# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_34Mal
_database_code_depnum_ccdc_archive 'CCDC 1478923'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-B-Mal (3-pyridyl)-CONH-N=CH-(4-pyridyl), HOOC-(CH2)-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C3 H4 O4)
;
_chemical_formula_sum            'C15 H14 N4 O5'
_chemical_formula_weight         330.30

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                   7.0290(10)
_cell_length_b                   10.5537(15)
_cell_length_c                   10.8826(15)
_cell_angle_alpha                73.431(5)
_cell_angle_beta                 76.424(5)
_cell_angle_gamma                71.357(5)
_cell_volume                     723.95(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7582
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      32.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.9907
_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_reflns_number            16031
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         32.66
_reflns_number_total             4726
_reflns_number_gt                3644
_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+0.2000P] 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         4726
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.14662(16) 0.34957(11) 1.13741(10) 0.0201(2) Uani 1 1 d . . .
C12 C 0.19869(17) 0.37479(12) 1.00822(11) 0.0178(2) Uani 1 1 d . . .
H12 H 0.1913 0.4669 0.9619 0.021 Uiso 1 1 calc R . .
C13 C 0.26311(16) 0.27272(11) 0.93840(10) 0.0161(2) Uani 1 1 d . . .
C14 C 0.28573(17) 0.13693(12) 1.00676(11) 0.0184(2) Uani 1 1 d . . .
H14 H 0.3299 0.0648 0.9621 0.022 Uiso 1 1 calc R . .
C15 C 0.24301(18) 0.10875(12) 1.14058(11) 0.0201(2) Uani 1 1 d . . .
H15 H 0.2631 0.0167 1.1901 0.024 Uiso 1 1 calc R . .
C16 C 0.17029(18) 0.21775(13) 1.20094(11) 0.0207(2) Uani 1 1 d . . .
H16 H 0.1350 0.1981 1.2928 0.025 Uiso 1 1 calc R . .
C17 C 0.31172(17) 0.30192(12) 0.79435(11) 0.0166(2) Uani 1 1 d . . .
N17 N 0.21317(15) 0.42789(10) 0.73083(9) 0.0176(2) Uani 1 1 d . . .
H17 H 0.118(2) 0.4874(16) 0.7710(15) 0.021 Uiso 1 1 d . . .
O17 O 0.43211(13) 0.21457(9) 0.73891(8) 0.02203(19) Uani 1 1 d . . .
N21 N 0.20451(15) 0.71995(10) 0.13441(9) 0.0182(2) Uani 1 1 d . . .
C22 C 0.31208(17) 0.59361(12) 0.18639(11) 0.0183(2) Uani 1 1 d . . .
H22 H 0.3995 0.5378 0.1297 0.022 Uiso 1 1 calc R . .
C23 C 0.30138(17) 0.54091(12) 0.31886(11) 0.0174(2) Uani 1 1 d . . .
H23 H 0.3802 0.4510 0.3525 0.021 Uiso 1 1 calc R . .
C24 C 0.17236(17) 0.62268(11) 0.40196(10) 0.0165(2) Uani 1 1 d . . .
C25 C 0.05769(18) 0.75303(12) 0.34774(11) 0.0193(2) Uani 1 1 d . . .
H25 H -0.0340 0.8102 0.4018 0.023 Uiso 1 1 calc R . .
C26 C 0.07925(17) 0.79789(12) 0.21427(11) 0.0187(2) Uani 1 1 d . . .
H26 H 0.0023 0.8874 0.1778 0.022 Uiso 1 1 calc R . .
C27 C 0.14798(18) 0.57665(12) 0.54311(11) 0.0188(2) Uani 1 1 d . . .
H27 H 0.0512 0.6341 0.5951 0.023 Uiso 1 1 calc R . .
N27 N 0.25471(15) 0.46041(10) 0.59770(9) 0.0175(2) Uani 1 1 d . . .
C31 C 0.30234(17) 0.80390(12) -0.19563(11) 0.0183(2) Uani 1 1 d . . .
O31 O 0.24306(14) 0.86344(9) -0.09799(8) 0.0238(2) Uani 1 1 d . A .
H31 H 0.235(2) 0.7898(17) -0.0107(17) 0.029 Uiso 1 1 d . . .
O32 O 0.33788(16) 0.68189(9) -0.18627(9) 0.0309(2) Uani 1 1 d . A .
C32A C 0.3100(4) 0.9065(4) -0.3234(4) 0.0203(5) Uani 0.837(2) 1 d P A 1
H32A H 0.3515 0.9840 -0.3138 0.024 Uiso 0.837(2) 1 calc PR A 1
H32B H 0.1721 0.9435 -0.3476 0.024 Uiso 0.837(2) 1 calc PR A 1
C33A C 0.4557(3) 0.84562(15) -0.43096(14) 0.0183(3) Uani 0.837(2) 1 d P A 1
O33A O 0.36416(17) 0.80901(13) -0.50271(11) 0.0280(3) Uani 0.837(2) 1 d P A 1
H33A H 0.4504 0.7772 -0.5619 0.034 Uiso 0.837(2) 1 calc PR A 1
O34A O 0.63646(16) 0.83314(12) -0.44952(10) 0.0257(3) Uani 0.837(2) 1 d P A 1
C32B C 0.348(3) 0.914(2) -0.325(2) 0.0203(5) Uani 0.163(2) 1 d P A 2
H32C H 0.2445 1.0023 -0.3211 0.024 Uiso 0.163(2) 1 calc PR A 2
H32D H 0.4822 0.9276 -0.3278 0.024 Uiso 0.163(2) 1 calc PR A 2
C33B C 0.3500(16) 0.8755(10) -0.4490(9) 0.0281(19) Uani 0.163(2) 1 d P A 2
O33B O 0.5347(9) 0.7965(6) -0.4880(5) 0.0268(15) Uani 0.163(2) 1 d P A 2
H33B H 0.6056 0.8466 -0.5387 0.032 Uiso 0.163(2) 1 calc PR A 2
O34B O 0.2140(11) 0.9213(11) -0.5114(8) 0.060(3) Uani 0.163(2) 1 d P 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 1.3374(15) . ?
N11 C16 1.3411(16) . ?
C12 C13 1.3914(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3908(16) . ?
C13 C17 1.4865(15) . ?
C14 C15 1.3800(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3832(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2283(13) . ?
C17 N17 1.3554(15) . ?
N17 N27 1.3725(13) . ?
N17 H17 0.886(16) . ?
N21 C26 1.3389(14) . ?
N21 C22 1.3400(15) . ?
C22 C23 1.3827(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.3946(15) . ?
C23 H23 0.9500 . ?
C24 C25 1.3934(16) . ?
C24 C27 1.4591(16) . ?
C25 C26 1.3811(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.2751(15) . ?
C27 H27 0.9500 . ?
C31 O32 1.2093(14) . ?
C31 O31 1.3050(14) . ?
C31 C32A 1.501(4) . ?
C31 C32B 1.59(2) . ?
O31 H31 1.045(18) . ?
C32A C33A 1.509(4) . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C33A O34A 1.208(2) . ?
C33A O33A 1.3193(19) . ?
O33A H33A 0.8400 . ?
C32B C33B 1.51(2) . ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?
C33B O34B 1.196(13) . ?
C33B O33B 1.346(11) . ?
O33B H33B 0.8400 . ?

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 117.03(10) . . ?
N11 C12 C13 123.21(11) . . ?
N11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C14 C13 C12 118.42(10) . . ?
C14 C13 C17 118.52(10) . . ?
C12 C13 C17 123.05(10) . . ?
C15 C14 C13 118.91(10) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 118.38(11) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N11 C16 C15 123.87(11) . . ?
N11 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
O17 C17 N17 123.43(10) . . ?
O17 C17 C13 120.73(10) . . ?
N17 C17 C13 115.84(9) . . ?
C17 N17 N27 118.05(9) . . ?
C17 N17 H17 122.9(10) . . ?
N27 N17 H17 118.9(10) . . ?
C26 N21 C22 118.54(10) . . ?
N21 C22 C23 122.88(10) . . ?
N21 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C22 C23 C24 118.53(10) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 118.51(10) . . ?
C25 C24 C27 118.47(10) . . ?
C23 C24 C27 123.00(10) . . ?
C26 C25 C24 119.08(10) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 122.45(11) . . ?
N21 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
N27 C27 C24 120.98(10) . . ?
N27 C27 H27 119.5 . . ?
C24 C27 H27 119.5 . . ?
C27 N27 N17 115.17(9) . . ?
O32 C31 O31 124.89(11) . . ?
O32 C31 C32A 123.30(17) . . ?
O31 C31 C32A 111.72(16) . . ?
O32 C31 C32B 125.7(8) . . ?
O31 C31 C32B 109.0(8) . . ?
C32A C31 C32B 10.6(7) . . ?
C31 O31 H31 109.9(9) . . ?
C31 C32A C33A 112.7(2) . . ?
C31 C32A H32A 109.0 . . ?
C33A C32A H32A 109.0 . . ?
C31 C32A H32B 109.0 . . ?
C33A C32A H32B 109.0 . . ?
H32A C32A H32B 107.8 . . ?
O34A C33A O33A 123.93(14) . . ?
O34A C33A C32A 123.34(16) . . ?
O33A C33A C32A 112.73(17) . . ?
C33A O33A H33A 109.5 . . ?
C33B C32B C31 114.8(13) . . ?
C33B C32B H32C 108.6 . . ?
C31 C32B H32C 108.6 . . ?
C33B C32B H32D 108.6 . . ?
C31 C32B H32D 108.6 . . ?
H32C C32B H32D 107.5 . . ?
O34B C33B O33B 124.3(9) . . ?
O34B C33B C32B 124.7(11) . . ?
O33B C33B C32B 110.5(11) . . ?
C33B O33B H33B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 3.95(17) . . . . ?
N11 C12 C13 C14 -3.84(17) . . . . ?
N11 C12 C13 C17 177.09(10) . . . . ?
C12 C13 C14 C15 0.20(16) . . . . ?
C17 C13 C14 C15 179.32(10) . . . . ?
C13 C14 C15 C16 2.94(17) . . . . ?
C12 N11 C16 C15 -0.50(18) . . . . ?
C14 C15 C16 N11 -2.92(18) . . . . ?
C14 C13 C17 O17 -25.42(16) . . . . ?
C12 C13 C17 O17 153.65(11) . . . . ?
C14 C13 C17 N17 153.55(11) . . . . ?
C12 C13 C17 N17 -27.37(16) . . . . ?
O17 C17 N17 N27 -1.82(17) . . . . ?
C13 C17 N17 N27 179.23(9) . . . . ?
C26 N21 C22 C23 -0.88(17) . . . . ?
N21 C22 C23 C24 0.26(17) . . . . ?
C22 C23 C24 C25 0.97(16) . . . . ?
C22 C23 C24 C27 179.33(11) . . . . ?
C23 C24 C25 C26 -1.55(17) . . . . ?
C27 C24 C25 C26 180.00(11) . . . . ?
C22 N21 C26 C25 0.24(17) . . . . ?
C24 C25 C26 N21 0.98(18) . . . . ?
C25 C24 C27 N27 -177.37(11) . . . . ?
C23 C24 C27 N27 4.27(18) . . . . ?
C24 C27 N27 N17 -178.34(10) . . . . ?
C17 N17 N27 C27 175.65(10) . . . . ?
O32 C31 C32A C33A -27.8(2) . . . . ?
O31 C31 C32A C33A 155.51(15) . . . . ?
C32B C31 C32A C33A 79(5) . . . . ?
C31 C32A C33A O34A -83.1(2) . . . . ?
C31 C32A C33A O33A 97.5(2) . . . . ?
O32 C31 C32B C33B 27.1(17) . . . . ?
O31 C31 C32B C33B -160.6(11) . . . . ?
C32A C31 C32B C33B -54(4) . . . . ?
C31 C32B C33B O34B 102.0(16) . . . . ?
C31 C32B C33B O33B -85.7(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 N21 1.045(18) 1.537(18) 2.5533(13) 162.7(15) .
O33A H33A O17 0.84 1.90 2.6700(14) 152.2 2_665
O33B H33B O17 0.84 2.53 2.718(6) 93.6 2_665

_diffrn_measured_fraction_theta_max 0.888
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23Adp
_database_code_depnum_ccdc_archive 'CCDC 1478924'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-A-Adp [2-pyridyl-CONH-N=CH-(3-pyridyl)]2, HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O)2 (C6 H10 O4)
;
_chemical_formula_sum            'C30 H30 N8 O6'
_chemical_formula_weight         598.62

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                   5.9660(5)
_cell_length_b                   7.2613(6)
_cell_length_c                   16.8960(14)
_cell_angle_alpha                89.858(2)
_cell_angle_beta                 80.013(3)
_cell_angle_gamma                79.638(2)
_cell_volume                     708.79(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9042
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      32.05

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  0.9703
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15145
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         32.11
_reflns_number_total             4623
_reflns_number_gt                4145
_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+0.2000P] 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         4623
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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 0.38760(13) 0.15231(11) 0.62652(5) 0.02071(16) Uani 1 1 d . . .
C12 C 0.61056(14) 0.15309(11) 0.59770(5) 0.01696(16) Uani 1 1 d . . .
C13 C 0.78838(15) 0.09028(13) 0.63983(6) 0.02193(18) Uani 1 1 d . . .
H13 H 0.9451 0.0899 0.6164 0.026 Uiso 1 1 calc R . .
C14 C 0.73105(17) 0.02791(14) 0.71732(6) 0.02404(18) Uani 1 1 d . . .
H14 H 0.8479 -0.0149 0.7482 0.029 Uiso 1 1 calc R . .
C15 C 0.50127(17) 0.02953(13) 0.74837(5) 0.02214(18) Uani 1 1 d . . .
H15 H 0.4563 -0.0100 0.8015 0.027 Uiso 1 1 calc R . .
C16 C 0.33705(16) 0.08990(14) 0.70068(5) 0.02318(18) Uani 1 1 d . . .
H16 H 0.1796 0.0867 0.7219 0.028 Uiso 1 1 calc R . .
C17 C 0.66531(15) 0.22824(12) 0.51496(5) 0.01918(16) Uani 1 1 d . . .
N17 N 0.47532(14) 0.27416(11) 0.47999(4) 0.01969(15) Uani 1 1 d . . .
H17 H 0.342(2) 0.2573(18) 0.5097(8) 0.024 Uiso 1 1 d . . .
O17 O 0.86038(12) 0.24572(11) 0.48454(4) 0.02922(17) Uani 1 1 d . . .
N21 N 0.47492(14) 0.46862(11) 0.16197(5) 0.02112(16) Uani 1 1 d . . .
C22 C 0.48274(15) 0.42130(12) 0.23799(5) 0.01916(16) Uani 1 1 d . . .
H22 H 0.6287 0.3722 0.2521 0.023 Uiso 1 1 calc R . .
C23 C 0.28622(15) 0.44087(12) 0.29747(5) 0.01780(16) Uani 1 1 d . . .
C24 C 0.07284(16) 0.51004(14) 0.27571(6) 0.02267(18) Uani 1 1 d . . .
H24 H -0.0656 0.5218 0.3143 0.027 Uiso 1 1 calc R . .
C25 C 0.06484(17) 0.56154(14) 0.19698(6) 0.02456(19) Uani 1 1 d . . .
H25 H -0.0786 0.6112 0.1811 0.029 Uiso 1 1 calc R . .
C26 C 0.26812(17) 0.53950(13) 0.14218(5) 0.02265(18) Uani 1 1 d . . .
H26 H 0.2623 0.5756 0.0884 0.027 Uiso 1 1 calc R . .
C27 C 0.29676(15) 0.38142(12) 0.37960(5) 0.01953(17) Uani 1 1 d . . .
H27 H 0.1577 0.3755 0.4159 0.023 Uiso 1 1 calc R . .
N27 N 0.49195(13) 0.33722(10) 0.40309(4) 0.01908(15) Uani 1 1 d . . .
C31 C 0.99185(16) 0.21973(12) 0.07027(5) 0.02003(17) Uani 1 1 d . . .
O31 O 0.83732(12) 0.35646(10) 0.04834(4) 0.02416(15) Uani 1 1 d . . .
H31 H 0.710(2) 0.3901(19) 0.0917(9) 0.029 Uiso 1 1 d . . .
C32 C 1.20304(16) 0.16692(12) 0.00617(5) 0.02093(17) Uani 1 1 d . . .
H32A H 1.2605 0.2822 -0.0123 0.025 Uiso 1 1 calc R . .
H32B H 1.1584 0.1090 -0.0404 0.025 Uiso 1 1 calc R . .
O32 O 0.96264(13) 0.14499(11) 0.13470(4) 0.02810(17) Uani 1 1 d . . .
C33 C 1.39872(16) 0.03166(13) 0.03382(5) 0.02202(18) Uani 1 1 d . . .
H33A H 1.4534 0.0933 0.0771 0.026 Uiso 1 1 calc R . .
H33B H 1.3387 -0.0795 0.0564 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 1.3347(11) . ?
N11 C12 1.3359(11) . ?
C12 C13 1.3880(12) . ?
C12 C17 1.5036(12) . ?
C13 C14 1.3906(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3782(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.3852(12) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2165(11) . ?
C17 N17 1.3566(11) . ?
N17 N27 1.3698(10) . ?
N17 H17 0.893(14) . ?
N21 C22 1.3352(11) . ?
N21 C26 1.3464(12) . ?
C22 C23 1.3917(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.3927(12) . ?
C23 C27 1.4605(11) . ?
C24 C25 1.3874(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.3766(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.2814(12) . ?
C27 H27 0.9500 . ?
C31 O32 1.2146(11) . ?
C31 O31 1.3268(11) . ?
C31 C32 1.5042(13) . ?
O31 H31 0.957(14) . ?
C32 C33 1.5233(13) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.5171(18) 2_855 ?
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 116.93(8) . . ?
N11 C12 C13 123.71(8) . . ?
N11 C12 C17 116.57(7) . . ?
C13 C12 C17 119.72(8) . . ?
C12 C13 C14 118.26(8) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 118.63(8) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 118.76(8) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N11 C16 C15 123.68(8) . . ?
N11 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
O17 C17 N17 125.07(8) . . ?
O17 C17 C12 122.28(8) . . ?
N17 C17 C12 112.65(7) . . ?
C17 N17 N27 121.25(7) . . ?
C17 N17 H17 115.8(8) . . ?
N27 N17 H17 123.0(8) . . ?
C22 N21 C26 118.54(8) . . ?
N21 C22 C23 122.84(8) . . ?
N21 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C22 C23 C24 118.00(8) . . ?
C22 C23 C27 122.11(8) . . ?
C24 C23 C27 119.80(8) . . ?
C25 C24 C23 119.20(8) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 118.95(8) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 122.45(8) . . ?
N21 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
N27 C27 C23 120.56(8) . . ?
N27 C27 H27 119.7 . . ?
C23 C27 H27 119.7 . . ?
C27 N27 N17 113.90(7) . . ?
O32 C31 O31 123.20(9) . . ?
O32 C31 C32 124.33(8) . . ?
O31 C31 C32 112.46(7) . . ?
C31 O31 H31 109.7(8) . . ?
C31 C32 C33 113.77(7) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C33 C33 C32 112.57(9) 2_855 . ?
C33 C33 H33A 109.1 2_855 . ?
C32 C33 H33A 109.1 . . ?
C33 C33 H33B 109.1 2_855 . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 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 1.17(14) . . . . ?
C16 N11 C12 C17 -178.47(8) . . . . ?
N11 C12 C13 C14 -1.90(14) . . . . ?
C17 C12 C13 C14 177.73(8) . . . . ?
C12 C13 C14 C15 0.63(14) . . . . ?
C13 C14 C15 C16 1.17(14) . . . . ?
C12 N11 C16 C15 0.83(14) . . . . ?
C14 C15 C16 N11 -2.00(15) . . . . ?
N11 C12 C17 O17 175.68(9) . . . . ?
C13 C12 C17 O17 -3.98(13) . . . . ?
N11 C12 C17 N17 -3.78(11) . . . . ?
C13 C12 C17 N17 176.57(8) . . . . ?
O17 C17 N17 N27 3.51(14) . . . . ?
C12 C17 N17 N27 -177.05(7) . . . . ?
C26 N21 C22 C23 0.47(13) . . . . ?
N21 C22 C23 C24 1.09(13) . . . . ?
N21 C22 C23 C27 177.49(8) . . . . ?
C22 C23 C24 C25 -1.88(13) . . . . ?
C27 C23 C24 C25 -178.37(8) . . . . ?
C23 C24 C25 C26 1.18(14) . . . . ?
C22 N21 C26 C25 -1.24(14) . . . . ?
C24 C25 C26 N21 0.41(15) . . . . ?
C22 C23 C27 N27 11.46(13) . . . . ?
C24 C23 C27 N27 -172.20(8) . . . . ?
C23 C27 N27 N17 -176.46(7) . . . . ?
C17 N17 N27 C27 -177.53(8) . . . . ?
O32 C31 C32 C33 -9.61(13) . . . . ?
O31 C31 C32 C33 171.31(8) . . . . ?
C31 C32 C33 C33 175.22(9) . . . 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 N21 0.957(14) 1.685(15) 2.6379(10) 173.8(13) .

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.081
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23Pim
_database_code_depnum_ccdc_archive 'CCDC 1478935'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-A-Pim (2-pyridyl)-CONH-N=CH-(3-pyridyl), HOOC-(CH2)5-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C7 H12 O4)
;
_chemical_formula_sum            'C19 H22 N4 O5'
_chemical_formula_weight         386.41

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.5981(7)
_cell_length_b                   45.389(5)
_cell_length_c                   7.3036(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.469(5)
_cell_angle_gamma                90.00
_cell_volume                     1835.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7884
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      31.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_T_max  0.9938
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31436
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         32.11
_reflns_number_total             5805
_reflns_number_gt                4314
_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)+(0.0800P)²+0.5000P] 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         5805
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.7288(2) 0.75664(2) 0.90360(17) 0.0246(3) Uani 1 1 d . . .
C12 C 0.5126(3) 0.74575(3) 0.83042(19) 0.0212(3) Uani 1 1 d . . .
C13 C 0.3127(3) 0.76277(3) 0.7718(2) 0.0248(3) Uani 1 1 d . . .
H13 H 0.1633 0.7541 0.7207 0.030 Uiso 1 1 calc R . .
C14 C 0.3366(3) 0.79327(3) 0.7901(2) 0.0286(3) Uani 1 1 d . . .
H14 H 0.2025 0.8058 0.7529 0.034 Uiso 1 1 calc R . .
C15 C 0.5574(3) 0.80490(3) 0.8627(2) 0.0288(3) Uani 1 1 d . . .
H15 H 0.5785 0.8256 0.8744 0.035 Uiso 1 1 calc R . .
C16 C 0.7484(3) 0.78596(3) 0.9185(2) 0.0274(3) Uani 1 1 d . . .
H16 H 0.8999 0.7941 0.9696 0.033 Uiso 1 1 calc R . .
C17 C 0.4959(3) 0.71283(3) 0.81799(19) 0.0223(3) Uani 1 1 d . . .
N17 N 0.7051(2) 0.69929(2) 0.87734(17) 0.0245(3) Uani 1 1 d . . .
H17 H 0.8362 0.7098 0.9112 0.029 Uiso 1 1 calc R . .
O17 O 0.3058(2) 0.70013(2) 0.75973(15) 0.0276(2) Uani 1 1 d . . .
N21 N 0.8294(2) 0.57741(2) 0.89743(16) 0.0230(3) Uani 1 1 d . . .
C22 C 0.7925(3) 0.60652(3) 0.88465(19) 0.0212(3) Uani 1 1 d . . .
H22 H 0.6392 0.6135 0.8285 0.025 Uiso 1 1 calc R . .
C23 C 0.9705(3) 0.62695(3) 0.95053(18) 0.0205(3) Uani 1 1 d . . .
C24 C 1.1949(3) 0.61648(3) 1.02756(19) 0.0240(3) Uani 1 1 d . . .
H24 H 1.3214 0.6298 1.0713 0.029 Uiso 1 1 calc R . .
C25 C 1.2331(3) 0.58636(3) 1.0401(2) 0.0259(3) Uani 1 1 d . . .
H25 H 1.3858 0.5787 1.0929 0.031 Uiso 1 1 calc R . .
C26 C 1.0456(3) 0.56758(3) 0.97462(19) 0.0245(3) Uani 1 1 d . . .
H26 H 1.0715 0.5469 0.9849 0.029 Uiso 1 1 calc R . .
C27 C 0.9286(3) 0.65861(3) 0.93452(19) 0.0227(3) Uani 1 1 d . . .
H27 H 1.0614 0.6717 0.9609 0.027 Uiso 1 1 calc R . .
N27 N 0.7171(2) 0.66907(2) 0.88583(17) 0.0243(3) Uani 1 1 d . . .
C31 C 0.5067(3) 0.51300(3) 0.76768(18) 0.0212(3) Uani 1 1 d . . .
O31 O 0.4662(2) 0.54193(2) 0.75333(15) 0.0269(2) Uani 1 1 d . . .
H31 H 0.607(4) 0.5531(4) 0.807(3) 0.032 Uiso 1 1 d . . .
O32 O 0.6966(2) 0.50267(2) 0.83916(15) 0.0288(2) Uani 1 1 d . . .
C32 C 0.2908(3) 0.49584(3) 0.68096(19) 0.0208(3) Uani 1 1 d . . .
H32A H 0.2510 0.5019 0.5497 0.025 Uiso 1 1 calc R . .
H32B H 0.1517 0.5012 0.7438 0.025 Uiso 1 1 calc R . .
C33 C 0.3217(3) 0.46262(3) 0.68858(18) 0.0206(3) Uani 1 1 d . . .
H33A H 0.4653 0.4571 0.6318 0.025 Uiso 1 1 calc R . .
H33B H 0.3489 0.4561 0.8194 0.025 Uiso 1 1 calc R . .
C34 C 0.1010(3) 0.44724(3) 0.58720(18) 0.0210(3) Uani 1 1 d . . .
H34A H 0.0746 0.4541 0.4571 0.025 Uiso 1 1 calc R . .
H34B H -0.0417 0.4532 0.6441 0.025 Uiso 1 1 calc R . .
C35 C 0.1175(3) 0.41368(3) 0.58857(19) 0.0205(3) Uani 1 1 d . . .
H35A H 0.2516 0.4073 0.5231 0.025 Uiso 1 1 calc R . .
H35B H 0.1518 0.4065 0.7178 0.025 Uiso 1 1 calc R . .
C36 C -0.1179(3) 0.40048(3) 0.49441(19) 0.0211(3) Uani 1 1 d . . .
H36A H -0.2492 0.4068 0.5630 0.025 Uiso 1 1 calc R . .
H36B H -0.1537 0.4087 0.3678 0.025 Uiso 1 1 calc R . .
C37 C -0.1213(3) 0.36745(3) 0.48104(19) 0.0230(3) Uani 1 1 d . . .
O37 O -0.3116(2) 0.35817(2) 0.36449(15) 0.0291(3) Uani 1 1 d . . .
H37 H -0.303(4) 0.3388(4) 0.348(3) 0.035 Uiso 1 1 d . . .
O38 O 0.0232(3) 0.35104(2) 0.5643(2) 0.0444(4) Uani 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 1.3388(17) . ?
N11 C12 1.3428(19) . ?
C12 C13 1.375(2) . ?
C12 C17 1.4992(17) . ?
C13 C14 1.3953(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2297(18) . ?
C17 N17 1.337(2) . ?
N17 N27 1.3743(15) . ?
N17 H17 0.8800 . ?
N21 C26 1.334(2) . ?
N21 C22 1.3382(16) . ?
C22 C23 1.3938(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 C27 1.4583(18) . ?
C24 C25 1.3849(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.276(2) . ?
C27 H27 0.9500 . ?
C31 O32 1.2080(18) . ?
C31 O31 1.3336(15) . ?
C31 C32 1.498(2) . ?
O31 H31 0.97(2) . ?
C32 C33 1.5180(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.514(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5261(16) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.517(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5023(17) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 O38 1.1976(18) . ?
C37 O37 1.3301(19) . ?
O37 H37 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 117.17(13) . . ?
N11 C12 C13 124.16(12) . . ?
N11 C12 C17 115.81(13) . . ?
C13 C12 C17 120.01(13) . . ?
C12 C13 C14 117.72(15) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 119.04(14) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.07(13) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 122.83(15) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O17 C17 N17 124.67(12) . . ?
O17 C17 C12 122.10(13) . . ?
N17 C17 C12 113.23(13) . . ?
C17 N17 N27 120.52(12) . . ?
C17 N17 H17 119.7 . . ?
N27 N17 H17 119.7 . . ?
C26 N21 C22 118.72(13) . . ?
N21 C22 C23 122.52(14) . . ?
N21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C24 C23 C22 118.19(12) . . ?
C24 C23 C27 119.80(13) . . ?
C22 C23 C27 121.98(14) . . ?
C23 C24 C25 119.21(14) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C26 C25 C24 118.96(15) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 122.37(13) . . ?
N21 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
N27 C27 C23 121.36(13) . . ?
N27 C27 H27 119.3 . . ?
C23 C27 H27 119.3 . . ?
C27 N27 N17 114.88(12) . . ?
O32 C31 O31 123.01(13) . . ?
O32 C31 C32 125.78(12) . . ?
O31 C31 C32 111.19(13) . . ?
C31 O31 H31 111.3(12) . . ?
C31 C32 C33 114.87(12) . . ?
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 . . ?
C34 C33 C32 111.07(12) . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 C35 114.36(12) . . ?
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 110.08(11) . . ?
C36 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
C36 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.2 . . ?
C37 C36 C35 115.18(12) . . ?
C37 C36 H36A 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C37 C36 H36B 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
O38 C37 O37 123.09(13) . . ?
O38 C37 C36 125.88(14) . . ?
O37 C37 C36 111.02(12) . . ?
C37 O37 H37 110.2(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -0.4(2) . . . . ?
C16 N11 C12 C17 -179.22(12) . . . . ?
N11 C12 C13 C14 -0.1(2) . . . . ?
C17 C12 C13 C14 178.67(12) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C12 N11 C16 C15 0.2(2) . . . . ?
C14 C15 C16 N11 0.6(2) . . . . ?
N11 C12 C17 O17 177.39(12) . . . . ?
C13 C12 C17 O17 -1.5(2) . . . . ?
N11 C12 C17 N17 -2.11(17) . . . . ?
C13 C12 C17 N17 179.05(12) . . . . ?
O17 C17 N17 N27 -3.5(2) . . . . ?
C12 C17 N17 N27 175.97(11) . . . . ?
C26 N21 C22 C23 -0.67(19) . . . . ?
N21 C22 C23 C24 1.68(19) . . . . ?
N21 C22 C23 C27 179.54(12) . . . . ?
C22 C23 C24 C25 -1.39(19) . . . . ?
C27 C23 C24 C25 -179.30(12) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C22 N21 C26 C25 -0.63(19) . . . . ?
C24 C25 C26 N21 0.9(2) . . . . ?
C24 C23 C27 N27 -171.18(13) . . . . ?
C22 C23 C27 N27 11.0(2) . . . . ?
C23 C27 N27 N17 179.79(12) . . . . ?
C17 N17 N27 C27 176.21(13) . . . . ?
O32 C31 C32 C33 0.54(19) . . . . ?
O31 C31 C32 C33 179.24(11) . . . . ?
C31 C32 C33 C34 -176.38(11) . . . . ?
C32 C33 C34 C35 -179.94(11) . . . . ?
C33 C34 C35 C36 176.40(11) . . . . ?
C34 C35 C36 C37 177.98(11) . . . . ?
C35 C36 C37 O38 14.1(2) . . . . ?
C35 C36 C37 O37 -166.88(11) . . . . ?

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 N21 0.97(2) 1.72(2) 2.6844(17) 171.4(18) .
O37 H37 O17 0.89(2) 1.93(2) 2.7994(14) 164.1(18) 3_566

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.061

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_34Glu2H2O
_database_code_depnum_ccdc_archive 'CCDC 1478929'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-B-Glu (3-pyridyl)-CONH-N=CH-(4-pyridyl), HOOC-(CH2)3-COOH dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C5 H8 O4) (H2 O)2
;
_chemical_formula_sum            'C17 H22 N4 O7'
_chemical_formula_weight         394.39

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                   10.9929(10)
_cell_length_b                   11.4742(10)
_cell_length_c                   16.1087(14)
_cell_angle_alpha                102.095(3)
_cell_angle_beta                 108.567(4)
_cell_angle_gamma                95.615(3)
_cell_volume                     1853.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      32.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9846
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37645
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         32.60
_reflns_number_total             11890
_reflns_number_gt                7481
_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)+(0.1000P)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         11890
_refine_ls_number_parameters     548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O1W_1 O -0.39827(11) 0.78309(11) 0.39658(9) 0.0398(3) Uani 1 1 d . . .
H1B_1 H -0.364(2) 0.8509(19) 0.4169(15) 0.048 Uiso 1 1 d . . .
H1A_1 H -0.346(2) 0.7415(18) 0.3845(14) 0.048 Uiso 1 1 d . . .
O2W_1 O -0.07274(12) 0.26561(10) 0.27581(8) 0.0360(3) Uani 1 1 d . . .
H2A_1 H -0.036(2) 0.2419(16) 0.3225(15) 0.043 Uiso 1 1 d . . .
H2B_1 H -0.0873(19) 0.1984(18) 0.2316(14) 0.043 Uiso 1 1 d . . .
N11_1 N -0.52405(12) 0.52119(11) 0.12271(8) 0.0278(3) Uani 1 1 d . . .
C12_1 C -0.41984(13) 0.56429(13) 0.19822(10) 0.0256(3) Uani 1 1 d . . .
H12_1 H -0.4173 0.6394 0.2376 0.031 Uiso 1 1 calc R . .
C13_1 C -0.31464(13) 0.50423(12) 0.22189(9) 0.0205(3) Uani 1 1 d . . .
C14_1 C -0.31866(14) 0.39514(12) 0.16286(10) 0.0242(3) Uani 1 1 d . . .
H14_1 H -0.2486 0.3517 0.1762 0.029 Uiso 1 1 calc R . .
C15_1 C -0.42646(14) 0.35078(13) 0.08423(10) 0.0256(3) Uani 1 1 d . . .
H15_1 H -0.4313 0.2767 0.0428 0.031 Uiso 1 1 calc R . .
C16_1 C -0.52647(14) 0.41608(13) 0.06724(10) 0.0268(3) Uani 1 1 d . . .
H16_1 H -0.6005 0.3848 0.0136 0.032 Uiso 1 1 calc R . .
C17_1 C -0.20573(13) 0.56314(12) 0.30848(9) 0.0207(3) Uani 1 1 d . . .
N17_1 N -0.09843(11) 0.51002(11) 0.32637(8) 0.0214(2) Uani 1 1 d . . .
H17_1 H -0.0962(16) 0.4398(15) 0.2981(12) 0.026 Uiso 1 1 d . . .
O17_1 O -0.21148(10) 0.65578(9) 0.36016(7) 0.0276(2) Uani 1 1 d . . .
N21_1 N 0.44234(11) 0.63678(11) 0.65322(8) 0.0252(3) Uani 1 1 d . . .
C22_1 C 0.43151(14) 0.53763(13) 0.58898(10) 0.0279(3) Uani 1 1 d . . .
H22_1 H 0.5018 0.4941 0.5969 0.034 Uiso 1 1 calc R . .
C23_1 C 0.32264(14) 0.49551(13) 0.51141(10) 0.0275(3) Uani 1 1 d . . .
H23_1 H 0.3187 0.4246 0.4671 0.033 Uiso 1 1 calc R . .
C24_1 C 0.21910(13) 0.55819(12) 0.49899(9) 0.0212(3) Uani 1 1 d . . .
C25_1 C 0.22954(13) 0.66127(12) 0.56591(10) 0.0232(3) Uani 1 1 d . . .
H25_1 H 0.1605 0.7062 0.5598 0.028 Uiso 1 1 calc R . .
C26_1 C 0.34221(13) 0.69733(13) 0.64161(10) 0.0243(3) Uani 1 1 d . . .
H26_1 H 0.3489 0.7678 0.6872 0.029 Uiso 1 1 calc R . .
C27_1 C 0.10438(13) 0.51224(12) 0.41667(10) 0.0227(3) Uani 1 1 d . . .
H27_1 H 0.1049 0.4450 0.3710 0.027 Uiso 1 1 calc R . .
N27_1 N 0.00319(11) 0.56238(10) 0.40603(8) 0.0216(2) Uani 1 1 d . . .
C31_1 C -0.81573(13) 0.58525(12) 0.00617(10) 0.0242(3) Uani 1 1 d . . .
O31_1 O -0.71943(11) 0.64436(10) 0.08186(7) 0.0341(3) Uani 1 1 d . . .
H31_1 H -0.6538(19) 0.5957(16) 0.0935(13) 0.041 Uiso 1 1 d . . .
O32_1 O -0.81473(10) 0.48516(9) -0.03648(7) 0.0299(2) Uani 1 1 d . . .
C32_1 C -0.92323(14) 0.65573(13) -0.01822(10) 0.0273(3) Uani 1 1 d . . .
H32A_1 H -0.8850 0.7370 -0.0192 0.033 Uiso 1 1 calc R . .
H32B_1 H -0.9615 0.6671 0.0302 0.033 Uiso 1 1 calc R . .
C33_1 C -1.03242(13) 0.60002(12) -0.10819(10) 0.0243(3) Uani 1 1 d . . .
H33A_1 H -0.9987 0.5976 -0.1586 0.029 Uiso 1 1 calc R . .
H33B_1 H -1.0678 0.5161 -0.1108 0.029 Uiso 1 1 calc R . .
C34_1 C -1.13869(14) 0.67589(13) -0.11724(10) 0.0264(3) Uani 1 1 d . . .
H34A_1 H -1.1700 0.6772 -0.0659 0.032 Uiso 1 1 calc R . .
H34B_1 H -1.0996 0.7601 -0.1113 0.032 Uiso 1 1 calc R . .
C35_1 C -1.25416(14) 0.63625(12) -0.20306(10) 0.0244(3) Uani 1 1 d . . .
O35_1 O -1.34808(10) 0.69849(9) -0.20015(7) 0.0300(2) Uani 1 1 d . . .
H35_1 H -1.4280(19) 0.6737(15) -0.2603(13) 0.036 Uiso 1 1 d . . .
O36_1 O -1.26132(10) 0.55813(9) -0.26939(7) 0.0331(3) Uani 1 1 d . . .
O3W_2 O 0.05328(12) 0.23376(11) 0.44887(8) 0.0394(3) Uani 1 1 d . . .
H3B_2 H 0.072(2) 0.2839(19) 0.4981(15) 0.047 Uiso 1 1 d . . .
H3A_2 H 0.090(2) 0.1789(18) 0.4605(14) 0.047 Uiso 1 1 d . . .
O4W_2 O 0.34367(12) -0.31276(10) 0.35679(8) 0.0357(3) Uani 1 1 d . . .
H4A_2 H 0.428(2) -0.2957(17) 0.3636(13) 0.043 Uiso 1 1 d . . .
H4B_2 H 0.3205(19) -0.3913(18) 0.3239(14) 0.043 Uiso 1 1 d . . .
N11_2 N -0.16057(12) -0.11445(11) 0.26422(8) 0.0269(3) Uani 1 1 d . . .
C12_2 C -0.05674(13) -0.07274(13) 0.34043(10) 0.0247(3) Uani 1 1 d . . .
H12_2 H -0.0591 -0.0042 0.3843 0.030 Uiso 1 1 calc R . .
C13_2 C 0.05450(13) -0.12543(12) 0.35813(9) 0.0213(3) Uani 1 1 d . . .
C14_2 C 0.05565(14) -0.22806(12) 0.29479(10) 0.0238(3) Uani 1 1 d . . .
H14_2 H 0.1292 -0.2674 0.3051 0.029 Uiso 1 1 calc R . .
C15_2 C -0.05274(14) -0.27206(13) 0.21614(10) 0.0265(3) Uani 1 1 d . . .
H15_2 H -0.0548 -0.3422 0.1718 0.032 Uiso 1 1 calc R . .
C16_2 C -0.15727(14) -0.21181(13) 0.20374(10) 0.0260(3) Uani 1 1 d . . .
H16_2 H -0.2305 -0.2413 0.1494 0.031 Uiso 1 1 calc R . .
C17_2 C 0.16555(13) -0.06428(12) 0.44268(9) 0.0213(3) Uani 1 1 d . . .
N17_2 N 0.26966(11) -0.12139(11) 0.46301(8) 0.0224(2) Uani 1 1 d . . .
H17_2 H 0.2801(16) -0.1922(14) 0.4293(11) 0.027 Uiso 1 1 d . . .
O17_2 O 0.16417(10) 0.03355(9) 0.49090(7) 0.0284(2) Uani 1 1 d . . .
N21_2 N 0.81911(11) 0.01066(11) 0.78380(8) 0.0268(3) Uani 1 1 d . . .
C22_2 C 0.80135(14) -0.09549(13) 0.72469(10) 0.0281(3) Uani 1 1 d . . .
H22_2 H 0.8681 -0.1430 0.7351 0.034 Uiso 1 1 calc R . .
C23_2 C 0.68995(14) -0.13959(13) 0.64872(10) 0.0271(3) Uani 1 1 d . . .
H23_2 H 0.6818 -0.2149 0.6075 0.032 Uiso 1 1 calc R . .
C24_2 C 0.59035(13) -0.07232(12) 0.63364(9) 0.0219(3) Uani 1 1 d . . .
C25_2 C 0.60930(14) 0.03959(13) 0.69477(10) 0.0245(3) Uani 1 1 d . . .
H25_2 H 0.5441 0.0889 0.6863 0.029 Uiso 1 1 calc R . .
C26_2 C 0.72452(14) 0.07725(13) 0.76770(10) 0.0255(3) Uani 1 1 d . . .
H26_2 H 0.7375 0.1541 0.8085 0.031 Uiso 1 1 calc R . .
C27_2 C 0.47106(13) -0.12274(12) 0.55524(9) 0.0231(3) Uani 1 1 d . . .
H27_2 H 0.4628 -0.2005 0.5169 0.028 Uiso 1 1 calc R . .
N27_2 N 0.37740(11) -0.06278(10) 0.53782(8) 0.0223(2) Uani 1 1 d . . .
C31_2 C -0.44170(13) -0.03922(13) 0.14511(10) 0.0250(3) Uani 1 1 d . . .
O31_2 O -0.35328(11) 0.01146(10) 0.22606(7) 0.0356(3) Uani 1 1 d . . .
H31_2 H -0.294(2) -0.0417(16) 0.2360(13) 0.043 Uiso 1 1 d . . .
O32_2 O -0.43840(11) -0.13547(9) 0.09849(8) 0.0353(3) Uani 1 1 d . . .
C32_2 C -0.54311(13) 0.03727(12) 0.11770(10) 0.0250(3) Uani 1 1 d . . .
H32A_2 H -0.5028 0.1086 0.1041 0.030 Uiso 1 1 calc R . .
H32B_2 H -0.5711 0.0674 0.1697 0.030 Uiso 1 1 calc R . .
C33_2 C -0.66284(14) -0.02700(12) 0.03641(10) 0.0251(3) Uani 1 1 d . . .
H33A_2 H -0.6371 -0.0544 -0.0171 0.030 Uiso 1 1 calc R . .
H33B_2 H -0.7038 -0.0992 0.0486 0.030 Uiso 1 1 calc R . .
C34_2 C -0.75952(14) 0.05765(13) 0.01692(10) 0.0259(3) Uani 1 1 d . . .
H34A_2 H -0.7860 0.0820 0.0704 0.031 Uiso 1 1 calc R . .
H34B_2 H -0.7148 0.1317 0.0093 0.031 Uiso 1 1 calc R . .
C35_2 C -0.88030(14) 0.00754(13) -0.06493(10) 0.0250(3) Uani 1 1 d . . .
O35_2 O -0.96560(10) 0.08152(9) -0.07157(7) 0.0314(3) Uani 1 1 d . . .
H35_2 H -1.0426(19) 0.0494(16) -0.1321(13) 0.038 Uiso 1 1 d . . .
O36_2 O -0.89855(11) -0.08872(10) -0.11915(7) 0.0354(3) Uani 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
O1W_1 H1B_1 0.78(2) . ?
O1W_1 H1A_1 0.82(2) . ?
O2W_1 H2A_1 0.85(2) . ?
O2W_1 H2B_1 0.89(2) . ?
N11_1 C16_1 1.3344(19) . ?
N11_1 C12_1 1.3365(17) . ?
C12_1 C13_1 1.3938(19) . ?
C12_1 H12_1 0.9500 . ?
C13_1 C14_1 1.3917(19) . ?
C13_1 C17_1 1.4896(18) . ?
C14_1 C15_1 1.3869(19) . ?
C14_1 H14_1 0.9500 . ?
C15_1 C16_1 1.379(2) . ?
C15_1 H15_1 0.9500 . ?
C16_1 H16_1 0.9500 . ?
C17_1 O17_1 1.2259(16) . ?
C17_1 N17_1 1.3578(17) . ?
N17_1 N27_1 1.3741(15) . ?
N17_1 H17_1 0.845(17) . ?
N21_1 C22_1 1.3345(19) . ?
N21_1 C26_1 1.3425(18) . ?
C22_1 C23_1 1.382(2) . ?
C22_1 H22_1 0.9500 . ?
C23_1 C24_1 1.3887(19) . ?
C23_1 H23_1 0.9500 . ?
C24_1 C25_1 1.391(2) . ?
C24_1 C27_1 1.4625(18) . ?
C25_1 C26_1 1.3852(18) . ?
C25_1 H25_1 0.9500 . ?
C26_1 H26_1 0.9500 . ?
C27_1 N27_1 1.2817(17) . ?
C27_1 H27_1 0.9500 . ?
C31_1 O32_1 1.2115(17) . ?
C31_1 O31_1 1.3260(17) . ?
C31_1 C32_1 1.4931(19) . ?
O31_1 H31_1 0.951(19) . ?
C32_1 C33_1 1.5178(19) . ?
C32_1 H32A_1 0.9900 . ?
C32_1 H32B_1 0.9900 . ?
C33_1 C34_1 1.5125(19) . ?
C33_1 H33A_1 0.9900 . ?
C33_1 H33B_1 0.9900 . ?
C34_1 C35_1 1.4951(19) . ?
C34_1 H34A_1 0.9900 . ?
C34_1 H34B_1 0.9900 . ?
C35_1 O36_1 1.2176(18) . ?
C35_1 O35_1 1.3189(17) . ?
O35_1 H35_1 1.042(19) . ?
O3W_2 H3B_2 0.83(2) . ?
O3W_2 H3A_2 0.80(2) . ?
O4W_2 H4A_2 0.89(2) . ?
O4W_2 H4B_2 0.91(2) . ?
N11_2 C16_2 1.3315(19) . ?
N11_2 C12_2 1.3392(17) . ?
C12_2 C13_2 1.3917(19) . ?
C12_2 H12_2 0.9500 . ?
C13_2 C14_2 1.3912(19) . ?
C13_2 C17_2 1.4869(18) . ?
C14_2 C15_2 1.3902(19) . ?
C14_2 H14_2 0.9500 . ?
C15_2 C16_2 1.380(2) . ?
C15_2 H15_2 0.9500 . ?
C16_2 H16_2 0.9500 . ?
C17_2 O17_2 1.2284(16) . ?
C17_2 N17_2 1.3582(17) . ?
N17_2 N27_2 1.3794(15) . ?
N17_2 H17_2 0.918(16) . ?
N21_2 C22_2 1.333(2) . ?
N21_2 C26_2 1.3413(18) . ?
C22_2 C23_2 1.385(2) . ?
C22_2 H22_2 0.9500 . ?
C23_2 C24_2 1.3885(19) . ?
C23_2 H23_2 0.9500 . ?
C24_2 C25_2 1.396(2) . ?
C24_2 C27_2 1.4629(18) . ?
C25_2 C26_2 1.3798(19) . ?
C25_2 H25_2 0.9500 . ?
C26_2 H26_2 0.9500 . ?
C27_2 N27_2 1.2835(17) . ?
C27_2 H27_2 0.9500 . ?
C31_2 O32_2 1.2093(17) . ?
C31_2 O31_2 1.3221(17) . ?
C31_2 C32_2 1.4995(19) . ?
O31_2 H31_2 0.935(19) . ?
C32_2 C33_2 1.5162(19) . ?
C32_2 H32A_2 0.9900 . ?
C32_2 H32B_2 0.9900 . ?
C33_2 C34_2 1.5129(19) . ?
C33_2 H33A_2 0.9900 . ?
C33_2 H33B_2 0.9900 . ?
C34_2 C35_2 1.5000(19) . ?
C34_2 H34A_2 0.9900 . ?
C34_2 H34B_2 0.9900 . ?
C35_2 O36_2 1.2099(17) . ?
C35_2 O35_2 1.3195(17) . ?
O35_2 H35_2 1.03(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1B_1 O1W_1 H1A_1 110(2) . . ?
H2A_1 O2W_1 H2B_1 101.7(16) . . ?
C16_1 N11_1 C12_1 118.14(12) . . ?
N11_1 C12_1 C13_1 123.14(13) . . ?
N11_1 C12_1 H12_1 118.4 . . ?
C13_1 C12_1 H12_1 118.4 . . ?
C14_1 C13_1 C12_1 117.84(12) . . ?
C14_1 C13_1 C17_1 125.14(12) . . ?
C12_1 C13_1 C17_1 117.02(12) . . ?
C15_1 C14_1 C13_1 119.02(13) . . ?
C15_1 C14_1 H14_1 120.5 . . ?
C13_1 C14_1 H14_1 120.5 . . ?
C16_1 C15_1 C14_1 118.88(13) . . ?
C16_1 C15_1 H15_1 120.6 . . ?
C14_1 C15_1 H15_1 120.6 . . ?
N11_1 C16_1 C15_1 122.99(13) . . ?
N11_1 C16_1 H16_1 118.5 . . ?
C15_1 C16_1 H16_1 118.5 . . ?
O17_1 C17_1 N17_1 121.66(12) . . ?
O17_1 C17_1 C13_1 121.93(12) . . ?
N17_1 C17_1 C13_1 116.40(12) . . ?
C17_1 N17_1 N27_1 117.51(11) . . ?
C17_1 N17_1 H17_1 124.0(12) . . ?
N27_1 N17_1 H17_1 117.1(11) . . ?
C22_1 N21_1 C26_1 118.11(12) . . ?
N21_1 C22_1 C23_1 122.92(13) . . ?
N21_1 C22_1 H22_1 118.5 . . ?
C23_1 C22_1 H22_1 118.5 . . ?
C22_1 C23_1 C24_1 119.13(13) . . ?
C22_1 C23_1 H23_1 120.4 . . ?
C24_1 C23_1 H23_1 120.4 . . ?
C23_1 C24_1 C25_1 118.22(12) . . ?
C23_1 C24_1 C27_1 118.47(12) . . ?
C25_1 C24_1 C27_1 123.31(12) . . ?
C26_1 C25_1 C24_1 118.96(13) . . ?
C26_1 C25_1 H25_1 120.5 . . ?
C24_1 C25_1 H25_1 120.5 . . ?
N21_1 C26_1 C25_1 122.66(13) . . ?
N21_1 C26_1 H26_1 118.7 . . ?
C25_1 C26_1 H26_1 118.7 . . ?
N27_1 C27_1 C24_1 120.19(13) . . ?
N27_1 C27_1 H27_1 119.9 . . ?
C24_1 C27_1 H27_1 119.9 . . ?
C27_1 N27_1 N17_1 114.56(11) . . ?
O32_1 C31_1 O31_1 122.72(13) . . ?
O32_1 C31_1 C32_1 125.13(12) . . ?
O31_1 C31_1 C32_1 112.15(12) . . ?
C31_1 O31_1 H31_1 108.3(12) . . ?
C31_1 C32_1 C33_1 115.89(12) . . ?
C31_1 C32_1 H32A_1 108.3 . . ?
C33_1 C32_1 H32A_1 108.3 . . ?
C31_1 C32_1 H32B_1 108.3 . . ?
C33_1 C32_1 H32B_1 108.3 . . ?
H32A_1 C32_1 H32B_1 107.4 . . ?
C34_1 C33_1 C32_1 108.71(11) . . ?
C34_1 C33_1 H33A_1 109.9 . . ?
C32_1 C33_1 H33A_1 109.9 . . ?
C34_1 C33_1 H33B_1 109.9 . . ?
C32_1 C33_1 H33B_1 109.9 . . ?
H33A_1 C33_1 H33B_1 108.3 . . ?
C35_1 C34_1 C33_1 116.52(12) . . ?
C35_1 C34_1 H34A_1 108.2 . . ?
C33_1 C34_1 H34A_1 108.2 . . ?
C35_1 C34_1 H34B_1 108.2 . . ?
C33_1 C34_1 H34B_1 108.2 . . ?
H34A_1 C34_1 H34B_1 107.3 . . ?
O36_1 C35_1 O35_1 123.04(13) . . ?
O36_1 C35_1 C34_1 124.91(13) . . ?
O35_1 C35_1 C34_1 112.02(12) . . ?
C35_1 O35_1 H35_1 112.9(10) . . ?
H3B_2 O3W_2 H3A_2 105(2) . . ?
H4A_2 O4W_2 H4B_2 102.5(17) . . ?
C16_2 N11_2 C12_2 118.16(12) . . ?
N11_2 C12_2 C13_2 122.88(13) . . ?
N11_2 C12_2 H12_2 118.6 . . ?
C13_2 C12_2 H12_2 118.6 . . ?
C14_2 C13_2 C12_2 118.22(12) . . ?
C14_2 C13_2 C17_2 124.90(12) . . ?
C12_2 C13_2 C17_2 116.85(12) . . ?
C15_2 C14_2 C13_2 118.84(13) . . ?
C15_2 C14_2 H14_2 120.6 . . ?
C13_2 C14_2 H14_2 120.6 . . ?
C16_2 C15_2 C14_2 118.65(13) . . ?
C16_2 C15_2 H15_2 120.7 . . ?
C14_2 C15_2 H15_2 120.7 . . ?
N11_2 C16_2 C15_2 123.23(13) . . ?
N11_2 C16_2 H16_2 118.4 . . ?
C15_2 C16_2 H16_2 118.4 . . ?
O17_2 C17_2 N17_2 121.72(12) . . ?
O17_2 C17_2 C13_2 121.86(12) . . ?
N17_2 C17_2 C13_2 116.41(12) . . ?
C17_2 N17_2 N27_2 117.56(11) . . ?
C17_2 N17_2 H17_2 127.1(11) . . ?
N27_2 N17_2 H17_2 115.1(11) . . ?
C22_2 N21_2 C26_2 117.84(12) . . ?
N21_2 C22_2 C23_2 122.95(13) . . ?
N21_2 C22_2 H22_2 118.5 . . ?
C23_2 C22_2 H22_2 118.5 . . ?
C22_2 C23_2 C24_2 119.15(14) . . ?
C22_2 C23_2 H23_2 120.4 . . ?
C24_2 C23_2 H23_2 120.4 . . ?
C23_2 C24_2 C25_2 118.04(12) . . ?
C23_2 C24_2 C27_2 118.41(12) . . ?
C25_2 C24_2 C27_2 123.56(12) . . ?
C26_2 C25_2 C24_2 118.78(13) . . ?
C26_2 C25_2 H25_2 120.6 . . ?
C24_2 C25_2 H25_2 120.6 . . ?
N21_2 C26_2 C25_2 123.20(13) . . ?
N21_2 C26_2 H26_2 118.4 . . ?
C25_2 C26_2 H26_2 118.4 . . ?
N27_2 C27_2 C24_2 120.52(12) . . ?
N27_2 C27_2 H27_2 119.7 . . ?
C24_2 C27_2 H27_2 119.7 . . ?
C27_2 N27_2 N17_2 114.71(11) . . ?
O32_2 C31_2 O31_2 123.08(13) . . ?
O32_2 C31_2 C32_2 124.50(13) . . ?
O31_2 C31_2 C32_2 112.40(12) . . ?
C31_2 O31_2 H31_2 105.7(12) . . ?
C31_2 C32_2 C33_2 114.79(11) . . ?
C31_2 C32_2 H32A_2 108.6 . . ?
C33_2 C32_2 H32A_2 108.6 . . ?
C31_2 C32_2 H32B_2 108.6 . . ?
C33_2 C32_2 H32B_2 108.6 . . ?
H32A_2 C32_2 H32B_2 107.5 . . ?
C34_2 C33_2 C32_2 110.02(11) . . ?
C34_2 C33_2 H33A_2 109.7 . . ?
C32_2 C33_2 H33A_2 109.7 . . ?
C34_2 C33_2 H33B_2 109.7 . . ?
C32_2 C33_2 H33B_2 109.7 . . ?
H33A_2 C33_2 H33B_2 108.2 . . ?
C35_2 C34_2 C33_2 115.71(12) . . ?
C35_2 C34_2 H34A_2 108.4 . . ?
C33_2 C34_2 H34A_2 108.4 . . ?
C35_2 C34_2 H34B_2 108.4 . . ?
C33_2 C34_2 H34B_2 108.4 . . ?
H34A_2 C34_2 H34B_2 107.4 . . ?
O36_2 C35_2 O35_2 123.35(13) . . ?
O36_2 C35_2 C34_2 124.75(13) . . ?
O35_2 C35_2 C34_2 111.90(12) . . ?
C35_2 O35_2 H35_2 110.0(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16_1 N11_1 C12_1 C13_1 -0.6(2) . . . . ?
N11_1 C12_1 C13_1 C14_1 1.0(2) . . . . ?
N11_1 C12_1 C13_1 C17_1 -179.65(13) . . . . ?
C12_1 C13_1 C14_1 C15_1 -0.5(2) . . . . ?
C17_1 C13_1 C14_1 C15_1 -179.88(13) . . . . ?
C13_1 C14_1 C15_1 C16_1 -0.2(2) . . . . ?
C12_1 N11_1 C16_1 C15_1 -0.3(2) . . . . ?
C14_1 C15_1 C16_1 N11_1 0.7(2) . . . . ?
C14_1 C13_1 C17_1 O17_1 -175.61(14) . . . . ?
C12_1 C13_1 C17_1 O17_1 5.0(2) . . . . ?
C14_1 C13_1 C17_1 N17_1 5.6(2) . . . . ?
C12_1 C13_1 C17_1 N17_1 -173.72(13) . . . . ?
O17_1 C17_1 N17_1 N27_1 1.5(2) . . . . ?
C13_1 C17_1 N17_1 N27_1 -179.73(11) . . . . ?
C26_1 N21_1 C22_1 C23_1 0.4(2) . . . . ?
N21_1 C22_1 C23_1 C24_1 -0.1(2) . . . . ?
C22_1 C23_1 C24_1 C25_1 -0.2(2) . . . . ?
C22_1 C23_1 C24_1 C27_1 -179.81(13) . . . . ?
C23_1 C24_1 C25_1 C26_1 0.2(2) . . . . ?
C27_1 C24_1 C25_1 C26_1 179.82(13) . . . . ?
C22_1 N21_1 C26_1 C25_1 -0.3(2) . . . . ?
C24_1 C25_1 C26_1 N21_1 0.0(2) . . . . ?
C23_1 C24_1 C27_1 N27_1 174.80(13) . . . . ?
C25_1 C24_1 C27_1 N27_1 -4.8(2) . . . . ?
C24_1 C27_1 N27_1 N17_1 -179.34(12) . . . . ?
C17_1 N17_1 N27_1 C27_1 -176.24(12) . . . . ?
O32_1 C31_1 C32_1 C33_1 -5.8(2) . . . . ?
O31_1 C31_1 C32_1 C33_1 174.90(13) . . . . ?
C31_1 C32_1 C33_1 C34_1 174.08(13) . . . . ?
C32_1 C33_1 C34_1 C35_1 178.80(13) . . . . ?
C33_1 C34_1 C35_1 O36_1 -9.5(2) . . . . ?
C33_1 C34_1 C35_1 O35_1 172.23(12) . . . . ?
C16_2 N11_2 C12_2 C13_2 1.1(2) . . . . ?
N11_2 C12_2 C13_2 C14_2 -2.0(2) . . . . ?
N11_2 C12_2 C13_2 C17_2 175.96(13) . . . . ?
C12_2 C13_2 C14_2 C15_2 1.2(2) . . . . ?
C17_2 C13_2 C14_2 C15_2 -176.54(13) . . . . ?
C13_2 C14_2 C15_2 C16_2 0.3(2) . . . . ?
C12_2 N11_2 C16_2 C15_2 0.5(2) . . . . ?
C14_2 C15_2 C16_2 N11_2 -1.2(2) . . . . ?
C14_2 C13_2 C17_2 O17_2 171.69(14) . . . . ?
C12_2 C13_2 C17_2 O17_2 -6.1(2) . . . . ?
C14_2 C13_2 C17_2 N17_2 -7.2(2) . . . . ?
C12_2 C13_2 C17_2 N17_2 175.00(12) . . . . ?
O17_2 C17_2 N17_2 N27_2 -3.1(2) . . . . ?
C13_2 C17_2 N17_2 N27_2 175.81(11) . . . . ?
C26_2 N21_2 C22_2 C23_2 -0.6(2) . . . . ?
N21_2 C22_2 C23_2 C24_2 -1.4(2) . . . . ?
C22_2 C23_2 C24_2 C25_2 2.1(2) . . . . ?
C22_2 C23_2 C24_2 C27_2 -177.36(13) . . . . ?
C23_2 C24_2 C25_2 C26_2 -1.0(2) . . . . ?
C27_2 C24_2 C25_2 C26_2 178.48(13) . . . . ?
C22_2 N21_2 C26_2 C25_2 1.8(2) . . . . ?
C24_2 C25_2 C26_2 N21_2 -1.1(2) . . . . ?
C23_2 C24_2 C27_2 N27_2 -178.79(13) . . . . ?
C25_2 C24_2 C27_2 N27_2 1.7(2) . . . . ?
C24_2 C27_2 N27_2 N17_2 -178.88(12) . . . . ?
C17_2 N17_2 N27_2 C27_2 177.94(12) . . . . ?
O32_2 C31_2 C32_2 C33_2 14.6(2) . . . . ?
O31_2 C31_2 C32_2 C33_2 -166.76(13) . . . . ?
C31_2 C32_2 C33_2 C34_2 178.34(13) . . . . ?
C32_2 C33_2 C34_2 C35_2 177.14(12) . . . . ?
C33_2 C34_2 C35_2 O36_2 -7.2(2) . . . . ?
C33_2 C34_2 C35_2 O35_2 173.07(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N17_1 H17_1 O2W_1 0.845(17) 2.012(16) 2.8200(16) 159.6(16) .
N17_2 H17_2 O4W_2 0.918(16) 1.949(17) 2.8413(16) 163.8(15) .
O31_1 H31_1 N11_1 0.951(19) 1.72(2) 2.6696(16) 173.9(18) .
O31_2 H31_2 N11_2 0.935(19) 1.74(2) 2.6636(16) 168.6(18) .
O35_1 H35_1 N21_1 1.042(19) 1.588(19) 2.6273(15) 175.1(16) 1_354
O35_2 H35_2 N21_2 1.03(2) 1.63(2) 2.6474(15) 168.6(17) 1_354
O1W_1 H1A_1 O17_1 0.82(2) 1.95(2) 2.7730(16) 175(2) .
O3W_2 H3A_2 O17_2 0.80(2) 2.01(2) 2.8099(15) 174(2) .
O1W_1 H1B_1 O17_2 0.78(2) 2.31(2) 2.9507(15) 140.2(19) 2_566
O3W_2 H3B_2 O17_1 0.83(2) 2.22(2) 2.9364(15) 144.8(18) 2_566
O2W_1 H2A_1 O3W_2 0.85(2) 1.99(2) 2.8091(17) 164.2(18) .
O4W_2 H4A_2 O1W_1 0.89(2) 1.89(2) 2.7575(17) 163.8(18) 1_645
O2W_1 H2B_1 O36_2 0.89(2) 1.93(2) 2.7944(16) 162.6(17) 2_455
O4W_2 H4B_2 O36_1 0.91(2) 1.88(2) 2.7851(16) 171.0(17) 2_455

_diffrn_measured_fraction_theta_max 0.879
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.073
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_42Sub2H2O
_database_code_depnum_ccdc_archive 'CCDC 1478930'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-D-Sub [(4-pyridyl)-CONH-N=CH-(2-pyridyl)]2, HOOC-(CH2)6-COOH dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O)2 (C8 H14 O4) (H2 O)2
;
_chemical_formula_sum            'C32 H38 N8 O8'
_chemical_formula_weight         662.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.6774(11)
_cell_length_b                   8.2196(14)
_cell_length_c                   15.972(3)
_cell_angle_alpha                81.888(7)
_cell_angle_beta                 83.771(8)
_cell_angle_gamma                74.805(7)
_cell_volume                     835.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6260
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      68.59

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             350
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7829
_exptl_absorpt_correction_T_max  0.8821
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            13228
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         68.58
_reflns_number_total             2996
_reflns_number_gt                2754
_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)+(0.0500P)²+0.4000P] 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         2996
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O1W O 0.02069(17) 0.85728(15) 0.39227(7) 0.0290(3) Uani 1 1 d . . .
H1A H -0.090(3) 0.838(3) 0.4190(13) 0.035 Uiso 1 1 d . . .
H1B H 0.044(3) 0.807(3) 0.3450(14) 0.035 Uiso 1 1 d . . .
N11 N 0.22309(19) 0.48068(16) 0.69738(8) 0.0232(3) Uani 1 1 d . . .
C12 C 0.1085(2) 0.60540(19) 0.64576(9) 0.0246(3) Uani 1 1 d . . .
H12 H -0.0388 0.6284 0.6541 0.030 Uiso 1 1 calc R . .
C13 C 0.1962(2) 0.70287(19) 0.58039(9) 0.0225(3) Uani 1 1 d . . .
H13 H 0.1105 0.7910 0.5454 0.027 Uiso 1 1 calc R . .
C14 C 0.4136(2) 0.66771(17) 0.56760(9) 0.0184(3) Uani 1 1 d . . .
C15 C 0.5327(2) 0.53733(17) 0.62118(9) 0.0199(3) Uani 1 1 d . . .
H15 H 0.6804 0.5105 0.6141 0.024 Uiso 1 1 calc R . .
C16 C 0.4322(2) 0.44731(18) 0.68508(9) 0.0222(3) Uani 1 1 d . . .
H16 H 0.5139 0.3591 0.7214 0.027 Uiso 1 1 calc R . .
C17 C 0.5300(2) 0.76465(17) 0.50028(9) 0.0182(3) Uani 1 1 d . . .
N17 N 0.41614(19) 0.86044(15) 0.43708(8) 0.0196(3) Uani 1 1 d . . .
H17 H 0.289(3) 0.859(2) 0.4318(11) 0.023 Uiso 1 1 d . . .
O17 O 0.71681(15) 0.75302(13) 0.50490(7) 0.0247(3) Uani 1 1 d . . .
N21 N 0.3476(2) 1.24841(16) 0.19427(8) 0.0261(3) Uani 1 1 d . . .
C22 C 0.4892(2) 1.14533(18) 0.24575(9) 0.0215(3) Uani 1 1 d . . .
C23 C 0.7017(2) 1.14204(18) 0.23651(9) 0.0233(3) Uani 1 1 d . . .
H23 H 0.7964 1.0659 0.2731 0.028 Uiso 1 1 calc R . .
C24 C 0.7709(3) 1.25289(19) 0.17247(10) 0.0267(3) Uani 1 1 d . . .
H24 H 0.9135 1.2545 0.1647 0.032 Uiso 1 1 calc R . .
C25 C 0.6259(3) 1.3615(2) 0.12000(10) 0.0305(4) Uani 1 1 d . . .
H25 H 0.6679 1.4392 0.0761 0.037 Uiso 1 1 calc R . .
C26 C 0.4195(3) 1.3541(2) 0.13292(10) 0.0302(4) Uani 1 1 d . . .
H26 H 0.3228 1.4279 0.0964 0.036 Uiso 1 1 calc R . .
C27 C 0.4012(2) 1.03849(18) 0.31479(9) 0.0214(3) Uani 1 1 d . . .
H27 H 0.2603 1.0338 0.3155 0.026 Uiso 1 1 calc R . .
N27 N 0.51501(18) 0.95181(14) 0.37395(7) 0.0199(3) Uani 1 1 d . . .
C31 C -0.0614(2) 0.25487(18) 0.83141(9) 0.0209(3) Uani 1 1 d . . .
O31 O 0.08550(18) 0.33039(15) 0.83915(7) 0.0315(3) Uani 1 1 d . . .
H31 H 0.129(3) 0.377(3) 0.7860(14) 0.038 Uiso 1 1 d . . .
O32 O -0.13701(16) 0.25960(15) 0.76420(7) 0.0297(3) Uani 1 1 d . . .
C32 C -0.1260(2) 0.15760(19) 0.91303(9) 0.0225(3) Uani 1 1 d . . .
H32A H -0.1178 0.2194 0.9609 0.027 Uiso 1 1 calc R . .
H32B H -0.0252 0.0453 0.9207 0.027 Uiso 1 1 calc R . .
C33 C -0.3453(2) 0.13051(19) 0.91702(9) 0.0238(3) Uani 1 1 d . . .
H33A H -0.3619 0.0843 0.8649 0.029 Uiso 1 1 calc R . .
H33B H -0.4488 0.2411 0.9192 0.029 Uiso 1 1 calc R . .
C34 C -0.3875(2) 0.00799(18) 0.99496(9) 0.0217(3) Uani 1 1 d . . .
H34A H -0.2924 -0.1055 0.9899 0.026 Uiso 1 1 calc R . .
H34B H -0.3569 0.0486 1.0465 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
O1W H1A 0.85(2) . ?
O1W H1B 0.89(2) . ?
N11 C12 1.343(2) . ?
N11 C16 1.348(2) . ?
C12 C13 1.397(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(2) . ?
C14 C17 1.5158(18) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2350(18) . ?
C17 N17 1.3586(19) . ?
N17 N27 1.3850(16) . ?
N17 H17 0.865(19) . ?
N21 C26 1.349(2) . ?
N21 C22 1.3565(19) . ?
C22 C23 1.404(2) . ?
C22 C27 1.4797(19) . ?
C23 C24 1.395(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.2886(19) . ?
C27 H27 0.9500 . ?
C31 O32 1.2263(18) . ?
C31 O31 1.3155(18) . ?
C31 C32 1.5129(19) . ?
O31 H31 0.93(2) . ?
C32 C33 1.531(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5370(19) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C34 1.532(3) 2_457 ?
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
H1A O1W H1B 108.3(18) . . ?
C12 N11 C16 118.45(12) . . ?
N11 C12 C13 122.96(13) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 118.50(13) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 118.48(13) . . ?
C15 C14 C17 117.21(12) . . ?
C13 C14 C17 124.29(12) . . ?
C16 C15 C14 119.16(13) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N11 C16 C15 122.45(13) . . ?
N11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
O17 C17 N17 124.19(13) . . ?
O17 C17 C14 120.10(12) . . ?
N17 C17 C14 115.71(12) . . ?
C17 N17 N27 118.07(12) . . ?
C17 N17 H17 123.0(12) . . ?
N27 N17 H17 118.6(12) . . ?
C26 N21 C22 116.59(13) . . ?
N21 C22 C23 123.35(13) . . ?
N21 C22 C27 114.57(13) . . ?
C23 C22 C27 122.06(13) . . ?
C24 C23 C22 118.61(14) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 118.49(15) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C26 C25 C24 118.95(14) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 123.99(15) . . ?
N21 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
N27 C27 C22 120.16(13) . . ?
N27 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C27 N27 N17 115.69(12) . . ?
O32 C31 O31 123.49(13) . . ?
O32 C31 C32 122.79(13) . . ?
O31 C31 C32 113.71(12) . . ?
C31 O31 H31 109.6(13) . . ?
C31 C32 C33 114.64(12) . . ?
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 C34 111.73(12) . . ?
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 . . ?
C34 C34 C33 112.71(15) 2_457 . ?
C34 C34 H34A 109.0 2_457 . ?
C33 C34 H34A 109.0 . . ?
C34 C34 H34B 109.0 2_457 . ?
C33 C34 H34B 109.0 . . ?
H34A C34 H34B 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 -0.5(2) . . . . ?
N11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C12 C13 C14 C17 -178.94(13) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C17 C14 C15 C16 178.66(12) . . . . ?
C12 N11 C16 C15 0.1(2) . . . . ?
C14 C15 C16 N11 0.2(2) . . . . ?
C15 C14 C17 O17 -15.07(19) . . . . ?
C13 C14 C17 O17 163.51(14) . . . . ?
C15 C14 C17 N17 164.65(12) . . . . ?
C13 C14 C17 N17 -16.8(2) . . . . ?
O17 C17 N17 N27 -0.4(2) . . . . ?
C14 C17 N17 N27 179.92(11) . . . . ?
C26 N21 C22 C23 -1.5(2) . . . . ?
C26 N21 C22 C27 176.89(13) . . . . ?
N21 C22 C23 C24 1.5(2) . . . . ?
C27 C22 C23 C24 -176.73(13) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 -0.6(2) . . . . ?
C22 N21 C26 C25 0.4(2) . . . . ?
C24 C25 C26 N21 0.6(3) . . . . ?
N21 C22 C27 N27 -171.12(13) . . . . ?
C23 C22 C27 N27 7.3(2) . . . . ?
C22 C27 N27 N17 177.93(12) . . . . ?
C17 N17 N27 C27 178.95(13) . . . . ?
O32 C31 C32 C33 -24.9(2) . . . . ?
O31 C31 C32 C33 156.40(13) . . . . ?
C31 C32 C33 C34 171.07(12) . . . . ?
C32 C33 C34 C34 174.50(15) . . . 2_457 ?

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
N17 H17 O1W 0.865(19) 1.97(2) 2.8173(17) 167.1(17) .
O31 H31 N11 0.93(2) 1.69(2) 2.6176(16) 171(2) .
O1W H1A O17 0.85(2) 1.96(2) 2.7879(15) 162.6(19) 1_455
O1W H1B O32 0.89(2) 1.89(2) 2.7636(17) 165.2(18) 2_566

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_34SucH2O
_database_code_depnum_ccdc_archive 'CCDC 1478925'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-B-Suc 3-pyridyl-CONH-N=CH-(3-pyridyl), HOOC-(CH2)2-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C4 H6 O4) (H2 O)
;
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.1160(8)
_cell_length_b                   13.0840(16)
_cell_length_c                   36.062(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3357.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6095
_cell_measurement_theta_min      4.91
_cell_measurement_theta_max      68.76

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7519
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            29624
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         70.19
_reflns_number_total             3060
_reflns_number_gt                2439
_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)+(0.0600P)²+3.0000P] 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         3060
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
O1W O 0.1350(3) 0.54573(16) 0.36353(6) 0.0434(5) Uani 1 1 d . . .
H1A H 0.135(5) 0.601(3) 0.3510(9) 0.052 Uiso 1 1 d . . .
H1B H 0.061(5) 0.549(3) 0.3824(9) 0.052 Uiso 1 1 d . . .
N11 N 0.3551(3) 0.41087(18) 0.22117(6) 0.0373(5) Uani 1 1 d . . .
C12 C 0.3364(3) 0.3485(2) 0.25074(8) 0.0356(6) Uani 1 1 d . . .
H12 H 0.3085 0.2785 0.2465 0.043 Uiso 1 1 calc R . .
C13 C 0.3563(3) 0.3821(2) 0.28720(8) 0.0341(6) Uani 1 1 d . . .
C14 C 0.4007(3) 0.4852(2) 0.29295(8) 0.0367(6) Uani 1 1 d . . .
H14 H 0.4160 0.5108 0.3174 0.044 Uiso 1 1 calc R . .
C15 C 0.4222(3) 0.5496(2) 0.26258(8) 0.0377(6) Uani 1 1 d . . .
H15 H 0.4525 0.6197 0.2660 0.045 Uiso 1 1 calc R . .
C16 C 0.3986(3) 0.5100(2) 0.22727(8) 0.0365(6) Uani 1 1 d . . .
H16 H 0.4136 0.5542 0.2066 0.044 Uiso 1 1 calc R . .
C17 C 0.3374(3) 0.3051(2) 0.31805(8) 0.0361(6) Uani 1 1 d . . .
N17 N 0.2754(3) 0.34573(19) 0.35088(6) 0.0364(5) Uani 1 1 d . . .
H17 H 0.238(4) 0.407(3) 0.3523(8) 0.044 Uiso 1 1 d . . .
O17 O 0.3756(3) 0.21405(15) 0.31392(5) 0.0421(5) Uani 1 1 d . . .
N21 N 0.1508(3) 0.16335(19) 0.51346(7) 0.0419(6) Uani 1 1 d . . .
C22 C 0.1826(4) 0.1133(2) 0.48139(8) 0.0432(7) Uani 1 1 d . . .
H22 H 0.1934 0.0410 0.4820 0.052 Uiso 1 1 calc R . .
C23 C 0.2005(4) 0.1625(2) 0.44743(8) 0.0407(7) Uani 1 1 d . . .
H23 H 0.2266 0.1245 0.4256 0.049 Uiso 1 1 calc R . .
C24 C 0.1796(3) 0.2687(2) 0.44582(8) 0.0362(6) Uani 1 1 d . . .
C25 C 0.1390(4) 0.3198(2) 0.47895(8) 0.0386(6) Uani 1 1 d . . .
H25 H 0.1186 0.3916 0.4790 0.046 Uiso 1 1 calc R . .
C26 C 0.1290(4) 0.2646(2) 0.51191(8) 0.0399(7) Uani 1 1 d . . .
H26 H 0.1055 0.3006 0.5343 0.048 Uiso 1 1 calc R . .
C27 C 0.2003(3) 0.3273(2) 0.41125(8) 0.0366(6) Uani 1 1 d . . .
H27 H 0.1696 0.3980 0.4109 0.044 Uiso 1 1 calc R . .
N27 N 0.2599(3) 0.28361(17) 0.38149(6) 0.0367(5) Uani 1 1 d . . .
C31 C 0.3175(4) 0.2409(2) 0.15400(8) 0.0382(6) Uani 1 1 d . . .
O32 O 0.3731(3) 0.19371(16) 0.18113(6) 0.0518(6) Uani 1 1 d . . .
O31 O 0.2890(3) 0.34055(15) 0.15374(6) 0.0424(5) Uani 1 1 d . . .
H31 H 0.316(4) 0.372(3) 0.1815(9) 0.051 Uiso 1 1 d . . .
C32 C 0.2743(4) 0.1886(2) 0.11741(8) 0.0372(6) Uani 1 1 d . . .
H32A H 0.3360 0.2263 0.0970 0.045 Uiso 1 1 calc R . .
H32B H 0.1370 0.1898 0.1130 0.045 Uiso 1 1 calc R . .
C33 C 0.3435(4) 0.0777(2) 0.11757(8) 0.0407(7) Uani 1 1 d . . .
H33A H 0.4825 0.0779 0.1186 0.049 Uiso 1 1 calc R . .
H33B H 0.2974 0.0440 0.1404 0.049 Uiso 1 1 calc R . .
C34 C 0.2825(4) 0.0153(2) 0.08463(8) 0.0393(7) Uani 1 1 d . . .
O34 O 0.4148(3) -0.04718(16) 0.07232(6) 0.0445(5) Uani 1 1 d . . .
H34 H 0.377(5) -0.087(3) 0.0517(9) 0.053 Uiso 1 1 d . . .
O35 O 0.1230(3) 0.02076(16) 0.07146(6) 0.0464(5) Uani 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
O1W H1A 0.85(4) . ?
O1W H1B 0.86(3) . ?
N11 C12 1.350(4) . ?
N11 C16 1.352(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(4) . ?
C13 C17 1.507(4) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.231(3) . ?
C17 N17 1.371(4) . ?
N17 N27 1.375(3) . ?
N17 H17 0.85(3) . ?
N21 C26 1.335(4) . ?
N21 C22 1.348(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(4) . ?
C24 C27 1.471(4) . ?
C25 C26 1.393(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.288(3) . ?
C27 H27 0.9500 . ?
C31 O32 1.223(3) . ?
C31 O31 1.319(3) . ?
C31 C32 1.518(4) . ?
O31 H31 1.10(3) . ?
C32 C33 1.532(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.506(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O35 1.233(3) . ?
C34 O34 1.323(3) . ?
O34 H34 0.95(3) . ?

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
H1A O1W H1B 112(3) . . ?
C12 N11 C16 118.3(2) . . ?
N11 C12 C13 123.0(3) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 117.8(3) . . ?
C12 C13 C17 118.4(2) . . ?
C14 C13 C17 123.7(2) . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N11 C16 C15 122.5(3) . . ?
N11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
O17 C17 N17 123.4(3) . . ?
O17 C17 C13 122.6(2) . . ?
N17 C17 C13 114.0(2) . . ?
C17 N17 N27 119.3(2) . . ?
C17 N17 H17 121(2) . . ?
N27 N17 H17 119(2) . . ?
C26 N21 C22 117.7(3) . . ?
N21 C22 C23 123.1(3) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C25 117.5(3) . . ?
C23 C24 C27 122.9(3) . . ?
C25 C24 C27 119.6(3) . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N21 C26 C25 123.0(3) . . ?
N21 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
N27 C27 C24 120.5(2) . . ?
N27 C27 H27 119.8 . . ?
C24 C27 H27 119.8 . . ?
C27 N27 N17 115.6(2) . . ?
O32 C31 O31 123.7(3) . . ?
O32 C31 C32 122.2(3) . . ?
O31 C31 C32 114.1(2) . . ?
C31 O31 H31 109.7(17) . . ?
C31 C32 C33 111.0(2) . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 C32 114.7(2) . . ?
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 . . ?
O35 C34 O34 124.2(3) . . ?
O35 C34 C33 122.5(2) . . ?
O34 C34 C33 113.2(2) . . ?
C34 O34 H34 114(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 1.3(3) . . . . ?
N11 C12 C13 C14 -1.1(4) . . . . ?
N11 C12 C13 C17 -178.4(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C17 C13 C14 C15 177.5(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C12 N11 C16 C15 -0.8(4) . . . . ?
C14 C15 C16 N11 0.1(4) . . . . ?
C12 C13 C17 O17 28.2(3) . . . . ?
C14 C13 C17 O17 -149.0(3) . . . . ?
C12 C13 C17 N17 -152.3(2) . . . . ?
C14 C13 C17 N17 30.6(3) . . . . ?
O17 C17 N17 N27 2.2(4) . . . . ?
C13 C17 N17 N27 -177.4(2) . . . . ?
C26 N21 C22 C23 2.5(4) . . . . ?
N21 C22 C23 C24 -1.9(4) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C22 C23 C24 C27 178.6(2) . . . . ?
C23 C24 C25 C26 2.6(4) . . . . ?
C27 C24 C25 C26 -176.8(2) . . . . ?
C22 N21 C26 C25 -0.5(4) . . . . ?
C24 C25 C26 N21 -2.1(4) . . . . ?
C23 C24 C27 N27 -7.8(4) . . . . ?
C25 C24 C27 N27 171.5(2) . . . . ?
C24 C27 N27 N17 -179.5(2) . . . . ?
C17 N17 N27 C27 -179.9(2) . . . . ?
O32 C31 C32 C33 -10.5(4) . . . . ?
O31 C31 C32 C33 169.8(2) . . . . ?
C31 C32 C33 C34 171.6(2) . . . . ?
C32 C33 C34 O35 -41.0(4) . . . . ?
C32 C33 C34 O34 140.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N17 H17 O1W 0.85(3) 1.99(3) 2.838(3) 171(3) .
O31 H31 N11 1.10(3) 1.54(3) 2.642(3) 177(3) .
O34 H34 N21 0.95(3) 1.71(3) 2.652(3) 170(3) 2_554
O1W H1A O17 0.85(4) 2.00(4) 2.838(3) 170(3) 8_665
O1W H1B O35 0.86(3) 2.15(3) 2.996(3) 167(3) 3

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.069
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_42Adp2H2O
_database_code_depnum_ccdc_archive 'CCDC 1478932'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-D-Adp [(4-pyridyl)-CONH-N=CH-(2-pyridyl)]2, HOOC-(CH2)4-COOH dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O)2 (C6 H10 O4) (H2 O)2
;
_chemical_formula_sum            'C30 H34 N8 O8'
_chemical_formula_weight         634.65

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                   6.5986(6)
_cell_length_b                   8.0173(8)
_cell_length_c                   15.3396(14)
_cell_angle_alpha                97.862(4)
_cell_angle_beta                 101.861(3)
_cell_angle_gamma                104.541(3)
_cell_volume                     753.39(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8837
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      33.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_T_max  0.9897
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18394
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         33.17
_reflns_number_total             5103
_reflns_number_gt                4166
_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)+(0.0800P)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         5103
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1W O 0.93923(11) 0.13694(11) 0.38641(5) 0.02556(17) Uani 1 1 d . . .
H1A H 0.844(2) 0.1615(19) 0.4142(10) 0.031 Uiso 1 1 d . . .
H1B H 0.911(2) 0.1660(19) 0.3348(11) 0.031 Uiso 1 1 d . . .
N11 N 0.38911(13) 0.56620(11) 0.71395(6) 0.01949(17) Uani 1 1 d . . .
C12 C 0.58841(15) 0.59497(12) 0.70082(6) 0.01835(18) Uani 1 1 d . . .
H12 H 0.7016 0.6897 0.7401 0.022 Uiso 1 1 calc R . .
C13 C 0.63551(14) 0.49186(12) 0.63229(6) 0.01665(17) Uani 1 1 d . . .
H13 H 0.7784 0.5165 0.6244 0.020 Uiso 1 1 calc R . .
C14 C 0.47234(13) 0.35245(11) 0.57525(6) 0.01468(16) Uani 1 1 d . . .
C15 C 0.26489(14) 0.32170(13) 0.58893(7) 0.01903(18) Uani 1 1 d . . .
H15 H 0.1490 0.2270 0.5512 0.023 Uiso 1 1 calc R . .
C16 C 0.23122(15) 0.43236(13) 0.65882(7) 0.02098(19) Uani 1 1 d . . .
H16 H 0.0895 0.4120 0.6678 0.025 Uiso 1 1 calc R . .
C17 C 0.53370(13) 0.24287(11) 0.50348(6) 0.01490(17) Uani 1 1 d . . .
N17 N 0.36812(12) 0.13247(10) 0.43735(5) 0.01606(16) Uani 1 1 d . . .
H17 H 0.231(2) 0.1387(17) 0.4298(9) 0.019 Uiso 1 1 d . . .
O17 O 0.72473(10) 0.25603(9) 0.50720(5) 0.02093(16) Uani 1 1 d . . .
N21 N 0.10710(13) -0.30734(11) 0.18275(6) 0.02021(17) Uani 1 1 d . . .
C22 C 0.28822(14) -0.18834(12) 0.23458(6) 0.01650(17) Uani 1 1 d . . .
C23 C 0.49347(15) -0.17944(12) 0.22141(7) 0.01931(18) Uani 1 1 d . . .
H23 H 0.6174 -0.0920 0.2592 0.023 Uiso 1 1 calc R . .
C24 C 0.51338(16) -0.30007(13) 0.15246(7) 0.02219(19) Uani 1 1 d . . .
H24 H 0.6509 -0.2971 0.1418 0.027 Uiso 1 1 calc R . .
C25 C 0.32781(17) -0.42537(13) 0.09926(7) 0.0235(2) Uani 1 1 d . . .
H25 H 0.3357 -0.5108 0.0516 0.028 Uiso 1 1 calc R . .
C26 C 0.13043(16) -0.42364(13) 0.11690(7) 0.0225(2) Uani 1 1 d . . .
H26 H 0.0043 -0.5101 0.0801 0.027 Uiso 1 1 calc R . .
C27 C 0.25489(15) -0.07005(12) 0.30836(6) 0.01818(18) Uani 1 1 d . . .
H27 H 0.1126 -0.0684 0.3106 0.022 Uiso 1 1 calc R . .
N27 N 0.41702(12) 0.03078(10) 0.36967(5) 0.01656(16) Uani 1 1 d . . .
C31 C 0.21609(14) 0.81888(12) 0.86106(7) 0.01801(18) Uani 1 1 d . . .
O31 O 0.36985(12) 0.74190(11) 0.86603(5) 0.02722(18) Uani 1 1 d . . .
H31 H 0.361(2) 0.680(2) 0.8059(11) 0.033 Uiso 1 1 d . . .
O32 O 0.08965(11) 0.81521(11) 0.79030(5) 0.02525(17) Uani 1 1 d . . .
C32 C 0.21064(14) 0.91459(13) 0.95148(6) 0.01920(18) Uani 1 1 d . . .
H32A H 0.3272 1.0273 0.9687 0.023 Uiso 1 1 calc R . .
H32B H 0.2416 0.8435 0.9978 0.023 Uiso 1 1 calc R . .
C33 C -0.00258(14) 0.95251(13) 0.95327(6) 0.01946(18) Uani 1 1 d . . .
H33A H -0.1203 0.8405 0.9361 0.023 Uiso 1 1 calc R . .
H33B H -0.0336 1.0257 0.9081 0.023 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
O1W H1A 0.873(15) . ?
O1W H1B 0.853(16) . ?
N11 C16 1.3342(12) . ?
N11 C12 1.3389(12) . ?
C12 C13 1.3823(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3838(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.3933(12) . ?
C14 C17 1.4983(12) . ?
C15 C16 1.3866(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2269(10) . ?
C17 N17 1.3489(11) . ?
N17 N27 1.3729(10) . ?
N17 H17 0.905(13) . ?
N21 C26 1.3385(12) . ?
N21 C22 1.3417(11) . ?
C22 C23 1.3958(13) . ?
C22 C27 1.4636(12) . ?
C23 C24 1.3829(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.3862(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.3867(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.2754(12) . ?
C27 H27 0.9500 . ?
C31 O32 1.2172(12) . ?
C31 O31 1.3083(11) . ?
C31 C32 1.5023(13) . ?
O31 H31 0.970(16) . ?
C32 C33 1.5170(12) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.5180(18) 2_577 ?
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
H1A O1W H1B 106.3(14) . . ?
C16 N11 C12 118.42(8) . . ?
N11 C12 C13 122.42(8) . . ?
N11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 119.31(8) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 118.43(8) . . ?
C13 C14 C17 116.99(7) . . ?
C15 C14 C17 124.57(8) . . ?
C16 C15 C14 118.55(8) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 122.87(8) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O17 C17 N17 123.87(8) . . ?
O17 C17 C14 120.23(8) . . ?
N17 C17 C14 115.90(7) . . ?
C17 N17 N27 117.87(7) . . ?
C17 N17 H17 122.4(8) . . ?
N27 N17 H17 118.6(8) . . ?
C26 N21 C22 116.80(8) . . ?
N21 C22 C23 123.26(8) . . ?
N21 C22 C27 114.58(8) . . ?
C23 C22 C27 122.13(8) . . ?
C24 C23 C22 118.89(9) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 118.41(9) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C26 118.74(9) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
N21 C26 C25 123.88(9) . . ?
N21 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
N27 C27 C22 119.96(8) . . ?
N27 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C27 N27 N17 115.40(7) . . ?
O32 C31 O31 123.75(9) . . ?
O32 C31 C32 122.71(8) . . ?
O31 C31 C32 113.54(8) . . ?
C31 O31 H31 109.2(9) . . ?
C31 C32 C33 114.27(8) . . ?
C31 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 C33 111.43(9) . 2_577 ?
C32 C33 H33A 109.3 . . ?
C33 C33 H33A 109.3 2_577 . ?
C32 C33 H33B 109.3 . . ?
C33 C33 H33B 109.3 2_577 . ?
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 0.30(15) . . . . ?
N11 C12 C13 C14 -0.59(15) . . . . ?
C12 C13 C14 C15 0.33(14) . . . . ?
C12 C13 C14 C17 -178.71(8) . . . . ?
C13 C14 C15 C16 0.19(14) . . . . ?
C17 C14 C15 C16 179.15(8) . . . . ?
C12 N11 C16 C15 0.26(15) . . . . ?
C14 C15 C16 N11 -0.51(16) . . . . ?
C13 C14 C17 O17 13.69(13) . . . . ?
C15 C14 C17 O17 -165.28(9) . . . . ?
C13 C14 C17 N17 -166.58(8) . . . . ?
C15 C14 C17 N17 14.45(13) . . . . ?
O17 C17 N17 N27 -0.92(14) . . . . ?
C14 C17 N17 N27 179.37(7) . . . . ?
C26 N21 C22 C23 1.38(14) . . . . ?
C26 N21 C22 C27 -177.07(8) . . . . ?
N21 C22 C23 C24 -0.88(15) . . . . ?
C27 C22 C23 C24 177.46(9) . . . . ?
C22 C23 C24 C25 -0.11(15) . . . . ?
C23 C24 C25 C26 0.50(15) . . . . ?
C22 N21 C26 C25 -0.96(15) . . . . ?
C24 C25 C26 N21 0.04(16) . . . . ?
N21 C22 C27 N27 169.78(9) . . . . ?
C23 C22 C27 N27 -8.69(15) . . . . ?
C22 C27 N27 N17 -178.02(8) . . . . ?
C17 N17 N27 C27 -179.35(8) . . . . ?
O32 C31 C32 C33 19.59(14) . . . . ?
O31 C31 C32 C33 -160.89(9) . . . . ?
C31 C32 C33 C33 179.40(10) . . . 2_577 ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23Azl
_database_code_depnum_ccdc_archive 'CCDC 1478926'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-A-Azl (2-pyridyl)-CONH-N=CH-(3-pyridyl), HOOC-(CH2)7-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C9 H16 O4)
;
_chemical_formula_sum            'C21 H26 N4 O5'
_chemical_formula_weight         414.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.5041(12)
_cell_length_b                   9.6723(14)
_cell_length_c                   14.013(2)
_cell_angle_alpha                80.742(6)
_cell_angle_beta                 81.368(6)
_cell_angle_gamma                68.770(5)
_cell_volume                     1055.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9105
_cell_measurement_theta_min      4.94
_cell_measurement_theta_max      68.22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7773
_exptl_absorpt_correction_T_max  0.8853
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            16331
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.94
_diffrn_reflns_theta_max         69.60
_reflns_number_total             3704
_reflns_number_gt                3399
_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)+(0.0450P)²+0.4000P] 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     SHELXL
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3704
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 1.40772(15) 0.27062(13) -0.09917(9) 0.0243(3) Uani 1 1 d . . .
C12 C 1.30124(17) 0.21073(15) -0.03974(10) 0.0221(3) Uani 1 1 d . . .
C13 C 1.29223(18) 0.07120(16) -0.04712(10) 0.0252(3) Uani 1 1 d . . .
H13 H 1.2139 0.0350 -0.0047 0.030 Uiso 1 1 calc R . .
C14 C 1.40057(19) -0.01368(16) -0.11800(11) 0.0266(3) Uani 1 1 d . . .
H14 H 1.3994 -0.1097 -0.1240 0.032 Uiso 1 1 calc R . .
C15 C 1.51094(18) 0.04610(16) -0.18004(11) 0.0273(3) Uani 1 1 d . . .
H15 H 1.5863 -0.0085 -0.2291 0.033 Uiso 1 1 calc R . .
C16 C 1.50786(18) 0.18793(16) -0.16822(10) 0.0259(3) Uani 1 1 d . . .
H16 H 1.5813 0.2285 -0.2118 0.031 Uiso 1 1 calc R . .
C17 C 1.18608(17) 0.30143(15) 0.03791(10) 0.0234(3) Uani 1 1 d . . .
N17 N 1.20422(15) 0.43458(13) 0.04183(9) 0.0240(3) Uani 1 1 d . . .
H17 H 1.275(2) 0.4630(19) 0.0012(13) 0.029 Uiso 1 1 d . . .
O17 O 1.08379(13) 0.25362(11) 0.09376(8) 0.0304(3) Uani 1 1 d . . .
N21 N 0.80745(15) 0.79166(13) 0.32526(8) 0.0247(3) Uani 1 1 d . . .
C22 C 0.90059(17) 0.70713(15) 0.25569(10) 0.0224(3) Uani 1 1 d . . .
H22 H 0.8820 0.6174 0.2511 0.027 Uiso 1 1 calc R . .
C23 C 1.02502(17) 0.74468(15) 0.18885(10) 0.0222(3) Uani 1 1 d . . .
C24 C 1.04748(19) 0.88013(16) 0.19546(11) 0.0266(3) Uani 1 1 d . . .
H24 H 1.1275 0.9113 0.1510 0.032 Uiso 1 1 calc R . .
C25 C 0.95115(19) 0.96813(17) 0.26793(11) 0.0289(3) Uani 1 1 d . . .
H25 H 0.9655 1.0593 0.2737 0.035 Uiso 1 1 calc R . .
C26 C 0.83311(18) 0.92021(16) 0.33196(11) 0.0273(3) Uani 1 1 d . . .
H26 H 0.7689 0.9796 0.3817 0.033 Uiso 1 1 calc R . .
C27 C 1.12665(18) 0.64706(16) 0.11452(10) 0.0249(3) Uani 1 1 d . . .
H27 H 1.2075 0.6753 0.0690 0.030 Uiso 1 1 calc R . .
N27 N 1.10392(15) 0.52230(13) 0.11228(8) 0.0240(3) Uani 1 1 d . . .
C31 C 0.41403(19) 0.76556(16) 0.44764(10) 0.0258(3) Uani 1 1 d . . .
O31 O 0.55717(14) 0.68272(12) 0.39990(8) 0.0313(3) Uani 1 1 d . . .
H31 H 0.634(2) 0.731(2) 0.3855(13) 0.038 Uiso 1 1 d . . .
O32 O 0.39578(16) 0.88570(14) 0.47230(11) 0.0505(4) Uani 1 1 d . . .
C32 C 0.28186(19) 0.69099(16) 0.46716(11) 0.0266(3) Uani 1 1 d . . .
H32A H 0.3366 0.5860 0.4944 0.032 Uiso 1 1 calc R . .
H32B H 0.2428 0.6895 0.4044 0.032 Uiso 1 1 calc R . .
C33 C 0.12620(18) 0.76361(16) 0.53643(11) 0.0262(3) Uani 1 1 d . . .
H33A H 0.1636 0.7726 0.5980 0.031 Uiso 1 1 calc R . .
H33B H 0.0633 0.8654 0.5070 0.031 Uiso 1 1 calc R . .
C34 C 0.00838(18) 0.67202(16) 0.55802(10) 0.0247(3) Uani 1 1 d . . .
H34A H 0.0732 0.5702 0.5866 0.030 Uiso 1 1 calc R . .
H34B H -0.0268 0.6628 0.4958 0.030 Uiso 1 1 calc R . .
C35 C -0.15182(19) 0.73659(16) 0.62720(11) 0.0275(3) Uani 1 1 d . . .
H35A H -0.1183 0.7452 0.6900 0.033 Uiso 1 1 calc R . .
H35B H -0.2187 0.8380 0.5990 0.033 Uiso 1 1 calc R . .
C36 C -0.26209(18) 0.63794(16) 0.64478(10) 0.0243(3) Uani 1 1 d . . .
H36A H -0.1916 0.5352 0.6686 0.029 Uiso 1 1 calc R . .
H36B H -0.2990 0.6339 0.5819 0.029 Uiso 1 1 calc R . .
C37 C -0.42037(18) 0.69012(15) 0.71775(10) 0.0237(3) Uani 1 1 d . . .
H37A H -0.3857 0.7006 0.7798 0.028 Uiso 1 1 calc R . .
H37B H -0.4968 0.7893 0.6920 0.028 Uiso 1 1 calc R . .
C38 C -0.51644(19) 0.57928(17) 0.73675(11) 0.0304(4) Uani 1 1 d . . .
H38A H -0.5573 0.5746 0.6752 0.036 Uiso 1 1 calc R . .
H38B H -0.4366 0.4787 0.7571 0.036 Uiso 1 1 calc R . .
C39 C -0.66634(19) 0.61875(15) 0.81361(11) 0.0264(3) Uani 1 1 d . . .
O39 O -0.80932(13) 0.61854(12) 0.78450(8) 0.0294(3) Uani 1 1 d . . .
H39 H -0.894(2) 0.648(2) 0.8298(13) 0.035 Uiso 1 1 d . . .
O40 O -0.65779(14) 0.64736(13) 0.89438(8) 0.0341(3) Uani 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 1.3452(18) . ?
N11 C12 1.3592(19) . ?
C12 C13 1.400(2) . ?
C12 C17 1.5092(19) . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2465(18) . ?
C17 N17 1.3618(19) . ?
N17 N27 1.3837(16) . ?
N17 H17 0.853(19) . ?
N21 C22 1.3423(18) . ?
N21 C26 1.3575(19) . ?
C22 C23 1.414(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.410(2) . ?
C23 C27 1.4761(19) . ?
C24 C25 1.397(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.2951(19) . ?
C27 H27 0.9500 . ?
C31 O32 1.2151(19) . ?
C31 O31 1.3390(17) . ?
C31 C32 1.513(2) . ?
O31 H31 0.91(2) . ?
C32 C33 1.5324(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.532(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5388(19) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.534(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5405(19) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.538(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.516(2) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 O40 1.2260(18) . ?
C39 O39 1.3401(19) . ?
O39 H39 0.879(19) . ?

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 116.26(12) . . ?
N11 C12 C13 123.74(13) . . ?
N11 C12 C17 117.54(12) . . ?
C13 C12 C17 118.72(13) . . ?
C14 C13 C12 118.71(14) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 118.42(13) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 118.57(13) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 124.26(14) . . ?
N11 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
O17 C17 N17 124.00(13) . . ?
O17 C17 C12 120.61(13) . . ?
N17 C17 C12 115.39(12) . . ?
C17 N17 N27 118.28(12) . . ?
C17 N17 H17 120.4(11) . . ?
N27 N17 H17 121.3(11) . . ?
C22 N21 C26 118.57(13) . . ?
N21 C22 C23 123.41(13) . . ?
N21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C24 C23 C22 117.29(13) . . ?
C24 C23 C27 121.11(13) . . ?
C22 C23 C27 121.59(13) . . ?
C25 C24 C23 119.43(14) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 119.10(14) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N21 C26 C25 122.17(13) . . ?
N21 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
N27 C27 C23 118.99(13) . . ?
N27 C27 H27 120.5 . . ?
C23 C27 H27 120.5 . . ?
C27 N27 N17 116.41(12) . . ?
O32 C31 O31 122.95(14) . . ?
O32 C31 C32 125.03(13) . . ?
O31 C31 C32 112.02(12) . . ?
C31 O31 H31 111.4(11) . . ?
C31 C32 C33 115.73(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 . . ?
C34 C33 C32 111.42(11) . . ?
C34 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 C35 115.11(12) . . ?
C33 C34 H34A 108.5 . . ?
C35 C34 H34A 108.5 . . ?
C33 C34 H34B 108.5 . . ?
C35 C34 H34B 108.5 . . ?
H34A C34 H34B 107.5 . . ?
C36 C35 C34 111.58(12) . . ?
C36 C35 H35A 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 C37 114.92(11) . . ?
C35 C36 H36A 108.5 . . ?
C37 C36 H36A 108.5 . . ?
C35 C36 H36B 108.5 . . ?
C37 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C38 C37 C36 111.55(11) . . ?
C38 C37 H37A 109.3 . . ?
C36 C37 H37A 109.3 . . ?
C38 C37 H37B 109.3 . . ?
C36 C37 H37B 109.3 . . ?
H37A C37 H37B 108.0 . . ?
C39 C38 C37 114.00(12) . . ?
C39 C38 H38A 108.8 . . ?
C37 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
C37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.6 . . ?
O40 C39 O39 123.30(13) . . ?
O40 C39 C38 123.54(14) . . ?
O39 C39 C38 113.15(12) . . ?
C39 O39 H39 109.7(12) . . ?

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 0.1(2) . . . . ?
C16 N11 C12 C17 -179.46(12) . . . . ?
N11 C12 C13 C14 1.4(2) . . . . ?
C17 C12 C13 C14 -179.04(12) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C12 N11 C16 C15 -1.6(2) . . . . ?
C14 C15 C16 N11 1.6(2) . . . . ?
N11 C12 C17 O17 178.93(12) . . . . ?
C13 C12 C17 O17 -0.7(2) . . . . ?
N11 C12 C17 N17 -1.55(18) . . . . ?
C13 C12 C17 N17 178.83(12) . . . . ?
O17 C17 N17 N27 0.4(2) . . . . ?
C12 C17 N17 N27 -179.15(11) . . . . ?
C26 N21 C22 C23 0.2(2) . . . . ?
N21 C22 C23 C24 -1.6(2) . . . . ?
N21 C22 C23 C27 178.94(12) . . . . ?
C22 C23 C24 C25 1.7(2) . . . . ?
C27 C23 C24 C25 -178.81(13) . . . . ?
C23 C24 C25 C26 -0.6(2) . . . . ?
C22 N21 C26 C25 1.0(2) . . . . ?
C24 C25 C26 N21 -0.9(2) . . . . ?
C24 C23 C27 N27 178.73(13) . . . . ?
C22 C23 C27 N27 -1.8(2) . . . . ?
C23 C27 N27 N17 -179.22(11) . . . . ?
C17 N17 N27 C27 179.05(12) . . . . ?
O32 C31 C32 C33 -9.7(2) . . . . ?
O31 C31 C32 C33 169.76(12) . . . . ?
C31 C32 C33 C34 -175.07(12) . . . . ?
C32 C33 C34 C35 179.99(12) . . . . ?
C33 C34 C35 C36 -179.96(12) . . . . ?
C34 C35 C36 C37 176.81(12) . . . . ?
C35 C36 C37 C38 -175.86(12) . . . . ?
C36 C37 C38 C39 175.74(12) . . . . ?
C37 C38 C39 O40 -50.8(2) . . . . ?
C37 C38 C39 O39 129.53(14) . . . . ?

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
N17 H17 O40 0.853(19) 2.318(19) 3.0879(17) 150.3(15) 1_754
O31 H31 N21 0.91(2) 1.82(2) 2.7085(16) 162.1(17) .
O39 H39 O17 0.879(19) 1.83(2) 2.6983(15) 167.6(17) 2_566

_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_33SebH2O
_database_code_depnum_ccdc_archive 'CCDC 1478931'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-C-Seb (3-pyridyl)-CONH-N=CH-(3-pyridyl), HOOCH-(CH2)8-COOH hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C10 H18 O4) (H2 O)
;
_chemical_formula_sum            'C22 H30 N4 O6'
_chemical_formula_weight         446.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.9504(10)
_cell_length_b                   14.170(2)
_cell_length_c                   23.788(3)
_cell_angle_alpha                79.555(9)
_cell_angle_beta                 84.610(8)
_cell_angle_gamma                89.821(9)
_cell_volume                     2293.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5645
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      58.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8097
_exptl_absorpt_correction_T_max  0.9115
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            36604
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         68.58
_reflns_number_total             8223
_reflns_number_gt                5569
_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)+(0.1000P)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         8223
_refine_ls_number_parameters     605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2466
_refine_ls_wR_factor_gt          0.2234
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_restrained_S_all      1.447
_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
O1W_1 O -0.6136(3) 0.35904(19) 0.57494(10) 0.0716(6) Uani 1 1 d . . .
H1A_1 H -0.713(6) 0.369(3) 0.5585(17) 0.086 Uiso 1 1 d . . .
H1B_1 H -0.648(5) 0.308(3) 0.6092(17) 0.086 Uiso 1 1 d . . .
N11_1 N -0.1747(4) 0.30807(17) 0.35552(10) 0.0616(6) Uani 1 1 d . . .
C12_1 C -0.0909(4) 0.3270(2) 0.40116(12) 0.0586(7) Uani 1 1 d . . .
H12A_1 H 0.0431 0.3147 0.4029 0.070 Uiso 1 1 calc R . .
C13_1 C -0.1907(4) 0.3640(2) 0.44639(12) 0.0566(7) Uani 1 1 d . . .
C14_1 C -0.3863(5) 0.3825(2) 0.44330(12) 0.0630(7) Uani 1 1 d . . .
H14A_1 H -0.4586 0.4080 0.4728 0.076 Uiso 1 1 calc R . .
C15_1 C -0.4761(5) 0.3630(2) 0.39615(13) 0.0661(8) Uani 1 1 d . . .
H15A_1 H -0.6097 0.3748 0.3933 0.079 Uiso 1 1 calc R . .
C16_1 C -0.3642(5) 0.3256(2) 0.35349(13) 0.0632(7) Uani 1 1 d . . .
H16A_1 H -0.4250 0.3121 0.3217 0.076 Uiso 1 1 calc R . .
C17_1 C -0.0770(5) 0.37972(19) 0.49512(12) 0.0573(7) Uani 1 1 d . . .
N17_1 N -0.1867(4) 0.38916(18) 0.54506(10) 0.0593(6) Uani 1 1 d . . .
H17_1 H -0.322(5) 0.379(2) 0.5508(14) 0.071 Uiso 1 1 d . . .
O17_1 O 0.1009(3) 0.38229(15) 0.49032(8) 0.0656(5) Uani 1 1 d . . .
N21_1 N -0.1550(4) 0.45523(18) 0.78705(10) 0.0638(6) Uani 1 1 d . . .
C22_1 C -0.2245(5) 0.4379(2) 0.73896(13) 0.0623(7) Uani 1 1 d . . .
H22A_1 H -0.3597 0.4271 0.7399 0.075 Uiso 1 1 calc R . .
C23_1 C -0.1103(4) 0.43465(19) 0.68751(11) 0.0560(7) Uani 1 1 d . . .
C24_1 C 0.0901(4) 0.4502(2) 0.68657(12) 0.0586(7) Uani 1 1 d . . .
H24A_1 H 0.1736 0.4487 0.6527 0.070 Uiso 1 1 calc R . .
C25_1 C 0.1632(5) 0.4678(2) 0.73608(13) 0.0626(7) Uani 1 1 d . . .
H25A_1 H 0.2979 0.4783 0.7366 0.075 Uiso 1 1 calc R . .
C26_1 C 0.0367(5) 0.4698(2) 0.78517(13) 0.0627(7) Uani 1 1 d . . .
H26A_1 H 0.0887 0.4820 0.8187 0.075 Uiso 1 1 calc R . .
C27_1 C -0.1991(5) 0.4147(2) 0.63702(12) 0.0601(7) Uani 1 1 d . . .
H27A_1 H -0.3355 0.4076 0.6385 0.072 Uiso 1 1 calc R . .
N27_1 N -0.0915(4) 0.40674(17) 0.59056(10) 0.0590(6) Uani 1 1 d . . .
C31_1 C 0.1856(5) 0.2822(2) 0.24982(12) 0.0602(7) Uani 1 1 d . . .
O31_1 O -0.0058(3) 0.28025(17) 0.25376(9) 0.0715(6) Uani 1 1 d . . .
H31_1 H -0.051(5) 0.283(2) 0.2979(16) 0.086 Uiso 1 1 d . . .
O32_1 O 0.2753(3) 0.27618(19) 0.29193(9) 0.0788(7) Uani 1 1 d . . .
C32_1 C 0.2782(4) 0.2922(2) 0.18843(12) 0.0597(7) Uani 1 1 d . . .
H32A_1 H 0.2181 0.3468 0.1646 0.072 Uiso 1 1 calc R . .
H32B_1 H 0.2473 0.2335 0.1737 0.072 Uiso 1 1 calc R . .
C33_1 C 0.4986(4) 0.3077(2) 0.18022(12) 0.0606(7) Uani 1 1 d . . .
H33A_1 H 0.5312 0.3683 0.1925 0.073 Uiso 1 1 calc R . .
H33B_1 H 0.5606 0.2546 0.2048 0.073 Uiso 1 1 calc R . .
C34_1 C 0.5782(4) 0.3122(2) 0.11746(12) 0.0602(7) Uani 1 1 d . . .
H34A_1 H 0.5101 0.3631 0.0930 0.072 Uiso 1 1 calc R . .
H34B_1 H 0.5490 0.2504 0.1060 0.072 Uiso 1 1 calc R . .
C35_1 C 0.7967(4) 0.3321(2) 0.10572(12) 0.0611(7) Uani 1 1 d . . .
H35A_1 H 0.8655 0.2797 0.1287 0.073 Uiso 1 1 calc R . .
H35B_1 H 0.8271 0.3925 0.1186 0.073 Uiso 1 1 calc R . .
C36_1 C 0.8721(4) 0.3404(2) 0.04218(12) 0.0595(7) Uani 1 1 d . . .
H36A_1 H 0.8000 0.3913 0.0190 0.071 Uiso 1 1 calc R . .
H36B_1 H 0.8461 0.2792 0.0297 0.071 Uiso 1 1 calc R . .
C37_1 C 1.0907(4) 0.3641(2) 0.03024(12) 0.0588(7) Uani 1 1 d . . .
H37A_1 H 1.1631 0.3105 0.0509 0.071 Uiso 1 1 calc R . .
H37B_1 H 1.1181 0.4223 0.0459 0.071 Uiso 1 1 calc R . .
C38_1 C 1.1656(4) 0.3811(2) -0.03420(12) 0.0585(7) Uani 1 1 d . . .
H38A_1 H 1.1437 0.3224 -0.0499 0.070 Uiso 1 1 calc R . .
H38B_1 H 1.0923 0.4338 -0.0554 0.070 Uiso 1 1 calc R . .
C39_1 C 1.3810(4) 0.4071(2) -0.04295(12) 0.0595(7) Uani 1 1 d . . .
H39A_1 H 1.3993 0.4676 -0.0287 0.071 Uiso 1 1 calc R . .
H39B_1 H 1.4507 0.3563 -0.0189 0.071 Uiso 1 1 calc R . .
C40_1 C 1.4739(4) 0.4195(2) -0.10431(12) 0.0567(7) Uani 1 1 d . . .
O40_1 O 1.6599(3) 0.44534(17) -0.10800(9) 0.0710(6) Uani 1 1 d . . .
H40_1 H 1.737(5) 0.459(2) -0.1493(16) 0.085 Uiso 1 1 d . . .
O41_1 O 1.3919(3) 0.40801(17) -0.14562(9) 0.0721(6) Uani 1 1 d . . .
O1W_2 O -0.1902(4) 0.87523(19) 0.60659(10) 0.0821(7) Uani 1 1 d . . .
H1A_2 H -0.322(7) 0.870(3) 0.6051(18) 0.098 Uiso 1 1 d . . .
H1B_2 H -0.216(6) 0.820(3) 0.6421(18) 0.098 Uiso 1 1 d . . .
N11_2 N 0.2612(4) 0.83386(18) 0.38027(10) 0.0633(6) Uani 1 1 d . . .
C12_2 C 0.3448(5) 0.8530(2) 0.42620(12) 0.0623(7) Uani 1 1 d . A .
H12A_2 H 0.4816 0.8506 0.4253 0.075 Uiso 1 1 calc R . .
C13_2 C 0.2393(4) 0.87633(19) 0.47520(11) 0.0554(7) Uani 1 1 d . . .
C14_2 C 0.0387(5) 0.8807(2) 0.47543(13) 0.0637(7) Uani 1 1 d . A .
H14A_2 H -0.0383 0.8961 0.5076 0.076 Uiso 1 1 calc R . .
C15_2 C -0.0475(5) 0.8621(2) 0.42779(13) 0.0657(8) Uani 1 1 d . . .
H15A_2 H -0.1838 0.8654 0.4270 0.079 Uiso 1 1 calc R A .
C16_2 C 0.0685(5) 0.8385(2) 0.38147(13) 0.0627(7) Uani 1 1 d . A .
H16A_2 H 0.0084 0.8252 0.3494 0.075 Uiso 1 1 calc R . .
C17A_2 C 0.3506(5) 0.8935(2) 0.52382(13) 0.0632(5) Uani 0.844(4) 1 d P A 1
O17_2 O 0.5335(4) 0.89183(17) 0.51882(10) 0.0632(5) Uani 0.844(4) 1 d P A 1
C17B_2 C 0.3506(5) 0.8935(2) 0.52382(13) 0.0632(5) Uani 0.156(4) 1 d P A 2
H17B_2 H 0.4878 0.8931 0.5211 0.076 Uiso 0.156(4) 1 calc PR A 2
N17_2 N 0.2436(4) 0.90949(19) 0.57174(11) 0.0626(7) Uani 1 1 d . . .
H17_2 H 0.132(5) 0.899(2) 0.5787(16) 0.075 Uiso 1 1 d . . .
N21_2 N 0.2850(4) 0.94067(18) 0.81979(10) 0.0626(6) Uani 1 1 d . . .
C22_2 C 0.2122(5) 0.9326(2) 0.77016(12) 0.0607(7) Uani 1 1 d . A .
H22A_2 H 0.0775 0.9200 0.7714 0.073 Uiso 1 1 calc R . .
C23_2 C 0.3222(5) 0.9418(2) 0.71721(12) 0.0610(7) Uani 1 1 d . . .
C24_2 C 0.5202(5) 0.9616(2) 0.71565(13) 0.0651(8) Uani 1 1 d . A .
H24A_2 H 0.6004 0.9694 0.6805 0.078 Uiso 1 1 calc R . .
C25_2 C 0.5975(5) 0.9696(2) 0.76669(13) 0.0650(8) Uani 1 1 d . . .
H25A_2 H 0.7313 0.9829 0.7668 0.078 Uiso 1 1 calc R A .
C26_2 C 0.4754(5) 0.9578(2) 0.81768(13) 0.0613(7) Uani 1 1 d . A .
H26A_2 H 0.5297 0.9621 0.8523 0.074 Uiso 1 1 calc R . .
C27A_2 C 0.2309(5) 0.9287(2) 0.66533(12) 0.0647(7) Uani 0.844(4) 1 d P A 1
H27A_2 H 0.0942 0.9243 0.6663 0.078 Uiso 0.844(4) 1 calc PR A 1
C27B_2 C 0.2309(5) 0.9287(2) 0.66533(12) 0.0647(7) Uani 0.156(4) 1 d P A 2
O27_2 O 0.015(2) 0.9439(9) 0.6715(5) 0.0647(7) Uani 0.156(4) 1 d P A 2
N27_2 N 0.3389(4) 0.92324(17) 0.61837(10) 0.0633(6) Uani 1 1 d . A .
C31_2 C 0.6176(5) 0.7860(2) 0.27958(12) 0.0594(7) Uani 1 1 d . . .
O31_2 O 0.4267(3) 0.78756(17) 0.28294(9) 0.0699(6) Uani 1 1 d . . .
H31_2 H 0.377(5) 0.800(2) 0.3208(16) 0.084 Uiso 1 1 d . . .
C32_2 C 0.7105(4) 0.7874(2) 0.21938(12) 0.0583(7) Uani 1 1 d . . .
H32A_2 H 0.6522 0.8396 0.1931 0.070 Uiso 1 1 calc R . .
H32B_2 H 0.6787 0.7261 0.2077 0.070 Uiso 1 1 calc R . .
O32_2 O 0.7078(3) 0.78278(18) 0.32198(9) 0.0763(6) Uani 1 1 d . . .
C33_2 C 0.9307(4) 0.8016(2) 0.21136(12) 0.0586(7) Uani 1 1 d . . .
H33A_2 H 0.9912 0.7483 0.2362 0.070 Uiso 1 1 calc R . .
H33B_2 H 0.9646 0.8622 0.2235 0.070 Uiso 1 1 calc R . .
C34_2 C 1.0117(4) 0.8050(2) 0.14853(12) 0.0612(7) Uani 1 1 d . . .
H34A_2 H 0.9782 0.7439 0.1369 0.073 Uiso 1 1 calc R . .
H34B_2 H 0.9479 0.8573 0.1239 0.073 Uiso 1 1 calc R . .
C35_2 C 1.2303(4) 0.8208(2) 0.13765(12) 0.0606(7) Uani 1 1 d . . .
H35A_2 H 1.2948 0.7660 0.1600 0.073 Uiso 1 1 calc R . .
H35B_2 H 1.2652 0.8795 0.1518 0.073 Uiso 1 1 calc R . .
C36_2 C 1.3073(4) 0.8312(2) 0.07403(12) 0.0609(7) Uani 1 1 d . . .
H36A_2 H 1.2369 0.8834 0.0513 0.073 Uiso 1 1 calc R . .
H36B_2 H 1.2795 0.7710 0.0606 0.073 Uiso 1 1 calc R . .
C37_2 C 1.5255(4) 0.8533(2) 0.06249(12) 0.0578(7) Uani 1 1 d . . .
H37A_2 H 1.5960 0.7990 0.0832 0.069 Uiso 1 1 calc R . .
H37B_2 H 1.5543 0.9110 0.0784 0.069 Uiso 1 1 calc R . .
C38_2 C 1.6022(4) 0.8703(2) -0.00145(12) 0.0596(7) Uani 1 1 d . . .
H38A_2 H 1.5790 0.8120 -0.0174 0.071 Uiso 1 1 calc R . .
H38B_2 H 1.5308 0.9237 -0.0227 0.071 Uiso 1 1 calc R . .
C39_2 C 1.8190(4) 0.8948(2) -0.00978(12) 0.0589(7) Uani 1 1 d . . .
H39A_2 H 1.8389 0.9548 0.0049 0.071 Uiso 1 1 calc R . .
H39B_2 H 1.8870 0.8432 0.0141 0.071 Uiso 1 1 calc R . .
C40_2 C 1.9132(4) 0.9077(2) -0.07114(12) 0.0585(7) Uani 1 1 d . . .
O40_2 O 2.1011(3) 0.92553(16) -0.07468(9) 0.0696(6) Uani 1 1 d . . .
H40_2 H 2.173(5) 0.938(2) -0.1184(16) 0.083 Uiso 1 1 d . . .
O41_2 O 1.8278(3) 0.90089(17) -0.11299(9) 0.0753(6) Uani 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
O1W_1 H1A_1 0.82(4) . ?
O1W_1 H1B_1 1.00(4) . ?
N11_1 C16_1 1.343(4) . ?
N11_1 C12_1 1.348(4) . ?
C12_1 C13_1 1.405(4) . ?
C12_1 H12A_1 0.9500 . ?
C13_1 C14_1 1.390(4) . ?
C13_1 C17_1 1.512(4) . ?
C14_1 C15_1 1.403(4) . ?
C14_1 H14A_1 0.9500 . ?
C15_1 C16_1 1.400(4) . ?
C15_1 H15A_1 0.9500 . ?
C16_1 H16A_1 0.9500 . ?
C17_1 O17_1 1.231(3) . ?
C17_1 N17_1 1.378(4) . ?
N17_1 N27_1 1.380(3) . ?
N17_1 H17_1 0.94(4) . ?
N21_1 C26_1 1.344(4) . ?
N21_1 C22_1 1.345(4) . ?
C22_1 C23_1 1.403(4) . ?
C22_1 H22A_1 0.9500 . ?
C23_1 C24_1 1.408(4) . ?
C23_1 C27_1 1.473(4) . ?
C24_1 C25_1 1.388(4) . ?
C24_1 H24A_1 0.9500 . ?
C25_1 C26_1 1.399(4) . ?
C25_1 H25A_1 0.9500 . ?
C26_1 H26A_1 0.9500 . ?
C27_1 N27_1 1.297(4) . ?
C27_1 H27A_1 0.9500 . ?
C31_1 O32_1 1.219(4) . ?
C31_1 O31_1 1.325(4) . ?
C31_1 C32_1 1.522(4) . ?
O31_1 H31_1 1.08(4) . ?
C32_1 C33_1 1.538(4) . ?
C32_1 H32A_1 0.9900 . ?
C32_1 H32B_1 0.9900 . ?
C33_1 C34_1 1.533(4) . ?
C33_1 H33A_1 0.9900 . ?
C33_1 H33B_1 0.9900 . ?
C34_1 C35_1 1.535(4) . ?
C34_1 H34A_1 0.9900 . ?
C34_1 H34B_1 0.9900 . ?
C35_1 C36_1 1.536(4) . ?
C35_1 H35A_1 0.9900 . ?
C35_1 H35B_1 0.9900 . ?
C36_1 C37_1 1.546(4) . ?
C36_1 H36A_1 0.9900 . ?
C36_1 H36B_1 0.9900 . ?
C37_1 C38_1 1.548(4) . ?
C37_1 H37A_1 0.9900 . ?
C37_1 H37B_1 0.9900 . ?
C38_1 C39_1 1.529(4) . ?
C38_1 H38A_1 0.9900 . ?
C38_1 H38B_1 0.9900 . ?
C39_1 C40_1 1.520(4) . ?
C39_1 H39A_1 0.9900 . ?
C39_1 H39B_1 0.9900 . ?
C40_1 O41_1 1.217(3) . ?
C40_1 O40_1 1.335(4) . ?
O40_1 H40_1 1.06(4) . ?
O1W_2 H1A_2 0.93(5) . ?
O1W_2 H1B_2 1.04(4) . ?
N11_2 C16_2 1.339(4) . ?
N11_2 C12_2 1.354(4) . ?
C12_2 C13_2 1.408(4) . ?
C12_2 H12A_2 0.9500 . ?
C13_2 C14_2 1.395(4) . ?
C13_2 C17A_2 1.505(4) . ?
C14_2 C15_2 1.396(4) . ?
C14_2 H14A_2 0.9500 . ?
C15_2 C16_2 1.393(4) . ?
C15_2 H15A_2 0.9500 . ?
C16_2 H16A_2 0.9500 . ?
C17A_2 O17_2 1.266(4) . ?
C17A_2 N17_2 1.355(4) . ?
N17_2 N27_2 1.387(4) . ?
N17_2 H17_2 0.79(4) . ?
N21_2 C26_2 1.340(4) . ?
N21_2 C22_2 1.351(4) . ?
C22_2 C23_2 1.396(4) . ?
C22_2 H22A_2 0.9500 . ?
C23_2 C24_2 1.401(4) . ?
C23_2 C27A_2 1.481(4) . ?
C24_2 C25_2 1.396(4) . ?
C24_2 H24A_2 0.9500 . ?
C25_2 C26_2 1.397(4) . ?
C25_2 H25A_2 0.9500 . ?
C26_2 H26A_2 0.9500 . ?
C27A_2 N27_2 1.300(4) . ?
C27A_2 H27A_2 0.9500 . ?
C31_2 O32_2 1.231(4) . ?
C31_2 O31_2 1.322(4) . ?
C31_2 C32_2 1.511(4) . ?
O31_2 H31_2 0.98(4) . ?
C32_2 C33_2 1.534(4) . ?
C32_2 H32A_2 0.9900 . ?
C32_2 H32B_2 0.9900 . ?
C33_2 C34_2 1.539(4) . ?
C33_2 H33A_2 0.9900 . ?
C33_2 H33B_2 0.9900 . ?
C34_2 C35_2 1.527(4) . ?
C34_2 H34A_2 0.9900 . ?
C34_2 H34B_2 0.9900 . ?
C35_2 C36_2 1.538(4) . ?
C35_2 H35A_2 0.9900 . ?
C35_2 H35B_2 0.9900 . ?
C36_2 C37_2 1.539(4) . ?
C36_2 H36A_2 0.9900 . ?
C36_2 H36B_2 0.9900 . ?
C37_2 C38_2 1.540(4) . ?
C37_2 H37A_2 0.9900 . ?
C37_2 H37B_2 0.9900 . ?
C38_2 C39_2 1.534(4) . ?
C38_2 H38A_2 0.9900 . ?
C38_2 H38B_2 0.9900 . ?
C39_2 C40_2 1.522(4) . ?
C39_2 H39A_2 0.9900 . ?
C39_2 H39B_2 0.9900 . ?
C40_2 O41_2 1.224(4) . ?
C40_2 O40_2 1.323(4) . ?
O40_2 H40_2 1.10(4) . ?

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
H1A_1 O1W_1 H1B_1 106(3) . . ?
C16_1 N11_1 C12_1 117.8(3) . . ?
N11_1 C12_1 C13_1 123.6(3) . . ?
N11_1 C12_1 H12A_1 118.2 . . ?
C13_1 C12_1 H12A_1 118.2 . . ?
C14_1 C13_1 C12_1 117.8(3) . . ?
C14_1 C13_1 C17_1 124.9(3) . . ?
C12_1 C13_1 C17_1 117.3(3) . . ?
C13_1 C14_1 C15_1 119.4(3) . . ?
C13_1 C14_1 H14A_1 120.3 . . ?
C15_1 C14_1 H14A_1 120.3 . . ?
C16_1 C15_1 C14_1 118.5(3) . . ?
C16_1 C15_1 H15A_1 120.8 . . ?
C14_1 C15_1 H15A_1 120.8 . . ?
N11_1 C16_1 C15_1 123.0(3) . . ?
N11_1 C16_1 H16A_1 118.5 . . ?
C15_1 C16_1 H16A_1 118.5 . . ?
O17_1 C17_1 N17_1 123.0(3) . . ?
O17_1 C17_1 C13_1 121.9(3) . . ?
N17_1 C17_1 C13_1 115.2(3) . . ?
C17_1 N17_1 N27_1 117.9(3) . . ?
C17_1 N17_1 H17_1 124(2) . . ?
N27_1 N17_1 H17_1 118(2) . . ?
C26_1 N21_1 C22_1 117.2(3) . . ?
N21_1 C22_1 C23_1 124.2(3) . . ?
N21_1 C22_1 H22A_1 117.9 . . ?
C23_1 C22_1 H22A_1 117.9 . . ?
C22_1 C23_1 C24_1 117.5(3) . . ?
C22_1 C23_1 C27_1 120.4(3) . . ?
C24_1 C23_1 C27_1 122.0(3) . . ?
C25_1 C24_1 C23_1 118.6(3) . . ?
C25_1 C24_1 H24A_1 120.7 . . ?
C23_1 C24_1 H24A_1 120.7 . . ?
C24_1 C25_1 C26_1 119.4(3) . . ?
C24_1 C25_1 H25A_1 120.3 . . ?
C26_1 C25_1 H25A_1 120.3 . . ?
N21_1 C26_1 C25_1 123.0(3) . . ?
N21_1 C26_1 H26A_1 118.5 . . ?
C25_1 C26_1 H26A_1 118.5 . . ?
N27_1 C27_1 C23_1 120.1(3) . . ?
N27_1 C27_1 H27A_1 120.0 . . ?
C23_1 C27_1 H27A_1 120.0 . . ?
C27_1 N27_1 N17_1 116.3(3) . . ?
O32_1 C31_1 O31_1 122.1(3) . . ?
O32_1 C31_1 C32_1 124.5(3) . . ?
O31_1 C31_1 C32_1 113.4(3) . . ?
C31_1 O31_1 H31_1 105(2) . . ?
C31_1 C32_1 C33_1 115.8(2) . . ?
C31_1 C32_1 H32A_1 108.3 . . ?
C33_1 C32_1 H32A_1 108.3 . . ?
C31_1 C32_1 H32B_1 108.3 . . ?
C33_1 C32_1 H32B_1 108.3 . . ?
H32A_1 C32_1 H32B_1 107.4 . . ?
C34_1 C33_1 C32_1 111.6(2) . . ?
C34_1 C33_1 H33A_1 109.3 . . ?
C32_1 C33_1 H33A_1 109.3 . . ?
C34_1 C33_1 H33B_1 109.3 . . ?
C32_1 C33_1 H33B_1 109.3 . . ?
H33A_1 C33_1 H33B_1 108.0 . . ?
C33_1 C34_1 C35_1 114.3(2) . . ?
C33_1 C34_1 H34A_1 108.7 . . ?
C35_1 C34_1 H34A_1 108.7 . . ?
C33_1 C34_1 H34B_1 108.7 . . ?
C35_1 C34_1 H34B_1 108.7 . . ?
H34A_1 C34_1 H34B_1 107.6 . . ?
C34_1 C35_1 C36_1 113.5(2) . . ?
C34_1 C35_1 H35A_1 108.9 . . ?
C36_1 C35_1 H35A_1 108.9 . . ?
C34_1 C35_1 H35B_1 108.9 . . ?
C36_1 C35_1 H35B_1 108.9 . . ?
H35A_1 C35_1 H35B_1 107.7 . . ?
C35_1 C36_1 C37_1 113.3(2) . . ?
C35_1 C36_1 H36A_1 108.9 . . ?
C37_1 C36_1 H36A_1 108.9 . . ?
C35_1 C36_1 H36B_1 108.9 . . ?
C37_1 C36_1 H36B_1 108.9 . . ?
H36A_1 C36_1 H36B_1 107.7 . . ?
C36_1 C37_1 C38_1 113.9(2) . . ?
C36_1 C37_1 H37A_1 108.8 . . ?
C38_1 C37_1 H37A_1 108.8 . . ?
C36_1 C37_1 H37B_1 108.8 . . ?
C38_1 C37_1 H37B_1 108.8 . . ?
H37A_1 C37_1 H37B_1 107.7 . . ?
C39_1 C38_1 C37_1 111.1(2) . . ?
C39_1 C38_1 H38A_1 109.4 . . ?
C37_1 C38_1 H38A_1 109.4 . . ?
C39_1 C38_1 H38B_1 109.4 . . ?
C37_1 C38_1 H38B_1 109.4 . . ?
H38A_1 C38_1 H38B_1 108.0 . . ?
C40_1 C39_1 C38_1 115.9(2) . . ?
C40_1 C39_1 H39A_1 108.3 . . ?
C38_1 C39_1 H39A_1 108.3 . . ?
C40_1 C39_1 H39B_1 108.3 . . ?
C38_1 C39_1 H39B_1 108.3 . . ?
H39A_1 C39_1 H39B_1 107.4 . . ?
O41_1 C40_1 O40_1 123.2(3) . . ?
O41_1 C40_1 C39_1 125.2(3) . . ?
O40_1 C40_1 C39_1 111.6(2) . . ?
C40_1 O40_1 H40_1 118(2) . . ?
H1A_2 O1W_2 H1B_2 83(3) . . ?
C16_2 N11_2 C12_2 118.0(3) . . ?
N11_2 C12_2 C13_2 123.4(3) . . ?
N11_2 C12_2 H12A_2 118.3 . . ?
C13_2 C12_2 H12A_2 118.3 . . ?
C14_2 C13_2 C12_2 117.5(3) . . ?
C14_2 C13_2 C17A_2 124.7(3) . . ?
C12_2 C13_2 C17A_2 117.8(3) . . ?
C13_2 C14_2 C15_2 119.2(3) . . ?
C13_2 C14_2 H14A_2 120.4 . . ?
C15_2 C14_2 H14A_2 120.4 . . ?
C16_2 C15_2 C14_2 119.3(3) . . ?
C16_2 C15_2 H15A_2 120.4 . . ?
C14_2 C15_2 H15A_2 120.4 . . ?
N11_2 C16_2 C15_2 122.7(3) . . ?
N11_2 C16_2 H16A_2 118.7 . . ?
C15_2 C16_2 H16A_2 118.7 . . ?
O17_2 C17A_2 N17_2 123.6(3) . . ?
O17_2 C17A_2 C13_2 120.2(3) . . ?
N17_2 C17A_2 C13_2 116.1(3) . . ?
C17A_2 N17_2 N27_2 118.5(3) . . ?
C17A_2 N17_2 H17_2 125(3) . . ?
N27_2 N17_2 H17_2 115(3) . . ?
C26_2 N21_2 C22_2 117.4(3) . . ?
N21_2 C22_2 C23_2 124.1(3) . . ?
N21_2 C22_2 H22A_2 117.9 . . ?
C23_2 C22_2 H22A_2 117.9 . . ?
C22_2 C23_2 C24_2 117.6(3) . . ?
C22_2 C23_2 C27A_2 120.3(3) . . ?
C24_2 C23_2 C27A_2 122.0(3) . . ?
C25_2 C24_2 C23_2 118.8(3) . . ?
C25_2 C24_2 H24A_2 120.6 . . ?
C23_2 C24_2 H24A_2 120.6 . . ?
C24_2 C25_2 C26_2 119.1(3) . . ?
C24_2 C25_2 H25A_2 120.4 . . ?
C26_2 C25_2 H25A_2 120.4 . . ?
N21_2 C26_2 C25_2 122.8(3) . . ?
N21_2 C26_2 H26A_2 118.6 . . ?
C25_2 C26_2 H26A_2 118.6 . . ?
N27_2 C27A_2 C23_2 119.6(3) . . ?
N27_2 C27A_2 H27A_2 120.2 . . ?
C23_2 C27A_2 H27A_2 120.2 . . ?
C27A_2 N27_2 N17_2 116.4(3) . . ?
O32_2 C31_2 O31_2 122.3(3) . . ?
O32_2 C31_2 C32_2 124.3(3) . . ?
O31_2 C31_2 C32_2 113.4(3) . . ?
C31_2 O31_2 H31_2 109(2) . . ?
C31_2 C32_2 C33_2 115.4(2) . . ?
C31_2 C32_2 H32A_2 108.4 . . ?
C33_2 C32_2 H32A_2 108.4 . . ?
C31_2 C32_2 H32B_2 108.4 . . ?
C33_2 C32_2 H32B_2 108.4 . . ?
H32A_2 C32_2 H32B_2 107.5 . . ?
C32_2 C33_2 C34_2 111.8(2) . . ?
C32_2 C33_2 H33A_2 109.3 . . ?
C34_2 C33_2 H33A_2 109.3 . . ?
C32_2 C33_2 H33B_2 109.3 . . ?
C34_2 C33_2 H33B_2 109.3 . . ?
H33A_2 C33_2 H33B_2 107.9 . . ?
C35_2 C34_2 C33_2 114.2(2) . . ?
C35_2 C34_2 H34A_2 108.7 . . ?
C33_2 C34_2 H34A_2 108.7 . . ?
C35_2 C34_2 H34B_2 108.7 . . ?
C33_2 C34_2 H34B_2 108.7 . . ?
H34A_2 C34_2 H34B_2 107.6 . . ?
C34_2 C35_2 C36_2 113.6(2) . . ?
C34_2 C35_2 H35A_2 108.8 . . ?
C36_2 C35_2 H35A_2 108.8 . . ?
C34_2 C35_2 H35B_2 108.8 . . ?
C36_2 C35_2 H35B_2 108.8 . . ?
H35A_2 C35_2 H35B_2 107.7 . . ?
C35_2 C36_2 C37_2 113.7(2) . . ?
C35_2 C36_2 H36A_2 108.8 . . ?
C37_2 C36_2 H36A_2 108.8 . . ?
C35_2 C36_2 H36B_2 108.8 . . ?
C37_2 C36_2 H36B_2 108.8 . . ?
H36A_2 C36_2 H36B_2 107.7 . . ?
C36_2 C37_2 C38_2 114.3(2) . . ?
C36_2 C37_2 H37A_2 108.7 . . ?
C38_2 C37_2 H37A_2 108.7 . . ?
C36_2 C37_2 H37B_2 108.7 . . ?
C38_2 C37_2 H37B_2 108.7 . . ?
H37A_2 C37_2 H37B_2 107.6 . . ?
C39_2 C38_2 C37_2 111.4(2) . . ?
C39_2 C38_2 H38A_2 109.4 . . ?
C37_2 C38_2 H38A_2 109.4 . . ?
C39_2 C38_2 H38B_2 109.4 . . ?
C37_2 C38_2 H38B_2 109.4 . . ?
H38A_2 C38_2 H38B_2 108.0 . . ?
C40_2 C39_2 C38_2 116.0(2) . . ?
C40_2 C39_2 H39A_2 108.3 . . ?
C38_2 C39_2 H39A_2 108.3 . . ?
C40_2 C39_2 H39B_2 108.3 . . ?
C38_2 C39_2 H39B_2 108.3 . . ?
H39A_2 C39_2 H39B_2 107.4 . . ?
O41_2 C40_2 O40_2 122.8(3) . . ?
O41_2 C40_2 C39_2 124.7(3) . . ?
O40_2 C40_2 C39_2 112.5(3) . . ?
C40_2 O40_2 H40_2 114.7(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16_1 N11_1 C12_1 C13_1 -0.1(4) . . . . ?
N11_1 C12_1 C13_1 C14_1 -0.5(4) . . . . ?
N11_1 C12_1 C13_1 C17_1 178.9(2) . . . . ?
C12_1 C13_1 C14_1 C15_1 0.6(4) . . . . ?
C17_1 C13_1 C14_1 C15_1 -178.7(3) . . . . ?
C13_1 C14_1 C15_1 C16_1 -0.2(5) . . . . ?
C12_1 N11_1 C16_1 C15_1 0.5(4) . . . . ?
C14_1 C15_1 C16_1 N11_1 -0.3(5) . . . . ?
C14_1 C13_1 C17_1 O17_1 -163.9(3) . . . . ?
C12_1 C13_1 C17_1 O17_1 16.7(4) . . . . ?
C14_1 C13_1 C17_1 N17_1 17.1(4) . . . . ?
C12_1 C13_1 C17_1 N17_1 -162.2(2) . . . . ?
O17_1 C17_1 N17_1 N27_1 3.1(4) . . . . ?
C13_1 C17_1 N17_1 N27_1 -178.0(2) . . . . ?
C26_1 N21_1 C22_1 C23_1 -0.4(5) . . . . ?
N21_1 C22_1 C23_1 C24_1 0.3(4) . . . . ?
N21_1 C22_1 C23_1 C27_1 179.7(3) . . . . ?
C22_1 C23_1 C24_1 C25_1 0.0(4) . . . . ?
C27_1 C23_1 C24_1 C25_1 -179.4(3) . . . . ?
C23_1 C24_1 C25_1 C26_1 -0.2(4) . . . . ?
C22_1 N21_1 C26_1 C25_1 0.1(4) . . . . ?
C24_1 C25_1 C26_1 N21_1 0.1(5) . . . . ?
C22_1 C23_1 C27_1 N27_1 -176.3(3) . . . . ?
C24_1 C23_1 C27_1 N27_1 3.0(4) . . . . ?
C23_1 C27_1 N27_1 N17_1 -179.2(2) . . . . ?
C17_1 N17_1 N27_1 C27_1 -179.6(3) . . . . ?
O32_1 C31_1 C32_1 C33_1 -7.7(5) . . . . ?
O31_1 C31_1 C32_1 C33_1 172.5(3) . . . . ?
C31_1 C32_1 C33_1 C34_1 177.4(3) . . . . ?
C32_1 C33_1 C34_1 C35_1 177.4(2) . . . . ?
C33_1 C34_1 C35_1 C36_1 -177.6(3) . . . . ?
C34_1 C35_1 C36_1 C37_1 177.9(2) . . . . ?
C35_1 C36_1 C37_1 C38_1 -175.2(2) . . . . ?
C36_1 C37_1 C38_1 C39_1 178.3(2) . . . . ?
C37_1 C38_1 C39_1 C40_1 176.4(2) . . . . ?
C38_1 C39_1 C40_1 O41_1 -2.0(4) . . . . ?
C38_1 C39_1 C40_1 O40_1 177.8(2) . . . . ?
C16_2 N11_2 C12_2 C13_2 0.8(4) . . . . ?
N11_2 C12_2 C13_2 C14_2 -0.7(4) . . . . ?
N11_2 C12_2 C13_2 C17A_2 178.5(3) . . . . ?
C12_2 C13_2 C14_2 C15_2 -0.1(4) . . . . ?
C17A_2 C13_2 C14_2 C15_2 -179.2(3) . . . . ?
C13_2 C14_2 C15_2 C16_2 0.8(5) . . . . ?
C12_2 N11_2 C16_2 C15_2 0.0(5) . . . . ?
C14_2 C15_2 C16_2 N11_2 -0.7(5) . . . . ?
C14_2 C13_2 C17A_2 O17_2 -177.1(3) . . . . ?
C12_2 C13_2 C17A_2 O17_2 3.7(4) . . . . ?
C14_2 C13_2 C17A_2 N17_2 3.4(4) . . . . ?
C12_2 C13_2 C17A_2 N17_2 -175.8(3) . . . . ?
O17_2 C17A_2 N17_2 N27_2 -1.1(5) . . . . ?
C13_2 C17A_2 N17_2 N27_2 178.3(2) . . . . ?
C26_2 N21_2 C22_2 C23_2 -0.5(4) . . . . ?
N21_2 C22_2 C23_2 C24_2 -0.8(5) . . . . ?
N21_2 C22_2 C23_2 C27A_2 178.0(3) . . . . ?
C22_2 C23_2 C24_2 C25_2 1.0(4) . . . . ?
C27A_2 C23_2 C24_2 C25_2 -177.7(3) . . . . ?
C23_2 C24_2 C25_2 C26_2 -0.1(5) . . . . ?
C22_2 N21_2 C26_2 C25_2 1.5(4) . . . . ?
C24_2 C25_2 C26_2 N21_2 -1.2(5) . . . . ?
C22_2 C23_2 C27A_2 N27_2 -169.9(3) . . . . ?
C24_2 C23_2 C27A_2 N27_2 8.8(5) . . . . ?
C23_2 C27A_2 N27_2 N17_2 179.0(3) . . . . ?
C17A_2 N17_2 N27_2 C27A_2 -173.3(3) . . . . ?
O32_2 C31_2 C32_2 C33_2 -9.8(4) . . . . ?
O31_2 C31_2 C32_2 C33_2 170.8(2) . . . . ?
C31_2 C32_2 C33_2 C34_2 -178.4(2) . . . . ?
C32_2 C33_2 C34_2 C35_2 179.0(2) . . . . ?
C33_2 C34_2 C35_2 C36_2 -175.9(3) . . . . ?
C34_2 C35_2 C36_2 C37_2 176.5(2) . . . . ?
C35_2 C36_2 C37_2 C38_2 -176.2(3) . . . . ?
C36_2 C37_2 C38_2 C39_2 178.3(2) . . . . ?
C37_2 C38_2 C39_2 C40_2 176.6(2) . . . . ?
C38_2 C39_2 C40_2 O41_2 0.9(4) . . . . ?
C38_2 C39_2 C40_2 O40_2 -177.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N17_1 H17_1 O1W_1 0.94(4) 2.06(4) 2.999(4) 172(3) .
N17_2 H17_2 O1W_2 0.79(4) 2.28(4) 3.067(4) 174(4) .
O31_1 H31_1 N11_1 1.08(4) 1.64(4) 2.684(3) 162(3) .
O31_2 H31_2 N11_2 0.98(4) 1.70(4) 2.676(3) 170(3) .
O40_1 H40_1 N21_1 1.06(4) 1.63(4) 2.679(3) 168(3) 1_754
O40_2 H40_2 N21_2 1.10(4) 1.59(4) 2.681(3) 172(3) 1_754
O1W_1 H1A_1 O17_1 0.82(4) 2.15(4) 2.933(3) 159(4) 1_455
O1W_2 H1A_2 O17_2 0.93(5) 2.34(4) 2.946(4) 123(3) 1_455
O1W_1 H1B_1 O32_2 1.00(4) 1.90(4) 2.898(3) 176(3) 2_566
O1W_2 H1B_2 O32_1 1.04(4) 1.90(4) 2.940(3) 177(3) 2_566

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.069
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_33DodH2O
_database_code_depnum_ccdc_archive 'CCDC 1478928'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-C-Dod (3-pyridyl)-CONH-N=CH-(3-pyridyl), HOOC-(CH2)10-COOH hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C12 H22 O4) (H2 O)
;
_chemical_formula_sum            'C24 H34 N4 O6'
_chemical_formula_weight         474.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.9300(8)
_cell_length_b                   7.8773(10)
_cell_length_c                   24.680(3)
_cell_angle_alpha                85.562(6)
_cell_angle_beta                 83.394(6)
_cell_angle_gamma                66.198(5)
_cell_volume                     1223.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8748
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      66.29

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7913
_exptl_absorpt_correction_T_max  0.9135
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            16550
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         67.72
_reflns_number_total             4136
_reflns_number_gt                3787
_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+0.4000P] 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         4136
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O1W O 1.02066(18) 0.80347(17) 0.42105(5) 0.0286(3) Uani 1 1 d . . .
H1A H 0.906(4) 0.796(3) 0.4344(8) 0.034 Uiso 1 1 d . . .
H1B H 1.040(3) 0.741(3) 0.3910(9) 0.034 Uiso 1 1 d . . .
N11 N 0.4439(2) 0.50862(17) 0.62574(5) 0.0219(3) Uani 1 1 d . . .
C12 C 0.5238(2) 0.5869(2) 0.58348(6) 0.0198(3) Uani 1 1 d . . .
H12 H 0.6688 0.5675 0.5817 0.024 Uiso 1 1 calc R . .
C13 C 0.4027(2) 0.69580(19) 0.54198(5) 0.0189(3) Uani 1 1 d . . .
C14 C 0.1877(2) 0.7260(2) 0.54541(6) 0.0229(3) Uani 1 1 d . . .
H14 H 0.1000 0.8004 0.5184 0.027 Uiso 1 1 calc R . .
C15 C 0.1050(2) 0.6449(2) 0.58906(6) 0.0250(3) Uani 1 1 d . . .
H15 H -0.0397 0.6627 0.5921 0.030 Uiso 1 1 calc R . .
C16 C 0.2375(2) 0.5374(2) 0.62823(6) 0.0233(3) Uani 1 1 d . . .
H16 H 0.1802 0.4824 0.6578 0.028 Uiso 1 1 calc R . .
C17 C 0.5153(2) 0.77118(19) 0.49667(6) 0.0194(3) Uani 1 1 d . . .
N17 N 0.4092(2) 0.83950(17) 0.45113(5) 0.0210(3) Uani 1 1 d . . .
H17 H 0.301(3) 0.829(3) 0.4455(8) 0.025 Uiso 1 1 d . . .
O17 O 0.69283(16) 0.76842(15) 0.50114(4) 0.0263(3) Uani 1 1 d . . .
N21 N 0.4731(2) 1.18055(18) 0.22673(5) 0.0249(3) Uani 1 1 d . . .
C22 C 0.3984(2) 1.1040(2) 0.27052(6) 0.0228(3) Uani 1 1 d . . .
H22 H 0.2727 1.0850 0.2683 0.027 Uiso 1 1 calc R . .
C23 C 0.4978(2) 1.05118(19) 0.31927(6) 0.0205(3) Uani 1 1 d . . .
C24 C 0.6853(2) 1.0781(2) 0.32172(6) 0.0210(3) Uani 1 1 d . . .
H24 H 0.7575 1.0443 0.3539 0.025 Uiso 1 1 calc R . .
C25 C 0.7637(2) 1.1551(2) 0.27628(6) 0.0232(3) Uani 1 1 d . . .
H25 H 0.8906 1.1735 0.2769 0.028 Uiso 1 1 calc R . .
C26 C 0.6527(2) 1.2048(2) 0.22975(6) 0.0238(3) Uani 1 1 d . . .
H26 H 0.7065 1.2580 0.1990 0.029 Uiso 1 1 calc R . .
C27 C 0.4051(2) 0.9696(2) 0.36557(6) 0.0217(3) Uani 1 1 d . . .
H27 H 0.2748 0.9585 0.3634 0.026 Uiso 1 1 calc R . .
N27 N 0.50370(19) 0.91368(17) 0.40906(5) 0.0215(3) Uani 1 1 d . . .
C31 C 0.8052(2) 0.3471(2) 0.72208(6) 0.0207(3) Uani 1 1 d . . .
O31 O 0.61308(17) 0.35264(17) 0.71889(4) 0.0292(3) Uani 1 1 d . . .
H31 H 0.573(3) 0.395(3) 0.6843(9) 0.035 Uiso 1 1 d . . .
O32 O 0.91319(18) 0.37429(19) 0.68213(4) 0.0330(3) Uani 1 1 d . . .
C32 C 0.8762(2) 0.3017(2) 0.77934(6) 0.0212(3) Uani 1 1 d . . .
H32A H 0.8933 0.1727 0.7896 0.025 Uiso 1 1 calc R . .
H32B H 0.7626 0.3847 0.8049 0.025 Uiso 1 1 calc R . .
C33 C 1.0836(2) 0.3204(2) 0.78677(6) 0.0214(3) Uani 1 1 d . . .
H33A H 1.0654 0.4510 0.7792 0.026 Uiso 1 1 calc R . .
H33B H 1.1974 0.2422 0.7603 0.026 Uiso 1 1 calc R . .
C34 C 1.1487(2) 0.2610(2) 0.84508(6) 0.0217(3) Uani 1 1 d . . .
H34A H 1.0308 0.3354 0.8713 0.026 Uiso 1 1 calc R . .
H34B H 1.1711 0.1291 0.8518 0.026 Uiso 1 1 calc R . .
C35 C 1.3504(2) 0.2840(2) 0.85621(6) 0.0222(3) Uani 1 1 d . . .
H35A H 1.3318 0.4142 0.8475 0.027 Uiso 1 1 calc R . .
H35B H 1.4708 0.2035 0.8317 0.027 Uiso 1 1 calc R . .
C36 C 1.4043(2) 0.2344(2) 0.91579(6) 0.0219(3) Uani 1 1 d . . .
H36A H 1.2803 0.3098 0.9402 0.026 Uiso 1 1 calc R . .
H36B H 1.4300 0.1022 0.9237 0.026 Uiso 1 1 calc R . .
C37 C 1.5984(2) 0.2659(2) 0.92894(6) 0.0211(3) Uani 1 1 d . . .
H37A H 1.5770 0.3959 0.9187 0.025 Uiso 1 1 calc R . .
H37B H 1.7245 0.1840 0.9063 0.025 Uiso 1 1 calc R . .
C38 C 1.6423(2) 0.2283(2) 0.98941(6) 0.0212(3) Uani 1 1 d . . .
H38A H 1.5151 0.3078 1.0122 0.025 Uiso 1 1 calc R . .
H38B H 1.6682 0.0972 0.9994 0.025 Uiso 1 1 calc R . .
C39 C 1.8328(2) 0.2657(2) 1.00200(6) 0.0211(3) Uani 1 1 d . . .
H39A H 1.8052 0.3971 0.9922 0.025 Uiso 1 1 calc R . .
H39B H 1.9585 0.1879 0.9785 0.025 Uiso 1 1 calc R . .
C40 C 1.8854(2) 0.2273(2) 1.06177(6) 0.0203(3) Uani 1 1 d . . .
H40A H 1.7618 0.3058 1.0858 0.024 Uiso 1 1 calc R . .
H40B H 1.9155 0.0957 1.0721 0.024 Uiso 1 1 calc R . .
C41 C 2.0781(2) 0.2688(2) 1.06988(6) 0.0222(3) Uani 1 1 d . . .
H41A H 2.1967 0.1964 1.0435 0.027 Uiso 1 1 calc R . .
H41B H 2.0430 0.4019 1.0607 0.027 Uiso 1 1 calc R . .
C42 C 2.1544(2) 0.22678(19) 1.12659(6) 0.0203(3) Uani 1 1 d . . .
O42 O 2.31735(18) 0.27259(17) 1.13019(5) 0.0300(3) Uani 1 1 d . . .
H42 H 2.360(3) 0.242(3) 1.1628(9) 0.036 Uiso 1 1 d . . .
O43 O 2.07824(17) 0.15793(17) 1.16450(4) 0.0306(3) Uani 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
O1W H1A 0.85(2) . ?
O1W H1B 0.89(2) . ?
N11 C12 1.3482(19) . ?
N11 C16 1.350(2) . ?
C12 C13 1.403(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(2) . ?
C13 C17 1.5107(19) . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2393(19) . ?
C17 N17 1.3676(19) . ?
N17 N27 1.3809(17) . ?
N17 H17 0.81(2) . ?
N21 C26 1.344(2) . ?
N21 C22 1.350(2) . ?
C22 C23 1.406(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.407(2) . ?
C23 C27 1.477(2) . ?
C24 C25 1.393(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.291(2) . ?
C27 H27 0.9500 . ?
C31 O32 1.2268(18) . ?
C31 O31 1.3257(18) . ?
C31 C32 1.5187(19) . ?
O31 H31 0.92(2) . ?
C32 C33 1.535(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5390(19) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.537(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5406(19) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.536(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.5398(19) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.532(2) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.5381(19) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.534(2) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.5184(19) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 O43 1.2194(18) . ?
C42 O42 1.3305(19) . ?
O42 H42 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A O1W H1B 98(2) . . ?
C12 N11 C16 118.24(12) . . ?
N11 C12 C13 123.08(13) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 118.01(13) . . ?
C12 C13 C17 117.03(13) . . ?
C14 C13 C17 124.96(12) . . ?
C15 C14 C13 118.94(13) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.17(13) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N11 C16 C15 122.55(13) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
O17 C17 N17 123.21(13) . . ?
O17 C17 C13 121.22(12) . . ?
N17 C17 C13 115.57(13) . . ?
C17 N17 N27 117.71(13) . . ?
C17 N17 H17 124.7(13) . . ?
N27 N17 H17 117.2(13) . . ?
C26 N21 C22 118.26(12) . . ?
N21 C22 C23 123.11(14) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C22 C23 C24 117.82(13) . . ?
C22 C23 C27 119.84(13) . . ?
C24 C23 C27 122.35(13) . . ?
C25 C24 C23 119.03(13) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 119.05(14) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N21 C26 C25 122.73(13) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
N27 C27 C23 119.04(13) . . ?
N27 C27 H27 120.5 . . ?
C23 C27 H27 120.5 . . ?
C27 N27 N17 116.54(13) . . ?
O32 C31 O31 122.40(13) . . ?
O32 C31 C32 124.34(13) . . ?
O31 C31 C32 113.26(12) . . ?
C31 O31 H31 108.6(13) . . ?
C31 C32 C33 115.13(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 111.25(11) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C33 114.12(11) . . ?
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 C36 112.91(11) . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 114.12(12) . . ?
C37 C36 H36A 108.7 . . ?
C35 C36 H36A 108.7 . . ?
C37 C36 H36B 108.7 . . ?
C35 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C36 C37 C38 113.75(11) . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37B 108.8 . . ?
C38 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C39 C38 C37 112.96(11) . . ?
C39 C38 H38A 109.0 . . ?
C37 C38 H38A 109.0 . . ?
C39 C38 H38B 109.0 . . ?
C37 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C38 C39 C40 115.02(11) . . ?
C38 C39 H39A 108.5 . . ?
C40 C39 H39A 108.5 . . ?
C38 C39 H39B 108.5 . . ?
C40 C39 H39B 108.5 . . ?
H39A C39 H39B 107.5 . . ?
C41 C40 C39 110.77(11) . . ?
C41 C40 H40A 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 108.1 . . ?
C42 C41 C40 116.16(12) . . ?
C42 C41 H41A 108.2 . . ?
C40 C41 H41A 108.2 . . ?
C42 C41 H41B 108.2 . . ?
C40 C41 H41B 108.2 . . ?
H41A C41 H41B 107.4 . . ?
O43 C42 O42 123.44(13) . . ?
O43 C42 C41 124.70(13) . . ?
O42 C42 C41 111.86(12) . . ?
C42 O42 H42 109.2(14) . . ?

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 -0.4(2) . . . . ?
N11 C12 C13 C14 0.9(2) . . . . ?
N11 C12 C13 C17 -178.81(13) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C17 C13 C14 C15 178.78(14) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C12 N11 C16 C15 -0.2(2) . . . . ?
C14 C15 C16 N11 0.2(2) . . . . ?
C12 C13 C17 O17 -13.7(2) . . . . ?
C14 C13 C17 O17 166.55(14) . . . . ?
C12 C13 C17 N17 165.67(12) . . . . ?
C14 C13 C17 N17 -14.1(2) . . . . ?
O17 C17 N17 N27 -2.0(2) . . . . ?
C13 C17 N17 N27 178.61(11) . . . . ?
C26 N21 C22 C23 0.9(2) . . . . ?
N21 C22 C23 C24 -0.8(2) . . . . ?
N21 C22 C23 C27 179.52(13) . . . . ?
C22 C23 C24 C25 0.0(2) . . . . ?
C27 C23 C24 C25 179.71(13) . . . . ?
C23 C24 C25 C26 0.5(2) . . . . ?
C22 N21 C26 C25 -0.3(2) . . . . ?
C24 C25 C26 N21 -0.4(2) . . . . ?
C22 C23 C27 N27 176.72(13) . . . . ?
C24 C23 C27 N27 -3.0(2) . . . . ?
C23 C27 N27 N17 179.68(12) . . . . ?
C17 N17 N27 C27 176.98(13) . . . . ?
O32 C31 C32 C33 9.0(2) . . . . ?
O31 C31 C32 C33 -171.79(12) . . . . ?
C31 C32 C33 C34 -176.78(12) . . . . ?
C32 C33 C34 C35 -177.55(12) . . . . ?
C33 C34 C35 C36 176.63(12) . . . . ?
C34 C35 C36 C37 -176.90(12) . . . . ?
C35 C36 C37 C38 176.18(12) . . . . ?
C36 C37 C38 C39 -178.43(12) . . . . ?
C37 C38 C39 C40 -179.13(12) . . . . ?
C38 C39 C40 C41 179.93(12) . . . . ?
C39 C40 C41 C42 -176.81(12) . . . . ?
C40 C41 C42 O43 2.6(2) . . . . ?
C40 C41 C42 O42 -177.99(12) . . . . ?

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
N17 H17 O1W 0.81(2) 2.19(2) 2.9986(18) 173.8(18) 1_455
O31 H31 N11 0.92(2) 1.77(2) 2.6812(16) 167.4(19) .
O42 H42 N21 0.87(2) 1.79(2) 2.6570(17) 174(2) 1_746
O1W H1A O17 0.85(2) 2.14(2) 2.9211(16) 152.6(19) .
O1W H1B O32 0.89(2) 2.02(2) 2.9019(17) 173.1(19) 2_766

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23Glu
_database_code_depnum_ccdc_archive 'CCDC 1478933'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-A-Glu (2-pyridyl)-CONH-NHCO-(3-pyridyl), HOOC-(CH2)3-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C5 H8 O4)
;
_chemical_formula_sum            'C17 H18 N4 O5'
_chemical_formula_weight         358.35

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   20.694(3)
_cell_length_b                   5.5714(8)
_cell_length_c                   14.954(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.047(7)
_cell_angle_gamma                90.00
_cell_volume                     1665.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6307
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      30.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_T_max  0.9893
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24390
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.02
_diffrn_reflns_theta_max         31.51
_reflns_number_total             5305
_reflns_number_gt                3401
_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)+(0.1000P)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         5305
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_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 1.02838(8) 0.3480(3) 0.86541(11) 0.0276(4) Uani 1 1 d . . .
C12 C 0.99755(9) 0.5553(3) 0.87349(12) 0.0237(4) Uani 1 1 d . . .
C13 C 1.02713(10) 0.7441(3) 0.92984(13) 0.0287(4) Uani 1 1 d . . .
H13A H 1.0035 0.8894 0.9316 0.034 Uiso 1 1 calc R . .
C14 C 1.09200(10) 0.7149(4) 0.98341(14) 0.0322(4) Uani 1 1 d . . .
H14A H 1.1137 0.8385 1.0239 0.039 Uiso 1 1 calc R . .
C15 C 1.12434(9) 0.5024(4) 0.97661(13) 0.0322(4) Uani 1 1 d . . .
H15A H 1.1689 0.4773 1.0126 0.039 Uiso 1 1 calc R . .
C16 C 1.09146(10) 0.3255(4) 0.91693(14) 0.0316(4) Uani 1 1 d . . .
H16A H 1.1148 0.1811 0.9123 0.038 Uiso 1 1 calc R . .
C17 C 0.92602(9) 0.5795(3) 0.82137(12) 0.0251(4) Uani 1 1 d . . .
N17 N 0.89985(8) 0.3797(3) 0.77457(11) 0.0265(3) Uani 1 1 d . . .
H17 H 0.9257(11) 0.252(4) 0.7816(16) 0.032 Uiso 1 1 d . . .
O17 O 0.89429(7) 0.7639(2) 0.82451(10) 0.0297(3) Uani 1 1 d . . .
N21 N 0.62687(8) 0.3015(3) 0.62091(11) 0.0267(3) Uani 1 1 d . . .
C22 C 0.69267(9) 0.3261(3) 0.65714(13) 0.0260(4) Uani 1 1 d . . .
H22A H 0.7087 0.4687 0.6903 0.031 Uiso 1 1 calc R . .
C23 C 0.73863(9) 0.1518(3) 0.64829(12) 0.0248(4) Uani 1 1 d . . .
C24 C 0.71500(9) -0.0554(3) 0.59927(13) 0.0272(4) Uani 1 1 d . . .
H24A H 0.7452 -0.1778 0.5921 0.033 Uiso 1 1 calc R . .
C25 C 0.64714(10) -0.0821(4) 0.56094(13) 0.0290(4) Uani 1 1 d . . .
H25A H 0.6297 -0.2219 0.5267 0.035 Uiso 1 1 calc R . .
C26 C 0.60526(9) 0.1002(4) 0.57384(13) 0.0279(4) Uani 1 1 d . . .
H26A H 0.5585 0.0817 0.5478 0.033 Uiso 1 1 calc R . .
C27 C 0.80967(9) 0.1781(3) 0.69430(12) 0.0257(4) Uani 1 1 d . . .
H27A H 0.8388 0.0445 0.6984 0.031 Uiso 1 1 calc R . .
N27 N 0.83294(7) 0.3802(3) 0.72910(11) 0.0273(4) Uani 1 1 d . . .
C31 C 0.47895(9) 0.5516(3) 0.63059(12) 0.0254(4) Uani 1 1 d . . .
O31 O 0.54145(7) 0.6288(3) 0.65589(10) 0.0307(3) Uani 1 1 d . . .
H31 H 0.5683(12) 0.509(4) 0.6433(16) 0.037 Uiso 1 1 d . . .
O32 O 0.46271(7) 0.3665(3) 0.58837(10) 0.0339(4) Uani 1 1 d . . .
C32 C 0.43216(9) 0.7182(3) 0.66152(14) 0.0287(4) Uani 1 1 d . . .
H32A H 0.4402 0.8835 0.6426 0.034 Uiso 1 1 calc R . .
H32B H 0.4431 0.7154 0.7300 0.034 Uiso 1 1 calc R . .
C33 C 0.35834(9) 0.6612(3) 0.62388(14) 0.0278(4) Uani 1 1 d . . .
H33A H 0.3484 0.6442 0.5558 0.033 Uiso 1 1 calc R . .
H33B H 0.3318 0.7978 0.6373 0.033 Uiso 1 1 calc R . .
C34 C 0.33641(9) 0.4337(3) 0.66398(12) 0.0254(4) Uani 1 1 d . . .
H34A H 0.3581 0.2936 0.6432 0.030 Uiso 1 1 calc R . .
H34B H 0.3517 0.4406 0.7324 0.030 Uiso 1 1 calc R . .
C35 C 0.26237(9) 0.3999(4) 0.63570(13) 0.0285(4) Uani 1 1 d . . .
O35 O 0.24136(7) 0.2454(3) 0.68906(10) 0.0338(4) Uani 1 1 d . . .
H35 H 0.1983(13) 0.241(4) 0.6731(18) 0.041 Uiso 1 1 d . . .
O36 O 0.22497(8) 0.4945(4) 0.57070(15) 0.0720(7) Uani 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 1.338(2) . ?
N11 C12 1.340(2) . ?
C12 C13 1.387(3) . ?
C12 C17 1.489(3) . ?
C13 C14 1.383(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.227(2) . ?
C17 N17 1.351(2) . ?
N17 N27 1.375(2) . ?
N17 H17 0.88(2) . ?
N21 C22 1.335(2) . ?
N21 C26 1.338(2) . ?
C22 C23 1.389(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(3) . ?
C23 C27 1.460(2) . ?
C24 C25 1.380(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 N27 1.281(2) . ?
C27 H27A 0.9500 . ?
C31 O32 1.211(2) . ?
C31 O31 1.322(2) . ?
C31 C32 1.499(3) . ?
O31 H31 0.92(3) . ?
C32 C33 1.518(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.521(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.492(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 O36 1.196(2) . ?
C35 O35 1.321(2) . ?
O35 H35 0.86(3) . ?

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 116.42(17) . . ?
N11 C12 C13 124.27(17) . . ?
N11 C12 C17 117.57(16) . . ?
C13 C12 C17 118.11(16) . . ?
C14 C13 C12 118.15(18) . . ?
C14 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
C15 C14 C13 118.41(19) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C14 C15 C16 119.53(18) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
N11 C16 C15 123.19(19) . . ?
N11 C16 H16A 118.4 . . ?
C15 C16 H16A 118.4 . . ?
O17 C17 N17 124.28(17) . . ?
O17 C17 C12 121.68(16) . . ?
N17 C17 C12 113.99(16) . . ?
C17 N17 N27 118.11(16) . . ?
C17 N17 H17 116.9(15) . . ?
N27 N17 H17 124.4(15) . . ?
C22 N21 C26 117.77(16) . . ?
N21 C22 C23 122.73(17) . . ?
N21 C22 H22A 118.6 . . ?
C23 C22 H22A 118.6 . . ?
C24 C23 C22 118.43(17) . . ?
C24 C23 C27 120.41(17) . . ?
C22 C23 C27 121.04(17) . . ?
C25 C24 C23 119.35(18) . . ?
C25 C24 H24A 120.3 . . ?
C23 C24 H24A 120.3 . . ?
C24 C25 C26 118.07(18) . . ?
C24 C25 H25A 121.0 . . ?
C26 C25 H25A 121.0 . . ?
N21 C26 C25 123.64(18) . . ?
N21 C26 H26A 118.2 . . ?
C25 C26 H26A 118.2 . . ?
N27 C27 C23 120.41(17) . . ?
N27 C27 H27A 119.8 . . ?
C23 C27 H27A 119.8 . . ?
C27 N27 N17 115.04(16) . . ?
O32 C31 O31 123.03(17) . . ?
O32 C31 C32 125.08(17) . . ?
O31 C31 C32 111.88(16) . . ?
C31 O31 H31 107.6(14) . . ?
C31 C32 C33 115.11(16) . . ?
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 113.76(15) . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 112.54(15) . . ?
C35 C34 H34A 109.1 . . ?
C33 C34 H34A 109.1 . . ?
C35 C34 H34B 109.1 . . ?
C33 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
O36 C35 O35 122.20(18) . . ?
O36 C35 C34 125.08(17) . . ?
O35 C35 C34 112.70(16) . . ?
C35 O35 H35 109.4(17) . . ?

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(3) . . . . ?
C16 N11 C12 C17 -176.37(16) . . . . ?
N11 C12 C13 C14 -2.0(3) . . . . ?
C17 C12 C13 C14 175.38(16) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C12 N11 C16 C15 0.6(3) . . . . ?
C14 C15 C16 N11 -1.1(3) . . . . ?
N11 C12 C17 O17 -179.51(16) . . . . ?
C13 C12 C17 O17 2.9(3) . . . . ?
N11 C12 C17 N17 2.9(2) . . . . ?
C13 C12 C17 N17 -174.68(16) . . . . ?
O17 C17 N17 N27 -1.5(3) . . . . ?
C12 C17 N17 N27 176.01(14) . . . . ?
C26 N21 C22 C23 -0.5(3) . . . . ?
N21 C22 C23 C24 0.4(3) . . . . ?
N21 C22 C23 C27 -175.72(17) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C27 C23 C24 C25 176.22(16) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C22 N21 C26 C25 0.1(3) . . . . ?
C24 C25 C26 N21 0.4(3) . . . . ?
C24 C23 C27 N27 170.80(17) . . . . ?
C22 C23 C27 N27 -13.2(3) . . . . ?
C23 C27 N27 N17 176.92(14) . . . . ?
C17 N17 N27 C27 -173.04(16) . . . . ?
O32 C31 C32 C33 -8.9(3) . . . . ?
O31 C31 C32 C33 171.85(15) . . . . ?
C31 C32 C33 C34 70.1(2) . . . . ?
C32 C33 C34 C35 172.25(16) . . . . ?
C33 C34 C35 O36 19.7(3) . . . . ?
C33 C34 C35 O35 -162.22(17) . . . . ?

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 N21 0.92(3) 1.77(3) 2.684(2) 174(2) .
O35 H35 O17 0.86(3) 1.93(3) 2.763(2) 163(2) 2_646

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.097
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_42Azl2H2O
_database_code_depnum_ccdc_archive 'CCDC 1478934'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-D-Azl [(4-pyridyl)-CONH-N=CH-(2-pyridyl)]2, HOOC-(CH2)7-COOH dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O)2 (C9 H16 O4) (H2 O)2
;
_chemical_formula_sum            'C33 H40 N8 O8'
_chemical_formula_weight         676.73

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   36.802(8)
_cell_length_b                   7.2815(14)
_cell_length_c                   12.533(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.978(8)
_cell_angle_gamma                90.00
_cell_volume                     3354.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      31.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_T_max  0.9903
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68658
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         31.56
_reflns_number_total             10990
_reflns_number_gt                8106
_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)+(0.1000P)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         10990
_refine_ls_number_parameters     494
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.3093
_refine_ls_wR_factor_gt          0.3006
_refine_ls_goodness_of_fit_ref   2.015
_refine_ls_restrained_S_all      2.025
_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
O1W O -0.00239(8) 0.1105(5) -0.2420(2) 0.0805(10) Uani 1 1 d . . .
H1A H 0.0078(14) 0.103(7) -0.302(4) 0.097 Uiso 1 1 d . . .
H1B H -0.0131(13) 0.233(9) -0.247(4) 0.097 Uiso 1 1 d . . .
O2W O 0.62365(5) 0.0886(3) 0.22916(13) 0.0368(4) Uani 1 1 d . . .
H2A H 0.6142(9) 0.104(4) 0.162(3) 0.044 Uiso 1 1 d . . .
H2B H 0.6099(9) 0.012(5) 0.252(3) 0.044 Uiso 1 1 d . . .
N11 N 0.13689(6) 0.4112(3) -0.1956(2) 0.0458(5) Uani 1 1 d . . .
C12 C 0.14013(8) 0.4297(4) -0.0898(2) 0.0494(7) Uani 1 1 d . . .
H12 H 0.1634 0.4584 -0.0577 0.059 Uiso 1 1 calc R . .
C13 C 0.11141(8) 0.4091(4) -0.0247(2) 0.0502(7) Uani 1 1 d . . .
H13 H 0.1150 0.4258 0.0503 0.060 Uiso 1 1 calc R . .
C14 C 0.07735(7) 0.3641(3) -0.0688(2) 0.0362(5) Uani 1 1 d . . .
C15 C 0.07390(8) 0.3437(4) -0.1784(2) 0.0454(6) Uani 1 1 d . . .
H15 H 0.0510 0.3142 -0.2124 0.054 Uiso 1 1 calc R . .
C16 C 0.10409(8) 0.3666(4) -0.2381(2) 0.0510(7) Uani 1 1 d . . .
H16 H 0.1014 0.3496 -0.3132 0.061 Uiso 1 1 calc R . .
C17 C 0.04673(7) 0.3410(3) 0.0048(2) 0.0389(5) Uani 1 1 d . . .
N17 N 0.01571(6) 0.2687(3) -0.03862(18) 0.0395(5) Uani 1 1 d . . .
H17 H 0.0119(9) 0.252(5) -0.102(3) 0.047 Uiso 1 1 d . . .
O17 O 0.05068(5) 0.3859(3) 0.09921(15) 0.0471(5) Uani 1 1 d . . .
N21 N -0.07032(7) 0.1592(4) 0.1567(2) 0.0547(6) Uani 1 1 d . . .
C22 C -0.07347(8) 0.1454(4) 0.0485(2) 0.0424(6) Uani 1 1 d . . .
C23 C -0.10508(8) 0.0956(4) -0.0043(2) 0.0492(7) Uani 1 1 d . . .
H23 H -0.1066 0.0854 -0.0800 0.059 Uiso 1 1 calc R . .
C24 C -0.13462(9) 0.0606(5) 0.0540(3) 0.0597(8) Uani 1 1 d . . .
H24 H -0.1571 0.0286 0.0181 0.072 Uiso 1 1 calc R . .
C25 C -0.13251(8) 0.0705(4) 0.1637(3) 0.0541(7) Uani 1 1 d . . .
H25 H -0.1529 0.0423 0.2043 0.065 Uiso 1 1 calc R . .
C26 C -0.09950(10) 0.1234(5) 0.2126(3) 0.0599(8) Uani 1 1 d . . .
H26 H -0.0976 0.1347 0.2882 0.072 Uiso 1 1 calc R . .
C27 C -0.04214(8) 0.1795(4) -0.0162(2) 0.0431(6) Uani 1 1 d . . .
H27 H -0.0437 0.1544 -0.0907 0.052 Uiso 1 1 calc R . .
N27 N -0.01254(6) 0.2435(3) 0.02796(17) 0.0390(5) Uani 1 1 d . . .
N31 N 0.48738(6) 0.3664(3) 0.23826(17) 0.0378(5) Uani 1 1 d . . .
C32 C 0.48513(7) 0.3407(4) 0.3427(2) 0.0387(5) Uani 1 1 d . . .
H32 H 0.4619 0.3236 0.3706 0.046 Uiso 1 1 calc R . .
C33 C 0.51573(7) 0.3380(3) 0.41221(19) 0.0356(5) Uani 1 1 d . . .
H33 H 0.5134 0.3212 0.4867 0.043 Uiso 1 1 calc R . .
C34 C 0.54973(6) 0.3601(3) 0.37131(17) 0.0300(4) Uani 1 1 d . . .
C35 C 0.55214(6) 0.3864(3) 0.26278(18) 0.0327(5) Uani 1 1 d . . .
H35 H 0.5751 0.4017 0.2327 0.039 Uiso 1 1 calc R . .
C36 C 0.52037(7) 0.3898(3) 0.19865(19) 0.0355(5) Uani 1 1 d . . .
H36 H 0.5219 0.4094 0.1241 0.043 Uiso 1 1 calc R . .
C37 C 0.58165(6) 0.3617(3) 0.45012(17) 0.0313(4) Uani 1 1 d . . .
N37 N 0.61382(5) 0.3085(3) 0.41184(15) 0.0309(4) Uani 1 1 d . . .
H37 H 0.6157(8) 0.265(4) 0.352(2) 0.037 Uiso 1 1 d . . .
O37 O 0.57813(5) 0.4125(3) 0.54257(13) 0.0409(4) Uani 1 1 d . . .
N41 N 0.73654(6) 0.1934(3) 0.46199(18) 0.0442(5) Uani 1 1 d . . .
C42 C 0.70698(6) 0.2460(3) 0.51342(18) 0.0331(5) Uani 1 1 d . . .
C43 C 0.70809(7) 0.2987(4) 0.62009(19) 0.0377(5) Uani 1 1 d . . .
H43 H 0.6866 0.3365 0.6528 0.045 Uiso 1 1 calc R . .
C44 C 0.74123(7) 0.2947(4) 0.6776(2) 0.0445(6) Uani 1 1 d . . .
H44 H 0.7430 0.3292 0.7508 0.053 Uiso 1 1 calc R . .
C45 C 0.77188(8) 0.2388(5) 0.6256(2) 0.0513(7) Uani 1 1 d . . .
H45 H 0.7949 0.2332 0.6632 0.062 Uiso 1 1 calc R . .
C46 C 0.76833(8) 0.1916(5) 0.5186(2) 0.0526(7) Uani 1 1 d . . .
H46 H 0.7895 0.1562 0.4837 0.063 Uiso 1 1 calc R . .
C47 C 0.67335(6) 0.2476(3) 0.44542(18) 0.0323(4) Uani 1 1 d . . .
H47 H 0.6734 0.2016 0.3745 0.039 Uiso 1 1 calc R . .
N47 N 0.64390(5) 0.3108(3) 0.48133(15) 0.0311(4) Uani 1 1 d . . .
C51 C 0.20133(7) 0.2673(5) -0.3660(2) 0.0493(7) Uani 1 1 d D . .
O51 O 0.19302(6) 0.4262(3) -0.3238(2) 0.0582(6) Uani 1 1 d D A .
H51 H 0.1761(12) 0.412(6) -0.286(4) 0.070 Uiso 1 1 d . . .
O52 O 0.18387(7) 0.1288(4) -0.3517(2) 0.0692(7) Uani 1 1 d D A .
C52A C 0.23326(9) 0.2773(5) -0.4391(3) 0.0498(8) Uani 0.886(2) 1 d PD A 1
H52A H 0.2397 0.1512 -0.4609 0.060 Uiso 0.886(2) 1 calc PR A 1
H52B H 0.2255 0.3462 -0.5045 0.060 Uiso 0.886(2) 1 calc PR A 1
C53A C 0.26664(9) 0.3679(5) -0.3879(3) 0.0459(7) Uani 0.886(2) 1 d PD A 1
H53A H 0.2859 0.3697 -0.4402 0.055 Uiso 0.886(2) 1 calc PR A 1
H53B H 0.2606 0.4970 -0.3713 0.055 Uiso 0.886(2) 1 calc PR A 1
C54A C 0.28150(9) 0.2763(5) -0.2872(2) 0.0467(7) Uani 0.886(2) 1 d PD A 1
H54A H 0.2853 0.1439 -0.3009 0.056 Uiso 0.886(2) 1 calc PR A 1
H54B H 0.2637 0.2878 -0.2310 0.056 Uiso 0.886(2) 1 calc PR A 1
C55A C 0.31774(9) 0.3645(5) -0.2484(2) 0.0438(7) Uani 0.886(2) 1 d PD A 1
H55A H 0.3365 0.3320 -0.2989 0.053 Uiso 0.886(2) 1 calc PR A 1
H55B H 0.3149 0.4997 -0.2498 0.053 Uiso 0.886(2) 1 calc PR A 1
C56A C 0.33090(10) 0.3070(6) -0.1376(3) 0.0417(9) Uani 0.886(2) 1 d PD A 1
H56A H 0.3310 0.1712 -0.1342 0.050 Uiso 0.886(2) 1 calc PR A 1
H56B H 0.3133 0.3515 -0.0863 0.050 Uiso 0.886(2) 1 calc PR A 1
C57A C 0.36858(8) 0.3768(4) -0.1025(2) 0.0351(6) Uani 0.886(2) 1 d PD A 1
H57A H 0.3694 0.5120 -0.1103 0.042 Uiso 0.886(2) 1 calc PR A 1
H57B H 0.3868 0.3231 -0.1487 0.042 Uiso 0.886(2) 1 calc PR A 1
C58A C 0.37789(7) 0.3251(4) 0.0134(2) 0.0325(5) Uani 0.886(2) 1 d PD A 1
H58A H 0.3610 0.3903 0.0593 0.039 Uiso 0.886(2) 1 calc PR A 1
H58B H 0.3737 0.1917 0.0221 0.039 Uiso 0.886(2) 1 calc PR A 1
C59A C 0.41629(15) 0.3682(19) 0.0526(3) 0.0341(12) Uani 0.886(2) 1 d PD A 1
O59A O 0.42187(6) 0.3363(3) 0.15597(16) 0.0405(5) Uani 0.886(2) 1 d PD A 1
H59A H 0.4441 0.3483 0.1732 0.049 Uiso 0.886(2) 1 calc PR A 1
O60A O 0.43963(6) 0.4236(4) -0.00478(19) 0.0460(6) Uani 0.886(2) 1 d PD A 1
C52B C 0.2390(4) 0.261(4) -0.3844(19) 0.0498(8) Uani 0.114(2) 1 d PD A 2
H52C H 0.2425 0.3229 -0.4534 0.060 Uiso 0.114(2) 1 calc PR A 2
H52D H 0.2455 0.1299 -0.3941 0.060 Uiso 0.114(2) 1 calc PR A 2
C53B C 0.2669(5) 0.343(4) -0.3018(18) 0.0459(7) Uani 0.114(2) 1 d PD A 2
H53C H 0.2629 0.4765 -0.2949 0.055 Uiso 0.114(2) 1 calc PR A 2
H53D H 0.2642 0.2852 -0.2310 0.055 Uiso 0.114(2) 1 calc PR A 2
C54B C 0.3052(4) 0.306(4) -0.3401(15) 0.0467(7) Uani 0.114(2) 1 d PD A 2
H54C H 0.3070 0.3570 -0.4128 0.056 Uiso 0.114(2) 1 calc PR A 2
H54D H 0.3091 0.1713 -0.3445 0.056 Uiso 0.114(2) 1 calc PR A 2
C55B C 0.3359(5) 0.392(3) -0.2633(14) 0.0438(7) Uani 0.114(2) 1 d PD A 2
H55C H 0.3601 0.3452 -0.2811 0.053 Uiso 0.114(2) 1 calc PR A 2
H55D H 0.3360 0.5278 -0.2708 0.053 Uiso 0.114(2) 1 calc PR A 2
C56B C 0.3276(7) 0.338(7) -0.1493(17) 0.0417(9) Uani 0.114(2) 1 d PD A 2
H56C H 0.3098 0.4302 -0.1259 0.050 Uiso 0.114(2) 1 calc PR A 2
H56D H 0.3143 0.2204 -0.1556 0.050 Uiso 0.114(2) 1 calc PR A 2
C57B C 0.3537(4) 0.316(3) -0.0603(13) 0.0351(6) Uani 0.114(2) 1 d PD A 2
H57C H 0.3561 0.1822 -0.0479 0.042 Uiso 0.114(2) 1 calc PR A 2
H57D H 0.3423 0.3673 0.0029 0.042 Uiso 0.114(2) 1 calc PR A 2
C58B C 0.3913(4) 0.391(3) -0.0581(15) 0.0325(5) Uani 0.114(2) 1 d PD A 2
H58C H 0.3899 0.5250 -0.0690 0.039 Uiso 0.114(2) 1 calc PR A 2
H58D H 0.4039 0.3378 -0.1189 0.039 Uiso 0.114(2) 1 calc PR A 2
C59B C 0.4145(9) 0.353(17) 0.045(3) 0.0341(12) Uani 0.114(2) 1 d PD A 2
O59B O 0.4041(5) 0.307(3) 0.1410(12) 0.0405(5) Uani 0.114(2) 1 d PD A 2
H59B H 0.4221 0.3117 0.1851 0.049 Uiso 0.114(2) 1 calc PR A 2
O60B O 0.4462(5) 0.399(3) 0.0354(15) 0.0460(6) Uani 0.114(2) 1 d PD 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
O1W H1A 0.87(5) . ?
O1W H1B 0.97(6) . ?
O2W H2A 0.90(3) . ?
O2W H2B 0.82(3) . ?
N11 C12 1.331(4) . ?
N11 C16 1.334(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 C17 1.502(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.228(3) . ?
C17 N17 1.346(3) . ?
N17 N27 1.379(3) . ?
N17 H17 0.81(4) . ?
N21 C26 1.338(4) . ?
N21 C22 1.360(4) . ?
C22 C23 1.357(4) . ?
C22 C27 1.465(4) . ?
C23 C24 1.365(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N27 1.284(3) . ?
C27 H27 0.9500 . ?
N31 C32 1.329(3) . ?
N31 C36 1.346(3) . ?
C32 C33 1.388(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(3) . ?
C34 C37 1.495(3) . ?
C35 C36 1.384(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 O37 1.230(3) . ?
C37 N37 1.357(3) . ?
N37 N47 1.373(2) . ?
N37 H37 0.82(3) . ?
N41 C46 1.336(3) . ?
N41 C42 1.349(3) . ?
C42 C43 1.389(3) . ?
C42 C47 1.466(3) . ?
C43 C44 1.385(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.392(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.384(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 N47 1.280(3) . ?
C47 H47 0.9500 . ?
C51 O52 1.214(4) . ?
C51 O51 1.314(4) . ?
C51 C52B 1.419(15) . ?
C51 C52A 1.529(4) . ?
O51 H51 0.81(4) . ?
C52A C53A 1.508(5) . ?
C52A H52A 0.9900 . ?
C52A H52B 0.9900 . ?
C53A C54A 1.505(5) . ?
C53A H53A 0.9900 . ?
C53A H53B 0.9900 . ?
C54A C55A 1.537(4) . ?
C54A H54A 0.9900 . ?
C54A H54B 0.9900 . ?
C55A C56A 1.505(4) . ?
C55A H55A 0.9900 . ?
C55A H55B 0.9900 . ?
C56A C57A 1.521(5) . ?
C56A H56A 0.9900 . ?
C56A H56B 0.9900 . ?
C57A C58A 1.523(4) . ?
C57A H57A 0.9900 . ?
C57A H57B 0.9900 . ?
C58A C59A 1.505(4) . ?
C58A H58A 0.9900 . ?
C58A H58B 0.9900 . ?
C59A O60A 1.217(4) . ?
C59A O59A 1.321(4) . ?
O59A H59A 0.8400 . ?
C52B C53B 1.541(17) . ?
C52B H52C 0.9900 . ?
C52B H52D 0.9900 . ?
C53B C54B 1.535(17) . ?
C53B H53C 0.9900 . ?
C53B H53D 0.9900 . ?
C54B C55B 1.578(16) . ?
C54B H54C 0.9900 . ?
C54B H54D 0.9900 . ?
C55B C56B 1.529(18) . ?
C55B H55C 0.9900 . ?
C55B H55D 0.9900 . ?
C56B C57B 1.444(15) . ?
C56B H56C 0.9900 . ?
C56B H56D 0.9900 . ?
C57B C58B 1.486(16) . ?
C57B H57C 0.9900 . ?
C57B H57D 0.9900 . ?
C58B C59B 1.536(18) . ?
C58B H58C 0.9900 . ?
C58B H58D 0.9900 . ?
C59B O60B 1.229(15) . ?
C59B O59B 1.323(16) . ?
O59B H59B 0.8400 . ?

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
H1A O1W H1B 102(5) . . ?
H2A O2W H2B 101(3) . . ?
C12 N11 C16 117.0(3) . . ?
N11 C12 C13 123.2(3) . . ?
N11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 117.2(3) . . ?
C15 C14 C17 124.5(2) . . ?
C13 C14 C17 118.3(2) . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N11 C16 C15 123.4(3) . . ?
N11 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
O17 C17 N17 123.3(3) . . ?
O17 C17 C14 120.4(2) . . ?
N17 C17 C14 116.3(2) . . ?
C17 N17 N27 117.2(2) . . ?
C17 N17 H17 124(2) . . ?
N27 N17 H17 118(2) . . ?
C26 N21 C22 118.6(3) . . ?
C23 C22 N21 122.2(3) . . ?
C23 C22 C27 117.0(3) . . ?
N21 C22 C27 120.7(2) . . ?
C22 C23 C24 118.3(3) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 117.4(3) . . ?
C24 C25 H25 121.3 . . ?
C26 C25 H25 121.3 . . ?
N21 C26 C25 122.1(3) . . ?
N21 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
N27 C27 C22 119.8(3) . . ?
N27 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C27 N27 N17 115.9(2) . . ?
C32 N31 C36 119.0(2) . . ?
N31 C32 C33 122.0(2) . . ?
N31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C34 C33 C32 119.0(2) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C35 C34 C33 119.1(2) . . ?
C35 C34 C37 124.1(2) . . ?
C33 C34 C37 116.75(19) . . ?
C34 C35 C36 118.6(2) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
N31 C36 C35 122.3(2) . . ?
N31 C36 H36 118.9 . . ?
C35 C36 H36 118.9 . . ?
O37 C37 N37 123.8(2) . . ?
O37 C37 C34 120.5(2) . . ?
N37 C37 C34 115.73(19) . . ?
C37 N37 N47 117.51(18) . . ?
C37 N37 H37 123(2) . . ?
N47 N37 H37 119(2) . . ?
C46 N41 C42 117.0(2) . . ?
N41 C42 C43 123.7(2) . . ?
N41 C42 C47 113.7(2) . . ?
C43 C42 C47 122.6(2) . . ?
C44 C43 C42 118.4(2) . . ?
C44 C43 H43 120.8 . . ?
C42 C43 H43 120.8 . . ?
C43 C44 C45 118.4(2) . . ?
C43 C44 H44 120.8 . . ?
C45 C44 H44 120.8 . . ?
C46 C45 C44 119.2(2) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
N41 C46 C45 123.3(3) . . ?
N41 C46 H46 118.4 . . ?
C45 C46 H46 118.4 . . ?
N47 C47 C42 120.2(2) . . ?
N47 C47 H47 119.9 . . ?
C42 C47 H47 119.9 . . ?
C47 N47 N37 116.23(19) . . ?
O52 C51 O51 122.4(3) . . ?
O52 C51 C52B 121.6(13) . . ?
O51 C51 C52B 110.2(12) . . ?
O52 C51 C52A 123.8(3) . . ?
O51 C51 C52A 113.6(3) . . ?
C52B C51 C52A 27.8(10) . . ?
C51 O51 H51 109(3) . . ?
C53A C52A C51 113.6(3) . . ?
C53A C52A H52A 108.8 . . ?
C51 C52A H52A 108.8 . . ?
C53A C52A H52B 108.8 . . ?
C51 C52A H52B 108.8 . . ?
H52A C52A H52B 107.7 . . ?
C54A C53A C52A 114.5(3) . . ?
C54A C53A H53A 108.6 . . ?
C52A C53A H53A 108.6 . . ?
C54A C53A H53B 108.6 . . ?
C52A C53A H53B 108.6 . . ?
H53A C53A H53B 107.6 . . ?
C53A C54A C55A 110.6(3) . . ?
C53A C54A H54A 109.5 . . ?
C55A C54A H54A 109.5 . . ?
C53A C54A H54B 109.5 . . ?
C55A C54A H54B 109.5 . . ?
H54A C54A H54B 108.1 . . ?
C56A C55A C54A 114.1(3) . . ?
C56A C55A H55A 108.7 . . ?
C54A C55A H55A 108.7 . . ?
C56A C55A H55B 108.7 . . ?
C54A C55A H55B 108.7 . . ?
H55A C55A H55B 107.6 . . ?
C55A C56A C57A 114.8(3) . . ?
C55A C56A H56A 108.6 . . ?
C57A C56A H56A 108.6 . . ?
C55A C56A H56B 108.6 . . ?
C57A C56A H56B 108.6 . . ?
H56A C56A H56B 107.6 . . ?
C56A C57A C58A 110.5(3) . . ?
C56A C57A H57A 109.5 . . ?
C58A C57A H57A 109.5 . . ?
C56A C57A H57B 109.5 . . ?
C58A C57A H57B 109.5 . . ?
H57A C57A H57B 108.1 . . ?
C59A C58A C57A 114.9(3) . . ?
C59A C58A H58A 108.5 . . ?
C57A C58A H58A 108.5 . . ?
C59A C58A H58B 108.5 . . ?
C57A C58A H58B 108.5 . . ?
H58A C58A H58B 107.5 . . ?
O60A C59A O59A 124.0(3) . . ?
O60A C59A C58A 123.8(3) . . ?
O59A C59A C58A 112.2(3) . . ?
C59A O59A H59A 109.5 . . ?
C51 C52B C53B 120.0(16) . . ?
C51 C52B H52C 107.3 . . ?
C53B C52B H52C 107.3 . . ?
C51 C52B H52D 107.3 . . ?
C53B C52B H52D 107.3 . . ?
H52C C52B H52D 106.9 . . ?
C54B C53B C52B 108.1(13) . . ?
C54B C53B H53C 110.1 . . ?
C52B C53B H53C 110.1 . . ?
C54B C53B H53D 110.1 . . ?
C52B C53B H53D 110.1 . . ?
H53C C53B H53D 108.4 . . ?
C53B C54B C55B 112.2(14) . . ?
C53B C54B H54C 109.2 . . ?
C55B C54B H54C 109.2 . . ?
C53B C54B H54D 109.2 . . ?
C55B C54B H54D 109.2 . . ?
H54C C54B H54D 107.9 . . ?
C56B C55B C54B 107.2(14) . . ?
C56B C55B H55C 110.3 . . ?
C54B C55B H55C 110.3 . . ?
C56B C55B H55D 110.3 . . ?
C54B C55B H55D 110.3 . . ?
H55C C55B H55D 108.5 . . ?
C57B C56B C55B 126.4(18) . . ?
C57B C56B H56C 105.7 . . ?
C55B C56B H56C 105.7 . . ?
C57B C56B H56D 105.7 . . ?
C55B C56B H56D 105.7 . . ?
H56C C56B H56D 106.2 . . ?
C56B C57B C58B 123.8(15) . . ?
C56B C57B H57C 106.4 . . ?
C58B C57B H57C 106.4 . . ?
C56B C57B H57D 106.4 . . ?
C58B C57B H57D 106.4 . . ?
H57C C57B H57D 106.5 . . ?
C57B C58B C59B 115.2(15) . . ?
C57B C58B H58C 108.5 . . ?
C59B C58B H58C 108.5 . . ?
C57B C58B H58D 108.5 . . ?
C59B C58B H58D 108.5 . . ?
H58C C58B H58D 107.5 . . ?
O60B C59B O59B 118.6(18) . . ?
O60B C59B C58B 110.9(19) . . ?
O59B C59B C58B 130(2) . . ?
C59B O59B H59B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -1.6(5) . . . . ?
N11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C12 C13 C14 C17 179.4(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C17 C14 C15 C16 -179.4(3) . . . . ?
C12 N11 C16 C15 1.6(5) . . . . ?
C14 C15 C16 N11 -1.3(5) . . . . ?
C15 C14 C17 O17 -169.9(3) . . . . ?
C13 C14 C17 O17 10.0(4) . . . . ?
C15 C14 C17 N17 10.5(4) . . . . ?
C13 C14 C17 N17 -169.6(2) . . . . ?
O17 C17 N17 N27 -0.6(4) . . . . ?
C14 C17 N17 N27 179.0(2) . . . . ?
C26 N21 C22 C23 -0.4(4) . . . . ?
C26 N21 C22 C27 -178.8(3) . . . . ?
N21 C22 C23 C24 0.7(5) . . . . ?
C27 C22 C23 C24 179.2(3) . . . . ?
C22 C23 C24 C25 -1.6(5) . . . . ?
C23 C24 C25 C26 2.1(5) . . . . ?
C22 N21 C26 C25 0.9(5) . . . . ?
C24 C25 C26 N21 -1.7(5) . . . . ?
C23 C22 C27 N27 173.5(3) . . . . ?
N21 C22 C27 N27 -8.1(4) . . . . ?
C22 C27 N27 N17 179.0(2) . . . . ?
C17 N17 N27 C27 178.0(2) . . . . ?
C36 N31 C32 C33 0.3(4) . . . . ?
N31 C32 C33 C34 -1.0(4) . . . . ?
C32 C33 C34 C35 0.7(3) . . . . ?
C32 C33 C34 C37 178.2(2) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C37 C34 C35 C36 -177.2(2) . . . . ?
C32 N31 C36 C35 0.6(4) . . . . ?
C34 C35 C36 N31 -0.8(4) . . . . ?
C35 C34 C37 O37 149.9(2) . . . . ?
C33 C34 C37 O37 -27.4(3) . . . . ?
C35 C34 C37 N37 -28.6(3) . . . . ?
C33 C34 C37 N37 154.0(2) . . . . ?
O37 C37 N37 N47 0.5(3) . . . . ?
C34 C37 N37 N47 179.02(19) . . . . ?
C46 N41 C42 C43 0.5(4) . . . . ?
C46 N41 C42 C47 178.9(2) . . . . ?
N41 C42 C43 C44 -0.9(4) . . . . ?
C47 C42 C43 C44 -179.2(2) . . . . ?
C42 C43 C44 C45 0.3(4) . . . . ?
C43 C44 C45 C46 0.8(5) . . . . ?
C42 N41 C46 C45 0.6(5) . . . . ?
C44 C45 C46 N41 -1.3(5) . . . . ?
N41 C42 C47 N47 -173.6(2) . . . . ?
C43 C42 C47 N47 4.9(4) . . . . ?
C42 C47 N47 N37 179.4(2) . . . . ?
C37 N37 N47 C47 175.2(2) . . . . ?
O52 C51 C52A C53A -131.4(3) . . . . ?
O51 C51 C52A C53A 52.1(4) . . . . ?
C52B C51 C52A C53A -37(3) . . . . ?
C51 C52A C53A C54A 58.7(4) . . . . ?
C52A C53A C54A C55A 173.5(3) . . . . ?
C53A C54A C55A C56A 168.8(3) . . . . ?
C54A C55A C56A C57A 173.8(3) . . . . ?
C55A C56A C57A C58A 175.1(3) . . . . ?
C56A C57A C58A C59A 173.2(7) . . . . ?
C57A C58A C59A O60A -6.8(15) . . . . ?
C57A C58A C59A O59A 174.1(7) . . . . ?
O52 C51 C52B C53B -114(2) . . . . ?
O51 C51 C52B C53B 40(3) . . . . ?
C52A C51 C52B C53B 142(5) . . . . ?
C51 C52B C53B C54B 177(2) . . . . ?
C52B C53B C54B C55B 177(2) . . . . ?
C53B C54B C55B C56B 48(3) . . . . ?
C54B C55B C56B C57B 152(4) . . . . ?
C55B C56B C57B C58B 17(6) . . . . ?
C56B C57B C58B C59B 179(6) . . . . ?
C57B C58B C59B O60B 172(6) . . . . ?
C57B C58B C59B O59B -19(14) . . . . ?

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
N17 H17 O1W 0.81(4) 2.08(4) 2.844(4) 158(3) .
N37 H37 O2W 0.82(3) 2.03(3) 2.832(3) 163(3) .
O51 H51 N11 0.81(4) 1.88(4) 2.685(4) 173(4) .
O59A H59A N31 0.84 1.76 2.582(3) 167.2 .
O59B H59B N31 0.84 2.49 3.267(18) 153.9 .
O1W H1A O17 0.87(5) 2.05(5) 2.860(4) 155(5) 4_565
O1W H1B N21 0.97(6) 2.50(5) 3.216(5) 130(4) 4_565
O2W H2A O37 0.90(3) 1.95(3) 2.805(2) 157(3) 4_565
O2W H2B O59A 0.82(3) 2.11(4) 2.916(3) 168(3) 2_645

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        31.56
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.123
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23Mal
_database_code_depnum_ccdc_archive 'CCDC 1478927'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EK-A-Mal (2-pyridyl)-CONH-N=CH-(3-pyridyl), HOOC-(CH2)1-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H10 N4 O) (C3 H4 O4)
;
_chemical_formula_sum            'C15 H14 N4 O5'
_chemical_formula_weight         330.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.0953(12)
_cell_length_b                   9.9439(14)
_cell_length_c                   10.1459(15)
_cell_angle_alpha                99.924(6)
_cell_angle_beta                 106.674(6)
_cell_angle_gamma                100.865(6)
_cell_volume                     745.78(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6918
_cell_measurement_theta_min      4.67
_cell_measurement_theta_max      68.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7493
_exptl_absorpt_correction_T_max  0.8466
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            11844
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         68.55
_reflns_number_total             2638
_reflns_number_gt                2360
_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)+(0.0700P)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         2638
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 -0.00282(16) 0.07872(13) 0.33298(13) 0.0217(3) Uani 1 1 d . . .
C12 C 0.15141(19) 0.05891(15) 0.41176(14) 0.0201(3) Uani 1 1 d . . .
C13 C 0.1955(2) -0.07074(16) 0.39912(15) 0.0241(3) Uani 1 1 d . . .
H13A H 0.3072 -0.0791 0.4559 0.029 Uiso 1 1 calc R . .
C14 C 0.0709(2) -0.18775(16) 0.30071(16) 0.0267(3) Uani 1 1 d . . .
H14A H 0.0952 -0.2781 0.2899 0.032 Uiso 1 1 calc R . .
C15 C -0.0898(2) -0.16959(16) 0.21869(16) 0.0263(3) Uani 1 1 d . . .
H15A H -0.1775 -0.2473 0.1511 0.032 Uiso 1 1 calc R . .
C16 C -0.11952(19) -0.03499(16) 0.23767(16) 0.0239(3) Uani 1 1 d . . .
H16A H -0.2285 -0.0231 0.1799 0.029 Uiso 1 1 calc R . .
C17 C 0.28353(19) 0.18662(15) 0.51702(15) 0.0206(3) Uani 1 1 d . . .
N17 N 0.23743(16) 0.31055(13) 0.50967(13) 0.0213(3) Uani 1 1 d . . .
H17 H 0.140(2) 0.3115(18) 0.4398(19) 0.026 Uiso 1 1 d . . .
O17 O 0.42219(14) 0.17686(11) 0.60214(11) 0.0269(3) Uani 1 1 d . . .
N21 N 0.74769(16) 0.79138(13) 0.83877(12) 0.0209(3) Uani 1 1 d . . .
C22 C 0.62228(19) 0.67639(15) 0.75488(15) 0.0203(3) Uani 1 1 d . . .
H22A H 0.6536 0.5888 0.7419 0.024 Uiso 1 1 calc R . .
C23 C 0.44703(19) 0.67954(15) 0.68543(14) 0.0200(3) Uani 1 1 d . . .
C24 C 0.40319(19) 0.80947(16) 0.70632(15) 0.0230(3) Uani 1 1 d . . .
H24A H 0.2857 0.8162 0.6615 0.028 Uiso 1 1 calc R . .
C25 C 0.5350(2) 0.92926(15) 0.79416(16) 0.0245(3) Uani 1 1 d . . .
H25A H 0.5079 1.0184 0.8092 0.029 Uiso 1 1 calc R . .
C26 C 0.7052(2) 0.91658(15) 0.85891(15) 0.0229(3) Uani 1 1 d . . .
H26A H 0.7941 0.9979 0.9189 0.027 Uiso 1 1 calc R . .
C27 C 0.31624(18) 0.54898(15) 0.59190(15) 0.0209(3) Uani 1 1 d . . .
H27A H 0.2057 0.5520 0.5284 0.025 Uiso 1 1 calc R . .
N27 N 0.35745(16) 0.43172(13) 0.59961(12) 0.0214(3) Uani 1 1 d . . .
C31 C 1.07133(18) 0.62993(15) 0.84962(15) 0.0208(3) Uani 1 1 d . . .
O31 O 1.04311(14) 0.72736(11) 0.93869(11) 0.0268(3) Uani 1 1 d . . .
H31 H 0.929(3) 0.7565(19) 0.8980(19) 0.032 Uiso 1 1 d . . .
O32 O 0.99416(14) 0.59304(11) 0.72083(11) 0.0261(3) Uani 1 1 d . . .
C32 C 1.20804(19) 0.55481(15) 0.92059(15) 0.0222(3) Uani 1 1 d . . .
H32A H 1.1460 0.4743 0.9483 0.027 Uiso 1 1 calc R . .
H32B H 1.2621 0.5166 0.8511 0.027 Uiso 1 1 calc R . .
C33 C 1.35538(19) 0.65073(15) 1.05104(15) 0.0223(3) Uani 1 1 d . . .
O33 O 1.32981(14) 0.63498(11) 1.17170(11) 0.0268(3) Uani 1 1 d . . .
H33 H 1.426(3) 0.694(2) 1.250(2) 0.032 Uiso 1 1 d . . .
O34 O 1.48241(15) 0.73308(13) 1.04453(12) 0.0376(3) Uani 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 1.3425(19) . ?
N11 C12 1.3457(19) . ?
C12 C13 1.396(2) . ?
C12 C17 1.504(2) . ?
C13 C14 1.396(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.392(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.395(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O17 1.2365(18) . ?
C17 N17 1.3611(19) . ?
N17 N27 1.3782(17) . ?
N17 H17 0.899(19) . ?
N21 C22 1.3393(19) . ?
N21 C26 1.3506(19) . ?
C22 C23 1.400(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.401(2) . ?
C23 C27 1.479(2) . ?
C24 C25 1.400(2) . ?
C24 H24A 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 N27 1.2806(19) . ?
C27 H27A 0.9500 . ?
C31 O32 1.2298(18) . ?
C31 O31 1.3067(18) . ?
C31 C32 1.5300(19) . ?
O31 H31 1.018(19) . ?
C32 C33 1.5212(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 O34 1.2135(19) . ?
C33 O33 1.3286(18) . ?
O33 H33 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 116.73(12) . . ?
N11 C12 C13 124.03(13) . . ?
N11 C12 C17 116.81(12) . . ?
C13 C12 C17 119.15(13) . . ?
C14 C13 C12 118.12(13) . . ?
C14 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
C15 C14 C13 118.72(14) . . ?
C15 C14 H14A 120.6 . . ?
C13 C14 H14A 120.6 . . ?
C14 C15 C16 118.66(14) . . ?
C14 C15 H15A 120.7 . . ?
C16 C15 H15A 120.7 . . ?
N11 C16 C15 123.72(13) . . ?
N11 C16 H16A 118.1 . . ?
C15 C16 H16A 118.1 . . ?
O17 C17 N17 123.90(14) . . ?
O17 C17 C12 121.45(13) . . ?
N17 C17 C12 114.65(12) . . ?
C17 N17 N27 117.06(12) . . ?
C17 N17 H17 119.4(11) . . ?
N27 N17 H17 123.0(11) . . ?
C22 N21 C26 119.32(12) . . ?
N21 C22 C23 122.89(13) . . ?
N21 C22 H22A 118.6 . . ?
C23 C22 H22A 118.6 . . ?
C22 C23 C24 117.73(13) . . ?
C22 C23 C27 120.02(13) . . ?
C24 C23 C27 122.24(13) . . ?
C25 C24 C23 119.08(13) . . ?
C25 C24 H24A 120.5 . . ?
C23 C24 H24A 120.5 . . ?
C26 C25 C24 119.39(13) . . ?
C26 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
N21 C26 C25 121.60(13) . . ?
N21 C26 H26A 119.2 . . ?
C25 C26 H26A 119.2 . . ?
N27 C27 C23 117.57(12) . . ?
N27 C27 H27A 121.2 . . ?
C23 C27 H27A 121.2 . . ?
C27 N27 N17 117.45(12) . . ?
O32 C31 O31 125.96(13) . . ?
O32 C31 C32 120.27(13) . . ?
O31 C31 C32 113.70(12) . . ?
C31 O31 H31 113.9(11) . . ?
C33 C32 C31 113.15(11) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.8 . . ?
O34 C33 O33 123.90(14) . . ?
O34 C33 C32 123.07(13) . . ?
O33 C33 C32 113.02(12) . . ?
C33 O33 H33 110.5(11) . . ?

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 0.4(2) . . . . ?
C16 N11 C12 C17 179.07(12) . . . . ?
N11 C12 C13 C14 -1.3(2) . . . . ?
C17 C12 C13 C14 -179.98(13) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C12 N11 C16 C15 1.0(2) . . . . ?
C14 C15 C16 N11 -1.3(2) . . . . ?
N11 C12 C17 O17 173.88(13) . . . . ?
C13 C12 C17 O17 -7.3(2) . . . . ?
N11 C12 C17 N17 -6.25(19) . . . . ?
C13 C12 C17 N17 172.54(12) . . . . ?
O17 C17 N17 N27 2.6(2) . . . . ?
C12 C17 N17 N27 -177.26(11) . . . . ?
C26 N21 C22 C23 0.3(2) . . . . ?
N21 C22 C23 C24 -0.3(2) . . . . ?
N21 C22 C23 C27 178.72(12) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C27 C23 C24 C25 -178.70(13) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
C22 N21 C26 C25 -0.4(2) . . . . ?
C24 C25 C26 N21 0.4(2) . . . . ?
C22 C23 C27 N27 13.8(2) . . . . ?
C24 C23 C27 N27 -167.27(13) . . . . ?
C23 C27 N27 N17 -178.31(11) . . . . ?
C17 N17 N27 C27 179.00(12) . . . . ?
O32 C31 C32 C33 149.20(14) . . . . ?
O31 C31 C32 C33 -33.67(17) . . . . ?
C31 C32 C33 O34 -80.06(18) . . . . ?
C31 C32 C33 O33 99.75(14) . . . . ?

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
N17 H17 O32 0.899(19) 2.155(18) 2.9727(16) 150.9(15) 2_666
O31 H31 N21 1.018(19) 1.544(19) 2.5608(15) 175.9(16) .
O33 H33 O17 0.95(2) 1.76(2) 2.6940(15) 169.6(17) 2_767

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.058
