# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010


# Attachment '- Halasz et al-NJC-cif.cif'

data_publication_text
#TrackingRef '- Halasz et al-NJC-cif.cif'

_publ_section_title              
;
Cocrystal of 4-oxopimelic acid and 4,4'-bipyridine:
polymorphism and solid-state transformation
;

_publ_contact_author             
;
'Halasz, Ivan'
Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
_publ_contact_author_email       ihalasz@chem.pmf.hr
_publ_contact_author_phone       '+385 1 4606416'

loop_
_publ_author_name
_publ_author_address

I.Halasz
;Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
M.Rubcic
;Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
K.Uzarevic
;Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
I.Dilovic
;Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
E.Mestrovic
;Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;

_publ_requested_journal          'New Journal of Chemistry'

data_Form_I
_database_code_depnum_ccdc_archive 'CCDC 785101'
#TrackingRef '- Halasz et al-NJC-cif_2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-oxo-heptane-1,7-dioic acid 4,4'-bipyridine
;
_chemical_name_common            "4-oxopimelic acid 4,4'-bipyridine"
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O5, C10 H8 N2'
_chemical_formula_sum            'C17 H18 N2 O5'
_chemical_formula_weight         330.33
_chemical_compound_source        'chemical synthesis'

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_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                   15.8717(3)
_cell_length_b                   9.4064(2)
_cell_length_c                   17.3535(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 140.5120(10)
_cell_angle_gamma                90.00
_cell_volume                     1647.53(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7207
_cell_measurement_theta_min      3.9384
_cell_measurement_theta_max      28.0647

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15784
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2893
_reflns_number_gt                2131
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;

_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.1461P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2893
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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
C11 C -0.25400(16) 0.94452(19) -0.17313(15) 0.0533(4) Uani 1 1 d . . .
C12 C -0.15595(15) 0.84848(18) -0.06600(14) 0.0504(4) Uani 1 1 d . . .
H12A H -0.0770 0.9028 0.0019 0.060 Uiso 1 1 calc R . .
H12B H -0.1308 0.7746 -0.0844 0.060 Uiso 1 1 calc R . .
C13 C -0.20643(15) 0.77947(19) -0.02896(14) 0.0533(4) Uani 1 1 d . . .
H13A H -0.2399 0.8530 -0.0186 0.064 Uiso 1 1 calc R . .
H13B H -0.2801 0.7179 -0.0941 0.064 Uiso 1 1 calc R . .
C14 C -0.10545(15) 0.69429(17) 0.08496(13) 0.0452(4) Uani 1 1 d . . .
C15 C -0.15273(15) 0.5982(2) 0.11511(14) 0.0547(4) Uani 1 1 d . . .
H15A H -0.1922 0.5140 0.0646 0.066 Uiso 1 1 calc R . .
H15B H -0.2211 0.6468 0.0959 0.066 Uiso 1 1 calc R . .
C16 C -0.04409(16) 0.55309(17) 0.24634(14) 0.0506(4) Uani 1 1 d . . .
H16A H -0.0775 0.4785 0.2562 0.061 Uiso 1 1 calc R . .
H16B H 0.0288 0.5139 0.2682 0.061 Uiso 1 1 calc R . .
C17 C 0.00640(15) 0.67241(17) 0.33050(14) 0.0457(4) Uani 1 1 d . . .
O11 O -0.36608(12) 0.96103(18) -0.23095(13) 0.0860(5) Uani 1 1 d . . .
O12 O -0.20482(12) 1.00920(15) -0.19890(12) 0.0732(4) Uani 1 1 d . . .
H12 H -0.2632 1.0557 -0.2612 0.110 Uiso 1 1 calc R . .
O13 O 0.01103(11) 0.70314(15) 0.15202(11) 0.0690(4) Uani 1 1 d . . .
O14 O 0.12489(11) 0.64618(13) 0.44232(10) 0.0648(4) Uani 1 1 d . . .
H14 H 0.1485 0.7131 0.4860 0.097 Uiso 1 1 calc R . .
O15 O -0.05478(12) 0.78015(13) 0.30045(11) 0.0664(4) Uani 1 1 d . . .
C21 C 0.36342(18) 0.8798(2) 0.67788(17) 0.0696(5) Uani 1 1 d . . .
H21 H 0.4004 0.8385 0.6603 0.084 Uiso 1 1 calc R . .
C22 C 0.43920(16) 0.9730(2) 0.77299(15) 0.0617(5) Uani 1 1 d . . .
H22 H 0.5252 0.9935 0.8179 0.074 Uiso 1 1 calc R . .
C23 C 0.38809(14) 1.03686(16) 0.80258(13) 0.0444(4) Uani 1 1 d . . .
C24 C 0.25844(15) 1.00273(19) 0.72972(15) 0.0554(4) Uani 1 1 d . . .
H24 H 0.2183 1.0434 0.7443 0.066 Uiso 1 1 calc R . .
C25 C 0.18940(17) 0.9081(2) 0.63550(16) 0.0657(5) Uani 1 1 d . . .
H25 H 0.1024 0.8870 0.5876 0.079 Uiso 1 1 calc R . .
C26 C 0.46939(14) 1.13655(16) 0.90624(13) 0.0442(4) Uani 1 1 d . . .
C27 C 0.60406(15) 1.15062(18) 0.98893(15) 0.0548(4) Uani 1 1 d . . .
H27 H 0.6453 1.0967 0.9801 0.066 Uiso 1 1 calc R . .
C28 C 0.67704(16) 1.2439(2) 1.08404(16) 0.0620(5) Uani 1 1 d . . .
H28 H 0.7674 1.2510 1.1382 0.074 Uiso 1 1 calc R . .
C29 C 0.49659(18) 1.3114(2) 1.02391(18) 0.0711(6) Uani 1 1 d . . .
H29 H 0.4584 1.3663 1.0356 0.085 Uiso 1 1 calc R . .
C30 C 0.41617(17) 1.2212(2) 0.92577(17) 0.0631(5) Uani 1 1 d . . .
H30 H 0.3259 1.2173 0.8726 0.076 Uiso 1 1 calc R . .
N21 N 0.23967(15) 0.84526(16) 0.60920(13) 0.0628(4) Uani 1 1 d . . .
N22 N 0.62569(14) 1.32418(16) 1.10273(13) 0.0626(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C11 0.0515(9) 0.0607(11) 0.0510(10) 0.0041(8) 0.0404(9) 0.0051(7)
C12 0.0485(9) 0.0543(10) 0.0487(9) 0.0034(7) 0.0376(8) 0.0046(7)
C13 0.0464(8) 0.0627(11) 0.0482(9) 0.0010(8) 0.0359(8) -0.0011(7)
C14 0.0461(8) 0.0501(9) 0.0437(8) -0.0055(7) 0.0358(8) -0.0025(7)
C15 0.0539(9) 0.0633(11) 0.0490(9) -0.0093(8) 0.0402(8) -0.0137(8)
C16 0.0605(9) 0.0467(9) 0.0528(9) -0.0041(7) 0.0459(9) -0.0052(7)
C17 0.0522(8) 0.0463(9) 0.0484(9) -0.0011(7) 0.0414(8) -0.0037(7)
O11 0.0550(7) 0.1258(13) 0.0782(9) 0.0396(9) 0.0517(8) 0.0265(7)
O12 0.0632(7) 0.0880(10) 0.0761(9) 0.0356(7) 0.0557(8) 0.0223(7)
O13 0.0482(7) 0.0952(10) 0.0604(8) 0.0189(7) 0.0410(6) 0.0049(6)
O14 0.0622(7) 0.0614(8) 0.0482(7) -0.0070(6) 0.0367(7) -0.0007(6)
O15 0.0735(8) 0.0520(7) 0.0691(8) -0.0016(6) 0.0538(7) 0.0068(6)
C21 0.0608(11) 0.0860(14) 0.0548(11) -0.0140(10) 0.0428(10) 0.0008(10)
C22 0.0451(9) 0.0800(12) 0.0522(10) -0.0141(9) 0.0355(9) -0.0021(8)
C23 0.0414(8) 0.0489(9) 0.0400(8) 0.0022(7) 0.0307(7) 0.0006(6)
C24 0.0489(9) 0.0691(11) 0.0532(10) -0.0078(9) 0.0407(8) -0.0087(8)
C25 0.0529(10) 0.0821(13) 0.0554(10) -0.0143(10) 0.0401(9) -0.0220(9)
C26 0.0424(8) 0.0479(9) 0.0416(8) 0.0014(7) 0.0322(7) 0.0001(6)
C27 0.0444(8) 0.0606(10) 0.0547(10) -0.0087(8) 0.0370(8) -0.0026(7)
C28 0.0449(8) 0.0691(12) 0.0555(10) -0.0128(9) 0.0344(9) -0.0082(8)
C29 0.0617(11) 0.0786(13) 0.0750(13) -0.0248(11) 0.0532(11) -0.0073(9)
C30 0.0465(9) 0.0757(12) 0.0622(11) -0.0164(9) 0.0406(9) -0.0050(8)
N21 0.0643(9) 0.0664(10) 0.0490(8) -0.0092(7) 0.0414(8) -0.0101(7)
N22 0.0589(9) 0.0636(9) 0.0571(9) -0.0138(7) 0.0426(8) -0.0088(7)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O11 1.2003(19) . ?
C11 O12 1.311(2) . ?
C11 C12 1.493(2) . ?
C12 C13 1.507(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.493(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O13 1.2075(17) . ?
C14 C15 1.504(2) . ?
C15 C16 1.509(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.493(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O15 1.2084(19) . ?
C17 O14 1.3154(19) . ?
O12 H12 0.8200 . ?
O14 H14 0.8200 . ?
C21 N21 1.331(2) . ?
C21 C22 1.369(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(2) . ?
C23 C26 1.482(2) . ?
C24 C25 1.379(2) . ?
C24 H24 0.9300 . ?
C25 N21 1.325(2) . ?
C25 H25 0.9300 . ?
C26 C30 1.380(2) . ?
C26 C27 1.382(2) . ?
C27 C28 1.373(2) . ?
C27 H27 0.9300 . ?
C28 N22 1.322(2) . ?
C28 H28 0.9300 . ?
C29 N22 1.326(2) . ?
C29 C30 1.376(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
O11 C11 O12 122.92(16) . . ?
O11 C11 C12 124.57(16) . . ?
O12 C11 C12 112.51(13) . . ?
C11 C12 C13 113.91(13) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 114.52(13) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
O13 C14 C13 121.32(14) . . ?
O13 C14 C15 120.67(14) . . ?
C13 C14 C15 118.01(13) . . ?
C14 C15 C16 113.47(13) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 112.99(14) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O15 C17 O14 123.49(15) . . ?
O15 C17 C16 124.23(15) . . ?
O14 C17 C16 112.27(14) . . ?
C11 O12 H12 109.5 . . ?
C17 O14 H14 109.5 . . ?
N21 C21 C22 123.53(17) . . ?
N21 C21 H21 118.2 . . ?
C22 C21 H21 118.2 . . ?
C21 C22 C23 120.18(16) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 116.26(15) . . ?
C24 C23 C26 122.88(14) . . ?
C22 C23 C26 120.86(13) . . ?
C25 C24 C23 119.54(16) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
N21 C25 C24 123.89(16) . . ?
N21 C25 H25 118.1 . . ?
C24 C25 H25 118.1 . . ?
C30 C26 C27 116.03(15) . . ?
C30 C26 C23 122.58(13) . . ?
C27 C26 C23 121.38(14) . . ?
C28 C27 C26 120.21(15) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
N22 C28 C27 123.51(15) . . ?
N22 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
N22 C29 C30 123.48(17) . . ?
N22 C29 H29 118.3 . . ?
C30 C29 H29 118.3 . . ?
C29 C30 C26 120.05(16) . . ?
C29 C30 H30 120.0 . . ?
C26 C30 H30 120.0 . . ?
C25 N21 C21 116.58(15) . . ?
C28 N22 C29 116.72(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.060

data_Form_II
_database_code_depnum_ccdc_archive 'CCDC 785102'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            "4-oxo-heptane-1,7-dioic acid 4,4'-bipyridine"
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O5, C10 H8 N2'
_chemical_formula_sum            'C17 H18 N2 O5'
_chemical_formula_weight         330.33
_chemical_compound_source        'chemical synthesis'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-c 2yc'
_symmetry_int_tables_number      15

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

_cell_length_a                   7.583(3)
_cell_length_b                   8.752(2)
_cell_length_c                   24.527(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.29(3)
_cell_angle_gamma                90.00
_cell_volume                     1626.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       '\w scans'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2479
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1579
_reflns_number_gt                1055
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;

_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1129P)^2^+0.0000P] 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         1579
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.089
_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
H11 H 0.255(4) 0.587(3) 0.1327(12) 0.119(11) Uiso 1 1 d D . .
C11 C 0.2785(2) 0.3762(2) 0.15193(8) 0.0522(5) Uani 1 1 d . . .
C12 C 0.2161(3) 0.2655(2) 0.19330(8) 0.0576(5) Uani 1 1 d . . .
H12A H 0.1268 0.1999 0.1762 0.069 Uiso 1 1 calc R . .
H12B H 0.1615 0.3216 0.2222 0.069 Uiso 1 1 calc R . .
C13 C 0.3626(3) 0.1670(2) 0.21798(8) 0.0556(5) Uani 1 1 d . . .
H13A H 0.3116 0.0916 0.2417 0.067 Uiso 1 1 calc R . .
H13B H 0.4188 0.1126 0.1889 0.067 Uiso 1 1 calc R . .
C14 C 0.5000 0.2558(3) 0.2500 0.0584(7) Uani 1 2 d S . .
O11 O 0.2104(2) 0.51263(17) 0.15603(6) 0.0670(5) Uani 1 1 d D . .
O12 O 0.3787(2) 0.34238(19) 0.11670(7) 0.0786(6) Uani 1 1 d . . .
O13 O 0.5000 0.3931(3) 0.2500 0.1050(10) Uani 1 2 d S . .
C21 C 0.3072(3) 0.8665(2) 0.09703(9) 0.0635(6) Uani 1 1 d . . .
H21 H 0.2402 0.8947 0.1263 0.076 Uiso 1 1 calc R . .
C22 C 0.3696(3) 0.9789(2) 0.06394(8) 0.0596(6) Uani 1 1 d . . .
H22 H 0.3469 1.0809 0.0716 0.071 Uiso 1 1 calc R . .
C23 C 0.4669(2) 0.9412(2) 0.01884(7) 0.0480(5) Uani 1 1 d . . .
C24 C 0.4973(3) 0.7862(2) 0.01060(8) 0.0580(6) Uani 1 1 d . . .
H24 H 0.5607 0.7536 -0.0189 0.070 Uiso 1 1 calc R . .
C25 C 0.4325(3) 0.6824(2) 0.04659(9) 0.0621(6) Uani 1 1 d . . .
H25 H 0.4559 0.5795 0.0409 0.075 Uiso 1 1 calc R . .
N21 N 0.3380(2) 0.71975(19) 0.08919(7) 0.0594(5) 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
C11 0.0550(10) 0.0557(12) 0.0458(10) -0.0043(8) -0.0007(8) 0.0058(9)
C12 0.0558(11) 0.0597(12) 0.0574(11) 0.0007(9) 0.0047(9) -0.0001(9)
C13 0.0685(12) 0.0443(10) 0.0538(10) -0.0003(8) 0.0008(9) -0.0020(8)
C14 0.0720(18) 0.0469(16) 0.0558(15) 0.000 -0.0035(13) 0.000
O11 0.0794(10) 0.0596(10) 0.0632(9) 0.0076(7) 0.0171(8) 0.0193(7)
O12 0.1003(12) 0.0715(11) 0.0661(10) 0.0022(7) 0.0306(9) 0.0184(8)
O13 0.126(2) 0.0482(14) 0.135(2) 0.000 -0.0647(19) 0.000
C21 0.0762(13) 0.0607(14) 0.0541(12) -0.0048(9) 0.0090(10) -0.0006(10)
C22 0.0753(12) 0.0474(11) 0.0563(11) -0.0086(9) 0.0061(10) 0.0012(9)
C23 0.0479(10) 0.0487(11) 0.0468(9) -0.0051(8) -0.0067(7) 0.0026(8)
C24 0.0620(11) 0.0543(12) 0.0582(12) -0.0024(9) 0.0081(9) 0.0119(9)
C25 0.0709(13) 0.0495(12) 0.0659(12) 0.0043(9) 0.0024(11) 0.0108(9)
N21 0.0678(11) 0.0555(11) 0.0545(10) 0.0018(8) -0.0017(8) 0.0047(8)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O12 1.211(2) . ?
C11 O11 1.307(2) . ?
C11 C12 1.492(3) . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.497(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O13 1.202(3) . ?
C14 C13 1.497(2) 2_655 ?
O11 H11 0.94(2) . ?
C21 N21 1.321(3) . ?
C21 C22 1.371(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(3) . ?
C23 C23 1.483(4) 5_675 ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 N21 1.331(3) . ?
C25 H25 0.9300 . ?

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
O12 C11 O11 122.73(19) . . ?
O12 C11 C12 123.44(18) . . ?
O11 C11 C12 113.80(16) . . ?
C11 C12 C13 113.21(16) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.46(17) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
O13 C14 C13 121.28(12) . . ?
O13 C14 C13 121.29(12) . 2_655 ?
C13 C14 C13 117.4(2) . 2_655 ?
C11 O11 H11 115(2) . . ?
N21 C21 C22 122.95(19) . . ?
N21 C21 H21 118.5 . . ?
C22 C21 H21 118.5 . . ?
C21 C22 C23 120.35(19) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 116.30(18) . . ?
C24 C23 C23 121.5(2) . 5_675 ?
C22 C23 C23 122.2(2) . 5_675 ?
C25 C24 C23 119.07(18) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
N21 C25 C24 124.04(19) . . ?
N21 C25 H25 118.0 . . ?
C24 C25 H25 118.0 . . ?
C21 N21 C25 117.26(18) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048