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


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#
#                 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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data_cohn1
_database_code_depnum_ccdc_archive 'CCDC 900712'
#TrackingRef 'cohn1.cif'
_audit_update_record             
;
2011-04-14 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N6 O2'
_chemical_formula_weight         326.36
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/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                   10.6775(7)
_cell_length_b                   5.5932(4)
_cell_length_c                   26.0030(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.474(1)
_cell_angle_gamma                90.00
_cell_volume                     1552.42(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.91
_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29594
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3571
_reflns_number_gt                2799
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Bruker APEX2 DUO(Bruker, 2008)'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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.
The protons on N10 were obtained from a Difference Fourier map and refined
freely.
;
_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^)+(0.0539P)^2^+0.2518P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3571
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.68334(10) 1.1221(2) 0.02842(4) 0.0202(3) Uani 1 1 d . . .
C2 C 0.79857(12) 1.0462(3) 0.01622(5) 0.0201(3) Uani 1 1 d . . .
N3 N 0.86298(10) 0.8577(2) 0.03540(4) 0.0202(3) Uani 1 1 d . . .
C4 C 0.79584(12) 0.7420(2) 0.07060(5) 0.0183(3) Uani 1 1 d . . .
C5 C 0.67592(12) 0.7959(2) 0.08679(5) 0.0175(3) Uani 1 1 d . . .
C6 C 0.61754(12) 1.0003(2) 0.06323(5) 0.0179(3) Uani 1 1 d . . .
N7 N 0.63999(10) 0.6363(2) 0.12395(4) 0.0181(2) Uani 1 1 d . . .
C8 C 0.73603(12) 0.4902(2) 0.12995(5) 0.0179(3) Uani 1 1 d . . .
N9 N 0.83399(10) 0.5451(2) 0.09814(4) 0.0184(2) Uani 1 1 d . . .
N10 N 0.85480(12) 1.1755(3) -0.02084(5) 0.0266(3) Uani 1 1 d . . .
H10A H 0.8179(16) 1.309(3) -0.0318(7) 0.034(5) Uiso 1 1 d . . .
H10B H 0.9358(18) 1.160(3) -0.0257(6) 0.034(5) Uiso 1 1 d . . .
N11 N 0.50161(10) 1.0774(2) 0.07309(4) 0.0203(3) Uani 1 1 d . . .
C12 C 0.45165(13) 1.2934(3) 0.04895(6) 0.0244(3) Uani 1 1 d . . .
H12A H 0.4564 1.4259 0.0736 0.037 Uiso 1 1 calc R . .
H12B H 0.3641 1.2669 0.0382 0.037 Uiso 1 1 calc R . .
H12C H 0.5008 1.3327 0.0188 0.037 Uiso 1 1 calc R . .
C13 C 0.42048(12) 0.9651(3) 0.10999(5) 0.0221(3) Uani 1 1 d . . .
H13A H 0.4593 0.8168 0.1226 0.033 Uiso 1 1 calc R . .
H13B H 0.3394 0.9285 0.0933 0.033 Uiso 1 1 calc R . .
H13C H 0.4080 1.0741 0.1389 0.033 Uiso 1 1 calc R . .
C14 C 0.74062(12) 0.2906(2) 0.16672(5) 0.0195(3) Uani 1 1 d . . .
O15 O 0.83334(9) 0.17490(18) 0.17715(4) 0.0273(2) Uani 1 1 d . . .
O16 O 0.62933(9) 0.25564(18) 0.18788(4) 0.0237(2) Uani 1 1 d . . .
C17 C 0.62667(15) 0.0660(3) 0.22575(6) 0.0282(3) Uani 1 1 d . . .
H17A H 0.6442 -0.0872 0.2091 0.042 Uiso 1 1 calc R . .
H17B H 0.5437 0.0601 0.2410 0.042 Uiso 1 1 calc R . .
H17C H 0.6903 0.0968 0.2528 0.042 Uiso 1 1 calc R . .
C18 C 0.95757(12) 0.4348(2) 0.09457(5) 0.0201(3) Uani 1 1 d . . .
H18A H 0.9874 0.4542 0.0591 0.024 Uiso 1 1 calc R . .
H18B H 0.9501 0.2613 0.1014 0.024 Uiso 1 1 calc R . .
C19 C 1.05365(12) 0.5408(2) 0.13183(5) 0.0177(3) Uani 1 1 d . . .
C20 C 1.03172(13) 0.7505(2) 0.15867(5) 0.0211(3) Uani 1 1 d . . .
H20 H 0.9540 0.8312 0.1540 0.025 Uiso 1 1 calc R . .
C21 C 1.12240(13) 0.8433(3) 0.19232(5) 0.0239(3) Uani 1 1 d . . .
H21 H 1.1063 0.9865 0.2106 0.029 Uiso 1 1 calc R . .
C22 C 1.23605(13) 0.7279(3) 0.19923(6) 0.0251(3) Uani 1 1 d . . .
H22 H 1.2981 0.7913 0.2223 0.030 Uiso 1 1 calc R . .
C23 C 1.25899(13) 0.5194(3) 0.17238(6) 0.0263(3) Uani 1 1 d . . .
H23 H 1.3371 0.4399 0.1769 0.032 Uiso 1 1 calc R . .
C24 C 1.16831(13) 0.4259(3) 0.13883(6) 0.0228(3) Uani 1 1 d . . .
H24 H 1.1847 0.2827 0.1205 0.027 Uiso 1 1 calc R . .
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 0.0183(6) 0.0207(6) 0.0216(6) 0.0011(5) -0.0010(4) -0.0029(5)
C2 0.0184(6) 0.0229(7) 0.0190(7) -0.0015(6) -0.0010(5) -0.0050(5)
N3 0.0169(5) 0.0220(6) 0.0217(6) 0.0009(5) 0.0012(4) -0.0019(5)
C4 0.0178(6) 0.0176(6) 0.0193(7) -0.0026(5) -0.0020(5) -0.0011(5)
C5 0.0163(6) 0.0176(6) 0.0185(6) -0.0015(5) -0.0003(5) -0.0017(5)
C6 0.0178(6) 0.0170(6) 0.0189(7) -0.0020(5) -0.0010(5) -0.0025(5)
N7 0.0187(5) 0.0165(5) 0.0190(6) -0.0006(5) -0.0006(4) -0.0001(4)
C8 0.0175(6) 0.0174(7) 0.0189(7) -0.0018(5) 0.0006(5) -0.0011(5)
N9 0.0161(5) 0.0172(5) 0.0221(6) -0.0013(5) 0.0004(4) 0.0002(4)
N10 0.0193(6) 0.0315(7) 0.0290(7) 0.0101(6) 0.0020(5) -0.0015(5)
N11 0.0180(6) 0.0191(6) 0.0237(6) 0.0028(5) 0.0012(4) 0.0017(4)
C12 0.0214(7) 0.0216(7) 0.0303(8) 0.0060(6) 0.0000(6) 0.0036(6)
C13 0.0176(6) 0.0215(7) 0.0272(8) 0.0030(6) 0.0028(5) 0.0010(5)
C14 0.0227(7) 0.0155(6) 0.0203(7) -0.0032(5) 0.0008(5) 0.0006(5)
O15 0.0260(5) 0.0223(5) 0.0338(6) 0.0033(5) 0.0023(4) 0.0076(4)
O16 0.0234(5) 0.0240(5) 0.0239(5) 0.0059(4) 0.0040(4) 0.0016(4)
C17 0.0360(8) 0.0237(7) 0.0250(8) 0.0058(6) 0.0058(6) -0.0011(6)
C18 0.0167(6) 0.0188(7) 0.0247(7) -0.0028(6) 0.0025(5) 0.0021(5)
C19 0.0167(6) 0.0163(6) 0.0203(7) 0.0032(5) 0.0035(5) -0.0001(5)
C20 0.0198(6) 0.0188(7) 0.0249(7) 0.0012(6) 0.0015(5) 0.0029(5)
C21 0.0283(7) 0.0189(7) 0.0247(7) -0.0008(6) 0.0007(6) -0.0008(6)
C22 0.0230(7) 0.0277(8) 0.0245(7) 0.0036(6) -0.0024(6) -0.0053(6)
C23 0.0185(7) 0.0287(8) 0.0316(8) 0.0043(6) -0.0012(6) 0.0040(6)
C24 0.0213(7) 0.0194(7) 0.0278(7) 0.0008(6) 0.0039(5) 0.0030(5)
_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 C6 1.3453(17) . ?
N1 C2 1.3471(17) . ?
C2 N3 1.3475(18) . ?
C2 N10 1.3570(18) . ?
N3 C4 1.3434(17) . ?
C4 N9 1.3696(17) . ?
C4 C5 1.3913(18) . ?
C5 N7 1.3772(17) . ?
C5 C6 1.4323(18) . ?
C6 N11 1.3417(16) . ?
N7 C8 1.3173(17) . ?
C8 N9 1.3846(17) . ?
C8 C14 1.4697(19) . ?
N9 C18 1.4620(16) . ?
N10 H10A 0.888(19) . ?
N10 H10B 0.881(18) . ?
N11 C13 1.4521(17) . ?
N11 C12 1.4564(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O15 1.2078(16) . ?
C14 O16 1.3368(16) . ?
O16 C17 1.4479(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.5139(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3875(19) . ?
C19 C24 1.3904(18) . ?
C20 C21 1.3888(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
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
C6 N1 C2 119.65(12) . . ?
N1 C2 N3 128.32(12) . . ?
N1 C2 N10 115.01(13) . . ?
N3 C2 N10 116.66(12) . . ?
C4 N3 C2 110.68(11) . . ?
N3 C4 N9 125.94(12) . . ?
N3 C4 C5 127.81(12) . . ?
N9 C4 C5 106.24(11) . . ?
N7 C5 C4 110.29(11) . . ?
N7 C5 C6 133.75(12) . . ?
C4 C5 C6 115.94(12) . . ?
N11 C6 N1 117.79(12) . . ?
N11 C6 C5 124.63(12) . . ?
N1 C6 C5 117.58(12) . . ?
C8 N7 C5 104.79(11) . . ?
N7 C8 N9 112.91(12) . . ?
N7 C8 C14 124.13(12) . . ?
N9 C8 C14 122.96(11) . . ?
C4 N9 C8 105.76(11) . . ?
C4 N9 C18 124.26(11) . . ?
C8 N9 C18 129.88(11) . . ?
C2 N10 H10A 118.3(11) . . ?
C2 N10 H10B 120.2(11) . . ?
H10A N10 H10B 117.8(16) . . ?
C6 N11 C13 123.80(11) . . ?
C6 N11 C12 120.91(11) . . ?
C13 N11 C12 115.18(11) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O15 C14 O16 124.14(13) . . ?
O15 C14 C8 124.51(12) . . ?
O16 C14 C8 111.34(11) . . ?
C14 O16 C17 114.85(11) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N9 C18 C19 113.07(11) . . ?
N9 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N9 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C24 118.96(13) . . ?
C20 C19 C18 122.19(12) . . ?
C24 C19 C18 118.85(12) . . ?
C19 C20 C21 120.58(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.19(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.60(13) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 120.30(13) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.36(13) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10B N3 0.881(18) 2.172(19) 3.0524(17) 176.6(17) 3_775
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044