# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_130227b_0m
_database_code_depnum_ccdc_archive 'CCDC 930816'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Compound 10'
_chemical_name_common            ?
_chemical_melting_point          494-496
_chemical_formula_moiety         'C11 H13 N5 O4'
_chemical_formula_sum            'C11 H13 N5 O4'
_chemical_formula_weight         279.26
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'


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

_cell_length_a                   7.4773(10)
_cell_length_b                   8.2931(11)
_cell_length_c                   20.419(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1266.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7409
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      31.62

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   'SADABS, Sheldrick,2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12797
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3689
_reflns_number_gt                3413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0709P)²+0.0802P] 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     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85266(19) -0.40630(15) -0.12529(6) 0.0361(3) Uani 1 1 d . . .
H1 H 0.8396 -0.5168 -0.1190 0.043 Uiso 1 1 calc R . .
C2 C 0.94824(17) -0.20401(14) -0.19524(5) 0.0304(2) Uani 1 1 d . . .
C3 C 0.89345(16) -0.09335(14) -0.14694(5) 0.0284(2) Uani 1 1 d . . .
C4 C 0.82066(15) -0.15748(14) -0.08986(5) 0.0273(2) Uani 1 1 d . . .
C5 C 0.8297(2) 0.10594(15) -0.08535(6) 0.0368(3) Uani 1 1 d . . .
H5 H 0.8182 0.2101 -0.0690 0.044 Uiso 1 1 calc R . .
C6 C 0.72557(19) -0.03808(15) 0.01662(5) 0.0335(2) Uani 1 1 d . . .
H6 H 0.6569 -0.1360 0.0260 0.040 Uiso 1 1 calc R . .
C7 C 0.8772(2) -0.00897(16) 0.06743(6) 0.0373(3) Uani 1 1 d . . .
H7 H 0.8902 -0.0960 0.0995 0.045 Uiso 1 1 calc R . .
C8 C 0.75757(18) 0.13088(16) 0.09086(6) 0.0360(3) Uani 1 1 d . . .
H8 H 0.7011 0.1054 0.1329 0.043 Uiso 1 1 calc R . .
C9 C 0.8278(2) 0.30048(17) 0.09024(7) 0.0410(3) Uani 1 1 d . . .
H9A H 0.9186 0.3130 0.0567 0.049 Uiso 1 1 calc R . .
H9B H 0.7319 0.3764 0.0817 0.049 Uiso 1 1 calc R . .
C10 C 0.9324(3) 0.4807(2) 0.17206(10) 0.0587(5) Uani 1 1 d . . .
C11 C 1.0050(4) 0.4891(3) 0.24042(11) 0.0834(8) Uani 1 1 d . . .
H11A H 0.9077 0.4940 0.2710 0.125 Uiso 1 1 calc R . .
H11B H 1.0780 0.5837 0.2450 0.125 Uiso 1 1 calc R . .
H11C H 1.0759 0.3949 0.2491 0.125 Uiso 1 1 calc R . .
N1 N 0.79482(16) -0.31429(13) -0.07637(5) 0.0334(2) Uani 1 1 d . . .
N2 N 0.92662(17) -0.36296(12) -0.18199(5) 0.0364(2) Uani 1 1 d . . .
N3 N 1.0182(2) -0.16383(14) -0.25280(5) 0.0423(3) Uani 1 1 d . . .
H3A H 1.0481 -0.2377 -0.2802 0.051 Uiso 1 1 calc R . .
H3B H 1.0335 -0.0639 -0.2626 0.051 Uiso 1 1 calc R . .
N4 N 0.89643(18) 0.07411(13) -0.14350(5) 0.0351(2) Uani 1 1 d . . .
N5 N 0.77866(15) -0.02829(12) -0.05117(5) 0.0310(2) Uani 1 1 d . . .
O1 O 1.03849(14) 0.04146(14) 0.03995(6) 0.0464(3) Uani 1 1 d . . .
H1A H 1.1114 -0.0323 0.0417 0.070 Uiso 1 1 calc R . .
O2 O 0.63363(13) 0.10460(13) 0.03649(4) 0.0386(2) Uani 1 1 d . . .
O3 O 0.9032(2) 0.32766(15) 0.15438(6) 0.0554(3) Uani 1 1 d . . .
O4 O 0.9055(3) 0.5921(2) 0.13678(10) 0.0891(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3292(16) . ?
C1 N2 1.3325(15) . ?
C1 H1 0.9300 . ?
C2 N3 1.3288(15) . ?
C2 N2 1.3554(15) . ?
C2 C3 1.4081(15) . ?
C3 N4 1.3907(15) . ?
C3 C4 1.3919(15) . ?
C4 N1 1.3433(15) . ?
C4 N5 1.3677(15) . ?
C5 N4 1.3147(16) . ?
C5 N5 1.3681(15) . ?
C5 H5 0.9300 . ?
C6 O2 1.4273(16) . ?
C6 N5 1.4424(14) . ?
C6 C7 1.5558(19) . ?
C6 H6 0.9800 . ?
C7 O1 1.3943(18) . ?
C7 C8 1.5409(19) . ?
C7 H7 0.9800 . ?
C8 O2 1.4626(16) . ?
C8 C9 1.5014(19) . ?
C8 H8 0.9800 . ?
C9 O3 1.4435(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O4 1.189(3) . ?
C10 O3 1.338(2) . ?
C10 C11 1.499(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1 H1A 0.8200 . ?

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
N1 C1 N2 129.28(12) . . ?
N1 C1 H1 115.4 . . ?
N2 C1 H1 115.4 . . ?
N3 C2 N2 117.87(10) . . ?
N3 C2 C3 124.79(11) . . ?
N2 C2 C3 117.34(10) . . ?
N4 C3 C4 110.21(10) . . ?
N4 C3 C2 132.97(11) . . ?
C4 C3 C2 116.82(10) . . ?
N1 C4 N5 127.37(10) . . ?
N1 C4 C3 126.72(10) . . ?
N5 C4 C3 105.91(10) . . ?
N4 C5 N5 113.78(11) . . ?
N4 C5 H5 123.1 . . ?
N5 C5 H5 123.1 . . ?
O2 C6 N5 111.02(10) . . ?
O2 C6 C7 91.88(9) . . ?
N5 C6 C7 115.51(11) . . ?
O2 C6 H6 112.3 . . ?
N5 C6 H6 112.3 . . ?
C7 C6 H6 112.3 . . ?
O1 C7 C8 113.66(11) . . ?
O1 C7 C6 114.11(10) . . ?
C8 C7 C6 84.30(10) . . ?
O1 C7 H7 113.8 . . ?
C8 C7 H7 113.8 . . ?
C6 C7 H7 113.8 . . ?
O2 C8 C9 110.79(11) . . ?
O2 C8 C7 91.15(9) . . ?
C9 C8 C7 119.96(12) . . ?
O2 C8 H8 111.1 . . ?
C9 C8 H8 111.1 . . ?
C7 C8 H8 111.1 . . ?
O3 C9 C8 105.98(11) . . ?
O3 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
O3 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O4 C10 O3 123.12(19) . . ?
O4 C10 C11 126.1(2) . . ?
O3 C10 C11 110.7(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C4 110.79(10) . . ?
C1 N2 C2 119.04(10) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C5 N4 C3 103.89(10) . . ?
C4 N5 C5 106.18(9) . . ?
C4 N5 C6 124.99(10) . . ?
C5 N5 C6 127.74(10) . . ?
C7 O1 H1A 109.5 . . ?
C6 O2 C8 91.95(9) . . ?
C10 O3 C9 117.18(15) . . ?

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
N3 C2 C3 N4 -1.0(2) . . . . ?
N2 C2 C3 N4 179.49(14) . . . . ?
N3 C2 C3 C4 179.12(13) . . . . ?
N2 C2 C3 C4 -0.40(18) . . . . ?
N4 C3 C4 N1 179.08(12) . . . . ?
C2 C3 C4 N1 -1.01(19) . . . . ?
N4 C3 C4 N5 0.02(15) . . . . ?
C2 C3 C4 N5 179.94(11) . . . . ?
O2 C6 C7 O1 -107.14(12) . . . . ?
N5 C6 C7 O1 7.27(16) . . . . ?
O2 C6 C7 C8 6.26(9) . . . . ?
N5 C6 C7 C8 120.67(11) . . . . ?
O1 C7 C8 O2 107.75(11) . . . . ?
C6 C7 C8 O2 -6.11(9) . . . . ?
O1 C7 C8 C9 -7.17(17) . . . . ?
C6 C7 C8 C9 -121.02(12) . . . . ?
O2 C8 C9 O3 163.51(11) . . . . ?
C7 C8 C9 O3 -92.40(14) . . . . ?
N2 C1 N1 C4 -0.5(2) . . . . ?
N5 C4 N1 C1 -179.75(12) . . . . ?
C3 C4 N1 C1 1.39(19) . . . . ?
N1 C1 N2 C2 -0.8(2) . . . . ?
N3 C2 N2 C1 -178.34(13) . . . . ?
C3 C2 N2 C1 1.22(19) . . . . ?
N5 C5 N4 C3 -1.70(17) . . . . ?
C4 C3 N4 C5 0.99(16) . . . . ?
C2 C3 N4 C5 -178.91(14) . . . . ?
N1 C4 N5 C5 179.96(13) . . . . ?
C3 C4 N5 C5 -1.00(14) . . . . ?
N1 C4 N5 C6 11.1(2) . . . . ?
C3 C4 N5 C6 -169.85(12) . . . . ?
N4 C5 N5 C4 1.76(16) . . . . ?
N4 C5 N5 C6 170.21(13) . . . . ?
O2 C6 N5 C4 -159.97(11) . . . . ?
C7 C6 N5 C4 97.18(14) . . . . ?
O2 C6 N5 C5 33.61(19) . . . . ?
C7 C6 N5 C5 -69.24(18) . . . . ?
N5 C6 O2 C8 -124.89(11) . . . . ?
C7 C6 O2 C8 -6.57(9) . . . . ?
C9 C8 O2 C6 129.45(11) . . . . ?
C7 C8 O2 C6 6.63(10) . . . . ?
O4 C10 O3 C9 -2.9(3) . . . . ?
C11 C10 O3 C9 178.15(16) . . . . ?
C8 C9 O3 C10 -163.03(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.82 2.00 2.7885(15) 161.1 2_545
N3 H3B N2 0.86 2.04 2.8582(16) 159.6 3_754
N3 H3A N4 0.86 2.24 3.1008(15) 175.0 3_744

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'CH2Cl2, CH3OH'
_chemical_compound_source        synthesis
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_140612d_0m
_database_code_depnum_ccdc_archive 'CCDC 1058189'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1R,3S-albucidin
_chemical_name_common            ?
_chemical_melting_point          439-441
_chemical_formula_moiety         'C9 H3 D8 N5 O2, D2 O'
_chemical_formula_sum            'C9 H3 D10 N5 O3'
_chemical_formula_weight         249.30
_chemical_absolute_configuration ad

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'
D D 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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)2(1)2
_symmetry_space_group_name_Hall  'P 4nw 2abw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   5.94120(10)
_cell_length_b                   5.94120(10)
_cell_length_c                   60.1040(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2121.54(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      5.15
_cell_measurement_theta_max      70.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_process_details   'SADABS, Sheldrick,2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26882
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         71.21
_reflns_number_total             2041
_reflns_number_gt                2040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1053P)²+1.9508P] 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   0.0(2)
_refine_ls_number_reflns         2041
_refine_ls_number_parameters     169
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   0.581
_refine_ls_restrained_S_all      0.580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4362(3) 0.5047(2) 0.03555(2) 0.0230(3) Uani 1 1 d . . .
H1 D 0.3446 0.3747 0.0372 0.028 Uiso 1 1 calc R . .
C2 C 0.7309(2) 0.7048(2) 0.04533(2) 0.0166(3) Uani 1 1 d . . .
C3 C 0.6930(2) 0.8632(2) 0.02887(2) 0.0169(3) Uani 1 1 d . . .
C4 C 0.4995(2) 0.8318(2) 0.01556(2) 0.0187(3) Uani 1 1 d . . .
C5 C 0.9849(2) 0.9725(2) 0.04629(2) 0.0207(3) Uani 1 1 d . . .
H5 D 1.1107 1.0589 0.0510 0.025 Uiso 1 1 calc R . .
C6 C 0.9910(2) 0.6828(2) 0.07765(2) 0.0183(3) Uani 1 1 d . . .
H6 D 0.9607 0.5174 0.0784 0.022 Uiso 1 1 calc R . .
C7 C 1.2254(2) 0.7380(2) 0.08656(2) 0.0175(3) Uani 1 1 d . . .
H7A D 1.3049 0.8584 0.0783 0.021 Uiso 1 1 calc R . .
H7B D 1.3232 0.6053 0.0889 0.021 Uiso 1 1 calc R . .
C8 C 1.1008(2) 0.8190(2) 0.10752(2) 0.0178(3) Uani 1 1 d . . .
H8 D 1.1124 0.7056 0.1198 0.021 Uiso 1 1 calc R . .
C9 C 1.1400(3) 1.0530(2) 0.11617(2) 0.0208(3) Uani 1 1 d . . .
H9A D 1.0167 1.0930 0.1265 0.025 Uiso 1 1 calc R . .
H9B D 1.2827 1.0555 0.1247 0.025 Uiso 1 1 calc R . .
N1 N 0.4317(2) 0.9738(2) -0.00026(2) 0.0214(3) Uani 1 1 d D . .
H1A H 0.514(3) 1.089(2) -0.0035(3) 0.032 Uiso 1 1 d D . .
H1B H 0.317(2) 0.940(3) -0.0085(3) 0.032 Uiso 1 1 d D . .
N2 N 0.3726(2) 0.6467(2) 0.019535(19) 0.0221(3) Uani 1 1 d . . .
N3 N 0.6089(2) 0.51899(19) 0.049466(18) 0.0194(3) Uani 1 1 d . . .
N4 N 0.8568(2) 1.0302(2) 0.029580(19) 0.0200(3) Uani 1 1 d . . .
N5 N 0.9206(2) 0.77437(19) 0.056489(18) 0.0174(3) Uani 1 1 d . . .
O1 O 0.88322(17) 0.80053(17) 0.095919(15) 0.0208(2) Uani 1 1 d . . .
O2 O 1.15093(19) 1.21766(17) 0.098975(18) 0.0247(2) Uani 1 1 d D . .
H2 H 1.282(2) 1.216(4) 0.0941(3) 0.037 Uiso 1 1 d D . .
O3 O 0.57285(19) 0.1715(2) 0.081042(18) 0.0269(3) Uani 1 1 d D . .
D3A D 0.617(3) 0.268(3) 0.0721(3) 0.040 Uiso 1 1 d D . .
D3B D 0.682(3) 0.095(3) 0.0851(3) 0.040 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
C1 N3 1.3264(18) . ?
C1 N2 1.3347(19) . ?
C1 H1 0.9500 . ?
C2 N3 1.3438(17) . ?
C2 N5 1.3749(17) . ?
C2 C3 1.3840(18) . ?
C3 N4 1.3903(19) . ?
C3 C4 1.4131(19) . ?
C4 N1 1.3336(18) . ?
C4 N2 1.3548(19) . ?
C5 N4 1.3059(18) . ?
C5 N5 1.3812(17) . ?
C5 H5 0.9500 . ?
C6 N5 1.4452(16) . ?
C6 O1 1.4512(17) . ?
C6 C7 1.5279(18) . ?
C6 H6 1.0000 . ?
C7 C8 1.5383(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.4727(16) . ?
C8 C9 1.5027(19) . ?
C8 H8 1.0000 . ?
C9 O2 1.4246(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 H1A 0.865(9) . ?
N1 H1B 0.868(9) . ?
O2 H2 0.833(10) . ?
O3 D3A 0.830(9) . ?
O3 D3B 0.828(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
N3 C1 N2 129.31(13) . . ?
N3 C1 H1 115.3 . . ?
N2 C1 H1 115.3 . . ?
N3 C2 N5 126.79(12) . . ?
N3 C2 C3 127.10(13) . . ?
N5 C2 C3 106.11(12) . . ?
C2 C3 N4 110.47(12) . . ?
C2 C3 C4 116.57(13) . . ?
N4 C3 C4 132.92(13) . . ?
N1 C4 N2 118.10(12) . . ?
N1 C4 C3 124.48(13) . . ?
N2 C4 C3 117.41(12) . . ?
N4 C5 N5 113.82(13) . . ?
N4 C5 H5 123.1 . . ?
N5 C5 H5 123.1 . . ?
N5 C6 O1 110.88(11) . . ?
N5 C6 C7 119.45(11) . . ?
O1 C6 C7 91.91(10) . . ?
N5 C6 H6 111.0 . . ?
O1 C6 H6 111.0 . . ?
C7 C6 H6 111.0 . . ?
C6 C7 C8 85.15(10) . . ?
C6 C7 H7A 114.5 . . ?
C8 C7 H7A 114.5 . . ?
C6 C7 H7B 114.5 . . ?
C8 C7 H7B 114.5 . . ?
H7A C7 H7B 111.6 . . ?
O1 C8 C9 111.64(11) . . ?
O1 C8 C7 90.67(10) . . ?
C9 C8 C7 119.88(11) . . ?
O1 C8 H8 111.0 . . ?
C9 C8 H8 111.0 . . ?
C7 C8 H8 111.0 . . ?
O2 C9 C8 113.03(11) . . ?
O2 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
O2 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
H1A N1 H1B 119.8(18) . . ?
H1A N1 C4 119.6(13) . . ?
H1B N1 C4 120.0(13) . . ?
C1 N2 C4 118.85(12) . . ?
C1 N3 C2 110.68(11) . . ?
C5 N4 C3 104.12(12) . . ?
C2 N5 C5 105.46(11) . . ?
C2 N5 C6 123.60(11) . . ?
C5 N5 C6 129.15(12) . . ?
C6 O1 C8 90.39(9) . . ?
H2 O2 C9 106.8(15) . . ?
D3A O3 D3B 108.9(17) . . ?

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
N3 C2 C3 N4 -179.19(13) . . . . ?
N5 C2 C3 N4 0.18(15) . . . . ?
N3 C2 C3 C4 3.0(2) . . . . ?
N5 C2 C3 C4 -177.67(11) . . . . ?
C2 C3 C4 N1 176.54(13) . . . . ?
N4 C3 C4 N1 -0.7(2) . . . . ?
C2 C3 C4 N2 -2.10(18) . . . . ?
N4 C3 C4 N2 -179.34(14) . . . . ?
N5 C6 C7 C8 125.58(13) . . . . ?
O1 C6 C7 C8 10.21(9) . . . . ?
C6 C7 C8 O1 -10.05(9) . . . . ?
C6 C7 C8 C9 -125.66(13) . . . . ?
O1 C8 C9 O2 -62.38(15) . . . . ?
C7 C8 C9 O2 41.65(17) . . . . ?
N2 C4 N1 H1A -177.0(15) . . . . ?
C3 C4 N1 H1A 4.4(15) . . . . ?
N2 C4 N1 H1B -6.0(15) . . . . ?
C3 C4 N1 H1B 175.4(15) . . . . ?
N3 C1 N2 C4 2.5(2) . . . . ?
N1 C4 N2 C1 -178.97(13) . . . . ?
C3 C4 N2 C1 -0.25(19) . . . . ?
N2 C1 N3 C2 -1.8(2) . . . . ?
N5 C2 N3 C1 179.66(13) . . . . ?
C3 C2 N3 C1 -1.1(2) . . . . ?
N5 C5 N4 C3 1.50(16) . . . . ?
C2 C3 N4 C5 -1.01(16) . . . . ?
C4 C3 N4 C5 176.36(14) . . . . ?
N3 C2 N5 C5 -179.94(14) . . . . ?
C3 C2 N5 C5 0.69(14) . . . . ?
N3 C2 N5 C6 -14.0(2) . . . . ?
C3 C2 N5 C6 166.68(12) . . . . ?
N4 C5 N5 C2 -1.43(16) . . . . ?
N4 C5 N5 C6 -166.36(13) . . . . ?
O1 C6 N5 C2 -86.71(15) . . . . ?
C7 C6 N5 C2 168.43(12) . . . . ?
O1 C6 N5 C5 75.78(17) . . . . ?
C7 C6 N5 C5 -29.1(2) . . . . ?
N5 C6 O1 C8 -133.27(11) . . . . ?
C7 C6 O1 C8 -10.63(10) . . . . ?
C9 C8 O1 C6 133.28(11) . . . . ?
C7 C8 O1 C6 10.55(10) . . . . ?
C8 C9 O2 H2 -83.2(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        71.21
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'CH2Cl2, CH3OH'
_chemical_compound_source        synthesis
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_150423n_0m
_database_code_depnum_ccdc_archive 'CCDC 1062963'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1S,3R-albucidin
_chemical_name_common            ?
_chemical_melting_point          435-437
_chemical_formula_moiety         'C9 H11 N5 O2, D2 O'
_chemical_formula_sum            'C9 H11 D2 N5 O3'
_chemical_formula_weight         241.26
_chemical_absolute_configuration ad

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'
D D 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           Tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+3/4'
'-y+1/2, x+1/2, z+1/4'

_cell_length_a                   5.9872(9)
_cell_length_b                   5.9872(9)
_cell_length_c                   60.571(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2171.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9353
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS, Sheldrick,2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14110
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       74
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2149
_reflns_number_gt                2122
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+6.5332P] 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     SHELXL
_refine_ls_extinction_coef       0.0103(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(5)
_refine_ls_number_reflns         2149
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1836
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.193
_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
C1 C 0.4991(9) 0.5822(10) 0.21436(8) 0.0484(14) Uani 1 1 d . . .
H1 H 0.3691(9) 0.6737(10) 0.21269(8) 0.058 Uiso 1 1 d R . .
C2 C 0.7000(8) 0.2933(8) 0.20467(7) 0.0325(10) Uani 1 1 d . . .
C3 C 0.8532(8) 0.3274(8) 0.22107(7) 0.0318(10) Uani 1 1 d . . .
C4 C 0.8195(9) 0.5177(9) 0.23457(8) 0.0393(11) Uani 1 1 d . . .
C5 C 0.9655(9) 0.0417(9) 0.20364(8) 0.0441(13) Uani 1 1 d . . .
H5 H 1.0519(9) -0.0842(9) 0.19894(8) 0.053 Uiso 1 1 d R . .
C6 C 0.6826(9) 0.0336(8) 0.17262(8) 0.0390(11) Uani 1 1 d . . .
H6 H 0.5173(9) 0.0640(8) 0.17184(8) 0.047 Uiso 1 1 d R . .
C7 C 0.7358(8) -0.1970(8) 0.16364(8) 0.0358(11) Uani 1 1 d . . .
H7A H 0.6030(8) -0.2948(8) 0.16128(8) 0.043 Uiso 1 1 d R . .
H7B H 0.8562(8) -0.2765(8) 0.17190(8) 0.043 Uiso 1 1 d R . .
C8 C 0.8199(8) -0.0740(8) 0.14297(7) 0.0356(11) Uani 1 1 d . . .
H8 H 0.7065(8) -0.0855(8) 0.13073(7) 0.043 Uiso 1 1 d R . .
C9 C 1.0505(9) -0.1139(10) 0.13473(8) 0.0467(13) Uani 1 1 d . . .
H9A H 1.0529(9) -0.2566(10) 0.12623(8) 0.056 Uiso 1 1 d R . .
H9B H 1.0905(9) 0.0094(10) 0.12438(8) 0.056 Uiso 1 1 d R . .
N1 N 0.9576(9) 0.5800(8) 0.25045(8) 0.0476(12) Uani 1 1 d . . .
H1A H 1.110(10) 0.480(10) 0.2509(9) 0.057 Uiso 1 1 d . . .
H1B H 0.926(10) 0.694(10) 0.2573(9) 0.057 Uiso 1 1 d . . .
N2 N 0.6357(8) 0.6412(8) 0.23040(7) 0.0477(12) Uani 1 1 d . . .
N3 N 0.5153(7) 0.4139(7) 0.20039(7) 0.0416(10) Uani 1 1 d . . .
N4 N 1.0200(7) 0.1670(7) 0.22041(6) 0.0408(11) Uani 1 1 d . . .
N5 N 0.7719(7) 0.1061(7) 0.19318(6) 0.0365(10) Uani 1 1 d . . .
O1 O 0.7973(7) 0.1405(6) 0.15427(5) 0.0464(9) Uani 1 1 d . . .
O2 O 1.2116(7) -0.1267(8) 0.15161(7) 0.0618(12) Uani 1 1 d . . .
H2 H 1.208(14) -0.244(14) 0.1589(12) 0.093 Uiso 1 1 d . . .
O3 O 0.1730(8) 0.4487(8) 0.16856(8) 0.0655(13) Uani 1 1 d D . .
D3A D 0.271(8) 0.423(11) 0.1777(9) 0.098 Uiso 1 1 d D . .
D3B D 0.091(10) 0.340(7) 0.1670(12) 0.098 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
C1 H1 0.9570 . ?
C1 N2 1.318(6) . ?
C1 N3 1.319(6) . ?
C2 N3 1.345(6) . ?
C2 C3 1.367(6) . ?
C2 N5 1.387(6) . ?
C3 N4 1.385(6) . ?
C3 C4 1.416(7) . ?
C4 N1 1.322(6) . ?
C4 N2 1.349(7) . ?
C5 H5 0.9566 . ?
C5 N4 1.303(6) . ?
C5 N5 1.376(6) . ?
C6 H6 1.0077 . ?
C6 N5 1.422(6) . ?
C6 O1 1.454(6) . ?
C6 C7 1.516(7) . ?
C7 H7A 0.9973 . ?
C7 H7B 0.9974 . ?
C7 C8 1.537(7) . ?
C8 H8 1.0078 . ?
C8 O1 1.460(5) . ?
C8 C9 1.487(7) . ?
C9 H9A 0.9967 . ?
C9 H9B 0.9970 . ?
C9 O2 1.408(6) . ?
N1 H1B 0.82(6) . ?
N1 H1A 1.09(6) . ?
O2 H2 0.83(8) . ?
O3 D3A 0.821(10) . ?
O3 D3B 0.819(10) . ?

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
H1 C1 N2 115.4(3) . . ?
H1 C1 N3 115.4(3) . . ?
N2 C1 N3 129.2(5) . . ?
N3 C2 C3 127.7(4) . . ?
N3 C2 N5 126.2(4) . . ?
C3 C2 N5 106.1(4) . . ?
C2 C3 N4 111.1(4) . . ?
C2 C3 C4 116.3(4) . . ?
N4 C3 C4 132.5(4) . . ?
N1 C4 N2 119.5(5) . . ?
N1 C4 C3 123.9(5) . . ?
N2 C4 C3 116.6(4) . . ?
H5 C5 N4 123.3(3) . . ?
H5 C5 N5 122.6(3) . . ?
N4 C5 N5 114.1(5) . . ?
H6 C6 N5 110.8(3) . . ?
H6 C6 O1 110.4(2) . . ?
N5 C6 O1 111.0(4) . . ?
H6 C6 C7 110.7(3) . . ?
N5 C6 C7 120.8(4) . . ?
O1 C6 C7 91.5(4) . . ?
H7A C7 H7B 111.6 . . ?
H7A C7 C6 114.7(3) . . ?
H7B C7 C6 113.9(3) . . ?
H7A C7 C8 115.1(2) . . ?
H7B C7 C8 113.6(3) . . ?
C6 C7 C8 85.7(4) . . ?
H8 C8 O1 110.0(2) . . ?
H8 C8 C9 111.6(2) . . ?
O1 C8 C9 112.6(4) . . ?
H8 C8 C7 110.2(2) . . ?
O1 C8 C7 90.5(3) . . ?
C9 C8 C7 120.0(4) . . ?
H9A C9 H9B 107.7 . . ?
H9A C9 O2 108.6(3) . . ?
H9B C9 O2 109.4(3) . . ?
H9A C9 C8 108.9(3) . . ?
H9B C9 C8 108.4(3) . . ?
O2 C9 C8 113.7(4) . . ?
H1B N1 H1A 129(5) . . ?
H1B N1 C4 118(4) . . ?
H1A N1 C4 113(3) . . ?
C1 N2 C4 119.8(5) . . ?
C1 N3 C2 110.2(4) . . ?
C5 N4 C3 103.9(4) . . ?
C5 N5 C2 104.8(4) . . ?
C5 N5 C6 129.4(4) . . ?
C2 N5 C6 124.6(4) . . ?
C6 O1 C8 90.9(3) . . ?
H2 O2 C9 115(6) . . ?
D3A O3 D3B 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N4 179.3(5) . . . . ?
N5 C2 C3 N4 -0.3(6) . . . . ?
N3 C2 C3 C4 -3.0(8) . . . . ?
N5 C2 C3 C4 177.4(4) . . . . ?
C2 C3 C4 N1 -176.8(5) . . . . ?
N4 C3 C4 N1 0.2(9) . . . . ?
C2 C3 C4 N2 2.3(7) . . . . ?
N4 C3 C4 N2 179.3(5) . . . . ?
H6 C6 C7 H7A -11.9(2) . . . . ?
N5 C6 C7 H7A 120.0(4) . . . . ?
O1 C6 C7 H7A -124.4(2) . . . . ?
H6 C6 C7 H7B -142.2(6) . . . . ?
N5 C6 C7 H7B -10.4(5) . . . . ?
O1 C6 C7 H7B 105.3(2) . . . . ?
H6 C6 C7 C8 103.9(2) . . . . ?
N5 C6 C7 C8 -124.3(5) . . . . ?
O1 C6 C7 C8 -8.6(3) . . . . ?
H7A C7 C8 H8 12.3(2) . . . . ?
H7B C7 C8 H8 142.7(6) . . . . ?
C6 C7 C8 H8 -103.0(3) . . . . ?
H7A C7 C8 O1 123.9(2) . . . . ?
H7B C7 C8 O1 -105.6(3) . . . . ?
C6 C7 C8 O1 8.6(3) . . . . ?
H7A C7 C8 C9 -119.4(4) . . . . ?
H7B C7 C8 C9 11.0(5) . . . . ?
C6 C7 C8 C9 125.3(5) . . . . ?
H8 C8 C9 H9A -51.4(2) . . . . ?
O1 C8 C9 H9A -175.8(2) . . . . ?
C7 C8 C9 H9A 79.7(4) . . . . ?
H8 C8 C9 H9B 65.50(18) . . . . ?
O1 C8 C9 H9B -58.8(3) . . . . ?
C7 C8 C9 H9B -163.4(3) . . . . ?
H8 C8 C9 O2 -172.6(3) . . . . ?
O1 C8 C9 O2 63.0(6) . . . . ?
C7 C8 C9 O2 -41.5(7) . . . . ?
N2 C4 N1 H1B 0(5) . . . . ?
C3 C4 N1 H1B 179(5) . . . . ?
N2 C4 N1 H1A -173(3) . . . . ?
C3 C4 N1 H1A 6(3) . . . . ?
H1 C1 N2 C4 177.6(4) . . . . ?
N3 C1 N2 C4 -1.8(10) . . . . ?
N1 C4 N2 C1 178.9(6) . . . . ?
C3 C4 N2 C1 -0.2(8) . . . . ?
H1 C1 N3 C2 -178.1(3) . . . . ?
N2 C1 N3 C2 1.3(9) . . . . ?
C3 C2 N3 C1 1.3(7) . . . . ?
N5 C2 N3 C1 -179.2(5) . . . . ?
H5 C5 N4 C3 179.3(3) . . . . ?
N5 C5 N4 C3 -0.7(6) . . . . ?
C2 C3 N4 C5 0.6(6) . . . . ?
C4 C3 N4 C5 -176.6(5) . . . . ?
H5 C5 N5 C2 -179.4(2) . . . . ?
N4 C5 N5 C2 0.5(6) . . . . ?
H5 C5 N5 C6 -11.3(7) . . . . ?
N4 C5 N5 C6 168.7(5) . . . . ?
N3 C2 N5 C5 -179.7(5) . . . . ?
C3 C2 N5 C5 -0.1(5) . . . . ?
N3 C2 N5 C6 11.4(8) . . . . ?
C3 C2 N5 C6 -169.0(5) . . . . ?
H6 C6 N5 C5 158.9(5) . . . . ?
O1 C6 N5 C5 -78.0(6) . . . . ?
C7 C6 N5 C5 27.1(8) . . . . ?
H6 C6 N5 C2 -35.1(5) . . . . ?
O1 C6 N5 C2 87.9(5) . . . . ?
C7 C6 N5 C2 -166.9(4) . . . . ?
H6 C6 O1 C8 -103.7(3) . . . . ?
N5 C6 O1 C8 133.0(4) . . . . ?
C7 C6 O1 C8 9.1(4) . . . . ?
H8 C8 O1 C6 102.8(2) . . . . ?
C9 C8 O1 C6 -132.0(4) . . . . ?
C7 C8 O1 C6 -9.0(4) . . . . ?
H9A C9 O2 H2 -48(6) . . . . ?
H9B C9 O2 H2 -165(6) . . . . ?
C8 C9 O2 H2 74(6) . . . . ?

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
O3 D3B O1 0.819(10) 2.26(3) 3.034(6) 157(6) 1_455
O3 D3A N3 0.821(10) 2.008(14) 2.822(6) 171(7) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.075
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'CH2Cl2, CH3OH'
_chemical_compound_source        synthesis
