# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'P Cox'
_publ_contact_author_email       P.J.COX@RGU.AC.UK

_publ_section_title              
;
Supramolecular structures of some adenine-carboxylic
acid complexes
;
loop_
_publ_author_name
'P Cox'
'Maureen Byres'
'Graeme Kay'
'Elaine Nixon'

# Attachment 'accallcifs.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-02-12 at 14:48:53
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\cifdoc.dat
# CIF files read : 2d4d info struct

#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

data_adba
_database_code_depnum_ccdc_archive 'CCDC 686683'

_audit_creation_date             2008-02-12T16:18:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Adenine - benzoic acid (1:2) co-crystal
;
_chemical_formula_moiety         
;
C5 H5 N5, 2(C7 H6 O2)
;
_chemical_formula_sum            'C19 H17 N5 O4'
_chemical_formula_weight         379.38
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9422(2)
_cell_length_b                   10.1547(4)
_cell_length_c                   14.1896(5)
_cell_angle_alpha                81.003(2)
_cell_angle_beta                 76.327(2)
_cell_angle_gamma                70.344(2)
_cell_volume                     912.09(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4094
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.8606
_exptl_absorpt_correction_T_max  0.9881

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_number            19200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.2
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             4139
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0433P)²+0.2515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     288
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N1A N 0.6078(2) 0.77093(13) -0.02817(10) 0.0241(3) Uani 0.907(3) 1 d PD A 1
N2A N 0.8606(2) 0.88840(14) -0.03692(11) 0.0226(3) Uani 0.907(3) 1 d PD A 1
N3A N 0.53323(19) 0.93323(15) 0.19995(9) 0.0244(3) Uani 0.907(3) 1 d PD A 1
N4A N 0.8095(2) 0.99364(16) 0.11381(10) 0.0233(3) Uani 0.907(3) 1 d PD A 1
H4A H 0.911 1.0314 0.0992 0.028 Uiso 0.907(3) 1 calc PR A 1
N5A N 0.3375(3) 0.7678(3) 0.1037(2) 0.0257(5) Uani 0.907(3) 1 d PD A 1
H5A H 0.2931 0.7205 0.0713 0.031 Uiso 0.907(3) 1 calc PR A 1
H5B H 0.2704 0.7899 0.1628 0.031 Uiso 0.907(3) 1 calc PR A 1
C1A C 0.7731(2) 0.81316(15) -0.07136(12) 0.0244(3) Uani 0.907(3) 1 d PD A 1
H1A H 0.8363 0.7855 -0.1353 0.029 Uiso 0.907(3) 1 calc PR A 1
C2A C 0.7618(2) 0.91900(17) 0.05530(11) 0.0206(3) Uani 0.907(3) 1 d PD A 1
C3A C 0.5906(2) 0.88216(14) 0.10872(10) 0.0221(3) Uani 0.907(3) 1 d PD A 1
C4A C 0.5064(2) 0.80620(14) 0.06338(11) 0.0220(3) Uani 0.907(3) 1 d PD A 1
C5A C 0.6694(2) 0.99790(18) 0.19867(10) 0.0250(3) Uani 0.907(3) 1 d PD A 1
H5C H 0.6693 1.0434 0.2523 0.03 Uiso 0.907(3) 1 calc PR A 1
N1B N 0.492(2) 0.1165(14) -0.1920(9) 0.023(2) Uiso 0.093(3) 1 d PD A 2
N2B N 0.197(3) 0.0449(18) -0.1016(11) 0.023(2) Uiso 0.093(3) 1 d PD A 2
N3B N 0.331(2) 0.2135(14) 0.0617(9) 0.023(2) Uiso 0.093(3) 1 d PD A 2
N4B N 0.092(2) 0.1017(16) 0.0684(10) 0.023(2) Uiso 0.093(3) 1 d PD A 2
H4B H -0.0104 0.0656 0.0918 0.027 Uiso 0.093(3) 1 calc PR A 2
N5B N 0.677(4) 0.209(3) -0.114(2) 0.023(2) Uiso 0.093(3) 1 d PD A 2
H5X H 0.779 0.1953 -0.1658 0.027 Uiso 0.093(3) 1 calc PR A 2
H5Y H 0.6864 0.2449 -0.064 0.027 Uiso 0.093(3) 1 calc PR A 2
C1B C 0.343(2) 0.0579(15) -0.1830(9) 0.0157(19) Uiso 0.093(3) 1 d PD A 2
H1X H 0.3368 0.0212 -0.2394 0.019 Uiso 0.093(3) 1 calc PR A 2
C2B C 0.207(2) 0.1023(18) -0.0236(12) 0.0157(19) Uiso 0.093(3) 1 d PD A 2
C3B C 0.3553(16) 0.1708(12) -0.0271(7) 0.0157(19) Uiso 0.093(3) 1 d PD A 2
C4B C 0.5048(17) 0.1730(13) -0.1130(8) 0.0157(19) Uiso 0.093(3) 1 d PD A 2
C5B C 0.1759(19) 0.1726(13) 0.1162(10) 0.0157(19) Uiso 0.093(3) 1 d PD A 2
H5Z H 0.1254 0.19 0.1828 0.019 Uiso 0.093(3) 1 calc PR A 2
O1 O 0.49125(15) 0.36228(11) 0.14553(7) 0.0348(2) Uani 1 1 d . . .
H1 H 0.4666 0.325 0.1028 0.042 Uiso 1 1 calc R . .
O2 O 0.74443(15) 0.39878(11) 0.02403(7) 0.0333(2) Uani 1 1 d . . .
C6 C 0.7094(2) 0.47533(13) 0.17919(9) 0.0253(3) Uani 1 1 d . . .
C7 C 0.5867(2) 0.49898(14) 0.27201(10) 0.0305(3) Uani 1 1 d . . .
H7 H 0.4623 0.4737 0.291 0.037 Uiso 1 1 calc R . .
C8 C 0.6474(2) 0.55972(15) 0.33658(11) 0.0388(3) Uani 1 1 d . . .
H8 H 0.5638 0.5766 0.3996 0.047 Uiso 1 1 calc R . .
C9 C 0.8291(3) 0.59563(16) 0.30914(12) 0.0427(4) Uani 1 1 d . . .
H9 H 0.8708 0.6361 0.3538 0.051 Uiso 1 1 calc R . .
C10 C 0.9505(2) 0.57308(15) 0.21736(11) 0.0380(3) Uani 1 1 d . . .
H10 H 1.075 0.5983 0.1989 0.046 Uiso 1 1 calc R . .
C11 C 0.8908(2) 0.51366(14) 0.15201(10) 0.0303(3) Uani 1 1 d . . .
H11 H 0.9737 0.4991 0.0886 0.036 Uiso 1 1 calc R . .
C12 C 0.65076(19) 0.40923(13) 0.10822(9) 0.0254(3) Uani 1 1 d . . .
O3 O -0.30044(13) 0.12710(10) 0.63054(6) 0.0282(2) Uani 1 1 d . . .
H3 H -0.3649 0.1113 0.687 0.034 Uiso 1 1 calc R . .
O4 O -0.05518(15) 0.11742(12) 0.71092(7) 0.0395(3) Uani 1 1 d . . .
C13 C 0.00999(19) 0.16268(13) 0.53844(9) 0.0231(3) Uani 1 1 d . . .
C14 C 0.2187(2) 0.14953(15) 0.53057(10) 0.0302(3) Uani 1 1 d . . .
H14 H 0.2814 0.1184 0.5861 0.036 Uiso 1 1 calc R . .
C15 C 0.3355(2) 0.18166(16) 0.44207(11) 0.0368(3) Uani 1 1 d . . .
H15 H 0.4785 0.1719 0.437 0.044 Uiso 1 1 calc R . .
C16 C 0.2456(2) 0.22787(15) 0.36084(10) 0.0357(3) Uani 1 1 d . . .
H16 H 0.326 0.2512 0.3004 0.043 Uiso 1 1 calc R . .
C17 C 0.0385(2) 0.23997(15) 0.36795(10) 0.0344(3) Uani 1 1 d . . .
H17 H -0.0233 0.2707 0.3121 0.041 Uiso 1 1 calc R . .
C18 C -0.0792(2) 0.20741(14) 0.45617(9) 0.0284(3) Uani 1 1 d . . .
H18 H -0.2214 0.2156 0.4607 0.034 Uiso 1 1 calc R . .
C19 C -0.11665(19) 0.13293(13) 0.63489(9) 0.0251(3) Uani 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1A C1A 1.339(2) . ?
N1A C4A 1.362(2) . ?
N2A C1A 1.3268(19) . ?
N2A C2A 1.3560(19) . ?
N3A C5A 1.315(2) . ?
N3A C3A 1.3895(19) . ?
N4A C5A 1.3536(19) . ?
N4A C2A 1.367(2) . ?
N4A H4A 0.88 . ?
N5A C4A 1.332(2) . ?
N5A H5A 0.88 . ?
N5A H5B 0.88 . ?
C1A H1A 0.95 . ?
C2A C3A 1.3828(19) . ?
C3A C4A 1.409(2) . ?
C5A H5C 0.95 . ?
N1B C1B 1.329(14) . ?
N1B C4B 1.370(14) . ?
N2B C2B 1.353(14) . ?
N2B C1B 1.364(15) . ?
N3B C5B 1.317(14) . ?
N3B C3B 1.352(13) . ?
N4B C2B 1.361(14) . ?
N4B C5B 1.393(14) . ?
N4B H4B 0.88 . ?
N5B C4B 1.354(16) . ?
N5B H5X 0.88 . ?
N5B H5Y 0.88 . ?
C1B H1X 0.95 . ?
C2B C3B 1.410(14) . ?
C3B C4B 1.404(12) . ?
C5B H5Z 0.95 . ?
O1 C12 1.3163(15) . ?
O1 H1 0.84 . ?
O2 C12 1.2195(15) . ?
C6 C11 1.3924(18) . ?
C6 C7 1.3960(18) . ?
C6 C12 1.4900(18) . ?
C7 C8 1.389(2) . ?
C7 H7 0.95 . ?
C8 C9 1.382(2) . ?
C8 H8 0.95 . ?
C9 C10 1.379(2) . ?
C9 H9 0.95 . ?
C10 C11 1.386(2) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
O3 C19 1.3131(15) . ?
O3 H3 0.84 . ?
O4 C19 1.2207(15) . ?
C13 C14 1.3887(17) . ?
C13 C18 1.3923(17) . ?
C13 C19 1.4892(17) . ?
C14 C15 1.382(2) . ?
C14 H14 0.95 . ?
C15 C16 1.383(2) . ?
C15 H15 0.95 . ?
C16 C17 1.382(2) . ?
C16 H16 0.95 . ?
C17 C18 1.3828(18) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?

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
C1A N1A C4A 119.79(12) . . ?
C1A N2A C2A 110.71(14) . . ?
C5A N3A C3A 103.93(12) . . ?
C5A N4A C2A 106.30(12) . . ?
C5A N4A H4A 126.9 . . ?
C2A N4A H4A 126.9 . . ?
C4A N5A H5A 120 . . ?
C4A N5A H5B 120 . . ?
H5A N5A H5B 120 . . ?
N2A C1A N1A 128.75(14) . . ?
N2A C1A H1A 115.6 . . ?
N1A C1A H1A 115.6 . . ?
N2A C2A N4A 127.10(13) . . ?
N2A C2A C3A 126.77(15) . . ?
N4A C2A C3A 106.12(14) . . ?
C2A C3A N3A 109.90(13) . . ?
C2A C3A C4A 117.50(13) . . ?
N3A C3A C4A 132.59(13) . . ?
N5A C4A N1A 118.94(15) . . ?
N5A C4A C3A 124.65(16) . . ?
N1A C4A C3A 116.41(12) . . ?
N3A C5A N4A 113.75(14) . . ?
N3A C5A H5C 123.1 . . ?
N4A C5A H5C 123.1 . . ?
C1B N1B C4B 118.6(11) . . ?
C2B N2B C1B 114.6(13) . . ?
C5B N3B C3B 105.1(12) . . ?
C2B N4B C5B 102.7(11) . . ?
C2B N4B H4B 128.7 . . ?
C5B N4B H4B 128.7 . . ?
C4B N5B H5X 120 . . ?
C4B N5B H5Y 120 . . ?
H5X N5B H5Y 120 . . ?
N1B C1B N2B 127.2(13) . . ?
N1B C1B H1X 116.4 . . ?
N2B C1B H1X 116.4 . . ?
N2B C2B N4B 129.0(13) . . ?
N2B C2B C3B 122.4(13) . . ?
N4B C2B C3B 108.6(11) . . ?
N3B C3B C4B 132.1(11) . . ?
N3B C3B C2B 108.9(11) . . ?
C4B C3B C2B 118.7(10) . . ?
N5B C4B N1B 119.4(15) . . ?
N5B C4B C3B 121.3(16) . . ?
N1B C4B C3B 118.4(10) . . ?
N3B C5B N4B 114.7(12) . . ?
N3B C5B H5Z 122.6 . . ?
N4B C5B H5Z 122.6 . . ?
C12 O1 H1 109.5 . . ?
C11 C6 C7 119.64(12) . . ?
C11 C6 C12 119.03(12) . . ?
C7 C6 C12 121.33(11) . . ?
C8 C7 C6 119.73(13) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 120.06(14) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C10 C9 C8 120.45(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.04(14) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C10 C11 C6 120.07(13) . . ?
C10 C11 H11 120 . . ?
C6 C11 H11 120 . . ?
O2 C12 O1 123.77(12) . . ?
O2 C12 C6 122.62(11) . . ?
O1 C12 C6 113.60(11) . . ?
C19 O3 H3 109.5 . . ?
C14 C13 C18 119.26(12) . . ?
C14 C13 C19 119.73(11) . . ?
C18 C13 C19 120.98(11) . . ?
C15 C14 C13 120.13(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.42(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.76(13) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.15(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.28(12) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O4 C19 O3 123.41(12) . . ?
O4 C19 C13 122.67(11) . . ?
O3 C19 C13 113.91(10) . . ?

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
C2A N2A C1A N1A 1.6(2) . . . . ?
C4A N1A C1A N2A 0.3(2) . . . . ?
C1A N2A C2A N4A 179.55(15) . . . . ?
C1A N2A C2A C3A -1.3(2) . . . . ?
C5A N4A C2A N2A 179.80(15) . . . . ?
C5A N4A C2A C3A 0.47(17) . . . . ?
N2A C2A C3A N3A -179.58(14) . . . . ?
N4A C2A C3A N3A -0.26(16) . . . . ?
N2A C2A C3A C4A -0.8(2) . . . . ?
N4A C2A C3A C4A 178.56(13) . . . . ?
C5A N3A C3A C2A -0.07(16) . . . . ?
C5A N3A C3A C4A -178.64(15) . . . . ?
C1A N1A C4A N5A 177.5(2) . . . . ?
C1A N1A C4A C3A -2.48(19) . . . . ?
C2A C3A C4A N5A -177.3(2) . . . . ?
N3A C3A C4A N5A 1.2(3) . . . . ?
C2A C3A C4A N1A 2.63(19) . . . . ?
N3A C3A C4A N1A -178.88(14) . . . . ?
C3A N3A C5A N4A 0.39(17) . . . . ?
C2A N4A C5A N3A -0.56(19) . . . . ?
C4B N1B C1B N2B -1(2) . . . . ?
C2B N2B C1B N1B 2(3) . . . . ?
C1B N2B C2B N4B -176.9(18) . . . . ?
C1B N2B C2B C3B 0(3) . . . . ?
C5B N4B C2B N2B 178.3(19) . . . . ?
C5B N4B C2B C3B 0.7(19) . . . . ?
C5B N3B C3B C4B -173.9(14) . . . . ?
C5B N3B C3B C2B 0.1(16) . . . . ?
N2B C2B C3B N3B -178.3(17) . . . . ?
N4B C2B C3B N3B -0.5(19) . . . . ?
N2B C2B C3B C4B -3(2) . . . . ?
N4B C2B C3B C4B 174.3(13) . . . . ?
C1B N1B C4B N5B 167(2) . . . . ?
C1B N1B C4B C3B -2.2(19) . . . . ?
N3B C3B C4B N5B 8(3) . . . . ?
C2B C3B C4B N5B -165(2) . . . . ?
N3B C3B C4B N1B 177.7(14) . . . . ?
C2B C3B C4B N1B 4.3(19) . . . . ?
C3B N3B C5B N4B 0.4(17) . . . . ?
C2B N4B C5B N3B -0.7(19) . . . . ?
C11 C6 C7 C8 -0.4(2) . . . . ?
C12 C6 C7 C8 179.42(12) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C6 -0.6(2) . . . . ?
C7 C6 C11 C10 0.94(19) . . . . ?
C12 C6 C11 C10 -178.88(12) . . . . ?
C11 C6 C12 O2 -6.91(19) . . . . ?
C7 C6 C12 O2 173.28(12) . . . . ?
C11 C6 C12 O1 172.29(11) . . . . ?
C7 C6 C12 O1 -7.53(17) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C19 C13 C14 C15 -177.73(12) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C19 C13 C18 C17 177.42(12) . . . . ?
C14 C13 C19 O4 11.2(2) . . . . ?
C18 C13 C19 O4 -166.95(13) . . . . ?
C14 C13 C19 O3 -169.72(11) . . . . ?
C18 C13 C19 O3 12.09(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1A 0.84 1.8 2.6357(15) 170.2 2_665
O1 H1 N3B 0.84 1.92 2.694(14) 152.3 .
O3 H3 N3A 0.84 1.84 2.6721(15) 170.2 2_566
O3 H3 N1B 0.84 1.77 2.596(12) 167.7 1_456
N5A H5B O4 0.88 2.15 3.017(2) 166.3 2_566
N5A H5A O2 0.88 2.06 2.927(2) 167.1 2_665
N4A H4A N2A 0.88 1.98 2.8506(17) 167.6 2_775
N5B H5X O4 0.88 1.97 2.80(3) 156.7 1_654
N5B H5Y O2 0.88 2.33 3.17(2) 159.2 .
N4B H4B N2B 0.88 1.95 2.796(19) 160.1 2

#-----------------------END OF CIF 1 OF 6---------------------------------

data_addip
_database_code_depnum_ccdc_archive 'CCDC 686684'

_audit_creation_date             2008-02-12T13:03:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Adenine - adipic acid (2:1) dimethanolate
;
_chemical_formula_moiety         
;
2(C5 H5 N5), C6 H10 O4, 2(C1 H4 O1)
;
_chemical_formula_sum            'C18 H28 N10 O6'
_chemical_formula_weight         480.5
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9781(5)
_cell_length_b                   9.9334(5)
_cell_length_c                   14.2815(7)
_cell_angle_alpha                74.908(3)
_cell_angle_beta                 85.357(3)
_cell_angle_gamma                66.786(3)
_cell_volume                     1129.84(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.6436
_exptl_absorpt_correction_T_max  0.9935

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_number            22714
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_reflns_number_total             5137
_reflns_number_gt                3644
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0539P)²+0.2864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5137
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.81696(16) -0.10103(15) 0.02250(8) 0.0287(3) Uani 1 1 d . . .
H1 H 0.7421 -0.1263 0.0121 0.034 Uiso 1 1 calc R . .
O2 O 0.72167(16) -0.13095(14) 0.17253(9) 0.0296(3) Uani 1 1 d . . .
O3 O 1.07342(16) 0.20006(14) 0.46546(8) 0.0273(3) Uani 1 1 d . . .
H3 H 1.1147 0.2597 0.4721 0.033 Uiso 1 1 calc R . .
O4 O 1.17570(16) 0.23689(14) 0.31762(9) 0.0292(3) Uani 1 1 d . . .
C1 C 0.8157(2) -0.09603(18) 0.11400(12) 0.0215(4) Uani 1 1 d . . .
C2 C 0.9392(2) -0.04260(19) 0.13745(12) 0.0230(4) Uani 1 1 d . . .
H2A H 0.9259 0.0543 0.0902 0.028 Uiso 1 1 calc R . .
H2B H 1.0487 -0.1172 0.1294 0.028 Uiso 1 1 calc R . .
C3 C 0.9290(2) -0.0200(2) 0.23913(12) 0.0248(4) Uani 1 1 d . . .
H3A H 0.9605 -0.1197 0.2865 0.03 Uiso 1 1 calc R . .
H3B H 0.8152 0.0415 0.2512 0.03 Uiso 1 1 calc R . .
C4 C 1.0371(2) 0.05795(19) 0.25571(12) 0.0226(4) Uani 1 1 d . . .
H4X H 1.1521 -0.007 0.2493 0.027 Uiso 1 1 calc R . .
H4Y H 1.0114 0.1547 0.2058 0.027 Uiso 1 1 calc R . .
C5 C 1.0121(2) 0.0883(2) 0.35602(12) 0.0240(4) Uani 1 1 d . . .
H5C H 0.8944 0.1402 0.3646 0.029 Uiso 1 1 calc R . .
H5D H 1.0499 -0.0101 0.405 0.029 Uiso 1 1 calc R . .
C6 C 1.0965(2) 0.18148(18) 0.37634(12) 0.0209(4) Uani 1 1 d . . .
N1A N 0.69115(18) 0.33731(16) -0.10302(10) 0.0242(3) Uani 1 1 d . . .
N2A N 0.67769(18) 0.35362(16) 0.06348(10) 0.0238(3) Uani 1 1 d . . .
N3A N 0.39550(18) 0.19121(16) 0.03706(10) 0.0246(3) Uani 1 1 d . . .
N4A N 0.48258(18) 0.25774(16) 0.15344(10) 0.0236(3) Uani 1 1 d . . .
H4A H 0.4913 0.2719 0.2107 0.028 Uiso 1 1 calc R . .
N5A N 0.54444(18) 0.23177(16) -0.16597(10) 0.0252(3) Uani 1 1 d . . .
H5A H 0.5914 0.248 -0.222 0.03 Uiso 1 1 calc R . .
H5B H 0.4735 0.1893 -0.1593 0.03 Uiso 1 1 calc R . .
C1A C 0.7315(2) 0.37229(19) -0.02717(12) 0.0254(4) Uani 1 1 d . . .
H1A H 0.8096 0.4168 -0.0394 0.031 Uiso 1 1 calc R . .
C2A C 0.5662(2) 0.29108(18) 0.07267(12) 0.0209(4) Uani 1 1 d . . .
C3A C 0.5112(2) 0.24995(18) 0.00074(12) 0.0219(4) Uani 1 1 d . . .
C4A C 0.5809(2) 0.27163(18) -0.09122(12) 0.0223(4) Uani 1 1 d . . .
C5A C 0.3831(2) 0.1984(2) 0.12828(12) 0.0254(4) Uani 1 1 d . . .
H5Z H 0.3119 0.1654 0.1722 0.03 Uiso 1 1 calc R . .
N1B N 0.31230(18) 0.67665(16) 0.35973(10) 0.0247(3) Uani 1 1 d . . .
N2B N 0.33385(18) 0.66227(16) 0.52952(10) 0.0250(3) Uani 1 1 d . . .
N3B N 0.20036(19) 0.37091(16) 0.51917(10) 0.0256(3) Uani 1 1 d . . .
N4B N 0.25561(18) 0.46426(16) 0.63270(10) 0.0252(3) Uani 1 1 d . . .
H4B H 0.2677 0.4749 0.6905 0.03 Uiso 1 1 calc R . .
N5B N 0.22308(18) 0.52150(16) 0.30273(10) 0.0255(3) Uani 1 1 d . . .
H5X H 0.2325 0.5703 0.243 0.031 Uiso 1 1 calc R . .
H5Y H 0.1893 0.447 0.313 0.031 Uiso 1 1 calc R . .
C1B C 0.3450(2) 0.7177(2) 0.43474(13) 0.0262(4) Uani 1 1 d . . .
H1B H 0.3816 0.7983 0.4183 0.031 Uiso 1 1 calc R . .
C2B C 0.2817(2) 0.54815(19) 0.54559(12) 0.0225(4) Uani 1 1 d . . .
C3B C 0.2463(2) 0.49071(19) 0.47539(12) 0.0223(4) Uani 1 1 d . . .
C4B C 0.2601(2) 0.56042(19) 0.37771(12) 0.0228(4) Uani 1 1 d . . .
C5B C 0.2074(2) 0.3610(2) 0.61245(13) 0.0278(4) Uani 1 1 d . . .
H5E H 0.1812 0.2886 0.6611 0.033 Uiso 1 1 calc R . .
O5 O 0.79813(16) 0.45337(15) 0.19517(9) 0.0319(3) Uani 1 1 d . . .
H5 H 0.7491 0.4257 0.1611 0.038 Uiso 1 1 calc R . .
C7 C 0.9176(2) 0.4960(2) 0.13904(13) 0.0311(4) Uani 1 1 d . . .
H7A H 0.8665 0.574 0.0802 0.037 Uiso 1 1 calc R . .
H7B H 1.0001 0.4075 0.1211 0.037 Uiso 1 1 calc R . .
H7C H 0.9687 0.5361 0.1771 0.037 Uiso 1 1 calc R . .
O6 O 0.56911(17) 0.22931(14) 0.33651(8) 0.0304(3) Uani 1 1 d . . .
H6 H 0.5923 0.2769 0.3699 0.037 Uiso 1 1 calc R . .
C8 C 0.5606(3) 0.0955(2) 0.39778(14) 0.0356(5) Uani 1 1 d . . .
H8A H 0.6622 0.0365 0.4356 0.043 Uiso 1 1 calc R . .
H8B H 0.5436 0.0353 0.3583 0.043 Uiso 1 1 calc R . .
H8C H 0.4703 0.1219 0.4419 0.043 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.320(2) . ?
O1 H1 0.84 . ?
O2 C1 1.223(2) . ?
O3 C6 1.322(2) . ?
O3 H3 0.84 . ?
O4 C6 1.218(2) . ?
C1 C2 1.497(2) . ?
C2 C3 1.517(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.524(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.521(2) . ?
C4 H4X 0.99 . ?
C4 H4Y 0.99 . ?
C5 C6 1.498(2) . ?
C5 H5C 0.99 . ?
C5 H5D 0.99 . ?
N1A C1A 1.336(2) . ?
N1A C4A 1.363(2) . ?
N2A C1A 1.337(2) . ?
N2A C2A 1.354(2) . ?
N3A C5A 1.316(2) . ?
N3A C3A 1.386(2) . ?
N4A C5A 1.361(2) . ?
N4A C2A 1.364(2) . ?
N4A H4A 0.88 . ?
N5A C4A 1.335(2) . ?
N5A H5A 0.88 . ?
N5A H5B 0.88 . ?
C1A H1A 0.95 . ?
C2A C3A 1.388(2) . ?
C3A C4A 1.410(2) . ?
C5A H5Z 0.95 . ?
N1B C1B 1.331(2) . ?
N1B C4B 1.368(2) . ?
N2B C1B 1.334(2) . ?
N2B C2B 1.350(2) . ?
N3B C5B 1.315(2) . ?
N3B C3B 1.391(2) . ?
N4B C5B 1.359(2) . ?
N4B C2B 1.365(2) . ?
N4B H4B 0.88 . ?
N5B C4B 1.334(2) . ?
N5B H5X 0.88 . ?
N5B H5Y 0.88 . ?
C1B H1B 0.95 . ?
C2B C3B 1.387(2) . ?
C3B C4B 1.406(2) . ?
C5B H5E 0.95 . ?
O5 C7 1.420(2) . ?
O5 H5 0.84 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
O6 C8 1.415(2) . ?
O6 H6 0.84 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?

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
C1 O1 H1 109.5 . . ?
C6 O3 H3 109.5 . . ?
O2 C1 O1 122.72(16) . . ?
O2 C1 C2 124.26(15) . . ?
O1 C1 C2 113.02(14) . . ?
C1 C2 C3 114.22(14) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 113.07(14) . . ?
C2 C3 H3A 109 . . ?
C4 C3 H3A 109 . . ?
C2 C3 H3B 109 . . ?
C4 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 110.65(14) . . ?
C5 C4 H4X 109.5 . . ?
C3 C4 H4X 109.5 . . ?
C5 C4 H4Y 109.5 . . ?
C3 C4 H4Y 109.5 . . ?
H4X C4 H4Y 108.1 . . ?
C6 C5 C4 115.58(14) . . ?
C6 C5 H5C 108.4 . . ?
C4 C5 H5C 108.4 . . ?
C6 C5 H5D 108.4 . . ?
C4 C5 H5D 108.4 . . ?
H5C C5 H5D 107.4 . . ?
O4 C6 O3 123.01(15) . . ?
O4 C6 C5 124.51(15) . . ?
O3 C6 C5 112.47(14) . . ?
C1A N1A C4A 118.97(14) . . ?
C1A N2A C2A 110.51(14) . . ?
C5A N3A C3A 104.06(14) . . ?
C5A N4A C2A 106.72(14) . . ?
C5A N4A H4A 126.6 . . ?
C2A N4A H4A 126.6 . . ?
C4A N5A H5A 120 . . ?
C4A N5A H5B 120 . . ?
H5A N5A H5B 120 . . ?
N1A C1A N2A 129.29(16) . . ?
N1A C1A H1A 115.4 . . ?
N2A C1A H1A 115.4 . . ?
N2A C2A N4A 127.49(15) . . ?
N2A C2A C3A 126.82(15) . . ?
N4A C2A C3A 105.68(14) . . ?
N3A C3A C2A 110.25(14) . . ?
N3A C3A C4A 132.64(15) . . ?
C2A C3A C4A 117.10(15) . . ?
N5A C4A N1A 119.15(15) . . ?
N5A C4A C3A 123.60(15) . . ?
N1A C4A C3A 117.25(15) . . ?
N3A C5A N4A 113.28(15) . . ?
N3A C5A H5Z 123.4 . . ?
N4A C5A H5Z 123.4 . . ?
C1B N1B C4B 118.57(14) . . ?
C1B N2B C2B 110.88(15) . . ?
C5B N3B C3B 103.94(14) . . ?
C5B N4B C2B 106.45(14) . . ?
C5B N4B H4B 126.8 . . ?
C2B N4B H4B 126.8 . . ?
C4B N5B H5X 120 . . ?
C4B N5B H5Y 120 . . ?
H5X N5B H5Y 120 . . ?
N1B C1B N2B 129.55(16) . . ?
N1B C1B H1B 115.2 . . ?
N2B C1B H1B 115.2 . . ?
N2B C2B N4B 127.80(15) . . ?
N2B C2B C3B 126.23(15) . . ?
N4B C2B C3B 105.97(14) . . ?
C2B C3B N3B 110.00(15) . . ?
C2B C3B C4B 117.55(15) . . ?
N3B C3B C4B 132.45(16) . . ?
N5B C4B N1B 118.80(15) . . ?
N5B C4B C3B 124.01(15) . . ?
N1B C4B C3B 117.18(15) . . ?
N3B C5B N4B 113.64(16) . . ?
N3B C5B H5E 123.2 . . ?
N4B C5B H5E 123.2 . . ?
C7 O5 H5 109.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 O6 H6 109.5 . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O2 C1 C2 C3 -5.6(2) . . . . ?
O1 C1 C2 C3 173.92(14) . . . . ?
C1 C2 C3 C4 -170.77(14) . . . . ?
C2 C3 C4 C5 175.69(15) . . . . ?
C3 C4 C5 C6 -172.78(15) . . . . ?
C4 C5 C6 O4 2.9(3) . . . . ?
C4 C5 C6 O3 -178.27(15) . . . . ?
C4A N1A C1A N2A -0.6(3) . . . . ?
C2A N2A C1A N1A -0.6(3) . . . . ?
C1A N2A C2A N4A -178.74(16) . . . . ?
C1A N2A C2A C3A 0.0(2) . . . . ?
C5A N4A C2A N2A 179.30(16) . . . . ?
C5A N4A C2A C3A 0.31(18) . . . . ?
C5A N3A C3A C2A 0.15(19) . . . . ?
C5A N3A C3A C4A 178.94(18) . . . . ?
N2A C2A C3A N3A -179.28(16) . . . . ?
N4A C2A C3A N3A -0.29(18) . . . . ?
N2A C2A C3A C4A 1.7(3) . . . . ?
N4A C2A C3A C4A -179.30(15) . . . . ?
C1A N1A C4A N5A -177.73(15) . . . . ?
C1A N1A C4A C3A 2.4(2) . . . . ?
N3A C3A C4A N5A -1.5(3) . . . . ?
C2A C3A C4A N5A 177.28(16) . . . . ?
N3A C3A C4A N1A 178.42(17) . . . . ?
C2A C3A C4A N1A -2.8(2) . . . . ?
C3A N3A C5A N4A 0.1(2) . . . . ?
C2A N4A C5A N3A -0.2(2) . . . . ?
C4B N1B C1B N2B -0.5(3) . . . . ?
C2B N2B C1B N1B 0.3(3) . . . . ?
C1B N2B C2B N4B 180.00(17) . . . . ?
C1B N2B C2B C3B 1.2(2) . . . . ?
C5B N4B C2B N2B -178.64(17) . . . . ?
C5B N4B C2B C3B 0.31(19) . . . . ?
N2B C2B C3B N3B 178.33(16) . . . . ?
N4B C2B C3B N3B -0.65(19) . . . . ?
N2B C2B C3B C4B -2.4(3) . . . . ?
N4B C2B C3B C4B 178.61(15) . . . . ?
C5B N3B C3B C2B 0.7(2) . . . . ?
C5B N3B C3B C4B -178.39(19) . . . . ?
C1B N1B C4B N5B 178.26(16) . . . . ?
C1B N1B C4B C3B -0.7(2) . . . . ?
C2B C3B C4B N5B -176.93(16) . . . . ?
N3B C3B C4B N5B 2.1(3) . . . . ?
C2B C3B C4B N1B 2.0(2) . . . . ?
N3B C3B C4B N1B -178.95(17) . . . . ?
C3B N3B C5B N4B -0.5(2) . . . . ?
C2B N4B C5B N3B 0.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3A 0.84 1.85 2.6779(18) 166.4 2_655
O3 H3 N3B 0.84 1.84 2.6668(18) 165.7 1_655
N4A H4A O6 0.88 1.86 2.7001(18) 158.4 .
N5A H5A N1B 0.88 2.16 3.029(2) 171.4 2_665
N5A H5B O2 0.88 2.09 2.9481(19) 166.1 2_655
N4B H4B O5 0.88 1.91 2.7366(18) 156.4 2_666
N5B H5X N1A 0.88 2.15 3.018(2) 168 2_665
N5B H5Y O4 0.88 2.12 2.9731(18) 162.5 1_455
O5 H5 N2A 0.84 1.97 2.7988(18) 167.2 .
O6 H6 N2B 0.84 1.95 2.7680(19) 165.6 2_666

#---------------------------END OF CIF 2 OF 6-----------------------------------

data_ad26
_database_code_depnum_ccdc_archive 'CCDC 686685'

_audit_creation_date             2008-02-12T13:46:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Adenine 2,6-dihydroxybenzoate
;
_chemical_formula_moiety         
;
C5 H6 N5 1+, C7 H5 O4 1-
;
_chemical_formula_sum            'C12 H11 N5 O4'
_chemical_formula_weight         289.26
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0966(3)
_cell_length_b                   7.2069(3)
_cell_length_c                   23.5630(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.978(3)
_cell_angle_gamma                90
_cell_volume                     1202.21(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6301
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.7409
_exptl_absorpt_correction_T_max  0.9975

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_number            13251
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2738
_reflns_number_gt                1862
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0488P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2738
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.8109(2) 0.3844(2) 0.06569(6) 0.0229(4) Uani 1 1 d . . .
O2 O 1.0539(2) 0.3518(2) 0.13030(6) 0.0213(4) Uani 1 1 d . . .
O3 O 0.4944(2) 0.5017(2) 0.09277(6) 0.0234(4) Uani 1 1 d . . .
H3 H 0.5749 0.4595 0.0717 0.028 Uiso 1 1 calc R . .
O4 O 1.02687(19) 0.4790(2) 0.23116(6) 0.0228(4) Uani 1 1 d . . .
H4 H 1.0774 0.4305 0.2036 0.027 Uiso 1 1 calc R . .
C6 C 0.8863(3) 0.4012(3) 0.11654(9) 0.0167(5) Uani 1 1 d . . .
C7 C 0.7678(3) 0.4827(3) 0.15962(8) 0.0156(4) Uani 1 1 d . . .
C8 C 0.5770(3) 0.5328(3) 0.14554(9) 0.0166(4) Uani 1 1 d . . .
C9 C 0.4691(3) 0.6179(3) 0.18525(9) 0.0189(5) Uani 1 1 d . . .
H9 H 0.3416 0.6516 0.1754 0.023 Uiso 1 1 calc R . .
C10 C 0.5502(3) 0.6528(3) 0.23932(9) 0.0188(5) Uani 1 1 d . . .
H10 H 0.4773 0.7128 0.2662 0.023 Uiso 1 1 calc R . .
C11 C 0.7348(3) 0.6028(3) 0.25534(9) 0.0185(5) Uani 1 1 d . . .
H11 H 0.7864 0.6251 0.293 0.022 Uiso 1 1 calc R . .
C12 C 0.8435(3) 0.5195(3) 0.21564(9) 0.0165(5) Uani 1 1 d . . .
N1 N 1.0206(2) 0.7587(2) 0.02036(7) 0.0174(4) Uani 1 1 d . . .
H1A H 1.0702 0.7103 -0.0095 0.021 Uiso 1 1 calc R . .
N2 N 1.0735(2) 0.8292(2) 0.11871(7) 0.0193(4) Uani 1 1 d . . .
N3 N 0.6004(2) 0.9739(2) 0.07495(8) 0.0198(4) Uani 1 1 d . . .
N4 N 0.7928(2) 0.9668(2) 0.15459(7) 0.0180(4) Uani 1 1 d . . .
H4A H 0.8314 0.9821 0.1906 0.022 Uiso 1 1 calc R . .
N5 N 0.7460(2) 0.8166(3) -0.03635(7) 0.0208(4) Uani 1 1 d . . .
H5A H 0.7991 0.7671 -0.0654 0.025 Uiso 1 1 calc R . .
H5B H 0.6299 0.8598 -0.0407 0.025 Uiso 1 1 calc R . .
C1 C 1.1272(3) 0.7626(3) 0.07062(9) 0.0195(5) Uani 1 1 d . . .
H1 H 1.2512 0.7128 0.0709 0.023 Uiso 1 1 calc R . .
C2 C 0.8945(3) 0.8956(3) 0.11291(9) 0.0158(4) Uani 1 1 d . . .
C3 C 0.7745(3) 0.9004(3) 0.06365(9) 0.0155(4) Uani 1 1 d . . .
C4 C 0.8405(3) 0.8260(3) 0.01385(9) 0.0167(5) Uani 1 1 d . . .
C5 C 0.6196(3) 1.0096(3) 0.12965(9) 0.0208(5) Uani 1 1 d . . .
H5 H 0.5212 1.0608 0.1501 0.025 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.283(2) . ?
O2 C6 1.262(2) . ?
O3 C8 1.356(2) . ?
O3 H3 0.84 . ?
O4 C12 1.359(2) . ?
O4 H4 0.84 . ?
C6 C7 1.484(3) . ?
C7 C12 1.415(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.95 . ?
C10 C11 1.385(3) . ?
C10 H10 0.95 . ?
C11 C12 1.389(3) . ?
C11 H11 0.95 . ?
N1 C1 1.361(3) . ?
N1 C4 1.366(3) . ?
N1 H1A 0.88 . ?
N2 C1 1.311(3) . ?
N2 C2 1.355(3) . ?
N3 C5 1.312(3) . ?
N3 C3 1.387(3) . ?
N4 C2 1.359(3) . ?
N4 C5 1.360(3) . ?
N4 H4A 0.88 . ?
N5 C4 1.320(3) . ?
N5 H5A 0.88 . ?
N5 H5B 0.88 . ?
C1 H1 0.95 . ?
C2 C3 1.392(3) . ?
C3 C4 1.400(3) . ?
C5 H5 0.95 . ?

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 O3 H3 109.5 . . ?
C12 O4 H4 109.5 . . ?
O2 C6 O1 122.52(19) . . ?
O2 C6 C7 120.30(18) . . ?
O1 C6 C7 117.18(18) . . ?
C12 C7 C8 117.70(19) . . ?
C12 C7 C6 121.07(18) . . ?
C8 C7 C6 121.19(18) . . ?
O3 C8 C9 117.77(18) . . ?
O3 C8 C7 121.18(18) . . ?
C9 C8 C7 121.05(18) . . ?
C10 C9 C8 119.05(19) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.91(19) . . ?
C9 C10 H10 119 . . ?
C11 C10 H10 119 . . ?
C10 C11 C12 119.16(19) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
O4 C12 C11 118.52(18) . . ?
O4 C12 C7 120.34(18) . . ?
C11 C12 C7 121.11(19) . . ?
C1 N1 C4 123.37(18) . . ?
C1 N1 H1A 118.3 . . ?
C4 N1 H1A 118.3 . . ?
C1 N2 C2 111.64(18) . . ?
C5 N3 C3 103.32(17) . . ?
C2 N4 C5 106.40(17) . . ?
C2 N4 H4A 126.8 . . ?
C5 N4 H4A 126.8 . . ?
C4 N5 H5A 120 . . ?
C4 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
N2 C1 N1 125.6(2) . . ?
N2 C1 H1 117.2 . . ?
N1 C1 H1 117.2 . . ?
N2 C2 N4 126.96(18) . . ?
N2 C2 C3 127.44(19) . . ?
N4 C2 C3 105.58(18) . . ?
N3 C3 C2 110.55(18) . . ?
N3 C3 C4 131.42(19) . . ?
C2 C3 C4 117.94(19) . . ?
N5 C4 N1 119.70(19) . . ?
N5 C4 C3 126.30(19) . . ?
N1 C4 C3 114.00(18) . . ?
N3 C5 N4 114.14(19) . . ?
N3 C5 H5 122.9 . . ?
N4 C5 H5 122.9 . . ?

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
O2 C6 C7 C12 4.7(3) . . . . ?
O1 C6 C7 C12 -175.13(18) . . . . ?
O2 C6 C7 C8 -177.67(19) . . . . ?
O1 C6 C7 C8 2.5(3) . . . . ?
C12 C7 C8 O3 -179.90(18) . . . . ?
C6 C7 C8 O3 2.4(3) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -176.72(19) . . . . ?
O3 C8 C9 C10 -179.46(19) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C10 C11 C12 O4 177.00(18) . . . . ?
C10 C11 C12 C7 -1.0(3) . . . . ?
C8 C7 C12 O4 -178.28(18) . . . . ?
C6 C7 C12 O4 -0.6(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C6 C7 C12 C11 177.39(19) . . . . ?
C2 N2 C1 N1 0.1(3) . . . . ?
C4 N1 C1 N2 0.2(3) . . . . ?
C1 N2 C2 N4 177.0(2) . . . . ?
C1 N2 C2 C3 -0.9(3) . . . . ?
C5 N4 C2 N2 -177.9(2) . . . . ?
C5 N4 C2 C3 0.3(2) . . . . ?
C5 N3 C3 C2 -0.4(2) . . . . ?
C5 N3 C3 C4 176.1(2) . . . . ?
N2 C2 C3 N3 178.27(19) . . . . ?
N4 C2 C3 N3 0.0(2) . . . . ?
N2 C2 C3 C4 1.3(3) . . . . ?
N4 C2 C3 C4 -176.95(18) . . . . ?
C1 N1 C4 N5 -179.78(19) . . . . ?
C1 N1 C4 C3 0.2(3) . . . . ?
N3 C3 C4 N5 2.9(4) . . . . ?
C2 C3 C4 N5 179.1(2) . . . . ?
N3 C3 C4 N1 -177.0(2) . . . . ?
C2 C3 C4 N1 -0.8(3) . . . . ?
C3 N3 C5 N4 0.6(2) . . . . ?
C2 N4 C5 N3 -0.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O4 0.88 2.04 2.901(2) 166.3 2_755
N5 H5A O2 0.88 2.09 2.971(2) 175.3 3_765
N5 H5B N3 0.88 2.14 2.974(2) 158 3_675
N1 H1A O1 0.88 1.76 2.635(2) 174.9 3_765
O3 H3 O1 0.84 1.77 2.523(2) 147.4 .
O4 H4 O2 0.84 1.81 2.567(2) 148.3 .

#--------------------END OF CIF 3 OF 6---------------------------------------

data_ad26h
_database_code_depnum_ccdc_archive 'CCDC 686686'

_audit_creation_date             2008-02-12T14:29:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Adenine 2,6-dihydroxybenzoate hydrate
;
_chemical_formula_moiety         
;
C7 H5 O4 1-, C5 H6 N5 1+, H2 O1
;
_chemical_formula_sum            'C12 H13 N5 O5'
_chemical_formula_weight         307.27
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9541(2)
_cell_length_b                   15.2160(6)
_cell_length_c                   7.0195(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.59
_cell_angle_gamma                90
_cell_volume                     652.20(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8129
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.7715
_exptl_absorpt_correction_T_max  0.9755

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_number            8951
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             1538
_reflns_number_gt                1468
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0434P)²+2.1292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1538
_refine_ls_number_parameters     205
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.087

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.3392(6) 0.7250(3) 0.7152(6) 0.0198(8) Uani 1 1 d . . .
O2 O -0.0982(6) 0.7229(3) 1.0698(6) 0.0219(9) Uani 1 1 d . . .
O3 O -0.2536(6) 0.8061(3) 0.4474(6) 0.0201(8) Uani 1 1 d . . .
H3 H -0.3396 0.7924 0.4952 0.024 Uiso 1 1 d R . .
O4 O 0.2829(7) 0.7849(3) 1.2033(6) 0.0224(9) Uani 1 1 d . . .
H4 H 0.175 0.7636 1.2102 0.027 Uiso 1 1 d R . .
O5 O 0.5296(6) 0.9769(3) 0.3995(6) 0.0208(8) Uani 1 1 d D . .
H5X H 0.626(8) 0.993(3) 0.525(6) 0.02 Uiso 1 1 d D . .
H5Y H 0.557(10) 0.9225(17) 0.392(9) 0.02 Uiso 1 1 d D . .
N1 N 0.3496(7) 0.6411(3) 0.7753(7) 0.0169(9) Uani 1 1 d . . .
H1A H 0.449 0.6698 0.7563 0.02 Uiso 1 1 calc R . .
N2 N -0.0157(8) 0.5892(3) 0.5999(7) 0.0173(9) Uani 1 1 d . . .
N3 N 0.2192(8) 0.5356(3) 1.1679(7) 0.0180(9) Uani 1 1 d . . .
N4 N -0.1054(8) 0.5203(3) 0.8634(7) 0.0171(9) Uani 1 1 d . . .
H4A H -0.2424 0.5049 0.7785 0.02 Uiso 1 1 d R . .
N5 N 0.6039(7) 0.6262(3) 1.1414(7) 0.0201(10) Uani 1 1 d . . .
H5A H 0.7014 0.6545 1.1186 0.024 Uiso 1 1 calc R . .
H5B H 0.6386 0.6073 1.2724 0.024 Uiso 1 1 calc R . .
C1 C 0.1529(9) 0.6285(4) 0.6019(9) 0.0177(10) Uani 1 1 d . . .
H1 H 0.1338 0.6503 0.4671 0.021 Uiso 1 1 calc R . .
C2 C 0.0333(8) 0.5609(3) 0.8019(8) 0.0154(10) Uani 1 1 d . . .
C3 C 0.2321(9) 0.5699(4) 0.9918(8) 0.0163(10) Uani 1 1 d . . .
C4 C 0.4058(9) 0.6122(3) 0.9792(9) 0.0171(10) Uani 1 1 d . . .
C5 C 0.0132(9) 0.5081(4) 1.0814(9) 0.0175(10) Uani 1 1 d . . .
H5C H -0.0464 0.4822 1.1649 0.021 Uiso 1 1 calc R . .
C6 C -0.1538(8) 0.7437(4) 0.8734(8) 0.0158(10) Uani 1 1 d . . .
C7 C 0.0066(8) 0.7910(3) 0.8271(8) 0.0152(10) Uani 1 1 d . . .
C8 C -0.0475(8) 0.8186(3) 0.6168(8) 0.0144(10) Uani 1 1 d . . .
C9 C 0.1046(9) 0.8598(4) 0.5716(9) 0.0175(10) Uani 1 1 d . . .
H9 H 0.0649 0.878 0.4281 0.021 Uiso 1 1 calc R . .
C10 C 0.3147(9) 0.8740(4) 0.7388(9) 0.0182(11) Uani 1 1 d . . .
H10 H 0.4187 0.9021 0.708 0.022 Uiso 1 1 calc R . .
C11 C 0.3772(9) 0.8484(4) 0.9494(9) 0.0193(11) Uani 1 1 d . . .
H11 H 0.5225 0.8583 1.0615 0.023 Uiso 1 1 calc R . .
C12 C 0.2225(8) 0.8073(4) 0.9959(8) 0.0156(10) Uani 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.267(6) . ?
O2 C6 1.281(6) . ?
O3 C8 1.368(6) . ?
O3 H3 0.84 . ?
O4 C12 1.351(6) . ?
O4 H4 0.8401 . ?
O5 H5X 0.85(2) . ?
O5 H5Y 0.86(2) . ?
N1 C1 1.340(7) . ?
N1 C4 1.364(7) . ?
N1 H1A 0.88 . ?
N2 C1 1.310(7) . ?
N2 C2 1.360(7) . ?
N3 C5 1.328(7) . ?
N3 C3 1.384(7) . ?
N4 C5 1.360(7) . ?
N4 C2 1.377(7) . ?
N4 H4A 0.88 . ?
N5 C4 1.318(7) . ?
N5 H5A 0.88 . ?
N5 H5B 0.88 . ?
C1 H1 0.95 . ?
C2 C3 1.394(7) . ?
C3 C4 1.408(8) . ?
C5 H5C 0.95 . ?
C6 C7 1.489(7) . ?
C7 C8 1.402(7) . ?
C7 C12 1.420(7) . ?
C8 C9 1.391(8) . ?
C9 C10 1.385(8) . ?
C9 H9 0.95 . ?
C10 C11 1.383(8) . ?
C10 H10 0.95 . ?
C11 C12 1.411(7) . ?
C11 H11 0.95 . ?

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 O3 H3 109.7 . . ?
C12 O4 H4 109.5 . . ?
H5X O5 H5Y 104(3) . . ?
C1 N1 C4 124.2(5) . . ?
C1 N1 H1A 117.9 . . ?
C4 N1 H1A 117.9 . . ?
C1 N2 C2 110.9(5) . . ?
C5 N3 C3 103.1(4) . . ?
C5 N4 C2 106.0(5) . . ?
C5 N4 H4A 127 . . ?
C2 N4 H4A 127 . . ?
C4 N5 H5A 120 . . ?
C4 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
N2 C1 N1 126.4(5) . . ?
N2 C1 H1 116.8 . . ?
N1 C1 H1 116.8 . . ?
N2 C2 N4 127.3(5) . . ?
N2 C2 C3 127.2(5) . . ?
N4 C2 C3 105.5(5) . . ?
N3 C3 C2 111.0(5) . . ?
N3 C3 C4 130.7(5) . . ?
C2 C3 C4 118.2(5) . . ?
N5 C4 N1 120.7(5) . . ?
N5 C4 C3 126.4(5) . . ?
N1 C4 C3 112.9(5) . . ?
N3 C5 N4 114.3(5) . . ?
N3 C5 H5C 122.8 . . ?
N4 C5 H5C 122.8 . . ?
O1 C6 O2 123.0(5) . . ?
O1 C6 C7 118.1(5) . . ?
O2 C6 C7 118.9(5) . . ?
C8 C7 C12 118.1(5) . . ?
C8 C7 C6 121.5(5) . . ?
C12 C7 C6 120.3(5) . . ?
O3 C8 C9 117.4(5) . . ?
O3 C8 C7 121.0(5) . . ?
C9 C8 C7 121.6(5) . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.7(5) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.2(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
O4 C12 C11 118.8(5) . . ?
O4 C12 C7 121.0(5) . . ?
C11 C12 C7 120.2(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
C2 N2 C1 N1 -0.3(8) . . . . ?
C4 N1 C1 N2 1.6(9) . . . . ?
C1 N2 C2 N4 177.1(5) . . . . ?
C1 N2 C2 C3 -0.2(8) . . . . ?
C5 N4 C2 N2 -177.1(5) . . . . ?
C5 N4 C2 C3 0.6(6) . . . . ?
C5 N3 C3 C2 -1.0(6) . . . . ?
C5 N3 C3 C4 177.2(6) . . . . ?
N2 C2 C3 N3 178.0(5) . . . . ?
N4 C2 C3 N3 0.2(6) . . . . ?
N2 C2 C3 C4 -0.5(9) . . . . ?
N4 C2 C3 C4 -178.2(5) . . . . ?
C1 N1 C4 N5 179.2(5) . . . . ?
C1 N1 C4 C3 -2.1(8) . . . . ?
N3 C3 C4 N5 2.1(10) . . . . ?
C2 C3 C4 N5 -179.9(5) . . . . ?
N3 C3 C4 N1 -176.6(5) . . . . ?
C2 C3 C4 N1 1.5(7) . . . . ?
C3 N3 C5 N4 1.4(6) . . . . ?
C2 N4 C5 N3 -1.3(6) . . . . ?
O1 C6 C7 C8 3.3(7) . . . . ?
O2 C6 C7 C8 -177.5(5) . . . . ?
O1 C6 C7 C12 -174.9(5) . . . . ?
O2 C6 C7 C12 4.3(7) . . . . ?
C12 C7 C8 O3 -179.1(5) . . . . ?
C6 C7 C8 O3 2.7(7) . . . . ?
C12 C7 C8 C9 0.8(8) . . . . ?
C6 C7 C8 C9 -177.5(5) . . . . ?
O3 C8 C9 C10 179.8(5) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C8 C9 C10 C11 -0.1(8) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 O4 -178.0(5) . . . . ?
C10 C11 C12 C7 1.2(8) . . . . ?
C8 C7 C12 O4 177.8(5) . . . . ?
C6 C7 C12 O4 -3.9(8) . . . . ?
C8 C7 C12 C11 -1.3(8) . . . . ?
C6 C7 C12 C11 176.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.84 1.85 2.546(5) 138.8 .
O3 H3 O4 0.84 2.44 2.854(5) 111.2 1_454
O4 H4 O2 0.84 1.78 2.533(6) 148 .
N4 H4A O5 0.88 1.83 2.708(6) 178 2_546
N5 H5A O2 0.88 1.9 2.776(6) 176 1_655
N5 H5B N2 0.88 2.42 3.086(6) 132.9 1_656
N1 H1A O1 0.88 1.83 2.714(6) 177.4 1_655
O5 H5X N3 0.85(2) 2.00(3) 2.827(6) 164(6) 2_657
O5 H5Y O3 0.86(2) 2.13(3) 2.942(6) 158(5) 1_655

#--------------------------END OF CIF 4 OF 6-------------------------------

data_adsal
_database_code_depnum_ccdc_archive 'CCDC 686687'

_audit_creation_date             2008-02-12T14:36:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Adenine 2-hydroxybenzoate methanolate
;
_chemical_formula_moiety         
;
C7 H5 O3 1-, C5 H6 N5 1+, C1 H4 O1
;
_chemical_formula_sum            'C13 H15 N5 O4'
_chemical_formula_weight         305.3
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   7.1636(2)
_cell_length_b                   7.9486(3)
_cell_length_c                   24.7336(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.248(2)
_cell_angle_gamma                90
_cell_volume                     1408.01(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3278
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.7372
_exptl_absorpt_correction_T_max  0.9784

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_number            13944
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             3195
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0501P)²+0.6703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.48681(16) 0.51833(15) 0.39528(5) 0.0312(3) Uani 1 1 d . A .
O2 O 0.19373(16) 0.57236(16) 0.41910(5) 0.0338(3) Uani 1 1 d . A .
O3 O 0.5464(2) 0.3186(2) 0.31702(6) 0.0311(5) Uani 0.772(3) 1 d P A 1
H3 H 0.5718 0.382 0.3433 0.037 Uiso 0.772(3) 1 calc PR A 1
O4 O 0.18318(15) 0.09546(17) 0.62256(5) 0.0347(3) Uani 1 1 d . . .
H4 H 0.282 0.0514 0.6116 0.042 Uiso 1 1 calc R . .
N1 N 0.36457(18) 0.31038(17) 0.52030(5) 0.0247(3) Uani 1 1 d . . .
H1 H 0.4103 0.3767 0.5458 0.03 Uiso 1 1 calc R . .
N2 N 0.08719(18) 0.19952(18) 0.48015(6) 0.0266(3) Uani 1 1 d . . .
N3 N 0.47376(18) 0.02351(17) 0.40929(5) 0.0255(3) Uani 1 1 d . . .
N4 N 0.16116(18) 0.00779(17) 0.40694(5) 0.0253(3) Uani 1 1 d . . .
H4A H 0.0481 -0.0235 0.3966 0.03 Uiso 1 1 calc R . .
N5 N 0.66852(18) 0.25377(17) 0.49425(6) 0.0259(3) Uani 1 1 d . . .
H5A H 0.71 0.3212 0.5201 0.031 Uiso 1 1 calc R . .
H5B H 0.7478 0.2024 0.4732 0.031 Uiso 1 1 calc R . .
C1 C 0.1760(2) 0.2931(2) 0.51574(7) 0.0270(4) Uani 1 1 d . . .
H1A H 0.1026 0.3543 0.5405 0.032 Uiso 1 1 calc R . .
C2 C 0.2063(2) 0.1178(2) 0.44726(6) 0.0235(3) Uani 1 1 d . . .
C3 C 0.4004(2) 0.1262(2) 0.44826(6) 0.0232(3) Uani 1 1 d . . .
C4 C 0.4874(2) 0.2297(2) 0.48718(6) 0.0233(3) Uani 1 1 d . . .
C5 C 0.3249(2) -0.0443(2) 0.38575(7) 0.0269(4) Uani 1 1 d . . .
H5C H 0.3315 -0.1223 0.3567 0.032 Uiso 1 1 calc R . .
C6 C 0.2395(2) 0.3889(2) 0.34516(6) 0.0255(3) Uani 1 1 d . A .
C7 C 0.3623(2) 0.3017(2) 0.31182(7) 0.0291(4) Uani 1 1 d . . .
H7 H 0.4933 0.3153 0.3169 0.035 Uiso 0.228(3) 1 calc PR A 2
C8 C 0.2931(3) 0.1953(2) 0.27129(7) 0.0353(4) Uani 1 1 d . A .
H8 H 0.3769 0.1357 0.249 0.042 Uiso 1 1 calc R . .
C9 C 0.1035(3) 0.1767(2) 0.26360(7) 0.0375(4) Uani 1 1 d . . .
H9 H 0.057 0.1054 0.2356 0.045 Uiso 1 1 calc R A .
C10 C -0.0210(3) 0.2610(2) 0.29639(8) 0.0364(4) Uani 1 1 d . A .
H10 H -0.1518 0.2467 0.2911 0.044 Uiso 1 1 calc R . .
C11 C 0.0472(2) 0.3658(2) 0.33671(7) 0.0301(4) Uani 1 1 d . . .
H11 H -0.0378 0.4233 0.3592 0.036 Uiso 0.772(3) 1 calc PR A 1
C12 C 0.3097(2) 0.5011(2) 0.38958(7) 0.0269(4) Uani 1 1 d . . .
C13 C 0.2139(3) 0.1599(3) 0.67547(8) 0.0490(6) Uani 1 1 d . . .
H13A H 0.2823 0.2664 0.6735 0.059 Uiso 1 1 calc R . .
H13B H 0.2872 0.0788 0.6969 0.059 Uiso 1 1 calc R . .
H13C H 0.0936 0.1789 0.6926 0.059 Uiso 1 1 calc R . .
O31 O -0.0669(10) 0.4366(10) 0.3650(3) 0.059 Uiso 0.228(3) 1 d P A 2
H31 H -0.0106 0.4922 0.3892 0.059 Uiso 0.228(3) 1 calc PR A 2


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C12 1.281(2) . ?
O2 C12 1.253(2) . ?
O3 C7 1.329(2) . ?
O3 H3 0.84 . ?
O4 C13 1.418(2) . ?
O4 H4 0.84 . ?
N1 C1 1.360(2) . ?
N1 C4 1.374(2) . ?
N1 H1 0.88 . ?
N2 C1 1.307(2) . ?
N2 C2 1.357(2) . ?
N3 C5 1.319(2) . ?
N3 C3 1.376(2) . ?
N4 C5 1.360(2) . ?
N4 C2 1.360(2) . ?
N4 H4A 0.88 . ?
N5 C4 1.319(2) . ?
N5 H5A 0.88 . ?
N5 H5B 0.88 . ?
C1 H1A 0.95 . ?
C2 C3 1.392(2) . ?
C3 C4 1.402(2) . ?
C5 H5C 0.95 . ?
C6 C11 1.400(2) . ?
C6 C7 1.402(2) . ?
C6 C12 1.494(2) . ?
C7 C8 1.394(2) . ?
C7 H7 0.95 . ?
C8 C9 1.376(3) . ?
C8 H8 0.95 . ?
C9 C10 1.391(3) . ?
C9 H9 0.95 . ?
C10 C11 1.381(3) . ?
C10 H10 0.95 . ?
C11 O31 1.225(7) . ?
C11 H11 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
O31 H31 0.84 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3 109.5 . . ?
C13 O4 H4 109.5 . . ?
C1 N1 C4 123.46(14) . . ?
C1 N1 H1 118.3 . . ?
C4 N1 H1 118.3 . . ?
C1 N2 C2 111.90(13) . . ?
C5 N3 C3 103.55(13) . . ?
C5 N4 C2 106.58(13) . . ?
C5 N4 H4A 126.7 . . ?
C2 N4 H4A 126.7 . . ?
C4 N5 H5A 120 . . ?
C4 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
N2 C1 N1 125.55(16) . . ?
N2 C1 H1A 117.2 . . ?
N1 C1 H1A 117.2 . . ?
N2 C2 N4 127.24(14) . . ?
N2 C2 C3 127.38(15) . . ?
N4 C2 C3 105.37(14) . . ?
N3 C3 C2 110.85(14) . . ?
N3 C3 C4 131.15(14) . . ?
C2 C3 C4 117.99(14) . . ?
N5 C4 N1 119.60(14) . . ?
N5 C4 C3 126.68(15) . . ?
N1 C4 C3 113.71(13) . . ?
N3 C5 N4 113.65(15) . . ?
N3 C5 H5C 123.2 . . ?
N4 C5 H5C 123.2 . . ?
C11 C6 C7 118.37(15) . . ?
C11 C6 C12 120.16(15) . . ?
C7 C6 C12 121.46(15) . . ?
O3 C7 C8 117.83(16) . . ?
O3 C7 C6 121.84(16) . . ?
C8 C7 C6 120.33(16) . . ?
O3 C7 H7 2.1 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.92(17) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C8 C9 C10 120.78(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.37(17) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O31 C11 C10 117.4(4) . . ?
O31 C11 C6 121.4(4) . . ?
C10 C11 C6 121.24(16) . . ?
O31 C11 H11 2 . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O2 C12 O1 123.74(15) . . ?
O2 C12 C6 118.77(14) . . ?
O1 C12 C6 117.49(15) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O31 H31 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
C2 N2 C1 N1 0.3(2) . . . . ?
C4 N1 C1 N2 0.1(3) . . . . ?
C1 N2 C2 N4 178.29(15) . . . . ?
C1 N2 C2 C3 -0.4(2) . . . . ?
C5 N4 C2 N2 -178.95(15) . . . . ?
C5 N4 C2 C3 -0.05(17) . . . . ?
C5 N3 C3 C2 -0.05(17) . . . . ?
C5 N3 C3 C4 178.75(17) . . . . ?
N2 C2 C3 N3 178.97(15) . . . . ?
N4 C2 C3 N3 0.06(17) . . . . ?
N2 C2 C3 C4 0.0(2) . . . . ?
N4 C2 C3 C4 -178.92(14) . . . . ?
C1 N1 C4 N5 179.81(15) . . . . ?
C1 N1 C4 C3 -0.5(2) . . . . ?
N3 C3 C4 N5 1.4(3) . . . . ?
C2 C3 C4 N5 -179.89(15) . . . . ?
N3 C3 C4 N1 -178.30(15) . . . . ?
C2 C3 C4 N1 0.4(2) . . . . ?
C3 N3 C5 N4 0.02(18) . . . . ?
C2 N4 C5 N3 0.02(19) . . . . ?
C11 C6 C7 O3 179.30(16) . . . . ?
C12 C6 C7 O3 -2.0(3) . . . . ?
C11 C6 C7 C8 0.1(2) . . . . ?
C12 C6 C7 C8 178.80(15) . . . . ?
O3 C7 C8 C9 -178.60(17) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 O31 -179.4(4) . . . . ?
C9 C10 C11 C6 0.1(3) . . . . ?
C7 C6 C11 O31 179.0(4) . . . . ?
C12 C6 C11 O31 0.3(5) . . . . ?
C7 C6 C11 C10 -0.5(3) . . . . ?
C12 C6 C11 C10 -179.16(16) . . . . ?
C11 C6 C12 O2 0.6(2) . . . . ?
C7 C6 C12 O2 -178.05(15) . . . . ?
C11 C6 C12 O1 -179.65(15) . . . . ?
C7 C6 C12 O1 1.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.84 1.8 2.547(2) 147.6 .
O31 H31 O2 0.84 1.75 2.516(7) 151.5 .
O4 H4 N3 0.84 1.93 2.7638(17) 172.1 3_656
N1 H1 O1 0.88 1.82 2.6927(18) 170.4 3_666
N5 H5A O2 0.88 1.85 2.7174(18) 169.8 3_666
N5 H5B N2 0.88 2.43 3.0575(19) 128.3 1_655
N4 H4A O4 0.88 1.81 2.6855(17) 177.5 3_556

#--------------------------END OF CIF 5 OF 6-----------------------------

data_ad35
_database_code_depnum_ccdc_archive 'CCDC 686688'

_audit_creation_date             2008-02-12T11:15:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
[Adenine hydroxide] [3,5-dihydroxybenzoic acid hydrate]
;
_chemical_formula_moiety         
;
C7 H5 O4 1-, C5 H6 N5 1+, H3 O1 1+, H1 O1 1-'
;
_chemical_formula_sum            'C12 H15 N5 O6'
_chemical_formula_weight         325.29
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.6347(5)
_cell_length_b                   14.9993(8)
_cell_length_c                   7.9794(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.496(3)
_cell_angle_gamma                90
_cell_volume                     1392.03(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_absorpt_correction_T_min  0.8668
_exptl_absorpt_correction_T_max  0.9924

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device_type  
;
Bruker-Nonius KappaCCD Area Detector
;
_diffrn_measurement_method       
;
φ and ω scans
;
_diffrn_standards_number         0
_diffrn_standards_decay_%        negligible
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_number            6421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             1599
_reflns_number_gt                1403
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0328P)²+3.9257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1599
_refine_ls_number_parameters     223
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.38
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2331(3) 0.5445(2) 0.5558(4) 0.0228(7) Uani 1 1 d . . .
O2 O 0.0751(3) 0.5109(2) 0.6924(4) 0.0251(8) Uani 1 1 d . . .
O3 O 0.0610(3) 0.1768(2) 0.7177(5) 0.0260(8) Uani 1 1 d . . .
H3 H 0.0124 0.2029 0.7763 0.031 Uiso 1 1 calc R . .
O4 O 0.3782(3) 0.2407(2) 0.3719(4) 0.0228(7) Uani 1 1 d . . .
H4 H 0.3752 0.185 0.361 0.027 Uiso 1 1 calc R . .
C6 C 0.1632(4) 0.4887(3) 0.6124(6) 0.0177(10) Uani 1 1 d . . .
C7 C 0.1850(4) 0.3902(3) 0.5878(6) 0.0180(9) Uani 1 1 d . . .
C8 C 0.1132(4) 0.3296(3) 0.6655(6) 0.0181(9) Uani 1 1 d . . .
H8 H 0.0533 0.3504 0.7342 0.022 Uiso 1 1 calc R . .
C9 C 0.1290(4) 0.2386(3) 0.6427(6) 0.0188(10) Uani 1 1 d . . .
C10 C 0.2181(4) 0.2073(3) 0.5449(5) 0.0166(9) Uani 1 1 d . . .
H10 H 0.2307 0.1451 0.5315 0.02 Uiso 1 1 calc R . .
C11 C 0.2879(4) 0.2691(3) 0.4677(6) 0.0180(9) Uani 1 1 d . . .
C12 C 0.2721(4) 0.3600(3) 0.4871(6) 0.0172(9) Uani 1 1 d . . .
H12 H 0.3204 0.4012 0.4321 0.021 Uiso 1 1 calc R . .
N1 N 0.0187(3) 0.3214(3) 0.2433(5) 0.0200(9) Uani 1 1 d . . .
H1 H 0.0417 0.3757 0.2193 0.024 Uiso 1 1 calc R . .
N2 N -0.1151(3) 0.2370(3) 0.3973(5) 0.0183(8) Uani 1 1 d . . .
N3 N 0.0570(3) 0.0822(3) 0.1695(5) 0.0227(9) Uani 1 1 d . . .
N4 N -0.0870(3) 0.0781(3) 0.3494(5) 0.0203(9) Uani 1 1 d . . .
H4A H -0.1406 0.0561 0.4132 0.024 Uiso 1 1 calc R . .
N5 N 0.1619(3) 0.2670(3) 0.0766(5) 0.0233(9) Uani 1 1 d . . .
H5A H 0.1844 0.3221 0.0593 0.028 Uiso 1 1 calc R . .
H5B H 0.1983 0.2223 0.0299 0.028 Uiso 1 1 calc R . .
C1 C -0.0697(4) 0.3121(3) 0.3488(6) 0.0201(10) Uani 1 1 d . . .
H1A H -0.1019 0.3653 0.3919 0.024 Uiso 1 1 calc R . .
C2 C -0.0623(4) 0.1659(3) 0.3270(5) 0.0181(10) Uani 1 1 d . . .
C3 C 0.0273(4) 0.1676(3) 0.2155(6) 0.0176(9) Uani 1 1 d . . .
C4 C 0.0741(4) 0.2513(3) 0.1719(6) 0.0169(9) Uani 1 1 d . . .
C5 C -0.0127(5) 0.0307(3) 0.2541(6) 0.0249(10) Uani 1 1 d . . .
H5C H -0.0115 -0.0326 0.2493 0.03 Uiso 1 1 calc R . .
O6 O 0.2720(4) 0.0481(3) 0.0368(5) 0.0374(10) Uani 1 1 d D . .
H6A H 0.302(4) 0.054(4) 0.137(4) 0.045 Uiso 1 1 d D . .
H6B H 0.1991(17) 0.041(4) 0.047(6) 0.045 Uiso 1 1 d D . .
H6C H 0.303(4) 0.006(3) -0.016(6) 0.045 Uiso 1 1 d D . .
O5 O 0.3876(3) 0.0632(3) 0.3411(5) 0.0352(10) Uani 1 1 d D . .
H5X H 0.454(3) 0.043(4) 0.314(8) 0.042 Uiso 1 1 d D . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.259(6) . ?
O2 C6 1.266(5) . ?
O3 C9 1.367(5) . ?
O3 H3 0.84 . ?
O4 C11 1.383(5) . ?
O4 H4 0.84 . ?
C6 C7 1.512(7) . ?
C7 C12 1.386(6) . ?
C7 C8 1.391(6) . ?
C8 C9 1.390(6) . ?
C8 H8 0.95 . ?
C9 C10 1.395(7) . ?
C10 C11 1.388(6) . ?
C10 H10 0.95 . ?
C11 C12 1.385(7) . ?
C12 H12 0.95 . ?
N1 C1 1.354(6) . ?
N1 C4 1.366(6) . ?
N1 H1 0.88 . ?
N2 C1 1.307(6) . ?
N2 C2 1.359(6) . ?
N3 C5 1.319(6) . ?
N3 C3 1.379(6) . ?
N4 C2 1.360(6) . ?
N4 C5 1.365(6) . ?
N4 H4A 0.88 . ?
N5 C4 1.310(6) . ?
N5 H5A 0.88 . ?
N5 H5B 0.88 . ?
C1 H1A 0.95 . ?
C2 C3 1.388(6) . ?
C3 C4 1.416(6) . ?
C5 H5C 0.95 . ?
O6 H6A 0.869(19) . ?
O6 H6B 0.861(19) . ?
O6 H6C 0.843(19) . ?
O5 H5X 0.86(2) . ?

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
C9 O3 H3 109.5 . . ?
C11 O4 H4 109.5 . . ?
O1 C6 O2 123.0(4) . . ?
O1 C6 C7 119.4(4) . . ?
O2 C6 C7 117.5(4) . . ?
C12 C7 C8 120.1(4) . . ?
C12 C7 C6 121.4(4) . . ?
C8 C7 C6 118.4(4) . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
O3 C9 C8 121.9(4) . . ?
O3 C9 C10 117.6(4) . . ?
C8 C9 C10 120.5(4) . . ?
C11 C10 C9 118.4(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
O4 C11 C12 118.1(4) . . ?
O4 C11 C10 120.1(4) . . ?
C12 C11 C10 121.8(4) . . ?
C11 C12 C7 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C1 N1 C4 123.7(4) . . ?
C1 N1 H1 118.2 . . ?
C4 N1 H1 118.2 . . ?
C1 N2 C2 111.3(4) . . ?
C5 N3 C3 104.2(4) . . ?
C2 N4 C5 107.0(4) . . ?
C2 N4 H4A 126.5 . . ?
C5 N4 H4A 126.5 . . ?
C4 N5 H5A 120 . . ?
C4 N5 H5B 120 . . ?
H5A N5 H5B 120 . . ?
N2 C1 N1 126.4(5) . . ?
N2 C1 H1A 116.8 . . ?
N1 C1 H1A 116.8 . . ?
N2 C2 N4 127.3(4) . . ?
N2 C2 C3 127.3(5) . . ?
N4 C2 C3 105.4(4) . . ?
N3 C3 C2 110.6(4) . . ?
N3 C3 C4 131.1(4) . . ?
C2 C3 C4 118.3(4) . . ?
N5 C4 N1 119.2(4) . . ?
N5 C4 C3 127.8(4) . . ?
N1 C4 C3 113.1(4) . . ?
N3 C5 N4 112.7(4) . . ?
N3 C5 H5C 123.6 . . ?
N4 C5 H5C 123.6 . . ?
H6A O6 H6B 107(3) . . ?
H6A O6 H6C 112(3) . . ?
H6B O6 H6C 113(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C7 C12 -8.0(7) . . . . ?
O2 C6 C7 C12 173.1(4) . . . . ?
O1 C6 C7 C8 173.7(5) . . . . ?
O2 C6 C7 C8 -5.2(6) . . . . ?
C12 C7 C8 C9 0.2(7) . . . . ?
C6 C7 C8 C9 178.6(5) . . . . ?
C7 C8 C9 O3 179.5(5) . . . . ?
C7 C8 C9 C10 1.3(8) . . . . ?
O3 C9 C10 C11 179.9(4) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C9 C10 C11 O4 179.0(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
O4 C11 C12 C7 -177.5(4) . . . . ?
C10 C11 C12 C7 0.7(7) . . . . ?
C8 C7 C12 C11 -1.2(7) . . . . ?
C6 C7 C12 C11 -179.5(5) . . . . ?
C2 N2 C1 N1 -0.3(7) . . . . ?
C4 N1 C1 N2 -0.3(8) . . . . ?
C1 N2 C2 N4 180.0(5) . . . . ?
C1 N2 C2 C3 -0.9(6) . . . . ?
C5 N4 C2 N2 179.7(5) . . . . ?
C5 N4 C2 C3 0.5(5) . . . . ?
C5 N3 C3 C2 -0.8(6) . . . . ?
C5 N3 C3 C4 177.3(5) . . . . ?
N2 C2 C3 N3 -179.1(4) . . . . ?
N4 C2 C3 N3 0.2(5) . . . . ?
N2 C2 C3 C4 2.6(7) . . . . ?
N4 C2 C3 C4 -178.2(4) . . . . ?
C1 N1 C4 N5 -177.2(5) . . . . ?
C1 N1 C4 C3 1.8(6) . . . . ?
N3 C3 C4 N5 -1.8(8) . . . . ?
C2 C3 C4 N5 176.2(5) . . . . ?
N3 C3 C4 N1 179.3(5) . . . . ?
C2 C3 C4 N1 -2.8(6) . . . . ?
C3 N3 C5 N4 1.1(6) . . . . ?
C2 N4 C5 N3 -1.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.84 1.95 2.776(5) 168.1 4_455
O4 H4 O5 0.84 1.84 2.675(5) 173 .
N1 H1 O2 0.88 1.76 2.634(5) 172.2 2_564
N4 H4A O1 0.88 1.89 2.744(5) 163.1 3_445
N5 H5A O1 0.88 2.08 2.952(5) 171.5 2_564
N5 H5B N2 0.88 2.52 2.996(5) 115.1 4_554
O6 H6A O5 0.869(19) 1.89(2) 2.754(6) 172(5) .
O6 H6B N3 0.861(19) 2.04(3) 2.789(5) 145(5) .
O6 H6C O5 0.843(19) 1.85(2) 2.673(5) 167(6) 2_554
O5 H5X O2 0.86(2) 1.92(3) 2.745(5) 162(6) 4_554

#------------------------END OF CIF 6 OF 6------------------------------



