# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
# 
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#  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.
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data_shelx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N4 O6'
_chemical_formula_sum            'C22 H18 N4 O6'
_chemical_formula_weight         434.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   10.393(3)
_cell_length_b                   26.134(7)
_cell_length_c                   7.767(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.958(13)
_cell_angle_gamma                90.00
_cell_volume                     1983.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1088
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      20.94

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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 CCD'
_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            15046
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_sigmaI/netI    0.1001
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.90
_reflns_number_total             3788
_reflns_number_gt                1850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0733P)²+0.3374P] 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     SHELXL
_refine_ls_extinction_coef       0.0058(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3788
_refine_ls_number_parameters     308
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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
C1 C 0.2541(3) 0.62343(11) 0.3828(4) 0.0401(8) Uani 1 1 d . . .
H1 H 0.3490 0.6237 0.4347 0.048 Uiso 1 1 calc R . .
C2 C 0.1831(3) 0.57964(11) 0.3975(4) 0.0392(8) Uani 1 1 d . . .
C3 C 0.0425(4) 0.57944(13) 0.3175(5) 0.0546(10) Uani 1 1 d . . .
H3 H -0.0072 0.5505 0.3259 0.066 Uiso 1 1 calc R . .
C4 C -0.0244(4) 0.62217(13) 0.2249(6) 0.0680(12) Uani 1 1 d . . .
H4 H -0.1192 0.6218 0.1703 0.082 Uiso 1 1 calc R . .
C5 C 0.0482(4) 0.66547(13) 0.2128(5) 0.0586(11) Uani 1 1 d . . .
H5 H 0.0019 0.6939 0.1495 0.070 Uiso 1 1 calc R . .
C6 C 0.1877(3) 0.66682(11) 0.2932(5) 0.0398(8) Uani 1 1 d . . .
C7 C 0.2519(3) 0.53236(11) 0.4926(5) 0.0407(8) Uani 1 1 d . . .
C8 C 0.5676(4) 0.50715(12) 0.8234(5) 0.0456(9) Uani 1 1 d . . .
H8 H 0.5981 0.5409 0.8378 0.055 Uiso 1 1 calc R . .
C9 C 0.6551(3) 0.46768(12) 0.9343(4) 0.0413(8) Uani 1 1 d . . .
C10 C 0.6111(3) 0.41768(12) 0.9364(5) 0.0436(9) Uani 1 1 d . . .
C11 C 0.6961(4) 0.38213(12) 1.0560(5) 0.0458(9) Uani 1 1 d . . .
C12 C 0.8256(4) 0.39558(14) 1.1608(5) 0.0561(10) Uani 1 1 d . . .
H12 H 0.8833 0.3715 1.2372 0.067 Uiso 1 1 calc R . .
C13 C 0.8720(4) 0.44497(15) 1.1543(6) 0.0692(12) Uani 1 1 d . . .
H13 H 0.9611 0.4539 1.2248 0.083 Uiso 1 1 calc R . .
C14 C 0.7866(4) 0.48049(14) 1.0442(5) 0.0585(11) Uani 1 1 d . . .
H14 H 0.8174 0.5139 1.0431 0.070 Uiso 1 1 calc R . .
C15 C 0.2611(3) 0.71498(12) 0.2840(5) 0.0430(8) Uani 1 1 d . . .
C16 C 0.5801(4) 0.74116(12) 0.2566(5) 0.0482(9) Uani 1 1 d . . .
H16 H 0.6098 0.7074 0.2696 0.058 Uiso 1 1 calc R . .
C17 C 0.6664(3) 0.78009(12) 0.2196(5) 0.0435(8) Uani 1 1 d . . .
C18 C 0.6293(3) 0.83176(12) 0.1949(4) 0.0401(8) Uani 1 1 d . . .
C19 C 0.7068(4) 0.86608(12) 0.1341(5) 0.0440(9) Uani 1 1 d . . .
C20 C 0.8241(4) 0.85030(13) 0.1095(5) 0.0557(10) Uani 1 1 d . . .
H20 H 0.8754 0.8733 0.0682 0.067 Uiso 1 1 calc R . .
C21 C 0.8674(4) 0.80012(14) 0.1458(6) 0.0656(12) Uani 1 1 d . . .
H21 H 0.9503 0.7899 0.1357 0.079 Uiso 1 1 calc R . .
C22 C 0.7882(4) 0.76567(13) 0.1963(6) 0.0604(11) Uani 1 1 d . . .
H22 H 0.8164 0.7317 0.2156 0.072 Uiso 1 1 calc R . .
N1 N 0.3788(3) 0.53883(10) 0.6130(4) 0.0449(7) Uani 1 1 d D . .
H1B H 0.414(3) 0.5719(8) 0.644(4) 0.054 Uiso 1 1 d D . .
N2 N 0.4500(3) 0.49715(10) 0.7068(4) 0.0438(7) Uani 1 1 d . . .
N3 N 0.3930(3) 0.70955(10) 0.2970(4) 0.0453(7) Uani 1 1 d D . .
H3B H 0.419(3) 0.6769(8) 0.263(4) 0.054 Uiso 1 1 d D . .
N4 N 0.4659(3) 0.75153(9) 0.2719(4) 0.0443(7) Uani 1 1 d . . .
O1 O 0.1951(2) 0.49035(8) 0.4637(4) 0.0558(7) Uani 1 1 d . . .
O2 O 0.4873(3) 0.40037(9) 0.8269(4) 0.0663(8) Uani 1 1 d D . .
H2A H 0.447(4) 0.4240(11) 0.759(5) 0.080 Uiso 1 1 d D . .
O3 O 0.6423(3) 0.33429(9) 1.0558(4) 0.0600(7) Uani 1 1 d D . .
H3A H 0.705(3) 0.3150(12) 1.121(4) 0.072 Uiso 1 1 d D . .
O4 O 0.2037(2) 0.75689(8) 0.2664(4) 0.0633(8) Uani 1 1 d . . .
O5 O 0.5175(3) 0.85143(9) 0.2234(4) 0.0541(7) Uani 1 1 d D . .
H5A H 0.477(3) 0.8290(11) 0.262(5) 0.065 Uiso 1 1 d D . .
O6 O 0.6552(3) 0.91438(9) 0.0992(4) 0.0628(8) Uani 1 1 d D . .
H6A H 0.709(3) 0.9331(13) 0.067(5) 0.075 Uiso 1 1 d D . .


_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
C1 C6 1.385(4) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(4) . ?
C2 C7 1.491(4) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 C15 1.486(4) . ?
C7 O1 1.230(3) . ?
C7 N1 1.342(4) . ?
C8 N2 1.275(4) . ?
C8 C9 1.449(4) . ?
C8 H8 0.9300 . ?
C9 C14 1.383(5) . ?
C9 C10 1.386(4) . ?
C10 O2 1.355(4) . ?
C10 C11 1.395(5) . ?
C11 C12 1.360(5) . ?
C11 O3 1.369(4) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O4 1.232(4) . ?
C15 N3 1.348(4) . ?
C16 N4 1.262(4) . ?
C16 C17 1.449(4) . ?
C16 H16 0.9300 . ?
C17 C22 1.391(5) . ?
C17 C18 1.400(4) . ?
C18 O5 1.356(4) . ?
C18 C19 1.391(4) . ?
C19 C20 1.361(5) . ?
C19 O6 1.362(4) . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 N2 1.377(4) . ?
N1 H1B 0.937(18) . ?
N3 N4 1.384(3) . ?
N3 H3B 0.958(18) . ?
O2 H2A 0.826(18) . ?
O3 H3A 0.846(18) . ?
O5 H5A 0.836(18) . ?
O6 H6A 0.843(18) . ?

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 C1 C2 121.9(3) . . ?
C6 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C7 118.4(3) . . ?
C1 C2 C7 123.0(3) . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C15 118.8(3) . . ?
C1 C6 C15 122.8(3) . . ?
O1 C7 N1 122.4(3) . . ?
O1 C7 C2 122.0(3) . . ?
N1 C7 C2 115.6(3) . . ?
N2 C8 C9 122.1(3) . . ?
N2 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 118.8(3) . . ?
C10 C9 C8 122.4(3) . . ?
O2 C10 C9 123.6(3) . . ?
O2 C10 C11 116.4(3) . . ?
C9 C10 C11 119.9(3) . . ?
C12 C11 O3 123.8(3) . . ?
C12 C11 C10 119.9(3) . . ?
O3 C11 C10 116.2(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O4 C15 N3 122.9(3) . . ?
O4 C15 C6 121.4(3) . . ?
N3 C15 C6 115.7(3) . . ?
N4 C16 C17 122.3(3) . . ?
N4 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C22 C17 C18 117.6(3) . . ?
C22 C17 C16 119.3(3) . . ?
C18 C17 C16 123.0(3) . . ?
O5 C18 C19 116.0(3) . . ?
O5 C18 C17 123.7(3) . . ?
C19 C18 C17 120.3(3) . . ?
C20 C19 O6 124.3(3) . . ?
C20 C19 C18 120.2(3) . . ?
O6 C19 C18 115.5(3) . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.6(3) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
C7 N1 N2 119.5(3) . . ?
C7 N1 H1B 120(2) . . ?
N2 N1 H1B 120(2) . . ?
C8 N2 N1 115.2(3) . . ?
C15 N3 N4 119.8(3) . . ?
C15 N3 H3B 116.5(19) . . ?
N4 N3 H3B 116.7(19) . . ?
C16 N4 N3 114.8(3) . . ?
C10 O2 H2A 108(3) . . ?
C11 O3 H3A 108(3) . . ?
C18 O5 H5A 111(3) . . ?
C19 O6 H6A 110(3) . . ?

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
C6 C1 C2 C3 1.1(5) . . . . ?
C6 C1 C2 C7 179.8(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C7 C2 C3 C4 -178.6(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
C4 C5 C6 C15 -177.2(3) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C2 C1 C6 C15 176.8(3) . . . . ?
C3 C2 C7 O1 18.8(5) . . . . ?
C1 C2 C7 O1 -159.9(3) . . . . ?
C3 C2 C7 N1 -160.4(3) . . . . ?
C1 C2 C7 N1 20.9(5) . . . . ?
N2 C8 C9 C14 173.5(4) . . . . ?
N2 C8 C9 C10 -7.6(5) . . . . ?
C14 C9 C10 O2 -176.2(3) . . . . ?
C8 C9 C10 O2 4.9(5) . . . . ?
C14 C9 C10 C11 3.7(5) . . . . ?
C8 C9 C10 C11 -175.2(3) . . . . ?
O2 C10 C11 C12 175.3(3) . . . . ?
C9 C10 C11 C12 -4.7(5) . . . . ?
O2 C10 C11 O3 -3.1(5) . . . . ?
C9 C10 C11 O3 176.9(3) . . . . ?
O3 C11 C12 C13 -179.4(3) . . . . ?
C10 C11 C12 C13 2.3(6) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C9 -1.9(6) . . . . ?
C10 C9 C14 C13 -0.5(6) . . . . ?
C8 C9 C14 C13 178.5(4) . . . . ?
C5 C6 C15 O4 25.5(5) . . . . ?
C1 C6 C15 O4 -153.2(3) . . . . ?
C5 C6 C15 N3 -154.8(3) . . . . ?
C1 C6 C15 N3 26.5(5) . . . . ?
N4 C16 C17 C22 -177.1(3) . . . . ?
N4 C16 C17 C18 -1.2(6) . . . . ?
C22 C17 C18 O5 -176.1(3) . . . . ?
C16 C17 C18 O5 7.8(5) . . . . ?
C22 C17 C18 C19 5.2(5) . . . . ?
C16 C17 C18 C19 -170.8(3) . . . . ?
O5 C18 C19 C20 177.1(3) . . . . ?
C17 C18 C19 C20 -4.2(5) . . . . ?
O5 C18 C19 O6 -4.3(5) . . . . ?
C17 C18 C19 O6 174.4(3) . . . . ?
O6 C19 C20 C21 -178.9(4) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C19 C20 C21 C22 3.7(6) . . . . ?
C20 C21 C22 C17 -2.6(6) . . . . ?
C18 C17 C22 C21 -1.9(6) . . . . ?
C16 C17 C22 C21 174.3(4) . . . . ?
O1 C7 N1 N2 0.9(5) . . . . ?
C2 C7 N1 N2 -179.9(3) . . . . ?
C9 C8 N2 N1 179.6(3) . . . . ?
C7 N1 N2 C8 -177.4(3) . . . . ?
O4 C15 N3 N4 -6.6(5) . . . . ?
C6 C15 N3 N4 173.6(3) . . . . ?
C17 C16 N4 N3 176.6(3) . . . . ?
C15 N3 N4 C16 -168.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.90
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 995844'
