# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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data_mel_cyan

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 N3 O3, C3 H6 N6'
_chemical_formula_sum            'C12 H18 N18 O6'
_chemical_formula_weight         510.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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   'I 2/m'
_symmetry_space_group_name_Hall  '-I 2y'

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

_cell_length_a                   14.8152(19)
_cell_length_b                   9.6353(18)
_cell_length_c                   7.0405(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.194(11)
_cell_angle_gamma                90.00
_cell_volume                     1003.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6024
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.45

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale grey'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   
;
A face-indexed absorption correction employing
the Tompa method was implemented within the Stoe
X-AREA suite of programs.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Stoe IPDS2'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7067
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         29.19
_reflns_number_total             1434
_reflns_number_gt                756
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXS-86
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

Simply doubling the Rao cell (C2/m) along c, allows for either C2/m or
I2/m
to be the correct cell in the same setting.

The intensity statistics show that the true choice is I2/m.

For a truly C-centred cell, 7088 reflections with h+k=2n+1 would have
zero
intensity. However, of these 155 have I> 4sigma(I).
For a truly I-centred cell, 7044 reflections with h+k+l=2n+1 would have
zero
intensity. We do not observe any reflections in this group with
I/4sigma(I).

The data unambigously show the cell is body-centred.

Refinements carried out in C2/m are stable, but lead to non-positive
definite
displacement parameters for C/N/O. There are no such problems with the
refinement in I2/m.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1434
_refine_ls_number_parameters     113
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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
N1 N 0.16659(12) 0.0000 1.0461(3) 0.0217(4) Uani 1 2 d S . .
C2 C 0.24805(12) 0.0000 0.9759(3) 0.0188(4) Uani 1 2 d S . .
N3 N 0.28665(7) 0.12475(11) 0.94323(18) 0.0193(3) Uani 1 1 d . . .
C4 C 0.36874(8) 0.11928(14) 0.8662(2) 0.0191(3) Uani 1 1 d . . .
N5 N 0.41157(12) 0.0000 0.8219(3) 0.0197(4) Uani 1 2 d SD . .
N6 N 0.40912(8) 0.23822(13) 0.8297(2) 0.0210(3) Uani 1 1 d . . .
O10 O 0.82863(10) 0.0000 0.4514(2) 0.0221(4) Uani 1 2 d S . .
C11 C 0.75466(12) 0.0000 0.5231(3) 0.0188(4) Uani 1 2 d S . .
N12 N 0.71042(8) -0.12093(12) 0.56356(19) 0.0197(3) Uani 1 1 d . . .
C13 C 0.62677(8) -0.12571(14) 0.6373(2) 0.0191(3) Uani 1 1 d . . .
N14 N 0.58790(11) 0.0000 0.6757(3) 0.0198(4) Uani 1 2 d SD . .
O15 O 0.58833(6) -0.23661(10) 0.66794(18) 0.0237(3) Uani 1 1 d . . .
H5 H 0.461(5) 0.0000 0.767(11) 0.021(7) Uiso 0.34(4) 2 d SPD . .
H1 H 0.1387(12) 0.077(2) 1.076(3) 0.036(5) Uiso 1 1 d . . .
H6A H 0.4615(13) 0.2399(19) 0.780(3) 0.028(4) Uiso 1 1 d . . .
H6B H 0.3834(13) 0.312(2) 0.859(3) 0.032(4) Uiso 1 1 d . . .
H12 H 0.7357(14) -0.194(3) 0.530(3) 0.050(6) Uiso 1 1 d . . .
H14 H 0.531(3) 0.0000 0.724(6) 0.021(7) Uiso 0.66(4) 2 d SPD A 2

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
N1 0.0194(8) 0.0140(8) 0.0326(12) 0.000 0.0105(8) 0.000
C2 0.0180(9) 0.0172(9) 0.0214(12) 0.000 0.0035(8) 0.000
N3 0.0178(5) 0.0170(6) 0.0236(8) 0.0010(5) 0.0048(5) -0.0011(4)
C4 0.0197(7) 0.0164(7) 0.0213(8) -0.0006(6) 0.0021(6) -0.0002(5)
N5 0.0201(8) 0.0150(8) 0.0243(11) 0.000 0.0049(7) 0.000
N6 0.0193(5) 0.0137(6) 0.0309(8) -0.0011(5) 0.0098(5) -0.0001(4)
O10 0.0213(7) 0.0171(7) 0.0284(10) 0.000 0.0067(6) 0.000
C11 0.0200(9) 0.0155(9) 0.0210(12) 0.000 0.0029(8) 0.000
N12 0.0209(6) 0.0124(6) 0.0263(8) -0.0015(5) 0.0071(5) 0.0011(4)
C13 0.0188(6) 0.0172(7) 0.0215(8) -0.0002(6) 0.0039(6) 0.0005(5)
N14 0.0190(8) 0.0148(8) 0.0262(11) 0.000 0.0072(7) 0.000
O15 0.0236(5) 0.0158(5) 0.0323(7) 0.0005(5) 0.0080(4) -0.0014(4)

_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
N1 C2 1.330(2) . ?
N1 H1 0.88(2) . ?
C2 N3 1.3562(14) . ?
C2 N3 1.3562(14) 6 ?
N3 C4 1.3600(17) . ?
C4 N6 1.3244(16) . ?
C4 N5 1.3575(16) . ?
N5 C4 1.3575(16) 6 ?
N5 H5 0.85(8) . ?
N6 H6A 0.87(2) . ?
N6 H6B 0.84(2) . ?
O10 C11 1.232(2) . ?
C11 N12 1.3746(15) 6 ?
C11 N12 1.3746(15) . ?
N12 C13 1.3708(17) . ?
N12 H12 0.84(3) . ?
C13 O15 1.2354(14) . ?
C13 N14 1.3746(15) . ?
N14 C13 1.3746(15) 6 ?
N14 H14 0.93(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
C2 N1 H1 122.4(13) . . ?
N1 C2 N3 117.59(8) . . ?
N1 C2 N3 117.59(8) . 6 ?
N3 C2 N3 124.82(17) . 6 ?
C2 N3 C4 115.35(11) . . ?
N6 C4 N5 117.78(12) . . ?
N6 C4 N3 117.86(11) . . ?
N5 C4 N3 124.35(12) . . ?
C4 N5 C4 115.69(17) 6 . ?
C4 N5 H5 122.15(12) 6 . ?
C4 N5 H5 122.15(13) . . ?
C4 N6 H6A 121.2(12) . . ?
C4 N6 H6B 117.9(13) . . ?
H6A N6 H6B 120.9(18) . . ?
O10 C11 N12 122.03(8) . 6 ?
O10 C11 N12 122.03(8) . . ?
N12 C11 N12 115.92(16) 6 . ?
C13 N12 C11 123.97(12) . . ?
C13 N12 H12 120.3(14) . . ?
C11 N12 H12 115.5(15) . . ?
O15 C13 N12 122.04(11) . . ?
O15 C13 N14 121.70(12) . . ?
N12 C13 N14 116.26(12) . . ?
C13 N14 C13 123.58(16) 6 . ?
C13 N14 H14 118.16(11) 6 . ?
C13 N14 H14 118.16(11) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048



_database_code_depnum_ccdc_archive 'CCDC 935325'