118.9(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 C7 124.4(4) . . ?
C5 C4 C7 117.8(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 120.4(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O2 C7 N1 123.9(4) . . ?
O2 C7 C4 122.3(4) . . ?
N1 C7 C4 113.7(4) . . ?
N2 C8 H8 119.2 . . ?
N2 C8 C9 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
O3 C9 C8 119.4(4) . . ?
O3 C9 C10 110.3(4) . . ?
C10 C9 C8 130.4(4) . . ?
C9 C10 H10 126.5 . . ?
C9 C10 C11 106.9(4) . . ?
C11 C10 H10 126.5 . . ?
C10 C11 H11 127.6 . . ?
C12 C11 C10 104.8(4) . . ?
C12 C11 H11 127.6 . . ?
O3 C12 N3 116.3(4) . . ?
C11 C12 O3 113.3(4) . . ?
C11 C12 N3 130.4(4) . . ?
C13 N4 C16 113.4(4) . . ?
C13 N4 C17 123.1(4) . . ?
C17 N4 C16 122.1(3) . . ?
O6 C13 N4 125.2(4) . . ?
O6 C13 C14 127.2(4) . . ?
N4 C13 C14 107.6(4) . . ?
C13 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C13 C14 C15 104.6(4) . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 C14 103.5(4) . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
N4 C16 C15 103.8(3) . . ?
N4 C16 H16A 111.0 . . ?
N4 C16 H16B 111.0 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 N5 C21 113.9(4) . . ?
C18 N5 C22 123.1(4) . . ?
C21 N5 C22 122.4(4) . . ?
O7 C18 N5 123.7(5) . . ?
O7 C18 C19 127.3(4) . . ?
N5 C18 C19 109.0(4) . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
C18 C19 C20 105.0(4) . . ?
H19A C19 H19B 108.8 . . ?
C20 C19 H19A 110.8 . . ?
C20 C19 H19B 110.8 . . ?
C19 C20 H20A 110.7 . . ?
C19 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C21 C20 C19 105.4(5) . . ?
C21 C20 H20A 110.7 . . ?
C21 C20 H20B 110.7 . . ?
N5 C21 C20 104.4(4) . . ?
N5 C21 H21A 110.9 . . ?
N5 C21 H21B 110.9 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O1 H1 O7 0.82 1.82 2.632(4) 172.2 .
N1 H1A O6 0.86 2.11 2.929(4) 160.4 .
C2 H2 O7 0.93 2.46 3.116(6) 127.5 .
C3 H3 O6 0.93 2.47 3.358(5) 160.3 .
C8 H8 O6 0.93 2.38 3.205(6) 148.0 .
C11 H11 O1 0.93 2.36 3.264(5) 163.1 1_556

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.0(4) . . . . ?
O1 C1 C6 C5 -178.7(4) . . . . ?
O3 C9 C10 C11 -0.5(5) . . . . ?
O4 N3 C12 O3 0.1(6) . . . . ?
O4 N3 C12 C11 -178.3(5) . . . . ?
O5 N3 C12 O3 179.5(3) . . . . ?
O5 N3 C12 C11 1.1(7) . . . . ?
N1 N2 C8 C9 180.0(3) . . . . ?
N2 N1 C7 O2 0.2(6) . . . . ?
N2 N1 C7 C4 -178.7(3) . . . . ?
N2 C8 C9 O3 -0.3(6) . . . . ?
N2 C8 C9 C10 179.3(4) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C1 C6 C5 2.2(7) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C7 178.6(4) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C3 C4 C7 O2 -169.6(4) . . . . ?
C3 C4 C7 N1 9.3(6) . . . . ?
C4 C5 C6 C1 -1.4(7) . . . . ?
C5 C4 C7 O2 9.1(6) . . . . ?
C5 C4 C7 N1 -172.0(4) . . . . ?
C6 C1 C2 C3 -1.9(6) . . . . ?
C7 N1 N2 C8 -177.5(4) . . . . ?
C7 C4 C5 C6 -178.4(4) . . . . ?
C8 C9 C10 C11 179.9(4) . . . . ?
C9 O3 C12 N3 -178.8(3) . . . . ?
C9 O3 C12 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 O3 -0.2(5) . . . . ?
C10 C11 C12 N3 178.2(4) . . . . ?
C12 O3 C9 C8 -180.0(4) . . . . ?
C12 O3 C9 C10 0.4(5) . . . . ?
O6 C13 C14 C15 -166.6(4) . . . . ?
N4 C13 C14 C15 14.4(5) . . . . ?
C13 N4 C16 C15 -18.3(5) . . . . ?
C13 C14 C15 C16 -24.6(5) . . . . ?
C14 C15 C16 N4 25.7(5) . . . . ?
C16 N4 C13 O6 -176.5(4) . . . . ?
C16 N4 C13 C14 2.5(5) . . . . ?
C17 N4 C13 O6 -10.1(7) . . . . ?
C17 N4 C13 C14 168.8(4) . . . . ?
C17 N4 C16 C15 175.2(4) . . . . ?
O7 C18 C19 C20 -175.4(5) . . . . ?
N5 C18 C19 C20 5.7(5) . . . . ?
C18 N5 C21 C20 -13.1(6) . . . . ?
C18 C19 C20 C21 -13.1(6) . . . . ?
C19 C20 C21 N5 15.6(6) . . . . ?
C21 N5 C18 O7 -174.2(4) . . . . ?
C21 N5 C18 C19 4.8(6) . . . . ?
C22 N5 C18 O7 -2.6(7) . . . . ?
C22 N5 C18 C19 176.4(4) . . . . ?
C22 N5 C21 C20 175.2(4) . . . . ?

_olex2_date_sample_data_collection 2015-01-27
_olex2_submission_special_instructions 'No special instructions were received'
