# Electronic Supplementary Material (ESI) for Chemical Science.
# 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.
#
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#  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:
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#  from this site to visualise CIF-encoded structures and 
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data_l0024a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N4 O4'
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_weight         302.29

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.16538(16)
_cell_length_b                   8.20620(19)
_cell_length_c                   11.6136(3)
_cell_angle_alpha                85.818(1)
_cell_angle_beta                 88.406(1)
_cell_angle_gamma                82.354(1)
_cell_volume                     674.90(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4976
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8680
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.51
_reflns_number_total             3102
_reflns_number_gt                2591
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval14, Sadabs'
_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)+(0.0553P)²+0.2711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3102
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O -0.01803(13) 0.42466(12) 0.27108(8) 0.0237(2) Uani 1 1 d . . .
O11 O 0.60130(13) 0.57998(11) 0.36589(8) 0.0198(2) Uani 1 1 d . . .
O12 O 0.70679(14) 0.78412(12) 0.25595(9) 0.0247(2) Uani 1 1 d . . .
H12O H 0.790(3) 0.791(3) 0.316(2) 0.064(7) Uiso 1 1 d . . .
O21 O -0.47012(13) 0.20283(12) 0.43806(8) 0.0227(2) Uani 1 1 d . . .
N1 N 0.27875(15) 0.48694(14) 0.29833(10) 0.0186(2) Uani 1 1 d . . .
H1N H 0.372(3) 0.475(2) 0.3470(16) 0.031(5) Uiso 1 1 d . . .
N2 N 0.13410(15) 0.33741(14) 0.44022(10) 0.0191(2) Uani 1 1 d . . .
H2N H 0.244(3) 0.322(2) 0.4733(18) 0.043(5) Uiso 1 1 d . . .
N21 N -0.17201(15) 0.26526(13) 0.44288(10) 0.0170(2) Uani 1 1 d . . .
H21N H -0.186(2) 0.326(2) 0.3771(16) 0.027(4) Uiso 1 1 d . . .
N22 N 0.03093(14) 0.18209(13) 0.59634(9) 0.0167(2) Uani 1 1 d . . .
C1 C 0.12240(17) 0.41777(15) 0.33003(11) 0.0162(3) Uani 1 1 d . . .
C11 C 0.31230(18) 0.57130(15) 0.19134(11) 0.0171(3) Uani 1 1 d . . .
C12 C 0.47079(17) 0.65708(15) 0.17851(11) 0.0165(3) Uani 1 1 d . . .
C13 C 0.50966(18) 0.73530(16) 0.07158(11) 0.0186(3) Uani 1 1 d . . .
H13 H 0.6167 0.7926 0.0639 0.022 Uiso 1 1 calc R . .
C14 C 0.39872(19) 0.73298(16) -0.02389(11) 0.0201(3) Uani 1 1 d . . .
C15 C 0.2412(2) 0.65114(18) -0.00871(12) 0.0245(3) Uani 1 1 d . . .
H15 H 0.1609 0.6493 -0.0722 0.029 Uiso 1 1 calc R . .
C16 C 0.1975(2) 0.57217(18) 0.09602(12) 0.0249(3) Uani 1 1 d . . .
H16 H 0.0882 0.5179 0.1032 0.030 Uiso 1 1 calc R . .
C17 C 0.59833(17) 0.66791(15) 0.27585(11) 0.0170(3) Uani 1 1 d . . .
C18 C 0.4476(2) 0.81454(19) -0.13881(12) 0.0266(3) Uani 1 1 d . . .
H18A H 0.3990 0.7580 -0.2008 0.040 Uiso 1 1 calc R . .
H18B H 0.5848 0.8086 -0.1473 0.040 Uiso 1 1 calc R . .
H18C H 0.3910 0.9303 -0.1433 0.040 Uiso 1 1 calc R . .
C21 C -0.00497(17) 0.25896(15) 0.49465(11) 0.0156(3) Uani 1 1 d . . .
C22 C -0.32113(17) 0.18702(15) 0.49058(11) 0.0170(3) Uani 1 1 d . . .
C23 C -0.27828(17) 0.09719(16) 0.59843(11) 0.0179(3) Uani 1 1 d . . .
H23 H -0.3682 0.0350 0.6357 0.021 Uiso 1 1 calc R . .
C24 C -0.10939(18) 0.10014(15) 0.64824(11) 0.0169(3) Uani 1 1 d . . .
C25 C -0.06252(19) 0.01554(17) 0.76451(12) 0.0231(3) Uani 1 1 d . . .
H25A H -0.1663 -0.0443 0.7927 0.035 Uiso 1 1 calc R . .
H25B H -0.0436 0.0978 0.8187 0.035 Uiso 1 1 calc R . .
H25C H 0.0530 -0.0622 0.7583 0.035 Uiso 1 1 calc R . .


_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
O1 C1 1.2256(15) . ?
O11 C17 1.2254(16) . ?
O12 C17 1.3122(15) . ?
O12 H12O 0.94(2) . ?
O21 C22 1.2314(15) . ?
N1 C1 1.3523(16) . ?
N1 C11 1.4083(16) . ?
N1 H1N 0.877(19) . ?
N2 C21 1.3723(16) . ?
N2 C1 1.3956(16) . ?
N2 H2N 0.87(2) . ?
N21 C21 1.3475(16) . ?
N21 C22 1.3994(16) . ?
N21 H21N 0.881(18) . ?
N22 C21 1.3130(17) . ?
N22 C24 1.3833(16) . ?
C11 C16 1.3962(18) . ?
C11 C12 1.4126(17) . ?
C12 C13 1.3943(18) . ?
C12 C17 1.4882(17) . ?
C13 C14 1.3848(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3893(19) . ?
C14 C18 1.5027(18) . ?
C15 C16 1.3838(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22 C23 1.4258(18) . ?
C23 C24 1.3596(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.4982(18) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C17 O12 H12O 113.8(14) . . ?
C1 N1 C11 126.39(11) . . ?
C1 N1 H1N 117.9(12) . . ?
C11 N1 H1N 115.6(12) . . ?
C21 N2 C1 125.26(11) . . ?
C21 N2 H2N 116.2(14) . . ?
C1 N2 H2N 117.8(14) . . ?
C21 N21 C22 123.37(11) . . ?
C21 N21 H21N 116.2(11) . . ?
C22 N21 H21N 120.4(11) . . ?
C21 N22 C24 116.99(11) . . ?
O1 C1 N1 125.04(12) . . ?
O1 C1 N2 122.07(11) . . ?
N1 C1 N2 112.88(11) . . ?
C16 C11 N1 123.03(11) . . ?
C16 C11 C12 118.08(11) . . ?
N1 C11 C12 118.88(11) . . ?
C13 C12 C11 119.34(11) . . ?
C13 C12 C17 118.46(11) . . ?
C11 C12 C17 122.20(11) . . ?
C14 C13 C12 122.71(12) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C13 C14 C15 117.01(12) . . ?
C13 C14 C18 121.37(12) . . ?
C15 C14 C18 121.62(12) . . ?
C16 C15 C14 122.04(12) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 120.78(12) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O11 C17 O12 123.09(11) . . ?
O11 C17 C12 124.18(11) . . ?
O12 C17 C12 112.73(11) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N22 C21 N21 122.85(11) . . ?
N22 C21 N2 117.97(11) . . ?
N21 C21 N2 119.17(11) . . ?
O21 C22 N21 118.71(11) . . ?
O21 C22 C23 127.76(12) . . ?
N21 C22 C23 113.53(11) . . ?
C24 C23 C22 120.32(11) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 N22 122.81(12) . . ?
C23 C24 C25 122.15(11) . . ?
N22 C24 C25 115.04(11) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 O1 -3.3(2) . . . . ?
C11 N1 C1 N2 177.71(11) . . . . ?
C21 N2 C1 O1 -0.1(2) . . . . ?
C21 N2 C1 N1 178.95(11) . . . . ?
C1 N1 C11 C16 -10.4(2) . . . . ?
C1 N1 C11 C12 170.67(12) . . . . ?
C16 C11 C12 C13 -1.61(19) . . . . ?
N1 C11 C12 C13 177.37(11) . . . . ?
C16 C11 C12 C17 178.06(12) . . . . ?
N1 C11 C12 C17 -2.95(18) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C17 C12 C13 C14 -179.63(12) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C12 C13 C14 C18 -178.26(13) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C18 C14 C15 C16 178.37(14) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
N1 C11 C16 C15 -177.21(13) . . . . ?
C12 C11 C16 C15 1.7(2) . . . . ?
C13 C12 C17 O11 -165.25(12) . . . . ?
C11 C12 C17 O11 15.1(2) . . . . ?
C13 C12 C17 O12 15.66(17) . . . . ?
C11 C12 C17 O12 -164.02(12) . . . . ?
C24 N22 C21 N21 2.47(18) . . . . ?
C24 N22 C21 N2 -178.31(11) . . . . ?
C22 N21 C21 N22 -1.88(19) . . . . ?
C22 N21 C21 N2 178.91(11) . . . . ?
C1 N2 C21 N22 176.80(11) . . . . ?
C1 N2 C21 N21 -3.95(19) . . . . ?
C21 N21 C22 O21 178.39(12) . . . . ?
C21 N21 C22 C23 -1.11(17) . . . . ?
O21 C22 C23 C24 -176.09(13) . . . . ?
N21 C22 C23 C24 3.36(17) . . . . ?
C22 C23 C24 N22 -2.95(19) . . . . ?
C22 C23 C24 C25 176.47(12) . . . . ?
C21 N22 C24 C23 -0.06(18) . . . . ?
C21 N22 C24 C25 -179.51(11) . . . . ?

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
O12 H12O N22 0.94(2) 1.71(3) 2.6341(14) 169(2) 2_666
N1 H1N O11 0.877(19) 1.981(19) 2.6829(14) 136.2(16) .
N1 H1N O21 0.877(19) 2.536(18) 3.1307(15) 125.8(14) 1_655
N2 H2N O21 0.87(2) 2.19(2) 2.9033(14) 138.2(18) 1_655
N2 H2N O11 0.87(2) 2.44(2) 3.1507(14) 139.3(17) 2_666
N21 H21N O1 0.881(18) 1.909(17) 2.6058(14) 134.7(15) .
N21 H21N O11 0.881(18) 2.412(17) 2.9556(14) 120.2(13) 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050


#===END
_database_code_depnum_ccdc_archive 'CCDC 992565'
