# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010


data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Schultheiss, Nathan'
'Roe, Melanie'
'Boerrigter, Stephan'

_publ_contact_author_name        'Schultheiss, Nathan'
_publ_contact_author_email       nathan.schultheiss@aptuit.com

_publ_section_title              
;
Cocrystals of nutraceutical p-coumaric acid with caffeine and theophylline
;

# Attachment '- 1.cif'

data_205596
_database_code_depnum_ccdc_archive 'CCDC 778271'
#TrackingRef '- 1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
205596 (3631-97-01)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H10 N4 O2) (C9 H8 O3)
;
_chemical_formula_sum            'C17 H18 N4 O5'
_chemical_formula_weight         358.35

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.5225(4)
_cell_length_b                   10.6474(6)
_cell_length_c                   23.2444(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.983(2)
_cell_angle_gamma                90.00
_cell_volume                     1610.37(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9394
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      32.14

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18365
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         32.14
_reflns_number_total             5512
_reflns_number_gt                4533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5512
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.19382(14) 0.21439(8) 0.04239(4) 0.02182(17) Uani 1 1 d . . .
C11 C -0.30228(19) 0.10192(11) 0.02059(5) 0.0297(2) Uani 1 1 d . . .
H11A H -0.4089 0.0795 0.0465 0.044 Uiso 1 1 calc R . .
H11B H -0.2046 0.0323 0.0188 0.044 Uiso 1 1 calc R . .
H11C H -0.3659 0.1186 -0.0181 0.044 Uiso 1 1 calc R . .
C12 C -0.01538(17) 0.24447(10) 0.01562(4) 0.0237(2) Uani 1 1 d . . .
O12 O 0.04358(14) 0.18082(9) -0.02316(4) 0.0331(2) Uani 1 1 d . . .
N13 N 0.08888(13) 0.35020(9) 0.03493(4) 0.02264(18) Uani 1 1 d . . .
C13 C 0.27579(17) 0.38489(12) 0.00821(5) 0.0294(2) Uani 1 1 d . . .
H13A H 0.3421 0.4552 0.0294 0.044 Uiso 1 1 calc R . .
H13B H 0.2416 0.4099 -0.0319 0.044 Uiso 1 1 calc R . .
H13C H 0.3696 0.3129 0.0091 0.044 Uiso 1 1 calc R . .
C14 C 0.01811(15) 0.41835(9) 0.07892(4) 0.01988(18) Uani 1 1 d . . .
C15 C -0.15436(15) 0.38444(9) 0.10545(4) 0.01945(18) Uani 1 1 d . . .
C16 C -0.27370(15) 0.27821(9) 0.08800(4) 0.01998(18) Uani 1 1 d . . .
O16 O -0.43323(12) 0.24290(8) 0.10791(3) 0.02621(17) Uani 1 1 d . . .
N17 N -0.17814(13) 0.47517(8) 0.14683(4) 0.02223(18) Uani 1 1 d . . .
C17 C -0.33309(17) 0.47987(11) 0.18902(5) 0.0283(2) Uani 1 1 d . . .
H17A H -0.3106 0.5544 0.2134 0.042 Uiso 1 1 calc R . .
H17B H -0.3228 0.4043 0.2131 0.042 Uiso 1 1 calc R . .
H17C H -0.4701 0.4840 0.1690 0.042 Uiso 1 1 calc R . .
C18 C -0.02360(16) 0.55623(11) 0.14253(5) 0.0250(2) Uani 1 1 d . . .
H18 H -0.0039 0.6283 0.1664 0.030 Uiso 1 1 calc R . .
N19 N 0.10011(14) 0.52575(9) 0.10148(4) 0.02353(18) Uani 1 1 d . . .
C21 C 0.84084(15) 1.01063(10) 0.17849(4) 0.02118(19) Uani 1 1 d . . .
C22 C 1.00754(15) 1.00047(10) 0.14430(4) 0.0228(2) Uani 1 1 d . . .
H22 H 1.0147 0.9317 0.1185 0.027 Uiso 1 1 calc R . .
C23 C 1.16258(15) 1.08934(10) 0.14756(5) 0.0236(2) Uani 1 1 d . . .
H23 H 1.2755 1.0813 0.1241 0.028 Uiso 1 1 calc R . .
C24 C 1.15312(15) 1.19030(10) 0.18508(4) 0.02190(19) Uani 1 1 d . . .
O24 O 1.29877(13) 1.28084(8) 0.18956(4) 0.03089(19) Uani 1 1 d . . .
H24 H 1.389(3) 1.2643(16) 0.1643(8) 0.037 Uiso 1 1 d . . .
C25 C 0.98986(16) 1.20087(10) 0.22010(4) 0.0230(2) Uani 1 1 d . . .
H25 H 0.9841 1.2691 0.2463 0.028 Uiso 1 1 calc R . .
C26 C 0.83632(16) 1.11167(10) 0.21665(4) 0.0232(2) Uani 1 1 d . . .
H26 H 0.7251 1.1191 0.2407 0.028 Uiso 1 1 calc R . .
C27 C 0.66959(15) 0.92281(10) 0.17461(4) 0.02273(19) Uani 1 1 d . . .
H27 H 0.5760 0.9281 0.2041 0.027 Uiso 1 1 calc R . .
C28 C 0.62994(15) 0.83566(10) 0.13412(5) 0.0237(2) Uani 1 1 d . . .
H28 H 0.7205 0.8252 0.1042 0.028 Uiso 1 1 calc R . .
C29 C 0.44673(16) 0.75590(10) 0.13566(4) 0.0229(2) Uani 1 1 d . . .
O29 O 0.42563(13) 0.67860(8) 0.09027(4) 0.02949(19) Uani 1 1 d . . .
H29 H 0.307(2) 0.6322(15) 0.0930(7) 0.035 Uiso 1 1 d . . .
O30 O 0.32610(12) 0.75786(8) 0.17290(4) 0.02884(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N11 0.0252(4) 0.0196(4) 0.0211(4) -0.0027(3) 0.0045(3) -0.0036(3)
C11 0.0367(6) 0.0219(5) 0.0307(5) -0.0062(4) 0.0043(4) -0.0077(4)
C12 0.0265(5) 0.0225(5) 0.0227(5) -0.0007(3) 0.0057(4) 0.0000(4)
O12 0.0397(5) 0.0297(4) 0.0314(4) -0.0085(3) 0.0135(4) -0.0001(3)
N13 0.0223(4) 0.0247(4) 0.0219(4) -0.0016(3) 0.0082(3) -0.0026(3)
C13 0.0235(5) 0.0380(6) 0.0280(5) 0.0033(4) 0.0108(4) -0.0008(4)
C14 0.0202(4) 0.0206(4) 0.0190(4) 0.0004(3) 0.0033(3) -0.0020(3)
C15 0.0210(4) 0.0196(4) 0.0181(4) -0.0017(3) 0.0041(3) -0.0024(3)
C16 0.0209(4) 0.0206(4) 0.0185(4) 0.0006(3) 0.0020(3) -0.0015(3)
O16 0.0236(4) 0.0290(4) 0.0265(4) -0.0009(3) 0.0059(3) -0.0075(3)
N17 0.0225(4) 0.0240(4) 0.0210(4) -0.0039(3) 0.0066(3) -0.0045(3)
C17 0.0272(5) 0.0312(6) 0.0277(5) -0.0069(4) 0.0118(4) -0.0042(4)
C18 0.0256(5) 0.0255(5) 0.0244(5) -0.0053(4) 0.0051(4) -0.0066(4)
N19 0.0235(4) 0.0247(4) 0.0228(4) -0.0024(3) 0.0043(3) -0.0063(3)
C21 0.0209(4) 0.0236(5) 0.0195(4) 0.0008(3) 0.0044(3) -0.0023(3)
C22 0.0218(4) 0.0234(5) 0.0241(5) -0.0024(3) 0.0065(3) -0.0017(3)
C23 0.0207(4) 0.0263(5) 0.0245(5) -0.0020(4) 0.0070(3) -0.0025(4)
C24 0.0209(4) 0.0240(5) 0.0210(4) 0.0004(3) 0.0027(3) -0.0036(3)
O24 0.0283(4) 0.0322(4) 0.0333(4) -0.0080(3) 0.0101(3) -0.0119(3)
C25 0.0245(5) 0.0243(5) 0.0204(4) -0.0026(3) 0.0042(3) -0.0010(4)
C26 0.0228(4) 0.0273(5) 0.0204(4) -0.0018(3) 0.0067(3) -0.0011(4)
C27 0.0217(4) 0.0251(5) 0.0221(4) 0.0016(3) 0.0066(3) -0.0024(3)
C28 0.0220(4) 0.0250(5) 0.0248(5) 0.0000(4) 0.0079(3) -0.0052(4)
C29 0.0230(4) 0.0224(5) 0.0238(5) 0.0019(3) 0.0056(4) -0.0036(3)
O29 0.0282(4) 0.0318(4) 0.0297(4) -0.0067(3) 0.0114(3) -0.0118(3)
O30 0.0277(4) 0.0317(4) 0.0285(4) -0.0023(3) 0.0122(3) -0.0080(3)

_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
N11 C16 1.3908(13) . ?
N11 C12 1.3946(13) . ?
N11 C11 1.4633(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O12 1.2116(13) . ?
C12 N13 1.3743(14) . ?
N13 C14 1.3605(13) . ?
N13 C13 1.4537(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N19 1.3527(13) . ?
C14 C15 1.3683(13) . ?
C15 N17 1.3796(12) . ?
C15 C16 1.4163(13) . ?
C16 O16 1.2268(12) . ?
N17 C18 1.3360(13) . ?
N17 C17 1.4572(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N19 1.3319(13) . ?
C18 H18 0.9500 . ?
C21 C22 1.3948(14) . ?
C21 C26 1.3960(14) . ?
C21 C27 1.4547(14) . ?
C22 C23 1.3831(14) . ?
C22 H22 0.9500 . ?
C23 C24 1.3882(15) . ?
C23 H23 0.9500 . ?
C24 O24 1.3524(12) . ?
C24 C25 1.3892(14) . ?
O24 H24 0.879(18) . ?
C25 C26 1.3784(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.3341(15) . ?
C27 H27 0.9500 . ?
C28 C29 1.4685(14) . ?
C28 H28 0.9500 . ?
C29 O30 1.2098(12) . ?
C29 O29 1.3375(13) . ?
O29 H29 0.925(16) . ?

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
C16 N11 C12 126.61(9) . . ?
C16 N11 C11 117.78(9) . . ?
C12 N11 C11 115.59(9) . . ?
N11 C11 H11A 109.5 . . ?
N11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C12 N13 121.71(10) . . ?
O12 C12 N11 121.42(10) . . ?
N13 C12 N11 116.87(9) . . ?
C14 N13 C12 119.75(9) . . ?
C14 N13 C13 121.60(9) . . ?
C12 N13 C13 118.64(9) . . ?
N13 C13 H13A 109.5 . . ?
N13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N13 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N19 C14 N13 126.63(9) . . ?
N19 C14 C15 111.32(9) . . ?
N13 C14 C15 122.04(9) . . ?
C14 C15 N17 105.38(8) . . ?
C14 C15 C16 122.30(9) . . ?
N17 C15 C16 132.28(9) . . ?
O16 C16 N11 120.69(9) . . ?
O16 C16 C15 126.90(9) . . ?
N11 C16 C15 112.39(9) . . ?
C18 N17 C15 106.16(8) . . ?
C18 N17 C17 126.18(9) . . ?
C15 N17 C17 127.60(9) . . ?
N17 C17 H17A 109.5 . . ?
N17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N19 C18 N17 113.20(9) . . ?
N19 C18 H18 123.4 . . ?
N17 C18 H18 123.4 . . ?
C18 N19 C14 103.94(8) . . ?
C22 C21 C26 118.26(9) . . ?
C22 C21 C27 122.72(9) . . ?
C26 C21 C27 118.99(9) . . ?
C23 C22 C21 120.77(10) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.00(9) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
O24 C24 C23 122.59(9) . . ?
O24 C24 C25 117.39(9) . . ?
C23 C24 C25 120.01(9) . . ?
C24 O24 H24 107.8(11) . . ?
C26 C25 C24 119.57(10) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C21 121.37(9) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C28 C27 C21 126.95(9) . . ?
C28 C27 H27 116.5 . . ?
C21 C27 H27 116.5 . . ?
C27 C28 C29 120.22(9) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
O30 C29 O29 122.59(10) . . ?
O30 C29 C28 125.33(10) . . ?
O29 C29 C28 112.09(9) . . ?
C29 O29 H29 108.4(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
C16 N11 C12 O12 178.35(10) . . . . ?
C11 N11 C12 O12 0.16(15) . . . . ?
C16 N11 C12 N13 -2.28(16) . . . . ?
C11 N11 C12 N13 179.53(9) . . . . ?
O12 C12 N13 C14 -179.45(10) . . . . ?
N11 C12 N13 C14 1.18(14) . . . . ?
O12 C12 N13 C13 -0.68(16) . . . . ?
N11 C12 N13 C13 179.96(9) . . . . ?
C12 N13 C14 N19 -178.08(10) . . . . ?
C13 N13 C14 N19 3.18(16) . . . . ?
C12 N13 C14 C15 0.66(15) . . . . ?
C13 N13 C14 C15 -178.08(10) . . . . ?
N19 C14 C15 N17 -0.60(12) . . . . ?
N13 C14 C15 N17 -179.52(9) . . . . ?
N19 C14 C15 C16 177.25(9) . . . . ?
N13 C14 C15 C16 -1.67(16) . . . . ?
C12 N11 C16 O16 179.72(10) . . . . ?
C11 N11 C16 O16 -2.12(15) . . . . ?
C12 N11 C16 C15 1.33(15) . . . . ?
C11 N11 C16 C15 179.48(9) . . . . ?
C14 C15 C16 O16 -177.60(10) . . . . ?
N17 C15 C16 O16 -0.40(19) . . . . ?
C14 C15 C16 N11 0.67(14) . . . . ?
N17 C15 C16 N11 177.87(10) . . . . ?
C14 C15 N17 C18 0.36(11) . . . . ?
C16 C15 N17 C18 -177.18(11) . . . . ?
C14 C15 N17 C17 -176.78(10) . . . . ?
C16 C15 N17 C17 5.68(18) . . . . ?
C15 N17 C18 N19 -0.01(13) . . . . ?
C17 N17 C18 N19 177.18(10) . . . . ?
N17 C18 N19 C14 -0.35(12) . . . . ?
N13 C14 N19 C18 179.44(10) . . . . ?
C15 C14 N19 C18 0.59(12) . . . . ?
C26 C21 C22 C23 -0.97(16) . . . . ?
C27 C21 C22 C23 177.05(10) . . . . ?
C21 C22 C23 C24 -0.16(16) . . . . ?
C22 C23 C24 O24 -179.13(10) . . . . ?
C22 C23 C24 C25 1.17(16) . . . . ?
O24 C24 C25 C26 179.28(10) . . . . ?
C23 C24 C25 C26 -1.01(16) . . . . ?
C24 C25 C26 C21 -0.16(16) . . . . ?
C22 C21 C26 C25 1.14(16) . . . . ?
C27 C21 C26 C25 -176.96(10) . . . . ?
C22 C21 C27 C28 -10.93(17) . . . . ?
C26 C21 C27 C28 167.08(11) . . . . ?
C21 C27 C28 C29 -178.53(10) . . . . ?
C27 C28 C29 O30 -3.12(17) . . . . ?
C27 C28 C29 O29 176.75(10) . . . . ?

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
O29 H29 N19 0.925(16) 1.783(16) 2.7021(12) 172.3(15) .
O24 H24 O16 0.879(18) 1.822(19) 2.6984(12) 174.6(17) 1_765

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        32.14
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056

# Attachment '- 2.cif'

data_205289
_database_code_depnum_ccdc_archive 'CCDC 778272'
#TrackingRef '- 2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3631-86-02 (205289)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H10 N4 O2)2 (C9 H8 O3) (O)0.2
;
_chemical_formula_sum            'C25 H28 N8 O7.20'
_chemical_formula_weight         555.75

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.1475(7)
_cell_length_b                   11.2176(9)
_cell_length_c                   14.8517(13)
_cell_angle_alpha                75.956(2)
_cell_angle_beta                 84.712(2)
_cell_angle_gamma                73.340(2)
_cell_volume                     1261.16(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      32.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             583
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26213
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         32.59
_reflns_number_total             8113
_reflns_number_gt                6433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8113
_refine_ls_number_parameters     435
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O 0.8223(13) 0.8747(9) 1.1411(7) 0.080(3) Uiso 0.20 1 d P . .
N11_1 N 0.95406(14) 0.41206(11) -0.33445(8) 0.0245(2) Uani 1 1 d D A 1
C11_1 C 1.08289(19) 0.34854(15) -0.39539(11) 0.0330(3) Uani 1 1 d D A 1
H11A_1 H 1.1527 0.2677 -0.3591 0.050 Uiso 1 1 calc R A 1
H11B_1 H 1.1566 0.4038 -0.4236 0.050 Uiso 1 1 calc R A 1
H11C_1 H 1.0257 0.3316 -0.4443 0.050 Uiso 1 1 calc R A 1
C12_1 C 1.01295(16) 0.41604(13) -0.25051(10) 0.0262(3) Uani 1 1 d D A 1
O12_1 O 1.16348(13) 0.36978(12) -0.23106(8) 0.0383(3) Uani 1 1 d D A 1
N13_1 N 0.89460(14) 0.47509(11) -0.19149(8) 0.0245(2) Uani 1 1 d D A 1
C13_1 C 0.94752(19) 0.48108(15) -0.10166(10) 0.0311(3) Uani 1 1 d D A 1
H13A_1 H 0.9149 0.5702 -0.0961 0.047 Uiso 1 1 calc R A 1
H13B_1 H 1.0721 0.4461 -0.0970 0.047 Uiso 1 1 calc R A 1
H13C_1 H 0.8911 0.4309 -0.0517 0.047 Uiso 1 1 calc R A 1
C14_1 C 0.72527(16) 0.52133(12) -0.21521(9) 0.0219(2) Uani 1 1 d D A 1
C15_1 C 0.67093(15) 0.51414(12) -0.29803(9) 0.0219(2) Uani 1 1 d D A 1
C16_1 C 0.78345(16) 0.45963(12) -0.36499(9) 0.0236(2) Uani 1 1 d D A 1
O16_1 O 0.74448(14) 0.45266(11) -0.44101(7) 0.0320(2) Uani 1 1 d D A 1
N17_1 N 0.49525(15) 0.56564(12) -0.29608(9) 0.0284(2) Uani 1 1 d D A 1
C17_1 C 0.3765(2) 0.58066(17) -0.36805(12) 0.0367(3) Uani 1 1 d D A 1
H17A_1 H 0.2604 0.6239 -0.3494 0.055 Uiso 1 1 calc R A 1
H17B_1 H 0.3787 0.4964 -0.3768 0.055 Uiso 1 1 calc R A 1
H17C_1 H 0.4103 0.6318 -0.4264 0.055 Uiso 1 1 calc R A 1
C18_1 C 0.45706(18) 0.59969(14) -0.21435(10) 0.0304(3) Uani 1 1 d D A 1
H18_1 H 0.3435 0.6370 -0.1948 0.046 Uiso 1 1 calc R A 1
N19_1 N 0.59500(14) 0.57588(11) -0.16287(8) 0.0259(2) Uani 1 1 d D A 1
N11A_2 N 0.4998(8) 0.9030(17) 0.7379(7) 0.0238(9) Uani 0.628(2) 1 d PD B 1
C11A_2 C 0.3179(9) 0.9566(12) 0.7187(8) 0.0337(14) Uani 0.628(2) 1 d PD B 1
H11A_2 H 0.3038 1.0139 0.6569 0.051 Uiso 0.628(2) 1 calc PR B 1
H11B_2 H 0.2619 1.0045 0.7654 0.051 Uiso 0.628(2) 1 calc PR B 1
H11C_2 H 0.2658 0.8873 0.7209 0.051 Uiso 0.628(2) 1 calc PR B 1
C12A_2 C 0.6019(9) 0.856(2) 0.6679(10) 0.0226(10) Uani 0.628(2) 1 d PD B 1
O12A_2 O 0.5387(16) 0.854(2) 0.5961(9) 0.0300(11) Uani 0.628(2) 1 d PD B 1
N13A_2 N 0.7752(8) 0.812(2) 0.6805(8) 0.0229(8) Uani 0.628(2) 1 d PD B 1
C13A_2 C 0.8907(10) 0.7734(8) 0.6050(6) 0.0287(8) Uani 0.628(2) 1 d PD B 1
H13A_2 H 0.8315 0.8098 0.5459 0.043 Uiso 0.628(2) 1 calc PR B 1
H13B_2 H 0.9257 0.6800 0.6160 0.043 Uiso 0.628(2) 1 calc PR B 1
H13C_2 H 0.9922 0.8045 0.6026 0.043 Uiso 0.628(2) 1 calc PR B 1
C14A_2 C 0.8415(4) 0.8132(9) 0.7620(4) 0.0236(6) Uani 0.628(2) 1 d PD B 1
C15A_2 C 0.7365(5) 0.8582(10) 0.8317(4) 0.0233(8) Uani 0.628(2) 1 d PD B 1
C16A_2 C 0.5569(5) 0.9083(8) 0.8235(3) 0.0247(7) Uani 0.628(2) 1 d PD B 1
O16A_2 O 0.4564(3) 0.9552(5) 0.8807(3) 0.0341(5) Uani 0.628(2) 1 d PD B 1
N17A_2 N 0.8475(3) 0.8523(3) 0.89802(18) 0.0294(4) Uani 0.628(2) 1 d PD B 1
C17A_2 C 0.8025(4) 0.8868(3) 0.98805(17) 0.0403(6) Uani 0.628(2) 1 d PD B 1
H17A_2 H 0.7380 0.9771 0.9782 0.060 Uiso 0.628(2) 1 calc PR B 1
H17B_2 H 0.9074 0.8725 1.0213 0.060 Uiso 0.628(2) 1 calc PR B 1
H17C_2 H 0.7320 0.8339 1.0248 0.060 Uiso 0.628(2) 1 calc PR B 1
C18A_2 C 1.0067(3) 0.8034(2) 0.86610(16) 0.0326(5) Uani 0.628(2) 1 d PD B 1
H18A_2 H 1.1073 0.7889 0.8995 0.049 Uiso 0.628(2) 1 calc PR B 1
N19A_2 N 1.0090(4) 0.7773(4) 0.7825(2) 0.0298(5) Uani 0.628(2) 1 d PD B 1
N11B_2 N 0.7879(14) 0.801(4) 0.6746(14) 0.0229(8) Uani 0.372(2) 1 d PD B 2
C11B_2 C 0.8912(18) 0.7553(16) 0.5987(10) 0.0287(8) Uani 0.372(2) 1 d PD B 2
H11D_2 H 0.9334 0.8244 0.5589 0.043 Uiso 0.372(2) 1 calc PR B 2
H11E_2 H 0.8214 0.7271 0.5622 0.043 Uiso 0.372(2) 1 calc PR B 2
H11F_2 H 0.9887 0.6835 0.6237 0.043 Uiso 0.372(2) 1 calc PR B 2
C12B_2 C 0.6125(16) 0.845(4) 0.6621(16) 0.0226(10) Uani 0.372(2) 1 d PD B 2
O12B_2 O 0.552(3) 0.841(4) 0.5902(16) 0.0300(11) Uani 0.372(2) 1 d PD B 2
N13B_2 N 0.5119(15) 0.889(3) 0.7321(13) 0.0238(9) Uani 0.372(2) 1 d PD B 2
C13B_2 C 0.3256(15) 0.935(2) 0.7227(14) 0.0337(14) Uani 0.372(2) 1 d PD B 2
H13D_2 H 0.2951 1.0218 0.6831 0.051 Uiso 0.372(2) 1 calc PR B 2
H13E_2 H 0.2706 0.9367 0.7841 0.051 Uiso 0.372(2) 1 calc PR B 2
H13F_2 H 0.2863 0.8782 0.6945 0.051 Uiso 0.372(2) 1 calc PR B 2
C14B_2 C 0.5864(9) 0.9016(15) 0.8077(7) 0.0247(7) Uani 0.372(2) 1 d PD B 2
C15B_2 C 0.7617(9) 0.8585(19) 0.8178(7) 0.0233(8) Uani 0.372(2) 1 d PD B 2
C16B_2 C 0.8749(8) 0.8057(17) 0.7518(8) 0.0236(6) Uani 0.372(2) 1 d PD B 2
O16B_2 O 1.0322(6) 0.7619(6) 0.7549(3) 0.0298(5) Uani 0.372(2) 1 d PD B 2
N17B_2 N 0.7853(5) 0.8836(5) 0.9018(3) 0.0294(4) Uani 0.372(2) 1 d PD B 2
C17B_2 C 0.9517(6) 0.8577(5) 0.9448(4) 0.0480(13) Uani 0.372(2) 1 d PD B 2
H17D_2 H 1.0168 0.7687 0.9476 0.072 Uiso 0.372(2) 1 calc PR B 2
H17E_2 H 0.9325 0.8725 1.0078 0.072 Uiso 0.372(2) 1 calc PR B 2
H17F_2 H 1.0165 0.9147 0.9076 0.072 Uiso 0.372(2) 1 calc PR B 2
C18B_2 C 0.6305(5) 0.9391(4) 0.9334(3) 0.0341(9) Uani 0.372(2) 1 d PD B 2
H18B_2 H 0.6118 0.9671 0.9899 0.051 Uiso 0.372(2) 1 calc PR B 2
N19B_2 N 0.5055(6) 0.9511(11) 0.8779(6) 0.0341(5) Uani 0.372(2) 1 d PD B 2
C21_3 C 0.30038(16) 0.81386(12) 0.25565(9) 0.0226(2) Uani 1 1 d . . .
C22_3 C 0.44328(16) 0.78933(13) 0.31026(9) 0.0248(2) Uani 1 1 d . . .
H22_3 H 0.5538 0.7490 0.2886 0.030 Uiso 1 1 calc R . .
C23_3 C 0.42628(16) 0.82267(13) 0.39495(9) 0.0248(2) Uani 1 1 d . . .
H23_3 H 0.5243 0.8051 0.4311 0.030 Uiso 1 1 calc R . .
C24_3 C 0.26437(16) 0.88232(12) 0.42726(9) 0.0233(2) Uani 1 1 d . . .
O24_3 O 0.24082(13) 0.91696(10) 0.50999(7) 0.0302(2) Uani 1 1 d . . .
H24_3 H 0.339(3) 0.9014(18) 0.5356(14) 0.036 Uiso 1 1 d . . .
C25_3 C 0.12113(16) 0.90801(13) 0.37452(9) 0.0248(2) Uani 1 1 d . . .
H25_3 H 0.0110 0.9490 0.3962 0.030 Uiso 1 1 calc R . .
C26_3 C 0.13990(16) 0.87344(13) 0.28990(9) 0.0243(2) Uani 1 1 d . . .
H26_3 H 0.0413 0.8906 0.2543 0.029 Uiso 1 1 calc R . .
C27_3 C 0.31291(16) 0.77853(12) 0.16685(9) 0.0238(2) Uani 1 1 d . . .
H27_3 H 0.2082 0.7950 0.1367 0.029 Uiso 1 1 calc R . .
C28_3 C 0.45569(17) 0.72538(13) 0.12303(9) 0.0250(2) Uani 1 1 d . . .
H28_3 H 0.5639 0.7098 0.1493 0.030 Uiso 1 1 calc R . .
C29_3 C 0.44722(17) 0.69066(13) 0.03441(9) 0.0254(3) Uani 1 1 d . . .
O29_3 O 0.60175(13) 0.63947(11) 0.00145(7) 0.0308(2) Uani 1 1 d . . .
H29_3 H 0.590(2) 0.6190(18) -0.0506(14) 0.037 Uiso 1 1 d . . .
O30_3 O 0.31597(13) 0.70525(11) -0.00465(7) 0.0350(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N11_1 0.0214(5) 0.0304(5) 0.0230(5) -0.0094(4) 0.0028(4) -0.0072(4)
C11_1 0.0279(6) 0.0401(8) 0.0339(7) -0.0178(6) 0.0102(6) -0.0091(6)
C12_1 0.0200(5) 0.0325(6) 0.0264(6) -0.0077(5) 0.0007(5) -0.0071(5)
O12_1 0.0195(4) 0.0549(7) 0.0387(6) -0.0150(5) -0.0028(4) -0.0032(4)
N13_1 0.0201(5) 0.0331(6) 0.0212(5) -0.0086(4) -0.0025(4) -0.0061(4)
C13_1 0.0299(7) 0.0422(8) 0.0229(6) -0.0084(6) -0.0066(5) -0.0099(6)
C14_1 0.0204(5) 0.0249(6) 0.0207(5) -0.0051(5) -0.0012(4) -0.0067(4)
C15_1 0.0198(5) 0.0254(6) 0.0204(5) -0.0047(5) -0.0008(4) -0.0062(4)
C16_1 0.0237(6) 0.0274(6) 0.0213(6) -0.0049(5) 0.0011(5) -0.0103(5)
O16_1 0.0357(5) 0.0438(6) 0.0206(4) -0.0103(4) -0.0002(4) -0.0151(5)
N17_1 0.0227(5) 0.0318(6) 0.0296(6) -0.0046(5) -0.0034(4) -0.0067(4)
C17_1 0.0292(7) 0.0439(8) 0.0366(8) -0.0048(7) -0.0111(6) -0.0098(6)
C18_1 0.0251(6) 0.0332(7) 0.0312(7) -0.0085(6) 0.0023(5) -0.0052(5)
N19_1 0.0242(5) 0.0294(5) 0.0231(5) -0.0083(4) 0.0034(4) -0.0050(4)
N11A_2 0.0172(10) 0.026(4) 0.0288(13) -0.0111(7) -0.0004(10) -0.0038(13)
C11A_2 0.0179(8) 0.041(4) 0.0418(11) -0.014(2) -0.0026(8) -0.0027(13)
C12A_2 0.0197(10) 0.022(4) 0.0263(16) -0.0078(9) -0.0005(11) -0.0047(15)
O12A_2 0.0246(18) 0.038(4) 0.0298(16) -0.0140(9) -0.0044(15) -0.0055(18)
N13A_2 0.0187(10) 0.025(4) 0.0251(15) -0.0093(8) -0.0006(11) -0.0032(15)
C13A_2 0.0271(6) 0.029(3) 0.0317(13) -0.0157(10) 0.0026(8) -0.0036(11)
C14A_2 0.0193(16) 0.0264(13) 0.0245(15) -0.0031(10) -0.0011(14) -0.007(2)
C15A_2 0.0210(13) 0.0285(6) 0.0212(18) -0.0047(17) 0.0001(12) -0.0091(16)
C16A_2 0.0221(15) 0.0278(11) 0.0250(19) -0.0062(14) 0.0013(13) -0.0085(16)
O16A_2 0.0308(15) 0.0408(7) 0.0293(6) -0.0134(5) 0.0077(12) -0.0057(16)
N17A_2 0.0275(13) 0.0364(15) 0.0261(7) -0.0069(8) -0.0033(11) -0.0111(11)
C17A_2 0.0456(15) 0.0551(16) 0.0262(11) -0.0144(11) -0.0027(10) -0.0186(12)
C18A_2 0.0267(10) 0.0418(12) 0.0298(11) -0.0048(10) -0.0060(9) -0.0114(9)
N19A_2 0.0181(10) 0.0368(11) 0.0310(17) -0.0044(11) -0.0011(10) -0.0047(8)
N11B_2 0.0187(10) 0.025(4) 0.0251(15) -0.0093(8) -0.0006(11) -0.0032(15)
C11B_2 0.0271(6) 0.029(3) 0.0317(13) -0.0157(10) 0.0026(8) -0.0036(11)
C12B_2 0.0197(10) 0.022(4) 0.0263(16) -0.0078(9) -0.0005(11) -0.0047(15)
O12B_2 0.0246(18) 0.038(4) 0.0298(16) -0.0140(9) -0.0044(15) -0.0055(18)
N13B_2 0.0172(10) 0.026(4) 0.0288(13) -0.0111(7) -0.0004(10) -0.0038(13)
C13B_2 0.0179(8) 0.041(4) 0.0418(11) -0.014(2) -0.0026(8) -0.0027(13)
C14B_2 0.0221(15) 0.0278(11) 0.0250(19) -0.0062(14) 0.0013(13) -0.0085(16)
C15B_2 0.0210(13) 0.0285(6) 0.0212(18) -0.0047(17) 0.0001(12) -0.0091(16)
C16B_2 0.0193(16) 0.0264(13) 0.0245(15) -0.0031(10) -0.0011(14) -0.007(2)
O16B_2 0.0181(10) 0.0368(11) 0.0310(17) -0.0044(11) -0.0011(10) -0.0047(8)
N17B_2 0.0275(13) 0.0364(15) 0.0261(7) -0.0069(8) -0.0033(11) -0.0111(11)
C17B_2 0.052(3) 0.050(3) 0.046(3) -0.007(2) -0.030(2) -0.015(2)
C18B_2 0.048(2) 0.0309(18) 0.0240(17) -0.0050(15) -0.0046(17) -0.0120(17)
N19B_2 0.0308(15) 0.0408(7) 0.0293(6) -0.0134(5) 0.0077(12) -0.0057(16)
C21_3 0.0199(5) 0.0237(5) 0.0236(6) -0.0058(5) 0.0015(5) -0.0054(4)
C22_3 0.0179(5) 0.0291(6) 0.0267(6) -0.0084(5) 0.0009(5) -0.0043(5)
C23_3 0.0178(5) 0.0315(6) 0.0251(6) -0.0088(5) 0.0000(5) -0.0051(5)
C24_3 0.0206(5) 0.0253(6) 0.0245(6) -0.0076(5) 0.0012(5) -0.0058(4)
O24_3 0.0229(4) 0.0421(6) 0.0270(5) -0.0163(4) -0.0007(4) -0.0042(4)
C25_3 0.0182(5) 0.0283(6) 0.0270(6) -0.0088(5) 0.0010(5) -0.0033(4)
C26_3 0.0188(5) 0.0291(6) 0.0244(6) -0.0064(5) -0.0011(5) -0.0050(5)
C27_3 0.0210(5) 0.0277(6) 0.0221(6) -0.0049(5) -0.0019(5) -0.0060(5)
C28_3 0.0222(5) 0.0319(6) 0.0211(6) -0.0074(5) -0.0004(5) -0.0067(5)
C29_3 0.0239(6) 0.0296(6) 0.0225(6) -0.0057(5) 0.0003(5) -0.0072(5)
O29_3 0.0253(5) 0.0437(6) 0.0248(5) -0.0155(4) 0.0011(4) -0.0060(4)
O30_3 0.0272(5) 0.0491(6) 0.0295(5) -0.0126(5) -0.0060(4) -0.0071(5)

_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
N11_1 C12_1 1.3914(17) . ?
N11_1 C16_1 1.4129(17) . ?
N11_1 C11_1 1.4621(17) . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C12_1 O12_1 1.2183(16) . ?
C12_1 N13_1 1.3772(16) . ?
N13_1 C14_1 1.3737(16) . ?
N13_1 C13_1 1.4616(16) . ?
C13_1 H13A_1 0.9800 . ?
C13_1 H13B_1 0.9800 . ?
C13_1 H13C_1 0.9800 . ?
C14_1 N19_1 1.3459(16) . ?
C14_1 C15_1 1.3729(16) . ?
C15_1 N17_1 1.3819(16) . ?
C15_1 C16_1 1.4173(17) . ?
C16_1 O16_1 1.2268(15) . ?
N17_1 C18_1 1.3429(18) . ?
N17_1 C17_1 1.4551(18) . ?
C17_1 H17A_1 0.9800 . ?
C17_1 H17B_1 0.9800 . ?
C17_1 H17C_1 0.9800 . ?
C18_1 N19_1 1.3438(18) . ?
C18_1 H18_1 0.9500 . ?
N11A_2 C12A_2 1.381(5) . ?
N11A_2 C16A_2 1.413(5) . ?
N11A_2 C11A_2 1.457(5) . ?
C11A_2 H11A_2 0.9800 . ?
C11A_2 H11B_2 0.9800 . ?
C11A_2 H11C_2 0.9800 . ?
C12A_2 O12A_2 1.233(4) . ?
C12A_2 N13A_2 1.370(5) . ?
N13A_2 C14A_2 1.374(5) . ?
N13A_2 C13A_2 1.462(5) . ?
C13A_2 H13A_2 0.9800 . ?
C13A_2 H13B_2 0.9800 . ?
C13A_2 H13C_2 0.9800 . ?
C14A_2 N19A_2 1.349(4) . ?
C14A_2 C15A_2 1.379(4) . ?
C15A_2 N17A_2 1.375(4) . ?
C15A_2 C16A_2 1.414(4) . ?
C16A_2 O16A_2 1.229(3) . ?
N17A_2 C18A_2 1.347(3) . ?
N17A_2 C17A_2 1.467(3) . ?
C17A_2 H17A_2 0.9800 . ?
C17A_2 H17B_2 0.9800 . ?
C17A_2 H17C_2 0.9800 . ?
C18A_2 N19A_2 1.340(3) . ?
C18A_2 H18A_2 0.9500 . ?
N11B_2 C12B_2 1.386(8) . ?
N11B_2 C16B_2 1.420(7) . ?
N11B_2 C11B_2 1.451(8) . ?
C11B_2 H11D_2 0.9800 . ?
C11B_2 H11E_2 0.9800 . ?
C11B_2 H11F_2 0.9800 . ?
C12B_2 O12B_2 1.232(6) . ?
C12B_2 N13B_2 1.365(8) . ?
N13B_2 C14B_2 1.377(7) . ?
N13B_2 C13B_2 1.465(8) . ?
C13B_2 H13D_2 0.9800 . ?
C13B_2 H13E_2 0.9800 . ?
C13B_2 H13F_2 0.9800 . ?
C14B_2 N19B_2 1.331(7) . ?
C14B_2 C15B_2 1.380(7) . ?
C15B_2 N17B_2 1.384(6) . ?
C15B_2 C16B_2 1.402(7) . ?
C16B_2 O16B_2 1.235(6) . ?
N17B_2 C18B_2 1.335(5) . ?
N17B_2 C17B_2 1.475(5) . ?
C17B_2 H17D_2 0.9800 . ?
C17B_2 H17E_2 0.9800 . ?
C17B_2 H17F_2 0.9800 . ?
C18B_2 N19B_2 1.326(6) . ?
C18B_2 H18B_2 0.9500 . ?
C21_3 C26_3 1.3987(17) . ?
C21_3 C22_3 1.4040(18) . ?
C21_3 C27_3 1.4533(18) . ?
C22_3 C23_3 1.3812(18) . ?
C22_3 H22_3 0.9500 . ?
C23_3 C24_3 1.3968(17) . ?
C23_3 H23_3 0.9500 . ?
C24_3 O24_3 1.3576(15) . ?
C24_3 C25_3 1.3874(18) . ?
O24_3 H24_3 0.87(2) . ?
C25_3 C26_3 1.3857(18) . ?
C25_3 H25_3 0.9500 . ?
C26_3 H26_3 0.9500 . ?
C27_3 C28_3 1.3354(18) . ?
C27_3 H27_3 0.9500 . ?
C28_3 C29_3 1.4730(18) . ?
C28_3 H28_3 0.9500 . ?
C29_3 O30_3 1.2144(17) . ?
C29_3 O29_3 1.3276(16) . ?
O29_3 H29_3 0.88(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
C12_1 N11_1 C16_1 126.75(11) . . ?
C12_1 N11_1 C11_1 115.81(11) . . ?
C16_1 N11_1 C11_1 117.41(11) . . ?
O12_1 C12_1 N13_1 121.93(12) . . ?
O12_1 C12_1 N11_1 120.86(12) . . ?
N13_1 C12_1 N11_1 117.21(11) . . ?
C14_1 N13_1 C12_1 119.56(11) . . ?
C14_1 N13_1 C13_1 120.33(11) . . ?
C12_1 N13_1 C13_1 120.00(11) . . ?
N19_1 C14_1 C15_1 112.19(11) . . ?
N19_1 C14_1 N13_1 126.09(11) . . ?
C15_1 C14_1 N13_1 121.71(11) . . ?
C14_1 C15_1 N17_1 105.26(11) . . ?
C14_1 C15_1 C16_1 123.07(11) . . ?
N17_1 C15_1 C16_1 131.65(12) . . ?
O16_1 C16_1 N11_1 121.85(12) . . ?
O16_1 C16_1 C15_1 126.52(12) . . ?
N11_1 C16_1 C15_1 111.63(11) . . ?
C18_1 N17_1 C15_1 105.78(11) . . ?
C18_1 N17_1 C17_1 127.15(13) . . ?
C15_1 N17_1 C17_1 127.07(12) . . ?
N17_1 C18_1 N19_1 113.49(12) . . ?
N17_1 C18_1 H18_1 123.3 . . ?
N19_1 C18_1 H18_1 123.3 . . ?
C18_1 N19_1 C14_1 103.26(11) . . ?
C12A_2 N11A_2 C16A_2 126.0(4) . . ?
C12A_2 N11A_2 C11A_2 115.9(5) . . ?
C16A_2 N11A_2 C11A_2 118.0(5) . . ?
O12A_2 C12A_2 N13A_2 121.2(7) . . ?
O12A_2 C12A_2 N11A_2 120.9(7) . . ?
N13A_2 C12A_2 N11A_2 117.9(4) . . ?
C12A_2 N13A_2 C14A_2 119.8(4) . . ?
C12A_2 N13A_2 C13A_2 120.2(5) . . ?
C14A_2 N13A_2 C13A_2 119.8(5) . . ?
N19A_2 C14A_2 N13A_2 126.1(4) . . ?
N19A_2 C14A_2 C15A_2 112.7(4) . . ?
N13A_2 C14A_2 C15A_2 121.1(4) . . ?
N17A_2 C15A_2 C14A_2 104.4(3) . . ?
N17A_2 C15A_2 C16A_2 132.5(4) . . ?
C14A_2 C15A_2 C16A_2 122.8(3) . . ?
O16A_2 C16A_2 N11A_2 121.3(4) . . ?
O16A_2 C16A_2 C15A_2 126.4(4) . . ?
N11A_2 C16A_2 C15A_2 112.3(3) . . ?
C18A_2 N17A_2 C15A_2 106.7(3) . . ?
C18A_2 N17A_2 C17A_2 126.2(2) . . ?
C15A_2 N17A_2 C17A_2 127.1(3) . . ?
N19A_2 C18A_2 N17A_2 113.2(2) . . ?
N19A_2 C18A_2 H18A_2 123.4 . . ?
N17A_2 C18A_2 H18A_2 123.4 . . ?
C18A_2 N19A_2 C14A_2 103.0(3) . . ?
C12B_2 N11B_2 C16B_2 125.9(8) . . ?
C12B_2 N11B_2 C11B_2 116.4(8) . . ?
C16B_2 N11B_2 C11B_2 117.7(8) . . ?
N11B_2 C11B_2 H11D_2 109.5 . . ?
N11B_2 C11B_2 H11E_2 109.5 . . ?
H11D_2 C11B_2 H11E_2 109.5 . . ?
N11B_2 C11B_2 H11F_2 109.5 . . ?
H11D_2 C11B_2 H11F_2 109.5 . . ?
H11E_2 C11B_2 H11F_2 109.5 . . ?
O12B_2 C12B_2 N13B_2 122.2(12) . . ?
O12B_2 C12B_2 N11B_2 120.1(12) . . ?
N13B_2 C12B_2 N11B_2 117.7(6) . . ?
C12B_2 N13B_2 C14B_2 120.0(8) . . ?
C12B_2 N13B_2 C13B_2 119.9(9) . . ?
C14B_2 N13B_2 C13B_2 119.9(9) . . ?
N13B_2 C13B_2 H13D_2 109.5 . . ?
N13B_2 C13B_2 H13E_2 109.5 . . ?
H13D_2 C13B_2 H13E_2 109.5 . . ?
N13B_2 C13B_2 H13F_2 109.5 . . ?
H13D_2 C13B_2 H13F_2 109.5 . . ?
H13E_2 C13B_2 H13F_2 109.5 . . ?
N19B_2 C14B_2 N13B_2 126.6(7) . . ?
N19B_2 C14B_2 C15B_2 112.7(6) . . ?
N13B_2 C14B_2 C15B_2 120.7(7) . . ?
C14B_2 C15B_2 N17B_2 103.5(6) . . ?
C14B_2 C15B_2 C16B_2 123.3(5) . . ?
N17B_2 C15B_2 C16B_2 133.2(6) . . ?
O16B_2 C16B_2 C15B_2 128.6(7) . . ?
O16B_2 C16B_2 N11B_2 119.2(7) . . ?
C15B_2 C16B_2 N11B_2 112.1(6) . . ?
C18B_2 N17B_2 C15B_2 106.8(4) . . ?
C18B_2 N17B_2 C17B_2 127.4(4) . . ?
C15B_2 N17B_2 C17B_2 125.7(5) . . ?
N17B_2 C17B_2 H17D_2 109.5 . . ?
N17B_2 C17B_2 H17E_2 109.5 . . ?
H17D_2 C17B_2 H17E_2 109.5 . . ?
N17B_2 C17B_2 H17F_2 109.5 . . ?
H17D_2 C17B_2 H17F_2 109.5 . . ?
H17E_2 C17B_2 H17F_2 109.5 . . ?
N19B_2 C18B_2 N17B_2 113.0(4) . . ?
N19B_2 C18B_2 H18B_2 123.5 . . ?
N17B_2 C18B_2 H18B_2 123.5 . . ?
C18B_2 N19B_2 C14B_2 104.0(5) . . ?
C26_3 C21_3 C22_3 117.70(11) . . ?
C26_3 C21_3 C27_3 119.47(11) . . ?
C22_3 C21_3 C27_3 122.82(11) . . ?
C23_3 C22_3 C21_3 121.25(11) . . ?
C23_3 C22_3 H22_3 119.4 . . ?
C21_3 C22_3 H22_3 119.4 . . ?
C22_3 C23_3 C24_3 119.75(12) . . ?
C22_3 C23_3 H23_3 120.1 . . ?
C24_3 C23_3 H23_3 120.1 . . ?
O24_3 C24_3 C25_3 117.81(11) . . ?
O24_3 C24_3 C23_3 122.03(12) . . ?
C25_3 C24_3 C23_3 120.16(12) . . ?
C24_3 O24_3 H24_3 110.4(13) . . ?
C26_3 C25_3 C24_3 119.50(12) . . ?
C26_3 C25_3 H25_3 120.3 . . ?
C24_3 C25_3 H25_3 120.3 . . ?
C25_3 C26_3 C21_3 121.64(12) . . ?
C25_3 C26_3 H26_3 119.2 . . ?
C21_3 C26_3 H26_3 119.2 . . ?
C28_3 C27_3 C21_3 127.06(12) . . ?
C28_3 C27_3 H27_3 116.5 . . ?
C21_3 C27_3 H27_3 116.5 . . ?
C27_3 C28_3 C29_3 120.74(12) . . ?
C27_3 C28_3 H28_3 119.6 . . ?
C29_3 C28_3 H28_3 119.6 . . ?
O30_3 C29_3 O29_3 123.03(12) . . ?
O30_3 C29_3 C28_3 124.99(12) . . ?
O29_3 C29_3 C28_3 111.98(11) . . ?
C29_3 O29_3 H29_3 108.4(13) . . ?

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
C16_1 N11_1 C12_1 O12_1 178.78(13) . . . . ?
C11_1 N11_1 C12_1 O12_1 0.6(2) . . . . ?
C16_1 N11_1 C12_1 N13_1 -1.8(2) . . . . ?
C11_1 N11_1 C12_1 N13_1 -179.91(12) . . . . ?
O12_1 C12_1 N13_1 C14_1 -177.51(13) . . . . ?
N11_1 C12_1 N13_1 C14_1 3.05(19) . . . . ?
O12_1 C12_1 N13_1 C13_1 -1.4(2) . . . . ?
N11_1 C12_1 N13_1 C13_1 179.18(12) . . . . ?
C12_1 N13_1 C14_1 N19_1 176.90(13) . . . . ?
C13_1 N13_1 C14_1 N19_1 0.8(2) . . . . ?
C12_1 N13_1 C14_1 C15_1 -2.20(19) . . . . ?
C13_1 N13_1 C14_1 C15_1 -178.31(12) . . . . ?
N19_1 C14_1 C15_1 N17_1 -1.05(15) . . . . ?
N13_1 C14_1 C15_1 N17_1 178.17(11) . . . . ?
N19_1 C14_1 C15_1 C16_1 -179.43(12) . . . . ?
N13_1 C14_1 C15_1 C16_1 -0.2(2) . . . . ?
C12_1 N11_1 C16_1 O16_1 179.25(13) . . . . ?
C11_1 N11_1 C16_1 O16_1 -2.63(19) . . . . ?
C12_1 N11_1 C16_1 C15_1 -0.46(18) . . . . ?
C11_1 N11_1 C16_1 C15_1 177.65(12) . . . . ?
C14_1 C15_1 C16_1 O16_1 -178.23(13) . . . . ?
N17_1 C15_1 C16_1 O16_1 3.9(2) . . . . ?
C14_1 C15_1 C16_1 N11_1 1.46(18) . . . . ?
N17_1 C15_1 C16_1 N11_1 -176.45(13) . . . . ?
C14_1 C15_1 N17_1 C18_1 0.14(14) . . . . ?
C16_1 C15_1 N17_1 C18_1 178.33(14) . . . . ?
C14_1 C15_1 N17_1 C17_1 179.75(13) . . . . ?
C16_1 C15_1 N17_1 C17_1 -2.1(2) . . . . ?
C15_1 N17_1 C18_1 N19_1 0.81(16) . . . . ?
C17_1 N17_1 C18_1 N19_1 -178.80(14) . . . . ?
N17_1 C18_1 N19_1 C14_1 -1.40(16) . . . . ?
C15_1 C14_1 N19_1 C18_1 1.48(15) . . . . ?
N13_1 C14_1 N19_1 C18_1 -177.70(13) . . . . ?
C16A_2 N11A_2 C12A_2 O12A_2 179(2) . . . . ?
C11A_2 N11A_2 C12A_2 O12A_2 -4(4) . . . . ?
C16A_2 N11A_2 C12A_2 N13A_2 -2(4) . . . . ?
C11A_2 N11A_2 C12A_2 N13A_2 176(2) . . . . ?
O12A_2 C12A_2 N13A_2 C14A_2 -179(2) . . . . ?
N11A_2 C12A_2 N13A_2 C14A_2 2(4) . . . . ?
O12A_2 C12A_2 N13A_2 C13A_2 6(4) . . . . ?
N11A_2 C12A_2 N13A_2 C13A_2 -174(2) . . . . ?
C12A_2 N13A_2 C14A_2 N19A_2 -177.6(18) . . . . ?
C13A_2 N13A_2 C14A_2 N19A_2 -2(3) . . . . ?
C12A_2 N13A_2 C14A_2 C15A_2 0(3) . . . . ?
C13A_2 N13A_2 C14A_2 C15A_2 175.2(13) . . . . ?
N19A_2 C14A_2 C15A_2 N17A_2 1.5(11) . . . . ?
N13A_2 C14A_2 C15A_2 N17A_2 -176.0(14) . . . . ?
N19A_2 C14A_2 C15A_2 C16A_2 176.1(9) . . . . ?
N13A_2 C14A_2 C15A_2 C16A_2 -1.4(19) . . . . ?
C12A_2 N11A_2 C16A_2 O16A_2 178.1(19) . . . . ?
C11A_2 N11A_2 C16A_2 O16A_2 1(2) . . . . ?
C12A_2 N11A_2 C16A_2 C15A_2 0(3) . . . . ?
C11A_2 N11A_2 C16A_2 C15A_2 -177.5(13) . . . . ?
N17A_2 C15A_2 C16A_2 O16A_2 -3.7(17) . . . . ?
C14A_2 C15A_2 C16A_2 O16A_2 -176.6(10) . . . . ?
N17A_2 C15A_2 C16A_2 N11A_2 174.6(12) . . . . ?
C14A_2 C15A_2 C16A_2 N11A_2 1.7(16) . . . . ?
C14A_2 C15A_2 N17A_2 C18A_2 -1.1(9) . . . . ?
C16A_2 C15A_2 N17A_2 C18A_2 -175.0(10) . . . . ?
C14A_2 C15A_2 N17A_2 C17A_2 -178.7(6) . . . . ?
C16A_2 C15A_2 N17A_2 C17A_2 7.5(15) . . . . ?
C15A_2 N17A_2 C18A_2 N19A_2 0.5(6) . . . . ?
C17A_2 N17A_2 C18A_2 N19A_2 178.0(3) . . . . ?
N17A_2 C18A_2 N19A_2 C14A_2 0.4(6) . . . . ?
N13A_2 C14A_2 N19A_2 C18A_2 176.2(15) . . . . ?
C15A_2 C14A_2 N19A_2 C18A_2 -1.2(10) . . . . ?
C16B_2 N11B_2 C12B_2 O12B_2 177(4) . . . . ?
C11B_2 N11B_2 C12B_2 O12B_2 1(7) . . . . ?
C16B_2 N11B_2 C12B_2 N13B_2 -4(7) . . . . ?
C11B_2 N11B_2 C12B_2 N13B_2 -179(4) . . . . ?
O12B_2 C12B_2 N13B_2 C14B_2 -175(4) . . . . ?
N11B_2 C12B_2 N13B_2 C14B_2 6(6) . . . . ?
O12B_2 C12B_2 N13B_2 C13B_2 0(7) . . . . ?
N11B_2 C12B_2 N13B_2 C13B_2 -179(4) . . . . ?
C12B_2 N13B_2 C14B_2 N19B_2 175(3) . . . . ?
C13B_2 N13B_2 C14B_2 N19B_2 1(4) . . . . ?
C12B_2 N13B_2 C14B_2 C15B_2 -6(4) . . . . ?
C13B_2 N13B_2 C14B_2 C15B_2 180(2) . . . . ?
N19B_2 C14B_2 C15B_2 N17B_2 0.7(19) . . . . ?
N13B_2 C14B_2 C15B_2 N17B_2 -178(2) . . . . ?
N19B_2 C14B_2 C15B_2 C16B_2 -178.2(18) . . . . ?
N13B_2 C14B_2 C15B_2 C16B_2 3(3) . . . . ?
C14B_2 C15B_2 C16B_2 O16B_2 -178.2(18) . . . . ?
N17B_2 C15B_2 C16B_2 O16B_2 3(4) . . . . ?
C14B_2 C15B_2 C16B_2 N11B_2 0(3) . . . . ?
N17B_2 C15B_2 C16B_2 N11B_2 -179(3) . . . . ?
C12B_2 N11B_2 C16B_2 O16B_2 179(4) . . . . ?
C11B_2 N11B_2 C16B_2 O16B_2 -5(4) . . . . ?
C12B_2 N11B_2 C16B_2 C15B_2 1(5) . . . . ?
C11B_2 N11B_2 C16B_2 C15B_2 177(3) . . . . ?
C14B_2 C15B_2 N17B_2 C18B_2 -1.0(16) . . . . ?
C16B_2 C15B_2 N17B_2 C18B_2 178(2) . . . . ?
C14B_2 C15B_2 N17B_2 C17B_2 -178.8(9) . . . . ?
C16B_2 C15B_2 N17B_2 C17B_2 0(3) . . . . ?
C15B_2 N17B_2 C18B_2 N19B_2 1.0(12) . . . . ?
C17B_2 N17B_2 C18B_2 N19B_2 178.8(7) . . . . ?
N17B_2 C18B_2 N19B_2 C14B_2 -0.5(12) . . . . ?
N13B_2 C14B_2 N19B_2 C18B_2 179(2) . . . . ?
C15B_2 C14B_2 N19B_2 C18B_2 -0.1(17) . . . . ?
C26_3 C21_3 C22_3 C23_3 0.07(19) . . . . ?
C27_3 C21_3 C22_3 C23_3 -179.09(13) . . . . ?
C21_3 C22_3 C23_3 C24_3 -0.2(2) . . . . ?
C22_3 C23_3 C24_3 O24_3 179.99(12) . . . . ?
C22_3 C23_3 C24_3 C25_3 0.0(2) . . . . ?
O24_3 C24_3 C25_3 C26_3 -179.65(12) . . . . ?
C23_3 C24_3 C25_3 C26_3 0.3(2) . . . . ?
C24_3 C25_3 C26_3 C21_3 -0.5(2) . . . . ?
C22_3 C21_3 C26_3 C25_3 0.3(2) . . . . ?
C27_3 C21_3 C26_3 C25_3 179.47(12) . . . . ?
C26_3 C21_3 C27_3 C28_3 177.56(13) . . . . ?
C22_3 C21_3 C27_3 C28_3 -3.3(2) . . . . ?
C21_3 C27_3 C28_3 C29_3 177.79(12) . . . . ?
C27_3 C28_3 C29_3 O30_3 -0.8(2) . . . . ?
C27_3 C28_3 C29_3 O29_3 179.85(13) . . . . ?

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
O24_3 H24_3 O12A_2 0.87(2) 1.81(2) 2.679(9) 174(2) .
O24_3 H24_3 O12B_2 0.87(2) 1.86(3) 2.719(16) 171(2) .
O29_3 H29_3 N19_1 0.88(2) 1.84(2) 2.7129(15) 172.2(19) .

_diffrn_measured_fraction_theta_max 0.882
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055