# 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
#  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_5-isopropyl-6-methylisocytosine_cocrystal

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 N3 O, C4 H5 N3 O, H2 O'
_chemical_formula_sum            'C12 H20 N6 O3'
_chemical_formula_weight         296.34

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

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                   15.5249(9)
_cell_length_b                   5.5769(3)
_cell_length_c                   18.7323(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.714(3)
_cell_angle_gamma                90.00
_cell_volume                     1496.07(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      19.53

_exptl_crystal_description       'thin plates'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   multi-scan

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9737
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25
_reflns_number_total             2639
_reflns_number_gt                2231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2639
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_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
C6 C 0.9432(2) 0.8310(5) 0.63869(17) 0.0565(9) Uani 1 1 d . . .
H1 H 0.8882 0.7268 0.6238 0.068 Uiso 1 1 calc R . .
C8 C 1.0218(2) 0.6807(6) 0.6329(2) 0.0816(11) Uani 1 1 d . . .
H2A H 1.0763 0.7788 0.6444 0.122 Uiso 1 1 calc R . .
H2B H 1.0030 0.6175 0.5815 0.122 Uiso 1 1 calc R . .
H2C H 1.0357 0.5509 0.6693 0.122 Uiso 1 1 calc R . .
C7 C 0.9178(3) 1.0372(6) 0.58086(18) 0.0854(12) Uani 1 1 d . . .
H3A H 0.9707 1.1412 0.5923 0.128 Uiso 1 1 calc R . .
H3B H 0.8666 1.1258 0.5844 0.128 Uiso 1 1 calc R . .
H3C H 0.9002 0.9744 0.5294 0.128 Uiso 1 1 calc R . .
O1 O 1.10139(14) 1.1335(3) 0.73520(11) 0.0543(7) Uani 1 1 d . . .
C5 C 0.8253(2) 0.6855(7) 0.7271(2) 0.0854(12) Uani 1 1 d . . .
H4A H 0.7779 0.7487 0.6810 0.128 Uiso 1 1 calc R . .
H4B H 0.7992 0.6570 0.7652 0.128 Uiso 1 1 calc R . .
H4C H 0.8484 0.5375 0.7152 0.128 Uiso 1 1 calc R . .
C3 C 0.9622(2) 0.9199(5) 0.72033(16) 0.0471(8) Uani 1 1 d . . .
C1 C 0.9785(2) 1.1232(5) 0.85828(18) 0.0478(9) Uani 1 1 d . . .
N1 N 0.98675(17) 1.2401(5) 0.92251(15) 0.0716(9) Uani 1 1 d . . .
H1A H 0.9487 1.2104 0.9448 0.086 Uiso 1 1 calc R . .
H1B H 1.0301 1.3453 0.9418 0.086 Uiso 1 1 calc R . .
O2 O 0.11942(16) 0.6292(3) 0.98888(12) 0.0645(7) Uani 1 1 d . . .
N6 N 0.24629(17) 0.4921(4) 0.81055(14) 0.0573(8) Uani 1 1 d . . .
H2D H 0.2127 0.3650 0.7960 0.069 Uiso 1 1 calc R . .
H2E H 0.2842 0.5309 0.7890 0.069 Uiso 1 1 calc R . .
N5 N 0.17911(17) 0.5588(4) 0.89763(14) 0.0481(7) Uani 1 1 d . . .
N4 N 0.22034(18) 0.9010(5) 0.97687(16) 0.0504(8) Uani 1 1 d . . .
C9 C 0.1711(2) 0.6908(5) 0.95469(17) 0.0464(8) Uani 1 1 d . . .
C11 C 0.2939(2) 0.8370(6) 0.89038(18) 0.0525(9) Uani 1 1 d . . .
H8 H 0.3371 0.8809 0.8695 0.063 Uiso 1 1 calc R . .
C10 C 0.2396(2) 0.6283(5) 0.86606(17) 0.0440(8) Uani 1 1 d . . .
C12 C 0.2809(2) 0.9696(6) 0.94462(18) 0.0544(9) Uani 1 1 d . . .
H9 H 0.3140 1.1118 0.9606 0.065 Uiso 1 1 calc R . .
N2 N 1.04094(18) 1.1757(5) 0.82605(14) 0.0467(7) Uani 1 1 d . . .
N3 N 0.91252(17) 0.9610(5) 0.82773(15) 0.0548(8) Uani 1 1 d . . .
C2 C 1.0384(2) 1.0764(5) 0.75780(17) 0.0447(8) Uani 1 1 d . . .
C4 C 0.9044(2) 0.8635(5) 0.75838(19) 0.0537(9) Uani 1 1 d . . .
O3 O 0.19442(17) 0.2043(5) 0.08641(15) 0.0666(7) Uani 1 1 d . . .
H20 H 0.2096(19) 0.996(5) 1.0118(17) 0.051(10) Uiso 1 1 d . . .
H21 H 1.085(2) 1.296(5) 0.8496(17) 0.061(10) Uiso 1 1 d . . .
H22 H 0.169(3) 0.341(7) 0.062(2) 0.112(17) Uiso 1 1 d . . .
H23 H 0.161(3) 0.161(6) 0.113(2) 0.099(15) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C6 0.050(2) 0.061(2) 0.058(2) -0.0129(18) 0.0210(17) -0.0077(17)
C8 0.084(3) 0.078(2) 0.085(3) -0.0183(19) 0.034(2) 0.016(2)
C7 0.110(3) 0.078(3) 0.057(2) 0.000(2) 0.019(2) 0.020(2)
O1 0.0483(14) 0.0681(14) 0.0625(14) -0.0114(11) 0.0390(12) -0.0078(10)
C5 0.077(3) 0.105(3) 0.086(3) -0.031(2) 0.045(2) -0.046(2)
C3 0.042(2) 0.055(2) 0.050(2) -0.0088(17) 0.0237(18) -0.0017(17)
C1 0.040(2) 0.059(2) 0.050(2) -0.0052(18) 0.0249(19) -0.0057(17)
N1 0.0728(19) 0.094(2) 0.070(2) -0.0311(17) 0.0518(16) -0.0326(16)
O2 0.0774(16) 0.0653(15) 0.0759(16) -0.0139(12) 0.0573(14) -0.0164(11)
N6 0.0639(18) 0.0626(17) 0.0649(18) -0.0113(15) 0.0463(15) -0.0172(13)
N5 0.0536(17) 0.0540(16) 0.0504(16) -0.0069(14) 0.0352(14) -0.0088(13)
N4 0.0594(19) 0.0497(18) 0.0509(17) -0.0036(15) 0.0311(16) -0.0073(15)
C9 0.048(2) 0.049(2) 0.049(2) 0.0002(17) 0.0270(18) -0.0042(17)
C11 0.052(2) 0.062(2) 0.051(2) 0.0011(17) 0.0286(17) -0.0140(18)
C10 0.041(2) 0.051(2) 0.045(2) 0.0035(17) 0.0220(17) -0.0025(16)
C12 0.058(2) 0.054(2) 0.055(2) 0.0044(18) 0.0270(19) -0.0139(17)
N2 0.0412(17) 0.0591(18) 0.0503(18) -0.0114(14) 0.0291(15) -0.0142(14)
N3 0.0496(18) 0.0667(18) 0.0569(18) -0.0106(15) 0.0302(15) -0.0152(15)
C2 0.042(2) 0.0504(19) 0.047(2) -0.0052(17) 0.0237(18) 0.0021(17)
C4 0.047(2) 0.059(2) 0.059(2) -0.0053(18) 0.0252(18) -0.0054(17)
O3 0.0772(18) 0.0663(18) 0.0704(17) -0.0013(13) 0.0440(15) -0.0063(14)

_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
C6 C8 1.518(4) . ?
C6 C7 1.523(4) . ?
C6 C3 1.524(4) . ?
O1 C2 1.248(3) . ?
C5 C4 1.511(4) . ?
C3 C4 1.381(4) . ?
C3 C2 1.418(4) . ?
C1 N3 1.320(4) . ?
C1 N1 1.330(3) . ?
C1 N2 1.357(3) . ?
O2 C9 1.253(3) . ?
N6 C10 1.323(3) . ?
N5 C9 1.343(3) . ?
N5 C10 1.346(3) . ?
N4 C12 1.354(4) . ?
N4 C9 1.373(4) . ?
C11 C12 1.333(4) . ?
C11 C10 1.406(4) . ?
N2 C2 1.380(3) . ?
N3 C4 1.368(4) . ?

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
C8 C6 C7 111.1(3) . . ?
C8 C6 C3 113.6(3) . . ?
C7 C6 C3 111.4(3) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 C6 122.1(3) . . ?
C2 C3 C6 119.9(3) . . ?
N3 C1 N1 121.0(3) . . ?
N3 C1 N2 121.5(3) . . ?
N1 C1 N2 117.4(3) . . ?
C9 N5 C10 119.1(3) . . ?
C12 N4 C9 120.5(3) . . ?
O2 C9 N5 122.1(3) . . ?
O2 C9 N4 118.1(3) . . ?
N5 C9 N4 119.8(3) . . ?
C12 C11 C10 117.3(3) . . ?
N6 C10 N5 117.4(3) . . ?
N6 C10 C11 120.7(3) . . ?
N5 C10 C11 121.9(3) . . ?
C11 C12 N4 121.2(3) . . ?
C1 N2 C2 123.8(3) . . ?
C1 N3 C4 117.1(2) . . ?
O1 C2 N2 117.8(3) . . ?
O1 C2 C3 127.0(3) . . ?
N2 C2 C3 115.2(3) . . ?
N3 C4 C3 124.0(3) . . ?
N3 C4 C5 113.1(3) . . ?
C3 C4 C5 122.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 980516'
#######################################################################
#
#                 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_5-methyl-6-isopropylisocytosine_tautomer

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H13 N3 O), H2 O'
_chemical_formula_sum            'C16 H28 N6 O3'
_chemical_formula_weight         352.44

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_space_group_name_Hall           '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.3425(7)
_cell_length_b                   13.9961(7)
_cell_length_c                   14.4876(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.855(3)
_cell_angle_gamma                90.00
_cell_volume                     3808.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17056
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25
_reflns_number_total             3352
_reflns_number_gt                2518
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     256
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.552
_refine_ls_shift/su_max          0.006
_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
C4 C 0.3221(2) 0.3843(3) 0.6770(3) 0.0441(12) Uani 1 1 d . . .
C1 C 0.3116(2) 0.2243(3) 0.6441(3) 0.0430(12) Uani 1 1 d . . .
C5 C 0.3952(3) 0.4519(3) 0.8332(3) 0.0586(14) Uani 1 1 d . . .
H5 H 0.3853 0.5111 0.7962 0.070 Uiso 1 1 calc R . .
C2 C 0.3808(2) 0.2749(3) 0.7970(3) 0.0470(12) Uani 1 1 d . . .
C3 C 0.3654(2) 0.3708(3) 0.7662(3) 0.0444(12) Uani 1 1 d . . .
C7 C 0.3579(3) 0.4604(4) 0.9138(4) 0.0770(17) Uani 1 1 d . . .
H7A H 0.3077 0.4688 0.8880 0.116 Uiso 1 1 calc R . .
H7B H 0.3765 0.5145 0.9526 0.116 Uiso 1 1 calc R . .
H7C H 0.3660 0.4034 0.9516 0.116 Uiso 1 1 calc R . .
C6 C 0.4760(3) 0.4471(5) 0.8723(4) 0.103(2) Uani 1 1 d . . .
H6A H 0.4873 0.3984 0.9203 0.154 Uiso 1 1 calc R . .
H6B H 0.4931 0.5077 0.8995 0.154 Uiso 1 1 calc R . .
H6C H 0.4984 0.4321 0.8216 0.154 Uiso 1 1 calc R . .
C12 C 0.3891(2) 0.8246(3) 0.8567(4) 0.0502(12) Uani 1 1 d . . .
C10 C 0.3788(2) 0.9427(3) 0.7341(4) 0.0529(13) Uani 1 1 d . . .
C11 C 0.3781(2) 0.8427(3) 0.7627(3) 0.0496(12) Uani 1 1 d . . .
C9 C 0.3940(2) 0.9904(3) 0.8909(3) 0.0480(12) Uani 1 1 d . . .
C13 C 0.3646(3) 0.7642(4) 0.6888(4) 0.0706(16) Uani 1 1 d . . .
H13 H 0.3668 0.7060 0.7270 0.085 Uiso 1 1 calc R . .
C15 C 0.4220(3) 0.7498(5) 0.6383(4) 0.095(2) Uani 1 1 d . . .
H15A H 0.4339 0.8099 0.6142 0.142 Uiso 1 1 calc R . .
H15B H 0.4060 0.7061 0.5865 0.142 Uiso 1 1 calc R . .
H15C H 0.4633 0.7240 0.6816 0.142 Uiso 1 1 calc R . .
C14 C 0.2921(4) 0.7626(5) 0.6289(5) 0.126(3) Uani 1 1 d . . .
H14A H 0.2835 0.8200 0.5917 0.189 Uiso 1 1 calc R . .
H14B H 0.2588 0.7585 0.6683 0.189 Uiso 1 1 calc R . .
H14C H 0.2865 0.7082 0.5874 0.189 Uiso 1 1 calc R . .
N5 N 0.35178(19) 0.2051(3) 0.7325(2) 0.0475(10) Uani 1 1 d . . .
H5A H 0.3596 0.1464 0.7490 0.057 Uiso 1 1 calc R . .
N2 N 0.3851(2) 1.0137(3) 0.8006(3) 0.0544(11) Uani 1 1 d . . .
N4 N 0.29488(18) 0.3121(3) 0.6149(2) 0.0459(10) Uani 1 1 d . . .
N1 N 0.39840(19) 0.8989(3) 0.9204(2) 0.0501(10) Uani 1 1 d . . .
H1 H 0.4072 0.8867 0.9803 0.060 Uiso 1 1 calc R . .
N6 N 0.2876(2) 0.1492(3) 0.5880(3) 0.0558(12) Uani 1 1 d . . .
N3 N 0.3984(3) 1.0589(4) 0.9561(4) 0.0655(14) Uani 1 1 d . . .
O1 O 0.41676(18) 0.2486(2) 0.8771(2) 0.0620(10) Uani 1 1 d . . .
O2 O 0.3733(2) 0.9677(2) 0.6496(2) 0.0751(11) Uani 1 1 d . . .
C8 C 0.2992(3) 0.4820(3) 0.6383(3) 0.0660(15) Uani 1 1 d . . .
H8A H 0.2754 0.5143 0.6803 0.099 Uiso 1 1 calc R . .
H8B H 0.2674 0.4760 0.5766 0.099 Uiso 1 1 calc R . .
H8C H 0.3404 0.5182 0.6332 0.099 Uiso 1 1 calc R . .
C16 C 0.3934(3) 0.7279(3) 0.9033(4) 0.0692(15) Uani 1 1 d . . .
H16A H 0.3479 0.6970 0.8852 0.104 Uiso 1 1 calc R . .
H16B H 0.4068 0.7353 0.9711 0.104 Uiso 1 1 calc R . .
H16C H 0.4284 0.6896 0.8832 0.104 Uiso 1 1 calc R . .
O3 O 0.5429(2) 0.1409(4) 0.8868(3) 0.0837(12) Uani 1 1 d D . .
H3A H 0.398(2) 1.049(3) 1.015(4) 0.068(17) Uiso 1 1 d . . .
H3B H 0.398(3) 1.119(4) 0.939(4) 0.072(18) Uiso 1 1 d . . .
H6M H 0.263(2) 0.159(3) 0.528(4) 0.060(16) Uiso 1 1 d . . .
H6N H 0.306(2) 0.092(4) 0.602(3) 0.052(15) Uiso 1 1 d . . .
H3M H 0.498(2) 0.168(5) 0.878(5) 0.16(3) Uiso 1 1 d D . .
H3N H 0.539(5) 0.082(3) 0.856(5) 0.17(4) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C4 0.048(3) 0.043(3) 0.040(3) 0.002(2) 0.008(2) 0.000(2)
C1 0.044(3) 0.050(4) 0.032(3) -0.004(3) 0.004(2) 0.001(2)
C5 0.079(4) 0.050(3) 0.041(3) 0.002(2) 0.003(3) -0.009(3)
C2 0.053(3) 0.052(3) 0.034(3) -0.002(3) 0.005(2) 0.006(3)
C3 0.053(3) 0.045(3) 0.032(3) 0.000(2) 0.005(2) -0.001(2)
C7 0.102(5) 0.063(4) 0.069(4) -0.019(3) 0.028(3) 0.000(3)
C6 0.082(5) 0.143(6) 0.079(4) -0.043(4) 0.011(3) -0.037(4)
C12 0.051(3) 0.046(3) 0.056(3) -0.001(3) 0.016(2) 0.001(2)
C10 0.067(3) 0.054(4) 0.039(3) -0.002(3) 0.016(2) 0.009(2)
C11 0.056(3) 0.043(3) 0.052(3) -0.008(3) 0.017(2) 0.001(2)
C9 0.058(3) 0.043(3) 0.042(4) -0.003(3) 0.012(2) 0.001(2)
C13 0.082(4) 0.062(3) 0.070(4) -0.016(3) 0.021(3) -0.004(3)
C15 0.101(5) 0.106(5) 0.080(4) -0.032(4) 0.028(4) 0.019(4)
C14 0.087(5) 0.144(7) 0.129(6) -0.071(5) -0.012(5) 0.015(4)
N5 0.061(3) 0.043(2) 0.034(2) 0.000(2) 0.001(2) 0.008(2)
N2 0.086(3) 0.046(2) 0.033(3) 0.002(2) 0.016(2) 0.007(2)
N4 0.051(2) 0.044(3) 0.038(2) 0.003(2) 0.0009(18) 0.004(2)
N1 0.067(3) 0.045(3) 0.038(2) 0.005(2) 0.0128(19) 0.0034(19)
N6 0.066(3) 0.049(3) 0.042(3) -0.004(3) -0.007(2) 0.006(2)
N3 0.113(4) 0.048(3) 0.038(3) -0.002(3) 0.021(2) -0.002(3)
O1 0.083(2) 0.056(2) 0.036(2) 0.0010(16) -0.0079(18) 0.0102(18)
O2 0.126(3) 0.065(2) 0.037(2) 0.0008(18) 0.0246(19) 0.017(2)
C8 0.084(4) 0.054(3) 0.052(3) 0.006(3) 0.000(3) 0.001(3)
C16 0.088(4) 0.046(3) 0.079(4) 0.008(3) 0.029(3) 0.002(3)
O3 0.072(3) 0.110(4) 0.067(3) 0.011(3) 0.014(2) 0.007(3)

_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
C4 N4 1.372(5) . ?
C4 C3 1.374(6) . ?
C4 C8 1.504(6) . ?
C1 N4 1.315(5) . ?
C1 N6 1.341(6) . ?
C1 N5 1.356(5) . ?
C5 C3 1.516(6) . ?
C5 C7 1.516(7) . ?
C5 C6 1.532(7) . ?
C2 O1 1.257(5) . ?
C2 N5 1.375(5) . ?
C2 C3 1.423(6) . ?
C12 C11 1.351(6) . ?
C12 N1 1.373(6) . ?
C12 C16 1.506(6) . ?
C10 O2 1.253(5) . ?
C10 N2 1.369(6) . ?
C10 C11 1.460(6) . ?
C11 C13 1.513(6) . ?
C9 N2 1.319(5) . ?
C9 N3 1.334(6) . ?
C9 N1 1.347(5) . ?
C13 C14 1.462(8) . ?
C13 C15 1.481(8) . ?
O3 H3N 0.928(16) . ?
O3 H3M 0.932(16) . ?

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
N4 C4 C3 124.5(4) . . ?
N4 C4 C8 113.1(4) . . ?
C3 C4 C8 122.3(4) . . ?
N4 C1 N6 121.0(4) . . ?
N4 C1 N5 122.0(4) . . ?
N6 C1 N5 117.0(4) . . ?
C3 C5 C7 112.0(4) . . ?
C3 C5 C6 113.6(4) . . ?
C7 C5 C6 110.5(4) . . ?
O1 C2 N5 117.7(4) . . ?
O1 C2 C3 126.4(4) . . ?
N5 C2 C3 115.8(4) . . ?
C4 C3 C2 117.4(4) . . ?
C4 C3 C5 123.4(4) . . ?
C2 C3 C5 119.1(4) . . ?
C11 C12 N1 119.9(4) . . ?
C11 C12 C16 126.8(4) . . ?
N1 C12 C16 113.3(4) . . ?
O2 C10 N2 117.2(4) . . ?
O2 C10 C11 122.7(4) . . ?
N2 C10 C11 120.1(4) . . ?
C12 C11 C10 117.1(4) . . ?
C12 C11 C13 122.4(4) . . ?
C10 C11 C13 120.5(4) . . ?
N2 C9 N3 119.8(5) . . ?
N2 C9 N1 122.1(4) . . ?
N3 C9 N1 118.1(4) . . ?
C14 C13 C15 115.5(5) . . ?
C14 C13 C11 114.2(5) . . ?
C15 C13 C11 115.2(5) . . ?
C1 N5 C2 123.4(4) . . ?
C9 N2 C10 119.2(4) . . ?
C1 N4 C4 116.9(4) . . ?
C9 N1 C12 121.3(4) . . ?
H3N O3 H3M 110(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 980517'
#######################################################################
#
#                 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_6-phenylisocytosine_cytosine_cocrystal

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O, C4 H5 N3 O'
_chemical_formula_sum            'C14 H14 N6 O2'
_chemical_formula_weight         298.31

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4798(6)
_cell_length_b                   6.8611(5)
_cell_length_c                   17.0339(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.021(5)
_cell_angle_gamma                90.00
_cell_volume                     1452.94(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5669
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2619
_reflns_number_gt                1941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0020P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2619
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
O2 O 0.45840(11) 1.0274(2) 0.80743(9) 0.0496(4) Uani 1 1 d . . .
O1 O 0.09178(12) 0.3943(3) 0.83519(12) 0.0681(6) Uani 1 1 d . . .
N2 N 0.35723(13) 0.6276(3) 0.95477(10) 0.0379(4) Uani 1 1 d . . .
N5 N 0.37723(16) 0.7691(3) 0.74451(12) 0.0466(5) Uani 1 1 d . . .
N3 N 0.45204(13) 0.3734(3) 0.90511(11) 0.0449(5) Uani 1 1 d . . .
H3A H 0.5109 0.4167 0.9289 0.054 Uiso 1 1 calc R . .
H3B H 0.4527 0.2694 0.8770 0.054 Uiso 1 1 calc R . .
N4 N 0.27672(13) 1.0361(3) 0.78231(11) 0.0414(5) Uani 1 1 d . . .
N1 N 0.27042(14) 0.3907(3) 0.87118(11) 0.0393(5) Uani 1 1 d . . .
C10 C 0.35927(16) 0.4682(3) 0.91188(12) 0.0357(5) Uani 1 1 d . . .
C11 C 0.37343(17) 0.9489(3) 0.77951(13) 0.0398(5) Uani 1 1 d . . .
N6 N 0.09579(15) 1.0430(3) 0.75070(14) 0.0697(7) Uani 1 1 d . . .
H6A H 0.0941 1.1536 0.7743 0.084 Uiso 1 1 calc R . .
H6B H 0.0374 0.9925 0.7291 0.084 Uiso 1 1 calc R . .
C3 C 0.25980(16) 0.7206(3) 0.95500(13) 0.0383(5) Uani 1 1 d . . .
C4 C 0.26067(17) 0.9078(3) 0.99864(13) 0.0406(5) Uani 1 1 d . . .
C1 C 0.17042(17) 0.4748(4) 0.87244(14) 0.0480(6) Uani 1 1 d . . .
C9 C 0.35637(18) 0.9960(3) 1.02490(14) 0.0451(6) Uani 1 1 d . . .
H9 H 0.4208 0.9355 1.0158 0.054 Uiso 1 1 calc R . .
C12 C 0.18847(17) 0.9502(4) 0.74761(14) 0.0459(6) Uani 1 1 d . . .
C2 C 0.16826(17) 0.6485(4) 0.91554(14) 0.0494(6) Uani 1 1 d . . .
H2 H 0.1037 0.7156 0.9173 0.059 Uiso 1 1 calc R . .
C13 C 0.19260(19) 0.7681(4) 0.70863(14) 0.0515(7) Uani 1 1 d . . .
H13 H 0.1311 0.7112 0.6838 0.062 Uiso 1 1 calc R . .
C8 C 0.3590(2) 1.1724(4) 1.06446(14) 0.0523(7) Uani 1 1 d . . .
H8 H 0.4247 1.2281 1.0819 0.063 Uiso 1 1 calc R . .
C14 C 0.28812(19) 0.6822(4) 0.70911(14) 0.0517(6) Uani 1 1 d . . .
H14 H 0.2939 0.5615 0.6850 0.062 Uiso 1 1 calc R . .
C7 C 0.2657(2) 1.2647(4) 1.07792(15) 0.0608(7) Uani 1 1 d . . .
H7 H 0.2671 1.3845 1.1036 0.073 Uiso 1 1 calc R . .
C5 C 0.1667(2) 1.0023(5) 1.01391(18) 0.0731(9) Uani 1 1 d . . .
H5 H 0.1005 0.9464 0.9976 0.088 Uiso 1 1 calc R . .
C6 C 0.1701(2) 1.1784(5) 1.05309(19) 0.0823(10) Uani 1 1 d . . .
H6 H 0.1061 1.2395 1.0628 0.099 Uiso 1 1 calc R . .
H1A H 0.2749(18) 0.276(4) 0.8420(13) 0.055(7) Uiso 1 1 d . . .
H5A H 0.439(2) 0.715(4) 0.7423(15) 0.069(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0301(8) 0.0556(11) 0.0617(11) -0.0073(9) -0.0033(7) -0.0041(8)
O1 0.0371(9) 0.0574(12) 0.1032(15) -0.0204(11) -0.0314(9) 0.0068(9)
N2 0.0288(9) 0.0398(11) 0.0444(11) -0.0047(9) -0.0010(8) 0.0010(8)
N5 0.0379(11) 0.0500(13) 0.0520(13) -0.0094(10) 0.0056(9) 0.0023(10)
N3 0.0269(9) 0.0503(13) 0.0560(13) -0.0151(10) -0.0039(8) 0.0013(9)
N4 0.0292(9) 0.0440(12) 0.0496(12) -0.0059(9) -0.0040(8) -0.0026(9)
N1 0.0304(10) 0.0389(12) 0.0465(12) -0.0058(9) -0.0088(8) 0.0026(9)
C10 0.0292(11) 0.0394(14) 0.0378(12) 0.0051(10) -0.0011(9) -0.0013(10)
C11 0.0360(12) 0.0458(15) 0.0375(13) 0.0006(11) 0.0031(10) -0.0017(11)
N6 0.0320(11) 0.0678(16) 0.1053(19) -0.0312(14) -0.0167(11) -0.0001(11)
C3 0.0328(11) 0.0374(13) 0.0440(13) 0.0018(10) 0.0001(9) 0.0019(10)
C4 0.0368(12) 0.0403(14) 0.0443(13) -0.0005(11) 0.0010(10) 0.0047(11)
C1 0.0340(12) 0.0468(15) 0.0601(16) -0.0020(12) -0.0137(11) 0.0035(11)
C9 0.0425(13) 0.0394(14) 0.0530(15) 0.0022(11) 0.0024(11) 0.0009(11)
C12 0.0356(12) 0.0526(16) 0.0484(15) -0.0048(12) -0.0032(10) -0.0041(11)
C2 0.0303(12) 0.0477(16) 0.0677(17) -0.0059(13) -0.0088(11) 0.0081(11)
C13 0.0415(13) 0.0577(17) 0.0542(15) -0.0170(13) -0.0019(11) -0.0103(12)
C8 0.0621(16) 0.0402(15) 0.0537(16) 0.0009(12) -0.0004(12) -0.0051(13)
C14 0.0548(15) 0.0518(16) 0.0486(15) -0.0149(12) 0.0060(12) -0.0082(13)
C7 0.081(2) 0.0476(17) 0.0540(17) -0.0076(13) 0.0065(14) 0.0063(15)
C5 0.0401(15) 0.077(2) 0.101(2) -0.0350(19) -0.0012(15) 0.0076(15)
C6 0.0594(19) 0.081(2) 0.107(3) -0.035(2) 0.0081(17) 0.0211(17)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C11 1.246(2) . ?
O1 C1 1.250(3) . ?
N2 C10 1.316(3) . ?
N2 C3 1.373(3) . ?
N5 C14 1.356(3) . ?
N5 C11 1.373(3) . ?
N3 C10 1.342(3) . ?
N4 C12 1.340(3) . ?
N4 C11 1.352(3) . ?
N1 C10 1.363(3) . ?
N1 C1 1.377(3) . ?
N6 C12 1.325(3) . ?
C3 C2 1.366(3) . ?
C3 C4 1.483(3) . ?
C4 C9 1.378(3) . ?
C4 C5 1.385(3) . ?
C1 C2 1.401(3) . ?
C9 C8 1.384(3) . ?
C12 C13 1.418(3) . ?
C13 C14 1.329(3) . ?
C8 C7 1.362(3) . ?
C7 C6 1.366(4) . ?
C5 C6 1.379(4) . ?

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
C10 N2 C3 116.59(18) . . ?
C14 N5 C11 122.0(2) . . ?
C12 N4 C11 119.4(2) . . ?
C10 N1 C1 121.8(2) . . ?
N2 C10 N3 120.60(19) . . ?
N2 C10 N1 123.49(19) . . ?
N3 C10 N1 115.9(2) . . ?
O2 C11 N4 121.9(2) . . ?
O2 C11 N5 119.6(2) . . ?
N4 C11 N5 118.6(2) . . ?
C2 C3 N2 122.2(2) . . ?
C2 C3 C4 121.9(2) . . ?
N2 C3 C4 115.85(18) . . ?
C9 C4 C5 117.2(2) . . ?
C9 C4 C3 120.7(2) . . ?
C5 C4 C3 122.0(2) . . ?
O1 C1 N1 118.7(2) . . ?
O1 C1 C2 126.3(2) . . ?
N1 C1 C2 115.1(2) . . ?
C4 C9 C8 121.7(2) . . ?
N6 C12 N4 117.2(2) . . ?
N6 C12 C13 120.6(2) . . ?
N4 C12 C13 122.1(2) . . ?
C3 C2 C1 120.8(2) . . ?
C14 C13 C12 117.2(2) . . ?
C7 C8 C9 120.3(3) . . ?
C13 C14 N5 120.5(2) . . ?
C8 C7 C6 118.8(3) . . ?
C6 C5 C4 120.7(3) . . ?
C7 C6 C5 121.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 980518'
