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

_publ_contact_author_name        'Prof. Shyamaprosad Goswami'
_publ_contact_author_address     
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
_publ_contact_author_email       SPGOSWAMICAL@YAHOO.COM
_publ_contact_author_fax         '6 04 6579150'
_publ_contact_author_phone       '6 04 6577888 Ext. 3690'
_publ_contact_letter             
;
Date : 7 May 2007

Manager
Cambridge Crystallographic Data Centre
12 Union Road
Cambridge CB2 1EZ
England

Ref: Deposition of Crystal Structure Data -
Paper to be submitted to Journal of Organic Chemistry.

Dear Sir,

I herewith attach the crystal structure data in the
CIF format for the structure appearing in a manuscript entitled
Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide Based
Receptors and Its Supramolecular Behavior in the Solid State

This manuscript shall be submitted to the journal "Journal of
Organic Chemistry".

I request you to kindly acknowledge this deposition and send me
the CCDC reference number for this structure so as to
enable me to inform to the editor of the "Journal of
Organic Chemistry"

Yours Sincerely,

Fun Hoong-Kun
;
#============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Recognition of Dicarboxylic Acids by 3,3/-Bipyridine
Amide Based Receptors and Its Supramolecular Behavior in Solid State
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address

'Shyamaprosad Goswami' ?
; Department of Chemistry
Bengal Engineering and Science University
Shibpur, Howrah-711103,
India
;
'Subrata Jana' ?
; Department of Chemistry
Bengal Engineering and Science University
Shibpur, Howrah-711103,
India
;
'Hoong-Kun Fun.' ?
; X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;

#============================================================================
_publ_section_exptl_refinement   
;
All the H atoms were located in a difference Fourier map
and were refined with isotropic displacement factors.
;
#============================================================================

data_spg376am
_database_code_depnum_ccdc_archive 'CCDC 646488'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide
Based Receptors and Its Supramolecular Behavior in the Solid State
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29

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                   5.7920(4)
_cell_length_b                   9.9488(7)
_cell_length_c                   12.1657(8)
_cell_angle_alpha                98.753(2)
_cell_angle_beta                 103.129(1)
_cell_angle_gamma                91.122(1)
_cell_volume                     673.69(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1287
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      30.09

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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  
;
Brucker SMART APEX2 CCD diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8512
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         30.09
_reflns_number_total             3928
_reflns_number_gt                2025
_reflns_threshold_expression     'I > 2\s(I)'

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL and PLATON (Spek, 2003)
;

_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^)+(0.0872P)^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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3928
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
N1 N 0.4474(3) 0.88921(14) 0.13736(14) 0.0574(4) Uani 1 1 d . . .
N2 N 0.5263(3) 0.67634(14) 0.18144(13) 0.0541(4) Uani 1 1 d . . .
C1 C 0.3018(3) 0.97833(18) 0.08904(17) 0.0580(5) Uani 1 1 d . . .
C2 C 0.0753(3) 0.94707(16) 0.02319(14) 0.0477(4) Uani 1 1 d . . .
C3 C 0.0008(4) 0.81034(19) 0.00673(18) 0.0617(5) Uani 1 1 d . . .
C4 C 0.1442(4) 0.71590(19) 0.05389(17) 0.0617(5) Uani 1 1 d . . .
C5 C 0.3691(3) 0.75954(16) 0.12119(14) 0.0485(4) Uani 1 1 d . . .
C6 C 0.4989(3) 0.53798(17) 0.17717(16) 0.0510(4) Uani 1 1 d . . .
C7 C 0.6736(3) 0.48102(18) 0.27104(19) 0.0592(5) Uani 1 1 d . . .
C8 C 0.6027(6) 0.3305(3) 0.2616(4) 0.1073(12) Uani 1 1 d . . .
C9 C 0.6580(6) 0.5574(3) 0.3885(2) 0.0844(8) Uani 1 1 d . . .
C10 C 0.9262(4) 0.4964(3) 0.2562(3) 0.0792(7) Uani 1 1 d . . .
O1 O 0.3465(3) 0.46750(13) 0.10614(13) 0.0714(5) Uani 1 1 d . . .
O2 O 0.8518(3) 1.02538(14) 0.25766(14) 0.0769(5) Uani 1 1 d . . .
C11 C 0.9936(3) 0.95726(18) 0.32578(16) 0.0531(5) Uani 1 1 d . . .
C12 C 1.2136(4) 1.0386(2) 0.3951(2) 0.0610(5) Uani 1 1 d . . .
C13 C 1.3937(3) 0.9567(2) 0.4628(2) 0.0605(5) Uani 1 1 d . . .
O3 O 0.9489(3) 0.84059(14) 0.33226(15) 0.0839(5) Uani 1 1 d . . .
H1 H 0.365(4) 1.071(2) 0.1055(17) 0.068(6) Uiso 1 1 d . . .
H3 H -0.162(4) 0.778(2) -0.0362(19) 0.083(7) Uiso 1 1 d . . .
H4 H 0.079(4) 0.622(2) 0.0467(18) 0.077(6) Uiso 1 1 d . . .
H8A H 0.611(7) 0.282(4) 0.181(3) 0.147(15) Uiso 1 1 d . . .
H8B H 0.432(7) 0.316(3) 0.269(3) 0.148(13) Uiso 1 1 d . . .
H8C H 0.709(7) 0.304(3) 0.331(3) 0.140(12) Uiso 1 1 d . . .
H9A H 0.491(7) 0.567(3) 0.395(3) 0.143(13) Uiso 1 1 d . . .
H9B H 0.724(5) 0.655(3) 0.401(2) 0.101(8) Uiso 1 1 d . . .
H9C H 0.761(5) 0.515(2) 0.447(2) 0.097(8) Uiso 1 1 d . . .
H10A H 0.930(6) 0.452(4) 0.174(3) 0.148(13) Uiso 1 1 d . . .
H10B H 1.017(5) 0.438(3) 0.306(2) 0.103(9) Uiso 1 1 d . . .
H10C H 0.973(5) 0.595(3) 0.265(2) 0.105(9) Uiso 1 1 d . . .
H12A H 1.273(5) 1.093(3) 0.345(2) 0.098(8) Uiso 1 1 d . . .
H12B H 1.160(4) 1.114(2) 0.445(2) 0.089(7) Uiso 1 1 d . . .
H13A H 1.323(4) 0.904(2) 0.5118(19) 0.079(7) Uiso 1 1 d . . .
H13B H 1.444(4) 0.882(2) 0.414(2) 0.085(7) Uiso 1 1 d . . .
H1N2 H 0.666(4) 0.728(2) 0.2327(19) 0.075(6) Uiso 1 1 d . . .
H1O2 H 0.698(5) 0.964(3) 0.212(2) 0.111(9) Uiso 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
N1 0.0416(8) 0.0434(7) 0.0732(10) 0.0130(7) -0.0174(7) -0.0049(6)
N2 0.0435(8) 0.0417(7) 0.0646(9) 0.0108(7) -0.0141(7) -0.0023(7)
C1 0.0424(9) 0.0433(9) 0.0752(12) 0.0132(8) -0.0149(9) -0.0038(8)
C2 0.0404(9) 0.0456(8) 0.0483(9) 0.0093(7) -0.0089(8) -0.0025(7)
C3 0.0460(10) 0.0496(10) 0.0726(12) 0.0113(9) -0.0208(9) -0.0075(8)
C4 0.0525(11) 0.0443(9) 0.0719(12) 0.0135(8) -0.0208(9) -0.0082(8)
C5 0.0422(9) 0.0445(8) 0.0502(9) 0.0093(7) -0.0080(8) 0.0002(7)
C6 0.0388(9) 0.0448(9) 0.0650(11) 0.0084(8) 0.0031(8) 0.0005(7)
C7 0.0444(10) 0.0472(9) 0.0818(13) 0.0200(9) -0.0008(10) 0.0066(8)
C8 0.081(2) 0.0559(13) 0.168(3) 0.0458(18) -0.024(2) -0.0015(13)
C9 0.0844(19) 0.099(2) 0.0726(15) 0.0375(14) 0.0076(14) 0.0185(16)
C10 0.0486(12) 0.0750(15) 0.110(2) 0.0173(15) 0.0085(13) 0.0146(12)
O1 0.0586(8) 0.0468(7) 0.0905(10) 0.0048(7) -0.0152(8) -0.0072(6)
O2 0.0525(8) 0.0551(8) 0.1020(11) 0.0179(7) -0.0283(8) -0.0033(7)
C11 0.0394(9) 0.0469(9) 0.0617(11) 0.0040(8) -0.0081(8) 0.0011(8)
C12 0.0453(10) 0.0496(10) 0.0739(13) 0.0064(10) -0.0127(10) -0.0034(9)
C13 0.0401(10) 0.0527(10) 0.0744(13) 0.0058(10) -0.0127(10) -0.0005(9)
O3 0.0675(10) 0.0546(8) 0.1046(12) 0.0222(7) -0.0359(8) -0.0129(7)

_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
N1 C5 1.330(2) . ?
N1 C1 1.344(2) . ?
N2 C6 1.374(2) . ?
N2 C5 1.401(2) . ?
N2 H1N2 0.98(2) . ?
C1 C2 1.375(2) . ?
C1 H1 0.96(2) . ?
C2 C3 1.390(3) . ?
C2 C2 1.477(3) 2_575 ?
C3 C4 1.371(3) . ?
C3 H3 0.99(2) . ?
C4 C5 1.393(2) . ?
C4 H4 0.98(2) . ?
C6 O1 1.209(2) . ?
C6 C7 1.531(3) . ?
C7 C10 1.521(3) . ?
C7 C8 1.525(3) . ?
C7 C9 1.536(3) . ?
C8 H8A 1.03(4) . ?
C8 H8B 1.02(4) . ?
C8 H8C 1.00(4) . ?
C9 H9A 0.99(4) . ?
C9 H9B 1.02(3) . ?
C9 H9C 0.97(3) . ?
C10 H10A 1.04(4) . ?
C10 H10B 0.97(3) . ?
C10 H10C 1.00(3) . ?
O2 C11 1.306(2) . ?
O2 H1O2 1.06(3) . ?
C11 O3 1.202(2) . ?
C11 C12 1.501(2) . ?
C12 C13 1.509(3) . ?
C12 H12A 0.99(3) . ?
C12 H12B 0.99(2) . ?
C13 C13 1.514(4) 2_876 ?
C13 H13A 1.00(2) . ?
C13 H13B 0.97(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
C5 N1 C1 118.28(15) . . ?
C6 N2 C5 127.17(14) . . ?
C6 N2 H1N2 120.4(12) . . ?
C5 N2 H1N2 112.4(13) . . ?
N1 C1 C2 125.42(16) . . ?
N1 C1 H1 114.9(13) . . ?
C2 C1 H1 119.6(13) . . ?
C1 C2 C3 114.70(16) . . ?
C1 C2 C2 121.64(19) . 2_575 ?
C3 C2 C2 123.64(19) . 2_575 ?
C4 C3 C2 121.76(17) . . ?
C4 C3 H3 117.2(13) . . ?
C2 C3 H3 121.0(13) . . ?
C3 C4 C5 118.65(17) . . ?
C3 C4 H4 119.1(13) . . ?
C5 C4 H4 121.9(13) . . ?
N1 C5 C4 121.17(16) . . ?
N1 C5 N2 114.14(15) . . ?
C4 C5 N2 124.62(15) . . ?
O1 C6 N2 122.63(17) . . ?
O1 C6 C7 122.83(16) . . ?
N2 C6 C7 114.53(15) . . ?
C10 C7 C8 109.7(2) . . ?
C10 C7 C6 110.64(19) . . ?
C8 C7 C6 107.72(19) . . ?
C10 C7 C9 109.7(2) . . ?
C8 C7 C9 109.7(3) . . ?
C6 C7 C9 109.38(17) . . ?
C7 C8 H8A 108(2) . . ?
C7 C8 H8B 112(2) . . ?
H8A C8 H8B 107(3) . . ?
C7 C8 H8C 103.2(19) . . ?
H8A C8 H8C 120(3) . . ?
H8B C8 H8C 107(3) . . ?
C7 C9 H9A 112(2) . . ?
C7 C9 H9B 111.4(15) . . ?
H9A C9 H9B 103(2) . . ?
C7 C9 H9C 108.0(14) . . ?
H9A C9 H9C 117(2) . . ?
H9B C9 H9C 105(2) . . ?
C7 C10 H10A 109(2) . . ?
C7 C10 H10B 104.7(16) . . ?
H10A C10 H10B 105(2) . . ?
C7 C10 H10C 109.1(16) . . ?
H10A C10 H10C 108(2) . . ?
H10B C10 H10C 121(2) . . ?
C11 O2 H1O2 110.7(14) . . ?
O3 C11 O2 122.47(16) . . ?
O3 C11 C12 123.79(17) . . ?
O2 C11 C12 113.73(16) . . ?
C11 C12 C13 114.31(16) . . ?
C11 C12 H12A 107.9(15) . . ?
C13 C12 H12A 116.1(16) . . ?
C11 C12 H12B 106.7(15) . . ?
C13 C12 H12B 111.9(14) . . ?
H12A C12 H12B 98(2) . . ?
C12 C13 C13 112.9(2) . 2_876 ?
C12 C13 H13A 112.3(13) . . ?
C13 C13 H13A 108.7(13) 2_876 . ?
C12 C13 H13B 112.3(14) . . ?
C13 C13 H13B 110.5(15) 2_876 . ?
H13A C13 H13B 99.3(18) . . ?

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
C5 N1 C1 C2 0.0(3) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C2 177.8(2) . . . 2_575 ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C2 C3 C4 -178.2(2) 2_575 . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C1 N1 C5 C4 1.4(3) . . . . ?
C1 N1 C5 N2 -175.64(17) . . . . ?
C3 C4 C5 N1 -1.8(3) . . . . ?
C3 C4 C5 N2 174.90(18) . . . . ?
C6 N2 C5 N1 -176.59(17) . . . . ?
C6 N2 C5 C4 6.5(3) . . . . ?
C5 N2 C6 O1 11.2(3) . . . . ?
C5 N2 C6 C7 -167.60(17) . . . . ?
O1 C6 C7 C10 115.2(2) . . . . ?
N2 C6 C7 C10 -66.0(2) . . . . ?
O1 C6 C7 C8 -4.7(3) . . . . ?
N2 C6 C7 C8 174.1(2) . . . . ?
O1 C6 C7 C9 -123.9(2) . . . . ?
N2 C6 C7 C9 55.0(2) . . . . ?
O3 C11 C12 C13 8.1(3) . . . . ?
O2 C11 C12 C13 -172.54(19) . . . . ?
C11 C12 C13 C13 -176.5(3) . . . 2_876 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.09
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039

# Attachment 'complex_B_ccdc_cif.txt'

data_spg376b
_database_code_depnum_ccdc_archive 'CCDC 603755'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 N4 O6'
_chemical_formula_weight         548.63

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   6.4295(3)
_cell_length_b                   9.8850(4)
_cell_length_c                   21.8431(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.739(3)
_cell_angle_gamma                90.00
_cell_volume                     1385.3(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    3225
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      30.81

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100.0(1)
_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  
;
Brucker SMART APEX2 CCD diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17515
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         30.81
_reflns_number_total             4325
_reflns_number_gt                2950
_reflns_threshold_expression     'I > 2\s(I)'

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL and PLATON (Spek, 2003)
;

_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^)+(0.0636P)^2^+0.0469P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4325
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46055(18) 0.20324(9) 0.15766(5) 0.0318(3) Uani 1 1 d . . .
O2 O 0.45613(16) 0.79729(10) 0.09654(5) 0.0271(3) Uani 1 1 d . . .
O3 O 0.19477(16) 0.69011(10) 0.13800(5) 0.0314(3) Uani 1 1 d . . .
N1 N 0.62397(18) 0.56130(11) 0.07535(5) 0.0211(3) Uani 1 1 d . . .
N2 N 0.41336(19) 0.42253(12) 0.12859(5) 0.0216(3) Uani 1 1 d . . .
C1 C 0.7854(2) 0.58396(14) 0.04071(6) 0.0220(3) Uani 1 1 d . . .
C2 C 0.9079(2) 0.48304(13) 0.01735(5) 0.0180(3) Uani 1 1 d . . .
C3 C 0.8441(2) 0.35073(14) 0.02858(6) 0.0216(3) Uani 1 1 d . . .
C4 C 0.6758(2) 0.32449(13) 0.06320(6) 0.0223(3) Uani 1 1 d . . .
C5 C 0.5730(2) 0.43341(13) 0.08817(6) 0.0188(3) Uani 1 1 d . . .
C6 C 0.3788(2) 0.31256(13) 0.16561(6) 0.0204(3) Uani 1 1 d . . .
C7 C 0.2349(2) 0.33920(13) 0.21772(6) 0.0205(3) Uani 1 1 d . . .
C8 C 0.0142(2) 0.36940(17) 0.19121(7) 0.0296(3) Uani 1 1 d . . .
C9 C 0.3212(3) 0.45886(16) 0.25683(7) 0.0277(3) Uani 1 1 d . . .
C10 C 0.2326(3) 0.21223(15) 0.25819(7) 0.0294(4) Uani 1 1 d . . .
C11 C 0.2741(2) 0.79397(13) 0.12076(6) 0.0211(3) Uani 1 1 d . . .
C12 C 0.1715(2) 0.93138(14) 0.12324(6) 0.0228(3) Uani 1 1 d . . .
C13 C 0.0810(2) 0.97060(13) 0.06001(6) 0.0202(3) Uani 1 1 d . . .
C14 C -0.1300(2) 0.95379(13) 0.04353(6) 0.0216(3) Uani 1 1 d . . .
C15 C -0.2106(2) 0.98145(13) -0.01567(6) 0.0218(3) Uani 1 1 d . . .
H1 H 0.812(3) 0.6781(17) 0.0327(7) 0.026(4) Uiso 1 1 d . . .
H3 H 0.914(2) 0.2748(16) 0.0139(7) 0.021(4) Uiso 1 1 d . . .
H4 H 0.629(3) 0.2358(18) 0.0697(7) 0.028(4) Uiso 1 1 d . . .
H8A H -0.079(3) 0.3865(18) 0.2261(7) 0.037(5) Uiso 1 1 d . . .
H8B H 0.013(3) 0.4512(18) 0.1641(7) 0.033(4) Uiso 1 1 d . . .
H8C H -0.040(3) 0.2867(19) 0.1661(8) 0.040(5) Uiso 1 1 d . . .
H9A H 0.243(3) 0.4670(17) 0.2939(8) 0.033(4) Uiso 1 1 d . . .
H9B H 0.476(3) 0.4439(19) 0.2676(8) 0.043(5) Uiso 1 1 d . . .
H9C H 0.303(3) 0.5446(19) 0.2333(7) 0.036(5) Uiso 1 1 d . . .
H10A H 0.181(3) 0.133(2) 0.2330(8) 0.044(5) Uiso 1 1 d . . .
H10B H 0.137(3) 0.2281(17) 0.2917(7) 0.030(4) Uiso 1 1 d . . .
H10C H 0.379(3) 0.190(2) 0.2767(8) 0.046(5) Uiso 1 1 d . . .
H12A H 0.058(2) 0.9265(15) 0.1513(7) 0.023(4) Uiso 1 1 d . . .
H12B H 0.276(3) 0.9914(17) 0.1389(7) 0.027(4) Uiso 1 1 d . . .
H14A H -0.227(3) 0.9195(17) 0.0729(7) 0.032(4) Uiso 1 1 d . . .
H15A H -0.355(3) 0.9679(16) -0.0257(6) 0.023(4) Uiso 1 1 d . . .
H1N2 H 0.349(3) 0.4970(18) 0.1356(7) 0.028(4) Uiso 1 1 d . . .
H1O2 H 0.518(3) 0.700(2) 0.0933(9) 0.065(7) Uiso 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
O1 0.0418(7) 0.0171(5) 0.0387(6) 0.0036(4) 0.0203(5) 0.0037(4)
O2 0.0234(6) 0.0174(5) 0.0418(6) 0.0016(4) 0.0119(5) 0.0011(4)
O3 0.0300(6) 0.0226(5) 0.0434(6) 0.0073(4) 0.0157(5) 0.0027(4)
N1 0.0203(6) 0.0172(5) 0.0265(6) 0.0030(4) 0.0067(5) 0.0021(4)
N2 0.0225(6) 0.0174(6) 0.0259(6) 0.0026(4) 0.0091(5) 0.0037(5)
C1 0.0219(7) 0.0170(6) 0.0277(7) 0.0041(5) 0.0071(6) 0.0011(5)
C2 0.0189(7) 0.0175(6) 0.0177(6) 0.0010(4) 0.0021(5) 0.0002(5)
C3 0.0239(7) 0.0176(6) 0.0240(6) -0.0023(5) 0.0074(6) -0.0002(5)
C4 0.0258(8) 0.0158(6) 0.0260(6) -0.0012(5) 0.0074(6) -0.0025(5)
C5 0.0179(7) 0.0184(6) 0.0203(6) 0.0016(5) 0.0030(5) -0.0003(5)
C6 0.0207(7) 0.0181(6) 0.0229(6) 0.0007(5) 0.0046(5) -0.0011(5)
C7 0.0217(7) 0.0181(6) 0.0224(6) 0.0000(5) 0.0060(5) -0.0016(5)
C8 0.0230(8) 0.0368(9) 0.0294(7) 0.0006(6) 0.0042(6) -0.0005(7)
C9 0.0333(9) 0.0258(8) 0.0246(7) -0.0030(6) 0.0064(6) -0.0072(6)
C10 0.0384(10) 0.0227(7) 0.0286(7) 0.0041(6) 0.0135(7) 0.0004(6)
C11 0.0220(7) 0.0216(7) 0.0198(6) 0.0000(5) 0.0026(5) 0.0013(5)
C12 0.0236(8) 0.0201(7) 0.0252(7) -0.0012(5) 0.0047(6) 0.0026(6)
C13 0.0234(8) 0.0122(6) 0.0255(6) -0.0010(5) 0.0057(5) 0.0027(5)
C14 0.0222(7) 0.0152(6) 0.0284(7) 0.0010(5) 0.0093(6) 0.0019(5)
C15 0.0174(7) 0.0166(6) 0.0320(7) -0.0013(5) 0.0066(6) 0.0008(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
O1 C6 1.2189(15) . ?
O2 C11 1.3156(15) . ?
O3 C11 1.2171(16) . ?
N1 C5 1.3402(16) . ?
N1 C1 1.3428(16) . ?
N2 C6 1.3814(16) . ?
N2 C5 1.4011(15) . ?
C1 C2 1.3884(18) . ?
C2 C3 1.3972(19) . ?
C2 C2 1.486(2) 3_765 ?
C3 C4 1.3845(17) . ?
C4 C5 1.3931(18) . ?
C6 C7 1.5356(16) . ?
C7 C8 1.527(2) . ?
C7 C10 1.5358(19) . ?
C7 C9 1.541(2) . ?
C11 C12 1.5127(19) . ?
C12 C13 1.514(2) . ?
C13 C14 1.390(2) . ?
C13 C15 1.4008(17) 3_575 ?
C14 C15 1.388(2) . ?
C15 C13 1.4008(17) 3_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 118.93(11) . . ?
C6 N2 C5 125.57(11) . . ?
N1 C1 C2 124.40(12) . . ?
C1 C2 C3 115.36(11) . . ?
C1 C2 C2 121.03(14) . 3_765 ?
C3 C2 C2 123.62(14) . 3_765 ?
C4 C3 C2 121.33(12) . . ?
C3 C4 C5 118.48(12) . . ?
N1 C5 C4 121.23(11) . . ?
N1 C5 N2 113.79(11) . . ?
C4 C5 N2 124.98(11) . . ?
O1 C6 N2 121.80(11) . . ?
O1 C6 C7 122.95(11) . . ?
N2 C6 C7 115.24(11) . . ?
C8 C7 C10 109.54(12) . . ?
C8 C7 C6 110.03(11) . . ?
C10 C7 C6 108.39(11) . . ?
C8 C7 C9 110.63(12) . . ?
C10 C7 C9 108.96(12) . . ?
C6 C7 C9 109.26(11) . . ?
O3 C11 O2 123.18(12) . . ?
O3 C11 C12 123.61(12) . . ?
O2 C11 C12 113.19(11) . . ?
C11 C12 C13 109.88(11) . . ?
C14 C13 C15 118.40(13) . 3_575 ?
C14 C13 C12 121.07(11) . . ?
C15 C13 C12 120.45(13) 3_575 . ?
C15 C14 C13 121.06(12) . . ?
C14 C15 C13 120.52(14) . 3_575 ?

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
C5 N1 C1 C2 -0.9(2) . . . . ?
N1 C1 C2 C3 4.3(2) . . . . ?
N1 C1 C2 C2 -176.12(15) . . . 3_765 ?
C1 C2 C3 C4 -2.9(2) . . . . ?
C2 C2 C3 C4 177.51(15) 3_765 . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
C1 N1 C5 C4 -4.0(2) . . . . ?
C1 N1 C5 N2 175.12(12) . . . . ?
C3 C4 C5 N1 5.2(2) . . . . ?
C3 C4 C5 N2 -173.85(13) . . . . ?
C6 N2 C5 N1 -156.17(13) . . . . ?
C6 N2 C5 C4 22.9(2) . . . . ?
C5 N2 C6 O1 -14.7(2) . . . . ?
C5 N2 C6 C7 164.06(13) . . . . ?
O1 C6 C7 C8 -114.88(16) . . . . ?
N2 C6 C7 C8 66.33(16) . . . . ?
O1 C6 C7 C10 4.9(2) . . . . ?
N2 C6 C7 C10 -173.91(13) . . . . ?
O1 C6 C7 C9 123.48(16) . . . . ?
N2 C6 C7 C9 -55.31(16) . . . . ?
O3 C11 C12 C13 -102.24(16) . . . . ?
O2 C11 C12 C13 76.07(15) . . . . ?
C11 C12 C13 C14 99.19(14) . . . . ?
C11 C12 C13 C15 -77.61(16) . . . 3_575 ?
C15 C13 C14 C15 1.1(2) 3_575 . . . ?
C12 C13 C14 C15 -175.76(12) . . . . ?
C13 C14 C15 C13 -1.1(2) . . . 3_575 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.81
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.056

# Attachment 'receptor_1_ccdc_cif.txt'

data_spg376dm
_database_code_depnum_ccdc_archive 'CCDC 646489'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
Recognition of Dicarboxylic Acids by 3,3/-Bipyridine Amide
Based Receptors and Its Supramolecular Behavior in the Solid State
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N4 O2'
_chemical_formula_weight         354.45

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P21/c '

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

_cell_length_a                   5.8375(1)
_cell_length_b                   15.9570(2)
_cell_length_c                   10.32990(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.814(1)
_cell_angle_gamma                90.00
_cell_volume                     957.27(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.37

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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  
;
Brucker SMART APEX2 CCD diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24213
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         31.37
_reflns_number_total             3151
_reflns_number_gt                1922
_reflns_threshold_expression     'I > 2\s(I)'

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL and PLATON (Spek, 2003)
;

_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^)+(0.0750P)^2^+0.1031P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1526(2) 0.26497(8) 0.29355(10) 0.0635(4) Uani 1 1 d . . .
N1 N -0.0766(2) 0.39566(9) 0.59934(12) 0.0600(4) Uani 1 1 d . . .
N2 N 0.1055(2) 0.28819(8) 0.50478(11) 0.0488(3) Uani 1 1 d . . .
C1 C -0.2433(3) 0.45288(11) 0.59867(14) 0.0566(4) Uani 1 1 d . . .
C2 C -0.4058(2) 0.46916(8) 0.49555(12) 0.0439(3) Uani 1 1 d . . .
C3 C -0.3781(4) 0.42433(12) 0.38409(16) 0.0752(6) Uani 1 1 d . . .
C4 C -0.2041(3) 0.36678(12) 0.37985(16) 0.0703(6) Uani 1 1 d . . .
C5 C -0.0607(2) 0.35247(8) 0.49193(12) 0.0437(3) Uani 1 1 d . . .
C6 C 0.1919(2) 0.24425(9) 0.40736(13) 0.0454(3) Uani 1 1 d . . .
C7 C 0.3324(2) 0.16640(10) 0.44907(14) 0.0504(4) Uani 1 1 d . . .
C8 C 0.1641(4) 0.09960(15) 0.4870(4) 0.0953(9) Uani 1 1 d . . .
C9 C 0.4568(5) 0.13630(17) 0.33406(19) 0.0844(7) Uani 1 1 d . . .
C10 C 0.5122(3) 0.18375(15) 0.56349(18) 0.0658(5) Uani 1 1 d . . .
H1N2 H 0.154(3) 0.2778(11) 0.5886(17) 0.062(5) Uiso 1 1 d . . .
H1 H -0.245(3) 0.4838(12) 0.677(2) 0.072(5) Uiso 1 1 d . . .
H9C H 0.550(4) 0.0863(15) 0.361(2) 0.097(7) Uiso 1 1 d . . .
H10C H 0.611(4) 0.1356(13) 0.5841(19) 0.082(6) Uiso 1 1 d . . .
H10B H 0.448(4) 0.2012(13) 0.642(2) 0.087(6) Uiso 1 1 d . . .
H4 H -0.191(4) 0.3348(15) 0.306(2) 0.101(7) Uiso 1 1 d . . .
H3 H -0.492(4) 0.4276(14) 0.316(2) 0.098(7) Uiso 1 1 d . . .
H8B H 0.249(4) 0.0507(17) 0.504(2) 0.109(8) Uiso 1 1 d . . .
H9B H 0.344(5) 0.1213(17) 0.256(3) 0.118(9) Uiso 1 1 d . . .
H10A H 0.598(4) 0.2291(17) 0.541(2) 0.110(9) Uiso 1 1 d . . .
H8A H 0.079(6) 0.1195(19) 0.556(3) 0.133(11) Uiso 1 1 d . . .
H9A H 0.557(7) 0.188(2) 0.307(3) 0.181(15) Uiso 1 1 d . . .
H8C H 0.058(5) 0.0902(17) 0.413(3) 0.123(10) Uiso 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
O1 0.0763(8) 0.0756(8) 0.0380(5) 0.0014(5) 0.0027(5) 0.0195(6)
N1 0.0566(8) 0.0830(10) 0.0386(6) -0.0084(6) -0.0034(5) 0.0171(7)
N2 0.0512(7) 0.0582(7) 0.0358(6) 0.0010(5) -0.0018(5) 0.0087(5)
C1 0.0570(9) 0.0742(10) 0.0377(7) -0.0101(7) -0.0003(6) 0.0118(8)
C2 0.0497(8) 0.0423(7) 0.0388(7) 0.0012(5) 0.0008(6) -0.0006(5)
C3 0.0944(14) 0.0787(12) 0.0460(9) -0.0158(8) -0.0246(9) 0.0393(10)
C4 0.0905(13) 0.0734(11) 0.0420(8) -0.0168(8) -0.0176(8) 0.0327(9)
C5 0.0467(7) 0.0464(7) 0.0373(6) 0.0020(5) 0.0010(5) -0.0001(6)
C6 0.0440(7) 0.0528(8) 0.0383(7) -0.0005(5) -0.0009(5) 0.0004(6)
C7 0.0457(8) 0.0573(8) 0.0469(8) -0.0007(6) -0.0019(6) 0.0065(6)
C8 0.0665(14) 0.0570(12) 0.161(3) 0.0169(14) 0.0030(16) -0.0010(10)
C9 0.0979(16) 0.1002(16) 0.0534(10) -0.0075(10) -0.0009(10) 0.0508(14)
C10 0.0544(10) 0.0899(14) 0.0503(9) 0.0033(9) -0.0084(7) 0.0119(10)

_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 1.2204(17) . ?
N1 C5 1.3174(18) . ?
N1 C1 1.334(2) . ?
N2 C6 1.3642(18) . ?
N2 C5 1.4090(18) . ?
C1 C2 1.377(2) . ?
C2 C3 1.379(2) . ?
C2 C2 1.486(3) 3_466 ?
C3 C4 1.373(2) . ?
C4 C5 1.377(2) . ?
C6 C7 1.527(2) . ?
C7 C10 1.524(2) . ?
C7 C8 1.528(3) . ?
C7 C9 1.531(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
C5 N1 C1 117.86(12) . . ?
C6 N2 C5 127.38(12) . . ?
N1 C1 C2 125.30(13) . . ?
C1 C2 C3 114.71(14) . . ?
C1 C2 C2 122.22(15) . 3_466 ?
C3 C2 C2 123.06(15) . 3_466 ?
C4 C3 C2 121.56(15) . . ?
C3 C4 C5 118.20(14) . . ?
N1 C5 C4 122.18(14) . . ?
N1 C5 N2 114.08(12) . . ?
C4 C5 N2 123.64(13) . . ?
O1 C6 N2 121.60(13) . . ?
O1 C6 C7 122.37(13) . . ?
N2 C6 C7 115.99(12) . . ?
C10 C7 C6 112.29(14) . . ?
C10 C7 C8 109.76(19) . . ?
C6 C7 C8 107.39(14) . . ?
C10 C7 C9 108.36(16) . . ?
C6 C7 C9 108.66(13) . . ?
C8 C7 C9 110.4(2) . . ?

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
C5 N1 C1 C2 2.0(3) . . . . ?
N1 C1 C2 C3 -3.9(3) . . . . ?
N1 C1 C2 C2 176.65(17) . . . 3_466 ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C2 C3 C4 -178.9(2) 3_466 . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C1 N1 C5 C4 2.3(3) . . . . ?
C1 N1 C5 N2 -174.35(14) . . . . ?
C3 C4 C5 N1 -4.3(3) . . . . ?
C3 C4 C5 N2 172.01(17) . . . . ?
C6 N2 C5 N1 -166.43(14) . . . . ?
C6 N2 C5 C4 17.0(3) . . . . ?
C5 N2 C6 O1 10.1(2) . . . . ?
C5 N2 C6 C7 -167.85(13) . . . . ?
O1 C6 C7 C10 133.90(17) . . . . ?
N2 C6 C7 C10 -48.18(18) . . . . ?
O1 C6 C7 C8 -105.3(2) . . . . ?
N2 C6 C7 C8 72.6(2) . . . . ?
O1 C6 C7 C9 14.1(2) . . . . ?
N2 C6 C7 C9 -168.03(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        31.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037

