# Electronic Supplementary Material (ESI) for RSC Advances.
# 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_I
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
7'-Amino-1'H-spiro[cycloheptane-1,2'-pyrimido[4,5-d]pyrimidin]-
4'(3'H)-one
;

_chemical_name_common            ?
_chemical_formula_moiety         'C12 H17 N5 O'
_chemical_formula_sum            'C12 H17 N5 O'
_chemical_formula_iupac          'C12 H17 N5 O'
_chemical_formula_weight         247.31
_chemical_melting_point          ?
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz

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


_cell_length_a                   10.798(3)

_cell_length_b                   10.365(3)

_cell_length_c                   11.341(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 110.287(4)

_cell_angle_gamma                90.00

_cell_volume                     1190.5(6)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    4105

_cell_measurement_theta_min      1.965

_cell_measurement_theta_max      30.026

_cell_measurement_temperature    153(2)

_exptl_crystal_description       Block

_exptl_crystal_colour            Colourless

_exptl_crystal_size_max          0.39

_exptl_crystal_size_mid          0.35

_exptl_crystal_size_min          0.26

_exptl_crystal_density_diffrn    1.380

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             528

_exptl_absorpt_coefficient_mu    0.094

_exptl_absorpt_correction_type   none

_exptl_absorpt_process_details   ?

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;


_diffrn_ambient_temperature      153(2)

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_source         'Rotating Anode'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 28.5714

_diffrn_reflns_number            9163

_diffrn_reflns_av_R_equivalents  0.0362

_diffrn_reflns_av_sigmaI/netI    0.0370

_diffrn_reflns_theta_min         2.24

_diffrn_reflns_theta_max         30.03

_diffrn_reflns_theta_full        30.03

_diffrn_measured_fraction_theta_max 0.991

_diffrn_measured_fraction_theta_full 0.991

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       15

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_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 >
σ(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.
;


_reflns_number_total             3450

_reflns_number_gt                3237

_reflns_threshold_expression     I>2sigma(I)

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_R_factor_all          0.0585

_refine_ls_R_factor_gt           0.0544

_refine_ls_wR_factor_gt          0.1263

_refine_ls_wR_factor_ref         0.1291

_refine_ls_goodness_of_fit_ref   1.000

_refine_ls_restrained_S_all      1.000

_refine_ls_number_reflns         3450

_refine_ls_number_parameters     180

_refine_ls_number_restraints     0

_refine_ls_hydrogen_treatment    mixed

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.9600P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.349

_refine_diff_density_min         -0.215

_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'

_refine_ls_extinction_coef       0.0058(19)
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'


_computing_data_collection       'CrystalClear (Rigaku/MSC, 2009)'

_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2009)'

_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2009)'

_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'

_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2009)'

_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group

O O1 0.50270(10) 0.09029(10) 0.36576(9) 0.0190(2) Uani d . 1 1 . .
N N1 0.59501(11) 0.15243(11) 0.56975(10) 0.0168(2) Uani d . 1 1 . .
N N2 0.76803(11) 0.30528(12) 0.63161(10) 0.0180(2) Uani d . 1 1 . .
N N3 0.83812(11) 0.40875(11) 0.48490(10) 0.0175(2) Uani d . 1 1 . .
N N4 0.71560(11) 0.38221(12) 0.26293(10) 0.0190(2) Uani d . 1 1 . .
N N5 0.90263(12) 0.50418(13) 0.33343(12) 0.0217(3) Uani d . 1 1 . .
C C1 0.55839(13) 0.36082(13) 0.65798(12) 0.0190(3) Uani d . 1 1 . .
H H1A 0.6087 0.4380 0.6996 0.023 Uiso calc R 1 1 . .
H H1B 0.5115 0.3832 0.5687 0.023 Uiso calc R 1 1 . .
C C2 0.45569(14) 0.33082(16) 0.71849(13) 0.0235(3) Uani d . 1 1 . .
H H2A 0.4361 0.2372 0.7106 0.028 Uiso calc R 1 1 . .
H H2B 0.3730 0.3774 0.6723 0.028 Uiso calc R 1 1 . .
C C3 0.50040(16) 0.36863(18) 0.85753(14) 0.0302(4) Uani d . 1 1 . .
H H3A 0.5270 0.4605 0.8652 0.036 Uiso calc R 1 1 . .
H H3B 0.4239 0.3608 0.8861 0.036 Uiso calc R 1 1 . .
C C4 0.61375(15) 0.29004(18) 0.94541(13) 0.0281(3) Uani d . 1 1 . .
H H4A 0.5803 0.2028 0.9536 0.034 Uiso calc R 1 1 . .
H H4B 0.6421 0.3307 1.0296 0.034 Uiso calc R 1 1 . .
C C5 0.73471(14) 0.27534(16) 0.90615(12) 0.0235(3) Uani d . 1 1 . .
H H5A 0.8085 0.2403 0.9779 0.028 Uiso calc R 1 1 . .
H H5B 0.7615 0.3617 0.8862 0.028 Uiso calc R 1 1 . .
C C6 0.71173(14) 0.18714(14) 0.79249(12) 0.0198(3) Uani d . 1 1 . .
H H6A 0.6495 0.1182 0.7958 0.024 Uiso calc R 1 1 . .
H H6B 0.7966 0.1452 0.8002 0.024 Uiso calc R 1 1 . .
C C7 0.65745(12) 0.25199(13) 0.66346(11) 0.0150(2) Uani d . 1 1 . .
C C8 0.57409(12) 0.16677(13) 0.44658(12) 0.0153(2) Uani d . 1 1 . .
C C9 0.64680(12) 0.27115(13) 0.41465(12) 0.0158(2) Uani d . 1 1 . .
C C10 0.75182(12) 0.33111(13) 0.51061(12) 0.0154(2) Uani d . 1 1 . .
C C11 0.81680(12) 0.42899(13) 0.36179(12) 0.0167(3) Uani d . 1 1 . .
C C12 0.63510(13) 0.30267(13) 0.29228(12) 0.0177(3) Uani d . 1 1 . .
H H12 0.5650 0.2648 0.2256 0.021 Uiso calc R 1 1 . .
H H2N 0.8326(19) 0.3443(19) 0.6896(18) 0.026(5) Uiso d . 1 1 . .
H H0A 0.9754(19) 0.5290(18) 0.3921(18) 0.023(4) Uiso d . 1 1 . .
H H0B 0.893(2) 0.514(2) 0.257(2) 0.033(5) Uiso d . 1 1 . .
H H1N 0.557(2) 0.087(2) 0.593(2) 0.035(5) Uiso d . 1 1 . .



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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

O1 C8 . 1.2541(16) ?
N1 C8 . 1.3437(17) ?
N1 C7 . 1.4670(16) ?
N1 H1N . 0.88(2) ?
N2 C10 . 1.3488(17) ?
N2 C7 . 1.4698(16) ?
N2 H2N . 0.87(2) ?
N3 C10 . 1.3376(16) ?
N3 C11 . 1.3505(17) ?
N4 C12 . 1.3215(17) ?
N4 C11 . 1.3552(17) ?
N5 C11 . 1.3328(17) ?
N5 H0A . 0.87(2) ?
N5 H0B . 0.84(2) ?
C1 C2 . 1.525(2) ?
C1 C7 . 1.5408(19) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.531(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.520(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.527(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.529(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.5304(18) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C8 C9 . 1.4543(18) ?
C9 C12 . 1.3883(18) ?
C9 C10 . 1.4144(17) ?
C12 H12 . 0.9500 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

C8 N1 C7 . . 123.01(11) ?
C8 N1 H1N . . 118.1(14) ?
C7 N1 H1N . . 118.0(14) ?
C10 N2 C7 . . 119.65(10) ?
C10 N2 H2N . . 117.5(13) ?
C7 N2 H2N . . 119.5(13) ?
C10 N3 C11 . . 115.90(11) ?
C12 N4 C11 . . 115.27(11) ?
C11 N5 H0A . . 120.4(12) ?
C11 N5 H0B . . 118.1(14) ?
H0A N5 H0B . . 120.3(19) ?
C2 C1 C7 . . 115.82(12) ?
C2 C1 H1A . . 108.3 ?
C7 C1 H1A . . 108.3 ?
C2 C1 H1B . . 108.3 ?
C7 C1 H1B . . 108.3 ?
H1A C1 H1B . . 107.4 ?
C1 C2 C3 . . 113.10(12) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C4 C3 C2 . . 115.65(13) ?
C4 C3 H3A . . 108.4 ?
C2 C3 H3A . . 108.4 ?
C4 C3 H3B . . 108.4 ?
C2 C3 H3B . . 108.4 ?
H3A C3 H3B . . 107.4 ?
C3 C4 C5 . . 115.99(13) ?
C3 C4 H4A . . 108.3 ?
C5 C4 H4A . . 108.3 ?
C3 C4 H4B . . 108.3 ?
C5 C4 H4B . . 108.3 ?
H4A C4 H4B . . 107.4 ?
C4 C5 C6 . . 113.60(12) ?
C4 C5 H5A . . 108.8 ?
C6 C5 H5A . . 108.8 ?
C4 C5 H5B . . 108.8 ?
C6 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
C5 C6 C7 . . 116.11(12) ?
C5 C6 H6A . . 108.3 ?
C7 C6 H6A . . 108.3 ?
C5 C6 H6B . . 108.3 ?
C7 C6 H6B . . 108.3 ?
H6A C6 H6B . . 107.4 ?
N1 C7 N2 . . 107.14(10) ?
N1 C7 C6 . . 108.14(11) ?
N2 C7 C6 . . 109.00(10) ?
N1 C7 C1 . . 110.33(10) ?
N2 C7 C1 . . 109.07(11) ?
C6 C7 C1 . . 112.98(11) ?
O1 C8 N1 . . 121.95(12) ?
O1 C8 C9 . . 122.43(12) ?
N1 C8 C9 . . 115.49(11) ?
C12 C9 C10 . . 115.88(12) ?
C12 C9 C8 . . 123.65(11) ?
C10 C9 C8 . . 119.55(11) ?
N3 C10 N2 . . 119.12(11) ?
N3 C10 C9 . . 122.00(12) ?
N2 C10 C9 . . 118.83(12) ?
N5 C11 N3 . . 117.18(12) ?
N5 C11 N4 . . 115.99(12) ?
N3 C11 N4 . . 126.82(12) ?
N4 C12 C9 . . 123.97(12) ?
N4 C12 H12 . . 118.0 ?
C9 C12 H12 . . 118.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag

C7 C1 C2 C3 . . . . 90.57(16) ?
C1 C2 C3 C4 . . . . -67.94(19) ?
C2 C3 C4 C5 . . . . 50.1(2) ?
C3 C4 C5 C6 . . . . -71.13(19) ?
C4 C5 C6 C7 . . . . 88.34(16) ?
C8 N1 C7 N2 . . . . -41.57(16) ?
C8 N1 C7 C6 . . . . -158.93(12) ?
C8 N1 C7 C1 . . . . 77.05(15) ?
C10 N2 C7 N1 . . . . 42.90(16) ?
C10 N2 C7 C6 . . . . 159.69(12) ?
C10 N2 C7 C1 . . . . -76.53(15) ?
C5 C6 C7 N1 . . . . -158.50(11) ?
C5 C6 C7 N2 . . . . 85.34(14) ?
C5 C6 C7 C1 . . . . -36.09(16) ?
C2 C1 C7 N1 . . . . 76.85(14) ?
C2 C1 C7 N2 . . . . -165.72(11) ?
C2 C1 C7 C6 . . . . -44.33(15) ?
C7 N1 C8 O1 . . . . -168.59(12) ?
C7 N1 C8 C9 . . . . 15.46(18) ?
O1 C8 C9 C12 . . . . 5.9(2) ?
N1 C8 C9 C12 . . . . -178.21(12) ?
O1 C8 C9 C10 . . . . -162.74(13) ?
N1 C8 C9 C10 . . . . 13.19(18) ?
C11 N3 C10 N2 . . . . 179.16(12) ?
C11 N3 C10 C9 . . . . 1.64(19) ?
C7 N2 C10 N3 . . . . 162.87(12) ?
C7 N2 C10 C9 . . . . -19.52(19) ?
C12 C9 C10 N3 . . . . -2.94(19) ?
C8 C9 C10 N3 . . . . 166.53(12) ?
C12 C9 C10 N2 . . . . 179.53(12) ?
C8 C9 C10 N2 . . . . -11.01(19) ?
C10 N3 C11 N5 . . . . -178.86(12) ?
C10 N3 C11 N4 . . . . 2.2(2) ?
C12 N4 C11 N5 . . . . 176.75(13) ?
C12 N4 C11 N3 . . . . -4.3(2) ?
C11 N4 C12 C9 . . . . 2.6(2) ?
C10 C9 C12 N4 . . . . 0.7(2) ?
C8 C9 C12 N4 . . . . -168.33(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA

N1 H1N O1 3_656 0.88(2) 2.05(2) 2.9176(16) 167(2)
N2 H2N O1 4_666 0.87(2) 2.30(2) 3.1587(16) 168.3(17)
N5 H0B O1 2_655 0.84(2) 2.22(2) 2.9234(17) 141.4(19)
N5 H0A N3 3_766 0.87(2) 2.11(2) 2.9826(18) 172.5(17)
_database_code_depnum_ccdc_archive 'CCDC 896461'
