# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_exp_258
_database_code_depnum_ccdc_archive 'CCDC 1472958'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_exp_258             
;
PROBLEM: D-H Without Acceptor       N6     --  H6B    ...     Please Check
RESPONSE: The hydrogen atom is probably donated to a water molecule.
;
# Added during the CSD deposition process: Tuesday 12 July 2016 08:42 AM
# end Validation Reply Form

_audit_creation_date             2016-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        'Triple 3c'
_chemical_formula_moiety         'C14 H15 N5 O3, H2 O'
_chemical_formula_sum            'C14 H17 N5 O4'
_chemical_formula_weight         319.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N5O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.51038(10)
_cell_length_b                   17.3551(2)
_cell_length_c                   23.2172(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3026.21(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15729
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.3580
_cell_measurement_theta_min      4.5560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
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    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.548
_diffrn_reflns_theta_min         3.808
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00  30.00   99
  2  ω   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00 -60.00   99
  3  ω     23.00  97.00   1.00    6.05    --   41.24-125.00 -90.00   74
  4  ω     23.00  97.00   1.00    6.05    --   41.24-125.00-180.00   74
  5  ω     84.00 178.00   1.00   19.32    --  112.00  30.00  90.00   94
  6  ω     84.00 178.00   1.00   19.32    --  112.00  30.00 150.00   94
  7  ω    100.00 178.00   1.00   19.32    --  112.00 111.00   0.00   78
  8  ω    100.00 178.00   1.00   19.32    --  112.00 111.00 -30.00   78
  9  ω     36.00 145.00   1.00   19.32    --  112.00 -77.00  60.00  109
 10  ω     29.00 109.00   1.00   19.32    --  112.00 -94.00 -30.00   80
 11  ω     29.00 109.00   1.00   19.32    --  112.00 -94.00  30.00   80
 12  ω     29.00 109.00   1.00   19.32    --  112.00 -94.00 -90.00   80
 13  ω     86.00 178.00   1.00   19.32    --  112.00  45.00 -60.00   92
 14  ω     57.00 151.00   1.00   19.32    --  112.00 178.00  90.00   94
 15  ω   -117.00 -53.00   1.00    6.05    --  -41.24 -77.00 150.00   64
 16  ω   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00-180.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2006207000
_diffrn_orient_matrix_UB_12      0.0173377000
_diffrn_orient_matrix_UB_13      0.0048446000
_diffrn_orient_matrix_UB_21      0.0207491000
_diffrn_orient_matrix_UB_22      -0.0122176000
_diffrn_orient_matrix_UB_23      -0.0653848000
_diffrn_orient_matrix_UB_31      -0.0371918000
_diffrn_orient_matrix_UB_32      0.0862068000
_diffrn_orient_matrix_UB_33      -0.0102294000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6059
_reflns_number_total             6304
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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         0.183
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.3928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O006(H00A), O008(H00C)
2.b Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'A), C6'(H6'), C1'A(H1'A), C2'A(H2'C), C6'A(H6'A)
2.c Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C7'(H7'A,H7'B), C5'A(H5'D,H5'E), C7'A(H7'C,H7'D)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C2A(H2A), C8A(H8A)
2.e X=CH2 refined with riding coordinates:
 N6A(H6AA,H6AB)
2.f Idealised tetrahedral OH refined as rotating group:
 O2'(H2'), O3'(H3'), O5'(H5'), O2'A(H2'B), O5'A(H5'C)
2.g :
 C3"'(H3"'), C1(H1)
;
_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
O2' O 0.35600(15) 0.55017(7) 0.82856(5) 0.0151(2) Uani 1 1 d . . . . .
H2' H 0.3667 0.5216 0.8006 0.023 Uiso 1 1 calc GR . . . .
O3' O 0.60850(16) 0.46803(7) 0.88494(5) 0.0154(2) Uani 1 1 d . . . . .
H3' H 0.5067 0.4584 0.8955 0.023 Uiso 1 1 calc GR . . . .
O5' O 0.83383(17) 0.64141(7) 0.99670(5) 0.0195(3) Uani 1 1 d . . . . .
H5' H 0.9272 0.6265 1.0112 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.69765(19) 0.81638(8) 0.68534(6) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.5025(2) 0.73939(8) 0.74409(6) 0.0162(3) Uani 1 1 d . . . . .
N6 N 0.9607(2) 0.87048(9) 0.71855(7) 0.0198(3) Uani 1 1 d . . . . .
H6A H 1.047(3) 0.8746(14) 0.7461(11) 0.024 Uiso 1 1 d R . . . .
H6B H 0.976(4) 0.8896(15) 0.6835(12) 0.032(7) Uiso 1 1 d . . . . .
N7 N 0.8683(2) 0.79319(8) 0.83456(6) 0.0171(3) Uani 1 1 d . . . . .
N9 N 0.61428(19) 0.72531(8) 0.84187(6) 0.0148(3) Uani 1 1 d . . . . .
C1' C 0.4789(2) 0.67103(9) 0.86310(7) 0.0140(3) Uani 1 1 d . . . . .
H1' H 0.3596 0.6885 0.8520 0.017 Uiso 1 1 calc R . . . .
C2 C 0.5517(2) 0.77406(10) 0.69524(8) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.4748 0.7681 0.6642 0.021 Uiso 1 1 calc R . . . .
C2' C 0.5165(2) 0.59028(9) 0.83768(7) 0.0132(3) Uani 1 1 d . . . . .
H2'A H 0.5825 0.5950 0.8014 0.016 Uiso 1 1 calc R . . . .
C3" C 0.8222(2) 0.56242(10) 0.86859(7) 0.0171(3) Uani 1 1 d . . . . .
C3"' C 0.9680(2) 0.57452(11) 0.85075(8) 0.0231(4) Uani 1 1 d . . . . .
H3"' H 1.0820 0.5840 0.8368 0.028 Uiso 1 1 calc R . . . .
C3' C 0.6348(2) 0.54919(9) 0.88445(7) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.6223(2) 0.75156(9) 0.78635(7) 0.0143(3) Uani 1 1 d . . . . .
C4' C 0.5877(2) 0.58764(9) 0.94154(7) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.7785(2) 0.79371(9) 0.78226(7) 0.0148(3) Uani 1 1 d . . . . .
C5' C 0.7121(3) 0.57789(10) 0.99199(7) 0.0200(3) Uani 1 1 d . . . . .
H5'A H 0.6430 0.5739 1.0272 0.024 Uiso 1 1 calc R . . . .
H5'B H 0.7789 0.5304 0.9874 0.024 Uiso 1 1 calc R . . . .
C6 C 0.8155(2) 0.82780(9) 0.72851(7) 0.0155(3) Uani 1 1 d . . . . .
C6' C 0.4907(2) 0.66223(9) 0.92779(7) 0.0160(3) Uani 1 1 d . . . . .
H6' H 0.5113 0.7078 0.9518 0.019 Uiso 1 1 calc R . . . .
C7' C 0.3893(2) 0.59492(10) 0.95210(7) 0.0175(3) Uani 1 1 d . . . . .
H7'A H 0.3097 0.5673 0.9265 0.021 Uiso 1 1 calc R . . . .
H7'B H 0.3490 0.5984 0.9917 0.021 Uiso 1 1 calc R . . . .
C8 C 0.7662(2) 0.75125(9) 0.86831(7) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.7944 0.7403 0.9064 0.020 Uiso 1 1 calc R . . . .
O2'A O 0.17428(16) 0.66495(7) 0.73153(5) 0.0163(2) Uani 1 1 d . . . . .
H2'B H 0.2564 0.6918 0.7433 0.024 Uiso 1 1 calc GR . . . .
O3'A O 0.12864(18) 0.74479(7) 0.63692(6) 0.0196(3) Uani 1 1 d . . . . .
H3'A H 0.096(4) 0.7478(16) 0.6708(13) 0.038(7) Uiso 1 1 d . . . . .
O5'A O 0.00199(18) 0.56928(8) 0.51533(5) 0.0216(3) Uani 1 1 d . . . . .
H5'C H 0.0648 0.5922 0.4920 0.032 Uiso 1 1 calc GR . . . .
N1A N 0.7270(2) 0.39144(8) 0.70893(6) 0.0172(3) Uani 1 1 d . . . . .
N3A N 0.47151(19) 0.46789(8) 0.73383(6) 0.0163(3) Uani 1 1 d . . . . .
N6A N 0.7739(2) 0.33681(8) 0.61971(6) 0.0174(3) Uani 1 1 d . . . . .
H6AA H 0.8694 0.3160 0.6330 0.021 Uiso 1 1 calc R . . . .
H6AB H 0.7433 0.3291 0.5845 0.021 Uiso 1 1 calc R . . . .
N7A N 0.42489(19) 0.42284(8) 0.58411(6) 0.0162(3) Uani 1 1 d . . . . .
N9A N 0.27621(19) 0.48931(8) 0.65211(6) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.4009(3) 0.65570(12) 0.54341(8) 0.0242(4) Uani 1 1 d . . . . .
H1 H 0.4880 0.6526 0.5150 0.029 Uiso 1 1 calc R . . . .
C1'A C 0.1500(2) 0.54199(9) 0.68055(7) 0.0141(3) Uani 1 1 d . . . . .
H1'A H 0.1240 0.5241 0.7197 0.017 Uiso 1 1 calc R . . . .
C2'A C 0.2300(2) 0.62415(9) 0.68221(7) 0.0143(3) Uani 1 1 d . . . . .
H2'C H 0.3603 0.6215 0.6810 0.017 Uiso 1 1 calc R . . . .
C2A C 0.6259(2) 0.43261(10) 0.74487(7) 0.0176(3) Uani 1 1 d . . . . .
H2A H 0.6683 0.4373 0.7823 0.021 Uiso 1 1 calc R . . . .
C3"A C 0.2893(2) 0.65963(10) 0.57976(8) 0.0180(3) Uani 1 1 d . . . . .
C3'A C 0.1569(2) 0.66461(9) 0.62608(7) 0.0154(3) Uani 1 1 d . . . . .
C4'A C -0.0157(2) 0.62198(9) 0.61138(7) 0.0159(3) Uani 1 1 d . . . . .
C4A C 0.4236(2) 0.45898(9) 0.67847(7) 0.0140(3) Uani 1 1 d . . . . .
C5'A C -0.0874(2) 0.62348(11) 0.55076(8) 0.0210(4) Uani 1 1 d . . . . .
H5'D H -0.2137 0.6118 0.5514 0.025 Uiso 1 1 calc R . . . .
H5'E H -0.0727 0.6747 0.5348 0.025 Uiso 1 1 calc R . . . .
C5A C 0.5136(2) 0.41767(9) 0.63644(7) 0.0147(3) Uani 1 1 d . . . . .
C6'A C -0.0197(2) 0.54804(10) 0.64596(7) 0.0163(3) Uani 1 1 d . . . . .
H6'A H -0.0703 0.5015 0.6286 0.020 Uiso 1 1 calc R . . . .
C6A C 0.6733(2) 0.38098(9) 0.65370(7) 0.0148(3) Uani 1 1 d . . . . .
C7'A C -0.1418(2) 0.61380(10) 0.66184(8) 0.0185(3) Uani 1 1 d . . . . .
H7'C H -0.1149 0.6425 0.6966 0.022 Uiso 1 1 calc R . . . .
H7'D H -0.2676 0.6081 0.6535 0.022 Uiso 1 1 calc R . . . .
C8A C 0.2860(2) 0.46682(9) 0.59548(7) 0.0164(3) Uani 1 1 d . . . . .
H8A H 0.2029 0.4812 0.5678 0.020 Uiso 1 1 calc R . . . .
O006 O 0.29047(18) 0.39744(8) 0.91927(6) 0.0212(3) Uani 1 1 d . . . . .
H00A H 0.1799 0.4034 0.9253 0.032 Uiso 1 1 d G . . . .
H00B H 0.287(4) 0.3706(17) 0.8865(13) 0.041(8) Uiso 1 1 d . . . . .
O008 O 0.91001(19) 0.38255(8) 0.92240(7) 0.0272(3) Uani 1 1 d . . . . .
H00C H 0.8175 0.4088 0.9144 0.041 Uiso 1 1 d G . . . .
H00D H 0.894(4) 0.3372(18) 0.9081(13) 0.041(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
O2' H2' 0.8200 . ?
O2' C2' 1.4079(19) . ?
O3' H3' 0.8200 . ?
O3' C3' 1.4225(19) . ?
O5' H5' 0.8200 . ?
O5' C5' 1.436(2) . ?
N1 C2 1.340(2) . ?
N1 C6 1.352(2) . ?
N3 C2 1.336(2) . ?
N3 C4 1.348(2) . ?
N6 H6A 0.91(3) . ?
N6 H6B 0.89(3) . ?
N6 C6 1.339(2) . ?
N7 C5 1.389(2) . ?
N7 C8 1.316(2) . ?
N9 C1' 1.471(2) . ?
N9 C4 1.369(2) . ?
N9 C8 1.372(2) . ?
C1' H1' 0.9800 . ?
C1' C2' 1.547(2) . ?
C1' C6' 1.512(2) . ?
C2 H2 0.9300 . ?
C2' H2'A 0.9800 . ?
C2' C3' 1.574(2) . ?
C3" C3"' 1.189(3) . ?
C3" C3' 1.473(2) . ?
C3"' H3"' 0.9300 . ?
C3' C4' 1.525(2) . ?
C4 C5 1.386(2) . ?
C4' C5' 1.508(2) . ?
C4' C6' 1.519(2) . ?
C4' C7' 1.516(2) . ?
C5 C6 1.409(2) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C6' H6' 0.9800 . ?
C6' C7' 1.505(2) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C8 H8 0.9300 . ?
O2'A H2'B 0.8200 . ?
O2'A C2'A 1.4098(19) . ?
O3'A H3'A 0.83(3) . ?
O3'A C3'A 1.430(2) . ?
O5'A H5'C 0.8200 . ?
O5'A C5'A 1.419(2) . ?
N1A C2A 1.335(2) . ?
N1A C6A 1.356(2) . ?
N3A C2A 1.336(2) . ?
N3A C4A 1.344(2) . ?
N6A H6AA 0.8600 . ?
N6A H6AB 0.8600 . ?
N6A C6A 1.335(2) . ?
N7A C5A 1.389(2) . ?
N7A C8A 1.319(2) . ?
N9A C1'A 1.473(2) . ?
N9A C4A 1.370(2) . ?
N9A C8A 1.373(2) . ?
C1 H1 0.9300 . ?
C1 C3"A 1.192(3) . ?
C1'A H1'A 0.9800 . ?
C1'A C2'A 1.548(2) . ?
C1'A C6'A 1.510(2) . ?
C2'A H2'C 0.9800 . ?
C2'A C3'A 1.579(2) . ?
C2A H2A 0.9300 . ?
C3"A C3'A 1.467(2) . ?
C3'A C4'A 1.531(2) . ?
C4'A C5'A 1.507(2) . ?
C4'A C6'A 1.514(2) . ?
C4'A C7'A 1.513(2) . ?
C4A C5A 1.387(2) . ?
C5'A H5'D 0.9700 . ?
C5'A H5'E 0.9700 . ?
C5A C6A 1.416(2) . ?
C6'A H6'A 0.9800 . ?
C6'A C7'A 1.509(2) . ?
C7'A H7'C 0.9700 . ?
C7'A H7'D 0.9700 . ?
C8A H8A 0.9300 . ?
O006 H00A 0.8483 . ?
O006 H00B 0.89(3) . ?
O008 H00C 0.8508 . ?
O008 H00D 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' O2' H2' 109.5 . . ?
C3' O3' H3' 109.5 . . ?
C5' O5' H5' 109.5 . . ?
C2 N1 C6 119.27(15) . . ?
C2 N3 C4 111.28(14) . . ?
H6A N6 H6B 122(2) . . ?
C6 N6 H6A 120.0(15) . . ?
C6 N6 H6B 118.0(17) . . ?
C8 N7 C5 103.95(14) . . ?
C4 N9 C1' 123.99(14) . . ?
C4 N9 C8 106.01(14) . . ?
C8 N9 C1' 129.44(14) . . ?
N9 C1' H1' 110.3 . . ?
N9 C1' C2' 109.04(13) . . ?
N9 C1' C6' 110.89(13) . . ?
C2' C1' H1' 110.3 . . ?
C6' C1' H1' 110.3 . . ?
C6' C1' C2' 106.06(13) . . ?
N1 C2 H2 115.9 . . ?
N3 C2 N1 128.23(16) . . ?
N3 C2 H2 115.9 . . ?
O2' C2' C1' 110.43(13) . . ?
O2' C2' H2'A 110.2 . . ?
O2' C2' C3' 111.30(13) . . ?
C1' C2' H2'A 110.2 . . ?
C1' C2' C3' 104.50(12) . . ?
C3' C2' H2'A 110.2 . . ?
C3"' C3" C3' 173.91(18) . . ?
C3" C3"' H3"' 180.0 . . ?
O3' C3' C2' 112.06(13) . . ?
O3' C3' C3" 106.81(14) . . ?
O3' C3' C4' 113.20(13) . . ?
C3" C3' C2' 107.24(13) . . ?
C3" C3' C4' 111.76(14) . . ?
C4' C3' C2' 105.68(13) . . ?
N3 C4 N9 127.17(15) . . ?
N3 C4 C5 126.73(16) . . ?
N9 C4 C5 106.10(14) . . ?
C5' C4' C3' 118.84(15) . . ?
C5' C4' C6' 123.77(14) . . ?
C5' C4' C7' 119.51(15) . . ?
C6' C4' C3' 107.54(13) . . ?
C7' C4' C3' 113.90(14) . . ?
C7' C4' C6' 59.44(11) . . ?
N7 C5 C6 132.97(15) . . ?
C4 C5 N7 110.35(14) . . ?
C4 C5 C6 116.67(15) . . ?
O5' C5' C4' 111.55(14) . . ?
O5' C5' H5'A 109.3 . . ?
O5' C5' H5'B 109.3 . . ?
C4' C5' H5'A 109.3 . . ?
C4' C5' H5'B 109.3 . . ?
H5'A C5' H5'B 108.0 . . ?
N1 C6 C5 117.82(15) . . ?
N6 C6 N1 119.10(15) . . ?
N6 C6 C5 123.09(16) . . ?
C1' C6' C4' 108.84(13) . . ?
C1' C6' H6' 119.5 . . ?
C4' C6' H6' 119.5 . . ?
C7' C6' C1' 114.91(14) . . ?
C7' C6' C4' 60.16(11) . . ?
C7' C6' H6' 119.5 . . ?
C4' C7' H7'A 117.7 . . ?
C4' C7' H7'B 117.7 . . ?
C6' C7' C4' 60.40(11) . . ?
C6' C7' H7'A 117.7 . . ?
C6' C7' H7'B 117.7 . . ?
H7'A C7' H7'B 114.9 . . ?
N7 C8 N9 113.57(15) . . ?
N7 C8 H8 123.2 . . ?
N9 C8 H8 123.2 . . ?
C2'A O2'A H2'B 109.5 . . ?
C3'A O3'A H3'A 105.9(19) . . ?
C5'A O5'A H5'C 109.5 . . ?
C2A N1A C6A 119.55(15) . . ?
C2A N3A C4A 111.31(15) . . ?
H6AA N6A H6AB 120.0 . . ?
C6A N6A H6AA 120.0 . . ?
C6A N6A H6AB 120.0 . . ?
C8A N7A C5A 103.97(14) . . ?
C4A N9A C1'A 123.92(14) . . ?
C4A N9A C8A 105.96(14) . . ?
C8A N9A C1'A 129.79(14) . . ?
C3"A C1 H1 180.0 . . ?
N9A C1'A H1'A 110.3 . . ?
N9A C1'A C2'A 109.45(13) . . ?
N9A C1'A C6'A 110.36(13) . . ?
C2'A C1'A H1'A 110.3 . . ?
C6'A C1'A H1'A 110.3 . . ?
C6'A C1'A C2'A 106.07(13) . . ?
O2'A C2'A C1'A 111.57(13) . . ?
O2'A C2'A H2'C 110.1 . . ?
O2'A C2'A C3'A 110.11(13) . . ?
C1'A C2'A H2'C 110.1 . . ?
C1'A C2'A C3'A 104.74(13) . . ?
C3'A C2'A H2'C 110.1 . . ?
N1A C2A N3A 128.23(16) . . ?
N1A C2A H2A 115.9 . . ?
N3A C2A H2A 115.9 . . ?
C1 C3"A C3'A 177.96(18) . . ?
O3'A C3'A C2'A 109.83(13) . . ?
O3'A C3'A C3"A 106.68(14) . . ?
O3'A C3'A C4'A 112.56(13) . . ?
C3"A C3'A C2'A 110.07(14) . . ?
C3"A C3'A C4'A 112.45(14) . . ?
C4'A C3'A C2'A 105.26(13) . . ?
C5'A C4'A C3'A 120.16(15) . . ?
C5'A C4'A C6'A 120.18(15) . . ?
C5'A C4'A C7'A 120.06(15) . . ?
C6'A C4'A C3'A 107.96(13) . . ?
C7'A C4'A C3'A 113.74(14) . . ?
C7'A C4'A C6'A 59.82(11) . . ?
N3A C4A N9A 126.85(15) . . ?
N3A C4A C5A 126.98(15) . . ?
N9A C4A C5A 106.16(14) . . ?
O5'A C5'A C4'A 111.16(14) . . ?
O5'A C5'A H5'D 109.4 . . ?
O5'A C5'A H5'E 109.4 . . ?
C4'A C5'A H5'D 109.4 . . ?
C4'A C5'A H5'E 109.4 . . ?
H5'D C5'A H5'E 108.0 . . ?
N7A C5A C6A 133.09(15) . . ?
C4A C5A N7A 110.37(14) . . ?
C4A C5A C6A 116.53(15) . . ?
C1'A C6'A C4'A 108.91(13) . . ?
C1'A C6'A H6'A 119.3 . . ?
C4'A C6'A H6'A 119.3 . . ?
C7'A C6'A C1'A 115.79(14) . . ?
C7'A C6'A C4'A 60.06(11) . . ?
C7'A C6'A H6'A 119.3 . . ?
N1A C6A C5A 117.34(15) . . ?
N6A C6A N1A 117.86(15) . . ?
N6A C6A C5A 124.80(15) . . ?
C4'A C7'A H7'C 117.8 . . ?
C4'A C7'A H7'D 117.8 . . ?
C6'A C7'A C4'A 60.12(11) . . ?
C6'A C7'A H7'C 117.8 . . ?
C6'A C7'A H7'D 117.8 . . ?
H7'C C7'A H7'D 114.9 . . ?
N7A C8A N9A 113.50(15) . . ?
N7A C8A H8A 123.3 . . ?
N9A C8A H8A 123.3 . . ?
H00A O006 H00B 99.9 . . ?
H00C O008 H00D 106.7 . . ?

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
O2' C2' C3' O3' 30.52(18) . . . . ?
O2' C2' C3' C3" 147.43(13) . . . . ?
O2' C2' C3' C4' -93.21(15) . . . . ?
O3' C3' C4' C5' 74.05(19) . . . . ?
O3' C3' C4' C6' -138.87(14) . . . . ?
O3' C3' C4' C7' -75.17(18) . . . . ?
N3 C4 C5 N7 -179.68(15) . . . . ?
N3 C4 C5 C6 0.5(3) . . . . ?
N7 C5 C6 N1 179.65(17) . . . . ?
N7 C5 C6 N6 -0.3(3) . . . . ?
N9 C1' C2' O2' -147.14(13) . . . . ?
N9 C1' C2' C3' 93.08(14) . . . . ?
N9 C1' C6' C4' -101.05(15) . . . . ?
N9 C1' C6' C7' -166.13(14) . . . . ?
N9 C4 C5 N7 0.60(18) . . . . ?
N9 C4 C5 C6 -179.26(14) . . . . ?
C1' N9 C4 N3 7.1(3) . . . . ?
C1' N9 C4 C5 -173.20(14) . . . . ?
C1' N9 C8 N7 172.85(15) . . . . ?
C1' C2' C3' O3' 149.72(13) . . . . ?
C1' C2' C3' C3" -93.38(15) . . . . ?
C1' C2' C3' C4' 25.99(16) . . . . ?
C1' C6' C7' C4' 98.28(16) . . . . ?
C2 N1 C6 N6 -179.62(16) . . . . ?
C2 N1 C6 C5 0.4(2) . . . . ?
C2 N3 C4 N9 179.46(16) . . . . ?
C2 N3 C4 C5 -0.2(2) . . . . ?
C2' C1' C6' C4' 17.20(17) . . . . ?
C2' C1' C6' C7' -47.89(18) . . . . ?
C2' C3' C4' C5' -162.94(14) . . . . ?
C2' C3' C4' C6' -15.86(17) . . . . ?
C2' C3' C4' C7' 47.84(17) . . . . ?
C3" C3' C4' C5' -46.6(2) . . . . ?
C3" C3' C4' C6' 100.47(16) . . . . ?
C3" C3' C4' C7' 164.17(14) . . . . ?
C3' C4' C5' O5' 95.42(18) . . . . ?
C3' C4' C6' C1' -0.63(18) . . . . ?
C3' C4' C6' C7' 107.87(15) . . . . ?
C3' C4' C7' C6' -96.96(15) . . . . ?
C4 N3 C2 N1 0.0(3) . . . . ?
C4 N9 C1' C2' 71.55(19) . . . . ?
C4 N9 C1' C6' -172.03(14) . . . . ?
C4 N9 C8 N7 1.35(19) . . . . ?
C4 C5 C6 N1 -0.5(2) . . . . ?
C4 C5 C6 N6 179.49(16) . . . . ?
C5 N7 C8 N9 -0.96(19) . . . . ?
C5' C4' C6' C1' 144.43(16) . . . . ?
C5' C4' C6' C7' -107.07(18) . . . . ?
C5' C4' C7' C6' 114.04(17) . . . . ?
C6 N1 C2 N3 -0.2(3) . . . . ?
C6' C1' C2' O2' 93.40(15) . . . . ?
C6' C1' C2' C3' -26.39(16) . . . . ?
C6' C4' C5' O5' -46.0(2) . . . . ?
C7' C4' C5' O5' -117.10(17) . . . . ?
C7' C4' C6' C1' -108.50(15) . . . . ?
C8 N7 C5 C4 0.20(19) . . . . ?
C8 N7 C5 C6 -179.98(18) . . . . ?
C8 N9 C1' C2' -98.59(19) . . . . ?
C8 N9 C1' C6' 17.8(2) . . . . ?
C8 N9 C4 N3 179.16(16) . . . . ?
C8 N9 C4 C5 -1.12(17) . . . . ?
O2'A C2'A C3'A O3'A 26.21(18) . . . . ?
O2'A C2'A C3'A C3"A 143.38(14) . . . . ?
O2'A C2'A C3'A C4'A -95.20(15) . . . . ?
O3'A C3'A C4'A C5'A 82.93(19) . . . . ?
O3'A C3'A C4'A C6'A -133.99(14) . . . . ?
O3'A C3'A C4'A C7'A -69.76(18) . . . . ?
N3A C4A C5A N7A -178.92(16) . . . . ?
N3A C4A C5A C6A -0.1(3) . . . . ?
N7A C5A C6A N1A 176.44(17) . . . . ?
N7A C5A C6A N6A -3.8(3) . . . . ?
N9A C1'A C2'A O2'A -148.07(13) . . . . ?
N9A C1'A C2'A C3'A 92.83(15) . . . . ?
N9A C1'A C6'A C4'A -100.56(15) . . . . ?
N9A C1'A C6'A C7'A -165.70(14) . . . . ?
N9A C4A C5A N7A 0.75(18) . . . . ?
N9A C4A C5A C6A 179.62(14) . . . . ?
C1'A N9A C4A N3A 4.1(3) . . . . ?
C1'A N9A C4A C5A -175.53(14) . . . . ?
C1'A N9A C8A N7A 175.42(15) . . . . ?
C1'A C2'A C3'A O3'A 146.30(13) . . . . ?
C1'A C2'A C3'A C3"A -96.53(15) . . . . ?
C1'A C2'A C3'A C4'A 24.88(16) . . . . ?
C1'A C6'A C7'A C4'A 97.87(15) . . . . ?
C2'A C1'A C6'A C4'A 17.89(17) . . . . ?
C2'A C1'A C6'A C7'A -47.25(18) . . . . ?
C2'A C3'A C4'A C5'A -157.46(14) . . . . ?
C2'A C3'A C4'A C6'A -14.37(17) . . . . ?
C2'A C3'A C4'A C7'A 49.85(17) . . . . ?
C2A N1A C6A N6A -177.23(16) . . . . ?
C2A N1A C6A C5A 2.5(2) . . . . ?
C2A N3A C4A N9A -177.94(16) . . . . ?
C2A N3A C4A C5A 1.7(2) . . . . ?
C3"A C3'A C4'A C5'A -37.6(2) . . . . ?
C3"A C3'A C4'A C6'A 105.48(16) . . . . ?
C3"A C3'A C4'A C7'A 169.71(14) . . . . ?
C3'A C4'A C5'A O5'A 80.55(19) . . . . ?
C3'A C4'A C6'A C1'A -1.96(18) . . . . ?
C3'A C4'A C6'A C7'A 107.52(15) . . . . ?
C3'A C4'A C7'A C6'A -97.69(15) . . . . ?
C4A N3A C2A N1A -1.2(3) . . . . ?
C4A N9A C1'A C2'A 78.46(18) . . . . ?
C4A N9A C1'A C6'A -165.17(14) . . . . ?
C4A N9A C8A N7A 1.85(19) . . . . ?
C4A C5A C6A N1A -2.1(2) . . . . ?
C4A C5A C6A N6A 177.64(16) . . . . ?
C5'A C4'A C6'A C1'A 141.11(15) . . . . ?
C5'A C4'A C6'A C7'A -109.40(17) . . . . ?
C5'A C4'A C7'A C6'A 109.59(17) . . . . ?
C5A N7A C8A N9A -1.35(19) . . . . ?
C6'A C1'A C2'A O2'A 92.88(15) . . . . ?
C6'A C1'A C2'A C3'A -26.22(16) . . . . ?
C6'A C4'A C5'A O5'A -58.1(2) . . . . ?
C6A N1A C2A N3A -0.8(3) . . . . ?
C7'A C4'A C5'A O5'A -128.48(16) . . . . ?
C7'A C4'A C6'A C1'A -109.48(15) . . . . ?
C8A N7A C5A C4A 0.34(18) . . . . ?
C8A N7A C5A C6A -178.27(18) . . . . ?
C8A N9A C1'A C2'A -94.08(19) . . . . ?
C8A N9A C1'A C6'A 22.3(2) . . . . ?
C8A N9A C4A N3A 178.18(16) . . . . ?
C8A N9A C4A C5A -1.49(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.764
