# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0946m_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF 312 (4-pyridyl)-CONH-(CH2)4-NHCO-(4-pyridyl), HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 H18 N4 O2) (C6 H10 O4)
;
_chemical_formula_sum            'C22 H28 N4 O6'
_chemical_formula_weight         444.48

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                   5.1160(4)
_cell_length_b                   5.1957(4)
_cell_length_c                   19.5042(16)
_cell_angle_alpha                90.704(2)
_cell_angle_beta                 93.362(2)
_cell_angle_gamma                91.346(2)
_cell_volume                     517.36(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      33.32

_exptl_crystal_description       prism
_exptl_crystal_colour            gold
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.105
_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8119
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         32.56
_reflns_number_total             3505
_reflns_number_gt                3032
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3505
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
N11 N 0.15714(14) 0.56104(14) 0.20347(4) 0.01699(15) Uani 1 1 d . . .
C12 C 0.37287(16) 0.59364(16) 0.24495(4) 0.01710(16) Uani 1 1 d . . .
H12 H 0.4878 0.7354 0.2373 0.021 Uiso 1 1 calc R . .
C13 C 0.43610(16) 0.43004(16) 0.29847(4) 0.01606(16) Uani 1 1 d . . .
H13 H 0.5920 0.4582 0.3267 0.019 Uiso 1 1 calc R . .
C14 C 0.26774(15) 0.22390(15) 0.31014(4) 0.01399(15) Uani 1 1 d . . .
C15 C 0.04353(16) 0.18941(16) 0.26721(4) 0.01629(16) Uani 1 1 d . . .
H15 H -0.0759 0.0505 0.2740 0.020 Uiso 1 1 calc R . .
C16 C -0.00349(16) 0.36138(16) 0.21413(4) 0.01684(16) Uani 1 1 d . . .
H16 H -0.1557 0.3358 0.1843 0.020 Uiso 1 1 calc R . .
C17 C 0.34386(15) 0.04462(15) 0.36688(4) 0.01438(15) Uani 1 1 d . . .
N17 N 0.15103(13) -0.08074(14) 0.39655(4) 0.01597(14) Uani 1 1 d . . .
H17 H -0.011(3) -0.045(2) 0.3865(6) 0.019 Uiso 1 1 d . . .
O17 O 0.57692(11) 0.01607(13) 0.38475(3) 0.01951(14) Uani 1 1 d . . .
C21 C 0.21085(15) -0.26013(16) 0.45179(4) 0.01633(16) Uani 1 1 d . . .
H21A H 0.2842 -0.1634 0.4928 0.020 Uiso 1 1 calc R . .
H21B H 0.3449 -0.3807 0.4374 0.020 Uiso 1 1 calc R . .
C22 C -0.03100(15) -0.41131(15) 0.47006(4) 0.01592(16) Uani 1 1 d . . .
H22A H -0.0996 -0.5148 0.4297 0.019 Uiso 1 1 calc R . .
H22B H -0.1682 -0.2907 0.4824 0.019 Uiso 1 1 calc R . .
C31 C 0.31058(16) 1.06246(15) 0.09990(4) 0.01568(16) Uani 1 1 d . . .
O31 O 0.10990(12) 0.89625(13) 0.09943(3) 0.02069(15) Uani 1 1 d . . .
H31 H 0.120(3) 0.790(3) 0.1360(7) 0.025 Uiso 1 1 d . . .
O32 O 0.49187(13) 1.06224(13) 0.14255(3) 0.02205(15) Uani 1 1 d . . .
C32 C 0.27985(16) 1.24970(16) 0.04224(4) 0.01761(16) Uani 1 1 d . . .
H32A H 0.1325 1.3632 0.0512 0.021 Uiso 1 1 calc R . .
H32B H 0.2324 1.1522 -0.0008 0.021 Uiso 1 1 calc R . .
C33 C 0.52038(15) 1.41641(16) 0.03153(4) 0.01687(16) Uani 1 1 d . . .
H33A H 0.6724 1.3052 0.0259 0.020 Uiso 1 1 calc R . .
H33B H 0.5596 1.5278 0.0726 0.020 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3342(10) . ?
N11 C12 1.3359(10) . ?
C12 C13 1.3828(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.3879(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.3867(11) . ?
C14 C17 1.4954(10) . ?
C15 C16 1.3898(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2353(10) . ?
C17 N17 1.3335(10) . ?
N17 C21 1.4569(10) . ?
N17 H17 0.864(13) . ?
C21 C22 1.5125(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C22 1.5203(15) 2_546 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 O32 1.2091(10) . ?
C31 O31 1.3255(10) . ?
C31 C32 1.4998(11) . ?
O31 H31 0.908(14) . ?
C32 C33 1.5141(11) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.5216(15) 2_685 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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 118.44(7) . . ?
N11 C12 C13 122.84(7) . . ?
N11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 118.81(7) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 118.54(7) . . ?
C15 C14 C17 123.46(7) . . ?
C13 C14 C17 117.95(7) . . ?
C14 C15 C16 118.89(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N11 C16 C15 122.47(7) . . ?
N11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
O17 C17 N17 122.28(7) . . ?
O17 C17 C14 120.45(7) . . ?
N17 C17 C14 117.27(7) . . ?
C17 N17 C21 120.26(7) . . ?
C17 N17 H17 120.7(8) . . ?
C21 N17 H17 118.7(8) . . ?
N17 C21 C22 111.35(6) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C22 110.89(8) . 2_546 ?
C21 C22 H22A 109.5 . . ?
C22 C22 H22A 109.5 2_546 . ?
C21 C22 H22B 109.5 . . ?
C22 C22 H22B 109.5 2_546 . ?
H22A C22 H22B 108.0 . . ?
O32 C31 O31 123.33(7) . . ?
O32 C31 C32 125.18(7) . . ?
O31 C31 C32 111.48(7) . . ?
C31 O31 H31 112.2(8) . . ?
C31 C32 C33 114.81(7) . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C33 C32 H32B 108.6 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C33 111.20(8) . 2_685 ?
C32 C33 H33A 109.4 . . ?
C33 C33 H33A 109.4 2_685 . ?
C32 C33 H33B 109.4 . . ?
C33 C33 H33B 109.4 2_685 . ?
H33A C33 H33B 108.0 . . ?

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 C13 -0.21(13) . . . . ?
N11 C12 C13 C14 -0.51(13) . . . . ?
C12 C13 C14 C15 0.47(12) . . . . ?
C12 C13 C14 C17 178.14(7) . . . . ?
C13 C14 C15 C16 0.25(12) . . . . ?
C17 C14 C15 C16 -177.28(7) . . . . ?
C12 N11 C16 C15 0.99(13) . . . . ?
C14 C15 C16 N11 -1.01(13) . . . . ?
C15 C14 C17 O17 150.47(9) . . . . ?
C13 C14 C17 O17 -27.07(12) . . . . ?
C15 C14 C17 N17 -29.42(12) . . . . ?
C13 C14 C17 N17 153.04(8) . . . . ?
O17 C17 N17 C21 -0.40(13) . . . . ?
C14 C17 N17 C21 179.49(7) . . . . ?
C17 N17 C21 C22 -170.91(7) . . . . ?
N17 C21 C22 C22 -177.34(8) . . . 2_546 ?
O32 C31 C32 C33 11.08(13) . . . . ?
O31 C31 C32 C33 -169.96(7) . . . . ?
C31 C32 C33 C33 175.14(9) . . . 2_685 ?

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
O31 H31 N11 0.908(14) 1.788(14) 2.6940(9) 175.0(13) .
N17 H17 O17 0.864(13) 2.139(13) 2.9876(9) 167.1(12) 1_455

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 983623'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf1002m_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF313 (4-pyridyl)-CONH-(CH2)4-NHCO-(4-pyridyl) HOOC-(CH2)6-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 H18 N4 O2) (C8 H14 O4)
;
_chemical_formula_sum            'C24 H32 N4 O6'
_chemical_formula_weight         472.54

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.1221(4)
_cell_length_b                   5.2045(4)
_cell_length_c                   21.5019(14)
_cell_angle_alpha                94.963(2)
_cell_angle_beta                 95.404(2)
_cell_angle_gamma                91.630(2)
_cell_volume                     568.12(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5225
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      32.91

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.100
_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10539
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         32.58
_reflns_number_total             3669
_reflns_number_gt                3070
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3669
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
N11 N 0.61654(17) 0.47599(17) 0.22842(4) 0.01942(18) Uani 1 1 d . . .
C12 C 0.45740(19) 0.2793(2) 0.23837(4) 0.0192(2) Uani 1 1 d . . .
H12 H 0.3007 0.2448 0.2112 0.023 Uiso 1 1 calc R . .
C13 C 0.51186(19) 0.1227(2) 0.28689(4) 0.01850(19) Uani 1 1 d . . .
H13 H 0.3934 -0.0145 0.2931 0.022 Uiso 1 1 calc R . .
C14 C 0.74225(18) 0.17043(18) 0.32606(4) 0.01609(18) Uani 1 1 d . . .
C15 C 0.90911(19) 0.37330(19) 0.31536(4) 0.01826(19) Uani 1 1 d . . .
H15 H 1.0690 0.4101 0.3412 0.022 Uiso 1 1 calc R . .
C16 C 0.83832(19) 0.5212(2) 0.26637(4) 0.0192(2) Uani 1 1 d . . .
H16 H 0.9523 0.6608 0.2594 0.023 Uiso 1 1 calc R . .
C17 C 0.82656(18) 0.00674(19) 0.37808(4) 0.01610(18) Uani 1 1 d . . .
N17 N 0.63730(16) -0.11040(17) 0.40520(4) 0.01802(18) Uani 1 1 d . . .
H17 H 0.473(3) -0.071(3) 0.3960(6) 0.022 Uiso 1 1 d . . .
O17 O 1.06208(13) -0.01560(15) 0.39433(3) 0.02149(17) Uani 1 1 d . . .
C21 C 0.70446(18) -0.27374(19) 0.45580(4) 0.01778(19) Uani 1 1 d . . .
H21A H 0.7840 -0.1652 0.4932 0.021 Uiso 1 1 calc R . .
H21B H 0.8359 -0.3980 0.4427 0.021 Uiso 1 1 calc R . .
C22 C 0.46549(18) -0.41990(19) 0.47259(4) 0.01768(19) Uani 1 1 d . . .
H22A H 0.3908 -0.5349 0.4357 0.021 Uiso 1 1 calc R . .
H22B H 0.3306 -0.2961 0.4838 0.021 Uiso 1 1 calc R . .
C31 C 0.75285(19) 0.94703(19) 0.13312(4) 0.01839(19) Uani 1 1 d . . .
O31 O 0.55537(15) 0.77614(16) 0.13247(3) 0.02364(18) Uani 1 1 d . . .
H31 H 0.576(3) 0.674(3) 0.1663(7) 0.028 Uiso 1 1 d . . .
O32 O 0.93878(15) 0.96577(16) 0.17255(3) 0.02466(18) Uani 1 1 d . . .
C32 C 0.7120(2) 1.1143(2) 0.07969(5) 0.0212(2) Uani 1 1 d . . .
H32A H 0.5684 1.2317 0.0883 0.025 Uiso 1 1 calc R . .
H32B H 0.6523 1.0019 0.0412 0.025 Uiso 1 1 calc R . .
C33 C 0.94777(19) 1.2760(2) 0.06661(5) 0.0198(2) Uani 1 1 d . . .
H33A H 1.0968 1.1629 0.0601 0.024 Uiso 1 1 calc R . .
H33B H 1.0003 1.4015 0.1032 0.024 Uiso 1 1 calc R . .
C34 C 0.88477(19) 1.4201(2) 0.00862(5) 0.0204(2) Uani 1 1 d . . .
H34A H 0.8250 1.2934 -0.0273 0.025 Uiso 1 1 calc R . .
H34B H 0.7382 1.5353 0.0160 0.025 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3349(14) . ?
N11 C16 1.3373(13) . ?
C12 C13 1.3912(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3869(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3878(14) . ?
C14 C17 1.5026(12) . ?
C15 C16 1.3848(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2355(11) . ?
C17 N17 1.3364(13) . ?
N17 C21 1.4597(12) . ?
N17 H17 0.880(14) . ?
C21 C22 1.5116(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C22 1.5225(17) 2_646 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 O32 1.2098(12) . ?
C31 O31 1.3261(13) . ?
C31 C32 1.5033(13) . ?
O31 H31 0.938(15) . ?
C32 C33 1.5142(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5236(13) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C34 1.517(2) 2_785 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

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 N11 C16 118.29(8) . . ?
N11 C12 C13 122.63(9) . . ?
N11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 118.80(9) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 118.60(8) . . ?
C13 C14 C17 123.32(9) . . ?
C15 C14 C17 118.03(8) . . ?
C16 C15 C14 118.80(9) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N11 C16 C15 122.87(9) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O17 C17 N17 122.50(9) . . ?
O17 C17 C14 120.32(9) . . ?
N17 C17 C14 117.18(8) . . ?
C17 N17 C21 120.24(8) . . ?
C17 N17 H17 119.1(9) . . ?
C21 N17 H17 120.1(9) . . ?
N17 C21 C22 111.48(8) . . ?
N17 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N17 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C22 111.22(9) . 2_646 ?
C21 C22 H22A 109.4 . . ?
C22 C22 H22A 109.4 2_646 . ?
C21 C22 H22B 109.4 . . ?
C22 C22 H22B 109.4 2_646 . ?
H22A C22 H22B 108.0 . . ?
O32 C31 O31 123.59(9) . . ?
O32 C31 C32 125.10(9) . . ?
O31 C31 C32 111.29(8) . . ?
C31 O31 H31 112.0(9) . . ?
C31 C32 C33 116.29(8) . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32B 108.2 . . ?
C33 C32 H32B 108.2 . . ?
H32A C32 H32B 107.4 . . ?
C32 C33 C34 110.73(8) . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C34 C34 C33 113.68(10) 2_785 . ?
C34 C34 H34A 108.8 2_785 . ?
C33 C34 H34A 108.8 . . ?
C34 C34 H34B 108.8 2_785 . ?
C33 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?

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 C13 0.81(14) . . . . ?
N11 C12 C13 C14 -0.86(14) . . . . ?
C12 C13 C14 C15 0.18(13) . . . . ?
C12 C13 C14 C17 -177.22(8) . . . . ?
C13 C14 C15 C16 0.48(13) . . . . ?
C17 C14 C15 C16 178.02(8) . . . . ?
C12 N11 C16 C15 -0.10(14) . . . . ?
C14 C15 C16 N11 -0.55(14) . . . . ?
C13 C14 C17 O17 150.48(10) . . . . ?
C15 C14 C17 O17 -26.92(13) . . . . ?
C13 C14 C17 N17 -29.58(13) . . . . ?
C15 C14 C17 N17 153.01(9) . . . . ?
O17 C17 N17 C21 -0.43(15) . . . . ?
C14 C17 N17 C21 179.64(8) . . . . ?
C17 N17 C21 C22 -170.94(8) . . . . ?
N17 C21 C22 C22 -177.33(9) . . . 2_646 ?
O32 C31 C32 C33 14.04(15) . . . . ?
O31 C31 C32 C33 -166.98(9) . . . . ?
C31 C32 C33 C34 175.84(8) . . . . ?
C32 C33 C34 C34 -178.14(10) . . . 2_785 ?

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
O31 H31 N11 0.938(15) 1.756(16) 2.6942(11) 178.7(14) .
N17 H17 O17 0.880(14) 2.130(14) 2.9920(11) 166.1(12) 1_455

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 983624'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0831m_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF11 (4-pyridyl-CONH-(CH2)8-NHCO-(4-pyridyl), succinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C4 H6 O4)
;
_chemical_formula_sum            'C24 H32 N4 O6'
_chemical_formula_weight         472.54

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.1072(4)
_cell_length_b                   5.1171(4)
_cell_length_c                   22.119(2)
_cell_angle_alpha                96.134(6)
_cell_angle_beta                 94.037(6)
_cell_angle_gamma                91.340(6)
_cell_volume                     573.05(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1093
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.099
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5484
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         31.64
_reflns_number_total             5484
_reflns_number_gt                4617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5484
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N11 N 0.7730(2) 0.2762(2) 0.15149(5) 0.0201(2) Uani 1 1 d . . .
C12 C 0.5733(3) 0.1176(3) 0.16214(6) 0.0193(2) Uani 1 1 d . . .
H12 H 0.5373 -0.0395 0.1356 0.023 Uiso 1 1 calc R . .
C13 C 0.4158(3) 0.1730(2) 0.21056(6) 0.0184(2) Uani 1 1 d . . .
H13 H 0.2773 0.0548 0.2173 0.022 Uiso 1 1 calc R . .
C14 C 0.4656(2) 0.4050(2) 0.24887(6) 0.0157(2) Uani 1 1 d . . .
C15 C 0.6712(2) 0.5712(3) 0.23738(6) 0.0180(2) Uani 1 1 d . . .
H15 H 0.7092 0.7317 0.2626 0.022 Uiso 1 1 calc R . .
C16 C 0.8196(3) 0.4996(3) 0.18868(6) 0.0189(2) Uani 1 1 d . . .
H16 H 0.9606 0.6135 0.1813 0.023 Uiso 1 1 calc R . .
C17 C 0.2996(2) 0.4909(2) 0.30033(6) 0.0161(2) Uani 1 1 d . . .
N17 N 0.1774(2) 0.3023(2) 0.32655(5) 0.0175(2) Uani 1 1 d . . .
H17 H 0.215(3) 0.143(3) 0.3196(7) 0.021 Uiso 1 1 d . . .
O17 O 0.27721(19) 0.72772(18) 0.31718(4) 0.0218(2) Uani 1 1 d . . .
C21 C 0.0086(3) 0.3716(2) 0.37596(6) 0.0177(2) Uani 1 1 d . . .
H21A H -0.1265 0.4924 0.3623 0.021 Uiso 1 1 calc R . .
H21B H 0.1152 0.4650 0.4112 0.021 Uiso 1 1 calc R . .
C22 C -0.1255(3) 0.1303(2) 0.39587(6) 0.0178(2) Uani 1 1 d . . .
H22A H 0.0092 0.0059 0.4079 0.021 Uiso 1 1 calc R . .
H22B H -0.2383 0.0410 0.3612 0.021 Uiso 1 1 calc R . .
C23 C -0.2925(2) 0.2030(2) 0.44925(6) 0.0177(2) Uani 1 1 d . . .
H23A H -0.4333 0.3190 0.4362 0.021 Uiso 1 1 calc R . .
H23B H -0.1814 0.3031 0.4828 0.021 Uiso 1 1 calc R . .
C24 C -0.4166(3) -0.0359(2) 0.47310(6) 0.0175(2) Uani 1 1 d . . .
H24A H -0.2757 -0.1522 0.4859 0.021 Uiso 1 1 calc R . .
H24B H -0.5282 -0.1354 0.4396 0.021 Uiso 1 1 calc R . .
C31 C 1.2467(3) 0.4122(3) 0.05628(6) 0.0196(3) Uani 1 1 d . . .
O31 O 1.0738(2) 0.2145(2) 0.05497(5) 0.0287(2) Uani 1 1 d . . .
H31 H 0.977(4) 0.233(4) 0.0873(9) 0.034 Uiso 1 1 d . . .
O32 O 1.2690(2) 0.5941(2) 0.09614(5) 0.0254(2) Uani 1 1 d . . .
C32 C 1.4151(3) 0.3788(3) 0.00253(6) 0.0215(3) Uani 1 1 d . . .
H32A H 1.2999 0.3393 -0.0354 0.026 Uiso 1 1 calc R . .
H32B H 1.5293 0.2271 0.0067 0.026 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3382(17) . ?
N11 C16 1.3410(17) . ?
C12 C13 1.3934(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3898(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3904(17) . ?
C14 C17 1.5015(16) . ?
C15 C16 1.3830(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2395(15) . ?
C17 N17 1.3416(16) . ?
N17 C21 1.4587(15) . ?
N17 H17 0.844(16) . ?
C21 C22 1.5189(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5238(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5241(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.530(2) 2_456 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 O32 1.2092(16) . ?
C31 O31 1.3236(16) . ?
C31 C32 1.5131(18) . ?
O31 H31 0.896(19) . ?
C32 C32 1.515(3) 2_865 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

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 N11 C16 118.18(11) . . ?
N11 C12 C13 122.79(12) . . ?
N11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 118.61(12) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C13 C14 C15 118.58(11) . . ?
C13 C14 C17 123.03(11) . . ?
C15 C14 C17 118.32(11) . . ?
C16 C15 C14 119.02(12) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N11 C16 C15 122.81(12) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O17 C17 N17 122.07(11) . . ?
O17 C17 C14 120.54(11) . . ?
N17 C17 C14 117.39(11) . . ?
C17 N17 C21 120.36(11) . . ?
C17 N17 H17 121.6(11) . . ?
C21 N17 H17 117.2(11) . . ?
N17 C21 C22 111.77(10) . . ?
N17 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N17 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 111.47(10) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 112.99(10) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C24 113.24(13) . 2_456 ?
C23 C24 H24A 108.9 . . ?
C24 C24 H24A 108.9 2_456 . ?
C23 C24 H24B 108.9 . . ?
C24 C24 H24B 108.9 2_456 . ?
H24A C24 H24B 107.7 . . ?
O32 C31 O31 123.89(12) . . ?
O32 C31 C32 124.52(12) . . ?
O31 C31 C32 111.58(12) . . ?
C31 O31 H31 111.4(12) . . ?
C31 C32 C32 112.60(14) . 2_865 ?
C31 C32 H32A 109.1 . . ?
C32 C32 H32A 109.1 2_865 . ?
C31 C32 H32B 109.1 . . ?
C32 C32 H32B 109.1 2_865 . ?
H32A C32 H32B 107.8 . . ?

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 C13 -1.0(2) . . . . ?
N11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 -0.27(19) . . . . ?
C12 C13 C14 C17 176.68(12) . . . . ?
C13 C14 C15 C16 -0.44(19) . . . . ?
C17 C14 C15 C16 -177.53(11) . . . . ?
C12 N11 C16 C15 0.3(2) . . . . ?
C14 C15 C16 N11 0.4(2) . . . . ?
C13 C14 C17 O17 -150.89(13) . . . . ?
C15 C14 C17 O17 26.06(19) . . . . ?
C13 C14 C17 N17 28.76(18) . . . . ?
C15 C14 C17 N17 -154.29(12) . . . . ?
O17 C17 N17 C21 0.9(2) . . . . ?
C14 C17 N17 C21 -178.74(12) . . . . ?
C17 N17 C21 C22 175.81(11) . . . . ?
N17 C21 C22 C23 177.62(11) . . . . ?
C21 C22 C23 C24 -176.40(11) . . . . ?
C22 C23 C24 C24 179.72(14) . . . 2_456 ?
O32 C31 C32 C32 -10.0(2) . . . 2_865 ?
O31 C31 C32 C32 171.07(14) . . . 2_865 ?

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
O31 H31 N11 0.896(19) 1.817(19) 2.7128(15) 178.3(18) .
N17 H17 O17 0.844(16) 2.150(16) 2.9834(14) 169.5(15) 1_545

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        31.64
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 983625'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0813m_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Adip+A44 4-pyridyl-CONH-(CH2)8-NHCO-4-pyridyl, HOOC-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C6 H10 O4)
;
_chemical_formula_sum            'C26 H36 N4 O6'
_chemical_formula_weight         500.59

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                   5.1403(3)
_cell_length_b                   5.2489(3)
_cell_length_c                   22.9829(15)
_cell_angle_alpha                93.859(4)
_cell_angle_beta                 95.267(4)
_cell_angle_gamma                91.289(4)
_cell_volume                     615.82(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3599
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      31.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10595
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         31.41
_reflns_number_total             3955
_reflns_number_gt                3054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N11 N 0.54045(17) 0.49928(16) 0.32660(4) 0.01656(18) Uani 1 1 d . . .
C12 C 0.7315(2) 0.51739(19) 0.29090(5) 0.0166(2) Uani 1 1 d . . .
H12A H 0.8503 0.6600 0.2971 0.020 Uiso 1 1 calc R . .
C13 C 0.7632(2) 0.33745(19) 0.24541(4) 0.0157(2) Uani 1 1 d . . .
H13A H 0.9020 0.3558 0.2213 0.019 Uiso 1 1 calc R . .
C14 C 0.58811(19) 0.12892(18) 0.23561(4) 0.01343(18) Uani 1 1 d . . .
C15 C 0.38967(19) 0.10885(19) 0.27248(4) 0.0156(2) Uani 1 1 d . . .
H15A H 0.2671 -0.0308 0.2670 0.019 Uiso 1 1 calc R . .
C16 C 0.3739(2) 0.29723(19) 0.31758(4) 0.0166(2) Uani 1 1 d . . .
H16A H 0.2396 0.2819 0.3430 0.020 Uiso 1 1 calc R . .
C17 C 0.6314(2) -0.06871(18) 0.18716(4) 0.01440(19) Uani 1 1 d . . .
N17 N 0.42122(17) -0.20437(16) 0.16232(4) 0.01582(18) Uani 1 1 d . . .
H17 H 0.268(3) -0.165(3) 0.1700(6) 0.019 Uiso 1 1 d . . .
O17 O 0.85331(14) -0.10218(14) 0.17156(3) 0.02007(18) Uani 1 1 d . . .
C21 C 0.4505(2) -0.39952(19) 0.11510(4) 0.0163(2) Uani 1 1 d . . .
H21A H 0.5910 -0.5152 0.1278 0.020 Uiso 1 1 calc R . .
H21B H 0.5035 -0.3161 0.0805 0.020 Uiso 1 1 calc R . .
C22 C 0.1996(2) -0.55536(19) 0.09790(5) 0.0161(2) Uani 1 1 d . . .
H22A H 0.0569 -0.4397 0.0866 0.019 Uiso 1 1 calc R . .
H22B H 0.1504 -0.6457 0.1319 0.019 Uiso 1 1 calc R . .
C23 C 0.2325(2) -0.74971(19) 0.04686(5) 0.0160(2) Uani 1 1 d . . .
H23A H 0.2917 -0.6587 0.0139 0.019 Uiso 1 1 calc R . .
H23B H 0.3705 -0.8688 0.0591 0.019 Uiso 1 1 calc R . .
C24 C -0.0173(2) -0.90351(18) 0.02565(4) 0.0160(2) Uani 1 1 d . . .
H24A H -0.1557 -0.7846 0.0136 0.019 Uiso 1 1 calc R . .
H24B H -0.0761 -0.9956 0.0585 0.019 Uiso 1 1 calc R . .
C31 C 0.7540(2) 1.03192(18) 0.41480(4) 0.01529(19) Uani 1 1 d . . .
O31 O 0.55414(15) 0.86659(15) 0.41535(3) 0.02055(18) Uani 1 1 d . . .
H31 H 0.553(3) 0.746(3) 0.3841(6) 0.025 Uiso 1 1 d . . .
O32 O 0.91091(16) 1.01826(15) 0.37838(4) 0.02227(18) Uani 1 1 d . . .
C32 C 0.7568(2) 1.23651(19) 0.46411(5) 0.0175(2) Uani 1 1 d . . .
H32A H 0.7357 1.1536 0.5009 0.021 Uiso 1 1 calc R . .
H32B H 0.6042 1.3453 0.4565 0.021 Uiso 1 1 calc R . .
C33 C 1.0022(2) 1.40678(19) 0.47307(4) 0.0165(2) Uani 1 1 d . . .
H33A H 1.0164 1.5039 0.4380 0.020 Uiso 1 1 calc R . .
H33B H 1.1575 1.2993 0.4779 0.020 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3408(13) . ?
N11 C12 1.3421(13) . ?
C12 C13 1.3845(14) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3943(13) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3912(13) . ?
C14 C17 1.5052(13) . ?
C15 C16 1.3929(13) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.2394(12) . ?
C17 N17 1.3409(13) . ?
N17 C21 1.4618(12) . ?
N17 H17 0.848(14) . ?
C21 C22 1.5180(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5260(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5246(14) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.5277(19) 2_535 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 O32 1.2147(12) . ?
C31 O31 1.3312(12) . ?
C31 C32 1.5067(14) . ?
O31 H31 0.925(15) . ?
C32 C33 1.5195(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.5276(19) 2_786 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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 118.17(9) . . ?
N11 C12 C13 122.91(9) . . ?
N11 C12 H12A 118.5 . . ?
C13 C12 H12A 118.5 . . ?
C12 C13 C14 118.91(9) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C15 C14 C13 118.48(9) . . ?
C15 C14 C17 123.47(9) . . ?
C13 C14 C17 118.00(8) . . ?
C14 C15 C16 118.81(9) . . ?
C14 C15 H15A 120.6 . . ?
C16 C15 H15A 120.6 . . ?
N11 C16 C15 122.71(9) . . ?
N11 C16 H16A 118.6 . . ?
C15 C16 H16A 118.6 . . ?
O17 C17 N17 122.30(9) . . ?
O17 C17 C14 120.57(9) . . ?
N17 C17 C14 117.13(8) . . ?
C17 N17 C21 119.76(8) . . ?
C17 N17 H17 120.9(9) . . ?
C21 N17 H17 118.7(9) . . ?
N17 C21 C22 112.12(8) . . ?
N17 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
N17 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 110.96(8) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 113.39(8) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C24 112.97(10) . 2_535 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_535 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_535 . ?
H24A C24 H24B 107.8 . . ?
O32 C31 O31 123.46(9) . . ?
O32 C31 C32 125.02(9) . . ?
O31 C31 C32 111.51(8) . . ?
C31 O31 H31 110.1(9) . . ?
C31 C32 C33 114.96(8) . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
C33 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C33 111.29(10) . 2_786 ?
C32 C33 H33A 109.4 . . ?
C33 C33 H33A 109.4 2_786 . ?
C32 C33 H33B 109.4 . . ?
C33 C33 H33B 109.4 2_786 . ?
H33A C33 H33B 108.0 . . ?

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 C13 0.09(16) . . . . ?
N11 C12 C13 C14 0.65(16) . . . . ?
C12 C13 C14 C15 -0.66(15) . . . . ?
C12 C13 C14 C17 -178.06(9) . . . . ?
C13 C14 C15 C16 -0.02(15) . . . . ?
C17 C14 C15 C16 177.22(10) . . . . ?
C12 N11 C16 C15 -0.83(16) . . . . ?
C14 C15 C16 N11 0.80(16) . . . . ?
C15 C14 C17 O17 -150.83(10) . . . . ?
C13 C14 C17 O17 26.42(14) . . . . ?
C15 C14 C17 N17 29.06(15) . . . . ?
C13 C14 C17 N17 -153.68(10) . . . . ?
O17 C17 N17 C21 0.00(15) . . . . ?
C14 C17 N17 C21 -179.89(9) . . . . ?
C17 N17 C21 C22 172.67(9) . . . . ?
N17 C21 C22 C23 177.59(9) . . . . ?
C21 C22 C23 C24 -177.22(9) . . . . ?
C22 C23 C24 C24 179.70(11) . . . 2_535 ?
O32 C31 C32 C33 -10.59(16) . . . . ?
O31 C31 C32 C33 170.18(9) . . . . ?
C31 C32 C33 C33 -175.24(11) . . . 2_786 ?

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
O31 H31 N11 0.925(15) 1.782(15) 2.7056(11) 176.3(13) .
N17 H17 O17 0.848(14) 2.170(14) 3.0039(12) 167.9(13) 1_455

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        31.41
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 983626'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0808m_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
A44-Sub 4-pyridyl-CONH-(CH2)8-NHCO-4-pyridyl, HOOC-(CH2)6-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C8 H14 O4)
;
_chemical_formula_sum            'C28 H40 N4 O6'
_chemical_formula_weight         528.64

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                   5.1420(4)
_cell_length_b                   5.2541(4)
_cell_length_c                   24.624(2)
_cell_angle_alpha                89.785(4)
_cell_angle_beta                 87.095(4)
_cell_angle_gamma                88.590(4)
_cell_volume                     664.20(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3917
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      31.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11236
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         0.83
_diffrn_reflns_theta_max         31.88
_reflns_number_total             4009
_reflns_number_gt                2949
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4009
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
N11 N 0.5217(2) 0.3965(2) 0.30287(4) 0.0170(2) Uani 1 1 d . . .
C12 C 0.6868(2) 0.1973(2) 0.29461(5) 0.0169(3) Uani 1 1 d . . .
H12A H 0.8258 0.1740 0.3183 0.020 Uiso 1 1 calc R . .
C13 C 0.6625(2) 0.0229(2) 0.25265(5) 0.0161(2) Uani 1 1 d . . .
H13A H 0.7841 -0.1150 0.2475 0.019 Uiso 1 1 calc R . .
C14 C 0.4565(2) 0.0551(2) 0.21850(5) 0.0137(2) Uani 1 1 d . . .
C15 C 0.2837(2) 0.2602(2) 0.22758(5) 0.0160(2) Uani 1 1 d . . .
H15A H 0.1405 0.2863 0.2051 0.019 Uiso 1 1 calc R . .
C16 C 0.3233(3) 0.4260(2) 0.26988(5) 0.0168(3) Uani 1 1 d . . .
H16A H 0.2052 0.5662 0.2757 0.020 Uiso 1 1 calc R . .
C17 C 0.4048(2) -0.1273(2) 0.17366(5) 0.0143(2) Uani 1 1 d . . .
N17 N 0.6102(2) -0.2553(2) 0.15049(4) 0.0160(2) Uani 1 1 d . . .
H17 H 0.763(3) -0.214(3) 0.1584(7) 0.019 Uiso 1 1 d . . .
O17 O 0.17981(18) -0.15552(18) 0.15918(4) 0.0199(2) Uani 1 1 d . . .
C21 C 0.5725(2) -0.4350(2) 0.10672(5) 0.0164(3) Uani 1 1 d . . .
H21A H 0.5131 -0.3406 0.0746 0.020 Uiso 1 1 calc R . .
H21B H 0.4345 -0.5543 0.1185 0.020 Uiso 1 1 calc R . .
C22 C 0.8197(2) -0.5857(2) 0.09081(5) 0.0157(2) Uani 1 1 d . . .
H22A H 0.8756 -0.6862 0.1224 0.019 Uiso 1 1 calc R . .
H22B H 0.9600 -0.4669 0.0802 0.019 Uiso 1 1 calc R . .
C23 C 0.7767(2) -0.7644(2) 0.04355(5) 0.0160(2) Uani 1 1 d . . .
H23A H 0.6415 -0.8871 0.0550 0.019 Uiso 1 1 calc R . .
H23B H 0.7107 -0.6635 0.0129 0.019 Uiso 1 1 calc R . .
C24 C 1.0226(2) -0.9117(2) 0.02382(5) 0.0161(2) Uani 1 1 d . . .
H24A H 1.0880 -1.0141 0.0543 0.019 Uiso 1 1 calc R . .
H24B H 1.1585 -0.7893 0.0125 0.019 Uiso 1 1 calc R . .
C31 C 0.3259(2) 0.8999(2) 0.38506(5) 0.0157(2) Uani 1 1 d . . .
O31 O 0.52232(19) 0.73113(19) 0.38594(4) 0.0216(2) Uani 1 1 d . . .
H31 H 0.523(3) 0.623(3) 0.3574(7) 0.026 Uiso 1 1 d . . .
O32 O 0.16434(19) 0.90367(19) 0.35073(4) 0.0220(2) Uani 1 1 d . . .
C32 C 0.3338(3) 1.0854(3) 0.43139(5) 0.0193(3) Uani 1 1 d . . .
H32A H 0.4837 1.1974 0.4241 0.023 Uiso 1 1 calc R . .
H32B H 0.3671 0.9878 0.4649 0.023 Uiso 1 1 calc R . .
C33 C 0.0920(3) 1.2526(2) 0.44233(5) 0.0178(3) Uani 1 1 d . . .
H33A H -0.0621 1.1443 0.4478 0.021 Uiso 1 1 calc R . .
H33B H 0.0646 1.3639 0.4105 0.021 Uiso 1 1 calc R . .
C34 C 0.1195(2) 1.4165(2) 0.49274(5) 0.0180(3) Uani 1 1 d . . .
H34A H 0.1544 1.3037 0.5240 0.022 Uiso 1 1 calc R . .
H34B H 0.2718 1.5266 0.4865 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3404(16) . ?
N11 C16 1.3417(16) . ?
C12 C13 1.3959(16) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3922(17) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3912(16) . ?
C14 C17 1.5028(16) . ?
C15 C16 1.3864(16) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.2401(15) . ?
C17 N17 1.3417(15) . ?
N17 C21 1.4588(15) . ?
N17 H17 0.853(17) . ?
C21 C22 1.5158(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5262(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5250(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.529(2) 2_735 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 O32 1.2146(15) . ?
C31 O31 1.3287(15) . ?
C31 C32 1.5058(16) . ?
O31 H31 0.905(18) . ?
C32 C33 1.5182(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5277(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C34 1.521(2) 2_586 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

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 N11 C16 118.38(10) . . ?
N11 C12 C13 122.61(11) . . ?
N11 C12 H12A 118.7 . . ?
C13 C12 H12A 118.7 . . ?
C14 C13 C12 118.68(11) . . ?
C14 C13 H13A 120.7 . . ?
C12 C13 H13A 120.7 . . ?
C15 C14 C13 118.57(10) . . ?
C15 C14 C17 118.19(10) . . ?
C13 C14 C17 123.19(10) . . ?
C16 C15 C14 119.06(11) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
N11 C16 C15 122.69(11) . . ?
N11 C16 H16A 118.7 . . ?
C15 C16 H16A 118.7 . . ?
O17 C17 N17 122.23(11) . . ?
O17 C17 C14 120.41(11) . . ?
N17 C17 C14 117.35(10) . . ?
C17 N17 C21 119.94(10) . . ?
C17 N17 H17 118.9(11) . . ?
C21 N17 H17 120.6(11) . . ?
N17 C21 C22 112.25(10) . . ?
N17 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
N17 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 110.97(10) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 113.39(10) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C24 112.86(13) . 2_735 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_735 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_735 . ?
H24A C24 H24B 107.8 . . ?
O32 C31 O31 123.79(11) . . ?
O32 C31 C32 125.11(11) . . ?
O31 C31 C32 111.10(10) . . ?
C31 O31 H31 111.7(11) . . ?
C31 C32 C33 116.42(10) . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32B 108.2 . . ?
C33 C32 H32B 108.2 . . ?
H32A C32 H32B 107.3 . . ?
C32 C33 C34 110.70(10) . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C34 C34 C33 113.66(13) 2_586 . ?
C34 C34 H34A 108.8 2_586 . ?
C33 C34 H34A 108.8 . . ?
C34 C34 H34B 108.8 2_586 . ?
C33 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?

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 C13 1.1(2) . . . . ?
N11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.12(19) . . . . ?
C12 C13 C14 C17 -177.21(12) . . . . ?
C13 C14 C15 C16 0.48(19) . . . . ?
C17 C14 C15 C16 177.94(12) . . . . ?
C12 N11 C16 C15 -0.4(2) . . . . ?
C14 C15 C16 N11 -0.3(2) . . . . ?
C15 C14 C17 O17 -26.38(18) . . . . ?
C13 C14 C17 O17 150.96(13) . . . . ?
C15 C14 C17 N17 153.54(12) . . . . ?
C13 C14 C17 N17 -29.12(19) . . . . ?
O17 C17 N17 C21 -0.1(2) . . . . ?
C14 C17 N17 C21 -179.97(11) . . . . ?
C17 N17 C21 C22 -172.52(12) . . . . ?
N17 C21 C22 C23 -177.83(11) . . . . ?
C21 C22 C23 C24 177.11(11) . . . . ?
C22 C23 C24 C24 -179.53(13) . . . 2_735 ?
O32 C31 C32 C33 13.3(2) . . . . ?
O31 C31 C32 C33 -167.56(12) . . . . ?
C31 C32 C33 C34 175.85(12) . . . . ?
C32 C33 C34 C34 -178.20(15) . . . 2_586 ?

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
O31 H31 N11 0.905(18) 1.798(18) 2.7026(14) 177.2(17) .
N17 H17 O17 0.853(17) 2.173(17) 3.0067(14) 165.5(15) 1_655

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 983627'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0936m_6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF 305 (4-pyridyl)-CONH-(CH2)8-NHCO-(4-pyridyl), HOOC-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C10 H18 O4)
;
_chemical_formula_sum            'C30 H44 N4 O6'
_chemical_formula_weight         556.69

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                   5.1264(6)
_cell_length_b                   5.2432(6)
_cell_length_c                   26.127(3)
_cell_angle_alpha                85.874(4)
_cell_angle_beta                 89.354(4)
_cell_angle_gamma                88.356(4)
_cell_volume                     700.11(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3178
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      33.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.092
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11866
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         33.11
_reflns_number_total             4577
_reflns_number_gt                3014
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4577
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
N11 N 0.5806(2) 0.3015(3) 0.28462(5) 0.0199(3) Uani 1 1 d . . .
C12 C 0.3762(3) 0.3414(3) 0.25332(6) 0.0207(3) Uani 1 1 d . . .
H12 H 0.2592 0.4809 0.2586 0.025 Uiso 1 1 calc R . .
C13 C 0.3277(3) 0.1890(3) 0.21371(6) 0.0194(3) Uani 1 1 d . . .
H13 H 0.1791 0.2219 0.1926 0.023 Uiso 1 1 calc R . .
C14 C 0.4998(2) -0.0127(3) 0.20533(6) 0.0163(3) Uani 1 1 d . . .
C15 C 0.7117(3) -0.0549(3) 0.23734(6) 0.0190(3) Uani 1 1 d . . .
H15 H 0.8333 -0.1914 0.2325 0.023 Uiso 1 1 calc R . .
C16 C 0.7445(3) 0.1050(3) 0.27674(6) 0.0198(3) Uani 1 1 d . . .
H16 H 0.8891 0.0735 0.2990 0.024 Uiso 1 1 calc R . .
C17 C 0.4391(3) -0.1801(3) 0.16308(6) 0.0168(3) Uani 1 1 d . . .
N17 N 0.6405(2) -0.3010(3) 0.14139(5) 0.0187(3) Uani 1 1 d . . .
H17 H 0.803(4) -0.264(4) 0.1504(7) 0.022 Uiso 1 1 d . . .
O17 O 0.21167(18) -0.2045(2) 0.14969(4) 0.0229(3) Uani 1 1 d . . .
C21 C 0.5937(3) -0.4671(3) 0.10019(6) 0.0183(3) Uani 1 1 d . . .
H21A H 0.5278 -0.3622 0.0698 0.022 Uiso 1 1 calc R . .
H21B H 0.4576 -0.5898 0.1114 0.022 Uiso 1 1 calc R . .
C22 C 0.8383(3) -0.6136(3) 0.08536(6) 0.0187(3) Uani 1 1 d . . .
H22A H 0.9002 -0.7252 0.1152 0.022 Uiso 1 1 calc R . .
H22B H 0.9772 -0.4919 0.0754 0.022 Uiso 1 1 calc R . .
C23 C 0.7857(3) -0.7764(3) 0.04078(6) 0.0183(3) Uani 1 1 d . . .
H23A H 0.6515 -0.9019 0.0515 0.022 Uiso 1 1 calc R . .
H23B H 0.7143 -0.6646 0.0118 0.022 Uiso 1 1 calc R . .
C24 C 1.0271(2) -0.9193(3) 0.02231(6) 0.0182(3) Uani 1 1 d . . .
H24A H 1.0982 -1.0318 0.0512 0.022 Uiso 1 1 calc R . .
H24B H 1.1616 -0.7941 0.0116 0.022 Uiso 1 1 calc R . .
C31 C 0.3987(3) 0.7808(3) 0.36155(6) 0.0194(3) Uani 1 1 d . . .
O31 O 0.5968(2) 0.6096(2) 0.36251(4) 0.0255(3) Uani 1 1 d . . .
H31 H 0.594(4) 0.500(4) 0.3345(8) 0.031 Uiso 1 1 d . . .
O32 O 0.2320(2) 0.7918(2) 0.32932(4) 0.0263(3) Uani 1 1 d . . .
C32 C 0.4161(3) 0.9521(3) 0.40471(6) 0.0217(3) Uani 1 1 d . . .
H32A H 0.5649 1.0662 0.3977 0.026 Uiso 1 1 calc R . .
H32B H 0.4556 0.8447 0.4366 0.026 Uiso 1 1 calc R . .
C33 C 0.1746(3) 1.1168(3) 0.41434(6) 0.0205(3) Uani 1 1 d . . .
H33A H 0.0212 1.0070 0.4193 0.025 Uiso 1 1 calc R . .
H33B H 0.1422 1.2383 0.3842 0.025 Uiso 1 1 calc R . .
C34 C 0.2108(3) 1.2644(3) 0.46174(6) 0.0216(3) Uani 1 1 d . . .
H34A H 0.2526 1.1406 0.4911 0.026 Uiso 1 1 calc R . .
H34B H 0.3626 1.3756 0.4558 0.026 Uiso 1 1 calc R . .
C35 C -0.0227(3) 1.4285(3) 0.47619(6) 0.0217(3) Uani 1 1 d . . .
H35A H -0.1751 1.3183 0.4823 0.026 Uiso 1 1 calc R . .
H35B H -0.0646 1.5538 0.4471 0.026 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3367(18) . ?
N11 C12 1.3388(19) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3856(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(2) . ?
C14 C17 1.500(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2337(16) . ?
C17 N17 1.3381(16) . ?
N17 C21 1.4585(18) . ?
N17 H17 0.899(19) . ?
C21 C22 1.5133(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5199(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.521(3) 2_735 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 O32 1.2037(18) . ?
C31 O31 1.3351(17) . ?
C31 C32 1.496(2) . ?
O31 H31 0.96(2) . ?
C32 C33 1.5178(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.522(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5142(19) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C35 1.522(3) 2_586 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

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 117.96(13) . . ?
N11 C12 C13 123.05(13) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 118.77(13) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 118.59(13) . . ?
C15 C14 C17 123.52(12) . . ?
C13 C14 C17 117.84(12) . . ?
C14 C15 C16 119.06(13) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 122.56(13) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
O17 C17 N17 122.32(13) . . ?
O17 C17 C14 120.54(12) . . ?
N17 C17 C14 117.14(11) . . ?
C17 N17 C21 119.67(11) . . ?
C17 N17 H17 118.6(12) . . ?
C21 N17 H17 121.4(12) . . ?
N17 C21 C22 112.05(11) . . ?
N17 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
N17 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 110.76(11) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 113.44(11) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C24 113.08(14) . 2_735 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_735 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_735 . ?
H24A C24 H24B 107.8 . . ?
O32 C31 O31 122.86(14) . . ?
O32 C31 C32 125.94(13) . . ?
O31 C31 C32 111.19(12) . . ?
C31 O31 H31 113.0(12) . . ?
C31 C32 C33 115.85(12) . . ?
C31 C32 H32A 108.3 . . ?
C33 C32 H32A 108.3 . . ?
C31 C32 H32B 108.3 . . ?
C33 C32 H32B 108.3 . . ?
H32A C32 H32B 107.4 . . ?
C32 C33 C34 110.29(11) . . ?
C32 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
C32 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
C35 C34 C33 114.91(12) . . ?
C35 C34 H34A 108.5 . . ?
C33 C34 H34A 108.5 . . ?
C35 C34 H34B 108.5 . . ?
C33 C34 H34B 108.5 . . ?
H34A C34 H34B 107.5 . . ?
C34 C35 C35 112.96(15) . 2_586 ?
C34 C35 H35A 109.0 . . ?
C35 C35 H35A 109.0 2_586 . ?
C34 C35 H35B 109.0 . . ?
C35 C35 H35B 109.0 2_586 . ?
H35A C35 H35B 107.8 . . ?

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 C13 0.2(2) . . . . ?
N11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C13 C14 C17 178.28(14) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C17 C14 C15 C16 -177.24(14) . . . . ?
C12 N11 C16 C15 0.8(2) . . . . ?
C14 C15 C16 N11 -1.0(2) . . . . ?
C15 C14 C17 O17 150.60(16) . . . . ?
C13 C14 C17 O17 -26.8(2) . . . . ?
C15 C14 C17 N17 -28.8(2) . . . . ?
C13 C14 C17 N17 153.73(14) . . . . ?
O17 C17 N17 C21 0.4(2) . . . . ?
C14 C17 N17 C21 179.82(13) . . . . ?
C17 N17 C21 C22 -172.44(14) . . . . ?
N17 C21 C22 C23 -177.57(13) . . . . ?
C21 C22 C23 C24 177.31(13) . . . . ?
C22 C23 C24 C24 -179.82(16) . . . 2_735 ?
O32 C31 C32 C33 12.8(3) . . . . ?
O31 C31 C32 C33 -167.69(14) . . . . ?
C31 C32 C33 C34 175.37(14) . . . . ?
C32 C33 C34 C35 -177.90(14) . . . . ?
C33 C34 C35 C35 179.87(18) . . . 2_586 ?

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
O31 H31 N11 0.96(2) 1.73(2) 2.6912(17) 178.6(18) .
N17 H17 O17 0.899(19) 2.125(19) 2.9984(16) 163.5(16) 1_655

_diffrn_measured_fraction_theta_max 0.863
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 983628'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0809m_7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
C44-Succ 4-pyridyl-CONH-(CH2)6-NHCO-4-pyridyl, succinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C4 H6 O4)
;
_chemical_formula_sum            'C22 H28 N4 O6'
_chemical_formula_weight         444.48

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                   5.0275(6)
_cell_length_b                   6.9253(9)
_cell_length_c                   16.058(2)
_cell_angle_alpha                89.749(6)
_cell_angle_beta                 81.536(5)
_cell_angle_gamma                80.893(6)
_cell_volume                     545.92(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6620
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      34.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14151
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         34.34
_reflns_number_total             4361
_reflns_number_gt                3593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4361
_refine_ls_number_parameters     161
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.043
_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 0.60311(16) 0.88600(13) 0.66170(5) 0.02743(17) Uani 1 1 d . . .
C12 C 0.66659(16) 0.75206(13) 0.71896(5) 0.02125(15) Uani 1 1 d . . .
H12 H 0.5836 0.6376 0.7222 0.025 Uiso 1 1 calc R . .
C13 C 0.84991(14) 0.77458(11) 0.77388(4) 0.01679(14) Uani 1 1 d . . .
C14 C 0.97401(16) 0.94194(12) 0.76738(5) 0.02040(15) Uani 1 1 d . . .
H14 H 1.1058 0.9588 0.8024 0.024 Uiso 1 1 calc R . .
C15 C 0.9038(2) 1.08344(14) 0.70956(6) 0.02740(18) Uani 1 1 d . . .
H15 H 0.9818 1.2001 0.7053 0.033 Uiso 1 1 calc R . .
C16 C 0.7163(2) 1.04962(15) 0.65804(6) 0.0307(2) Uani 1 1 d . . .
H16 H 0.6660 1.1462 0.6186 0.037 Uiso 1 1 calc R . .
C17 C 0.92872(14) 0.62002(11) 0.83508(4) 0.01662(14) Uani 1 1 d . . .
N17 N 0.74156(13) 0.50757(10) 0.86350(4) 0.01835(13) Uani 1 1 d . . .
H17 H 0.579(2) 0.5387(17) 0.8533(7) 0.022 Uiso 1 1 d . . .
O17 O 1.15666(11) 0.59925(9) 0.85746(4) 0.02275(14) Uani 1 1 d . . .
C21 C 0.80215(15) 0.34397(11) 0.91911(5) 0.01813(14) Uani 1 1 d . . .
H21A H 0.8367 0.3941 0.9735 0.022 Uiso 1 1 calc R . .
H21B H 0.9686 0.2563 0.8933 0.022 Uiso 1 1 calc R . .
C22 C 0.56548(14) 0.22971(11) 0.93438(5) 0.01767(14) Uani 1 1 d . . .
H22A H 0.5299 0.1821 0.8797 0.021 Uiso 1 1 calc R . .
H22B H 0.4000 0.3181 0.9604 0.021 Uiso 1 1 calc R . .
C23 C 0.62023(14) 0.05583(11) 0.99140(5) 0.01794(14) Uani 1 1 d . . .
H23A H 0.6606 0.1030 1.0456 0.022 Uiso 1 1 calc R . .
H23B H 0.7829 -0.0343 0.9647 0.022 Uiso 1 1 calc R . .
C31A C 0.2268(2) 0.63770(19) 0.55737(6) 0.0245(2) Uani 0.8825(13) 1 d PD A 1
O31A O 0.31219(18) 0.80919(14) 0.54469(5) 0.0329(2) Uani 0.8825(13) 1 d PD A 1
H31A H 0.4071 0.8291 0.5817 0.039 Uiso 0.8825(13) 1 calc PR A 1
O32A O 0.27719(18) 0.53117(13) 0.61510(5) 0.03192(19) Uani 0.8825(13) 1 d PD A
1
C32A C 0.0620(2) 0.59195(17) 0.49083(6) 0.0270(2) Uani 0.8825(13) 1 d PD . 1
H32A H 0.1807 0.5761 0.4356 0.032 Uiso 0.8825(13) 1 calc PR A 1
H32B H -0.0855 0.7034 0.4872 0.032 Uiso 0.8825(13) 1 calc PR A 1
C31B C 0.2193(16) 0.5406(13) 0.5881(5) 0.0245(2) Uani 0.1175(13) 1 d PD A 2
O31B O 0.2698(16) 0.7096(12) 0.5611(4) 0.03192(19) Uani 0.1175(13) 1 d PD A 2
H31B H 0.3734 0.7519 0.5907 0.038 Uiso 0.1175(13) 1 calc PR A 2
O32B O 0.2977(14) 0.4557(11) 0.6486(4) 0.0329(2) Uani 0.1175(13) 1 d PD A 2
C32B C 0.0301(15) 0.4503(13) 0.5391(4) 0.0270(2) Uani 0.1175(13) 1 d PD . 2
H32C H 0.1125 0.3129 0.5247 0.032 Uiso 0.1175(13) 1 calc PR A 2
H32D H -0.1443 0.4481 0.5766 0.032 Uiso 0.1175(13) 1 calc PR A 2


_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 C12 1.3391(11) . ?
N11 C16 1.3435(13) . ?
C12 C13 1.3919(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.3972(11) . ?
C13 C17 1.4966(10) . ?
C14 C15 1.3877(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.3889(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2376(9) . ?
C17 N17 1.3426(10) . ?
N17 C21 1.4614(10) . ?
N17 H17 0.852(12) . ?
C21 C22 1.5207(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5243(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.5269(14) 2_657 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31A O32A 1.2131(13) . ?
C31A O31A 1.3302(15) . ?
C31A C32A 1.5086(14) . ?
O31A H31A 0.8400 . ?
C32A C32A 1.514(2) 2_566 ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C31B O32B 1.216(9) . ?
C31B O31B 1.296(10) . ?
C31B C32B 1.526(10) . ?
O31B H31B 0.8400 . ?
C32B C32B 1.477(14) 2_566 ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?

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 N11 C16 118.94(7) . . ?
N11 C12 C13 122.31(8) . . ?
N11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 118.22(7) . . ?
C12 C13 C17 121.87(7) . . ?
C14 C13 C17 119.80(6) . . ?
C15 C14 C13 119.66(7) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 118.08(8) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
N11 C16 C15 122.73(8) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O17 C17 N17 122.65(7) . . ?
O17 C17 C13 120.59(7) . . ?
N17 C17 C13 116.76(6) . . ?
C17 N17 C21 121.52(6) . . ?
C17 N17 H17 119.6(8) . . ?
C21 N17 H17 118.6(8) . . ?
N17 C21 C22 110.51(6) . . ?
N17 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N17 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C23 112.51(6) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C23 112.53(7) . 2_657 ?
C22 C23 H23A 109.1 . . ?
C23 C23 H23A 109.1 2_657 . ?
C22 C23 H23B 109.1 . . ?
C23 C23 H23B 109.1 2_657 . ?
H23A C23 H23B 107.8 . . ?
O32A C31A O31A 124.00(10) . . ?
O32A C31A C32A 124.37(12) . . ?
O31A C31A C32A 111.63(9) . . ?
C31A O31A H31A 109.5 . . ?
C31A C32A C32A 112.43(10) . 2_566 ?
C31A C32A H32A 109.1 . . ?
C32A C32A H32A 109.1 2_566 . ?
C31A C32A H32B 109.1 . . ?
C32A C32A H32B 109.1 2_566 . ?
H32A C32A H32B 107.8 . . ?
O32B C31B O31B 126.8(8) . . ?
O32B C31B C32B 119.2(8) . . ?
O31B C31B C32B 114.0(8) . . ?
C31B O31B H31B 109.5 . . ?
C32B C32B C31B 115.9(9) 2_566 . ?
C32B C32B H32C 108.3 2_566 . ?
C31B C32B H32C 108.3 . . ?
C32B C32B H32D 108.3 2_566 . ?
C31B C32B H32D 108.3 . . ?
H32C C32B H32D 107.4 . . ?

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 C13 -1.24(13) . . . . ?
N11 C12 C13 C14 -1.10(12) . . . . ?
N11 C12 C13 C17 -177.27(7) . . . . ?
C12 C13 C14 C15 2.66(12) . . . . ?
C17 C13 C14 C15 178.91(7) . . . . ?
C13 C14 C15 C16 -1.91(13) . . . . ?
C12 N11 C16 C15 2.07(15) . . . . ?
C14 C15 C16 N11 -0.49(15) . . . . ?
C12 C13 C17 O17 150.16(8) . . . . ?
C14 C13 C17 O17 -25.95(11) . . . . ?
C12 C13 C17 N17 -29.75(10) . . . . ?
C14 C13 C17 N17 154.15(7) . . . . ?
O17 C17 N17 C21 -3.96(12) . . . . ?
C13 C17 N17 C21 175.94(6) . . . . ?
C17 N17 C21 C22 -174.28(7) . . . . ?
N17 C21 C22 C23 179.38(6) . . . . ?
C21 C22 C23 C23 178.51(8) . . . 2_657 ?
O32A C31A C32A C32A 6.47(17) . . . 2_566 ?
O31A C31A C32A C32A -173.94(11) . . . 2_566 ?
O32B C31B C32B C32B -173.0(9) . . . 2_566 ?
O31B C31B C32B C32B 9.7(12) . . . 2_566 ?

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
O31A H31A N11 0.84 1.81 2.6488(10) 176.8 .
O31B H31B N11 0.84 2.06 2.894(7) 173.6 .
N17 H17 O17 0.852(12) 2.089(12) 2.9244(9) 166.8(11) 1_455

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 983629'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf1005m_8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF 300 (3-pyridyl)-COHN-(CH2)6-NHCO-(3-pyridyl), HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C6 H10 O4)
;
_chemical_formula_sum            'C24 H32 N4 O6'
_chemical_formula_weight         472.54

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0282(6)
_cell_length_b                   6.7877(8)
_cell_length_c                   17.522(2)
_cell_angle_alpha                98.124(3)
_cell_angle_beta                 97.604(3)
_cell_angle_gamma                94.605(3)
_cell_volume                     583.82(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2885
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.098
_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8477
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.49
_reflns_number_total             3487
_reflns_number_gt                2567
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3487
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
N11 N 0.6865(2) 0.54088(17) 0.31012(6) 0.0220(2) Uani 1 1 d . . .
C12 C 0.5662(2) 0.37938(19) 0.26106(7) 0.0195(3) Uani 1 1 d . . .
H12 H 0.6483 0.2579 0.2600 0.023 Uiso 1 1 calc R . .
C13 C 0.3261(2) 0.38179(19) 0.21162(7) 0.0179(3) Uani 1 1 d . . .
C14 C 0.2016(3) 0.55806(19) 0.21603(7) 0.0204(3) Uani 1 1 d . . .
H14 H 0.0326 0.5629 0.1853 0.024 Uiso 1 1 calc R . .
C15 C 0.3269(3) 0.7264(2) 0.26576(8) 0.0227(3) Uani 1 1 d . . .
H15 H 0.2474 0.8491 0.2689 0.027 Uiso 1 1 calc R . .
C16 C 0.5706(3) 0.7119(2) 0.31074(8) 0.0229(3) Uani 1 1 d . . .
H16 H 0.6595 0.8285 0.3435 0.027 Uiso 1 1 calc R . .
C17 C 0.1985(2) 0.20049(18) 0.15641(7) 0.0175(2) Uani 1 1 d . . .
N17 N 0.3667(2) 0.07432(16) 0.12859(6) 0.0193(2) Uani 1 1 d . . .
H17 H 0.532(4) 0.109(2) 0.1354(9) 0.023 Uiso 1 1 d . . .
O17 O -0.04858(18) 0.17102(14) 0.13749(5) 0.0238(2) Uani 1 1 d . . .
C21 C 0.2656(2) -0.11096(18) 0.07675(7) 0.0191(3) Uani 1 1 d . . .
H21A H 0.1805 -0.0796 0.0262 0.023 Uiso 1 1 calc R . .
H21B H 0.1263 -0.1847 0.0998 0.023 Uiso 1 1 calc R . .
C22 C 0.4912(2) -0.24162(19) 0.06325(7) 0.0189(3) Uani 1 1 d . . .
H22A H 0.5757 -0.2733 0.1138 0.023 Uiso 1 1 calc R . .
H22B H 0.6310 -0.1674 0.0405 0.023 Uiso 1 1 calc R . .
C23 C 0.3873(2) -0.43498(19) 0.00882(7) 0.0195(3) Uani 1 1 d . . .
H23A H 0.2945 -0.4026 -0.0406 0.023 Uiso 1 1 calc R . .
H23B H 0.2535 -0.5116 0.0328 0.023 Uiso 1 1 calc R . .
C31 C 1.1450(3) 0.2735(2) 0.40265(8) 0.0227(3) Uani 1 1 d . . .
O31 O 1.1251(2) 0.46795(14) 0.40607(6) 0.0272(2) Uani 1 1 d . . .
O32 O 0.9880(2) 0.14667(15) 0.36039(6) 0.0325(3) Uani 1 1 d . . .
C32 C 1.3880(3) 0.2288(2) 0.45503(9) 0.0312(3) Uani 1 1 d . . .
H32A H 1.4179 0.3296 0.5028 0.037 Uiso 1 1 calc R . .
H32B H 1.5480 0.2438 0.4282 0.037 Uiso 1 1 calc R . .
C33 C 1.3674(2) 0.0227(2) 0.47846(8) 0.0212(3) Uani 1 1 d . . .
H33A H 1.3138 -0.0786 0.4312 0.025 Uiso 1 1 calc R . .
H33B H 1.2255 0.0133 0.5123 0.025 Uiso 1 1 calc R . .
H31 H 0.959(3) 0.491(2) 0.3702(9) 0.025 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3395(17) . ?
N11 C12 1.3403(16) . ?
C12 C13 1.3921(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3914(18) . ?
C13 C17 1.4949(17) . ?
C14 C15 1.3855(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3849(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2351(15) . ?
C17 N17 1.3393(16) . ?
N17 C21 1.4551(16) . ?
N17 H17 0.835(17) . ?
C21 C22 1.5174(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5196(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.529(2) 2_645 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31 O32 1.2118(16) . ?
C31 O31 1.3254(16) . ?
C31 C32 1.5061(19) . ?
O31 H31 1.010(17) . ?
C32 C33 1.5124(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.519(2) 2_856 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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 118.14(11) . . ?
N11 C12 C13 122.88(12) . . ?
N11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 118.08(11) . . ?
C14 C13 C17 120.06(11) . . ?
C12 C13 C17 121.84(11) . . ?
C15 C14 C13 119.29(12) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 118.53(12) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 122.95(12) . . ?
N11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
O17 C17 N17 122.40(11) . . ?
O17 C17 C13 121.29(11) . . ?
N17 C17 C13 116.30(10) . . ?
C17 N17 C21 121.32(10) . . ?
C17 N17 H17 120.0(11) . . ?
C21 N17 H17 118.1(11) . . ?
N17 C21 C22 111.16(10) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.43(10) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C23 112.49(13) . 2_645 ?
C22 C23 H23A 109.1 . . ?
C23 C23 H23A 109.1 2_645 . ?
C22 C23 H23B 109.1 . . ?
C23 C23 H23B 109.1 2_645 . ?
H23A C23 H23B 107.8 . . ?
O32 C31 O31 123.34(12) . . ?
O32 C31 C32 124.09(13) . . ?
O31 C31 C32 112.54(11) . . ?
C31 O31 H31 109.8(9) . . ?
C31 C32 C33 114.77(11) . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C33 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 C33 111.85(13) . 2_856 ?
C32 C33 H33A 109.2 . . ?
C33 C33 H33A 109.2 2_856 . ?
C32 C33 H33B 109.2 . . ?
C33 C33 H33B 109.2 2_856 . ?
H33A C33 H33B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -0.58(19) . . . . ?
N11 C12 C13 C14 -2.68(19) . . . . ?
N11 C12 C13 C17 178.89(11) . . . . ?
C12 C13 C14 C15 3.52(18) . . . . ?
C17 C13 C14 C15 -178.02(11) . . . . ?
C13 C14 C15 C16 -1.27(19) . . . . ?
C12 N11 C16 C15 3.05(19) . . . . ?
C14 C15 C16 N11 -2.1(2) . . . . ?
C14 C13 C17 O17 -28.92(18) . . . . ?
C12 C13 C17 O17 149.48(12) . . . . ?
C14 C13 C17 N17 150.59(12) . . . . ?
C12 C13 C17 N17 -31.01(17) . . . . ?
O17 C17 N17 C21 -2.85(19) . . . . ?
C13 C17 N17 C21 177.65(11) . . . . ?
C17 N17 C21 C22 -171.44(11) . . . . ?
N17 C21 C22 C23 -179.72(10) . . . . ?
C21 C22 C23 C23 177.30(13) . . . 2_645 ?
O32 C31 C32 C33 -24.7(2) . . . . ?
O31 C31 C32 C33 157.14(13) . . . . ?
C31 C32 C33 C33 172.01(14) . . . 2_856 ?

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
O31 H31 N11 1.010(17) 1.704(17) 2.7137(15) 177.2(15) .
N17 H17 O17 0.835(17) 2.110(18) 2.9394(14) 172.1(15) 1_655

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        30.49
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 983630'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0934m_9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF 301 (3-pyridyl)-CONH-(CH2)-6-NHCO-(3-pyridyl), HOOC-(CH2)6-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C8 H14 O4)
;
_chemical_formula_sum            'C26 H36 N4 O6'
_chemical_formula_weight         500.59

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                   5.1671(13)
_cell_length_b                   11.646(3)
_cell_length_c                   11.779(4)
_cell_angle_alpha                67.873(11)
_cell_angle_beta                 80.585(12)
_cell_angle_gamma                79.827(12)
_cell_volume                     642.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2473
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      29.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9851
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.57
_reflns_number_total             3328
_reflns_number_gt                1959
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
N11 N 0.1958(3) 0.25786(15) 0.19729(13) 0.0477(4) Uani 1 1 d . . .
C12 C 0.1402(4) 0.19382(17) 0.31680(15) 0.0423(5) Uani 1 1 d . . .
H12 H 0.0080 0.1420 0.3402 0.051 Uiso 1 1 calc R . .
C13 C 0.2691(3) 0.20030(16) 0.40835(15) 0.0367(4) Uani 1 1 d . . .
C14 C 0.4632(4) 0.27779(18) 0.37274(16) 0.0447(5) Uani 1 1 d . . .
H14 H 0.5554 0.2839 0.4313 0.054 Uiso 1 1 calc R . .
C15 C 0.5197(4) 0.34614(19) 0.24970(17) 0.0525(5) Uani 1 1 d . . .
H15 H 0.6488 0.3998 0.2240 0.063 Uiso 1 1 calc R . .
C16 C 0.3818(4) 0.33364(19) 0.16551(17) 0.0507(5) Uani 1 1 d . . .
H16 H 0.4201 0.3803 0.0825 0.061 Uiso 1 1 calc R . .
C17 C 0.1803(3) 0.12805(16) 0.53920(15) 0.0376(4) Uani 1 1 d . . .
N17 N 0.3617(3) 0.08971(16) 0.61867(13) 0.0439(4) Uani 1 1 d . . .
H17 H 0.511(4) 0.101(2) 0.5931(18) 0.053 Uiso 1 1 d . . .
O17 O -0.0516(2) 0.10742(13) 0.57094(11) 0.0509(4) Uani 1 1 d . . .
C21 C 0.3004(4) 0.02447(19) 0.74998(15) 0.0447(5) Uani 1 1 d . . .
H21A H 0.3213 -0.0647 0.7671 0.054 Uiso 1 1 calc R . .
H21B H 0.1175 0.0500 0.7744 0.054 Uiso 1 1 calc R . .
C22 C 0.4773(4) 0.05112(19) 0.82479(15) 0.0450(5) Uani 1 1 d . . .
H22A H 0.4605 0.1406 0.8054 0.054 Uiso 1 1 calc R . .
H22B H 0.6597 0.0234 0.8018 0.054 Uiso 1 1 calc R . .
C23 C 0.4115(4) -0.01273(19) 0.96181(15) 0.0466(5) Uani 1 1 d . . .
H23A H 0.4273 -0.1021 0.9810 0.056 Uiso 1 1 calc R . .
H23B H 0.2292 0.0153 0.9847 0.056 Uiso 1 1 calc R . .
C31 C 0.0569(4) 0.33861(19) -0.09791(16) 0.0490(5) Uani 1 1 d . . .
O31 O -0.0427(3) 0.26164(16) 0.00548(12) 0.0693(5) Uani 1 1 d . . .
H31 H 0.052(5) 0.262(2) 0.072(2) 0.083 Uiso 1 1 d . . .
O32 O 0.2353(4) 0.3930(2) -0.10274(14) 0.1062(9) Uani 1 1 d . . .
C32 C -0.0652(4) 0.3503(2) -0.20893(16) 0.0516(5) Uani 1 1 d . . .
H32A H -0.2517 0.3807 -0.1993 0.062 Uiso 1 1 calc R . .
H32B H -0.0511 0.2682 -0.2141 0.062 Uiso 1 1 calc R . .
C33 C 0.0621(4) 0.4373(2) -0.32782(16) 0.0538(5) Uani 1 1 d . . .
H33A H 0.0542 0.5182 -0.3208 0.065 Uiso 1 1 calc R . .
H33B H 0.2472 0.4050 -0.3384 0.065 Uiso 1 1 calc R . .
C34 C -0.0629(4) 0.45506(19) -0.44159(16) 0.0513(5) Uani 1 1 d . . .
H34A H -0.0504 0.3747 -0.4504 0.062 Uiso 1 1 calc R . .
H34B H -0.2491 0.4855 -0.4306 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.331(2) . ?
N11 C16 1.332(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(2) . ?
C13 C17 1.491(2) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O17 1.233(2) . ?
C17 N17 1.334(2) . ?
N17 C21 1.452(2) . ?
N17 H17 0.80(2) . ?
C21 C22 1.509(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.510(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C23 1.516(3) 2_657 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C31 O32 1.190(2) . ?
C31 O31 1.299(2) . ?
C31 C32 1.494(2) . ?
O31 H31 1.00(3) . ?
C32 C33 1.512(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.511(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C34 1.508(4) 2_564 ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?

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 N11 C16 117.55(14) . . ?
N11 C12 C13 123.45(16) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 117.75(16) . . ?
C14 C13 C17 124.00(14) . . ?
C12 C13 C17 118.18(15) . . ?
C13 C14 C15 119.43(15) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 118.73(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N11 C16 C15 123.07(17) . . ?
N11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
O17 C17 N17 122.55(16) . . ?
O17 C17 C13 120.66(13) . . ?
N17 C17 C13 116.77(15) . . ?
C17 N17 C21 122.83(15) . . ?
C17 N17 H17 118.9(15) . . ?
C21 N17 H17 118.3(15) . . ?
N17 C21 C22 111.74(14) . . ?
N17 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N17 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 112.63(14) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C23 113.23(18) . 2_657 ?
C22 C23 H23A 108.9 . . ?
C23 C23 H23A 108.9 2_657 . ?
C22 C23 H23B 108.9 . . ?
C23 C23 H23B 108.9 2_657 . ?
H23A C23 H23B 107.7 . . ?
O32 C31 O31 121.89(17) . . ?
O32 C31 C32 123.29(17) . . ?
O31 C31 C32 114.80(16) . . ?
C31 O31 H31 107.7(14) . . ?
C31 C32 C33 113.18(16) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.8 . . ?
C34 C33 C32 114.65(16) . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C34 C34 C33 113.61(19) 2_564 . ?
C34 C34 H34A 108.8 2_564 . ?
C33 C34 H34A 108.8 . . ?
C34 C34 H34B 108.8 2_564 . ?
C33 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?

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 C13 -1.4(3) . . . . ?
N11 C12 C13 C14 0.4(3) . . . . ?
N11 C12 C13 C17 177.43(17) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C17 C13 C14 C15 -176.14(18) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C12 N11 C16 C15 1.3(3) . . . . ?
C14 C15 C16 N11 -0.3(3) . . . . ?
C14 C13 C17 O17 147.14(19) . . . . ?
C12 C13 C17 O17 -29.7(3) . . . . ?
C14 C13 C17 N17 -31.8(3) . . . . ?
C12 C13 C17 N17 151.40(18) . . . . ?
O17 C17 N17 C21 -2.3(3) . . . . ?
C13 C17 N17 C21 176.54(16) . . . . ?
C17 N17 C21 C22 -149.55(19) . . . . ?
N17 C21 C22 C23 178.28(17) . . . . ?
C21 C22 C23 C23 179.7(2) . . . 2_657 ?
O32 C31 C32 C33 0.4(3) . . . . ?
O31 C31 C32 C33 -178.06(19) . . . . ?
C31 C32 C33 C34 -177.86(19) . . . . ?
C32 C33 C34 C34 178.4(2) . . . 2_564 ?

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
O31 H31 N11 1.00(3) 1.73(3) 2.728(2) 175(2) .
N17 H17 O17 0.80(2) 2.24(2) 3.021(2) 165.6(19) 1_655

_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 983631'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0820m_10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF 274 3-pyridyl-CONH-(CH2)6-NHCO-3-pyridyl, HOOC-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C10 H18 O4)
;
_chemical_formula_sum            'C28 H40 N4 O6'
_chemical_formula_weight         528.64

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.9817(4)
_cell_length_b                   6.8634(6)
_cell_length_c                   20.0493(16)
_cell_angle_alpha                93.097(4)
_cell_angle_beta                 90.233(4)
_cell_angle_gamma                98.285(4)
_cell_volume                     677.32(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3907
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      31.58

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11823
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         31.64
_reflns_number_total             4462
_reflns_number_gt                3482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4462
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1571
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
N11 N 0.5671(2) 0.86077(14) 0.23380(5) 0.0190(2) Uani 1 1 d . . .
C12 C 0.4618(2) 0.72603(15) 0.27603(5) 0.0171(2) Uani 1 1 d . . .
H12A H 0.5344 0.6055 0.2768 0.021 Uiso 1 1 calc R . .
C13 C 0.2503(2) 0.75571(15) 0.31882(5) 0.0150(2) Uani 1 1 d . . .
C14 C 0.1367(2) 0.92827(16) 0.31523(5) 0.0175(2) Uani 1 1 d . . .
H14A H -0.0146 0.9494 0.3419 0.021 Uiso 1 1 calc R . .
C15 C 0.2468(2) 1.06921(16) 0.27218(6) 0.0200(2) Uani 1 1 d . . .
H15A H 0.1745 1.1893 0.2693 0.024 Uiso 1 1 calc R . .
C16 C 0.4656(2) 1.03071(16) 0.23330(6) 0.0199(2) Uani 1 1 d . . .
H16A H 0.5463 1.1293 0.2052 0.024 Uiso 1 1 calc R . .
C17 C 0.1395(2) 0.60610(15) 0.36694(5) 0.0153(2) Uani 1 1 d . . .
N17 N 0.31536(18) 0.49517(13) 0.39008(5) 0.01673(19) Uani 1 1 d . . .
H17 H 0.496(3) 0.530(2) 0.3819(7) 0.020 Uiso 1 1 d . . .
O17 O -0.09996(16) 0.58888(12) 0.38412(4) 0.0218(2) Uani 1 1 d . . .
C21 C 0.2301(2) 0.33788(15) 0.43477(5) 0.0163(2) Uani 1 1 d . . .
H21A H 0.0758 0.2468 0.4143 0.020 Uiso 1 1 calc R . .
H21B H 0.1689 0.3949 0.4775 0.020 Uiso 1 1 calc R . .
C22 C 0.4633(2) 0.22520(15) 0.44793(5) 0.0163(2) Uani 1 1 d . . .
H22A H 0.6153 0.3166 0.4692 0.020 Uiso 1 1 calc R . .
H22B H 0.5277 0.1726 0.4049 0.020 Uiso 1 1 calc R . .
C23 C 0.3819(2) 0.05551(15) 0.49291(5) 0.0165(2) Uani 1 1 d . . .
H23A H 0.2320 -0.0371 0.4713 0.020 Uiso 1 1 calc R . .
H23B H 0.3144 0.1078 0.5357 0.020 Uiso 1 1 calc R . .
C31 C 0.9646(2) 0.56520(16) 0.14967(6) 0.0187(2) Uani 1 1 d . . .
O31 O 0.93060(19) 0.75207(12) 0.14637(4) 0.0249(2) Uani 1 1 d . . .
H31 H 0.807(4) 0.785(2) 0.1786(8) 0.030 Uiso 1 1 d . . .
O32 O 0.8509(2) 0.45732(13) 0.19003(5) 0.0326(2) Uani 1 1 d . . .
C32 C 1.1597(2) 0.50575(16) 0.09815(6) 0.0220(2) Uani 1 1 d . . .
H32A H 1.3421 0.5786 0.1092 0.026 Uiso 1 1 calc R . .
H32B H 1.1048 0.5475 0.0542 0.026 Uiso 1 1 calc R . .
C33 C 1.1806(2) 0.28767(16) 0.09159(6) 0.0216(2) Uani 1 1 d . . .
H33A H 0.9982 0.2126 0.0822 0.026 Uiso 1 1 calc R . .
H33B H 1.2467 0.2458 0.1344 0.026 Uiso 1 1 calc R . .
C34 C 1.3718(2) 0.23953(16) 0.03606(6) 0.0209(2) Uani 1 1 d . . .
H34A H 1.3002 0.2767 -0.0069 0.025 Uiso 1 1 calc R . .
H34B H 1.5508 0.3209 0.0444 0.025 Uiso 1 1 calc R . .
C35 C 1.4111(2) 0.02370(16) 0.02944(6) 0.0221(2) Uani 1 1 d . . .
H35A H 1.2313 -0.0587 0.0239 0.027 Uiso 1 1 calc R . .
H35B H 1.4947 -0.0115 0.0712 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3369(15) . ?
N11 C12 1.3399(13) . ?
C12 C13 1.3921(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3894(15) . ?
C13 C17 1.4959(14) . ?
C14 C15 1.3867(15) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3901(17) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.2340(13) . ?
C17 N17 1.3378(13) . ?
N17 C21 1.4575(13) . ?
N17 H17 0.913(16) . ?
C21 C22 1.5150(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5214(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.525(2) 2_656 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31 O32 1.2130(14) . ?
C31 O31 1.3228(14) . ?
C31 C32 1.5018(16) . ?
O31 H31 0.935(19) . ?
C32 C33 1.5140(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5217(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5207(15) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C35 1.528(2) 2_855 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

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 118.45(10) . . ?
N11 C12 C13 122.58(10) . . ?
N11 C12 H12A 118.7 . . ?
C13 C12 H12A 118.7 . . ?
C14 C13 C12 118.40(9) . . ?
C14 C13 C17 119.59(9) . . ?
C12 C13 C17 122.00(9) . . ?
C15 C14 C13 119.19(10) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 118.44(10) . . ?
C14 C15 H15A 120.8 . . ?
C16 C15 H15A 120.8 . . ?
N11 C16 C15 122.78(10) . . ?
N11 C16 H16A 118.6 . . ?
C15 C16 H16A 118.6 . . ?
O17 C17 N17 122.75(10) . . ?
O17 C17 C13 121.24(9) . . ?
N17 C17 C13 116.01(9) . . ?
C17 N17 C21 121.43(9) . . ?
C17 N17 H17 118.5(9) . . ?
C21 N17 H17 119.6(9) . . ?
N17 C21 C22 110.14(8) . . ?
N17 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
N17 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C23 112.11(8) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C23 112.03(10) . 2_656 ?
C22 C23 H23A 109.2 . . ?
C23 C23 H23A 109.2 2_656 . ?
C22 C23 H23B 109.2 . . ?
C23 C23 H23B 109.2 2_656 . ?
H23A C23 H23B 107.9 . . ?
O32 C31 O31 123.21(11) . . ?
O32 C31 C32 124.93(10) . . ?
O31 C31 C32 111.85(9) . . ?
C31 O31 H31 110.3(9) . . ?
C31 C32 C33 115.48(9) . . ?
C31 C32 H32A 108.4 . . ?
C33 C32 H32A 108.4 . . ?
C31 C32 H32B 108.4 . . ?
C33 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C34 111.89(9) . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33B 109.2 . . ?
C34 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C35 C34 C33 114.13(9) . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 C35 113.18(11) . 2_855 ?
C34 C35 H35A 108.9 . . ?
C35 C35 H35A 108.9 2_855 . ?
C34 C35 H35B 108.9 . . ?
C35 C35 H35B 108.9 2_855 . ?
H35A C35 H35B 107.8 . . ?

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 C13 0.51(16) . . . . ?
N11 C12 C13 C14 2.97(16) . . . . ?
N11 C12 C13 C17 -178.42(9) . . . . ?
C12 C13 C14 C15 -3.61(15) . . . . ?
C17 C13 C14 C15 177.75(9) . . . . ?
C13 C14 C15 C16 0.96(16) . . . . ?
C12 N11 C16 C15 -3.40(17) . . . . ?
C14 C15 C16 N11 2.66(17) . . . . ?
C14 C13 C17 O17 28.41(15) . . . . ?
C12 C13 C17 O17 -150.18(11) . . . . ?
C14 C13 C17 N17 -151.09(10) . . . . ?
C12 C13 C17 N17 30.32(14) . . . . ?
O17 C17 N17 C21 3.44(17) . . . . ?
C13 C17 N17 C21 -177.07(9) . . . . ?
C17 N17 C21 C22 174.87(10) . . . . ?
N17 C21 C22 C23 -178.43(9) . . . . ?
C21 C22 C23 C23 -179.01(11) . . . 2_656 ?
O32 C31 C32 C33 8.70(18) . . . . ?
O31 C31 C32 C33 -171.60(10) . . . . ?
C31 C32 C33 C34 177.18(10) . . . . ?
C32 C33 C34 C35 177.20(10) . . . . ?
C33 C34 C35 C35 176.25(12) . . . 2_855 ?

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
O31 H31 N11 0.935(19) 1.748(19) 2.6802(13) 175.0(15) .
N17 H17 O17 0.913(16) 1.997(16) 2.8953(12) 167.6(13) 1_655

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        31.64
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 983632'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sf0833m_11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
SF10 3-pyridyl-CONH-(CH2)6-NHCO-3-pyridyl, HOOC-(CH2)10-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C12 H22 O4)
;
_chemical_formula_sum            'C30 H44 N4 O6'
_chemical_formula_weight         556.69

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.9821(4)
_cell_length_b                   6.8797(6)
_cell_length_c                   21.4410(17)
_cell_angle_alpha                87.936(6)
_cell_angle_beta                 86.223(6)
_cell_angle_gamma                81.469(5)
_cell_volume                     724.93(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      31.46

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14792
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         31.50
_reflns_number_total             4826
_reflns_number_gt                3271
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4826
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
N11 N 0.4847(2) 0.92526(16) 0.25039(5) 0.0201(2) Uani 1 1 d . . .
C12 C 0.5816(3) 0.78012(18) 0.29001(6) 0.0185(2) Uani 1 1 d . . .
H12A H 0.5096 0.6597 0.2907 0.022 Uiso 1 1 calc R . .
C13 C 0.7841(2) 0.79979(17) 0.33023(6) 0.0166(2) Uani 1 1 d . . .
C14 C 0.8973(3) 0.97306(18) 0.32671(6) 0.0193(3) Uani 1 1 d . . .
H14A H 1.0431 0.9877 0.3517 0.023 Uiso 1 1 calc R . .
C15 C 0.7958(3) 1.12439(19) 0.28638(6) 0.0218(3) Uani 1 1 d . . .
H15A H 0.8683 1.2448 0.2838 0.026 Uiso 1 1 calc R . .
C16 C 0.5856(3) 1.09569(18) 0.24986(6) 0.0210(3) Uani 1 1 d . . .
H16A H 0.5103 1.2009 0.2235 0.025 Uiso 1 1 calc R . .
C17 C 0.8853(2) 0.63837(17) 0.37521(6) 0.0169(2) Uani 1 1 d . . .
N17 N 0.7070(2) 0.52160(15) 0.39684(5) 0.0189(2) Uani 1 1 d . . .
H17 H 0.539(4) 0.551(2) 0.3900(7) 0.023 Uiso 1 1 d . . .
O17 O 1.12217(19) 0.61729(14) 0.39148(4) 0.0234(2) Uani 1 1 d . . .
C21 C 0.7826(3) 0.35341(17) 0.43878(6) 0.0182(2) Uani 1 1 d . . .
H21A H 0.8349 0.4000 0.4788 0.022 Uiso 1 1 calc R . .
H21B H 0.9414 0.2672 0.4198 0.022 Uiso 1 1 calc R . .
C22 C 0.5473(3) 0.23770(18) 0.45115(6) 0.0185(2) Uani 1 1 d . . .
H22A H 0.4918 0.1957 0.4108 0.022 Uiso 1 1 calc R . .
H22B H 0.3906 0.3240 0.4710 0.022 Uiso 1 1 calc R . .
C23 C 0.6191(3) 0.05714(17) 0.49329(6) 0.0182(2) Uani 1 1 d . . .
H23A H 0.6779 0.0989 0.5333 0.022 Uiso 1 1 calc R . .
H23B H 0.7736 -0.0304 0.4731 0.022 Uiso 1 1 calc R . .
C31 C 0.1059(3) 0.65026(18) 0.17149(6) 0.0196(3) Uani 1 1 d . . .
O31 O 0.1390(2) 0.83826(14) 0.16831(5) 0.0262(2) Uani 1 1 d . . .
H31 H 0.240(4) 0.867(3) 0.1967(8) 0.031 Uiso 1 1 d . . .
O32 O 0.2105(2) 0.53299(15) 0.20941(5) 0.0336(3) Uani 1 1 d . . .
C32 C -0.0786(3) 0.60366(18) 0.12313(6) 0.0222(3) Uani 1 1 d . . .
H32A H -0.0131 0.6539 0.0819 0.027 Uiso 1 1 calc R . .
H32B H -0.2629 0.6755 0.1330 0.027 Uiso 1 1 calc R . .
C33 C -0.0997(3) 0.38741(19) 0.11778(6) 0.0222(3) Uani 1 1 d . . .
H33A H -0.1752 0.3371 0.1580 0.027 Uiso 1 1 calc R . .
H33B H 0.0843 0.3132 0.1092 0.027 Uiso 1 1 calc R . .
C34 C -0.2804(3) 0.35289(18) 0.06586(6) 0.0215(3) Uani 1 1 d . . .
H34A H -0.2028 0.4031 0.0258 0.026 Uiso 1 1 calc R . .
H34B H -0.4624 0.4302 0.0743 0.026 Uiso 1 1 calc R . .
C35 C -0.3138(3) 0.13774(19) 0.05851(6) 0.0225(3) Uani 1 1 d . . .
H35A H -0.1316 0.0584 0.0528 0.027 Uiso 1 1 calc R . .
H35B H -0.4040 0.0898 0.0974 0.027 Uiso 1 1 calc R . .
C36 C -0.4794(3) 0.10645(18) 0.00351(6) 0.0219(3) Uani 1 1 d . . .
H36A H -0.3866 0.1517 -0.0354 0.026 Uiso 1 1 calc R . .
H36B H -0.6596 0.1888 0.0087 0.026 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3419(16) . ?
N11 C12 1.3423(16) . ?
C12 C13 1.3940(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3899(17) . ?
C13 C17 1.4960(17) . ?
C14 C15 1.3871(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3888(19) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.2390(15) . ?
C17 N17 1.3342(16) . ?
N17 C21 1.4594(16) . ?
N17 H17 0.851(18) . ?
C21 C22 1.5164(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5223(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.525(2) 2_656 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31 O32 1.2115(16) . ?
C31 O31 1.3267(15) . ?
C31 C32 1.5031(18) . ?
O31 H31 0.862(19) . ?
C32 C33 1.5159(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5232(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5287(17) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5219(18) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C36 1.523(2) 2_455 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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 118.67(11) . . ?
N11 C12 C13 122.37(11) . . ?
N11 C12 H12A 118.8 . . ?
C13 C12 H12A 118.8 . . ?
C14 C13 C12 118.29(11) . . ?
C14 C13 C17 119.96(11) . . ?
C12 C13 C17 121.72(11) . . ?
C15 C14 C13 119.49(12) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C16 118.42(12) . . ?
C14 C15 H15A 120.8 . . ?
C16 C15 H15A 120.8 . . ?
N11 C16 C15 122.59(12) . . ?
N11 C16 H16A 118.7 . . ?
C15 C16 H16A 118.7 . . ?
O17 C17 N17 122.51(11) . . ?
O17 C17 C13 120.99(11) . . ?
N17 C17 C13 116.50(11) . . ?
C17 N17 C21 122.05(11) . . ?
C17 N17 H17 120.4(11) . . ?
C21 N17 H17 117.1(11) . . ?
N17 C21 C22 110.51(10) . . ?
N17 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N17 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C23 112.45(10) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C23 112.45(13) . 2_656 ?
C22 C23 H23A 109.1 . . ?
C23 C23 H23A 109.1 2_656 . ?
C22 C23 H23B 109.1 . . ?
C23 C23 H23B 109.1 2_656 . ?
H23A C23 H23B 107.8 . . ?
O32 C31 O31 123.46(12) . . ?
O32 C31 C32 124.93(12) . . ?
O31 C31 C32 111.61(11) . . ?
C31 O31 H31 112.3(12) . . ?
C31 C32 C33 115.24(11) . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
C33 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C34 111.69(11) . . ?
C32 C33 H33A 109.3 . . ?
C34 C33 H33A 109.3 . . ?
C32 C33 H33B 109.3 . . ?
C34 C33 H33B 109.3 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 C35 114.42(11) . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34B 108.7 . . ?
C35 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C36 C35 C34 113.13(11) . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 C36 113.81(14) . 2_455 ?
C35 C36 H36A 108.8 . . ?
C36 C36 H36A 108.8 2_455 . ?
C35 C36 H36B 108.8 . . ?
C36 C36 H36B 108.8 2_455 . ?
H36A C36 H36B 107.7 . . ?

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 C13 -0.43(18) . . . . ?
N11 C12 C13 C14 -3.10(19) . . . . ?
N11 C12 C13 C17 178.52(11) . . . . ?
C12 C13 C14 C15 3.75(18) . . . . ?
C17 C13 C14 C15 -177.83(11) . . . . ?
C13 C14 C15 C16 -1.06(19) . . . . ?
C12 N11 C16 C15 3.36(19) . . . . ?
C14 C15 C16 N11 -2.6(2) . . . . ?
C14 C13 C17 O17 -28.11(18) . . . . ?
C12 C13 C17 O17 150.26(13) . . . . ?
C14 C13 C17 N17 151.27(12) . . . . ?
C12 C13 C17 N17 -30.37(17) . . . . ?
O17 C17 N17 C21 -3.40(19) . . . . ?
C13 C17 N17 C21 177.24(11) . . . . ?
C17 N17 C21 C22 -175.07(11) . . . . ?
N17 C21 C22 C23 178.38(10) . . . . ?
C21 C22 C23 C23 178.95(13) . . . 2_656 ?
O32 C31 C32 C33 -8.2(2) . . . . ?
O31 C31 C32 C33 172.55(11) . . . . ?
C31 C32 C33 C34 -177.49(12) . . . . ?
C32 C33 C34 C35 -179.18(12) . . . . ?
C33 C34 C35 C36 -176.08(12) . . . . ?
C34 C35 C36 C36 -178.56(14) . . . 2_455 ?

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
O31 H31 N11 0.862(19) 1.826(19) 2.6839(15) 173.7(17) .
N17 H17 O17 0.851(18) 2.060(18) 2.8993(14) 169.1(15) 1_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.061

#END

_database_code_depnum_ccdc_archive 'CCDC 983633'
