# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Gale, Philip'
'Hiscock, Jennifer'
'Lalaoui, Noemie'
'Light, Mark'
'Wells, Neil'
'Wenzel, Marco'

_publ_contact_author_name        'Gale, Philip'
_publ_contact_author_email       philip.gale@soton.ac.uk

_publ_section_title              
;
Benzimidazole-based anion receptors: tautomeric switching and selectivity
;

# Attachment '- 0101_1111_1112_1118_combined.cif'

data_2011jh0101
_database_code_depnum_ccdc_archive 'CCDC 851118'
#TrackingRef '- 0101_1111_1112_1118_combined.cif'

_chemical_compound_source        ?

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N6 O2'
_chemical_formula_weight         352.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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   P2(1)/c
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                   7.2914(2)
_cell_length_b                   13.7723(3)
_cell_length_c                   17.2777(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.684(2)
_cell_angle_gamma                90.00
_cell_volume                     1710.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18063
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18453
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3025
_reflns_number_gt                2630
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_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^ > 2\s(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 hydrogen bonded methanol is disordered either side of an inversion
centre; each component is modelled as 50% occupied.
;

_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^)+(0.0634P)^2^+0.9790P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3025
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.74080(19) 0.37098(9) 0.42118(7) 0.0334(3) Uani 1 1 d . . .
N1 N 0.46978(19) 0.12531(10) 0.11767(8) 0.0233(3) Uani 1 1 d . . .
N2 N 0.58430(19) 0.08685(10) 0.24283(8) 0.0246(3) Uani 1 1 d . . .
N3 N 0.77632(19) 0.22727(10) 0.35934(8) 0.0246(3) Uani 1 1 d . . .
H93 H 0.8127 0.1665 0.3666 0.030 Uiso 1 1 calc R . .
N4 N 0.8927(2) 0.24434(11) 0.49029(8) 0.0258(3) Uani 1 1 d . . .
H94 H 0.9229 0.1828 0.4867 0.031 Uiso 1 1 calc R . .
N5 N 1.07513(19) 0.13123(10) 0.62627(8) 0.0246(3) Uani 1 1 d . . .
N6 N 1.17447(19) 0.19379(10) 0.74565(8) 0.0243(3) Uani 1 1 d . . .
C1 C 0.3855(2) 0.11278(13) 0.03600(10) 0.0281(4) Uani 1 1 d . . .
H1A H 0.3332 0.0473 0.0283 0.042 Uiso 1 1 calc R . .
H1B H 0.4801 0.1219 0.0025 0.042 Uiso 1 1 calc R . .
H1C H 0.2862 0.1608 0.0221 0.042 Uiso 1 1 calc R . .
C2 C 0.4989(2) 0.05586(12) 0.17414(10) 0.0249(4) Uani 1 1 d . . .
H2 H 0.4608 -0.0097 0.1648 0.030 Uiso 1 1 calc R . .
C3 C 0.5417(2) 0.21032(12) 0.15239(10) 0.0211(4) Uani 1 1 d . . .
C4 C 0.5483(2) 0.30424(13) 0.12348(10) 0.0262(4) Uani 1 1 d . . .
H4 H 0.4984 0.3203 0.0706 0.031 Uiso 1 1 calc R . .
C5 C 0.6314(2) 0.37266(12) 0.17610(11) 0.0271(4) Uani 1 1 d . . .
H5 H 0.6372 0.4380 0.1591 0.033 Uiso 1 1 calc R . .
C6 C 0.7076(2) 0.34940(12) 0.25366(10) 0.0246(4) Uani 1 1 d . . .
H6 H 0.7665 0.3988 0.2874 0.030 Uiso 1 1 calc R . .
C7 C 0.6991(2) 0.25592(12) 0.28234(10) 0.0215(4) Uani 1 1 d . . .
C8 C 0.6128(2) 0.18504(12) 0.23008(10) 0.0208(4) Uani 1 1 d . . .
C9 C 0.7989(2) 0.28711(12) 0.42361(10) 0.0237(4) Uani 1 1 d . . .
C10 C 0.9457(2) 0.28886(12) 0.56387(10) 0.0226(4) Uani 1 1 d . . .
C11 C 0.9252(2) 0.38674(12) 0.58032(10) 0.0245(4) Uani 1 1 d . . .
H11 H 0.8675 0.4288 0.5399 0.029 Uiso 1 1 calc R . .
C12 C 0.9882(2) 0.42444(13) 0.65546(10) 0.0262(4) Uani 1 1 d . . .
H12 H 0.9718 0.4917 0.6642 0.031 Uiso 1 1 calc R . .
C13 C 1.0728(2) 0.36793(12) 0.71726(10) 0.0246(4) Uani 1 1 d . . .
H13 H 1.1137 0.3940 0.7682 0.029 Uiso 1 1 calc R . .
C14 C 1.0944(2) 0.27026(12) 0.70007(10) 0.0223(4) Uani 1 1 d . . .
C15 C 1.0330(2) 0.23000(12) 0.62572(10) 0.0210(4) Uani 1 1 d . . .
C16 C 1.1589(2) 0.11435(13) 0.69849(10) 0.0256(4) Uani 1 1 d . . .
H16 H 1.2046 0.0522 0.7161 0.031 Uiso 1 1 calc R . .
C17 C 1.2546(2) 0.19874(14) 0.82838(10) 0.0299(4) Uani 1 1 d . . .
H17A H 1.1569 0.2142 0.8590 0.045 Uiso 1 1 calc R . .
H17B H 1.3504 0.2494 0.8365 0.045 Uiso 1 1 calc R . .
H17C H 1.3107 0.1360 0.8455 0.045 Uiso 1 1 calc R . .
O2A O 0.9856(4) -0.06041(17) 0.57516(15) 0.0303(6) Uani 0.50 1 d P A 1
H2A H 1.0111 -0.0036 0.5911 0.045 Uiso 0.50 1 calc PR A 1
C18A C 0.7932(5) -0.0687(3) 0.5496(2) 0.0364(9) Uani 0.50 1 d P A 1
H18A H 0.7325 -0.0866 0.5940 0.055 Uiso 0.50 1 calc PR A 1
H18B H 0.7689 -0.1188 0.5089 0.055 Uiso 0.50 1 calc PR A 1
H18C H 0.7437 -0.0064 0.5280 0.055 Uiso 0.50 1 calc PR A 1
O2B O 1.1366(4) -0.04720(18) 0.56166(16) 0.0354(6) Uani 0.50 1 d P B 2
H2B H 1.0817 0.0040 0.5711 0.053 Uiso 0.50 1 calc PR B 2
C18B C 1.2952(6) -0.0234(3) 0.5285(3) 0.0491(11) Uani 0.50 1 d P B 2
H18D H 1.2710 0.0360 0.4972 0.074 Uiso 0.50 1 calc PR B 2
H18E H 1.3230 -0.0767 0.4947 0.074 Uiso 0.50 1 calc PR B 2
H18F H 1.4017 -0.0130 0.5705 0.074 Uiso 0.50 1 calc PR B 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
O1 0.0440(8) 0.0253(7) 0.0289(7) -0.0013(5) 0.0005(6) 0.0140(6)
N1 0.0206(7) 0.0236(8) 0.0255(8) -0.0018(6) 0.0030(6) -0.0001(6)
N2 0.0240(7) 0.0194(7) 0.0294(8) 0.0020(6) 0.0021(6) -0.0016(6)
N3 0.0289(7) 0.0176(7) 0.0253(8) 0.0006(6) -0.0014(6) 0.0034(6)
N4 0.0326(8) 0.0192(7) 0.0237(8) -0.0022(6) -0.0013(6) 0.0056(6)
N5 0.0252(7) 0.0214(7) 0.0267(8) -0.0005(6) 0.0027(6) 0.0035(6)
N6 0.0235(7) 0.0251(8) 0.0235(8) 0.0011(6) 0.0022(6) 0.0027(6)
C1 0.0275(9) 0.0319(10) 0.0238(9) -0.0051(7) 0.0012(7) -0.0013(7)
C2 0.0240(8) 0.0201(9) 0.0305(9) -0.0008(7) 0.0036(7) -0.0020(7)
C3 0.0171(7) 0.0215(9) 0.0250(9) -0.0011(7) 0.0046(6) 0.0017(6)
C4 0.0276(9) 0.0278(9) 0.0235(9) 0.0040(7) 0.0052(7) 0.0040(7)
C5 0.0324(9) 0.0190(9) 0.0316(10) 0.0044(7) 0.0103(7) 0.0016(7)
C6 0.0252(8) 0.0201(8) 0.0290(9) -0.0029(7) 0.0061(7) 0.0000(7)
C7 0.0177(8) 0.0224(9) 0.0244(9) -0.0004(7) 0.0039(6) 0.0030(6)
C8 0.0184(8) 0.0188(8) 0.0256(9) 0.0016(7) 0.0047(6) 0.0016(6)
C9 0.0225(8) 0.0235(9) 0.0245(9) 0.0003(7) 0.0021(7) 0.0020(7)
C10 0.0190(8) 0.0235(9) 0.0249(9) -0.0009(7) 0.0024(6) 0.0008(7)
C11 0.0235(8) 0.0204(9) 0.0293(9) 0.0021(7) 0.0033(7) 0.0016(7)
C12 0.0237(9) 0.0205(9) 0.0344(10) -0.0038(7) 0.0051(7) -0.0012(7)
C13 0.0232(8) 0.0253(9) 0.0254(9) -0.0054(7) 0.0047(7) -0.0042(7)
C14 0.0170(8) 0.0256(9) 0.0244(9) 0.0023(7) 0.0032(6) 0.0004(6)
C15 0.0185(8) 0.0192(8) 0.0251(9) -0.0010(7) 0.0035(6) 0.0008(6)
C16 0.0251(9) 0.0230(9) 0.0282(10) 0.0004(7) 0.0029(7) 0.0041(7)
C17 0.0282(9) 0.0366(10) 0.0237(9) 0.0010(8) 0.0012(7) 0.0040(8)
O2A 0.0381(15) 0.0171(12) 0.0322(14) -0.0026(10) -0.0041(11) 0.0021(11)
C18A 0.040(2) 0.039(2) 0.029(2) -0.0085(17) 0.0059(16) -0.0014(17)
O2B 0.0426(17) 0.0233(14) 0.0381(15) -0.0026(11) 0.0006(12) 0.0046(12)
C18B 0.041(2) 0.041(2) 0.069(3) -0.017(2) 0.019(2) -0.0030(19)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.229(2) . ?
N1 C2 1.357(2) . ?
N1 C3 1.378(2) . ?
N1 C1 1.452(2) . ?
N2 C2 1.315(2) . ?
N2 C8 1.391(2) . ?
N3 C9 1.370(2) . ?
N3 C7 1.411(2) . ?
N4 C9 1.370(2) . ?
N4 C10 1.406(2) . ?
N5 C16 1.315(2) . ?
N5 C15 1.394(2) . ?
N6 C16 1.357(2) . ?
N6 C14 1.384(2) . ?
N6 C17 1.452(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.377(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.385(2) . ?
C7 C8 1.405(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.405(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.380(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.402(2) . ?
O2A C18A 1.403(5) . ?
O2B C18B 1.413(5) . ?

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 C3 106.49(14) . . ?
C2 N1 C1 127.19(14) . . ?
C3 N1 C1 126.29(15) . . ?
C2 N2 C8 103.48(14) . . ?
C9 N3 C7 124.77(14) . . ?
C9 N4 C10 126.54(15) . . ?
C16 N5 C15 104.22(14) . . ?
C16 N6 C14 106.69(14) . . ?
C16 N6 C17 127.44(15) . . ?
C14 N6 C17 125.86(15) . . ?
N2 C2 N1 114.39(15) . . ?
N1 C3 C4 131.88(16) . . ?
N1 C3 C8 104.97(14) . . ?
C4 C3 C8 123.14(16) . . ?
C5 C4 C3 115.93(16) . . ?
C4 C5 C6 122.39(16) . . ?
C7 C6 C5 121.41(16) . . ?
C6 C7 C8 117.28(15) . . ?
C6 C7 N3 124.24(15) . . ?
C8 C7 N3 118.45(15) . . ?
N2 C8 C3 110.66(14) . . ?
N2 C8 C7 129.52(15) . . ?
C3 C8 C7 119.82(15) . . ?
O1 C9 N4 123.60(15) . . ?
O1 C9 N3 122.96(15) . . ?
N4 C9 N3 113.44(14) . . ?
C11 C10 C15 117.01(15) . . ?
C11 C10 N4 125.79(15) . . ?
C15 C10 N4 117.16(15) . . ?
C10 C11 C12 121.23(16) . . ?
C13 C12 C11 122.80(16) . . ?
C12 C13 C14 115.57(16) . . ?
N6 C14 C13 131.75(16) . . ?
N6 C14 C15 105.04(14) . . ?
C13 C14 C15 123.21(16) . . ?
N5 C15 C14 110.11(14) . . ?
N5 C15 C10 129.71(15) . . ?
C14 C15 C10 120.17(15) . . ?
N5 C16 N6 113.94(15) . . ?

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
N3 H93 O2B 0.88 2.05 2.850(3) 150.0 3_756
N3 H93 O2A 0.88 2.19 2.986(3) 149.5 3_756
N4 H94 O2B 0.88 2.06 2.856(3) 149.6 3_756
N4 H94 O2A 0.88 2.16 2.970(3) 152.6 3_756
O2A H2A N5 0.84 1.98 2.825(3) 178.5 .
O2B H2B N5 0.84 2.00 2.767(3) 151.5 .
C16 H16 N2 0.95 2.48 3.402(2) 162.3 3_756

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

#===END

data_2011jh1111
#TrackingRef '- 0101_1111_1112_1118_combined.cif'

_database_code_depnum_ccdc_archive 'CCDC 851119'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C14 H7 F5 N4 O, C7 H5 O2, H2 O'
_chemical_formula_sum            'C37 H50 F5 N5 O4'
_chemical_formula_weight         723.82

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'
F F 0.0171 0.0103 '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

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                   21.464(15)
_cell_length_b                   8.350(6)
_cell_length_c                   20.873(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.375(12)
_cell_angle_gamma                90.00
_cell_volume                     3701(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9724
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      31.4

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_source_current           24.00
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   RA
_diffrn_radiation_monochromator  'Varimax mirror'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 4 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_reflns_number            24627
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.1040
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6506
_reflns_number_gt                5260
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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^ > 2\s(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.

One arm of the TBA was modelled as disordered over two positions for the
terminal methyl group, mild distance restraints and thermal parameter
constraints were applied. All hydrogens were visible in the difference
map; CH, CH2 and CH3 hydrogens were placed in idealised positions and
refined using a riding model, NH hydrogens were freely refined with thermal
parameters fixed as 1.2 times the parent atom. The hydrogen atoms of the
water were refined with thermal parameters fixed at 1.2 times that of the
oxygen and mild distance restraints were applied to the O-H and H...H
distances.

;

_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^)+(0.0182P)^2^+8.0790P] 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         6506
_refine_ls_number_parameters     487
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1173
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.269
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
F1 F -0.10162(13) 0.5168(4) 0.25432(14) 0.0369(8) Uani 1 1 d . . .
F2 F 0.00902(12) 0.5396(4) 0.33507(13) 0.0379(8) Uani 1 1 d . . .
F3 F 0.05786(13) 0.8326(4) 0.37235(14) 0.0439(9) Uani 1 1 d . . .
F4 F -0.00690(14) 1.1053(4) 0.33070(15) 0.0433(9) Uani 1 1 d . . .
F5 F -0.11910(13) 1.0836(4) 0.25234(15) 0.0420(8) Uani 1 1 d . . .
O1 O -0.22528(14) 0.6570(4) 0.27988(15) 0.0295(9) Uani 1 1 d . . .
N1 N -0.17136(18) 0.7923(5) 0.20865(19) 0.0261(10) Uani 1 1 d . . .
H1 H -0.173(2) 0.853(6) 0.173(2) 0.031 Uiso 1 1 d . . .
N2 N -0.27756(17) 0.7551(5) 0.18198(18) 0.0219(9) Uani 1 1 d . . .
H2 H -0.269(2) 0.814(6) 0.144(2) 0.026 Uiso 1 1 d . . .
N3 N -0.38242(18) 0.9107(5) 0.0924(2) 0.0252(10) Uani 1 1 d . . .
H3 H -0.348(2) 0.919(6) 0.072(2) 0.030 Uiso 1 1 d . . .
N4 N -0.48551(18) 0.9155(5) 0.1053(2) 0.0316(11) Uani 1 1 d . . .
C1 C -0.0801(2) 0.6630(7) 0.2749(2) 0.0291(12) Uani 1 1 d . . .
C2 C -0.0236(2) 0.6744(7) 0.3154(2) 0.0290(12) Uani 1 1 d . . .
C3 C 0.0015(2) 0.8222(7) 0.3334(2) 0.0287(12) Uani 1 1 d . . .
C4 C -0.0310(2) 0.9600(7) 0.3124(2) 0.0298(12) Uani 1 1 d . . .
C5 C -0.0881(2) 0.9463(7) 0.2727(2) 0.0305(13) Uani 1 1 d . . .
C6 C -0.1140(2) 0.7989(7) 0.2522(2) 0.0269(12) Uani 1 1 d . . .
C7 C -0.2256(2) 0.7264(6) 0.2281(2) 0.0252(12) Uani 1 1 d . . .
C8 C -0.3418(2) 0.7389(6) 0.1916(2) 0.0212(11) Uani 1 1 d . . .
C9 C -0.3873(2) 0.8189(6) 0.1471(2) 0.0234(11) Uani 1 1 d . . .
C10 C -0.4419(2) 0.9614(6) 0.0697(2) 0.0298(12) Uani 1 1 d . . .
H10 H -0.4515 1.0244 0.0317 0.036 Uiso 1 1 calc R . .
C11 C -0.4515(2) 0.8228(6) 0.1546(2) 0.0262(12) Uani 1 1 d . . .
C12 C -0.4730(2) 0.7451(6) 0.2069(3) 0.0322(13) Uani 1 1 d . . .
H12 H -0.5158 0.7504 0.2135 0.039 Uiso 1 1 calc R . .
C13 C -0.4284(2) 0.6599(7) 0.2485(2) 0.0307(12) Uani 1 1 d . . .
H13 H -0.4419 0.6013 0.2830 0.037 Uiso 1 1 calc R . .
O2 O -0.29691(14) 0.5370(4) 0.50737(15) 0.0290(8) Uani 1 1 d . . .
O3 O -0.22450(15) 0.5487(5) 0.59577(16) 0.0356(9) Uani 1 1 d . . .
C14 C -0.3635(2) 0.6564(6) 0.2418(2) 0.0266(12) Uani 1 1 d . . .
H14 H -0.3348 0.5975 0.2718 0.032 Uiso 1 1 calc R . .
C15 C -0.2408(2) 0.5236(6) 0.5361(2) 0.0252(11) Uani 1 1 d . . .
C16 C -0.1901(2) 0.4724(6) 0.4957(2) 0.0223(11) Uani 1 1 d . . .
C17 C -0.2025(2) 0.4651(6) 0.4285(2) 0.0264(12) Uani 1 1 d . . .
H17 H -0.2434 0.4900 0.4071 0.032 Uiso 1 1 calc R . .
C18 C -0.1556(2) 0.4217(6) 0.3923(2) 0.0287(12) Uani 1 1 d . . .
H18 H -0.1647 0.4164 0.3464 0.034 Uiso 1 1 calc R . .
C19 C -0.0951(2) 0.3859(6) 0.4235(3) 0.0349(13) Uani 1 1 d . . .
H19 H -0.0630 0.3566 0.3988 0.042 Uiso 1 1 calc R . .
C20 C -0.0819(2) 0.3933(6) 0.4907(3) 0.0346(13) Uani 1 1 d . . .
H20 H -0.0408 0.3687 0.5119 0.042 Uiso 1 1 calc R . .
C21 C -0.1290(2) 0.4370(6) 0.5274(2) 0.0295(12) Uani 1 1 d . . .
H21 H -0.1199 0.4427 0.5732 0.035 Uiso 1 1 calc R . .
N5 N 0.28983(17) 0.4917(5) 0.07400(18) 0.0212(9) Uani 1 1 d . . .
C22 C 0.2306(2) 0.3857(6) 0.0680(2) 0.0223(11) Uani 1 1 d . B .
H22A H 0.2308 0.3135 0.0304 0.027 Uiso 1 1 calc R . .
H22B H 0.2331 0.3179 0.1072 0.027 Uiso 1 1 calc R . .
C23 C 0.1678(2) 0.4768(6) 0.0598(3) 0.0369(14) Uani 1 1 d D . .
H23A H 0.1647 0.5414 0.0989 0.044 Uiso 1 1 calc R A 1
H23B H 0.1653 0.5501 0.0222 0.044 Uiso 1 1 calc R A 1
C24A C 0.1142(8) 0.356(3) 0.0491(12) 0.028(2) Uani 0.480(7) 1 d PD B 1
H24A H 0.1118 0.2981 0.0901 0.034 Uiso 0.480(7) 1 calc PR B 1
H24B H 0.1229 0.2763 0.0164 0.034 Uiso 0.480(7) 1 calc PR B 1
C25A C 0.0507(4) 0.4384(12) 0.0262(5) 0.0281(17) Uani 0.480(7) 1 d PD B 1
H25A H 0.0430 0.5208 0.0575 0.042 Uiso 0.480(7) 1 calc PR B 1
H25B H 0.0168 0.3588 0.0225 0.042 Uiso 0.480(7) 1 calc PR B 1
H25C H 0.0519 0.4883 -0.0162 0.042 Uiso 0.480(7) 1 calc PR B 1
C24B C 0.1103(8) 0.371(3) 0.0415(10) 0.028(2) Uani 0.520(7) 1 d PD B 2
H24C H 0.0727 0.4232 0.0546 0.034 Uiso 0.520(7) 1 calc PR B 2
H24D H 0.1166 0.2669 0.0642 0.034 Uiso 0.520(7) 1 calc PR B 2
C25B C 0.1004(4) 0.3447(12) -0.0317(4) 0.0281(17) Uani 0.520(7) 1 d PD B 2
H25D H 0.0929 0.4479 -0.0538 0.042 Uiso 0.520(7) 1 calc PR B 2
H25E H 0.0640 0.2746 -0.0438 0.042 Uiso 0.520(7) 1 calc PR B 2
H25F H 0.1381 0.2946 -0.0444 0.042 Uiso 0.520(7) 1 calc PR B 2
C26 C 0.2915(2) 0.6092(6) 0.1302(2) 0.0231(11) Uani 1 1 d . . .
H26A H 0.2574 0.6886 0.1191 0.028 Uiso 1 1 calc R . .
H26B H 0.3320 0.6678 0.1350 0.028 Uiso 1 1 calc R . .
C27 C 0.2842(2) 0.5334(6) 0.1957(2) 0.0252(11) Uani 1 1 d . . .
H27A H 0.3137 0.4423 0.2044 0.030 Uiso 1 1 calc R . .
H27B H 0.2408 0.4920 0.1943 0.030 Uiso 1 1 calc R . .
C28 C 0.2979(2) 0.6582(6) 0.2506(2) 0.0252(11) Uani 1 1 d . . .
H28A H 0.2717 0.7544 0.2389 0.030 Uiso 1 1 calc R . .
H28B H 0.2856 0.6130 0.2907 0.030 Uiso 1 1 calc R . .
C29 C 0.3672(2) 0.7082(7) 0.2636(2) 0.0313(13) Uani 1 1 d . . .
H29A H 0.3938 0.6124 0.2694 0.047 Uiso 1 1 calc R . .
H29B H 0.3745 0.7737 0.3029 0.047 Uiso 1 1 calc R . .
H29C H 0.3777 0.7704 0.2268 0.047 Uiso 1 1 calc R . .
C30 C 0.3464(2) 0.3768(6) 0.0837(2) 0.0231(11) Uani 1 1 d . . .
H30A H 0.3436 0.3100 0.1223 0.028 Uiso 1 1 calc R . .
H30B H 0.3433 0.3041 0.0458 0.028 Uiso 1 1 calc R . .
C31 C 0.4112(2) 0.4574(6) 0.0921(2) 0.0254(11) Uani 1 1 d . . .
H31A H 0.4213 0.4999 0.1367 0.030 Uiso 1 1 calc R . .
H31B H 0.4106 0.5483 0.0616 0.030 Uiso 1 1 calc R . .
C32 C 0.4617(2) 0.3363(6) 0.0793(2) 0.0272(12) Uani 1 1 d . . .
H32A H 0.4510 0.2937 0.0348 0.033 Uiso 1 1 calc R . .
H32B H 0.4617 0.2455 0.1098 0.033 Uiso 1 1 calc R . .
C33 C 0.5282(2) 0.4114(6) 0.0871(2) 0.0312(13) Uani 1 1 d . . .
H33A H 0.5276 0.5066 0.0596 0.047 Uiso 1 1 calc R . .
H33B H 0.5581 0.3333 0.0743 0.047 Uiso 1 1 calc R . .
H33C H 0.5411 0.4418 0.1325 0.047 Uiso 1 1 calc R . .
C34 C 0.2907(2) 0.5927(6) 0.0134(2) 0.0226(11) Uani 1 1 d . . .
H34A H 0.3253 0.6714 0.0223 0.027 Uiso 1 1 calc R . .
H34B H 0.2508 0.6538 0.0054 0.027 Uiso 1 1 calc R . .
C35 C 0.2987(2) 0.5035(6) -0.0489(2) 0.0223(11) Uani 1 1 d . . .
H35A H 0.2715 0.4071 -0.0532 0.027 Uiso 1 1 calc R . .
H35B H 0.3429 0.4683 -0.0469 0.027 Uiso 1 1 calc R . .
C36 C 0.2809(2) 0.6122(6) -0.1079(2) 0.0254(12) Uani 1 1 d . . .
H36A H 0.2987 0.5669 -0.1452 0.031 Uiso 1 1 calc R . .
H36B H 0.3000 0.7191 -0.0984 0.031 Uiso 1 1 calc R . .
C37 C 0.2092(2) 0.6319(6) -0.1269(2) 0.0291(12) Uani 1 1 d . . .
H37A H 0.1900 0.5269 -0.1374 0.044 Uiso 1 1 calc R . .
H37B H 0.2006 0.7025 -0.1646 0.044 Uiso 1 1 calc R . .
H37C H 0.1913 0.6788 -0.0905 0.044 Uiso 1 1 calc R . .
O4 O -0.37900(16) 0.4154(5) 0.39674(19) 0.0431(11) Uani 1 1 d D . .
H4A H -0.4167(10) 0.416(7) 0.404(2) 0.052 Uiso 1 1 d D . .
H4B H -0.3552(17) 0.458(6) 0.4287(18) 0.052 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
F1 0.0324(16) 0.048(2) 0.0305(17) -0.0023(16) 0.0047(14) 0.0083(15)
F2 0.0272(15) 0.056(2) 0.0300(17) 0.0069(16) 0.0021(13) 0.0123(15)
F3 0.0236(15) 0.072(2) 0.0338(18) 0.0066(18) -0.0051(13) -0.0032(16)
F4 0.0376(17) 0.048(2) 0.042(2) 0.0075(17) -0.0016(15) -0.0103(16)
F5 0.0360(17) 0.045(2) 0.043(2) 0.0076(17) 0.0025(15) 0.0059(15)
O1 0.0256(18) 0.047(2) 0.0172(18) 0.0065(18) 0.0060(15) 0.0047(17)
N1 0.018(2) 0.043(3) 0.017(2) 0.009(2) -0.0007(18) 0.0039(19)
N2 0.021(2) 0.032(2) 0.012(2) -0.0027(19) 0.0003(17) 0.0028(18)
N3 0.017(2) 0.032(2) 0.026(2) -0.002(2) 0.0020(18) 0.0025(19)
N4 0.025(2) 0.031(3) 0.038(3) 0.000(2) 0.002(2) 0.0049(19)
C1 0.029(3) 0.042(3) 0.018(3) 0.002(3) 0.009(2) -0.001(3)
C2 0.019(2) 0.045(3) 0.022(3) 0.007(3) 0.001(2) 0.009(2)
C3 0.016(2) 0.049(3) 0.021(3) 0.005(3) 0.000(2) 0.000(2)
C4 0.027(3) 0.042(3) 0.020(3) 0.003(3) 0.006(2) -0.006(2)
C5 0.025(3) 0.046(4) 0.020(3) 0.003(3) 0.002(2) 0.008(2)
C6 0.021(2) 0.047(3) 0.013(2) 0.000(2) 0.002(2) 0.002(2)
C7 0.027(3) 0.032(3) 0.017(3) -0.008(2) 0.005(2) 0.009(2)
C8 0.018(2) 0.024(3) 0.021(3) -0.006(2) 0.000(2) 0.001(2)
C9 0.028(3) 0.024(3) 0.019(2) -0.002(2) 0.007(2) 0.000(2)
C10 0.025(3) 0.035(3) 0.027(3) 0.002(3) -0.006(2) 0.003(2)
C11 0.018(2) 0.033(3) 0.027(3) -0.003(3) 0.001(2) 0.003(2)
C12 0.019(2) 0.038(3) 0.040(3) -0.011(3) 0.003(2) 0.002(2)
C13 0.036(3) 0.039(3) 0.020(3) -0.004(3) 0.011(2) -0.006(3)
O2 0.0234(17) 0.040(2) 0.0226(18) 0.0015(17) -0.0004(15) 0.0003(16)
O3 0.033(2) 0.051(3) 0.0207(19) -0.0115(19) -0.0025(16) 0.0062(18)
C14 0.032(3) 0.027(3) 0.020(3) -0.002(2) 0.002(2) 0.000(2)
C15 0.029(3) 0.022(3) 0.024(3) 0.002(2) 0.001(2) -0.005(2)
C16 0.019(2) 0.025(3) 0.023(3) 0.005(2) 0.005(2) -0.004(2)
C17 0.028(3) 0.021(3) 0.031(3) 0.003(2) 0.008(2) -0.001(2)
C18 0.035(3) 0.026(3) 0.026(3) 0.001(2) 0.007(2) 0.005(2)
C19 0.035(3) 0.027(3) 0.048(4) 0.010(3) 0.020(3) 0.003(2)
C20 0.025(3) 0.032(3) 0.048(4) 0.014(3) 0.009(3) 0.002(2)
C21 0.026(3) 0.031(3) 0.029(3) 0.014(3) -0.003(2) -0.003(2)
N5 0.026(2) 0.021(2) 0.017(2) -0.0006(18) 0.0045(17) 0.0017(17)
C22 0.026(2) 0.019(3) 0.022(3) -0.001(2) 0.004(2) -0.001(2)
C23 0.026(3) 0.034(3) 0.048(4) 0.007(3) -0.004(3) 0.002(2)
C24A 0.028(3) 0.030(5) 0.029(5) 0.003(4) 0.008(3) -0.001(3)
C25A 0.023(4) 0.026(4) 0.033(4) -0.004(3) -0.002(3) 0.000(3)
C24B 0.028(3) 0.030(5) 0.029(5) 0.003(4) 0.008(3) -0.001(3)
C25B 0.023(4) 0.026(4) 0.033(4) -0.004(3) -0.002(3) 0.000(3)
C26 0.026(2) 0.030(3) 0.014(2) -0.002(2) 0.003(2) -0.003(2)
C27 0.036(3) 0.025(3) 0.017(2) 0.001(2) 0.010(2) -0.003(2)
C28 0.032(3) 0.028(3) 0.017(2) -0.003(2) 0.006(2) -0.002(2)
C29 0.032(3) 0.042(3) 0.020(3) -0.005(3) 0.005(2) -0.004(2)
C30 0.026(2) 0.026(3) 0.018(2) -0.003(2) 0.004(2) 0.000(2)
C31 0.030(3) 0.031(3) 0.016(2) -0.001(2) 0.005(2) 0.001(2)
C32 0.029(3) 0.034(3) 0.018(3) -0.001(2) 0.004(2) 0.002(2)
C33 0.030(3) 0.033(3) 0.031(3) 0.000(3) 0.003(2) 0.002(2)
C34 0.028(3) 0.023(3) 0.017(2) 0.003(2) 0.003(2) 0.002(2)
C35 0.023(2) 0.027(3) 0.019(2) -0.005(2) 0.008(2) 0.001(2)
C36 0.032(3) 0.032(3) 0.014(2) 0.005(2) 0.006(2) 0.003(2)
C37 0.034(3) 0.030(3) 0.023(3) 0.000(2) 0.004(2) 0.000(2)
O4 0.0252(19) 0.059(3) 0.043(2) -0.022(2) -0.0008(18) 0.002(2)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
F1 C1 1.353(6) . ?
F2 C2 1.358(6) . ?
F3 C3 1.358(5) . ?
F4 C4 1.352(6) . ?
F5 C5 1.362(6) . ?
O1 C7 1.226(6) . ?
N1 C7 1.400(6) . ?
N1 C6 1.421(6) . ?
N2 C7 1.384(6) . ?
N2 C8 1.429(6) . ?
N3 C10 1.364(6) . ?
N3 C9 1.391(6) . ?
N4 C10 1.332(6) . ?
N4 C11 1.405(6) . ?
C1 C2 1.377(6) . ?
C1 C6 1.393(7) . ?
C2 C3 1.376(7) . ?
C3 C4 1.383(7) . ?
C4 C5 1.381(6) . ?
C5 C6 1.392(7) . ?
C8 C14 1.390(7) . ?
C8 C9 1.412(6) . ?
C9 C11 1.411(6) . ?
C11 C12 1.403(7) . ?
C12 C13 1.391(7) . ?
C13 C14 1.420(7) . ?
O2 C15 1.270(5) . ?
O3 C15 1.261(5) . ?
C15 C16 1.532(7) . ?
C16 C17 1.389(6) . ?
C16 C21 1.410(6) . ?
C17 C18 1.393(7) . ?
C18 C19 1.397(7) . ?
C19 C20 1.393(7) . ?
C20 C21 1.402(7) . ?
N5 C34 1.523(6) . ?
N5 C26 1.525(6) . ?
N5 C30 1.539(6) . ?
N5 C22 1.539(6) . ?
C22 C23 1.536(6) . ?
C23 C24B 1.520(15) . ?
C23 C24A 1.523(16) . ?
C24A C25A 1.54(2) . ?
C24B C25B 1.528(19) . ?
C26 C27 1.535(6) . ?
C27 C28 1.544(6) . ?
C28 C29 1.531(6) . ?
C30 C31 1.532(6) . ?
C31 C32 1.533(6) . ?
C32 C33 1.547(6) . ?
C34 C35 1.529(6) . ?
C35 C36 1.533(6) . ?
C36 C37 1.541(6) . ?

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
C7 N1 C6 120.6(4) . . ?
C7 N2 C8 125.7(4) . . ?
C10 N3 C9 106.1(4) . . ?
C10 N4 C11 103.6(4) . . ?
F1 C1 C2 119.2(5) . . ?
F1 C1 C6 119.3(4) . . ?
C2 C1 C6 121.5(5) . . ?
F2 C2 C3 119.8(4) . . ?
F2 C2 C1 119.8(5) . . ?
C3 C2 C1 120.3(5) . . ?
F3 C3 C2 120.0(5) . . ?
F3 C3 C4 120.1(5) . . ?
C2 C3 C4 120.0(4) . . ?
F4 C4 C5 120.9(5) . . ?
F4 C4 C3 120.1(4) . . ?
C5 C4 C3 119.0(5) . . ?
F5 C5 C4 117.9(5) . . ?
F5 C5 C6 119.6(4) . . ?
C4 C5 C6 122.5(5) . . ?
C5 C6 C1 116.8(4) . . ?
C5 C6 N1 120.0(5) . . ?
C1 C6 N1 123.2(5) . . ?
O1 C7 N2 126.6(5) . . ?
O1 C7 N1 122.9(4) . . ?
N2 C7 N1 110.5(4) . . ?
C14 C8 C9 117.1(4) . . ?
C14 C8 N2 126.0(4) . . ?
C9 C8 N2 116.9(4) . . ?
N3 C9 C11 105.7(4) . . ?
N3 C9 C8 132.2(4) . . ?
C11 C9 C8 122.0(4) . . ?
N4 C10 N3 114.6(5) . . ?
C12 C11 N4 129.2(4) . . ?
C12 C11 C9 120.8(4) . . ?
N4 C11 C9 110.0(4) . . ?
C13 C12 C11 116.7(5) . . ?
C12 C13 C14 122.9(5) . . ?
C8 C14 C13 120.3(4) . . ?
O3 C15 O2 124.0(5) . . ?
O3 C15 C16 118.2(4) . . ?
O2 C15 C16 117.7(4) . . ?
C17 C16 C21 119.5(5) . . ?
C17 C16 C15 121.4(4) . . ?
C21 C16 C15 119.1(4) . . ?
C16 C17 C18 120.8(5) . . ?
C17 C18 C19 119.9(5) . . ?
C20 C19 C18 119.9(5) . . ?
C19 C20 C21 120.3(5) . . ?
C20 C21 C16 119.6(5) . . ?
C34 N5 C26 106.4(3) . . ?
C34 N5 C30 110.5(3) . . ?
C26 N5 C30 111.8(3) . . ?
C34 N5 C22 111.1(3) . . ?
C26 N5 C22 111.0(3) . . ?
C30 N5 C22 106.2(3) . . ?
C23 C22 N5 115.2(4) . . ?
C24B C23 C24A 8.0(17) . . ?
C24B C23 C22 114.1(10) . . ?
C24A C23 C22 108.7(10) . . ?
C23 C24A C25A 111.3(15) . . ?
C23 C24B C25B 108.9(13) . . ?
N5 C26 C27 115.2(4) . . ?
C26 C27 C28 110.4(4) . . ?
C29 C28 C27 113.0(4) . . ?
C31 C30 N5 115.3(4) . . ?
C30 C31 C32 110.0(4) . . ?
C31 C32 C33 112.3(4) . . ?
N5 C34 C35 117.0(4) . . ?
C34 C35 C36 110.4(4) . . ?
C35 C36 C37 113.1(4) . . ?

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
N1 H1 O3 0.90(5) 1.99(5) 2.799(5) 149(4) 4_575
N2 H2 O3 0.96(5) 1.88(5) 2.795(6) 157(4) 4_575
N3 H3 O2 0.90(5) 1.90(5) 2.768(5) 161(4) 4_575
N3 H3 O3 0.90(5) 2.65(5) 3.397(6) 141(4) 4_575
O4 H4A N4 0.847(19) 2.08(2) 2.903(6) 164(5) 2_445
O4 H4B O2 0.855(19) 2.03(2) 2.878(5) 175(6) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067

#===END

data_2011jh1112
#TrackingRef '- 0101_1111_1112_1118_combined.cif'

_database_code_depnum_ccdc_archive 'CCDC 851120'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F5 N4 O'
_chemical_formula_weight         342.24

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'
F F 0.0171 0.0103 '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                   16.627(4)
_cell_length_b                   8.9654(18)
_cell_length_c                   17.878(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.051(4)
_cell_angle_gamma                90.00
_cell_volume                     2661.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9536
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      31.4

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_source_current           24.00
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   RA
_diffrn_radiation_monochromator  'Varimax mirror'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 4 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18568
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6004
_reflns_number_gt                5254
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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^ > 2\s(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.

All hydrogens were visible in the difference map; CH, CH2 and CH3
hydrogens were placed in idealised positions and refined using a riding
model, NH hydrogens were freely refined with thermal parameters fixed as
1.2 times that of the parent atom.
;

_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^)+(0.0331P)^2^+1.7063P] 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         6004
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.003
_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
F11 F 0.08503(8) 0.34327(14) 0.28712(7) 0.0273(3) Uani 1 1 d . . .
F12 F -0.05879(8) 0.28487(15) 0.21525(8) 0.0335(4) Uani 1 1 d . . .
F13 F -0.10711(9) 0.44282(17) 0.09126(9) 0.0412(4) Uani 1 1 d . . .
F14 F -0.00902(9) 0.65413(16) 0.03600(7) 0.0345(4) Uani 1 1 d . . .
F15 F 0.13602(8) 0.70871(14) 0.10579(7) 0.0256(3) Uani 1 1 d . . .
O11 O 0.24286(9) 0.33827(15) 0.21414(8) 0.0154(3) Uani 1 1 d . . .
N11 N 0.18853(11) 0.5656(2) 0.23538(10) 0.0183(4) Uani 1 1 d . . .
H11 H 0.1968(15) 0.655(3) 0.2440(13) 0.022 Uiso 1 1 d . . .
N12 N 0.32332(11) 0.5275(2) 0.26106(10) 0.0173(4) Uani 1 1 d . . .
H12 H 0.3230(14) 0.618(3) 0.2762(13) 0.021 Uiso 1 1 d . . .
N13 N 0.57468(11) 0.4626(2) 0.38083(10) 0.0178(4) Uani 1 1 d . . .
H13 H 0.6221(15) 0.423(3) 0.3979(13) 0.021 Uiso 1 1 d . . .
N14 N 0.45461(11) 0.57857(19) 0.37922(9) 0.0168(4) Uani 1 1 d . . .
C101 C 0.06308(13) 0.4203(2) 0.22516(12) 0.0196(5) Uani 1 1 d . . .
C102 C -0.01095(14) 0.3903(2) 0.18899(13) 0.0230(5) Uani 1 1 d . . .
C103 C -0.03503(14) 0.4700(3) 0.12569(14) 0.0251(5) Uani 1 1 d . . .
C104 C 0.01426(14) 0.5768(3) 0.09804(12) 0.0231(5) Uani 1 1 d . . .
C105 C 0.08812(13) 0.6045(2) 0.13381(12) 0.0185(4) Uani 1 1 d . . .
C106 C 0.11377(13) 0.5285(2) 0.19860(12) 0.0165(4) Uani 1 1 d . . .
C107 C 0.25174(13) 0.4696(2) 0.23618(11) 0.0150(4) Uani 1 1 d . . .
C108 C 0.39823(12) 0.4516(2) 0.26106(11) 0.0152(4) Uani 1 1 d . . .
C109 C 0.41751(13) 0.3501(2) 0.20611(11) 0.0174(4) Uani 1 1 d . . .
H109 H 0.3795 0.3302 0.1658 0.021 Uiso 1 1 calc R . .
C110 C 0.49208(13) 0.2764(2) 0.20903(12) 0.0179(4) Uani 1 1 d . . .
H110 H 0.5026 0.2061 0.1710 0.022 Uiso 1 1 calc R . .
C111 C 0.55071(13) 0.3025(2) 0.26527(12) 0.0179(4) Uani 1 1 d . . .
H111 H 0.6009 0.2515 0.2675 0.021 Uiso 1 1 calc R . .
C112 C 0.53155(12) 0.4084(2) 0.31844(11) 0.0158(4) Uani 1 1 d . . .
C113 C 0.52614(13) 0.5612(2) 0.41410(12) 0.0186(4) Uani 1 1 d . . .
H113 H 0.5421 0.6134 0.4587 0.022 Uiso 1 1 calc R . .
C114 C 0.45711(13) 0.4820(2) 0.31836(11) 0.0155(4) Uani 1 1 d . . .
F21 F 0.60574(8) -0.00907(14) 0.18211(7) 0.0240(3) Uani 1 1 d . . .
F22 F 0.54076(8) -0.13917(15) 0.05661(8) 0.0296(3) Uani 1 1 d . . .
F23 F 0.60011(9) -0.07687(15) -0.07857(7) 0.0324(4) Uani 1 1 d . . .
F24 F 0.72509(10) 0.11614(18) -0.08769(7) 0.0387(4) Uani 1 1 d . . .
F25 F 0.79243(9) 0.24250(16) 0.03761(7) 0.0314(3) Uani 1 1 d . . .
O21 O 0.77313(9) -0.02779(16) 0.23690(8) 0.0200(3) Uani 1 1 d . . .
N21 N 0.73516(11) 0.1895(2) 0.17876(10) 0.0177(4) Uani 1 1 d . . .
H21 H 0.7323(15) 0.278(3) 0.1822(14) 0.021 Uiso 1 1 d . . .
N22 N 0.77748(11) 0.1897(2) 0.30318(10) 0.0170(4) Uani 1 1 d . . .
H22 H 0.7614(14) 0.278(3) 0.3017(13) 0.020 Uiso 1 1 d . . .
N23 N 0.73749(12) 0.1796(2) 0.55641(10) 0.0217(4) Uani 1 1 d . . .
H23 H 0.7373(15) 0.171(3) 0.6058(14) 0.026 Uiso 1 1 d . . .
N24 N 0.70145(11) 0.2745(2) 0.44369(10) 0.0177(4) Uani 1 1 d . . .
C201 C 0.63718(13) 0.0219(2) 0.11611(12) 0.0180(4) Uani 1 1 d . . .
C202 C 0.60322(13) -0.0450(2) 0.05231(13) 0.0210(5) Uani 1 1 d . . .
C203 C 0.63257(14) -0.0125(3) -0.01637(12) 0.0229(5) Uani 1 1 d . . .
C204 C 0.69534(14) 0.0858(3) -0.02086(12) 0.0231(5) Uani 1 1 d . . .
C205 C 0.72996(13) 0.1497(2) 0.04356(12) 0.0203(5) Uani 1 1 d . . .
C206 C 0.70164(13) 0.1200(2) 0.11376(11) 0.0168(4) Uani 1 1 d . . .
C207 C 0.76298(12) 0.1084(2) 0.24020(11) 0.0157(4) Uani 1 1 d . . .
C208 C 0.80301(13) 0.1280(2) 0.37323(11) 0.0164(4) Uani 1 1 d . . .
C209 C 0.86575(14) 0.0263(2) 0.38214(12) 0.0218(5) Uani 1 1 d . . .
H209 H 0.8937 -0.0043 0.3398 0.026 Uiso 1 1 calc R . .
C210 C 0.88834(14) -0.0320(3) 0.45313(13) 0.0252(5) Uani 1 1 d . . .
H210 H 0.9313 -0.1018 0.4575 0.030 Uiso 1 1 calc R . .
C211 C 0.85013(15) 0.0088(2) 0.51699(12) 0.0244(5) Uani 1 1 d . . .
H211 H 0.8652 -0.0321 0.5647 0.029 Uiso 1 1 calc R . .
C212 C 0.78825(13) 0.1136(2) 0.50734(11) 0.0184(4) Uani 1 1 d . . .
C213 C 0.68779(13) 0.2734(2) 0.51597(12) 0.0205(5) Uani 1 1 d . . .
H213 H 0.6474 0.3321 0.5374 0.025 Uiso 1 1 calc R . .
C214 C 0.76471(13) 0.1742(2) 0.43704(11) 0.0160(4) Uani 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
F11 0.0340(8) 0.0226(7) 0.0253(7) 0.0043(6) 0.0035(6) -0.0006(6)
F12 0.0252(8) 0.0262(7) 0.0504(9) -0.0129(7) 0.0155(7) -0.0102(6)
F13 0.0209(8) 0.0421(9) 0.0585(10) -0.0197(8) -0.0169(7) 0.0013(7)
F14 0.0396(9) 0.0368(8) 0.0258(7) -0.0028(6) -0.0124(6) 0.0128(7)
F15 0.0285(8) 0.0227(7) 0.0259(7) 0.0035(6) 0.0043(6) -0.0001(6)
O11 0.0185(8) 0.0121(7) 0.0155(7) -0.0017(6) -0.0010(6) -0.0002(6)
N11 0.0174(9) 0.0126(9) 0.0244(9) -0.0035(8) -0.0034(7) 0.0012(7)
N12 0.0159(9) 0.0137(9) 0.0219(9) -0.0033(7) -0.0023(7) 0.0014(7)
N13 0.0165(9) 0.0188(9) 0.0178(9) 0.0011(7) -0.0027(7) 0.0034(7)
N14 0.0166(9) 0.0170(9) 0.0166(8) -0.0009(7) -0.0004(7) -0.0004(7)
C101 0.0218(12) 0.0161(11) 0.0209(10) -0.0032(9) 0.0027(9) 0.0027(9)
C102 0.0179(11) 0.0165(11) 0.0353(13) -0.0094(10) 0.0069(9) -0.0053(9)
C103 0.0143(11) 0.0254(12) 0.0348(13) -0.0149(10) -0.0053(9) 0.0035(9)
C104 0.0249(12) 0.0236(12) 0.0200(11) -0.0052(9) -0.0066(9) 0.0085(9)
C105 0.0182(11) 0.0164(10) 0.0210(10) -0.0012(9) 0.0027(8) 0.0006(8)
C106 0.0164(11) 0.0144(10) 0.0187(10) -0.0049(8) 0.0004(8) 0.0000(8)
C107 0.0183(11) 0.0151(10) 0.0113(9) 0.0008(8) -0.0014(8) 0.0011(8)
C108 0.0142(10) 0.0138(10) 0.0174(10) 0.0023(8) -0.0013(8) -0.0007(8)
C109 0.0192(11) 0.0167(10) 0.0159(9) 0.0008(8) -0.0027(8) -0.0014(8)
C110 0.0200(11) 0.0146(10) 0.0196(10) -0.0007(8) 0.0041(8) -0.0005(8)
C111 0.0160(10) 0.0167(10) 0.0211(10) 0.0024(9) 0.0028(8) 0.0018(8)
C112 0.0144(10) 0.0167(10) 0.0164(10) 0.0036(8) -0.0001(8) -0.0022(8)
C113 0.0186(11) 0.0201(11) 0.0168(10) -0.0004(9) -0.0004(8) -0.0017(9)
C114 0.0170(10) 0.0138(10) 0.0158(9) 0.0021(8) 0.0013(8) -0.0023(8)
F21 0.0234(7) 0.0260(7) 0.0232(6) 0.0031(6) 0.0063(5) -0.0012(6)
F22 0.0219(7) 0.0258(7) 0.0403(8) 0.0000(6) -0.0056(6) -0.0082(6)
F23 0.0381(9) 0.0335(8) 0.0241(7) -0.0096(6) -0.0123(6) -0.0032(7)
F24 0.0450(10) 0.0577(10) 0.0136(6) -0.0023(7) 0.0036(6) -0.0157(8)
F25 0.0333(8) 0.0412(8) 0.0196(6) 0.0014(6) 0.0005(6) -0.0195(7)
O21 0.0276(9) 0.0122(7) 0.0196(7) -0.0024(6) -0.0036(6) 0.0020(6)
N21 0.0263(10) 0.0107(9) 0.0159(8) -0.0021(7) -0.0023(7) -0.0014(7)
N22 0.0241(10) 0.0110(9) 0.0156(8) -0.0018(7) -0.0004(7) 0.0017(7)
N23 0.0282(11) 0.0244(10) 0.0123(8) 0.0004(8) -0.0002(8) 0.0033(8)
N24 0.0178(9) 0.0184(9) 0.0167(8) -0.0019(7) 0.0008(7) 0.0012(7)
C201 0.0197(11) 0.0169(11) 0.0177(10) 0.0027(9) 0.0032(8) 0.0037(8)
C202 0.0165(11) 0.0162(11) 0.0296(12) 0.0008(9) -0.0051(9) -0.0017(8)
C203 0.0246(12) 0.0221(12) 0.0211(11) -0.0061(9) -0.0085(9) 0.0013(9)
C204 0.0279(13) 0.0274(12) 0.0138(10) -0.0002(9) 0.0004(9) -0.0017(10)
C205 0.0196(11) 0.0209(11) 0.0204(10) 0.0002(9) 0.0001(9) -0.0048(9)
C206 0.0197(11) 0.0151(10) 0.0152(9) -0.0011(8) -0.0018(8) 0.0016(8)
C207 0.0169(11) 0.0157(11) 0.0144(9) -0.0003(8) 0.0000(8) -0.0015(8)
C208 0.0195(11) 0.0152(10) 0.0141(9) -0.0014(8) -0.0032(8) -0.0019(8)
C209 0.0230(12) 0.0202(11) 0.0219(11) -0.0060(9) -0.0027(9) 0.0034(9)
C210 0.0260(13) 0.0218(12) 0.0267(12) -0.0045(10) -0.0083(10) 0.0080(10)
C211 0.0340(14) 0.0198(11) 0.0183(10) 0.0006(9) -0.0090(10) 0.0043(10)
C212 0.0231(11) 0.0165(10) 0.0152(10) 0.0001(8) -0.0024(8) -0.0001(9)
C213 0.0196(11) 0.0245(12) 0.0173(10) -0.0010(9) 0.0009(8) 0.0000(9)
C214 0.0175(10) 0.0142(10) 0.0159(9) 0.0005(8) -0.0030(8) -0.0010(8)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
F11 C101 1.340(2) . ?
F12 C102 1.337(3) . ?
F13 C103 1.340(2) . ?
F14 C104 1.347(2) . ?
F15 C105 1.342(2) . ?
O11 C107 1.248(2) . ?
N11 C107 1.358(3) . ?
N11 C106 1.414(3) . ?
N12 C107 1.352(3) . ?
N12 C108 1.419(3) . ?
N13 C113 1.355(3) . ?
N13 C112 1.382(3) . ?
N14 C113 1.322(3) . ?
N14 C114 1.393(3) . ?
C101 C106 1.386(3) . ?
C101 C102 1.386(3) . ?
C102 C103 1.380(3) . ?
C103 C104 1.370(3) . ?
C104 C105 1.377(3) . ?
C105 C106 1.391(3) . ?
C108 C109 1.389(3) . ?
C108 C114 1.405(3) . ?
C109 C110 1.403(3) . ?
C110 C111 1.383(3) . ?
C111 C112 1.392(3) . ?
C112 C114 1.403(3) . ?
F21 C201 1.345(2) . ?
F22 C202 1.344(2) . ?
F23 C203 1.341(2) . ?
F24 C204 1.345(2) . ?
F25 C205 1.340(2) . ?
O21 C207 1.234(3) . ?
N21 C207 1.377(3) . ?
N21 C206 1.408(3) . ?
N22 C207 1.352(3) . ?
N22 C208 1.413(3) . ?
N23 C213 1.360(3) . ?
N23 C212 1.382(3) . ?
N24 C213 1.324(3) . ?
N24 C214 1.394(3) . ?
C201 C202 1.383(3) . ?
C201 C206 1.389(3) . ?
C202 C203 1.377(3) . ?
C203 C204 1.372(3) . ?
C204 C205 1.384(3) . ?
C205 C206 1.389(3) . ?
C208 C209 1.389(3) . ?
C208 C214 1.398(3) . ?
C209 C210 1.405(3) . ?
C210 C211 1.385(3) . ?
C211 C212 1.397(3) . ?
C212 C214 1.406(3) . ?

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
C107 N11 C106 121.10(18) . . ?
C107 N12 C108 124.99(18) . . ?
C113 N13 C112 106.73(18) . . ?
C113 N14 C114 103.40(18) . . ?
F11 C101 C106 120.05(19) . . ?
F11 C101 C102 118.8(2) . . ?
C106 C101 C102 121.2(2) . . ?
F12 C102 C103 120.2(2) . . ?
F12 C102 C101 120.3(2) . . ?
C103 C102 C101 119.6(2) . . ?
F13 C103 C104 119.9(2) . . ?
F13 C103 C102 119.7(2) . . ?
C104 C103 C102 120.3(2) . . ?
F14 C104 C103 120.4(2) . . ?
F14 C104 C105 120.0(2) . . ?
C103 C104 C105 119.6(2) . . ?
F15 C105 C104 119.00(19) . . ?
F15 C105 C106 119.34(19) . . ?
C104 C105 C106 121.7(2) . . ?
C101 C106 C105 117.60(19) . . ?
C101 C106 N11 122.72(19) . . ?
C105 C106 N11 119.67(19) . . ?
O11 C107 N12 123.60(19) . . ?
O11 C107 N11 121.08(19) . . ?
N12 C107 N11 115.30(19) . . ?
C109 C108 C114 117.68(19) . . ?
C109 C108 N12 123.33(18) . . ?
C114 C108 N12 118.97(19) . . ?
C108 C109 C110 121.24(19) . . ?
C111 C110 C109 122.3(2) . . ?
C110 C111 C112 115.71(19) . . ?
N13 C112 C111 131.5(2) . . ?
N13 C112 C114 104.80(18) . . ?
C111 C112 C114 123.65(19) . . ?
N14 C113 N13 114.31(18) . . ?
N14 C114 C112 110.77(18) . . ?
N14 C114 C108 129.90(19) . . ?
C112 C114 C108 119.33(19) . . ?
C207 N21 C206 121.73(17) . . ?
C207 N22 C208 123.97(18) . . ?
C213 N23 C212 107.55(18) . . ?
C213 N24 C214 104.36(17) . . ?
F21 C201 C202 118.3(2) . . ?
F21 C201 C206 119.61(19) . . ?
C202 C201 C206 122.1(2) . . ?
F22 C202 C203 119.7(2) . . ?
F22 C202 C201 120.6(2) . . ?
C203 C202 C201 119.7(2) . . ?
F23 C203 C204 120.1(2) . . ?
F23 C203 C202 120.2(2) . . ?
C204 C203 C202 119.7(2) . . ?
F24 C204 C203 119.92(19) . . ?
F24 C204 C205 120.0(2) . . ?
C203 C204 C205 120.1(2) . . ?
F25 C205 C204 118.7(2) . . ?
F25 C205 C206 119.49(18) . . ?
C204 C205 C206 121.8(2) . . ?
C201 C206 C205 116.61(19) . . ?
C201 C206 N21 121.86(19) . . ?
C205 C206 N21 121.50(19) . . ?
O21 C207 N22 123.66(18) . . ?
O21 C207 N21 121.71(18) . . ?
N22 C207 N21 114.63(18) . . ?
C209 C208 C214 118.21(19) . . ?
C209 C208 N22 123.2(2) . . ?
C214 C208 N22 118.62(19) . . ?
C208 C209 C210 120.7(2) . . ?
C211 C210 C209 122.3(2) . . ?
C210 C211 C212 116.3(2) . . ?
N23 C212 C211 132.8(2) . . ?
N23 C212 C214 104.58(18) . . ?
C211 C212 C214 122.6(2) . . ?
N24 C213 N23 113.1(2) . . ?
N24 C214 C208 129.72(18) . . ?
N24 C214 C212 110.40(19) . . ?
C208 C214 C212 119.86(19) . . ?

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
N11 H11 O11 0.82(3) 2.05(3) 2.825(2) 157(2) 2
N12 H12 O11 0.86(2) 2.27(2) 3.037(2) 149(2) 2
N13 H13 N24 0.90(2) 2.02(2) 2.881(3) 159(2) .
N21 H21 O21 0.80(2) 2.27(3) 2.956(2) 145(2) 2_655
N22 H22 O21 0.84(2) 1.95(2) 2.752(2) 161(2) 2_655
N23 H23 O11 0.89(2) 1.94(3) 2.821(2) 176(2) 4_666

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.056

#===END

data_2011jh1118
#TrackingRef '- 0101_1111_1112_1118_combined.cif'

_database_code_depnum_ccdc_archive 'CCDC 851121'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C17 H16 N6 O), 5(H2 O)'
_chemical_formula_sum            'C34 H42 N12 O7'
_chemical_formula_weight         730.8

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   'C 2/c'
_symmetry_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                   29.489(5)
_cell_length_b                   7.2109(11)
_cell_length_c                   18.264(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.114(8)
_cell_angle_gamma                90.00
_cell_volume                     3392.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platlet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r10 (Rigaku, 2011)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9118
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3888
_reflns_number_gt                3143
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r10 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r10 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r10 (Rigaku, 2011)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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^ > 2\s(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.
;

_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^)+(0.0726P)^2^+7.9703P] 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         3888
_refine_ls_number_parameters     260
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.079
_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 -0.06075(8) 0.1611(3) 0.53338(13) 0.0173(4) Uani 1 1 d . . .
H1 H -0.0901 0.1230 0.5359 0.021 Uiso 1 1 calc R . .
C2 C -0.01114(8) 0.2513(3) 0.48121(13) 0.0152(4) Uani 1 1 d . . .
C3 C 0.01743(8) 0.2382(3) 0.56877(13) 0.0138(4) Uani 1 1 d . . .
C4 C 0.01082(9) 0.3037(3) 0.43181(14) 0.0181(4) Uani 1 1 d . . .
H4 H -0.0086 0.3113 0.3737 0.022 Uiso 1 1 calc R . .
C5 C 0.06321(9) 0.3434(3) 0.47459(14) 0.0182(4) Uani 1 1 d . . .
H5A H 0.0795 0.3798 0.4443 0.022 Uiso 1 1 calc R . .
C6 C 0.09275(8) 0.3308(3) 0.56204(13) 0.0163(4) Uani 1 1 d . . .
H6A H 0.1279 0.3599 0.5881 0.020 Uiso 1 1 calc R . .
C7 C 0.07071(8) 0.2758(3) 0.61053(12) 0.0138(4) Uani 1 1 d . . .
C8 C 0.14875(8) 0.1979(3) 0.74317(13) 0.0142(4) Uani 1 1 d . . .
C9 C 0.21168(8) 0.1040(3) 0.88863(13) 0.0143(4) Uani 1 1 d . . .
C10 C 0.25878(8) 0.1280(3) 0.88974(13) 0.0155(4) Uani 1 1 d . . .
H10 H 0.2593 0.1777 0.8432 0.019 Uiso 1 1 calc R . .
C11 C 0.30561(8) 0.0778(3) 0.96067(13) 0.0165(4) Uani 1 1 d . . .
H11 H 0.3365 0.0951 0.9595 0.020 Uiso 1 1 calc R . .
C12 C 0.30776(8) 0.0038(3) 1.03228(13) 0.0161(4) Uani 1 1 d . . .
H12 H 0.3390 -0.0266 1.0793 0.019 Uiso 1 1 calc R . .
C13 C 0.26026(8) -0.0223(3) 1.02931(13) 0.0143(4) Uani 1 1 d . . .
C14 C 0.21295(8) 0.0215(3) 0.95923(13) 0.0136(4) Uani 1 1 d . . .
C15 C 0.19461(8) -0.0847(3) 1.05047(13) 0.0164(4) Uani 1 1 d . . .
H15 H 0.1763 -0.1230 1.0773 0.020 Uiso 1 1 calc R . .
C16 C 0.28285(9) -0.1451(3) 1.17374(13) 0.0195(4) Uani 1 1 d . . .
H16A H 0.3179 -0.1360 1.1837 0.029 Uiso 1 1 calc R . .
H16B H 0.2758 -0.2707 1.1825 0.029 Uiso 1 1 calc R . .
H16C H 0.2784 -0.0647 1.2117 0.029 Uiso 1 1 calc R . .
C17 C -0.10521(9) 0.1979(3) 0.37613(14) 0.0211(5) Uani 1 1 d . . .
H17A H -0.0939 0.2316 0.3367 0.032 Uiso 1 1 calc R . .
H17B H -0.1309 0.2847 0.3725 0.032 Uiso 1 1 calc R . .
H17C H -0.1199 0.0756 0.3635 0.032 Uiso 1 1 calc R . .
N1 N -0.06122(7) 0.2005(2) 0.46028(11) 0.0162(4) Uani 1 1 d . . .
N2 N -0.01497(7) 0.1819(2) 0.60050(11) 0.0159(4) Uani 1 1 d . . .
N3 N 0.17157(7) -0.0203(2) 0.97283(11) 0.0163(4) Uani 1 1 d . . .
N4 N 0.24707(7) -0.0903(2) 1.08760(11) 0.0157(4) Uani 1 1 d . . .
N5 N 0.09849(7) 0.2587(2) 0.69827(11) 0.0160(4) Uani 1 1 d . . .
H5 H 0.0828 0.2886 0.7258 0.019 Uiso 1 1 calc R . .
N6 N 0.16290(7) 0.1620(3) 0.82515(11) 0.0158(4) Uani 1 1 d . . .
H6 H 0.1392 0.1765 0.8393 0.019 Uiso 1 1 calc R . .
O1 O 0.17801(6) 0.1762(2) 0.71390(9) 0.0193(3) Uani 1 1 d . . .
O1W O 0.08937(7) -0.2286(2) 0.81691(11) 0.0236(4) Uani 1 1 d D . .
H1W H 0.0620(7) -0.163(4) 0.7962(18) 0.048(10) Uiso 1 1 d D . .
H2W H 0.1124(9) -0.182(5) 0.8625(14) 0.073(14) Uiso 1 1 d D . .
O2W O 0.06295(7) 0.3921(2) 0.80668(11) 0.0271(4) Uani 1 1 d D . .
H3W H 0.0670(11) 0.5083(15) 0.8073(19) 0.034(8) Uiso 1 1 d D . .
H4W H 0.0442(12) 0.361(4) 0.827(2) 0.051(10) Uiso 1 1 d D . .
O3W O 0.0000 0.0099(3) 0.2500 0.0203(5) Uani 1 2 d SD . .
H5W H -0.0011(14) -0.059(4) 0.2863(17) 0.051(10) 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
C1 0.0182(10) 0.0177(10) 0.0182(10) -0.0003(8) 0.0105(9) -0.0012(8)
C2 0.0174(10) 0.0137(9) 0.0149(10) -0.0005(7) 0.0080(8) 0.0007(7)
C3 0.0186(10) 0.0120(9) 0.0139(9) 0.0005(7) 0.0104(8) 0.0010(7)
C4 0.0245(11) 0.0181(10) 0.0142(10) 0.0008(8) 0.0113(9) 0.0019(8)
C5 0.0241(11) 0.0176(10) 0.0203(11) 0.0028(8) 0.0165(10) 0.0029(8)
C6 0.0176(10) 0.0156(10) 0.0183(10) 0.0007(8) 0.0109(9) 0.0007(8)
C7 0.0162(10) 0.0134(9) 0.0128(9) 0.0003(7) 0.0078(8) 0.0015(7)
C8 0.0158(10) 0.0142(9) 0.0136(10) -0.0022(7) 0.0079(8) -0.0021(8)
C9 0.0151(10) 0.0142(9) 0.0141(9) -0.0018(7) 0.0076(8) 0.0002(7)
C10 0.0169(10) 0.0167(9) 0.0159(10) -0.0024(8) 0.0102(9) -0.0016(8)
C11 0.0145(10) 0.0171(10) 0.0210(10) -0.0032(8) 0.0112(9) -0.0003(8)
C12 0.0132(9) 0.0160(10) 0.0175(10) -0.0012(8) 0.0063(8) 0.0013(8)
C13 0.0174(10) 0.0123(9) 0.0143(9) -0.0018(7) 0.0085(8) 0.0000(7)
C14 0.0132(9) 0.0135(9) 0.0153(9) -0.0021(7) 0.0079(8) -0.0007(7)
C15 0.0179(10) 0.0167(10) 0.0168(10) -0.0004(8) 0.0101(9) -0.0010(8)
C16 0.0215(11) 0.0206(10) 0.0134(10) 0.0018(8) 0.0062(9) 0.0016(9)
C17 0.0198(11) 0.0225(11) 0.0165(10) -0.0024(8) 0.0054(9) -0.0004(9)
N1 0.0157(9) 0.0173(8) 0.0138(8) -0.0015(7) 0.0058(7) -0.0018(7)
N2 0.0160(8) 0.0180(8) 0.0162(9) 0.0002(7) 0.0097(7) -0.0010(7)
N3 0.0156(9) 0.0194(9) 0.0163(9) -0.0001(7) 0.0097(7) -0.0010(7)
N4 0.0172(9) 0.0167(8) 0.0134(8) 0.0013(7) 0.0076(7) 0.0014(7)
N5 0.0153(9) 0.0222(9) 0.0131(8) -0.0007(7) 0.0089(7) 0.0015(7)
N6 0.0130(8) 0.0243(9) 0.0130(8) 0.0024(7) 0.0084(7) 0.0016(7)
O1 0.0166(7) 0.0291(8) 0.0142(7) -0.0004(6) 0.0092(6) 0.0020(6)
O1W 0.0229(9) 0.0252(8) 0.0227(9) -0.0004(7) 0.0112(7) 0.0023(7)
O2W 0.0334(10) 0.0281(9) 0.0324(10) -0.0087(7) 0.0259(8) -0.0069(8)
O3W 0.0281(12) 0.0175(11) 0.0169(11) 0.000 0.0122(10) 0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 1.318(3) . ?
C1 N1 1.359(3) . ?
C2 N1 1.383(3) . ?
C2 C4 1.394(3) . ?
C2 C3 1.402(3) . ?
C3 N2 1.397(2) . ?
C3 C7 1.399(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.387(3) . ?
C7 N5 1.406(3) . ?
C8 O1 1.226(2) . ?
C8 N6 1.369(3) . ?
C8 N5 1.371(3) . ?
C9 C10 1.390(3) . ?
C9 N6 1.402(3) . ?
C9 C14 1.404(3) . ?
C10 C11 1.406(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.388(3) . ?
C13 N4 1.389(2) . ?
C13 C14 1.395(3) . ?
C14 N3 1.391(2) . ?
C15 N3 1.323(3) . ?
C15 N4 1.354(3) . ?
C16 N4 1.459(3) . ?
C17 N1 1.451(3) . ?

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
N2 C1 N1 113.97(18) . . ?
N1 C2 C4 131.5(2) . . ?
N1 C2 C3 105.42(17) . . ?
C4 C2 C3 123.1(2) . . ?
N2 C3 C7 130.04(19) . . ?
N2 C3 C2 109.88(18) . . ?
C7 C3 C2 120.07(18) . . ?
C5 C4 C2 115.7(2) . . ?
C4 C5 C6 122.39(19) . . ?
C7 C6 C5 121.4(2) . . ?
C6 C7 C3 117.27(19) . . ?
C6 C7 N5 123.95(19) . . ?
C3 C7 N5 118.78(17) . . ?
O1 C8 N6 123.21(19) . . ?
O1 C8 N5 124.44(19) . . ?
N6 C8 N5 112.35(16) . . ?
C10 C9 N6 126.22(18) . . ?
C10 C9 C14 117.36(19) . . ?
N6 C9 C14 116.35(17) . . ?
C9 C10 C11 120.54(18) . . ?
C12 C11 C10 122.85(18) . . ?
C11 C12 C13 115.70(19) . . ?
C12 C13 N4 132.19(19) . . ?
C12 C13 C14 123.02(19) . . ?
N4 C13 C14 104.79(17) . . ?
N3 C14 C13 111.08(17) . . ?
N3 C14 C9 128.46(19) . . ?
C13 C14 C9 120.41(18) . . ?
N3 C15 N4 114.39(18) . . ?
C1 N1 C2 106.55(17) . . ?
C1 N1 C17 127.93(18) . . ?
C2 N1 C17 125.48(18) . . ?
C1 N2 C3 104.18(17) . . ?
C15 N3 C14 103.28(17) . . ?
C15 N4 C13 106.46(17) . . ?
C15 N4 C16 126.77(17) . . ?
C13 N4 C16 126.65(18) . . ?
C8 N5 C7 124.81(16) . . ?
C8 N6 C9 127.21(17) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.071

#===END