# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_xnkd-01
_database_code_depnum_ccdc_archive 'CCDC 1435484'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
_audit_creation_date             2015-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C N4 O, C2 H4 N3'
_chemical_formula_sum            'C3 H5 N7 O'
_chemical_formula_weight         155.14
_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           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                   15.2410(12)
_cell_length_b                   10.5185(8)
_cell_length_c                   7.7546(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.767(8)
_cell_angle_gamma                90
_cell_volume                     1221.26(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1399
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.3750
_cell_measurement_theta_min      5.1560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3333
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         5.139
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_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   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   19.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00  109.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   90.00  175.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   91.00  176.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 14 omega   41.00  126.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  109.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000    0.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0903685000
_diffrn_orient_matrix_UB_12      -0.0689587000
_diffrn_orient_matrix_UB_13      0.0487491000
_diffrn_orient_matrix_UB_21      -0.0366472000
_diffrn_orient_matrix_UB_22      -0.1109085000
_diffrn_orient_matrix_UB_23      -0.1222947000
_diffrn_orient_matrix_UB_31      0.0326820000
_diffrn_orient_matrix_UB_32      0.0664330000
_diffrn_orient_matrix_UB_33      -0.1534703000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                947
_reflns_number_total             1093
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.039
_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)+(0.0910P)²+0.0810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B)
;
_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
O001 O 0.38603(8) 0.15503(12) 0.60408(18) 0.0490(4) Uani 1 1 d . . . . .
N002 N 0.46001(9) 0.16114(13) 0.53880(19) 0.0374(4) Uani 1 1 d . . . . .
N003 N 0.22659(9) 0.48603(14) 0.79069(19) 0.0411(4) Uani 1 1 d . . . . .
N004 N 0.32017(11) 0.36936(14) 0.6959(2) 0.0431(4) Uani 1 1 d . . . . .
N005 N 0.57799(10) 0.11814(15) 0.4341(2) 0.0439(5) Uani 1 1 d . . . . .
N006 N 0.49712(11) 0.27213(15) 0.5100(2) 0.0469(4) Uani 1 1 d . . . . .
N007 N 0.56813(11) 0.24424(16) 0.4463(2) 0.0497(5) Uani 1 1 d . . . . .
N008 N 0.28916(10) 0.56678(15) 0.7516(2) 0.0492(5) Uani 1 1 d . . . . .
C009 C 0.50961(10) 0.06647(16) 0.4930(2) 0.0354(4) Uani 1 1 d . . . . .
C00A C 0.24483(13) 0.36912(16) 0.7579(2) 0.0417(5) Uani 1 1 d . . . . .
H00A H 0.2112 0.2980 0.7747 0.050 Uiso 1 1 calc R . . . .
C00B C 0.34531(13) 0.49195(17) 0.6943(3) 0.0463(5) Uani 1 1 d . . . . .
H00B H 0.3966 0.5198 0.6568 0.056 Uiso 1 1 calc R . . . .
H003 H 0.1793(16) 0.521(2) 0.837(3) 0.071(7) Uiso 1 1 d . . . . .
H004 H 0.3524(19) 0.295(3) 0.649(3) 0.093(8) 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
O001 N002 1.3209(17) . ?
N002 N006 1.334(2) . ?
N002 C009 1.338(2) . ?
N003 N008 1.3531(19) . ?
N003 C00A 1.296(2) . ?
N003 H003 0.94(2) . ?
N004 C00A 1.325(3) . ?
N004 C00B 1.346(2) . ?
N004 H004 1.03(3) . ?
N005 N007 1.340(2) . ?
N005 C009 1.330(2) . ?
N006 N007 1.304(2) . ?
N008 C00B 1.300(2) . ?
C009 C009 1.437(3) 5_656 ?
C00A H00A 0.9300 . ?
C00B H00B 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
O001 N002 N006 121.72(13) . . ?
O001 N002 C009 129.10(14) . . ?
N006 N002 C009 109.18(14) . . ?
N008 N003 H003 117.6(14) . . ?
C00A N003 N008 111.43(14) . . ?
C00A N003 H003 131.0(14) . . ?
C00A N004 C00B 105.81(14) . . ?
C00A N004 H004 129.0(17) . . ?
C00B N004 H004 125.0(16) . . ?
C009 N005 N007 105.95(14) . . ?
N007 N006 N002 105.93(14) . . ?
N006 N007 N005 111.18(15) . . ?
C00B N008 N003 103.47(15) . . ?
N002 C009 C009 124.83(18) . 5_656 ?
N005 C009 N002 107.76(15) . . ?
N005 C009 C009 127.41(19) . 5_656 ?
N003 C00A N004 107.55(15) . . ?
N003 C00A H00A 126.2 . . ?
N004 C00A H00A 126.2 . . ?
N004 C00B H00B 124.1 . . ?
N008 C00B N004 111.73(16) . . ?
N008 C00B H00B 124.1 . . ?

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
O001 N002 N006 N007 179.93(16) . . . . ?
O001 N002 C009 N005 -179.87(17) . . . . ?
O001 N002 C009 C009 0.1(3) . . . 5_656 ?
N002 N006 N007 N005 -0.3(2) . . . . ?
N003 N008 C00B N004 0.2(2) . . . . ?
N006 N002 C009 N005 -0.4(2) . . . . ?
N006 N002 C009 C009 179.6(2) . . . 5_656 ?
N007 N005 C009 N002 0.2(2) . . . . ?
N007 N005 C009 C009 -179.8(2) . . . 5_656 ?
N008 N003 C00A N004 0.0(2) . . . . ?
C009 N002 N006 N007 0.4(2) . . . . ?
C009 N005 N007 N006 0.0(2) . . . . ?
C00A N003 N008 C00B -0.1(2) . . . . ?
C00A N004 C00B N008 -0.2(2) . . . . ?
C00B N004 C00A N003 0.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-17
_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_m20151011e1
_database_code_depnum_ccdc_archive 'CCDC 1435485'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 N12 O4'
_chemical_formula_weight         370.36

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3860(5)
_cell_length_b                   7.2676(6)
_cell_length_c                   11.1149(11)
_cell_angle_alpha                106.362(7)
_cell_angle_beta                 92.344(13)
_cell_angle_gamma                104.613(9)
_cell_volume                     401.00(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1514
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5154
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1800
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0535P)²+0.1021P] 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         1800
_refine_ls_number_parameters     133
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_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
O1 O 0.09250(15) 0.05967(11) 0.74367(6) 0.01864(19) Uani 1 1 d . . .
N1 N 0.20931(16) 0.11557(12) 0.65356(8) 0.0145(2) Uani 1 1 d . . .
N2 N 0.44886(17) 0.24095(13) 0.67490(8) 0.0182(2) Uani 1 1 d . . .
N3 N 0.50783(17) 0.26492(14) 0.56561(8) 0.0195(2) Uani 1 1 d . . .
N4 N 0.31184(17) 0.15857(13) 0.47391(8) 0.0173(2) Uani 1 1 d . . .
N5 N 0.33216(17) 0.66448(13) 0.88483(8) 0.0173(2) Uani 1 1 d D . .
H5 H 0.188(2) 0.5953(18) 0.9076(13) 0.021 Uiso 1 1 d D . .
N6 N 0.58725(17) 0.78787(13) 0.76598(8) 0.0166(2) Uani 1 1 d D . .
H6 H 0.638(3) 0.817(2) 0.6968(10) 0.020 Uiso 1 1 d D . .
C1 C 0.12482(19) 0.06534(14) 0.52944(9) 0.0140(2) Uani 1 1 d . . .
C2 C 0.7288(2) 0.83776(17) 0.88268(10) 0.0206(2) Uani 1 1 d . . .
H2 H 0.9051 0.9120 0.9059 0.025 Uiso 1 1 calc R . .
C3 C 0.5684(2) 0.76085(17) 0.95756(10) 0.0203(2) Uani 1 1 d . . .
H3 H 0.6101 0.7711 1.0435 0.024 Uiso 1 1 calc R . .
C4 C 0.34821(19) 0.68146(14) 0.76860(9) 0.0153(2) Uani 1 1 d . . .
C5 C 0.1403(2) 0.59788(16) 0.66071(10) 0.0190(2) Uani 1 1 d . . .
H5A H 0.0531 0.6995 0.6567 0.029 Uiso 1 1 calc R . .
H5B H 0.0150 0.4820 0.6721 0.029 Uiso 1 1 calc R . .
H5C H 0.2154 0.5568 0.5820 0.029 Uiso 1 1 calc R . .
O2 O 0.11764(15) 0.64847(11) 0.12804(7) 0.01974(19) Uani 1 1 d D . .
H2A H 0.254(2) 0.659(2) 0.1784(13) 0.041(4) Uiso 1 1 d D . .
H2B H 0.045(3) 0.742(2) 0.1653(14) 0.047(5) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3099(11) . ?
N1 N2 1.3458(13) . ?
N1 C1 1.3507(12) . ?
N2 N3 1.3152(12) . ?
N3 N4 1.3443(12) . ?
N4 C1 1.3405(13) . ?
N5 C4 1.3361(13) . ?
N5 C3 1.3823(14) . ?
N5 H5 0.899(9) . ?
N6 C4 1.3303(14) . ?
N6 C2 1.3820(13) . ?
N6 H6 0.890(8) . ?
C1 C1 1.4393(19) 2_556 ?
C2 C3 1.3522(15) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.4823(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O2 H2A 0.877(9) . ?
O2 H2B 0.877(9) . ?

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
O1 N1 N2 122.38(8) . . ?
O1 N1 C1 129.41(9) . . ?
N2 N1 C1 108.20(8) . . ?
N3 N2 N1 106.81(8) . . ?
N2 N3 N4 110.63(8) . . ?
C1 N4 N3 106.29(8) . . ?
C4 N5 C3 109.34(9) . . ?
C4 N5 H5 123.0(9) . . ?
C3 N5 H5 127.6(9) . . ?
C4 N6 C2 109.40(9) . . ?
C4 N6 H6 122.1(9) . . ?
C2 N6 H6 128.5(9) . . ?
N4 C1 N1 108.07(9) . . ?
N4 C1 C1 127.32(11) . 2_556 ?
N1 C1 C1 124.61(11) . 2_556 ?
C3 C2 N6 106.92(9) . . ?
C3 C2 H2 126.5 . . ?
N6 C2 H2 126.5 . . ?
C2 C3 N5 106.71(9) . . ?
C2 C3 H3 126.6 . . ?
N5 C3 H3 126.6 . . ?
N6 C4 N5 107.62(9) . . ?
N6 C4 C5 125.41(9) . . ?
N5 C4 C5 126.98(9) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H2A O2 H2B 108.1(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 N3 179.73(8) . . . . ?
C1 N1 N2 N3 -0.29(11) . . . . ?
N1 N2 N3 N4 0.21(11) . . . . ?
N2 N3 N4 C1 -0.04(11) . . . . ?
N3 N4 C1 N1 -0.14(11) . . . . ?
N3 N4 C1 C1 179.53(12) . . . 2_556 ?
O1 N1 C1 N4 -179.75(9) . . . . ?
N2 N1 C1 N4 0.27(11) . . . . ?
O1 N1 C1 C1 0.57(18) . . . 2_556 ?
N2 N1 C1 C1 -179.41(11) . . . 2_556 ?
C4 N6 C2 C3 -0.75(12) . . . . ?
N6 C2 C3 N5 0.31(12) . . . . ?
C4 N5 C3 C2 0.23(12) . . . . ?
C2 N6 C4 N5 0.89(12) . . . . ?
C2 N6 C4 C5 -178.99(10) . . . . ?
C3 N5 C4 N6 -0.70(11) . . . . ?
C3 N5 C4 C5 179.18(10) . . . . ?

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
O2 H2A N2 0.877(9) 2.071(10) 2.9220(12) 163.5(14) 2_666
N6 H6 N4 0.890(8) 1.978(9) 2.8553(12) 168.6(13) 2_666
N5 H5 O2 0.899(9) 2.432(12) 3.0035(12) 121.7(11) 1_556
N6 H6 O1 0.890(8) 2.562(13) 2.9980(12) 111.0(10) 1_665
N5 H5 O2 0.899(9) 2.022(10) 2.8409(12) 150.7(12) 2_566
O2 H2B O1 0.877(9) 1.855(9) 2.7300(11) 175.3(15) 2_566
O2 H2B N1 0.877(9) 2.604(12) 3.3857(12) 149.0(15) 2_566

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_m20151025d1
_database_code_depnum_ccdc_archive 'CCDC 1435486'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 N10 O2'
_chemical_formula_weight         238.20

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   10.042(2)
_cell_length_b                   13.882(2)
_cell_length_c                   6.7012(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.155(4)
_cell_angle_gamma                90.00
_cell_volume                     924.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2433
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11618
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2122
_reflns_number_gt                1974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0825P)²+0.2533P] 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         2122
_refine_ls_number_parameters     163
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.47075(9) 0.40991(6) 0.71561(14) 0.0220(2) Uani 1 1 d . . .
O2 O 0.51397(9) 0.76194(6) 0.98619(14) 0.0224(2) Uani 1 1 d D . .
H2 H 0.5038(17) 0.8134(9) 0.914(2) 0.027 Uiso 1 1 d D . .
N1 N 0.56307(10) 0.47911(7) 0.73116(15) 0.0185(2) Uani 1 1 d . . .
N2 N 0.68949(10) 0.46314(8) 0.69861(17) 0.0225(3) Uani 1 1 d . . .
N3 N 0.75344(11) 0.54521(8) 0.73375(17) 0.0237(3) Uani 1 1 d . . .
N4 N 0.67023(10) 0.61343(7) 0.78901(16) 0.0213(3) Uani 1 1 d . . .
N5 N 0.41441(10) 0.70045(7) 0.91310(16) 0.0191(2) Uani 1 1 d . . .
N6 N 0.28673(11) 0.71540(8) 0.93906(17) 0.0231(3) Uani 1 1 d . . .
N7 N 0.22167(11) 0.63844(8) 0.86992(18) 0.0246(3) Uani 1 1 d . . .
N8 N 0.30605(10) 0.57304(7) 0.80342(17) 0.0214(3) Uani 1 1 d . . .
N9 N 0.19820(11) 0.38219(7) 0.71962(17) 0.0224(3) Uani 1 1 d D . .
H9 H 0.2798(11) 0.4094(12) 0.738(3) 0.027 Uiso 1 1 d D . .
N10 N 0.18438(11) 0.28665(7) 0.69162(17) 0.0224(3) Uani 1 1 d D . .
H10 H 0.2557(13) 0.2478(11) 0.699(3) 0.027 Uiso 1 1 d D . .
C1 C 0.55088(12) 0.57141(8) 0.78674(17) 0.0181(3) Uani 1 1 d . . .
C2 C 0.42689(12) 0.61303(8) 0.83162(18) 0.0184(3) Uani 1 1 d . . .
C3 C 0.07634(13) 0.42132(9) 0.7101(2) 0.0263(3) Uani 1 1 d . . .
H3 H 0.0579 0.4879 0.7247 0.032 Uiso 1 1 calc R . .
C4 C -0.01901(14) 0.34901(10) 0.6754(2) 0.0290(3) Uani 1 1 d . . .
H4 H -0.1140 0.3557 0.6613 0.035 Uiso 1 1 calc R . .
C5 C 0.05366(13) 0.26473(9) 0.6655(2) 0.0265(3) Uani 1 1 d . . .
H5 H 0.0167 0.2020 0.6439 0.032 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 N1 1.3288(12) . ?
O2 N5 1.3526(13) . ?
O2 H2 0.860(9) . ?
N1 N2 1.3368(15) . ?
N1 C1 1.3448(14) . ?
N2 N3 1.3126(15) . ?
N3 N4 1.3492(15) . ?
N4 C1 1.3311(15) . ?
N5 N6 1.3344(15) . ?
N5 C2 1.3438(15) . ?
N6 N7 1.3027(15) . ?
N7 N8 1.3594(15) . ?
N8 C2 1.3235(16) . ?
N9 C3 1.3322(17) . ?
N9 N10 1.3439(14) . ?
N9 H9 0.895(9) . ?
N10 C5 1.3347(17) . ?
N10 H10 0.892(9) . ?
C1 C2 1.4426(17) . ?
C3 C4 1.3840(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3854(18) . ?
C4 H4 0.9500 . ?
C5 H5 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
N5 O2 H2 107.4(12) . . ?
O1 N1 N2 122.38(9) . . ?
O1 N1 C1 128.36(10) . . ?
N2 N1 C1 109.21(10) . . ?
N3 N2 N1 106.18(10) . . ?
N2 N3 N4 110.62(10) . . ?
C1 N4 N3 106.32(10) . . ?
N6 N5 C2 109.89(10) . . ?
N6 N5 O2 121.96(10) . . ?
C2 N5 O2 127.61(10) . . ?
N7 N6 N5 105.59(10) . . ?
N6 N7 N8 111.09(10) . . ?
C2 N8 N7 105.94(10) . . ?
C3 N9 N10 108.65(10) . . ?
C3 N9 H9 130.6(11) . . ?
N10 N9 H9 120.7(11) . . ?
C5 N10 N9 108.87(10) . . ?
C5 N10 H10 129.5(11) . . ?
N9 N10 H10 121.5(11) . . ?
N4 C1 N1 107.67(10) . . ?
N4 C1 C2 128.64(11) . . ?
N1 C1 C2 123.68(11) . . ?
N8 C2 N5 107.47(10) . . ?
N8 C2 C1 127.11(11) . . ?
N5 C2 C1 125.41(11) . . ?
N9 C3 C4 108.74(11) . . ?
N9 C3 H3 125.6 . . ?
C4 C3 H3 125.6 . . ?
C3 C4 C5 105.31(12) . . ?
C3 C4 H4 127.3 . . ?
C5 C4 H4 127.3 . . ?
N10 C5 C4 108.43(11) . . ?
N10 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?

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 N1 N2 N3 -177.78(10) . . . . ?
C1 N1 N2 N3 -0.14(13) . . . . ?
N1 N2 N3 N4 0.23(13) . . . . ?
N2 N3 N4 C1 -0.23(13) . . . . ?
C2 N5 N6 N7 -1.29(13) . . . . ?
O2 N5 N6 N7 -173.41(10) . . . . ?
N5 N6 N7 N8 1.27(14) . . . . ?
N6 N7 N8 C2 -0.79(14) . . . . ?
C3 N9 N10 C5 -0.40(15) . . . . ?
N3 N4 C1 N1 0.13(13) . . . . ?
N3 N4 C1 C2 -179.22(12) . . . . ?
O1 N1 C1 N4 177.46(10) . . . . ?
N2 N1 C1 N4 0.00(13) . . . . ?
O1 N1 C1 C2 -3.15(19) . . . . ?
N2 N1 C1 C2 179.39(11) . . . . ?
N7 N8 C2 N5 -0.04(13) . . . . ?
N7 N8 C2 C1 179.24(12) . . . . ?
N6 N5 C2 N8 0.83(13) . . . . ?
O2 N5 C2 N8 172.38(11) . . . . ?
N6 N5 C2 C1 -178.47(11) . . . . ?
O2 N5 C2 C1 -6.92(19) . . . . ?
N4 C1 C2 N8 170.65(12) . . . . ?
N1 C1 C2 N8 -8.6(2) . . . . ?
N4 C1 C2 N5 -10.2(2) . . . . ?
N1 C1 C2 N5 170.56(11) . . . . ?
N10 N9 C3 C4 0.14(16) . . . . ?
N9 C3 C4 C5 0.16(17) . . . . ?
N9 N10 C5 C4 0.51(16) . . . . ?
C3 C4 C5 N10 -0.41(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.860(9) 1.637(10) 2.4760(12) 164.4(17) 2_656
O2 H2 N1 0.860(9) 2.551(10) 3.3895(14) 165.3(15) 2_656
N9 H9 O1 0.895(9) 1.945(11) 2.7679(15) 152.2(16) .
N9 H9 N8 0.895(9) 2.321(16) 2.8871(15) 121.1(14) .
N10 H10 N4 0.892(9) 2.005(12) 2.8065(15) 148.7(15) 2_646

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1441695'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H18 N16 O6'
_chemical_formula_weight         410.36

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   3.5356(14)
_cell_length_b                   13.300(5)
_cell_length_c                   18.164(7)
_cell_angle_alpha                72.222(4)
_cell_angle_beta                 87.207(4)
_cell_angle_gamma                86.316(4)
_cell_volume                     811.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6292
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5081
_reflns_number_gt                4844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1170P)²+4.9911P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         5081
_refine_ls_number_parameters     506
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0910
_refine_ls_wR_factor_ref         0.2425
_refine_ls_wR_factor_gt          0.2400
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
O1 O 0.4831(11) 0.4888(3) 0.1633(2) 0.0210(9) Uani 1 1 d . . .
O1W O 0.756(3) -0.0711(8) 0.1034(7) 0.124(4) Uani 1 1 d . . .
H1WD H 0.6311 -0.0373 0.1383 0.148 Uiso 1 1 d R . .
H1WA H 0.5814 -0.1137 0.0890 0.185 Uiso 1 1 d R . .
O2 O 1.0765(11) 0.4536(3) 0.4297(2) 0.0215(9) Uani 1 1 d . . .
O2W O 1.267(4) -0.0101(5) 1.0054(4) 0.112(4) Uani 1 1 d . . .
H2WD H 1.0549 0.0350 0.9821 0.134 Uiso 1 1 d R . .
H2WB H 1.3845 -0.0430 0.9692 0.168 Uiso 1 1 d R . .
O3 O 0.6338(11) 0.4404(3) 0.6773(2) 0.0192(9) Uani 1 1 d . . .
O3W O -0.307(8) 0.9881(10) 0.5155(7) 0.230(11) Uani 1 1 d . . .
H3WD H -0.1617 0.9518 0.4845 0.276 Uiso 1 1 d R . .
H3WA H -0.5186 1.0272 0.4868 0.345 Uiso 1 1 d R . .
O4 O -0.0673(12) 0.4339(3) 0.9425(2) 0.0220(10) Uani 1 1 d . . .
O4W O 0.168(4) 0.9030(9) 0.5996(5) 0.145(5) Uani 1 1 d . . .
H4WB H -0.0888 0.9052 0.6192 0.217 Uiso 1 1 d R . .
H4WC H 0.3098 0.8451 0.6339 0.217 Uiso 1 1 d R . .
O5 O 0.3440(13) 0.0413(3) 0.2180(2) 0.0252(10) Uani 1 1 d . . .
O6 O 0.1715(11) 0.8691(3) 0.4123(2) 0.0188(9) Uani 1 1 d . . .
O7 O 0.5896(13) 0.0332(3) 0.6984(2) 0.0249(10) Uani 1 1 d . . .
O8 O 0.0089(13) 0.8866(3) 0.8809(2) 0.0256(10) Uani 1 1 d . . .
N1 N 0.6040(14) 0.5514(3) 0.1991(3) 0.0163(11) Uani 1 1 d . . .
N2 N 0.6074(14) 0.6558(4) 0.1682(3) 0.0196(11) Uani 1 1 d . . .
N3 N 0.7365(15) 0.6937(4) 0.2198(3) 0.0216(11) Uani 1 1 d . . .
N4 N 0.8247(14) 0.6144(4) 0.2845(3) 0.0197(11) Uani 1 1 d . . .
N5 N 0.9365(13) 0.3931(3) 0.3931(3) 0.0146(7) Uani 1 1 d U . .
N6 N 0.9337(15) 0.2878(4) 0.4247(3) 0.0234(12) Uani 1 1 d . . .
N7 N 0.7931(16) 0.2506(4) 0.3736(3) 0.0238(12) Uani 1 1 d . . .
N8 N 0.7030(14) 0.3299(4) 0.3091(3) 0.0175(11) Uani 1 1 d . . .
N9 N 0.5163(14) 0.5059(3) 0.7166(3) 0.0177(11) Uani 1 1 d . . .
N10 N 0.5763(15) 0.6093(4) 0.6895(3) 0.0201(11) Uani 1 1 d . . .
N11 N 0.4351(14) 0.6524(4) 0.7415(3) 0.0198(11) Uani 1 1 d . . .
N12 N 0.2960(14) 0.5794(4) 0.8029(3) 0.0211(12) Uani 1 1 d . . .
N13 N 0.0683(13) 0.3681(3) 0.9062(2) 0.0146(10) Uani 1 1 d . . .
N14 N 0.0366(15) 0.2628(4) 0.9376(3) 0.0197(11) Uani 1 1 d . . .
N15 N 0.1972(15) 0.2169(4) 0.8877(3) 0.0218(12) Uani 1 1 d . . .
N16 N 0.3271(14) 0.2911(4) 0.8245(3) 0.0199(11) Uani 1 1 d . . .
N17 N 0.4422(17) 0.0805(4) 0.3288(3) 0.0251(12) Uani 1 1 d . . .
H17A H 0.3748 0.0187 0.3594 0.030 Uiso 1 1 calc R . .
H17B H 0.5133 0.1286 0.3486 0.030 Uiso 1 1 calc R . .
N18 N 0.5580(14) 0.2025(4) 0.2111(3) 0.0168(11) Uani 1 1 d . . .
H18A H 0.5690 0.2490 0.2365 0.020 Uiso 1 1 calc R . .
N19 N 0.7745(14) 0.3299(4) 0.1050(3) 0.0185(11) Uani 1 1 d . . .
H19A H 0.8501 0.3536 0.0562 0.022 Uiso 1 1 calc R . .
H19B H 0.7749 0.3710 0.1348 0.022 Uiso 1 1 calc R . .
N20 N 0.6556(15) 0.1696(4) 0.0917(3) 0.0202(11) Uani 1 1 d . . .
H20A H 0.7294 0.1909 0.0426 0.024 Uiso 1 1 calc R . .
H20B H 0.5781 0.1051 0.1124 0.024 Uiso 1 1 calc R . .
N21 N 0.0978(15) 0.8368(4) 0.2980(3) 0.0207(11) Uani 1 1 d . . .
H21A H 0.1745 0.8991 0.2703 0.025 Uiso 1 1 calc R . .
H21B H 0.0308 0.7917 0.2748 0.025 Uiso 1 1 calc R . .
N22 N -0.0324(13) 0.7081(3) 0.4122(3) 0.0149(10) Uani 1 1 d . . .
H22A H -0.0498 0.6660 0.3836 0.018 Uiso 1 1 calc R . .
N23 N -0.2508(14) 0.5740(4) 0.5142(3) 0.0188(11) Uani 1 1 d . . .
H23A H -0.3124 0.5466 0.5635 0.023 Uiso 1 1 calc R . .
H23B H -0.2775 0.5378 0.4817 0.023 Uiso 1 1 calc R . .
N24 N -0.0764(14) 0.7244(4) 0.5361(3) 0.0198(11) Uani 1 1 d . . .
H24A H -0.1362 0.6986 0.5856 0.024 Uiso 1 1 calc R . .
H24B H 0.0125 0.7879 0.5180 0.024 Uiso 1 1 calc R . .
N25 N 0.7491(15) 0.0931(4) 0.7950(3) 0.0217(12) Uani 1 1 d . . .
H25A H 0.8312 0.0303 0.8239 0.026 Uiso 1 1 calc R . .
H25B H 0.7578 0.1484 0.8117 0.026 Uiso 1 1 calc R . .
N26 N 0.5051(14) 0.2101(4) 0.6862(3) 0.0177(11) Uani 1 1 d . . .
H26A H 0.5289 0.2583 0.7095 0.021 Uiso 1 1 calc R . .
N27 N 0.2791(15) 0.3442(3) 0.5847(3) 0.0177(11) Uani 1 1 d . . .
H27A H 0.1900 0.3697 0.5379 0.021 Uiso 1 1 calc R . .
H27B H 0.3102 0.3868 0.6125 0.021 Uiso 1 1 calc R . .
N28 N 0.3229(15) 0.1766(4) 0.5736(3) 0.0222(12) Uani 1 1 d . . .
H28A H 0.2345 0.1997 0.5266 0.027 Uiso 1 1 calc R . .
H28B H 0.3835 0.1089 0.5943 0.027 Uiso 1 1 calc R . .
N29 N -0.1793(16) 0.8197(4) 0.7895(3) 0.0241(12) Uani 1 1 d . . .
H29A H -0.2464 0.8821 0.7577 0.029 Uiso 1 1 calc R . .
H29B H -0.2058 0.7622 0.7763 0.029 Uiso 1 1 calc R . .
N30 N 0.0597(14) 0.7088(4) 0.9012(3) 0.0182(11) Uani 1 1 d . . .
H30A H 0.0319 0.6587 0.8799 0.022 Uiso 1 1 calc R . .
N31 N 0.2666(15) 0.5756(4) 1.0073(3) 0.0196(11) Uani 1 1 d . . .
H31A H 0.3557 0.5530 1.0542 0.023 Uiso 1 1 calc R . .
H31B H 0.2255 0.5301 0.9825 0.023 Uiso 1 1 calc R . .
N32 N 0.2534(15) 0.7467(4) 1.0095(3) 0.0210(11) Uani 1 1 d . . .
H32A H 0.3424 0.7248 1.0565 0.025 Uiso 1 1 calc R . .
H32B H 0.2048 0.8147 0.9870 0.025 Uiso 1 1 calc R . .
C1 C 0.7399(16) 0.5256(4) 0.2709(3) 0.0160(12) Uani 1 1 d . . .
C2 C 0.7924(17) 0.4181(4) 0.3231(3) 0.0159(12) Uani 1 1 d . . .
C3 C 0.3456(16) 0.4867(4) 0.7865(3) 0.0199(13) Uani 1 1 d . . .
C4 C 0.2472(17) 0.3836(4) 0.8376(3) 0.0180(12) Uani 1 1 d . . .
C5 C 0.4364(17) 0.1012(4) 0.2520(3) 0.0173(13) Uani 1 1 d . . .
C6 C 0.6612(16) 0.2330(4) 0.1333(3) 0.0154(12) Uani 1 1 d . . .
C7 C 0.0829(16) 0.8107(4) 0.3748(3) 0.0168(13) Uani 1 1 d . . .
C8 C -0.1198(15) 0.6683(4) 0.4893(3) 0.0158(12) Uani 1 1 d . . .
C9 C 0.6142(15) 0.1044(4) 0.7270(3) 0.0142(12) Uani 1 1 d . . .
C10 C 0.3647(15) 0.2436(4) 0.6130(3) 0.0164(13) Uani 1 1 d . . .
C11 C -0.0381(16) 0.8123(4) 0.8576(3) 0.0187(13) Uani 1 1 d . . .
C12 C 0.1939(16) 0.6791(4) 0.9736(3) 0.0167(13) 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
O1 N1 1.304(6) . ?
O2 N5 1.320(6) . ?
O3 N9 1.321(6) . ?
O4 N13 1.303(6) . ?
O5 C5 1.215(7) . ?
O6 C7 1.241(7) . ?
O7 C9 1.221(7) . ?
O8 C11 1.211(7) . ?
N1 N2 1.330(6) . ?
N1 C1 1.348(7) . ?
N2 N3 1.303(7) . ?
N3 N4 1.352(7) . ?
N4 C1 1.334(8) . ?
N5 C2 1.331(7) . ?
N5 N6 1.343(6) . ?
N6 N7 1.307(7) . ?
N7 N8 1.351(6) . ?
N8 C2 1.333(8) . ?
N9 C3 1.338(7) . ?
N9 N10 1.338(6) . ?
N10 N11 1.311(7) . ?
N11 N12 1.332(7) . ?
N12 C3 1.354(8) . ?
N13 C4 1.334(7) . ?
N13 N14 1.351(6) . ?
N14 N15 1.326(7) . ?
N15 N16 1.348(7) . ?
N16 C4 1.334(8) . ?
N17 C5 1.337(7) . ?
N18 C6 1.384(7) . ?
N18 C5 1.409(7) . ?
N19 C6 1.314(7) . ?
N20 C6 1.295(8) . ?
N21 C7 1.331(7) . ?
N22 C8 1.364(7) . ?
N22 C7 1.402(7) . ?
N23 C8 1.303(7) . ?
N24 C8 1.311(8) . ?
N25 C9 1.307(8) . ?
N26 C10 1.374(7) . ?
N26 C9 1.413(7) . ?
N27 C10 1.300(7) . ?
N28 C10 1.320(8) . ?
N29 C11 1.329(8) . ?
N30 C12 1.353(8) . ?
N30 C11 1.393(7) . ?
N31 C12 1.338(7) . ?
N32 C12 1.294(8) . ?
C1 C2 1.460(7) . ?
C3 C4 1.454(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
O1 N1 N2 123.5(4) . . ?
O1 N1 C1 128.3(4) . . ?
N2 N1 C1 108.2(5) . . ?
N3 N2 N1 107.5(4) . . ?
N2 N3 N4 110.3(4) . . ?
C1 N4 N3 105.8(5) . . ?
O2 N5 C2 130.4(4) . . ?
O2 N5 N6 121.4(4) . . ?
C2 N5 N6 108.2(5) . . ?
N7 N6 N5 106.7(4) . . ?
N6 N7 N8 110.6(5) . . ?
C2 N8 N7 105.4(5) . . ?
O3 N9 C3 130.3(4) . . ?
O3 N9 N10 121.3(4) . . ?
C3 N9 N10 108.3(5) . . ?
N11 N10 N9 107.0(4) . . ?
N10 N11 N12 110.9(5) . . ?
N11 N12 C3 105.8(5) . . ?
O4 N13 C4 131.7(4) . . ?
O4 N13 N14 121.0(4) . . ?
C4 N13 N14 107.3(4) . . ?
N15 N14 N13 107.2(4) . . ?
N14 N15 N16 109.8(4) . . ?
C4 N16 N15 105.9(5) . . ?
C6 N18 C5 123.6(5) . . ?
C8 N22 C7 125.5(5) . . ?
C10 N26 C9 125.2(5) . . ?
C12 N30 C11 125.4(5) . . ?
N4 C1 N1 108.2(5) . . ?
N4 C1 C2 126.7(5) . . ?
N1 C1 C2 125.1(5) . . ?
N5 C2 N8 109.1(5) . . ?
N5 C2 C1 124.8(5) . . ?
N8 C2 C1 126.1(5) . . ?
N9 C3 N12 108.0(5) . . ?
N9 C3 C4 126.1(5) . . ?
N12 C3 C4 125.9(5) . . ?
N16 C4 N13 109.8(5) . . ?
N16 C4 C3 126.0(5) . . ?
N13 C4 C3 124.2(5) . . ?
O5 C5 N17 126.0(5) . . ?
O5 C5 N18 120.9(5) . . ?
N17 C5 N18 113.1(5) . . ?
N20 C6 N19 122.2(5) . . ?
N20 C6 N18 122.4(5) . . ?
N19 C6 N18 115.4(5) . . ?
O6 C7 N21 124.5(5) . . ?
O6 C7 N22 121.0(5) . . ?
N21 C7 N22 114.5(5) . . ?
N23 C8 N24 121.6(5) . . ?
N23 C8 N22 118.0(5) . . ?
N24 C8 N22 120.4(5) . . ?
O7 C9 N25 125.2(5) . . ?
O7 C9 N26 121.2(5) . . ?
N25 C9 N26 113.6(5) . . ?
N27 C10 N28 122.2(5) . . ?
N27 C10 N26 116.5(5) . . ?
N28 C10 N26 121.3(5) . . ?
O8 C11 N29 124.9(5) . . ?
O8 C11 N30 121.7(5) . . ?
N29 C11 N30 113.4(5) . . ?
N32 C12 N31 120.5(5) . . ?
N32 C12 N30 122.3(5) . . ?
N31 C12 N30 117.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.132
####################################################################### 
# 
# 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_xnkd-1104-7
_database_code_depnum_ccdc_archive 'CCDC 1444741'
_audit_update_record             
;
2015-12-30 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-16
_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         '5(C2 N8 O2), 10(C2 H5 N4), 7(H2 O)'
_chemical_formula_sum            'C30 H63 N80 O17'
_chemical_formula_weight         1816.60
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.0634(3)
_cell_length_b                   11.83085(18)
_cell_length_c                   32.1874(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.3131(17)
_cell_angle_gamma                90
_cell_volume                     7228.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8771
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6080
_cell_measurement_theta_min      3.7110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             3756
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            39151
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.550
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_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   23.00   90.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   90.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega  -33.00   55.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega  -31.00   53.00   1.0000    5.1300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  176.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   90.00  175.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   91.00  166.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 16 omega   63.00   90.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   98.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 18 omega   56.00  146.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0322045000
_diffrn_orient_matrix_UB_12      -0.0466092000
_diffrn_orient_matrix_UB_13      -0.0386940000
_diffrn_orient_matrix_UB_21      -0.0723965000
_diffrn_orient_matrix_UB_22      -0.0480793000
_diffrn_orient_matrix_UB_23      -0.0165622000
_diffrn_orient_matrix_UB_31      -0.0177780000
_diffrn_orient_matrix_UB_32      0.1114813000
_diffrn_orient_matrix_UB_33      -0.0233053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7843
_reflns_number_total             12900
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.369
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1189
_refine_ls_number_reflns         12900
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.016
_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)+(0.0860P)²+6.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2054
_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
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O02P(H02U,H02V), O02T(H02W,H02X), O03B(H03B,H03E), O03E(H03H,H03I), O03H(H03J,
 H03K), O03I(H03L,H03M), O03J(H03N,H03O)
2.b Aromatic/amide H refined with riding coordinates:
 N00K(H00K), N00M(H00M), N00N(H00N), N00O(H00O), N00Q(H00Q), N00R(H00R),
 N00T(H00T), N00W(H00W), N00X(H00X), N00Y(H00Y), N00Z(H00Z), N011(H011),
 N012(H012), N016(H016), N018(H018), N019(H019), N01C(H01C), N01G(H01G),
 C035(H035), C037(H037), C038(H038), C03A(H03A), C03C(H03C), C03D(H03D),
 C03F(H03F), C03G(H03G)
2.c X=CH2 refined with riding coordinates:
 N028(H02G,H02H), N02A(H02O,H02P), N02B(H02M,H02N), N02D(H02A,H02B), N02E(H02K,
 H02L), N02F(H02E,H02F), N02G(H02C,H02D), N02H(H02S,H02T), N02J(H02Q,H02R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O001 O 0.12460(8) 0.95153(16) 0.25003(7) 0.0416(5) Uani 1 1 d . . . . .
O002 O 0.37387(8) 1.13504(15) 0.24567(7) 0.0406(5) Uani 1 1 d . . . . .
O003 O 0.97283(8) -0.60091(15) 0.34784(7) 0.0418(5) Uani 1 1 d . . . . .
O004 O 0.17387(8) 0.05947(15) 0.04989(7) 0.0411(5) Uani 1 1 d . . . . .
O005 O -0.07622(8) -0.12198(15) 0.05355(7) 0.0419(5) Uani 1 1 d . . . . .
O006 O 0.67237(8) -0.62259(15) 0.04666(7) 0.0399(5) Uani 1 1 d . . . . .
O007 O 0.72422(8) -0.41527(15) 0.35179(7) 0.0419(5) Uani 1 1 d . . . . .
O008 O 0.42370(8) -0.43775(15) 0.05135(7) 0.0422(5) Uani 1 1 d . . . . .
O009 O 0.22351(8) -0.09815(16) 0.35250(7) 0.0447(5) Uani 1 1 d . . . . .
O00A O 0.47371(8) 0.08133(16) 0.34858(7) 0.0444(5) Uani 1 1 d . . . . .
N00B N 0.10829(10) 0.09192(16) 0.04834(7) 0.0281(5) Uani 1 1 d . . . . .
N00C N 0.19091(9) 0.91909(17) 0.25143(7) 0.0283(5) Uani 1 1 d . . . . .
N00D N 0.30783(10) 1.16691(17) 0.24595(7) 0.0299(5) Uani 1 1 d . . . . .
N00E N 0.28965(9) -0.13087(18) 0.35319(7) 0.0304(5) Uani 1 1 d . . . . .
N00F N -0.01058(9) -0.15425(17) 0.05352(7) 0.0294(5) Uani 1 1 d . . . . .
N00G N 0.60561(9) -0.65437(16) 0.04638(7) 0.0271(5) Uani 1 1 d . . . . .
N00H N 0.49028(10) -0.40586(16) 0.05198(7) 0.0291(5) Uani 1 1 d . . . . .
N00I N 0.90671(9) -0.63154(17) 0.34739(7) 0.0288(5) Uani 1 1 d . . . . .
N00J N 0.75139(10) -0.80948(18) 0.05133(8) 0.0326(5) Uani 1 1 d . . . . .
N00K N 0.33858(10) 0.36394(17) 0.05066(7) 0.0310(5) Uani 1 1 d . . . . .
H00K H 0.3800 0.3913 0.0491 0.037 Uiso 1 1 calc R . . . .
N00L N 0.78986(10) -0.38407(17) 0.35205(7) 0.0299(5) Uani 1 1 d . . . . .
N00M N 0.64485(10) -0.22928(17) 0.34812(7) 0.0321(5) Uani 1 1 d . . . . .
H00M H 0.6695 -0.2902 0.3484 0.039 Uiso 1 1 calc R . . . .
N00N N 1.05229(10) -0.78658(18) 0.35183(7) 0.0325(5) Uani 1 1 d . . . . .
H00N H 1.0276 -0.7258 0.3517 0.039 Uiso 1 1 calc R . . . .
N00O N 0.25407(10) 0.24683(17) 0.05284(7) 0.0320(5) Uani 1 1 d . . . . .
H00O H 0.2300 0.1854 0.0531 0.038 Uiso 1 1 calc R . . . .
N00P N 0.45388(11) 1.32173(19) 0.25146(8) 0.0352(5) Uani 1 1 d . . . . .
N00Q N 0.25859(10) -0.13413(17) 0.04910(7) 0.0323(5) Uani 1 1 d . . . . .
H00Q H 0.2168 -0.1073 0.0500 0.039 Uiso 1 1 calc R . . . .
N00R N -0.15701(10) -0.30847(18) 0.04814(8) 0.0334(5) Uani 1 1 d . . . . .
H00R H -0.1325 -0.2474 0.0485 0.040 Uiso 1 1 calc R . . . .
N00S N 0.60340(10) -0.40054(17) 0.05139(8) 0.0339(5) Uani 1 1 d . . . . .
N00T N 0.04610(10) 0.76265(17) 0.24727(7) 0.0321(5) Uani 1 1 d . . . . .
H00T H 0.0706 0.8236 0.2470 0.039 Uiso 1 1 calc R . . . .
N00U N 0.30420(10) 0.91242(18) 0.25149(8) 0.0333(5) Uani 1 1 d . . . . .
N00V N -0.00530(10) 0.09891(17) 0.04776(8) 0.0325(5) Uani 1 1 d . . . . .
N00W N 0.55925(10) -0.11252(18) 0.34899(7) 0.0328(5) Uani 1 1 d . . . . .
H00W H 0.5175 -0.0859 0.3500 0.039 Uiso 1 1 calc R . . . .
N00X N 0.14290(10) -0.28343(18) 0.34786(8) 0.0341(5) Uani 1 1 d . . . . .
H00X H 0.1677 -0.2226 0.3481 0.041 Uiso 1 1 calc R . . . .
N00Y N 0.34525(10) -0.25038(17) 0.04803(7) 0.0333(5) Uani 1 1 d . . . . .
H00Y H 0.3703 -0.3109 0.0482 0.040 Uiso 1 1 calc R . . . .
N00Z N 0.55429(10) 0.26805(18) 0.35213(8) 0.0344(5) Uani 1 1 d . . . . .
H00Z H 0.5297 0.2071 0.3519 0.041 Uiso 1 1 calc R . . . .
N010 N 0.40758(9) 0.11434(17) 0.34712(7) 0.0301(5) Uani 1 1 d . . . . .
N011 N 0.05701(10) -0.40151(18) 0.34923(8) 0.0340(5) Uani 1 1 d . . . . .
H011 H 0.0155 -0.4287 0.3506 0.041 Uiso 1 1 calc R . . . .
N012 N -0.03913(10) 0.64618(18) 0.24941(8) 0.0349(5) Uani 1 1 d . . . . .
H012 H -0.0807 0.6190 0.2508 0.042 Uiso 1 1 calc R . . . .
N013 N 0.49229(10) -0.65906(18) 0.04775(8) 0.0347(5) Uani 1 1 d . . . . .
N014 N 0.19491(10) 1.17149(18) 0.24803(8) 0.0343(5) Uani 1 1 d . . . . .
N015 N 0.10278(10) -0.16130(18) 0.05210(8) 0.0337(5) Uani 1 1 d . . . . .
N016 N 0.83808(10) -0.92564(18) 0.05123(8) 0.0344(5) Uani 1 1 d . . . . .
H016 H 0.8800 -0.9523 0.0506 0.041 Uiso 1 1 calc R . . . .
N017 N 0.79321(10) -0.63689(18) 0.34841(8) 0.0348(5) Uani 1 1 d . . . . .
N018 N 0.53965(10) 1.43807(18) 0.25115(7) 0.0335(5) Uani 1 1 d . . . . .
H018 H 0.5813 1.4652 0.2502 0.040 Uiso 1 1 calc R . . . .
N019 N 1.13782(10) -0.90267(18) 0.35138(8) 0.0338(5) Uani 1 1 d . . . . .
H019 H 1.1796 -0.9295 0.3508 0.041 Uiso 1 1 calc R . . . .
N01A N 0.29405(10) 0.12199(18) 0.34689(8) 0.0351(5) Uani 1 1 d . . . . .
N01B N 0.40300(10) -0.13817(18) 0.35299(8) 0.0358(5) Uani 1 1 d . . . . .
N01C N 0.63959(10) 0.38562(18) 0.35039(8) 0.0344(5) Uani 1 1 d . . . . .
H01C H 0.6810 0.4131 0.3488 0.041 Uiso 1 1 calc R . . . .
N01D N 0.27896(11) 0.42829(18) 0.05435(8) 0.0379(6) Uani 1 1 d . . . . .
N01E N 0.28894(10) 1.27508(18) 0.24480(8) 0.0345(5) Uani 1 1 d . . . . .
N01F N 0.31924(11) -0.06950(17) 0.04678(8) 0.0369(6) Uani 1 1 d . . . . .
N01G N -0.24190(10) -0.42519(18) 0.04893(8) 0.0357(5) Uani 1 1 d . . . . .
H01G H -0.2835 -0.4524 0.0501 0.043 Uiso 1 1 calc R . . . .
N01H N 0.77817(11) -0.98993(18) 0.05386(8) 0.0396(6) Uani 1 1 d . . . . .
N01I N 0.58688(10) -0.76300(18) 0.04468(8) 0.0373(6) Uani 1 1 d . . . . .
N01J N 0.90347(10) -0.37863(19) 0.35128(8) 0.0357(5) Uani 1 1 d . . . . .
N01K N 0.38968(10) 0.22364(18) 0.34435(8) 0.0379(6) Uani 1 1 d . . . . .
N01L N 0.50849(10) -0.29749(18) 0.05407(8) 0.0367(6) Uani 1 1 d . . . . .
N01M N 0.08929(11) 0.20078(17) 0.04565(8) 0.0370(6) Uani 1 1 d . . . . .
N01N N 0.00848(11) -0.26339(17) 0.05469(8) 0.0371(6) Uani 1 1 d . . . . .
N01O N 1.07854(11) -0.96745(19) 0.35363(8) 0.0393(6) Uani 1 1 d . . . . .
N01P N 0.88653(11) -0.74143(18) 0.34570(8) 0.0381(6) Uani 1 1 d . . . . .
N01Q N 0.20889(11) 0.81096(19) 0.25382(8) 0.0390(6) Uani 1 1 d . . . . .
N01R N 0.27782(11) 0.80876(19) 0.25414(8) 0.0390(6) Uani 1 1 d . . . . .
N01S N 0.51851(11) -0.76353(18) 0.04544(8) 0.0391(6) Uani 1 1 d . . . . .
N01T N 0.22033(10) 1.27619(18) 0.24608(8) 0.0373(6) Uani 1 1 d . . . . .
N01U N -0.18325(11) -0.48867(19) 0.04488(8) 0.0404(6) Uani 1 1 d . . . . .
N01V N 0.37608(11) -0.24307(18) 0.35554(8) 0.0394(6) Uani 1 1 d . . . . .
N01W N 0.47998(11) 1.50272(18) 0.25482(8) 0.0400(6) Uani 1 1 d . . . . .
N01X N 0.57691(10) -0.29567(18) 0.05362(8) 0.0374(6) Uani 1 1 d . . . . .
N01Y N 0.02028(10) 0.20356(18) 0.04555(8) 0.0372(6) Uani 1 1 d . . . . .
N01Z N 0.32144(11) 0.22536(19) 0.34427(8) 0.0395(6) Uani 1 1 d . . . . .
N020 N 0.11698(11) -0.46541(19) 0.34471(8) 0.0394(6) Uani 1 1 d . . . . .
N021 N 0.87851(11) -0.27288(19) 0.35313(8) 0.0393(6) Uani 1 1 d . . . . .
N022 N 0.57991(11) 0.44867(19) 0.35495(8) 0.0391(6) Uani 1 1 d . . . . .
N023 N 0.30720(11) -0.23986(19) 0.35573(8) 0.0401(6) Uani 1 1 d . . . . .
N024 N 0.80949(10) -0.27481(19) 0.35369(8) 0.0366(5) Uani 1 1 d . . . . .
N025 N 0.81854(11) -0.74187(19) 0.34643(9) 0.0409(6) Uani 1 1 d . . . . .
N026 N 0.56716(12) 1.2425(2) 0.24601(9) 0.0430(7) Uani 1 1 d . . . . .
N027 N 0.02023(10) 0.58206(18) 0.24676(8) 0.0375(6) Uani 1 1 d . . . . .
N028 N 1.16513(11) -0.70689(19) 0.34881(9) 0.0433(6) Uani 1 1 d . . . . .
H02G H 1.2096 -0.7180 0.3484 0.052 Uiso 1 1 calc R . . . .
H02H H 1.1487 -0.6391 0.3482 0.052 Uiso 1 1 calc R . . . .
N029 N 0.07701(11) -0.26514(18) 0.05401(9) 0.0412(6) Uani 1 1 d . . . . .
N02A N -0.06747(11) 0.84178(19) 0.25096(9) 0.0460(7) Uani 1 1 d . . . . .
H02O H -0.1119 0.8305 0.2519 0.055 Uiso 1 1 calc R . . . .
H02P H -0.0513 0.9096 0.2509 0.055 Uiso 1 1 calc R . . . .
N02B N -0.26935(11) -0.22995(19) 0.05432(9) 0.0436(6) Uani 1 1 d . . . . .
H02M H -0.3136 -0.2416 0.0556 0.052 Uiso 1 1 calc R . . . .
H02N H -0.2531 -0.1621 0.0553 0.052 Uiso 1 1 calc R . . . .
N02C N 0.61877(11) -0.04742(19) 0.34650(8) 0.0402(6) Uani 1 1 d . . . . .
N02D N 0.86485(11) -0.73052(19) 0.04742(9) 0.0454(7) Uani 1 1 d . . . . .
H02A H 0.9092 -0.7424 0.0468 0.055 Uiso 1 1 calc R . . . .
H02B H 0.8488 -0.6625 0.0466 0.055 Uiso 1 1 calc R . . . .
N02E N 0.23174(11) -0.33000(19) 0.05092(9) 0.0476(7) Uani 1 1 d . . . . .
H02K H 0.1873 -0.3185 0.0515 0.057 Uiso 1 1 calc R . . . .
H02L H 0.2479 -0.3979 0.0512 0.057 Uiso 1 1 calc R . . . .
N02F N 0.53171(11) -0.30904(19) 0.35109(9) 0.0452(7) Uani 1 1 d . . . . .
H02E H 0.4872 -0.2981 0.3517 0.054 Uiso 1 1 calc R . . . .
H02F H 0.5482 -0.3767 0.3514 0.054 Uiso 1 1 calc R . . . .
N02G N 0.36667(11) 0.16907(18) 0.04707(9) 0.0463(7) Uani 1 1 d . . . . .
H02C H 0.4109 0.1808 0.0455 0.056 Uiso 1 1 calc R . . . .
H02D H 0.3506 0.1011 0.0468 0.056 Uiso 1 1 calc R . . . .
N02H N 0.66704(11) 0.19032(19) 0.34504(9) 0.0455(7) Uani 1 1 d . . . . .
H02S H 0.7111 0.2026 0.3432 0.055 Uiso 1 1 calc R . . . .
H02T H 0.6511 0.1222 0.3444 0.055 Uiso 1 1 calc R . . . .
C02I C 1.12224(11) -0.7932(2) 0.35028(8) 0.0285(5) Uani 1 1 d . . . . .
N02J N 0.03040(11) -0.20563(19) 0.35507(9) 0.0465(7) Uani 1 1 d . . . . .
H02Q H -0.0137 -0.2176 0.3568 0.056 Uiso 1 1 calc R . . . .
H02R H 0.0465 -0.1377 0.3560 0.056 Uiso 1 1 calc R . . . .
C02K C 0.34926(11) 0.0524(2) 0.34864(8) 0.0263(5) Uani 1 1 d . . . . .
C02L C 0.82141(12) -0.8165(2) 0.04971(9) 0.0310(6) Uani 1 1 d . . . . .
C02M C -0.22639(11) -0.3162(2) 0.05085(9) 0.0291(6) Uani 1 1 d . . . . .
C02N C 0.54785(11) -0.4693(2) 0.05033(8) 0.0269(5) Uani 1 1 d . . . . .
C02O C 0.84815(11) -0.4471(2) 0.35054(8) 0.0262(5) Uani 1 1 d . . . . .
O02P O 0.40701(17) 0.5252(2) 0.38594(11) 0.0848(9) Uani 1 1 d . . . . .
H02U H 0.4172 0.4977 0.4101 0.127 Uiso 1 1 d G . . . .
H02V H 0.4079 0.5970 0.3873 0.127 Uiso 1 1 d G . . . .
C02Q C 0.04929(10) 0.0293(2) 0.04957(8) 0.0259(5) Uani 1 1 d . . . . .
C02R C 0.24936(11) 0.9817(2) 0.25016(8) 0.0276(5) Uani 1 1 d . . . . .
C02S C 0.84830(11) -0.5678(2) 0.34878(8) 0.0267(5) Uani 1 1 d . . . . .
O02T O 0.30049(16) 0.4661(2) 0.32430(11) 0.0851(9) Uani 1 1 d . . . . .
H02W H 0.3242 0.4954 0.3452 0.128 Uiso 1 1 d G . . . .
H02X H 0.3029 0.3944 0.3261 0.128 Uiso 1 1 d G . . . .
C02U C 0.52415(12) 1.3295(2) 0.24924(9) 0.0310(6) Uani 1 1 d . . . . .
C02V C 0.32352(11) 0.2553(2) 0.04985(9) 0.0291(6) Uani 1 1 d . . . . .
C02W C -0.02410(12) 0.7548(2) 0.24958(9) 0.0313(6) Uani 1 1 d . . . . .
C02X C 0.27502(12) -0.2438(2) 0.04964(9) 0.0309(6) Uani 1 1 d . . . . .
C02Y C 0.25008(11) 1.1027(2) 0.24800(8) 0.0262(5) Uani 1 1 d . . . . .
C02Z C 0.04801(11) -0.09135(19) 0.05188(8) 0.0264(5) Uani 1 1 d . . . . .
C030 C 0.57501(12) -0.2213(2) 0.34964(9) 0.0295(6) Uani 1 1 d . . . . .
C031 C 0.54857(11) -0.5906(2) 0.04816(8) 0.0273(5) Uani 1 1 d . . . . .
C032 C 0.34785(11) -0.0686(2) 0.35175(8) 0.0294(6) Uani 1 1 d . . . . .
C033 C 0.07325(12) -0.2912(2) 0.35113(9) 0.0303(6) Uani 1 1 d . . . . .
C034 C 0.62378(13) 0.2760(2) 0.34886(9) 0.0327(6) Uani 1 1 d . . . . .
C035 C 0.36830(12) -0.1438(2) 0.04605(9) 0.0360(6) Uani 1 1 d . . . . .
H035 H 0.4153 -0.1253 0.0443 0.043 Uiso 1 1 calc R . . . .
C036 C 0.53073(13) 0.3748(2) 0.35576(10) 0.0378(7) Uani 1 1 d . . . . .
C037 C 0.22906(12) 0.3541(2) 0.05545(10) 0.0360(6) Uani 1 1 d . . . . .
H037 H 0.1821 0.3720 0.0577 0.043 Uiso 1 1 calc R . . . .
C038 C 0.66885(13) -0.1211(2) 0.34609(9) 0.0360(6) Uani 1 1 d . . . . .
H038 H 0.7159 -0.1024 0.3446 0.043 Uiso 1 1 calc R . . . .
C039 C 0.43024(13) 1.4290(2) 0.25477(10) 0.0394(7) Uani 1 1 d . . . . .
C03A C 0.06998(13) 0.6553(2) 0.24547(10) 0.0390(7) Uani 1 1 d . . . . .
H03A H 0.1169 0.6366 0.2435 0.047 Uiso 1 1 calc R . . . .
O03B O 0.1169(2) 0.5161(3) 0.09965(12) 0.1067(12) Uani 1 1 d . . . . .
H03B H 0.1198 0.5864 0.1049 0.160 Uiso 1 1 d G . . . .
H03E H 0.1127 0.4799 0.1221 0.160 Uiso 1 1 d G . . . .
C03C C 1.02792(13) -0.8944(2) 0.35370(10) 0.0400(7) Uani 1 1 d . . . . .
H03C H 0.9808 -0.9134 0.3549 0.048 Uiso 1 1 calc R . . . .
C03D C 0.16611(12) -0.3909(2) 0.34417(10) 0.0381(7) Uani 1 1 d . . . . .
H03D H 0.2129 -0.4091 0.3415 0.046 Uiso 1 1 calc R . . . .
O03E O 0.01272(18) 0.4503(2) 0.03758(15) 0.1082(13) Uani 1 1 d . . . . .
H03H H 0.0077 0.3803 0.0321 0.162 Uiso 1 1 d G . . . .
H03I H 0.0496 0.4602 0.0541 0.162 Uiso 1 1 d G . . . .
C03F C 0.72854(13) -0.9167(2) 0.05402(10) 0.0392(7) Uani 1 1 d . . . . .
H03F H 0.6816 -0.9357 0.0558 0.047 Uiso 1 1 calc R . . . .
C03G C -0.13287(13) -0.4156(2) 0.04482(10) 0.0381(7) Uani 1 1 d . . . . .
H03G H -0.0859 -0.4341 0.0428 0.046 Uiso 1 1 calc R . . . .
O03H O 0.1687(2) 0.4784(3) 0.18282(14) 0.1193(14) Uani 1 1 d . . . . .
H03J H 0.1928 0.5210 0.2000 0.179 Uiso 1 1 d G . . . .
H03K H 0.1692 0.4112 0.1923 0.179 Uiso 1 1 d G . . . .
O03I O 0.2680(3) 0.5569(2) 0.24582(14) 0.1257(15) Uani 1 1 d . . . . .
H03L H 0.2782 0.5435 0.2716 0.189 Uiso 1 1 d G . . . .
H03M H 0.2647 0.6277 0.2419 0.189 Uiso 1 1 d G . . . .
O03J O 0.4536(3) 0.4578(3) 0.46822(13) 0.1213(14) Uani 1 1 d . . . . .
H03N H 0.4465 0.4815 0.4924 0.182 Uiso 1 1 d G . . . .
H03O H 0.4444 0.3876 0.4665 0.182 Uiso 1 1 d G . . . .
H036 H 0.4813(17) 0.387(3) 0.3592(11) 0.067(11) Uiso 1 1 d . . . . .
H00P H 0.4265(17) 1.259(3) 0.2495(11) 0.064(11) Uiso 1 1 d . . . . .
H039 H 0.3834(17) 1.448(3) 0.2592(10) 0.062(10) Uiso 1 1 d . . . . .
H02I H 0.5504(14) 1.180(2) 0.2459(8) 0.026(7) Uiso 1 1 d . . . . .
H02J H 0.6126(16) 1.258(3) 0.2425(10) 0.050(9) Uiso 1 1 d . . . . .
H00J H 0.7228(15) -0.745(3) 0.0516(9) 0.044(8) 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
O001 N00C 1.318(2) . ?
O002 N00D 1.315(2) . ?
O003 N00I 1.310(2) . ?
O004 N00B 1.304(2) . ?
O005 N00F 1.308(2) . ?
O006 N00G 1.326(2) . ?
O007 N00L 1.304(2) . ?
O008 N00H 1.322(2) . ?
O009 N00E 1.317(2) . ?
O00A N010 1.316(2) . ?
N00B N01M 1.338(3) . ?
N00B C02Q 1.350(3) . ?
N00C N01Q 1.325(3) . ?
N00C C02R 1.342(3) . ?
N00D N01E 1.329(3) . ?
N00D C02Y 1.344(3) . ?
N00E N023 1.333(3) . ?
N00E C032 1.336(3) . ?
N00F N01N 1.341(3) . ?
N00F C02Z 1.347(3) . ?
N00G N01I 1.334(3) . ?
N00G C031 1.329(3) . ?
N00H N01L 1.328(3) . ?
N00H C02N 1.335(3) . ?
N00I N01P 1.355(3) . ?
N00I C02S 1.349(3) . ?
N00J C02L 1.343(3) . ?
N00J C03F 1.346(3) . ?
N00J H00J 0.94(3) . ?
N00K H00K 0.8600 . ?
N00K N01D 1.382(3) . ?
N00K C02V 1.317(3) . ?
N00L N024 1.345(3) . ?
N00L C02O 1.343(3) . ?
N00M H00M 0.8600 . ?
N00M C030 1.340(3) . ?
N00M C038 1.363(3) . ?
N00N H00N 0.8600 . ?
N00N C02I 1.341(3) . ?
N00N C03C 1.361(3) . ?
N00O H00O 0.8600 . ?
N00O C02V 1.340(3) . ?
N00O C037 1.362(3) . ?
N00P C02U 1.351(3) . ?
N00P C039 1.354(3) . ?
N00P H00P 0.91(4) . ?
N00Q H00Q 0.8600 . ?
N00Q N01F 1.394(3) . ?
N00Q C02X 1.335(3) . ?
N00R H00R 0.8600 . ?
N00R C02M 1.337(3) . ?
N00R C03G 1.355(3) . ?
N00S N01X 1.344(3) . ?
N00S C02N 1.333(3) . ?
N00T H00T 0.8600 . ?
N00T C02W 1.350(3) . ?
N00T C03A 1.352(3) . ?
N00U N01R 1.331(3) . ?
N00U C02R 1.326(3) . ?
N00V N01Y 1.335(3) . ?
N00V C02Q 1.324(3) . ?
N00W H00W 0.8600 . ?
N00W N02C 1.380(3) . ?
N00W C030 1.322(3) . ?
N00X H00X 0.8600 . ?
N00X C033 1.345(3) . ?
N00X C03D 1.355(3) . ?
N00Y H00Y 0.8600 . ?
N00Y C02X 1.347(3) . ?
N00Y C035 1.339(3) . ?
N00Z H00Z 0.8600 . ?
N00Z C034 1.342(3) . ?
N00Z C036 1.349(3) . ?
N010 N01K 1.338(3) . ?
N010 C02K 1.336(3) . ?
N011 H011 0.8600 . ?
N011 N020 1.389(3) . ?
N011 C033 1.341(3) . ?
N012 H012 0.8600 . ?
N012 N027 1.372(3) . ?
N012 C02W 1.317(3) . ?
N013 N01S 1.338(3) . ?
N013 C031 1.343(3) . ?
N014 N01T 1.334(3) . ?
N014 C02Y 1.330(3) . ?
N015 N029 1.327(3) . ?
N015 C02Z 1.332(3) . ?
N016 H016 0.8600 . ?
N016 N01H 1.381(3) . ?
N016 C02L 1.329(3) . ?
N017 N025 1.336(3) . ?
N017 C02S 1.330(3) . ?
N018 H018 0.8600 . ?
N018 N01W 1.385(3) . ?
N018 C02U 1.318(3) . ?
N019 H019 0.8600 . ?
N019 N01O 1.373(3) . ?
N019 C02I 1.328(3) . ?
N01A N01Z 1.336(3) . ?
N01A C02K 1.333(3) . ?
N01B N01V 1.348(3) . ?
N01B C032 1.333(3) . ?
N01C H01C 0.8600 . ?
N01C N022 1.380(3) . ?
N01C C034 1.331(3) . ?
N01D C037 1.297(3) . ?
N01E N01T 1.313(3) . ?
N01F C035 1.285(3) . ?
N01G H01G 0.8600 . ?
N01G N01U 1.363(3) . ?
N01G C02M 1.323(3) . ?
N01H C03F 1.283(3) . ?
N01I N01S 1.306(3) . ?
N01J N021 1.342(3) . ?
N01J C02O 1.328(3) . ?
N01K N01Z 1.301(3) . ?
N01L N01X 1.306(3) . ?
N01M N01Y 1.316(3) . ?
N01N N029 1.309(3) . ?
N01O C03C 1.295(3) . ?
N01P N025 1.298(3) . ?
N01Q N01R 1.313(3) . ?
N01U C03G 1.293(3) . ?
N01V N023 1.314(3) . ?
N01W C039 1.288(3) . ?
N020 C03D 1.287(3) . ?
N021 N024 1.318(3) . ?
N022 C036 1.284(3) . ?
N026 C02U 1.326(3) . ?
N026 H02I 0.80(3) . ?
N026 H02J 0.90(3) . ?
N027 C03A 1.289(3) . ?
N028 H02G 0.8600 . ?
N028 H02H 0.8600 . ?
N028 C02I 1.312(3) . ?
N02A H02O 0.8600 . ?
N02A H02P 0.8600 . ?
N02A C02W 1.323(3) . ?
N02B H02M 0.8600 . ?
N02B H02N 0.8600 . ?
N02B C02M 1.320(3) . ?
N02C C038 1.294(3) . ?
N02D H02A 0.8600 . ?
N02D H02B 0.8600 . ?
N02D C02L 1.318(3) . ?
N02E H02K 0.8600 . ?
N02E H02L 0.8600 . ?
N02E C02X 1.314(3) . ?
N02F H02E 0.8600 . ?
N02F H02F 0.8600 . ?
N02F C030 1.329(3) . ?
N02G H02C 0.8600 . ?
N02G H02D 0.8600 . ?
N02G C02V 1.319(3) . ?
N02H H02S 0.8600 . ?
N02H H02T 0.8600 . ?
N02H C034 1.320(3) . ?
N02J H02Q 0.8600 . ?
N02J H02R 0.8600 . ?
N02J C033 1.314(3) . ?
C02K C032 1.435(3) . ?
C02N C031 1.437(3) . ?
C02O C02S 1.430(3) . ?
O02P H02U 0.8495 . ?
O02P H02V 0.8499 . ?
C02Q C02Z 1.430(3) . ?
C02R C02Y 1.433(3) . ?
O02T H02W 0.8499 . ?
O02T H02X 0.8508 . ?
C035 H035 0.9300 . ?
C036 H036 0.97(3) . ?
C037 H037 0.9300 . ?
C038 H038 0.9300 . ?
C039 H039 0.95(3) . ?
C03A H03A 0.9300 . ?
O03B H03B 0.8502 . ?
O03B H03E 0.8501 . ?
C03C H03C 0.9300 . ?
C03D H03D 0.9300 . ?
O03E H03H 0.8502 . ?
O03E H03I 0.8494 . ?
C03F H03F 0.9300 . ?
C03G H03G 0.9300 . ?
O03H H03J 0.8513 . ?
O03H H03K 0.8510 . ?
O03I H03L 0.8507 . ?
O03I H03M 0.8491 . ?
O03J H03N 0.8507 . ?
O03J H03O 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
O004 N00B N01M 122.58(19) . . ?
O004 N00B C02Q 129.44(19) . . ?
N01M N00B C02Q 107.97(18) . . ?
O001 N00C N01Q 121.70(19) . . ?
O001 N00C C02R 129.4(2) . . ?
N01Q N00C C02R 108.91(19) . . ?
O002 N00D N01E 122.20(19) . . ?
O002 N00D C02Y 128.8(2) . . ?
N01E N00D C02Y 108.95(19) . . ?
O009 N00E N023 121.32(19) . . ?
O009 N00E C032 129.3(2) . . ?
N023 N00E C032 109.33(19) . . ?
O005 N00F N01N 122.52(19) . . ?
O005 N00F C02Z 129.4(2) . . ?
N01N N00F C02Z 108.04(18) . . ?
O006 N00G N01I 121.77(18) . . ?
O006 N00G C031 128.8(2) . . ?
C031 N00G N01I 109.38(18) . . ?
O008 N00H N01L 121.48(18) . . ?
O008 N00H C02N 129.1(2) . . ?
N01L N00H C02N 109.42(19) . . ?
O003 N00I N01P 122.34(19) . . ?
O003 N00I C02S 129.9(2) . . ?
C02S N00I N01P 107.76(18) . . ?
C02L N00J C03F 105.8(2) . . ?
C02L N00J H00J 129.1(18) . . ?
C03F N00J H00J 125.1(18) . . ?
N01D N00K H00K 124.5 . . ?
C02V N00K H00K 124.5 . . ?
C02V N00K N01D 111.09(19) . . ?
O007 N00L N024 122.38(19) . . ?
O007 N00L C02O 129.7(2) . . ?
C02O N00L N024 107.87(19) . . ?
C030 N00M H00M 127.0 . . ?
C030 N00M C038 106.0(2) . . ?
C038 N00M H00M 127.0 . . ?
C02I N00N H00N 126.5 . . ?
C02I N00N C03C 106.9(2) . . ?
C03C N00N H00N 126.5 . . ?
C02V N00O H00O 126.6 . . ?
C02V N00O C037 106.8(2) . . ?
C037 N00O H00O 126.6 . . ?
C02U N00P C039 106.2(2) . . ?
C02U N00P H00P 128(2) . . ?
C039 N00P H00P 125(2) . . ?
N01F N00Q H00Q 125.1 . . ?
C02X N00Q H00Q 125.1 . . ?
C02X N00Q N01F 109.84(19) . . ?
C02M N00R H00R 126.7 . . ?
C02M N00R C03G 106.6(2) . . ?
C03G N00R H00R 126.7 . . ?
C02N N00S N01X 105.24(19) . . ?
C02W N00T H00T 127.0 . . ?
C02W N00T C03A 106.1(2) . . ?
C03A N00T H00T 127.0 . . ?
C02R N00U N01R 105.70(19) . . ?
C02Q N00V N01Y 106.84(19) . . ?
N02C N00W H00W 124.5 . . ?
C030 N00W H00W 124.5 . . ?
C030 N00W N02C 110.96(19) . . ?
C033 N00X H00X 127.0 . . ?
C033 N00X C03D 106.0(2) . . ?
C03D N00X H00X 127.0 . . ?
C02X N00Y H00Y 126.9 . . ?
C035 N00Y H00Y 126.9 . . ?
C035 N00Y C02X 106.23(19) . . ?
C034 N00Z H00Z 126.9 . . ?
C034 N00Z C036 106.3(2) . . ?
C036 N00Z H00Z 126.9 . . ?
O00A N010 N01K 121.77(19) . . ?
O00A N010 C02K 129.3(2) . . ?
C02K N010 N01K 108.93(19) . . ?
N020 N011 H011 124.9 . . ?
C033 N011 H011 124.9 . . ?
C033 N011 N020 110.21(19) . . ?
N027 N012 H012 124.5 . . ?
C02W N012 H012 124.5 . . ?
C02W N012 N027 111.1(2) . . ?
N01S N013 C031 104.80(18) . . ?
C02Y N014 N01T 106.12(19) . . ?
N029 N015 C02Z 106.39(19) . . ?
N01H N016 H016 125.0 . . ?
C02L N016 H016 125.0 . . ?
C02L N016 N01H 109.93(19) . . ?
C02S N017 N025 106.43(19) . . ?
N01W N018 H018 124.5 . . ?
C02U N018 H018 124.5 . . ?
C02U N018 N01W 111.09(19) . . ?
N01O N019 H019 124.4 . . ?
C02I N019 H019 124.4 . . ?
C02I N019 N01O 111.26(19) . . ?
C02K N01A N01Z 104.85(19) . . ?
C032 N01B N01V 105.47(19) . . ?
N022 N01C H01C 124.9 . . ?
C034 N01C H01C 124.9 . . ?
C034 N01C N022 110.2(2) . . ?
C037 N01D N00K 103.9(2) . . ?
N01T N01E N00D 106.07(19) . . ?
C035 N01F N00Q 103.5(2) . . ?
N01U N01G H01G 124.5 . . ?
C02M N01G H01G 124.5 . . ?
C02M N01G N01U 111.1(2) . . ?
C03F N01H N016 104.0(2) . . ?
N01S N01I N00G 105.53(18) . . ?
C02O N01J N021 106.58(19) . . ?
N01Z N01K N010 105.31(19) . . ?
N01X N01L N00H 105.78(19) . . ?
N01Y N01M N00B 106.8(2) . . ?
N029 N01N N00F 106.44(19) . . ?
C03C N01O N019 104.2(2) . . ?
N025 N01P N00I 106.5(2) . . ?
N01R N01Q N00C 105.83(19) . . ?
N01Q N01R N00U 111.4(2) . . ?
N01I N01S N013 112.0(2) . . ?
N01E N01T N014 111.08(19) . . ?
C03G N01U N01G 104.3(2) . . ?
N023 N01V N01B 111.1(2) . . ?
C039 N01W N018 103.7(2) . . ?
N01L N01X N00S 111.5(2) . . ?
N01M N01Y N00V 110.29(19) . . ?
N01K N01Z N01A 112.5(2) . . ?
C03D N020 N011 103.6(2) . . ?
N024 N021 N01J 110.1(2) . . ?
C036 N022 N01C 104.2(2) . . ?
N01V N023 N00E 105.8(2) . . ?
N021 N024 N00L 106.9(2) . . ?
N01P N025 N017 111.3(2) . . ?
C02U N026 H02I 117.6(19) . . ?
C02U N026 H02J 117(2) . . ?
H02I N026 H02J 125(3) . . ?
C03A N027 N012 104.1(2) . . ?
H02G N028 H02H 120.0 . . ?
C02I N028 H02G 120.0 . . ?
C02I N028 H02H 120.0 . . ?
N01N N029 N015 111.13(19) . . ?
H02O N02A H02P 120.0 . . ?
C02W N02A H02O 120.0 . . ?
C02W N02A H02P 120.0 . . ?
H02M N02B H02N 120.0 . . ?
C02M N02B H02M 120.0 . . ?
C02M N02B H02N 120.0 . . ?
C038 N02C N00W 103.6(2) . . ?
H02A N02D H02B 120.0 . . ?
C02L N02D H02A 120.0 . . ?
C02L N02D H02B 120.0 . . ?
H02K N02E H02L 120.0 . . ?
C02X N02E H02K 120.0 . . ?
C02X N02E H02L 120.0 . . ?
H02E N02F H02F 120.0 . . ?
C030 N02F H02E 120.0 . . ?
C030 N02F H02F 120.0 . . ?
H02C N02G H02D 120.0 . . ?
C02V N02G H02C 120.0 . . ?
C02V N02G H02D 120.0 . . ?
H02S N02H H02T 120.0 . . ?
C034 N02H H02S 120.0 . . ?
C034 N02H H02T 120.0 . . ?
N019 C02I N00N 106.1(2) . . ?
N028 C02I N00N 125.5(2) . . ?
N028 C02I N019 128.4(2) . . ?
H02Q N02J H02R 120.0 . . ?
C033 N02J H02Q 120.0 . . ?
C033 N02J H02R 120.0 . . ?
N010 C02K C032 124.8(2) . . ?
N01A C02K N010 108.4(2) . . ?
N01A C02K C032 126.8(2) . . ?
N016 C02L N00J 107.1(2) . . ?
N02D C02L N00J 125.9(2) . . ?
N02D C02L N016 127.0(2) . . ?
N01G C02M N00R 106.4(2) . . ?
N02B C02M N00R 125.3(2) . . ?
N02B C02M N01G 128.3(2) . . ?
N00H C02N C031 125.1(2) . . ?
N00S C02N N00H 108.1(2) . . ?
N00S C02N C031 126.8(2) . . ?
N00L C02O C02S 124.1(2) . . ?
N01J C02O N00L 108.6(2) . . ?
N01J C02O C02S 127.3(2) . . ?
H02U O02P H02V 109.5 . . ?
N00B C02Q C02Z 124.58(19) . . ?
N00V C02Q N00B 108.1(2) . . ?
N00V C02Q C02Z 127.3(2) . . ?
N00C C02R C02Y 124.4(2) . . ?
N00U C02R N00C 108.2(2) . . ?
N00U C02R C02Y 127.5(2) . . ?
N00I C02S C02O 124.4(2) . . ?
N017 C02S N00I 108.1(2) . . ?
N017 C02S C02O 127.6(2) . . ?
H02W O02T H02X 109.4 . . ?
N018 C02U N00P 106.4(2) . . ?
N018 C02U N026 128.5(2) . . ?
N026 C02U N00P 125.1(2) . . ?
N00K C02V N00O 106.7(2) . . ?
N00K C02V N02G 128.3(2) . . ?
N02G C02V N00O 125.0(2) . . ?
N012 C02W N00T 106.5(2) . . ?
N012 C02W N02A 128.5(2) . . ?
N02A C02W N00T 125.0(2) . . ?
N00Q C02X N00Y 106.7(2) . . ?
N02E C02X N00Q 127.4(2) . . ?
N02E C02X N00Y 125.9(2) . . ?
N00D C02Y C02R 125.3(2) . . ?
N014 C02Y N00D 107.8(2) . . ?
N014 C02Y C02R 126.9(2) . . ?
N00F C02Z C02Q 124.9(2) . . ?
N015 C02Z N00F 108.0(2) . . ?
N015 C02Z C02Q 127.1(2) . . ?
N00W C030 N00M 107.0(2) . . ?
N00W C030 N02F 128.3(2) . . ?
N02F C030 N00M 124.7(2) . . ?
N00G C031 N013 108.2(2) . . ?
N00G C031 C02N 125.5(2) . . ?
N013 C031 C02N 126.3(2) . . ?
N00E C032 C02K 125.0(2) . . ?
N01B C032 N00E 108.3(2) . . ?
N01B C032 C02K 126.7(2) . . ?
N011 C033 N00X 106.8(2) . . ?
N02J C033 N00X 125.6(2) . . ?
N02J C033 N011 127.7(2) . . ?
N01C C034 N00Z 106.7(2) . . ?
N02H C034 N00Z 125.7(2) . . ?
N02H C034 N01C 127.6(2) . . ?
N00Y C035 H035 123.2 . . ?
N01F C035 N00Y 113.6(2) . . ?
N01F C035 H035 123.2 . . ?
N00Z C036 H036 119(2) . . ?
N022 C036 N00Z 112.7(2) . . ?
N022 C036 H036 128(2) . . ?
N00O C037 H037 124.2 . . ?
N01D C037 N00O 111.5(2) . . ?
N01D C037 H037 124.2 . . ?
N00M C038 H038 123.8 . . ?
N02C C038 N00M 112.4(2) . . ?
N02C C038 H038 123.8 . . ?
N00P C039 H039 124(2) . . ?
N01W C039 N00P 112.6(2) . . ?
N01W C039 H039 123(2) . . ?
N00T C03A H03A 123.9 . . ?
N027 C03A N00T 112.3(2) . . ?
N027 C03A H03A 123.9 . . ?
H03B O03B H03E 109.5 . . ?
N00N C03C H03C 124.2 . . ?
N01O C03C N00N 111.6(2) . . ?
N01O C03C H03C 124.2 . . ?
N00X C03D H03D 123.3 . . ?
N020 C03D N00X 113.4(2) . . ?
N020 C03D H03D 123.3 . . ?
H03H O03E H03I 109.5 . . ?
N00J C03F H03F 123.4 . . ?
N01H C03F N00J 113.1(2) . . ?
N01H C03F H03F 123.4 . . ?
N00R C03G H03G 124.2 . . ?
N01U C03G N00R 111.6(2) . . ?
N01U C03G H03G 124.2 . . ?
H03J O03H H03K 109.4 . . ?
H03L O03I H03M 109.6 . . ?
H03N O03J H03O 109.4 . . ?

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
O001 N00C N01Q N01R 179.3(2) . . . . ?
O001 N00C C02R N00U -178.6(3) . . . . ?
O001 N00C C02R C02Y 1.8(4) . . . . ?
O002 N00D N01E N01T -179.1(2) . . . . ?
O002 N00D C02Y N014 179.1(3) . . . . ?
O002 N00D C02Y C02R -0.3(4) . . . . ?
O003 N00I N01P N025 179.0(2) . . . . ?
O003 N00I C02S N017 -178.7(3) . . . . ?
O003 N00I C02S C02O 1.0(4) . . . . ?
O004 N00B N01M N01Y -178.8(2) . . . . ?
O004 N00B C02Q N00V 179.0(3) . . . . ?
O004 N00B C02Q C02Z -1.8(4) . . . . ?
O005 N00F N01N N029 179.6(2) . . . . ?
O005 N00F C02Z N015 -179.3(3) . . . . ?
O005 N00F C02Z C02Q -0.3(5) . . . . ?
O006 N00G N01I N01S 179.2(2) . . . . ?
O006 N00G C031 N013 -178.9(2) . . . . ?
O006 N00G C031 C02N 0.8(5) . . . . ?
O007 N00L N024 N021 -179.5(2) . . . . ?
O007 N00L C02O N01J 179.6(3) . . . . ?
O007 N00L C02O C02S -0.9(4) . . . . ?
O008 N00H N01L N01X -179.2(2) . . . . ?
O008 N00H C02N N00S 179.3(3) . . . . ?
O008 N00H C02N C031 -1.2(5) . . . . ?
O009 N00E N023 N01V 179.7(2) . . . . ?
O009 N00E C032 N01B -179.6(3) . . . . ?
O009 N00E C032 C02K -0.6(5) . . . . ?
O00A N010 N01K N01Z -179.0(2) . . . . ?
O00A N010 C02K N01A 178.9(3) . . . . ?
O00A N010 C02K C032 -1.0(4) . . . . ?
N00B N01M N01Y N00V -0.5(3) . . . . ?
N00B C02Q C02Z N00F 179.3(3) . . . . ?
N00B C02Q C02Z N015 -1.9(5) . . . . ?
N00C N01Q N01R N00U -0.8(3) . . . . ?
N00C C02R C02Y N00D -178.7(2) . . . . ?
N00C C02R C02Y N014 1.9(5) . . . . ?
N00D N01E N01T N014 0.0(3) . . . . ?
N00F N01N N029 N015 -0.5(3) . . . . ?
N00G N01I N01S N013 -0.2(3) . . . . ?
N00H N01L N01X N00S -0.2(3) . . . . ?
N00H C02N C031 N00G 179.8(3) . . . . ?
N00H C02N C031 N013 -0.5(5) . . . . ?
N00I N01P N025 N017 0.2(3) . . . . ?
N00K N01D C037 N00O 0.3(3) . . . . ?
N00L C02O C02S N00I -179.8(3) . . . . ?
N00L C02O C02S N017 -0.1(4) . . . . ?
N00Q N01F C035 N00Y -0.5(3) . . . . ?
N00S C02N C031 N00G -0.8(5) . . . . ?
N00S C02N C031 N013 178.9(3) . . . . ?
N00U C02R C02Y N00D 1.7(5) . . . . ?
N00U C02R C02Y N014 -177.7(3) . . . . ?
N00V C02Q C02Z N00F -1.6(5) . . . . ?
N00V C02Q C02Z N015 177.2(3) . . . . ?
N00W N02C C038 N00M 0.1(3) . . . . ?
N010 N01K N01Z N01A 0.0(3) . . . . ?
N010 C02K C032 N00E -179.8(3) . . . . ?
N010 C02K C032 N01B -1.0(4) . . . . ?
N011 N020 C03D N00X -0.2(3) . . . . ?
N012 N027 C03A N00T 0.2(3) . . . . ?
N016 N01H C03F N00J 0.5(4) . . . . ?
N018 N01W C039 N00P 0.2(4) . . . . ?
N019 N01O C03C N00N -0.3(3) . . . . ?
N01A C02K C032 N00E 0.3(4) . . . . ?
N01A C02K C032 N01B 179.1(3) . . . . ?
N01B N01V N023 N00E 0.1(3) . . . . ?
N01C N022 C036 N00Z 0.1(3) . . . . ?
N01D N00K C02V N00O 0.2(3) . . . . ?
N01D N00K C02V N02G -179.2(3) . . . . ?
N01E N00D C02Y N014 0.1(3) . . . . ?
N01E N00D C02Y C02R -179.3(2) . . . . ?
N01F N00Q C02X N00Y 0.5(3) . . . . ?
N01F N00Q C02X N02E -178.7(3) . . . . ?
N01G N01U C03G N00R -0.7(3) . . . . ?
N01H N016 C02L N00J 0.0(3) . . . . ?
N01H N016 C02L N02D 179.4(3) . . . . ?
N01I N00G C031 N013 0.2(3) . . . . ?
N01I N00G C031 C02N 180.0(3) . . . . ?
N01J N021 N024 N00L -0.2(3) . . . . ?
N01J C02O C02S N00I -0.3(4) . . . . ?
N01J C02O C02S N017 179.3(3) . . . . ?
N01K N010 C02K N01A 0.0(3) . . . . ?
N01K N010 C02K C032 -179.9(2) . . . . ?
N01L N00H C02N N00S 0.0(3) . . . . ?
N01L N00H C02N C031 179.5(3) . . . . ?
N01M N00B C02Q N00V -0.2(3) . . . . ?
N01M N00B C02Q C02Z 179.1(2) . . . . ?
N01N N00F C02Z N015 -0.1(3) . . . . ?
N01N N00F C02Z C02Q 178.9(3) . . . . ?
N01O N019 C02I N00N 0.0(3) . . . . ?
N01O N019 C02I N028 178.8(3) . . . . ?
N01P N00I C02S N017 0.6(3) . . . . ?
N01P N00I C02S C02O -179.6(2) . . . . ?
N01Q N00C C02R N00U 0.4(3) . . . . ?
N01Q N00C C02R C02Y -179.3(3) . . . . ?
N01R N00U C02R N00C -0.9(3) . . . . ?
N01R N00U C02R C02Y 178.8(3) . . . . ?
N01S N013 C031 N00G -0.3(3) . . . . ?
N01S N013 C031 C02N 179.9(3) . . . . ?
N01T N014 C02Y N00D -0.1(3) . . . . ?
N01T N014 C02Y C02R 179.3(3) . . . . ?
N01U N01G C02M N00R -0.2(3) . . . . ?
N01U N01G C02M N02B 179.2(3) . . . . ?
N01V N01B C032 N00E -0.5(3) . . . . ?
N01V N01B C032 C02K -179.4(3) . . . . ?
N01W N018 C02U N00P 0.2(3) . . . . ?
N01W N018 C02U N026 -179.4(3) . . . . ?
N01X N00S C02N N00H -0.1(3) . . . . ?
N01X N00S C02N C031 -179.6(3) . . . . ?
N01Y N00V C02Q N00B -0.2(3) . . . . ?
N01Y N00V C02Q C02Z -179.4(3) . . . . ?
N01Z N01A C02K N010 0.1(3) . . . . ?
N01Z N01A C02K C032 179.9(3) . . . . ?
N020 N011 C033 N00X 0.0(3) . . . . ?
N020 N011 C033 N02J 179.5(3) . . . . ?
N021 N01J C02O N00L -0.2(3) . . . . ?
N021 N01J C02O C02S -179.7(3) . . . . ?
N022 N01C C034 N00Z 0.4(3) . . . . ?
N022 N01C C034 N02H -179.4(3) . . . . ?
N023 N00E C032 N01B 0.6(3) . . . . ?
N023 N00E C032 C02K 179.6(2) . . . . ?
N024 N00L C02O N01J 0.1(3) . . . . ?
N024 N00L C02O C02S 179.6(2) . . . . ?
N025 N017 C02S N00I -0.5(3) . . . . ?
N025 N017 C02S C02O 179.8(3) . . . . ?
N027 N012 C02W N00T -0.4(3) . . . . ?
N027 N012 C02W N02A 178.5(3) . . . . ?
N029 N015 C02Z N00F -0.2(3) . . . . ?
N029 N015 C02Z C02Q -179.2(3) . . . . ?
N02C N00W C030 N00M 0.8(3) . . . . ?
N02C N00W C030 N02F -178.6(3) . . . . ?
C02I N00N C03C N01O 0.3(4) . . . . ?
C02I N019 N01O C03C 0.2(3) . . . . ?
C02K N010 N01K N01Z 0.0(3) . . . . ?
C02K N01A N01Z N01K -0.1(3) . . . . ?
C02L N00J C03F N01H -0.6(4) . . . . ?
C02L N016 N01H C03F -0.3(3) . . . . ?
C02M N00R C03G N01U 0.7(4) . . . . ?
C02M N01G N01U C03G 0.5(3) . . . . ?
C02N N00H N01L N01X 0.1(3) . . . . ?
C02N N00S N01X N01L 0.2(3) . . . . ?
C02O N00L N024 N021 0.0(3) . . . . ?
C02O N01J N021 N024 0.2(3) . . . . ?
C02Q N00B N01M N01Y 0.4(3) . . . . ?
C02Q N00V N01Y N01M 0.4(3) . . . . ?
C02R N00C N01Q N01R 0.2(3) . . . . ?
C02R N00U N01R N01Q 1.0(3) . . . . ?
C02S N00I N01P N025 -0.5(3) . . . . ?
C02S N017 N025 N01P 0.2(3) . . . . ?
C02U N00P C039 N01W -0.1(4) . . . . ?
C02U N018 N01W C039 -0.3(3) . . . . ?
C02V N00K N01D C037 -0.3(3) . . . . ?
C02V N00O C037 N01D -0.1(3) . . . . ?
C02W N00T C03A N027 -0.4(4) . . . . ?
C02W N012 N027 C03A 0.1(3) . . . . ?
C02X N00Q N01F C035 0.0(3) . . . . ?
C02X N00Y C035 N01F 0.8(4) . . . . ?
C02Y N00D N01E N01T -0.1(3) . . . . ?
C02Y N014 N01T N01E 0.1(3) . . . . ?
C02Z N00F N01N N029 0.4(3) . . . . ?
C02Z N015 N029 N01N 0.5(3) . . . . ?
C030 N00M C038 N02C 0.4(3) . . . . ?
C030 N00W N02C C038 -0.5(3) . . . . ?
C031 N00G N01I N01S 0.0(3) . . . . ?
C031 N013 N01S N01I 0.4(3) . . . . ?
C032 N00E N023 N01V -0.4(3) . . . . ?
C032 N01B N01V N023 0.2(3) . . . . ?
C033 N00X C03D N020 0.2(4) . . . . ?
C033 N011 N020 C03D 0.1(3) . . . . ?
C034 N00Z C036 N022 0.1(4) . . . . ?
C034 N01C N022 C036 -0.3(3) . . . . ?
C035 N00Y C02X N00Q -0.8(3) . . . . ?
C035 N00Y C02X N02E 178.4(3) . . . . ?
C036 N00Z C034 N01C -0.3(3) . . . . ?
C036 N00Z C034 N02H 179.5(3) . . . . ?
C037 N00O C02V N00K -0.1(3) . . . . ?
C037 N00O C02V N02G 179.4(3) . . . . ?
C038 N00M C030 N00W -0.7(3) . . . . ?
C038 N00M C030 N02F 178.8(3) . . . . ?
C039 N00P C02U N018 -0.1(3) . . . . ?
C039 N00P C02U N026 179.5(3) . . . . ?
C03A N00T C02W N012 0.5(3) . . . . ?
C03A N00T C02W N02A -178.5(3) . . . . ?
C03C N00N C02I N019 -0.2(3) . . . . ?
C03C N00N C02I N028 -179.0(3) . . . . ?
C03D N00X C033 N011 -0.1(3) . . . . ?
C03D N00X C033 N02J -179.7(3) . . . . ?
C03F N00J C02L N016 0.3(3) . . . . ?
C03F N00J C02L N02D -179.1(3) . . . . ?
C03G N00R C02M N01G -0.3(3) . . . . ?
C03G N00R C02M N02B -179.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
