# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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
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# 
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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.
#
data_a:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 vanillic acid (bis) caffeine co-crystal 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N8 O8'
_chemical_formula_weight         556.54

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'

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

_cell_length_a                   10.110(2)
_cell_length_b                   10.525(2)
_cell_length_c                   12.221(2)
_cell_angle_alpha                77.69(3)
_cell_angle_beta                 81.26(3)
_cell_angle_gamma                82.69(3)
_cell_volume                     1249.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12163
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      28.34

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 'SADABS; Sheldrick, 1996'  
;

_diffrn_ambient_temperature      173(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 Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            12163
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.34
_reflns_number_total             6186
_reflns_number_gt                4486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0803P)²+0.6205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6186
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
O3 O 0.06860(13) 0.58682(15) 0.31599(12) 0.0315(3) Uani 1 1 d . . .
O4 O -0.01118(13) 0.73496(14) 0.12476(11) 0.0297(3) Uani 1 1 d . . .
O2 O -0.55870(14) 0.71382(17) 0.40060(13) 0.0394(4) Uani 1 1 d . . .
C1 C -0.33700(18) 0.71200(19) 0.30992(16) 0.0238(4) Uani 1 1 d . . .
O1 O -0.52052(14) 0.84956(15) 0.23297(13) 0.0346(4) Uani 1 1 d . . .
C6 C -0.24523(18) 0.74936(18) 0.21376(16) 0.0229(4) Uani 1 1 d . . .
H6 H -0.2758 0.8042 0.1482 0.027 Uiso 1 1 calc R . .
C5 C -0.11017(18) 0.70649(18) 0.21405(15) 0.0228(4) Uani 1 1 d . . .
C4 C -0.06406(18) 0.62743(19) 0.31131(16) 0.0241(4) Uani 1 1 d . . .
C8 C -0.48021(19) 0.7658(2) 0.30879(16) 0.0261(4) Uani 1 1 d . . .
C2 C -0.2914(2) 0.6307(2) 0.40494(16) 0.0292(4) Uani 1 1 d . . .
H2 H -0.3538 0.6028 0.4694 0.035 Uiso 1 1 calc R . .
C3 C -0.1556(2) 0.5899(2) 0.40641(17) 0.0292(4) Uani 1 1 d . . .
H3 H -0.1251 0.5362 0.4725 0.035 Uiso 1 1 calc R . .
C7 C -0.0499(2) 0.8267(2) 0.02770(17) 0.0309(4) Uani 1 1 d . . .
H7B H -0.1155 0.7906 -0.0055 0.046 Uiso 1 1 calc R . .
H7A H 0.0296 0.8438 -0.0281 0.046 Uiso 1 1 calc R . .
H7C H -0.0902 0.9085 0.0502 0.046 Uiso 1 1 calc R . .
O6 O -1.11997(14) 1.04025(15) 0.22365(12) 0.0323(3) Uani 1 1 d . . .
N12 N -0.96498(15) 0.92000(16) 0.32990(13) 0.0237(3) Uani 1 1 d . . .
O5 O -1.26852(14) 0.87567(16) 0.59496(13) 0.0366(4) Uani 1 1 d . . .
N14 N -0.81865(15) 0.78841(16) 0.46124(13) 0.0246(3) Uani 1 1 d . . .
C11 C -1.09325(19) 0.97646(19) 0.31471(16) 0.0244(4) Uani 1 1 d . . .
N10 N -1.19207(15) 0.95857(16) 0.40913(14) 0.0261(4) Uani 1 1 d . . .
C9 C -1.17504(19) 0.88563(19) 0.51841(17) 0.0260(4) Uani 1 1 d . . .
C20 C -0.8553(2) 0.9375(2) 0.23599(16) 0.0289(4) Uani 1 1 d . . .
H20A H -0.8154 0.8519 0.2216 0.043 Uiso 1 1 calc R . .
H20B H -0.7866 0.9835 0.2556 0.043 Uiso 1 1 calc R . .
H20C H -0.8909 0.9890 0.1681 0.043 Uiso 1 1 calc R . .
C17 C -1.03901(18) 0.83087(18) 0.52405(15) 0.0234(4) Uani 1 1 d . . .
N16 N -0.97516(16) 0.75626(16) 0.61264(14) 0.0265(4) Uani 1 1 d . . .
C13 C -0.93970(18) 0.84821(18) 0.43379(15) 0.0220(4) Uani 1 1 d . . .
C19 C -1.3277(2) 1.0226(2) 0.3922(2) 0.0361(5) Uani 1 1 d . . .
H19B H -1.3778 0.9646 0.3647 0.054 Uiso 1 1 calc R . .
H19C H -1.3205 1.1044 0.3366 0.054 Uiso 1 1 calc R . .
H19A H -1.3750 1.0413 0.4640 0.054 Uiso 1 1 calc R . .
C15 C -0.8458(2) 0.7342(2) 0.57102(17) 0.0276(4) Uani 1 1 d . . .
H15 H -0.7798 0.6851 0.6148 0.033 Uiso 1 1 calc R . .
C18 C -1.0360(2) 0.7106(2) 0.72920(17) 0.0349(5) Uani 1 1 d . . .
H18A H -0.9652 0.6849 0.7785 0.052 Uiso 1 1 calc R . .
H18B H -1.0854 0.6354 0.7324 0.052 Uiso 1 1 calc R . .
H18C H -1.0980 0.7811 0.7545 0.052 Uiso 1 1 calc R . .
O7 O 0.29087(14) 0.64618(16) 0.15362(13) 0.0355(4) Uani 1 1 d . . .
O8 O 0.67052(16) 0.36531(16) 0.22198(14) 0.0409(4) Uani 1 1 d . . .
N9 N 0.48236(16) 0.50657(16) 0.18936(13) 0.0267(4) Uani 1 1 d . . .
N22 N 0.68735(15) 0.52745(17) 0.06640(14) 0.0277(4) Uani 1 1 d . . .
C28 C 0.41188(18) 0.61460(19) 0.12667(16) 0.0246(4) Uani 1 1 d . . .
C21 C 0.6177(2) 0.4607(2) 0.16283(17) 0.0279(4) Uani 1 1 d . . .
C27 C 0.49480(18) 0.68002(19) 0.03204(15) 0.0241(4) Uani 1 1 d . . .
C23 C 0.62686(19) 0.6383(2) 0.00384(16) 0.0257(4) Uani 1 1 d . . .
N26 N 0.46731(18) 0.79387(19) -0.04571(16) 0.0350(4) Uani 1 1 d . . .
N24 N 0.68709(19) 0.7165(2) -0.08740(16) 0.0390(5) Uani 1 1 d . . .
C29 C 0.4095(2) 0.4360(2) 0.29323(19) 0.0406(5) Uani 1 1 d . . .
H29A H 0.3658 0.3663 0.2755 0.061 Uiso 1 1 calc R . .
H29B H 0.3412 0.4968 0.3261 0.061 Uiso 1 1 calc R . .
H29C H 0.4729 0.3979 0.3474 0.061 Uiso 1 1 calc R . .
C30 C 0.8290(2) 0.4834(3) 0.0349(2) 0.0398(5) Uani 1 1 d . . .
H30B H 0.8858 0.5204 0.0759 0.060 Uiso 1 1 calc R . .
H30C H 0.8535 0.5124 -0.0465 0.060 Uiso 1 1 calc R . .
H30A H 0.8423 0.3878 0.0544 0.060 Uiso 1 1 calc R . .
C25 C 0.5856(2) 0.8112(3) -0.1153(2) 0.0425(6) Uani 1 1 d . . .
H25 H 0.5962 0.8824 -0.1774 0.051 Uiso 1 1 calc R . .
C31 C 0.3450(3) 0.8808(3) -0.0540(3) 0.0535(7) Uani 1 1 d . . .
H31A H 0.3624 0.9588 -0.1122 0.080 Uiso 1 1 calc R . .
H31C H 0.3138 0.9064 0.0188 0.080 Uiso 1 1 calc R . .
H31B H 0.2758 0.8360 -0.0744 0.080 Uiso 1 1 calc R . .
H1 H -0.6456 0.7368 0.4062 0.069(10) Uiso 1 1 d R . .
H11 H 0.1198 0.6194 0.2563 0.064(9) Uiso 1 1 d 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
O3 C4 1.361(2) . ?
O3 H11 0.8611 . ?
O4 C5 1.374(2) . ?
O4 C7 1.431(2) . ?
O2 C8 1.329(2) . ?
O2 H1 0.8771 . ?
C1 C2 1.390(3) . ?
C1 C6 1.400(3) . ?
C1 C8 1.487(3) . ?
O1 C8 1.215(2) . ?
C6 C5 1.383(3) . ?
C6 H6 0.9500 . ?
C5 C4 1.404(3) . ?
C4 C3 1.391(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
O6 C11 1.220(2) . ?
N12 C13 1.374(2) . ?
N12 C11 1.378(2) . ?
N12 C20 1.468(2) . ?
O5 C9 1.222(2) . ?
N14 C15 1.342(3) . ?
N14 C13 1.358(2) . ?
C11 N10 1.404(2) . ?
N10 C9 1.415(3) . ?
N10 C19 1.473(3) . ?
C9 C17 1.428(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 C13 1.372(3) . ?
C17 N16 1.388(2) . ?
N16 C15 1.339(3) . ?
N16 C18 1.468(2) . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19A 0.9800 . ?
C15 H15 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O7 C28 1.240(2) . ?
O8 C21 1.220(2) . ?
N9 C21 1.405(3) . ?
N9 C28 1.406(3) . ?
N9 C29 1.469(3) . ?
N22 C21 1.378(3) . ?
N22 C23 1.379(3) . ?
N22 C30 1.467(2) . ?
C28 C27 1.424(3) . ?
C27 C23 1.367(3) . ?
C27 N26 1.388(3) . ?
C23 N24 1.350(3) . ?
N26 C25 1.366(3) . ?
N26 C31 1.445(3) . ?
N24 C25 1.365(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 H30A 0.9800 . ?
C25 H25 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31C 0.9800 . ?
C31 H31B 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
C4 O3 H11 113.3 . . ?
C5 O4 C7 116.73(15) . . ?
C8 O2 H1 119.3 . . ?
C2 C1 C6 119.50(17) . . ?
C2 C1 C8 121.85(17) . . ?
C6 C1 C8 118.59(17) . . ?
C5 C6 C1 120.07(17) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O4 C5 C6 125.43(17) . . ?
O4 C5 C4 114.35(16) . . ?
C6 C5 C4 120.22(17) . . ?
O3 C4 C3 118.57(17) . . ?
O3 C4 C5 121.90(17) . . ?
C3 C4 C5 119.52(17) . . ?
O1 C8 O2 123.77(18) . . ?
O1 C8 C1 123.62(18) . . ?
O2 C8 C1 112.60(17) . . ?
C3 C2 C1 120.57(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.08(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O4 C7 H7B 109.5 . . ?
O4 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
C13 N12 C11 119.71(16) . . ?
C13 N12 C20 120.03(16) . . ?
C11 N12 C20 120.25(16) . . ?
C15 N14 C13 103.34(16) . . ?
O6 C11 N12 121.71(18) . . ?
O6 C11 N10 121.24(17) . . ?
N12 C11 N10 117.05(16) . . ?
C11 N10 C9 126.89(16) . . ?
C11 N10 C19 116.32(17) . . ?
C9 N10 C19 116.79(17) . . ?
O5 C9 N10 121.63(18) . . ?
O5 C9 C17 127.18(19) . . ?
N10 C9 C17 111.18(16) . . ?
N12 C20 H20A 109.5 . . ?
N12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C17 N16 104.94(16) . . ?
C13 C17 C9 123.32(17) . . ?
N16 C17 C9 131.72(17) . . ?
C15 N16 C17 106.33(16) . . ?
C15 N16 C18 126.42(18) . . ?
C17 N16 C18 127.25(17) . . ?
N14 C13 C17 112.03(17) . . ?
N14 C13 N12 126.14(16) . . ?
C17 C13 N12 121.83(17) . . ?
N10 C19 H19B 109.5 . . ?
N10 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N10 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
N16 C15 N14 113.36(18) . . ?
N16 C15 H15 123.3 . . ?
N14 C15 H15 123.3 . . ?
N16 C18 H18A 109.5 . . ?
N16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 N9 C28 125.88(16) . . ?
C21 N9 C29 116.60(17) . . ?
C28 N9 C29 117.51(17) . . ?
C21 N22 C23 120.34(16) . . ?
C21 N22 C30 119.12(18) . . ?
C23 N22 C30 120.44(18) . . ?
O7 C28 N9 121.97(17) . . ?
O7 C28 C27 125.55(18) . . ?
N9 C28 C27 112.48(16) . . ?
O8 C21 N22 121.59(19) . . ?
O8 C21 N9 121.40(19) . . ?
N22 C21 N9 117.01(17) . . ?
C23 C27 N26 106.15(17) . . ?
C23 C27 C28 123.17(18) . . ?
N26 C27 C28 130.65(18) . . ?
N24 C23 C27 113.23(19) . . ?
N24 C23 N22 125.80(18) . . ?
C27 C23 N22 120.97(17) . . ?
C25 N26 C27 104.63(18) . . ?
C25 N26 C31 125.4(2) . . ?
C27 N26 C31 129.94(19) . . ?
C23 N24 C25 102.24(18) . . ?
N9 C29 H29A 109.5 . . ?
N9 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N9 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N22 C30 H30B 109.5 . . ?
N22 C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N22 C30 H30A 109.5 . . ?
H30B C30 H30A 109.5 . . ?
H30C C30 H30A 109.5 . . ?
N24 C25 N26 113.8(2) . . ?
N24 C25 H25 123.1 . . ?
N26 C25 H25 123.1 . . ?
N26 C31 H31A 109.5 . . ?
N26 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
N26 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31C C31 H31B 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.059

# start Validation Reply Form
_vrf_DIFMX01_c_                  
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: One of the caffeine molecules is disordered.
;
_vrf_PLAT097_c_                  
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.88 eA-3
RESPONSE: Residual electron density near one of the caffeine molecules 
          between O7 and C31 could not be modelled.
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl methylketone'
_database_code_depnum_ccdc_archive 'CCDC 1022106'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_b:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (bis) vanillic acid theophylline co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N4 O10'
_chemical_formula_weight         515.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   11.2741(6)
_cell_length_b                   15.7712(10)
_cell_length_c                   13.3746(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.572(2)
_cell_angle_gamma                90.00
_cell_volume                     2378.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    29773
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      28.33

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1076
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 'SADABS; Sheldrick, 1996'   
;

_diffrn_ambient_temperature      173(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 Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            29262
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5876
_reflns_number_gt                4478
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0577P)²+0.9568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5876
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O5 O 0.89248(12) 0.23961(7) 0.36204(8) 0.0332(3) Uani 1 1 d . . .
C17 C 0.80189(14) 0.28620(9) 0.21135(11) 0.0254(3) Uani 1 1 d . . .
O3A O 0.41130(12) 0.68432(8) -0.38659(9) 0.0385(3) Uani 1 1 d . . .
N14 N 0.71955(13) 0.32448(9) 0.06384(10) 0.0312(3) Uani 1 1 d . . .
O6 O 0.86638(12) 0.52322(7) 0.29698(9) 0.0373(3) Uani 1 1 d . . .
N12 N 0.79157(12) 0.43468(8) 0.17806(10) 0.0273(3) Uani 1 1 d . . .
N10 N 0.87464(12) 0.38185(8) 0.32964(10) 0.0270(3) Uani 1 1 d . . .
N16 N 0.77053(13) 0.21410(8) 0.15937(10) 0.0292(3) Uani 1 1 d . . .
O1A O 0.54917(16) 0.33725(9) -0.18177(12) 0.0606(5) Uani 1 1 d . . .
O2A O 0.62375(15) 0.42935(9) -0.07228(11) 0.0530(4) Uani 1 1 d . . .
C13 C 0.76968(14) 0.35252(9) 0.15071(11) 0.0248(3) Uani 1 1 d . . .
C5A C 0.50784(15) 0.63428(11) -0.23618(12) 0.0315(4) Uani 1 1 d . . .
C9 C 0.85852(14) 0.29649(9) 0.30524(11) 0.0254(3) Uani 1 1 d . . .
C11 C 0.84449(15) 0.45099(9) 0.26871(12) 0.0274(3) Uani 1 1 d . . .
C15 C 0.72239(16) 0.24010(11) 0.07303(12) 0.0329(4) Uani 1 1 d . . .
H15 H 0.6931 0.2024 0.0232 0.039 Uiso 1 1 calc R . .
C22 C 0.93191(17) 0.40270(10) 0.42587(13) 0.0351(4) Uani 1 1 d . . .
H59 H 0.9575 0.3503 0.4591 0.053 Uiso 1 1 calc R . .
H61 H 0.8754 0.4327 0.4684 0.053 Uiso 1 1 calc R . .
H60 H 1.0010 0.4390 0.4142 0.053 Uiso 1 1 calc R . .
O4A O 0.36611(14) 0.53273(9) -0.44926(10) 0.0331(4) Uani 0.812(3) 1 d P A 1
C3A C 0.42736(15) 0.53758(10) -0.35989(12) 0.0290(3) Uani 1 1 d . . .
C2A C 0.46563(15) 0.46975(10) -0.30318(12) 0.0307(4) Uani 1 1 d . A .
H2A H 0.4509 0.4135 -0.3255 0.037 Uiso 1 1 calc R . .
C6A C 0.54612(15) 0.56586(11) -0.17955(12) 0.0313(4) Uani 1 1 d . A .
H6A H 0.5863 0.5752 -0.1177 0.038 Uiso 1 1 calc R . .
C4A C 0.44943(15) 0.62071(10) -0.32675(12) 0.0281(3) Uani 1 1 d . A .
C1A C 0.52603(15) 0.48357(11) -0.21283(12) 0.0308(4) Uani 1 1 d . . .
C34 C 0.76722(17) 0.50614(10) 0.11077(14) 0.0374(4) Uani 1 1 d . . .
H50 H 0.7951 0.4924 0.0435 0.056 Uiso 1 1 calc R . .
H52 H 0.8086 0.5567 0.1355 0.056 Uiso 1 1 calc R . .
H51 H 0.6817 0.5170 0.1083 0.056 Uiso 1 1 calc R . .
C8A C 0.56665(16) 0.40932(11) -0.15431(13) 0.0347(4) Uani 1 1 d . A .
C7A C 0.3359(2) 0.44937(14) -0.48384(16) 0.0378(5) Uani 0.812(3) 1 d P A 1
H56 H 0.4085 0.4160 -0.4923 0.057 Uiso 0.812(3) 1 calc PR A 1
H58 H 0.2937 0.4535 -0.5481 0.057 Uiso 0.812(3) 1 calc PR A 1
H57 H 0.2849 0.4216 -0.4348 0.057 Uiso 0.812(3) 1 calc PR A 1
O1 O 0.81301(12) 0.04966(7) 0.22313(9) 0.0373(3) Uani 1 1 d . . .
O4 O 0.80232(12) -0.27679(7) 0.20777(9) 0.0386(3) Uani 1 1 d . . .
O2 O 0.90978(12) 0.07248(7) 0.36825(9) 0.0359(3) Uani 1 1 d . . .
C5 C 0.84426(15) -0.21324(9) 0.26819(12) 0.0280(3) Uani 1 1 d . . .
O3 O 0.92053(13) -0.32484(7) 0.37447(10) 0.0440(4) Uani 1 1 d . . .
C1 C 0.87891(14) -0.06876(9) 0.31905(12) 0.0256(3) Uani 1 1 d . . .
C2 C 0.93859(14) -0.09688(9) 0.40403(12) 0.0263(3) Uani 1 1 d . . .
H2 H 0.9708 -0.0571 0.4502 0.032 Uiso 1 1 calc R . .
C3 C 0.95122(15) -0.18303(10) 0.42147(12) 0.0286(3) Uani 1 1 d . . .
H3 H 0.9919 -0.2021 0.4798 0.034 Uiso 1 1 calc R . .
C8 C 0.86391(15) 0.02297(9) 0.29763(12) 0.0279(3) Uani 1 1 d . . .
C6 C 0.83161(14) -0.12741(9) 0.25097(12) 0.0275(3) Uani 1 1 d . . .
H6 H 0.7907 -0.1081 0.1928 0.033 Uiso 1 1 calc R . .
C7 C 0.74707(19) -0.25215(11) 0.11616(13) 0.0398(4) Uani 1 1 d . . .
H7B H 0.6774 -0.2171 0.1302 0.060 Uiso 1 1 calc R . .
H7C H 0.7224 -0.3028 0.0790 0.060 Uiso 1 1 calc R . .
H7A H 0.8033 -0.2195 0.0761 0.060 Uiso 1 1 calc R . .
C4 C 0.90490(16) -0.24170(9) 0.35443(12) 0.0296(3) Uani 1 1 d . . .
H1 H 0.904(2) 0.1318(17) 0.3623(18) 0.064(7) Uiso 1 1 d . . .
H11A H 0.426(2) 0.7353(18) -0.355(2) 0.069(8) Uiso 1 1 d . . .
H1A H 0.653(2) 0.3842(17) -0.035(2) 0.069(8) Uiso 1 1 d . . .
O5A O 0.5201(6) 0.7047(4) -0.2020(4) 0.0321(17) Uani 0.188(3) 1 d P A 2
C9A C 0.5747(11) 0.7231(6) -0.1037(7) 0.045(3) Uani 0.188(3) 1 d P A 2
H54 H 0.5297 0.6945 -0.0512 0.068 Uiso 0.188(3) 1 calc PR A 2
H55 H 0.5739 0.7845 -0.0919 0.068 Uiso 0.188(3) 1 calc PR A 2
H53 H 0.6568 0.7027 -0.1026 0.068 Uiso 0.188(3) 1 calc PR A 2
H16 H 0.7779 0.1579 0.1784 0.047(6) Uiso 1 1 d R . .
H11 H 0.8929 -0.3589 0.3236 0.090(10) Uiso 1 1 d 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
O5 C9 1.2340(18) . ?
C17 C13 1.370(2) . ?
C17 N16 1.3771(19) . ?
C17 C9 1.412(2) . ?
O3A C4A 1.3508(19) . ?
O3A H11A 0.92(3) . ?
N14 C15 1.337(2) . ?
N14 C13 1.361(2) . ?
O6 C11 1.2246(18) . ?
N12 C13 1.3680(19) . ?
N12 C11 1.370(2) . ?
N12 C34 1.4666(19) . ?
N10 C9 1.3968(18) . ?
N10 C11 1.4011(19) . ?
N10 C22 1.471(2) . ?
N16 C15 1.336(2) . ?
N16 H16 0.9258 . ?
O1A C8A 1.210(2) . ?
O2A C8A 1.305(2) . ?
O2A H1A 0.93(3) . ?
C5A O5A 1.209(6) . ?
C5A C6A 1.385(2) . ?
C5A C4A 1.390(2) . ?
C15 H15 0.9500 . ?
C22 H59 0.9800 . ?
C22 H61 0.9800 . ?
C22 H60 0.9800 . ?
O4A C3A 1.3765(19) . ?
O4A C7A 1.434(2) . ?
C3A C2A 1.378(2) . ?
C3A C4A 1.405(2) . ?
C2A C1A 1.398(2) . ?
C2A H2A 0.9500 . ?
C6A C1A 1.390(2) . ?
C6A H6A 0.9500 . ?
C1A C8A 1.479(2) . ?
C34 H50 0.9800 . ?
C34 H52 0.9800 . ?
C34 H51 0.9800 . ?
C7A H56 0.9800 . ?
C7A H58 0.9800 . ?
C7A H57 0.9800 . ?
O1 C8 1.2198(19) . ?
O4 C5 1.3688(18) . ?
O4 C7 1.423(2) . ?
O2 C8 1.3263(19) . ?
O2 H1 0.94(3) . ?
C5 C6 1.380(2) . ?
C5 C4 1.408(2) . ?
O3 C4 1.3495(19) . ?
O3 H11 0.9186 . ?
C1 C2 1.388(2) . ?
C1 C6 1.400(2) . ?
C1 C8 1.484(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
O5A C9A 1.475(10) . ?
C9A H54 0.9800 . ?
C9A H55 0.9800 . ?
C9A H53 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
C13 C17 N16 105.44(13) . . ?
C13 C17 C9 123.59(14) . . ?
N16 C17 C9 130.94(13) . . ?
C4A O3A H11A 109.0(16) . . ?
C15 N14 C13 103.64(13) . . ?
C13 N12 C11 119.35(12) . . ?
C13 N12 C34 122.12(14) . . ?
C11 N12 C34 118.42(13) . . ?
C9 N10 C11 125.73(13) . . ?
C9 N10 C22 118.34(12) . . ?
C11 N10 C22 115.89(12) . . ?
C15 N16 C17 106.44(13) . . ?
C15 N16 H16 124.5 . . ?
C17 N16 H16 129.0 . . ?
C8A O2A H1A 116.2(16) . . ?
N14 C13 N12 127.47(14) . . ?
N14 C13 C17 111.25(13) . . ?
N12 C13 C17 121.24(14) . . ?
O5A C5A C6A 118.4(3) . . ?
O5A C5A C4A 121.5(3) . . ?
C6A C5A C4A 119.95(15) . . ?
O5 C9 N10 121.20(13) . . ?
O5 C9 C17 126.77(13) . . ?
N10 C9 C17 112.03(13) . . ?
O6 C11 N12 122.17(14) . . ?
O6 C11 N10 119.82(14) . . ?
N12 C11 N10 118.00(13) . . ?
N16 C15 N14 113.23(14) . . ?
N16 C15 H15 123.4 . . ?
N14 C15 H15 123.4 . . ?
N10 C22 H59 109.5 . . ?
N10 C22 H61 109.5 . . ?
H59 C22 H61 109.5 . . ?
N10 C22 H60 109.5 . . ?
H59 C22 H60 109.5 . . ?
H61 C22 H60 109.5 . . ?
C3A O4A C7A 116.52(15) . . ?
O4A C3A C2A 125.90(14) . . ?
O4A C3A C4A 114.29(14) . . ?
C2A C3A C4A 119.81(14) . . ?
C3A C2A C1A 120.11(15) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C5A C6A C1A 120.23(14) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
O3A C4A C5A 123.19(15) . . ?
O3A C4A C3A 116.85(14) . . ?
C5A C4A C3A 119.96(14) . . ?
C6A C1A C2A 119.92(15) . . ?
C6A C1A C8A 121.42(14) . . ?
C2A C1A C8A 118.66(15) . . ?
N12 C34 H50 109.5 . . ?
N12 C34 H52 109.5 . . ?
H50 C34 H52 109.5 . . ?
N12 C34 H51 109.5 . . ?
H50 C34 H51 109.5 . . ?
H52 C34 H51 109.5 . . ?
O1A C8A O2A 124.06(16) . . ?
O1A C8A C1A 122.31(16) . . ?
O2A C8A C1A 113.62(15) . . ?
C5 O4 C7 117.00(12) . . ?
C8 O2 H1 119.8(15) . . ?
O4 C5 C6 125.82(14) . . ?
O4 C5 C4 114.34(13) . . ?
C6 C5 C4 119.85(14) . . ?
C4 O3 H11 112.3 . . ?
C2 C1 C6 120.00(14) . . ?
C2 C1 C8 121.53(14) . . ?
C6 C1 C8 118.47(14) . . ?
C3 C2 C1 119.96(14) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.53(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O1 C8 O2 123.75(14) . . ?
O1 C8 C1 123.07(14) . . ?
O2 C8 C1 113.18(13) . . ?
C5 C6 C1 120.10(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O4 C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
O3 C4 C3 118.18(14) . . ?
O3 C4 C5 122.25(14) . . ?
C3 C4 C5 119.57(14) . . ?
C5A O5A C9A 124.3(6) . . ?
O5A C9A H54 109.5 . . ?
O5A C9A H55 109.5 . . ?
H54 C9A H55 109.5 . . ?
O5A C9A H53 109.5 . . ?
H54 C9A H53 109.5 . . ?
H55 C9A H53 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_database_code_depnum_ccdc_archive 'CCDC 1022107'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_c:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 vanillic acid theobromine co-crystal dihydrate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N4 O8'
_chemical_formula_weight         384.35

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

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

_cell_length_a                   8.2148(16)
_cell_length_b                   8.2504(17)
_cell_length_c                   13.132(3)
_cell_angle_alpha                102.82(3)
_cell_angle_beta                 97.46(3)
_cell_angle_gamma                93.98(3)
_cell_volume                     856.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7070
_cell_measurement_theta_min      1.61
_cell_measurement_theta_max      27.13

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
  'SADABS; Sheldrick, 1996'   
;

_diffrn_ambient_temperature      173(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 Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            7070
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.13
_reflns_number_total             3767
_reflns_number_gt                2804
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'


_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)+(0.0595P)²+0.1568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3767
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.22071(15) 0.19748(14) 0.60850(10) 0.0302(3) Uani 1 1 d . . .
C1 C 0.07437(18) -0.0109(2) 0.66930(13) 0.0221(3) Uani 1 1 d . . .
H1A H 0.284(3) 0.211(3) 0.5559(19) 0.056(7) Uiso 1 1 d . . .
H5 H -0.183(3) -0.279(3) 0.8808(19) 0.059(7) Uiso 1 1 d . . .
H6B H 0.064(4) 0.553(4) 0.884(2) 0.089(10) Uiso 1 1 d . . .
H6A H 0.217(3) 0.646(3) 0.876(2) 0.068(8) Uiso 1 1 d . . .
H5A H -0.235(3) -0.569(4) 0.851(2) 0.072(9) Uiso 1 1 d . . .
O2 O 0.20876(14) -0.06804(14) 0.51814(9) 0.0302(3) Uani 1 1 d . . .
C2 C 0.04348(19) 0.1037(2) 0.75802(13) 0.0244(3) Uani 1 1 d . . .
H2 H 0.0801 0.2189 0.7686 0.029 Uiso 1 1 calc R . .
O3 O -0.17755(15) -0.16967(16) 0.88890(10) 0.0308(3) Uani 1 1 d . . .
C3 C -0.04146(19) 0.0486(2) 0.83120(13) 0.0250(4) Uani 1 1 d . . .
H3 H -0.0618 0.1263 0.8922 0.030 Uiso 1 1 calc R . .
O4 O -0.13429(15) -0.39440(14) 0.71517(9) 0.0294(3) Uani 1 1 d . . .
C4 C -0.09641(18) -0.1188(2) 0.81547(13) 0.0232(3) Uani 1 1 d . . .
O5 O -0.17947(16) -0.49412(16) 0.90195(12) 0.0324(3) Uani 1 1 d . . .
C5 C -0.07006(18) -0.23358(19) 0.72391(13) 0.0220(3) Uani 1 1 d . . .
H5B H -0.184(3) -0.524(3) 0.9588(19) 0.047(7) Uiso 1 1 d . . .
O6 O 0.16858(18) 0.56627(18) 0.90179(12) 0.0396(3) Uani 1 1 d . . .
H17 H 0.334(3) -0.029(2) 0.4113(17) 0.041(6) Uiso 1 1 d . . .
C6 C 0.01607(18) -0.17986(19) 0.65196(12) 0.0218(3) Uani 1 1 d . . .
H6 H 0.0358 -0.2574 0.5907 0.026 Uiso 1 1 calc R . .
O7 O 0.36558(14) -0.26315(13) 0.26350(9) 0.0269(3) Uani 1 1 d . . .
C7 C -0.1118(2) -0.5177(2) 0.62399(15) 0.0334(4) Uani 1 1 d . . .
H7A H -0.1558 -0.4829 0.5601 0.050 Uiso 1 1 calc R . .
H7C H -0.1702 -0.6249 0.6249 0.050 Uiso 1 1 calc R . .
H7B H 0.0062 -0.5297 0.6245 0.050 Uiso 1 1 calc R . .
O8 O 0.40014(14) 0.26631(14) 0.46665(9) 0.0286(3) Uani 1 1 d . . .
C8 C 0.17266(18) 0.0358(2) 0.59157(13) 0.0226(3) Uani 1 1 d . . .
C9 C 0.41773(18) -0.11592(19) 0.27560(12) 0.0203(3) Uani 1 1 d . . .
C10 C 0.50911(18) -0.04254(19) 0.20931(12) 0.0212(3) Uani 1 1 d . . .
N11 N 0.57288(16) -0.11005(16) 0.11833(11) 0.0226(3) Uani 1 1 d . . .
C12 C 0.65142(19) 0.0183(2) 0.09171(13) 0.0244(4) Uani 1 1 d . . .
H12 H 0.7075 0.0053 0.0320 0.029 Uiso 1 1 calc R . .
N13 N 0.64407(16) 0.16594(16) 0.15637(11) 0.0231(3) Uani 1 1 d . . .
C14 C 0.55635(18) 0.12565(19) 0.22978(12) 0.0205(3) Uani 1 1 d . . .
N15 N 0.51808(16) 0.23667(16) 0.31670(11) 0.0227(3) Uani 1 1 d . . .
C16 C 0.43531(18) 0.17438(19) 0.38623(13) 0.0217(3) Uani 1 1 d . . .
N17 N 0.39130(16) 0.00445(16) 0.36279(11) 0.0225(3) Uani 1 1 d . . .
C18 C 0.5645(2) 0.4168(2) 0.33443(15) 0.0316(4) Uani 1 1 d . . .
H18B H 0.4948 0.4618 0.2831 0.047 Uiso 1 1 calc R . .
H18C H 0.6805 0.4364 0.3259 0.047 Uiso 1 1 calc R . .
H18A H 0.5492 0.4727 0.4061 0.047 Uiso 1 1 calc R . .
C19 C 0.5638(2) -0.2866(2) 0.06579(14) 0.0302(4) Uani 1 1 d . . .
H19C H 0.6266 -0.2995 0.0065 0.045 Uiso 1 1 calc R . .
H19B H 0.4482 -0.3298 0.0395 0.045 Uiso 1 1 calc R . .
H19A H 0.6103 -0.3490 0.1161 0.045 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 C8 1.3257(19) . ?
O1 H1A 0.94(3) . ?
C1 C2 1.392(2) . ?
C1 C6 1.401(2) . ?
C1 C8 1.479(2) . ?
O2 C8 1.2225(19) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
O3 C4 1.363(2) . ?
O3 H5 0.88(3) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
O4 C5 1.3681(19) . ?
O4 C7 1.430(2) . ?
C4 C5 1.407(2) . ?
O5 H5A 0.86(3) . ?
O5 H5B 0.84(2) . ?
C5 C6 1.380(2) . ?
O6 H6B 0.85(3) . ?
O6 H6A 0.90(3) . ?
C6 H6 0.9500 . ?
O7 C9 1.2283(19) . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
O8 C16 1.2362(19) . ?
C9 N17 1.391(2) . ?
C9 C10 1.424(2) . ?
C10 C14 1.372(2) . ?
C10 N11 1.385(2) . ?
N11 C12 1.337(2) . ?
N11 C19 1.459(2) . ?
C12 N13 1.332(2) . ?
C12 H12 0.9500 . ?
N13 C14 1.360(2) . ?
C14 N15 1.382(2) . ?
N15 C16 1.372(2) . ?
N15 C18 1.468(2) . ?
C16 N17 1.378(2) . ?
N17 H17 0.92(2) . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18A 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19A 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
C8 O1 H1A 107.3(14) . . ?
C2 C1 C6 120.24(15) . . ?
C2 C1 C8 122.89(14) . . ?
C6 C1 C8 116.85(14) . . ?
C1 C2 C3 119.59(15) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 O3 H5 111.6(16) . . ?
C4 C3 C2 120.35(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 O4 C7 117.76(13) . . ?
O3 C4 C3 119.14(15) . . ?
O3 C4 C5 120.88(15) . . ?
C3 C4 C5 119.97(15) . . ?
H5A O5 H5B 109(2) . . ?
O4 C5 C6 125.35(14) . . ?
O4 C5 C4 114.83(14) . . ?
C6 C5 C4 119.83(15) . . ?
H6B O6 H6A 112(3) . . ?
C5 C6 C1 119.97(15) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
O2 C8 O1 122.70(15) . . ?
O2 C8 C1 122.18(14) . . ?
O1 C8 C1 115.11(14) . . ?
O7 C9 N17 121.06(15) . . ?
O7 C9 C10 128.27(15) . . ?
N17 C9 C10 110.67(13) . . ?
C14 C10 N11 104.73(14) . . ?
C14 C10 C9 122.81(15) . . ?
N11 C10 C9 132.44(14) . . ?
C12 N11 C10 106.10(13) . . ?
C12 N11 C19 127.04(14) . . ?
C10 N11 C19 126.78(14) . . ?
N13 C12 N11 114.04(14) . . ?
N13 C12 H12 123.0 . . ?
N11 C12 H12 123.0 . . ?
C12 N13 C14 102.95(13) . . ?
N13 C14 C10 112.17(14) . . ?
N13 C14 N15 125.66(14) . . ?
C10 C14 N15 122.16(14) . . ?
C16 N15 C14 118.34(13) . . ?
C16 N15 C18 120.65(14) . . ?
C14 N15 C18 121.01(13) . . ?
O8 C16 N15 121.69(14) . . ?
O8 C16 N17 120.88(14) . . ?
N15 C16 N17 117.43(14) . . ?
C16 N17 C9 128.50(14) . . ?
C16 N17 H17 113.1(13) . . ?
C9 N17 H17 118.3(13) . . ?
N15 C18 H18B 109.5 . . ?
N15 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N15 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
N11 C19 H19C 109.5 . . ?
N11 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
N11 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
H19B C19 H19A 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
C6 C1 C2 C3 1.9(2) . . . . ?
C8 C1 C2 C3 -176.02(14) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 O3 179.26(15) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C7 O4 C5 C6 -0.4(2) . . . . ?
C7 O4 C5 C4 -179.91(14) . . . . ?
O3 C4 C5 O4 1.2(2) . . . . ?
C3 C4 C5 O4 -177.97(13) . . . . ?
O3 C4 C5 C6 -178.37(14) . . . . ?
C3 C4 C5 C6 2.5(2) . . . . ?
O4 C5 C6 C1 179.32(14) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C8 C1 C6 C5 177.04(14) . . . . ?
C2 C1 C8 O2 174.67(15) . . . . ?
C6 C1 C8 O2 -3.4(2) . . . . ?
C2 C1 C8 O1 -4.3(2) . . . . ?
C6 C1 C8 O1 177.72(13) . . . . ?
O7 C9 C10 C14 177.92(15) . . . . ?
N17 C9 C10 C14 -2.3(2) . . . . ?
O7 C9 C10 N11 -3.9(3) . . . . ?
N17 C9 C10 N11 175.87(15) . . . . ?
C14 C10 N11 C12 0.08(16) . . . . ?
C9 C10 N11 C12 -178.36(16) . . . . ?
C14 C10 N11 C19 177.01(15) . . . . ?
C9 C10 N11 C19 -1.4(3) . . . . ?
C10 N11 C12 N13 -0.71(18) . . . . ?
C19 N11 C12 N13 -177.63(15) . . . . ?
N11 C12 N13 C14 1.02(17) . . . . ?
C12 N13 C14 C10 -0.95(17) . . . . ?
C12 N13 C14 N15 178.34(14) . . . . ?
N11 C10 C14 N13 0.56(17) . . . . ?
C9 C10 C14 N13 179.18(14) . . . . ?
N11 C10 C14 N15 -178.76(13) . . . . ?
C9 C10 C14 N15 -0.1(2) . . . . ?
N13 C14 N15 C16 -176.81(14) . . . . ?
C10 C14 N15 C16 2.4(2) . . . . ?
N13 C14 N15 C18 3.2(2) . . . . ?
C10 C14 N15 C18 -177.55(15) . . . . ?
C14 N15 C16 O8 178.54(14) . . . . ?
C18 N15 C16 O8 -1.5(2) . . . . ?
C14 N15 C16 N17 -1.9(2) . . . . ?
C18 N15 C16 N17 178.06(14) . . . . ?
O8 C16 N17 C9 178.63(14) . . . . ?
N15 C16 N17 C9 -0.9(2) . . . . ?
O7 C9 N17 C16 -177.27(14) . . . . ?
C10 C9 N17 C16 3.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_database_code_depnum_ccdc_archive 'CCDC 1022108'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_d:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 vanillic acid acridine co-crystal 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.4690(17)
_cell_length_b                   22.621(5)
_cell_length_c                   8.9534(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.68(3)
_cell_angle_gamma                90.00
_cell_volume                     1715.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8330
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.53

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 'SADABS; Sheldrick, 1996'  
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            8132
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3933
_reflns_number_gt                2217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0545P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3933
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 0.13993(16) 0.11541(7) 0.80078(15) 0.0363(4) Uani 1 1 d D . .
C1 C 0.2374(2) 0.19018(9) 0.96054(19) 0.0251(4) Uani 1 1 d . . .
O2 O 0.40053(15) 0.12137(6) 0.83344(14) 0.0317(4) Uani 1 1 d . . .
C2 C 0.3632(2) 0.21992(10) 1.0255(2) 0.0295(5) Uani 1 1 d . . .
H2 H 0.4679 0.2089 1.0008 0.035 Uiso 1 1 calc R . .
O3 O 0.16848(16) 0.32499(7) 1.26699(14) 0.0297(3) Uani 1 1 d . . .
C3 C 0.3393(2) 0.26544(10) 1.1259(2) 0.0314(5) Uani 1 1 d . . .
H3 H 0.4271 0.2856 1.1687 0.038 Uiso 1 1 calc R . .
O4 O -0.08422(14) 0.27264(7) 1.14267(15) 0.0380(4) Uani 1 1 d . . .
C4 C 0.1879(2) 0.28150(9) 1.16392(19) 0.0249(4) Uani 1 1 d . . .
C5 C 0.0597(2) 0.25244(9) 1.09706(19) 0.0255(5) Uani 1 1 d . . .
H5 H 0.064(3) 0.3344(14) 1.282(3) 0.082(9) Uiso 1 1 d . . .
C6 C 0.0841(2) 0.20773(9) 0.99612(19) 0.0255(4) Uani 1 1 d . . .
H6 H -0.0038 0.1886 0.9502 0.031 Uiso 1 1 calc R . .
C7 C -0.2210(2) 0.24826(13) 1.0734(3) 0.0546(8) Uani 1 1 d . . .
H7A H -0.2164 0.2546 0.9652 0.082 Uiso 1 1 calc R . .
H7B H -0.3153 0.2675 1.1129 0.082 Uiso 1 1 calc R . .
H7C H -0.2257 0.2058 1.0941 0.082 Uiso 1 1 calc R . .
C8 C 0.2663(2) 0.13949(10) 0.8586(2) 0.0269(5) Uani 1 1 d . . .
N9 N 0.20754(18) 0.03467(8) 0.61138(17) 0.0302(4) Uani 1 1 d . . .
C10 C 0.3012(2) -0.01204(10) 0.6450(2) 0.0301(5) Uani 1 1 d . . .
C11 C 0.3479(2) -0.02217(11) 0.7958(2) 0.0377(5) Uani 1 1 d . . .
H11 H 0.3137 0.0038 0.8722 0.045 Uiso 1 1 calc R . .
C12 C 0.4417(3) -0.06909(12) 0.8306(3) 0.0464(6) Uani 1 1 d . . .
H12 H 0.4710 -0.0761 0.9319 0.056 Uiso 1 1 calc R . .
C13 C 0.4962(3) -0.10766(12) 0.7179(3) 0.0504(6) Uani 1 1 d . . .
H13 H 0.5629 -0.1399 0.7441 0.060 Uiso 1 1 calc R . .
C14 C 0.4541(3) -0.09908(11) 0.5733(3) 0.0433(6) Uani 1 1 d . . .
H14 H 0.4923 -0.1252 0.4989 0.052 Uiso 1 1 calc R . .
C15 C 0.3534(2) -0.05133(10) 0.5310(2) 0.0336(5) Uani 1 1 d . . .
C16 C 0.3042(2) -0.04117(10) 0.3852(2) 0.0377(5) Uani 1 1 d . . .
H16 H 0.3381 -0.0669 0.3080 0.045 Uiso 1 1 calc R . .
C17 C 0.2059(2) 0.00602(10) 0.3504(2) 0.0342(5) Uani 1 1 d . . .
C18 C 0.1502(3) 0.01906(12) 0.2026(2) 0.0443(6) Uani 1 1 d . . .
H18 H 0.1785 -0.0062 0.1225 0.053 Uiso 1 1 calc R . .
C19 C 0.0590(3) 0.06630(13) 0.1750(2) 0.0485(7) Uani 1 1 d . . .
H19 H 0.0236 0.0743 0.0759 0.058 Uiso 1 1 calc R . .
C20 C 0.0150(3) 0.10435(12) 0.2932(2) 0.0467(6) Uani 1 1 d . . .
H20 H -0.0490 0.1379 0.2722 0.056 Uiso 1 1 calc R . .
C21 C 0.0626(2) 0.09378(11) 0.4357(2) 0.0388(6) Uani 1 1 d . . .
H21 H 0.0307 0.1195 0.5135 0.047 Uiso 1 1 calc R . .
C22 C 0.1600(2) 0.04436(10) 0.4691(2) 0.0314(5) Uani 1 1 d . . .
H1A H 0.172(3) 0.0844(10) 0.733(3) 0.102(11) 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
O1 C8 1.303(2) . ?
O1 H1A 0.9700(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.398(2) . ?
C1 C8 1.487(3) . ?
O2 C8 1.232(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
O3 C4 1.360(2) . ?
O3 H5 0.92(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
O4 C5 1.369(2) . ?
O4 C7 1.419(2) . ?
C4 C5 1.397(3) . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N9 C22 1.349(2) . ?
N9 C10 1.353(3) . ?
C10 C11 1.421(3) . ?
C10 C15 1.427(3) . ?
C11 C12 1.359(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.353(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.425(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C22 1.429(3) . ?
C17 C18 1.430(3) . ?
C18 C19 1.340(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.354(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.419(3) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1A 108.3(17) . . ?
C2 C1 C6 118.62(18) . . ?
C2 C1 C8 120.09(17) . . ?
C6 C1 C8 121.26(17) . . ?
C1 C2 C3 121.17(18) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 O3 H5 113.1(18) . . ?
C4 C3 C2 120.01(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 O4 C7 117.71(16) . . ?
O3 C4 C3 118.56(17) . . ?
O3 C4 C5 122.11(16) . . ?
C3 C4 C5 119.33(18) . . ?
O4 C5 C6 125.68(17) . . ?
O4 C5 C4 113.89(17) . . ?
C6 C5 C4 120.43(17) . . ?
C5 C6 C1 120.41(18) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O1 122.92(19) . . ?
O2 C8 C1 121.88(18) . . ?
O1 C8 C1 115.19(16) . . ?
C22 N9 C10 120.28(18) . . ?
N9 C10 C11 119.53(19) . . ?
N9 C10 C15 120.88(18) . . ?
C11 C10 C15 119.6(2) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 123.3(2) . . ?
C16 C15 C10 118.6(2) . . ?
C14 C15 C10 118.2(2) . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C22 117.91(19) . . ?
C16 C17 C18 123.8(2) . . ?
C22 C17 C18 118.2(2) . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
N9 C22 C21 119.55(19) . . ?
N9 C22 C17 121.5(2) . . ?
C21 C22 C17 118.94(19) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
_database_code_depnum_ccdc_archive 'CCDC 1022109'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_e:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 vanillic acid nicotinamide co-crystal
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_formula_weight         290.27

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

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

_cell_length_a                   4.8723(10)
_cell_length_b                   8.0058(16)
_cell_length_c                   18.018(4)
_cell_angle_alpha                78.85(3)
_cell_angle_beta                 84.50(3)
_cell_angle_gamma                75.62(3)
_cell_volume                     667.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5518
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.33

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 'SADABS; Sheldrick, 1996'  
;

_diffrn_ambient_temperature      173(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 Kappa Duo Apex II diffractometer'
_diffrn_reflns_number            5518
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.33
_reflns_number_total             3283
_reflns_number_gt                2355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0569P)²+0.1410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3283
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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 0.8171(2) 0.35403(15) 0.48724(6) 0.0290(3) Uani 1 1 d . . .
O4 O 1.7293(2) 0.14281(15) 0.32733(6) 0.0299(3) Uani 1 1 d . . .
O2 O 0.6206(2) 0.61168(15) 0.41689(7) 0.0302(3) Uani 1 1 d D . .
H1 H 0.4904 0.6075 0.4508 0.036 Uiso 1 1 calc RD . .
O3 O 1.6847(2) 0.38928(16) 0.20159(6) 0.0308(3) Uani 1 1 d . . .
C1 C 1.0540(3) 0.4495(2) 0.37117(8) 0.0224(3) Uani 1 1 d . . .
C5 C 1.4961(3) 0.2805(2) 0.32513(9) 0.0228(3) Uani 1 1 d . . .
C6 C 1.2808(3) 0.3018(2) 0.38096(9) 0.0237(3) Uani 1 1 d . . .
H6 H 1.2871 0.2164 0.4258 0.028 Uiso 1 1 calc R . .
C8 C 0.8189(3) 0.4709(2) 0.42934(8) 0.0225(3) Uani 1 1 d . . .
C4 C 1.4828(3) 0.4070(2) 0.25841(9) 0.0243(3) Uani 1 1 d . . .
C3 C 1.2591(3) 0.5521(2) 0.24951(9) 0.0291(4) Uani 1 1 d . . .
H3 H 1.2513 0.6373 0.2045 0.035 Uiso 1 1 calc R . .
C2 C 1.0449(3) 0.5746(2) 0.30576(9) 0.0272(4) Uani 1 1 d . . .
H2 H 0.8921 0.6755 0.2995 0.033 Uiso 1 1 calc R . .
C7 C 1.7604(4) 0.0129(2) 0.39460(11) 0.0378(4) Uani 1 1 d . . .
H7C H 1.7674 0.0680 0.4382 0.057 Uiso 1 1 calc R . .
H7A H 1.9364 -0.0765 0.3897 0.057 Uiso 1 1 calc R . .
H7B H 1.5986 -0.0420 0.4020 0.057 Uiso 1 1 calc R . .
O5 O 0.2087(2) 0.72686(17) 0.03836(7) 0.0333(3) Uani 1 1 d . . .
N6 N 0.6790(3) 0.63045(19) 0.05358(8) 0.0282(3) Uani 1 1 d . . .
N10 N 0.8265(3) 0.83770(19) -0.17572(8) 0.0307(3) Uani 1 1 d . . .
C10 C 0.4564(3) 0.7219(2) 0.01407(9) 0.0232(3) Uani 1 1 d . . .
C14 C 0.5193(3) 0.8177(2) -0.06304(9) 0.0228(3) Uani 1 1 d . . .
C13 C 0.3286(3) 0.9679(2) -0.09456(10) 0.0312(4) Uani 1 1 d . . .
H13 H 0.1568 1.0119 -0.0676 0.037 Uiso 1 1 calc R . .
C9 C 0.7645(3) 0.7586(2) -0.10603(9) 0.0285(4) Uani 1 1 d . . .
H9 H 0.8960 0.6556 -0.0845 0.034 Uiso 1 1 calc R . .
C11 C 0.6412(4) 0.9835(2) -0.20447(10) 0.0344(4) Uani 1 1 d . . .
H11 H 0.6820 1.0425 -0.2538 0.041 Uiso 1 1 calc R . .
C12 C 0.3935(4) 1.0525(3) -0.16605(11) 0.0396(4) Uani 1 1 d . . .
H12 H 0.2683 1.1573 -0.1885 0.048 Uiso 1 1 calc R . .
H6A H 0.8479 0.6504 0.0399 0.029(5) Uiso 1 1 d R . .
H6B H 0.6581 0.5625 0.1003 0.040(5) Uiso 1 1 d R . .
H15 H 1.8323 0.2937 0.2109 0.070(8) Uiso 1 1 d 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 C8 1.2605(19) . ?
O4 C5 1.3702(19) . ?
O4 C7 1.430(2) . ?
O2 C8 1.288(2) . ?
O2 H1 0.8400 . ?
O3 C4 1.3526(18) . ?
O3 H15 0.9116 . ?
C1 C2 1.387(2) . ?
C1 C6 1.399(2) . ?
C1 C8 1.477(2) . ?
C5 C6 1.384(2) . ?
C5 C4 1.409(2) . ?
C6 H6 0.9500 . ?
C4 C3 1.377(2) . ?
C3 C2 1.387(2) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
O5 C10 1.2376(18) . ?
N6 C10 1.331(2) . ?
N6 H6A 0.8802 . ?
N6 H6B 0.9214 . ?
N10 C11 1.333(2) . ?
N10 C9 1.336(2) . ?
C10 C14 1.495(2) . ?
C14 C13 1.384(2) . ?
C14 C9 1.391(2) . ?
C13 C12 1.381(3) . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O4 C7 117.29(13) . . ?
C8 O2 H1 109.5 . . ?
C4 O3 H15 115.2 . . ?
C2 C1 C6 120.12(14) . . ?
C2 C1 C8 119.57(14) . . ?
C6 C1 C8 120.28(14) . . ?
O4 C5 C6 125.91(14) . . ?
O4 C5 C4 114.51(13) . . ?
C6 C5 C4 119.58(14) . . ?
C5 C6 C1 119.86(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C8 O2 123.11(14) . . ?
O1 C8 C1 120.28(14) . . ?
O2 C8 C1 116.61(14) . . ?
O3 C4 C3 118.36(14) . . ?
O3 C4 C5 121.58(14) . . ?
C3 C4 C5 120.05(14) . . ?
C4 C3 C2 120.42(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C2 C1 119.96(15) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O4 C7 H7C 109.5 . . ?
O4 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C10 N6 H6A 119.8 . . ?
C10 N6 H6B 121.8 . . ?
H6A N6 H6B 117.3 . . ?
C11 N10 C9 117.02(15) . . ?
O5 C10 N6 122.69(15) . . ?
O5 C10 C14 120.76(14) . . ?
N6 C10 C14 116.54(13) . . ?
C13 C14 C9 117.79(15) . . ?
C13 C14 C10 120.23(14) . . ?
C9 C14 C10 121.97(14) . . ?
C12 C13 C14 118.57(16) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N10 C9 C14 124.06(15) . . ?
N10 C9 H9 118.0 . . ?
C14 C9 H9 118.0 . . ?
N10 C11 C12 123.10(16) . . ?
N10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C13 119.45(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl methylketone'
_database_code_depnum_ccdc_archive 'CCDC 1022110'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_f:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (bis)vanillic acid (bis)isonicotinamide dihydrate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H32 N4 O12'
_chemical_formula_weight         616.58

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

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

_cell_length_a                   7.9000(16)
_cell_length_b                   13.196(3)
_cell_length_c                   13.735(3)
_cell_angle_alpha                85.02(3)
_cell_angle_beta                 85.32(3)
_cell_angle_gamma                78.68(3)
_cell_volume                     1395.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12277
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.41

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ scans and ω scans'
_diffrn_reflns_number            12277
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.71
_reflns_number_total             6451
_reflns_number_gt                4137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0682P)²+0.2869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6451
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_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
O2 O 0.04597(18) 0.56791(10) 0.32459(9) 0.0403(3) Uani 1 1 d . . .
O17A O -0.12231(18) 0.85845(10) 0.05113(9) 0.0401(3) Uani 1 1 d . . .
O4 O 0.41472(18) 0.64011(10) 0.67384(9) 0.0387(3) Uani 1 1 d . . .
O1 O 0.18003(17) 0.44947(9) 0.43308(9) 0.0379(3) Uani 1 1 d . . .
N9A N -0.2631(2) 0.52251(12) -0.01570(11) 0.0356(4) Uani 1 1 d . . .
O3 O 0.34895(18) 0.83317(10) 0.61267(10) 0.0403(3) Uani 1 1 d . . .
N16A N -0.0359(2) 0.76297(12) 0.18823(11) 0.0365(4) Uani 1 1 d . . .
C3 C 0.1945(2) 0.79961(14) 0.47806(14) 0.0362(5) Uani 1 1 d . . .
H3 H 0.1670 0.8712 0.4574 0.043 Uiso 1 1 calc R . .
C12A C -0.1554(2) 0.68355(14) 0.06335(13) 0.0300(4) Uani 1 1 d . . .
C11A C -0.2364(2) 0.69904(14) -0.02341(13) 0.0349(4) Uani 1 1 d . . .
H11A H -0.2574 0.7658 -0.0571 0.042 Uiso 1 1 calc R . .
C1 C 0.1801(2) 0.62297(14) 0.45546(13) 0.0314(4) Uani 1 1 d . . .
C8 C 0.1275(2) 0.54548(14) 0.39796(13) 0.0316(4) Uani 1 1 d . . .
C6 C 0.2734(2) 0.59078(14) 0.53877(13) 0.0317(4) Uani 1 1 d . . .
H6 H 0.3002 0.5192 0.5597 0.038 Uiso 1 1 calc R . .
C10A C -0.2869(2) 0.61669(15) -0.06101(14) 0.0368(5) Uani 1 1 d . . .
H10A H -0.3405 0.6279 -0.1215 0.044 Uiso 1 1 calc R . .
C13A C -0.1305(3) 0.58546(14) 0.11041(14) 0.0353(4) Uani 1 1 d . . .
H13A H -0.0757 0.5718 0.1705 0.042 Uiso 1 1 calc R . .
C7 C 0.4551(3) 0.53422(15) 0.70886(15) 0.0422(5) Uani 1 1 d . . .
H7B H 0.3478 0.5082 0.7260 0.063 Uiso 1 1 calc R . .
H7A H 0.5217 0.5276 0.7670 0.063 Uiso 1 1 calc R . .
H7C H 0.5237 0.4938 0.6577 0.063 Uiso 1 1 calc R . .
C4 C 0.2887(2) 0.76777(14) 0.55922(13) 0.0323(4) Uani 1 1 d . . .
C5 C 0.3265(2) 0.66266(14) 0.59060(13) 0.0309(4) Uani 1 1 d . . .
C2 C 0.1400(2) 0.72739(14) 0.42669(14) 0.0354(4) Uani 1 1 d . . .
H2 H 0.0745 0.7499 0.3712 0.042 Uiso 1 1 calc R . .
C15A C -0.1020(2) 0.77553(14) 0.10148(13) 0.0319(4) Uani 1 1 d . . .
C14A C -0.1868(3) 0.50762(15) 0.06842(13) 0.0371(5) Uani 1 1 d . . .
H14A H -0.1701 0.4404 0.1012 0.045 Uiso 1 1 calc R . .
O4A O 0.41149(18) 0.17863(10) 0.65922(9) 0.0388(3) Uani 1 1 d . . .
O2A O 0.72457(18) 0.26861(10) 1.02171(9) 0.0415(3) Uani 1 1 d . . .
O1A O 0.64975(18) 0.37775(10) 0.89270(9) 0.0406(3) Uani 1 1 d . . .
O3A O 0.44593(18) -0.00874(10) 0.73660(10) 0.0422(4) Uani 1 1 d . . .
C4A C 0.5048(2) 0.05832(14) 0.78839(14) 0.0334(4) Uani 1 1 d . . .
C6A C 0.6338(2) 0.10566(14) 0.92590(14) 0.0343(4) Uani 1 1 d . . .
H6A H 0.6836 0.0869 0.9871 0.041 Uiso 1 1 calc R . .
C5A C 0.5794(2) 0.03172(14) 0.87647(14) 0.0357(4) Uani 1 1 d . . .
H5A H 0.5938 -0.0379 0.9036 0.043 Uiso 1 1 calc R . .
C1A C 0.6152(2) 0.20683(14) 0.88578(13) 0.0313(4) Uani 1 1 d . . .
C2A C 0.5426(2) 0.23402(14) 0.79532(13) 0.0325(4) Uani 1 1 d . . .
H2A H 0.5316 0.3032 0.7672 0.039 Uiso 1 1 calc R . .
C8A C 0.6689(2) 0.28614(14) 0.93984(13) 0.0330(4) Uani 1 1 d . . .
C3A C 0.4868(2) 0.16059(14) 0.74686(13) 0.0318(4) Uani 1 1 d . . .
C7A C 0.3698(3) 0.28352(14) 0.62007(14) 0.0400(5) Uani 1 1 d . . .
H40A H 0.2964 0.3254 0.6686 0.060 Uiso 1 1 calc R . .
H40B H 0.3077 0.2867 0.5606 0.060 Uiso 1 1 calc R . .
H40C H 0.4765 0.3106 0.6041 0.060 Uiso 1 1 calc R . .
O5 O 0.47195(19) 0.79781(10) 0.81162(10) 0.0427(4) Uani 1 1 d . . .
O6 O 0.23621(19) 0.03373(10) 0.56777(10) 0.0426(4) Uani 1 1 d . . .
N9 N 0.1289(2) 0.29587(12) 0.33637(11) 0.0351(4) Uani 1 1 d . . .
O17 O 0.01160(18) -0.04809(10) 0.27126(9) 0.0386(3) Uani 1 1 d . . .
C12 C 0.0486(2) 0.12671(14) 0.25580(13) 0.0315(4) Uani 1 1 d . . .
C11 C -0.0170(2) 0.22659(14) 0.21982(14) 0.0347(4) Uani 1 1 d . . .
H11 H -0.0891 0.2388 0.1663 0.042 Uiso 1 1 calc R . .
N16 N -0.0438(2) 0.04144(12) 0.12625(11) 0.0389(4) Uani 1 1 d . . .
C14 C 0.1938(3) 0.19950(15) 0.36969(14) 0.0388(5) Uani 1 1 d . . .
H14 H 0.2697 0.1896 0.4214 0.047 Uiso 1 1 calc R . .
C13 C 0.1560(3) 0.11320(15) 0.33258(14) 0.0371(5) Uani 1 1 d . . .
H13 H 0.2028 0.0456 0.3593 0.045 Uiso 1 1 calc R . .
C15 C 0.0041(2) 0.03261(14) 0.21739(13) 0.0321(4) Uani 1 1 d . . .
C10 C 0.0247(2) 0.30845(14) 0.26331(13) 0.0362(4) Uani 1 1 d . . .
H10 H -0.0237 0.3770 0.2398 0.043 Uiso 1 1 calc R . .
H16B H -0.0755 -0.0176 0.0956 0.062(7) Uiso 1 1 d R . .
H16D H -0.0065 0.8204 0.2197 0.052(6) Uiso 1 1 d R . .
H5 H 0.3125 0.9071 0.5870 0.085(9) Uiso 1 1 d R . .
H1A H 0.1613 0.3942 0.3877 0.064(7) Uiso 1 1 d R . .
H5B H 0.4708 -0.0787 0.7776 0.090(9) Uiso 1 1 d R . .
H16C H -0.0087 0.6969 0.2249 0.050(6) Uiso 1 1 d R . .
H16A H -0.0394 0.1007 0.0796 0.056(7) Uiso 1 1 d R . .
H5D H 0.4463 0.7635 0.7633 0.065(7) Uiso 1 1 d R . .
H6C H 0.1385 0.0416 0.6178 0.086(9) Uiso 1 1 d R . .
H5C H 0.4001 0.7771 0.8651 0.112(12) Uiso 1 1 d R . .
H6D H 0.3000 0.0641 0.6034 0.080(9) Uiso 1 1 d R . .
H1B H 0.6853 0.4359 0.9281 0.084(8) Uiso 1 1 d 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
O2 C8 1.224(2) . ?
O17A C15A 1.233(2) . ?
O4 C5 1.368(2) . ?
O4 C7 1.421(2) . ?
O1 C8 1.315(2) . ?
N9A C10A 1.327(2) . ?
N9A C14A 1.329(2) . ?
O3 C4 1.356(2) . ?
N16A C15A 1.324(2) . ?
C3 C4 1.380(3) . ?
C3 C2 1.385(2) . ?
C12A C11A 1.379(2) . ?
C12A C13A 1.381(3) . ?
C12A C15A 1.507(2) . ?
C11A C10A 1.381(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.401(2) . ?
C1 C8 1.484(2) . ?
C6 C5 1.380(2) . ?
C13A C14A 1.382(2) . ?
C4 C5 1.398(3) . ?
O4A C3A 1.368(2) . ?
O4A C7A 1.426(2) . ?
O2A C8A 1.227(2) . ?
O1A C8A 1.308(2) . ?
O3A C4A 1.353(2) . ?
C4A C5A 1.377(2) . ?
C4A C3A 1.404(3) . ?
C6A C1A 1.384(3) . ?
C6A C5A 1.387(2) . ?
C1A C2A 1.400(2) . ?
C1A C8A 1.479(2) . ?
C2A C3A 1.379(2) . ?
N9 C10 1.328(2) . ?
N9 C14 1.331(2) . ?
O17 C15 1.237(2) . ?
C12 C11 1.382(3) . ?
C12 C13 1.384(2) . ?
C12 C15 1.503(2) . ?
C11 C10 1.384(2) . ?
N16 C15 1.326(2) . ?
C14 C13 1.380(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
C5 O4 C7 117.06(14) . . ?
C10A N9A C14A 118.28(16) . . ?
C4 C3 C2 120.10(17) . . ?
C11A C12A C13A 118.13(16) . . ?
C11A C12A C15A 117.69(16) . . ?
C13A C12A C15A 124.18(16) . . ?
C12A C11A C10A 119.49(17) . . ?
C2 C1 C6 119.28(16) . . ?
C2 C1 C8 120.46(16) . . ?
C6 C1 C8 120.25(16) . . ?
O2 C8 O1 123.15(16) . . ?
O2 C8 C1 123.82(16) . . ?
O1 C8 C1 113.02(15) . . ?
C5 C6 C1 120.20(17) . . ?
N9A C10A C11A 122.35(17) . . ?
C12A C13A C14A 118.71(17) . . ?
O3 C4 C3 123.82(16) . . ?
O3 C4 C5 116.27(15) . . ?
C3 C4 C5 119.91(16) . . ?
O4 C5 C6 125.07(16) . . ?
O4 C5 C4 115.07(15) . . ?
C6 C5 C4 119.86(16) . . ?
C1 C2 C3 120.62(17) . . ?
O17A C15A N16A 123.18(16) . . ?
O17A C15A C12A 118.87(15) . . ?
N16A C15A C12A 117.94(16) . . ?
N9A C14A C13A 123.03(17) . . ?
C3A O4A C7A 117.42(14) . . ?
O3A C4A C5A 124.16(16) . . ?
O3A C4A C3A 115.94(16) . . ?
C5A C4A C3A 119.90(16) . . ?
C1A C6A C5A 119.81(16) . . ?
C4A C5A C6A 120.60(17) . . ?
C6A C1A C2A 119.92(16) . . ?
C6A C1A C8A 119.72(16) . . ?
C2A C1A C8A 120.35(16) . . ?
C3A C2A C1A 120.14(17) . . ?
O2A C8A O1A 122.77(17) . . ?
O2A C8A C1A 123.55(17) . . ?
O1A C8A C1A 113.68(15) . . ?
O4A C3A C2A 125.22(16) . . ?
O4A C3A C4A 115.16(15) . . ?
C2A C3A C4A 119.62(16) . . ?
C10 N9 C14 117.85(15) . . ?
C11 C12 C13 118.34(17) . . ?
C11 C12 C15 122.91(16) . . ?
C13 C12 C15 118.72(16) . . ?
C12 C11 C10 118.64(17) . . ?
N9 C14 C13 122.98(17) . . ?
C14 C13 C12 118.93(18) . . ?
O17 C15 N16 123.19(16) . . ?
O17 C15 C12 119.49(16) . . ?
N16 C15 C12 117.32(16) . . ?
N9 C10 C11 123.22(17) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.71
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053

# start Validation Reply Form
_vrf_PLAT417_c_                  
;
PROBLEM: Short Inter D-H..H-D H5 .. H6C .. 2.07 Ang.
RESPONSE: A water molecule with hydrogens H6C and H6D 
          is hydrogen bonded to the hydroxyl of VA (H5).
          The hydrogens are not directed towards each
          other.
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_database_code_depnum_ccdc_archive 'CCDC 1022111'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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.
#
data_g:

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (bis) vanillic acid (bis) urea 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N4 O10'
_chemical_formula_weight         456.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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

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

_cell_length_a                   6.9821(14)
_cell_length_b                   10.232(2)
_cell_length_c                   15.388(3)
_cell_angle_alpha                99.68(3)
_cell_angle_beta                 95.37(3)
_cell_angle_gamma                103.46(3)
_cell_volume                     1043.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11587
_cell_measurement_theta_min      1.36
_cell_measurement_theta_max      26.74

_exptl_crystal_description       rectangle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_reflns_number            11587
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         26.74
_reflns_number_total             4411
_reflns_number_gt                2844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4411
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
O5 O 0.38265(18) 0.34046(14) 0.35346(8) 0.0260(3) Uani 1 1 d . . .
O6 O 0.86956(18) 0.30899(14) 0.34001(8) 0.0260(3) Uani 1 1 d . . .
N9 N 0.4766(2) 0.20098(18) 0.24427(11) 0.0292(4) Uani 1 1 d . . .
N11 N 0.1509(2) 0.20983(18) 0.23958(11) 0.0298(4) Uani 1 1 d . . .
N14 N 0.7292(2) 0.3047(2) 0.46659(11) 0.0345(5) Uani 1 1 d . . .
N12 N 1.0619(2) 0.31074(19) 0.46741(11) 0.0310(4) Uani 1 1 d . . .
C10 C 0.3391(3) 0.2541(2) 0.28164(13) 0.0238(4) Uani 1 1 d . . .
C13 C 0.8865(3) 0.3090(2) 0.42333(13) 0.0239(4) Uani 1 1 d . . .
O2A O 0.2175(2) 0.97503(15) 0.08087(9) 0.0328(4) Uani 1 1 d . . .
O1 O 0.3261(2) 1.12841(15) -0.03469(9) 0.0391(4) Uani 1 1 d . . .
O2 O 0.24538(19) 0.93177(14) -0.13416(9) 0.0289(3) Uani 1 1 d . . .
O1A O 0.1345(2) 0.77561(15) -0.01637(9) 0.0343(4) Uani 1 1 d . . .
O4A O 0.1206(2) 0.83173(14) 0.37891(9) 0.0343(4) Uani 1 1 d . . .
O4 O 0.5428(2) 1.50493(14) -0.20003(9) 0.0344(4) Uani 1 1 d . . .
O3 O 0.4968(2) 1.37966(16) -0.37259(9) 0.0345(4) Uani 1 1 d . . .
O3A O -0.0177(2) 0.57251(16) 0.34286(9) 0.0382(4) Uani 1 1 d . . .
C3 C 0.4736(3) 1.3649(2) -0.21884(13) 0.0245(5) Uani 1 1 d . . .
C1 C 0.3566(3) 1.1423(2) -0.18364(12) 0.0230(4) Uani 1 1 d . . .
C1A C 0.1036(3) 0.7709(2) 0.13479(12) 0.0227(4) Uani 1 1 d . . .
C2 C 0.4269(3) 1.2843(2) -0.15691(12) 0.0240(5) Uani 1 1 d . . .
H2 H 0.4426 1.3254 -0.0957 0.029 Uiso 1 1 calc R . .
C6A C 0.1359(3) 0.8426(2) 0.22264(13) 0.0245(5) Uani 1 1 d . . .
H6A H 0.1873 0.9393 0.2354 0.029 Uiso 1 1 calc R . .
C8 C 0.3050(3) 1.0580(2) -0.11664(13) 0.0250(5) Uani 1 1 d . . .
C4A C 0.0182(3) 0.6302(2) 0.27157(13) 0.0267(5) Uani 1 1 d . . .
C8A C 0.1553(3) 0.8488(2) 0.06482(13) 0.0243(5) Uani 1 1 d . . .
C4 C 0.4512(3) 1.3047(2) -0.30929(13) 0.0255(5) Uani 1 1 d . . .
C2A C 0.0278(3) 0.6299(2) 0.11622(13) 0.0277(5) Uani 1 1 d . . .
H2A H 0.0041 0.5812 0.0564 0.033 Uiso 1 1 calc R . .
C5A C 0.0937(3) 0.7739(2) 0.29070(12) 0.0248(5) Uani 1 1 d . . .
C5 C 0.3822(3) 1.1637(2) -0.33523(13) 0.0277(5) Uani 1 1 d . . .
H5 H 0.3673 1.1223 -0.3964 0.033 Uiso 1 1 calc R . .
C6 C 0.3349(3) 1.0826(2) -0.27289(13) 0.0262(5) Uani 1 1 d . . .
H6 H 0.2875 0.9860 -0.2913 0.031 Uiso 1 1 calc R . .
C3A C -0.0135(3) 0.5597(2) 0.18462(13) 0.0279(5) Uani 1 1 d . . .
H3A H -0.0637 0.4629 0.1716 0.034 Uiso 1 1 calc R . .
C7 C 0.5772(3) 1.5706(2) -0.10855(13) 0.0368(6) Uani 1 1 d . . .
H7C H 0.4508 1.5570 -0.0842 0.055 Uiso 1 1 calc R . .
H7A H 0.6358 1.6689 -0.1033 0.055 Uiso 1 1 calc R . .
H7B H 0.6686 1.5311 -0.0753 0.055 Uiso 1 1 calc R . .
C7A C 0.1838(3) 0.9779(2) 0.40228(14) 0.0407(6) Uani 1 1 d . . .
H40C H 0.3156 1.0094 0.3848 0.061 Uiso 1 1 calc R . .
H40A H 0.1905 1.0070 0.4667 0.061 Uiso 1 1 calc R . .
H40B H 0.0888 1.0174 0.3714 0.061 Uiso 1 1 calc R . .
H11B H 0.0553 0.2348 0.2653 0.028(6) Uiso 1 1 d R . .
H9B H 0.4470 0.1367 0.1938 0.034(6) Uiso 1 1 d R . .
H11A H 0.1267 0.1497 0.1906 0.033(6) Uiso 1 1 d R . .
H9A H 0.5965 0.2337 0.2677 0.040(7) Uiso 1 1 d R . .
H12A H 1.1658 0.3295 0.4392 0.052(8) Uiso 1 1 d R . .
H12B H 1.0778 0.3241 0.5258 0.038(6) Uiso 1 1 d R . .
H14B H 0.6195 0.3186 0.4375 0.041(6) Uiso 1 1 d R . .
H13A H -0.0601 0.4924 0.3311 0.052(8) Uiso 1 1 d R . .
H13 H 0.5394 1.4631 -0.3509 0.065(9) Uiso 1 1 d R . .
H14A H 0.7412 0.3098 0.5244 0.046(7) Uiso 1 1 d R . .
H1B H 0.1725 0.8361 -0.0556 0.076(9) Uiso 1 1 d R . .
H1A H 0.2860 1.0677 0.0075 0.084(10) Uiso 1 1 d 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
O5 C10 1.257(2) . ?
O6 C13 1.276(2) . ?
N9 C10 1.338(2) . ?
N11 C10 1.348(2) . ?
N14 C13 1.332(3) . ?
N12 C13 1.338(2) . ?
O2A C8A 1.237(2) . ?
O1 C8 1.319(2) . ?
O2 C8 1.236(2) . ?
O1A C8A 1.320(2) . ?
O4A C5A 1.363(2) . ?
O4A C7A 1.429(2) . ?
O4 C3 1.372(2) . ?
O4 C7 1.427(2) . ?
O3 C4 1.354(2) . ?
O3A C4A 1.347(2) . ?
C3 C2 1.375(3) . ?
C3 C4 1.403(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.397(3) . ?
C1 C8 1.470(3) . ?
C1A C2A 1.386(3) . ?
C1A C6A 1.396(3) . ?
C1A C8A 1.467(3) . ?
C6A C5A 1.374(3) . ?
C4A C3A 1.381(3) . ?
C4A C5A 1.411(3) . ?
C4 C5 1.386(3) . ?
C2A C3A 1.386(3) . ?
C5 C6 1.385(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
O5 C10 N9 121.54(17) . . ?
O5 C10 N11 121.25(19) . . ?
N9 C10 N11 117.21(18) . . ?
O6 C13 N14 120.34(18) . . ?
O6 C13 N12 120.06(19) . . ?
N14 C13 N12 119.59(18) . . ?
C5A O4A C7A 117.21(16) . . ?
C3 O4 C7 117.02(16) . . ?
O4 C3 C2 125.11(18) . . ?
O4 C3 C4 114.77(18) . . ?
C2 C3 C4 120.11(18) . . ?
C6 C1 C2 119.73(19) . . ?
C6 C1 C8 120.76(18) . . ?
C2 C1 C8 119.50(18) . . ?
C2A C1A C6A 119.81(19) . . ?
C2A C1A C8A 122.08(18) . . ?
C6A C1A C8A 118.10(18) . . ?
C3 C2 C1 120.28(18) . . ?
C5A C6A C1A 120.25(19) . . ?
O2 C8 O1 121.76(19) . . ?
O2 C8 C1 123.79(18) . . ?
O1 C8 C1 114.45(18) . . ?
O3A C4A C3A 125.02(19) . . ?
O3A C4A C5A 115.16(18) . . ?
C3A C4A C5A 119.83(19) . . ?
O2A C8A O1A 121.89(19) . . ?
O2A C8A C1A 122.20(18) . . ?
O1A C8A C1A 115.90(18) . . ?
O3 C4 C5 118.48(18) . . ?
O3 C4 C3 122.26(18) . . ?
C5 C4 C3 119.25(19) . . ?
C1A C2A C3A 120.26(19) . . ?
O4A C5A C6A 125.83(19) . . ?
O4A C5A C4A 114.42(18) . . ?
C6A C5A C4A 119.74(18) . . ?
C6 C5 C4 120.64(19) . . ?
C1 C6 C5 119.98(19) . . ?
C4A C3A C2A 120.10(19) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049

######END OF CIF FILE#######




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_database_code_depnum_ccdc_archive 'CCDC 1022112'
