# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_6b
#===================================================================
#===================================================================
# 5. CHEMICAL DATA
#===================================================================

_chemical_name_systematic        
;
 
;
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H23 N5 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C13 H23 N5 O'
_chemical_formula_weight         265.36

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

#===================================================================
# 6. CRYSTAL DATA
#===================================================================

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.0724(2)
_cell_length_b                   11.4713(3)
_cell_length_c                   13.9904(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.6508(13)
_cell_angle_gamma                90
_cell_volume                     1430.93(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9399
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.46

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    none
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_T_max  0.7452

_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_special_details           
;
Diffractometer operator             E. Herdtweck
scanspeed                           30 s per frame
dx                                  40
4743 frames measured in 11 data sets
phi-scan with delta_phi         = 0.50
omega-scans with delta_omega    = 0.50
;

#===================================================================
# 7. EXPERIMENTAL DATA
#===================================================================

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16 # 8 for binned mode

_diffrn_standards_decay_%        0
# number of measured reflections (redundant set)
_diffrn_reflns_number            47234
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0066
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.46
_reflns_number_total             2636
_reflns_number_gt                2468

# number of observed reflections (> n sig(I))
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'

#===================================================================
# 8. REFINEMENT DATA
#===================================================================

_refine_special_details          
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating  R_factor_obs 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      sigma
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.5542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.031

#===================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
#===================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.29706(8) 0.01160(7) -0.02628(5) 1.000 0.0226(2) . .
N1 N Uani 0.62665(9) 0.05447(7) 0.37792(6) 1.000 0.0158(2) . .
N2 N Uani 0.69006(10) -0.04206(7) 0.42398(6) 1.000 0.0205(3) . .
N3 N Uani 0.64664(10) -0.12965(8) 0.36750(6) 1.000 0.0223(3) . .
N4 N Uani 0.55549(10) -0.09379(8) 0.28452(6) 1.000 0.0195(3) . .
N5 N Uani 0.45567(10) 0.04616(7) 0.11840(6) 1.000 0.0170(2) . .
C1 C Uani 0.54482(11) 0.02049(9) 0.29194(7) 1.000 0.0153(3) . .
C2 C Uani 0.45454(11) 0.09525(9) 0.21427(7) 1.000 0.0158(3) . .
C3 C Uani 0.32159(11) 0.04586(8) 0.05858(7) 1.000 0.0174(3) . .
C4 C Uani 0.20649(12) 0.09593(9) 0.11270(7) 1.000 0.0190(3) . .
C5 C Uani 0.28513(12) 0.09639(10) 0.21884(8) 1.000 0.0199(3) . .
C6 C Uani 0.65870(12) 0.17195(9) 0.42475(7) 1.000 0.0178(3) . .
C7 C Uani 0.50889(13) 0.23388(9) 0.42353(8) 1.000 0.0207(3) . .
C8 C Uani 0.73174(14) 0.15264(10) 0.53131(8) 1.000 0.0249(3) . .
C9 C Uani 0.75613(12) 0.24666(9) 0.36827(7) 1.000 0.0178(3) . .
C10 C Uani 0.89964(11) 0.20129(9) 0.33523(7) 1.000 0.0189(3) . .
C11 C Uani 0.86471(13) 0.11255(10) 0.25230(8) 1.000 0.0238(3) . .
C12 C Uani 0.97101(13) 0.30886(10) 0.29664(9) 1.000 0.0264(4) . .
C13 C Uani 1.01386(13) 0.14773(11) 0.41746(9) 1.000 0.0289(4) . .
H5 H Uiso 0.5367(16) 0.0283(12) 0.0978(10) 1.000 0.027(3) . .
H21 H Uiso 0.4940(12) 0.1736(10) 0.2187(8) 1.000 0.012(3) . .
H41 H Uiso 0.1150(15) 0.0500(11) 0.0995(9) 1.000 0.023(3) . .
H42 H Uiso 0.1846(14) 0.1741(12) 0.0883(9) 1.000 0.027(3) . .
H51 H Uiso 0.2619(14) 0.0257(12) 0.2507(9) 1.000 0.024(3) . .
H52 H Uiso 0.2619(14) 0.1643(12) 0.2548(9) 1.000 0.025(3) . .
H71 H Uiso 0.4624(14) 0.2574(11) 0.3589(10) 1.000 0.022(3) . .
H72 H Uiso 0.5298(14) 0.3047(12) 0.4642(10) 1.000 0.027(3) . .
H73 H Uiso 0.4400(15) 0.1846(12) 0.4527(10) 1.000 0.029(3) . .
H81 H Uiso 0.6600(15) 0.1119(12) 0.5654(10) 1.000 0.031(3) . .
H82 H Uiso 0.7539(16) 0.2321(13) 0.5600(10) 1.000 0.037(4) . .
H83 H Uiso 0.8263(15) 0.1073(12) 0.5399(9) 1.000 0.029(3) . .
H91 H Uiso 0.7854(14) 0.3139(11) 0.4106(9) 1.000 0.022(3) . .
H92 H Uiso 0.6896(13) 0.2781(10) 0.3095(9) 1.000 0.017(3) . .
H111 H Uiso 0.9563(16) 0.0996(12) 0.2245(10) 1.000 0.034(4) . .
H112 H Uiso 0.7823(16) 0.1418(12) 0.2000(10) 1.000 0.032(3) . .
H113 H Uiso 0.8364(15) 0.0359(12) 0.2760(10) 1.000 0.030(3) . .
H121 H Uiso 1.0045(16) 0.3640(13) 0.3495(11) 1.000 0.035(4) . .
H122 H Uiso 0.8986(16) 0.3486(12) 0.2455(10) 1.000 0.032(4) . .
H123 H Uiso 1.0597(16) 0.2863(12) 0.2676(10) 1.000 0.032(3) . .
H131 H Uiso 0.9766(15) 0.0718(13) 0.4398(10) 1.000 0.034(4) . .
H132 H Uiso 1.0336(16) 0.2012(13) 0.4748(11) 1.000 0.037(4) . .
H133 H Uiso 1.1109(17) 0.1336(13) 0.3951(10) 1.000 0.039(4) . .


#==================================================================
# 10. MOLECULAR GEOMETRY
#===================================================================

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2312(12) . . yes
N1 N2 1.3547(12) . . yes
N1 C1 1.3491(13) . . yes
N1 C6 1.5032(13) . . yes
N2 N3 1.2939(12) . . yes
N3 N4 1.3587(12) . . yes
N4 C1 1.3200(14) . . yes
N5 C2 1.4565(13) . . yes
N5 C3 1.3431(13) . . yes
N5 H5 0.862(15) . . no
C1 C2 1.5027(14) . . no
C2 C5 1.5501(15) . . no
C3 C4 1.5119(15) . . no
C4 C5 1.5240(15) . . no
C6 C8 1.5315(15) . . no
C6 C9 1.5487(15) . . no
C6 C7 1.5309(16) . . no
C9 C10 1.5499(15) . . no
C10 C12 1.5371(16) . . no
C10 C13 1.5278(16) . . no
C10 C11 1.5320(15) . . no
C2 H21 0.965(11) . . no
C4 H41 0.972(13) . . no
C4 H42 0.967(14) . . no
C5 H51 0.967(13) . . no
C5 H52 0.971(13) . . no
C7 H71 0.963(14) . . no
C7 H72 0.990(14) . . no
C7 H73 0.985(14) . . no
C8 H81 0.992(14) . . no
C8 H82 1.001(15) . . no
C8 H83 0.991(14) . . no
C9 H91 0.979(13) . . no
C9 H92 0.994(12) . . no
C11 H111 0.992(15) . . no
C11 H112 1.002(14) . . no
C11 H113 0.990(14) . . no
C12 H121 0.978(15) . . no
C12 H122 0.989(14) . . no
C12 H123 1.000(15) . . no
C13 H131 1.005(15) . . no
C13 H132 0.999(15) . . no
C13 H133 1.001(15) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 107.66(8) . . . yes
N2 N1 C6 119.64(8) . . . yes
C1 N1 C6 132.68(8) . . . yes
N1 N2 N3 106.84(8) . . . yes
N2 N3 N4 110.81(8) . . . yes
N3 N4 C1 105.99(8) . . . yes
C2 N5 C3 114.53(8) . . . yes
C3 N5 H5 121.4(9) . . . no
C2 N5 H5 123.4(9) . . . no
N1 C1 C2 128.06(9) . . . yes
N1 C1 N4 108.71(9) . . . yes
N4 C1 C2 123.23(9) . . . yes
N5 C2 C5 102.54(8) . . . yes
C1 C2 C5 112.77(8) . . . no
N5 C2 C1 110.46(8) . . . yes
N5 C3 C4 108.47(8) . . . yes
O1 C3 N5 125.67(9) . . . yes
O1 C3 C4 125.85(9) . . . yes
C3 C4 C5 104.30(9) . . . no
C2 C5 C4 104.42(8) . . . no
N1 C6 C8 107.98(8) . . . yes
N1 C6 C9 110.88(8) . . . yes
C7 C6 C9 109.07(8) . . . no
C8 C6 C9 113.06(9) . . . no
C7 C6 C8 107.55(9) . . . no
N1 C6 C7 108.14(8) . . . yes
C6 C9 C10 123.81(9) . . . no
C9 C10 C12 105.47(8) . . . no
C9 C10 C13 113.62(8) . . . no
C11 C10 C13 108.64(9) . . . no
C12 C10 C13 108.43(9) . . . no
C11 C10 C12 108.00(9) . . . no
C9 C10 C11 112.42(9) . . . no
N5 C2 H21 110.7(7) . . . no
C1 C2 H21 109.8(7) . . . no
C5 C2 H21 110.4(7) . . . no
C3 C4 H41 110.1(8) . . . no
C3 C4 H42 106.9(8) . . . no
C5 C4 H41 114.6(7) . . . no
C5 C4 H42 111.7(8) . . . no
H41 C4 H42 108.9(11) . . . no
C2 C5 H51 108.3(8) . . . no
C2 C5 H52 109.9(8) . . . no
C4 C5 H51 110.1(8) . . . no
C4 C5 H52 113.6(7) . . . no
H51 C5 H52 110.3(11) . . . no
C6 C7 H71 112.0(8) . . . no
C6 C7 H72 107.4(8) . . . no
C6 C7 H73 111.0(8) . . . no
H71 C7 H72 108.3(11) . . . no
H71 C7 H73 110.4(11) . . . no
H72 C7 H73 107.6(11) . . . no
C6 C8 H81 109.4(8) . . . no
C6 C8 H82 106.1(8) . . . no
C6 C8 H83 113.8(7) . . . no
H81 C8 H82 109.7(11) . . . no
H81 C8 H83 108.9(11) . . . no
H82 C8 H83 108.9(12) . . . no
C6 C9 H91 104.1(7) . . . no
C6 C9 H92 107.8(7) . . . no
C10 C9 H91 107.2(8) . . . no
C10 C9 H92 106.9(7) . . . no
H91 C9 H92 105.7(10) . . . no
C10 C11 H111 109.0(8) . . . no
C10 C11 H112 110.6(8) . . . no
C10 C11 H113 111.5(8) . . . no
H111 C11 H112 109.3(12) . . . no
H111 C11 H113 106.6(11) . . . no
H112 C11 H113 109.7(11) . . . no
C10 C12 H121 110.2(9) . . . no
C10 C12 H122 111.0(8) . . . no
C10 C12 H123 111.0(8) . . . no
H121 C12 H122 108.7(12) . . . no
H121 C12 H123 108.3(12) . . . no
H122 C12 H123 107.6(12) . . . no
C10 C13 H131 111.3(8) . . . no
C10 C13 H132 110.7(9) . . . no
C10 C13 H133 110.1(8) . . . no
H131 C13 H132 107.6(12) . . . no
H131 C13 H133 108.8(12) . . . no
H132 C13 H133 108.2(12) . . . no

# End of Crystallographic Information File

_database_code_depnum_ccdc_archive 'CCDC 961190'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_6e
#===================================================================
#===================================================================
# 5. CHEMICAL DATA
#===================================================================

_chemical_name_systematic        
;
 
;
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H17 N5 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C11 H17 N5 O'
_chemical_formula_weight         235.30

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

#===================================================================
# 6. CRYSTAL DATA
#===================================================================

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.5462(2)
_cell_length_b                   9.2570(2)
_cell_length_c                   10.5529(3)
_cell_angle_alpha                65.9412(10)
_cell_angle_beta                 81.5752(11)
_cell_angle_gamma                89.9391(11)
_cell_volume                     576.41(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      25.38

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    none
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_T_max  0.7452

_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_special_details           
;
Diffractometer operator             E. Herdtweck
scanspeed                           30 s per frame
dx                                  35
5785 frames measured in 14 data sets
phi-scan with delta_phi         = 0.50
omega-scans with delta_omega    = 0.50
;

#===================================================================
# 7. EXPERIMENTAL DATA
#===================================================================

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16 # 8 for binned mode

_diffrn_standards_decay_%        0
# number of measured reflections (redundant set)
_diffrn_reflns_number            19536
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2111
_reflns_number_gt                2033

# number of observed reflections (> n sig(I))
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'

#===================================================================
# 8. REFINEMENT DATA
#===================================================================

_refine_special_details          
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating  R_factor_obs 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      sigma
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037

#===================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
#===================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani -0.19947(11) -0.12238(9) 0.47110(8) 1.000 0.0187(2) . .
N1 N Uani 0.45115(13) 0.14746(10) 0.12345(9) 1.000 0.0129(2) . .
N2 N Uani 0.43085(13) 0.24291(10) -0.01008(9) 1.000 0.0152(2) . .
N3 N Uani 0.30930(13) 0.16472(11) -0.05026(9) 1.000 0.0162(2) . .
N4 N Uani 0.24877(13) 0.01897(10) 0.05423(9) 1.000 0.0153(2) . .
N5 N Uani 0.15168(13) -0.08949(10) 0.39941(9) 1.000 0.0144(3) . .
C1 C Uani 0.33900(15) 0.01069(12) 0.16085(11) 1.000 0.0129(3) . .
C2 C Uani 0.30818(16) -0.12549(12) 0.30383(11) 1.000 0.0143(3) . .
C3 C Uani -0.03940(16) -0.15067(12) 0.40970(10) 1.000 0.0149(3) . .
C4 C Uani -0.02484(17) -0.25836(13) 0.33341(12) 1.000 0.0181(3) . .
C5 C Uani 0.20772(17) -0.27603(12) 0.30321(12) 1.000 0.0173(3) . .
C6 C Uani 0.58675(16) 0.19938(12) 0.19901(11) 1.000 0.0138(3) . .
C7 C Uani 0.50258(16) 0.34137(12) 0.22390(11) 1.000 0.0150(3) . .
C8 C Uani 0.64586(17) 0.39371(13) 0.30170(12) 1.000 0.0183(3) . .
C9 C Uani 0.86832(17) 0.42935(13) 0.22386(12) 1.000 0.0190(3) . .
C10 C Uani 0.94855(17) 0.28975(13) 0.19427(12) 1.000 0.0187(3) . .
C11 C Uani 0.80598(16) 0.23728(14) 0.11675(12) 1.000 0.0184(3) . .
H5 H Uiso 0.175(2) -0.0209(18) 0.4333(15) 1.000 0.029(4) . .
H21 H Uiso 0.4397(19) -0.1443(14) 0.3401(13) 1.000 0.014(3) . .
H41 H Uiso -0.083(2) -0.2067(16) 0.2483(15) 1.000 0.022(3) . .
H42 H Uiso -0.103(2) -0.3564(16) 0.3920(14) 1.000 0.020(3) . .
H51 H Uiso 0.2521(19) -0.2843(15) 0.2155(14) 1.000 0.018(3) . .
H52 H Uiso 0.2494(19) -0.3689(15) 0.3791(14) 1.000 0.017(3) . .
H61 H Uiso 0.5840(18) 0.1087(14) 0.2886(13) 1.000 0.012(3) . .
H71 H Uiso 0.362(2) 0.3127(15) 0.2783(14) 1.000 0.019(3) . .
H72 H Uiso 0.4964(19) 0.4298(15) 0.1329(14) 1.000 0.015(3) . .
H81 H Uiso 0.593(2) 0.4879(17) 0.3130(15) 1.000 0.027(4) . .
H82 H Uiso 0.642(2) 0.3089(16) 0.3958(15) 1.000 0.022(3) . .
H91 H Uiso 0.873(2) 0.5234(17) 0.1353(15) 1.000 0.022(3) . .
H92 H Uiso 0.959(2) 0.4559(16) 0.2780(14) 1.000 0.025(3) . .
H101 H Uiso 0.959(2) 0.1983(16) 0.2837(15) 1.000 0.022(3) . .
H102 H Uiso 1.088(2) 0.3192(15) 0.1370(14) 1.000 0.021(3) . .
H111 H Uiso 0.802(2) 0.3230(16) 0.0244(15) 1.000 0.022(3) . .
H112 H Uiso 0.854(2) 0.1449(17) 0.1003(15) 1.000 0.026(3) . .


#==================================================================
# 10. MOLECULAR GEOMETRY
#===================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2350(13) . . yes
N1 N2 1.3504(12) . . yes
N1 C1 1.3444(15) . . yes
N1 C6 1.4750(14) . . yes
N2 N3 1.2989(14) . . yes
N3 N4 1.3614(13) . . yes
N4 C1 1.3210(14) . . yes
N5 C2 1.4658(14) . . yes
N5 C3 1.3449(14) . . yes
N5 H5 0.869(17) . . no
C1 C2 1.5057(15) . . no
C2 C5 1.5444(17) . . no
C3 C4 1.5109(17) . . no
C4 C5 1.5316(16) . . no
C6 C11 1.5245(15) . . no
C6 C7 1.5290(17) . . no
C7 C8 1.5295(16) . . no
C8 C9 1.5277(16) . . no
C9 C10 1.5241(18) . . no
C10 C11 1.5247(17) . . no
C2 H21 0.980(13) . . no
C4 H41 0.964(14) . . no
C4 H42 0.958(15) . . no
C5 H51 0.962(14) . . no
C5 H52 0.978(14) . . no
C6 H61 0.973(13) . . no
C7 H71 0.984(13) . . no
C7 H72 0.982(14) . . no
C8 H81 0.983(17) . . no
C8 H82 0.980(15) . . no
C9 H91 0.980(15) . . no
C9 H92 0.976(14) . . no
C10 H101 0.990(15) . . no
C10 H102 0.989(13) . . no
C11 H111 0.978(15) . . no
C11 H112 0.982(17) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 108.11(9) . . . yes
N2 N1 C6 120.26(9) . . . yes
C1 N1 C6 131.57(9) . . . yes
N1 N2 N3 106.52(9) . . . yes
N2 N3 N4 110.86(8) . . . yes
N3 N4 C1 105.68(9) . . . yes
C2 N5 C3 113.41(9) . . . yes
C2 N5 H5 123.0(9) . . . no
C3 N5 H5 122.6(9) . . . no
N1 C1 N4 108.83(9) . . . yes
N1 C1 C2 125.85(9) . . . yes
N4 C1 C2 125.19(10) . . . yes
N5 C2 C1 109.59(9) . . . yes
C1 C2 C5 112.28(9) . . . no
N5 C2 C5 101.88(9) . . . yes
O1 C3 C4 126.05(10) . . . yes
N5 C3 C4 108.66(9) . . . yes
O1 C3 N5 125.29(11) . . . yes
C3 C4 C5 104.06(9) . . . no
C2 C5 C4 103.76(9) . . . no
N1 C6 C7 110.82(9) . . . yes
C7 C6 C11 111.60(10) . . . no
N1 C6 C11 109.49(9) . . . yes
C6 C7 C8 109.96(9) . . . no
C7 C8 C9 111.67(9) . . . no
C8 C9 C10 111.52(10) . . . no
C9 C10 C11 111.89(10) . . . no
C6 C11 C10 110.11(10) . . . no
N5 C2 H21 110.5(8) . . . no
C1 C2 H21 109.7(7) . . . no
C5 C2 H21 112.6(8) . . . no
C3 C4 H41 108.0(10) . . . no
C3 C4 H42 109.1(9) . . . no
C5 C4 H41 112.1(8) . . . no
C5 C4 H42 113.7(9) . . . no
H41 C4 H42 109.5(12) . . . no
C2 C5 H51 111.2(9) . . . no
C2 C5 H52 108.7(8) . . . no
C4 C5 H51 114.1(8) . . . no
C4 C5 H52 110.5(8) . . . no
H51 C5 H52 108.6(12) . . . no
N1 C6 H61 104.8(8) . . . no
C7 C6 H61 109.8(8) . . . no
C11 C6 H61 110.1(7) . . . no
C6 C7 H71 109.6(9) . . . no
C6 C7 H72 109.2(9) . . . no
C8 C7 H71 110.6(8) . . . no
C8 C7 H72 108.7(8) . . . no
H71 C7 H72 108.8(11) . . . no
C7 C8 H81 108.9(8) . . . no
C7 C8 H82 108.6(9) . . . no
C9 C8 H81 110.3(8) . . . no
C9 C8 H82 109.6(8) . . . no
H81 C8 H82 107.7(12) . . . no
C8 C9 H91 108.7(8) . . . no
C8 C9 H92 110.5(8) . . . no
C10 C9 H91 109.9(9) . . . no
C10 C9 H92 109.7(9) . . . no
H91 C9 H92 106.4(12) . . . no
C9 C10 H101 110.0(9) . . . no
C9 C10 H102 109.8(9) . . . no
C11 C10 H101 108.0(9) . . . no
C11 C10 H102 108.9(8) . . . no
H101 C10 H102 108.2(11) . . . no
C6 C11 H111 108.2(8) . . . no
C6 C11 H112 109.6(8) . . . no
C10 C11 H111 109.6(9) . . . no
C10 C11 H112 112.4(8) . . . no
H111 C11 H112 106.8(12) . . . no

# End of Crystallographic Information File

_database_code_depnum_ccdc_archive 'CCDC 961191'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_6f
#===================================================================
#===================================================================
# 5. CHEMICAL DATA
#===================================================================

_chemical_name_systematic        
;
 
;
_chemical_name_common            ?
_chemical_formula_moiety         '2(C10 H17 N5 O), H2 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C20 H36 N10 O3'
_chemical_formula_weight         464.59

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

#===================================================================
# 6. CRYSTAL DATA
#===================================================================

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   26.6036(6)
_cell_length_b                   6.3028(1)
_cell_length_c                   15.4666(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.7809(9)
_cell_angle_gamma                90
_cell_volume                     2440.37(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      25.55

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_T_max  0.7452

_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_special_details           
;
Diffractometer operator             E. Herdtweck
scanspeed                           30 s per frame
dx                                  40
3306 frames measured in 7 data sets
phi-scan with delta_phi         = 0.50
omega-scans with delta_omega    = 0.50
;

#===================================================================
# 7. EXPERIMENTAL DATA
#===================================================================

_diffrn_ambient_temperature      123(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16 # 8 for binned mode

_diffrn_standards_decay_%        0
# number of measured reflections (redundant set)
_diffrn_reflns_number            33632
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.55
_reflns_number_total             2264
_reflns_number_gt                2037

# number of observed reflections (> n sig(I))
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'

#===================================================================
# 8. REFINEMENT DATA
#===================================================================

_refine_special_details          
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating  R_factor_obs 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      sigma
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+1.7210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2264
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.55
_diffrn_measured_fraction_theta_full 0.987

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036

#===================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
#===================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.00828(4) 0.81833(18) -0.08356(6) 1.000 0.0386(3) . .
N1 N Uani 0.17891(4) 0.95871(15) 0.25089(6) 1.000 0.0196(3) . .
N2 N Uani 0.21944(4) 1.06365(17) 0.23555(7) 1.000 0.0261(3) . .
N3 N Uani 0.21104(4) 1.05164(17) 0.14812(7) 1.000 0.0282(3) . .
N4 N Uani 0.16573(4) 0.94121(17) 0.10485(7) 1.000 0.0256(3) . .
N5 N Uani 0.05565(4) 0.8232(2) 0.06695(7) 1.000 0.0291(3) . .
C1 C Uani 0.14634(4) 0.88457(19) 0.16946(7) 1.000 0.0205(3) . .
C2 C Uani 0.09697(5) 0.7500(2) 0.15116(8) 1.000 0.0255(4) . .
C3 C Uani 0.04301(5) 0.7356(2) -0.01630(8) 1.000 0.0284(4) . .
C4 C Uani 0.06874(5) 0.5310(2) -0.02722(8) 1.000 0.0280(4) . .
C5 C Uani 0.11812(5) 0.4708(2) 0.05327(9) 1.000 0.0276(4) . .
C6 C Uani 0.10944(5) 0.5159(2) 0.14354(9) 1.000 0.0296(4) . .
C7 C Uani 0.17524(5) 0.95308(19) 0.34600(8) 1.000 0.0219(3) . .
C8 C Uani 0.22766(6) 1.0363(3) 0.41303(9) 1.000 0.0345(5) . .
C9 C Uani 0.16774(5) 0.7248(2) 0.37097(9) 1.000 0.0261(4) . .
C10 C Uani 0.12880(7) 1.0931(3) 0.34660(10) 1.000 0.0394(5) . .
O2 O Uani 0.00000 0.3928(3) 0.25000 1.000 0.0485(5) . .
H5 H Uiso 0.0376(7) 0.942(3) 0.0693(11) 1.000 0.036(4) . .
H21 H Uiso 0.0830(5) 0.768(2) 0.2007(10) 1.000 0.026(3) . .
H41 H Uiso 0.0419(7) 0.421(3) -0.0343(11) 1.000 0.039(4) . .
H42 H Uiso 0.0747(6) 0.537(2) -0.0857(10) 1.000 0.030(4) . .
H51 H Uiso 0.1490(6) 0.553(2) 0.0495(9) 1.000 0.025(3) . .
H52 H Uiso 0.1260(6) 0.321(3) 0.0497(10) 1.000 0.032(4) . .
H61 H Uiso 0.0797(6) 0.432(2) 0.1477(10) 1.000 0.035(4) . .
H62 H Uiso 0.1415(6) 0.480(2) 0.1958(11) 1.000 0.031(4) . .
H81 H Uiso 0.2335(7) 1.182(3) 0.3984(11) 1.000 0.047(5) . .
H82 H Uiso 0.2243(6) 1.034(2) 0.4753(11) 1.000 0.039(4) . .
H83 H Uiso 0.2588(7) 0.945(3) 0.4102(12) 1.000 0.047(5) . .
H91 H Uiso 0.1954(6) 0.635(3) 0.3636(10) 1.000 0.035(4) . .
H92 H Uiso 0.1702(6) 0.726(2) 0.4355(11) 1.000 0.034(4) . .
H93 H Uiso 0.1318(6) 0.665(2) 0.3338(10) 1.000 0.037(4) . .
H101 H Uiso 0.0932(8) 1.043(3) 0.3028(13) 1.000 0.054(5) . .
H102 H Uiso 0.1277(6) 1.091(3) 0.4101(12) 1.000 0.043(4) . .
H103 H Uiso 0.1345(8) 1.242(4) 0.3308(13) 1.000 0.066(6) . .
H2 H Uiso 0.0033(8) 0.313(3) 0.2971(13) 1.000 0.065(6) . .


#==================================================================
# 10. MOLECULAR GEOMETRY
#===================================================================

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2479(16) . . yes
O2 H2 0.865(19) . 2_555 no
O2 H2 0.865(19) . . no
N1 C1 1.3479(14) . . yes
N1 N2 1.3526(15) . . yes
N1 C7 1.5073(15) . . yes
N2 N3 1.2960(14) . . yes
N3 N4 1.3562(15) . . yes
N4 C1 1.3195(15) . . yes
N5 C3 1.3352(16) . . yes
N5 C2 1.4658(16) . . yes
N5 H5 0.897(19) . . no
C1 C2 1.5076(18) . . no
C2 C6 1.5256(18) . . no
C3 C4 1.4961(18) . . no
C4 C5 1.5207(18) . . no
C5 C6 1.5171(19) . . no
C7 C9 1.5203(18) . . no
C7 C10 1.521(2) . . no
C7 C8 1.522(2) . . no
C2 H21 0.965(14) . . no
C4 H42 0.970(15) . . no
C4 H41 0.975(19) . . no
C5 H52 0.973(19) . . no
C5 H51 0.990(16) . . no
C6 H61 0.972(16) . . no
C6 H62 0.983(16) . . no
C8 H82 0.997(16) . . no
C8 H81 0.971(19) . . no
C8 H83 1.022(19) . . no
C9 H92 0.978(16) . . no
C9 H93 1.007(16) . . no
C9 H91 0.965(18) . . no
C10 H103 0.99(2) . . no
C10 H101 1.01(2) . . no
C10 H102 0.993(17) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2 O2 H2 108.9(18) . . 2_555 no
N2 N1 C7 120.10(9) . . . yes
C1 N1 C7 132.09(11) . . . yes
N2 N1 C1 107.71(9) . . . yes
N1 N2 N3 106.75(10) . . . yes
N2 N3 N4 110.82(10) . . . yes
N3 N4 C1 105.97(10) . . . yes
C2 N5 C3 126.52(12) . . . yes
C3 N5 H5 114.9(10) . . . no
C2 N5 H5 118.5(10) . . . no
N4 C1 C2 123.30(10) . . . yes
N1 C1 N4 108.75(10) . . . yes
N1 C1 C2 127.89(10) . . . yes
C1 C2 C6 111.11(11) . . . no
N5 C2 C6 110.68(10) . . . yes
N5 C2 C1 109.48(10) . . . yes
O1 C3 N5 120.33(12) . . . yes
O1 C3 C4 120.27(11) . . . yes
N5 C3 C4 119.33(11) . . . yes
C3 C4 C5 115.10(10) . . . no
C4 C5 C6 110.38(11) . . . no
C2 C6 C5 110.92(10) . . . no
N1 C7 C10 108.26(10) . . . yes
N1 C7 C9 109.12(10) . . . yes
C9 C7 C10 111.77(12) . . . no
C8 C7 C9 108.78(11) . . . no
C8 C7 C10 110.78(12) . . . no
N1 C7 C8 108.04(11) . . . yes
N5 C2 H21 107.1(9) . . . no
C1 C2 H21 109.3(8) . . . no
C6 C2 H21 109.1(8) . . . no
C3 C4 H41 106.3(12) . . . no
C3 C4 H42 107.3(8) . . . no
C5 C4 H42 113.9(10) . . . no
H41 C4 H42 105.5(13) . . . no
C5 C4 H41 108.2(10) . . . no
C4 C5 H52 109.8(9) . . . no
C6 C5 H51 110.1(8) . . . no
C4 C5 H51 109.0(8) . . . no
H51 C5 H52 107.8(13) . . . no
C6 C5 H52 109.7(9) . . . no
C2 C6 H61 108.5(8) . . . no
C5 C6 H61 109.9(9) . . . no
C5 C6 H62 110.7(9) . . . no
H61 C6 H62 108.7(12) . . . no
C2 C6 H62 108.1(8) . . . no
C7 C8 H82 107.0(9) . . . no
C7 C8 H83 110.3(10) . . . no
C7 C8 H81 110.4(10) . . . no
H81 C8 H83 109.1(16) . . . no
H82 C8 H83 111.9(13) . . . no
H81 C8 H82 108.2(12) . . . no
C7 C9 H91 110.7(11) . . . no
C7 C9 H92 106.4(8) . . . no
H91 C9 H92 109.6(13) . . . no
H91 C9 H93 109.1(13) . . . no
C7 C9 H93 113.0(8) . . . no
H92 C9 H93 108.0(13) . . . no
C7 C10 H102 107.1(10) . . . no
C7 C10 H103 110.8(13) . . . no
C7 C10 H101 113.2(12) . . . no
H101 C10 H103 108.5(16) . . . no
H102 C10 H103 108.3(16) . . . no
H101 C10 H102 108.9(16) . . . no

# End of Crystallographic Information File

_database_code_depnum_ccdc_archive 'CCDC 961188'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_6j
#===================================================================
#===================================================================
# 5. CHEMICAL DATA
#===================================================================

_chemical_name_systematic        
;
 
;
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H19 N5 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H19 N5 O'
_chemical_formula_weight         249.32

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

#===================================================================
# 6. CRYSTAL DATA
#===================================================================

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

_cell_length_a                   9.9162(3)
_cell_length_b                   11.9389(3)
_cell_length_c                   21.5252(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.34(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.40

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7060
_exptl_absorpt_correction_T_max  0.7452

_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_special_details           
;
Diffractometer operator             E. Herdtweck
scanspeed                           20 s per frame
dx                                  60
3381 frames measured in 6 data sets
phi-scan with delta_phi         = 0.50
omega-scans with delta_omega    = 0.50
;

#===================================================================
# 7. EXPERIMENTAL DATA
#===================================================================

_diffrn_ambient_temperature      123(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16 # 8 for binned mode

_diffrn_standards_decay_%        0
# number of measured reflections (redundant set)
_diffrn_reflns_number            31566
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2338
_reflns_number_gt                2085

# number of observed reflections (> n sig(I))
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'

#===================================================================
# 8. REFINEMENT DATA
#===================================================================

_refine_special_details          
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating  R_factor_obs 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      sigma
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+1.2420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2338
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.042

#===================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
#===================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.46598(10) -0.07421(8) -0.07050(5) 1.000 0.0244(3) . .
N1 N Uani 0.24950(11) 0.27811(9) 0.06371(5) 1.000 0.0183(3) . .
N2 N Uani 0.31435(12) 0.37495(10) 0.07704(6) 1.000 0.0236(4) . .
N3 N Uani 0.37981(12) 0.40287(10) 0.02732(6) 1.000 0.0233(4) . .
N4 N Uani 0.36039(12) 0.32654(10) -0.01869(6) 1.000 0.0216(4) . .
N5 N Uani 0.34533(12) 0.06695(9) -0.02940(6) 1.000 0.0184(3) . .
C1 C Uani 0.27901(13) 0.24969(11) 0.00507(6) 1.000 0.0169(4) . .
C2 C Uani 0.23165(14) 0.14571(11) -0.02761(6) 1.000 0.0173(4) . .
C3 C Uani 0.36970(13) -0.00790(11) -0.07419(7) 1.000 0.0185(4) . .
C4 C Uani 0.28234(14) -0.00683(12) -0.13146(7) 1.000 0.0212(4) . .
C5 C Uani 0.15181(15) 0.05977(12) -0.12534(7) 1.000 0.0222(4) . .
C6 C Uani 0.18069(15) 0.17049(11) -0.09283(7) 1.000 0.0205(4) . .
C7 C Uani 0.17259(14) 0.21870(12) 0.11227(7) 1.000 0.0211(4) . .
C8 C Uani 0.26846(17) 0.15827(14) 0.15589(8) 1.000 0.0295(5) . .
C9 C Uani 0.18955(19) 0.09689(15) 0.20643(8) 1.000 0.0343(5) . .
C10 C Uani 0.09689(17) 0.17624(15) 0.24165(8) 1.000 0.0323(5) . .
C11 C Uani 0.00264(17) 0.23619(17) 0.19692(8) 1.000 0.0362(5) . .
C12 C Uani 0.08116(17) 0.29905(15) 0.14684(8) 1.000 0.0317(5) . .
H5 H Uiso 0.3978(18) 0.0660(13) 0.0022(8) 1.000 0.023(4) . .
H21 H Uiso 0.1596(16) 0.1125(13) -0.0038(7) 1.000 0.017(4) . .
H41 H Uiso 0.2647(16) -0.0852(14) -0.1417(7) 1.000 0.025(4) . .
H42 H Uiso 0.3381(16) 0.0274(13) -0.1648(8) 1.000 0.025(4) . .
H51 H Uiso 0.0859(17) 0.0166(13) -0.1005(7) 1.000 0.025(4) . .
H52 H Uiso 0.1124(16) 0.0727(13) -0.1680(8) 1.000 0.025(4) . .
H61 H Uiso 0.2487(16) 0.2147(13) -0.1163(7) 1.000 0.018(4) . .
H62 H Uiso 0.0982(17) 0.2153(13) -0.0899(7) 1.000 0.025(4) . .
H71 H Uiso 0.1169(17) 0.1629(13) 0.0898(8) 1.000 0.025(4) . .
H81 H Uiso 0.3267(19) 0.2175(16) 0.1751(9) 1.000 0.038(5) . .
H82 H Uiso 0.325(2) 0.1092(16) 0.1325(9) 1.000 0.040(5) . .
H91 H Uiso 0.253(2) 0.0592(16) 0.2355(9) 1.000 0.049(6) . .
H92 H Uiso 0.136(2) 0.0345(18) 0.1874(10) 1.000 0.052(6) . .
H101 H Uiso 0.152(2) 0.2336(17) 0.2651(9) 1.000 0.047(6) . .
H102 H Uiso 0.0456(19) 0.1320(15) 0.2727(8) 1.000 0.037(5) . .
H111 H Uiso -0.061(2) 0.1762(19) 0.1756(11) 1.000 0.065(7) . .
H112 H Uiso -0.054(2) 0.2906(16) 0.2194(9) 1.000 0.050(6) . .
H121 H Uiso 0.1374(17) 0.3572(14) 0.1646(8) 1.000 0.027(4) . .
H122 H Uiso 0.020(2) 0.3331(16) 0.1163(9) 1.000 0.047(5) . .


#==================================================================
# 10. MOLECULAR GEOMETRY
#===================================================================

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2428(16) . . yes
N1 N2 1.3537(16) . . yes
N1 C1 1.3394(17) . . yes
N1 C7 1.4756(18) . . yes
N2 N3 1.2953(18) . . yes
N3 N4 1.3596(18) . . yes
N4 C1 1.3246(18) . . yes
N5 C2 1.4685(18) . . yes
N5 C3 1.3366(19) . . yes
N5 H5 0.857(18) . . no
C1 C2 1.5022(19) . . no
C2 C6 1.521(2) . . no
C3 C4 1.507(2) . . no
C4 C5 1.525(2) . . no
C5 C6 1.523(2) . . no
C7 C12 1.515(2) . . no
C7 C8 1.519(2) . . no
C8 C9 1.527(2) . . no
C9 C10 1.522(3) . . no
C10 C11 1.521(2) . . no
C11 C12 1.527(2) . . no
C2 H21 0.965(16) . . no
C4 H41 0.977(17) . . no
C4 H42 0.994(17) . . no
C5 H51 0.989(16) . . no
C5 H52 1.010(17) . . no
C6 H61 0.994(16) . . no
C6 H62 0.979(17) . . no
C7 H71 0.991(16) . . no
C8 H81 1.002(19) . . no
C8 H82 0.955(19) . . no
C9 H91 1.00(2) . . no
C9 H92 1.00(2) . . no
C10 H101 1.01(2) . . no
C10 H102 0.992(18) . . no
C11 H111 1.06(2) . . no
C11 H112 0.99(2) . . no
C12 H121 0.969(17) . . no
C12 H122 0.98(2) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 108.20(11) . . . yes
N2 N1 C7 120.39(11) . . . yes
C1 N1 C7 131.20(11) . . . yes
N1 N2 N3 106.42(11) . . . yes
N2 N3 N4 111.00(11) . . . yes
N3 N4 C1 105.62(12) . . . yes
C2 N5 C3 125.86(12) . . . yes
C3 N5 H5 117.0(11) . . . no
C2 N5 H5 117.0(11) . . . no
N1 C1 C2 125.62(12) . . . yes
N1 C1 N4 108.75(12) . . . yes
N4 C1 C2 125.60(12) . . . yes
N5 C2 C6 110.82(11) . . . yes
N5 C2 C1 107.55(11) . . . yes
C1 C2 C6 112.05(11) . . . no
N5 C3 C4 118.72(12) . . . yes
O1 C3 C4 119.96(13) . . . yes
O1 C3 N5 121.24(13) . . . yes
C3 C4 C5 114.95(12) . . . no
C4 C5 C6 109.43(12) . . . no
C2 C6 C5 108.53(11) . . . no
N1 C7 C8 110.05(12) . . . yes
C8 C7 C12 111.82(13) . . . no
N1 C7 C12 110.66(12) . . . yes
C7 C8 C9 110.34(14) . . . no
C8 C9 C10 111.43(14) . . . no
C9 C10 C11 110.40(14) . . . no
C10 C11 C12 111.40(14) . . . no
C7 C12 C11 109.92(14) . . . no
N5 C2 H21 108.6(9) . . . no
C1 C2 H21 108.8(9) . . . no
C6 C2 H21 108.9(9) . . . no
C3 C4 H41 106.2(9) . . . no
C3 C4 H42 105.9(10) . . . no
C5 C4 H41 111.5(9) . . . no
C5 C4 H42 108.7(9) . . . no
H41 C4 H42 109.3(13) . . . no
C4 C5 H51 109.6(10) . . . no
C4 C5 H52 109.3(9) . . . no
C6 C5 H51 109.2(9) . . . no
C6 C5 H52 111.0(9) . . . no
H51 C5 H52 108.4(13) . . . no
C2 C6 H61 110.3(9) . . . no
C2 C6 H62 108.9(9) . . . no
C5 C6 H61 110.8(9) . . . no
C5 C6 H62 110.3(9) . . . no
H61 C6 H62 108.0(13) . . . no
N1 C7 H71 105.4(10) . . . no
C8 C7 H71 109.3(10) . . . no
C12 C7 H71 109.4(10) . . . no
C7 C8 H81 106.3(11) . . . no
C7 C8 H82 109.5(12) . . . no
C9 C8 H81 109.9(11) . . . no
C9 C8 H82 112.5(12) . . . no
H81 C8 H82 108.2(16) . . . no
C8 C9 H91 109.9(11) . . . no
C8 C9 H92 109.7(12) . . . no
C10 C9 H91 110.5(11) . . . no
C10 C9 H92 110.3(12) . . . no
H91 C9 H92 104.8(17) . . . no
C9 C10 H101 110.1(11) . . . no
C9 C10 H102 108.3(11) . . . no
C11 C10 H101 109.2(11) . . . no
C11 C10 H102 111.2(11) . . . no
H101 C10 H102 107.5(15) . . . no
C10 C11 H111 108.8(12) . . . no
C10 C11 H112 110.5(11) . . . no
C12 C11 H111 109.3(13) . . . no
C12 C11 H112 108.3(11) . . . no
H111 C11 H112 108.6(16) . . . no
C7 C12 H121 107.6(10) . . . no
C7 C12 H122 107.6(11) . . . no
C11 C12 H121 111.5(10) . . . no
C11 C12 H122 111.2(12) . . . no
H121 C12 H122 108.8(15) . . . no

# End of Crystallographic Information File

_database_code_depnum_ccdc_archive 'CCDC 961189'
