# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1550970'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (1R*,2S*)-{2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinecarbonyl}cyclohexanecarboxylic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N5 O3'
_chemical_formula_sum            'C19 H21 N5 O3'
_chemical_formula_weight         367.41

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.5960(10)
_cell_length_b                   12.3370(12)
_cell_length_c                   13.722(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.789(13)
_cell_angle_gamma                90.00
_cell_volume                     1749.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4339
_cell_measurement_theta_min      3.2670
_cell_measurement_theta_max      32.7769

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_min  0.94481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13893
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4000
_reflns_number_gt                2446
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0464P)²] 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         3996
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
C1 C 0.6609(2) 0.58383(17) 0.10051(16) 0.0180(5) Uani 1 1 d . . .
C2 C 0.3341(2) 0.57699(16) 0.11293(16) 0.0178(5) Uani 1 1 d . . .
C3 C 0.2715(2) 0.72497(17) -0.02028(16) 0.0188(5) Uani 1 1 d . . .
C4 C 0.1674(2) 0.76027(18) -0.09471(17) 0.0232(5) Uani 1 1 d . . .
H4 H 0.0910 0.7206 -0.1103 0.028 Uiso 1 1 calc R . .
C5 C 0.1803(2) 0.85497(18) -0.14450(17) 0.0258(5) Uani 1 1 d . . .
H5 H 0.1122 0.8807 -0.1939 0.031 Uiso 1 1 calc R . .
C6 C 0.2959(2) 0.91171(18) -0.12030(18) 0.0264(6) Uani 1 1 d . . .
H6 H 0.3068 0.9763 -0.1524 0.032 Uiso 1 1 calc R . .
C7 C 0.3931(2) 0.87014(17) -0.04817(18) 0.0260(6) Uani 1 1 d . . .
H7 H 0.4713 0.9074 -0.0331 0.031 Uiso 1 1 calc R . .
C8 C 0.2559(2) 0.51902(16) 0.17566(16) 0.0179(5) Uani 1 1 d . . .
C9 C 0.3139(2) 0.46451(17) 0.26205(17) 0.0227(5) Uani 1 1 d . . .
H9 H 0.4035 0.4616 0.2827 0.027 Uiso 1 1 calc R . .
C10 C 0.2362(2) 0.41445(18) 0.31713(18) 0.0263(5) Uani 1 1 d . . .
H10 H 0.2730 0.3782 0.3760 0.032 Uiso 1 1 calc R . .
C11 C 0.1035(2) 0.41881(18) 0.28391(18) 0.0258(5) Uani 1 1 d . . .
H11 H 0.0492 0.3854 0.3196 0.031 Uiso 1 1 calc R . .
C12 C 0.0533(2) 0.47398(17) 0.19644(17) 0.0233(5) Uani 1 1 d . . .
H12 H -0.0361 0.4767 0.1739 0.028 Uiso 1 1 calc R . .
C13 C 0.7467(2) 0.65107(17) 0.04847(16) 0.0197(5) Uani 1 1 d . . .
H13 H 0.7968 0.5982 0.0194 0.024 Uiso 1 1 calc R . .
C14 C 0.8478(2) 0.71570(17) 0.12442(17) 0.0211(5) Uani 1 1 d . . .
H14 H 0.8965 0.6641 0.1728 0.025 Uiso 1 1 calc R . .
C15 C 0.9432(2) 0.76883(18) 0.06938(18) 0.0264(6) Uani 1 1 d . . .
H151 H 1.0058 0.8111 0.1165 0.032 Uiso 1 1 calc R . .
H152 H 0.9897 0.7127 0.0423 0.032 Uiso 1 1 calc R . .
C16 C 0.8749(2) 0.84201(18) -0.01500(18) 0.0285(6) Uani 1 1 d . . .
H161 H 0.9378 0.8735 -0.0483 0.034 Uiso 1 1 calc R . .
H162 H 0.8319 0.9006 0.0120 0.034 Uiso 1 1 calc R . .
C17 C 0.7754(2) 0.77708(19) -0.09002(18) 0.0285(6) Uani 1 1 d . . .
H171 H 0.8196 0.7229 -0.1215 0.034 Uiso 1 1 calc R . .
H172 H 0.7294 0.8252 -0.1418 0.034 Uiso 1 1 calc R . .
C18 C 0.6786(2) 0.72113(18) -0.03884(17) 0.0243(5) Uani 1 1 d . . .
H181 H 0.6268 0.7756 -0.0148 0.029 Uiso 1 1 calc R . .
H182 H 0.6207 0.6762 -0.0871 0.029 Uiso 1 1 calc R . .
C19 C 0.7899(2) 0.80076(17) 0.18238(17) 0.0215(5) Uani 1 1 d . . .
N1 N 0.53523(17) 0.61075(15) 0.08209(14) 0.0188(4) Uani 1 1 d . . .
N2 N 0.45696(17) 0.56201(13) 0.13828(14) 0.0193(4) Uani 1 1 d . . .
N3 N 0.25554(19) 0.63254(15) 0.03404(14) 0.0218(4) Uani 1 1 d . . .
N4 N 0.38316(17) 0.77807(14) 0.00303(14) 0.0217(4) Uani 1 1 d . . .
N5 N 0.12701(17) 0.52399(14) 0.14214(14) 0.0213(4) Uani 1 1 d . . .
O1 O 0.70974(14) 0.50763(12) 0.15530(11) 0.0232(4) Uani 1 1 d . . .
O2 O 0.88254(15) 0.85161(13) 0.24778(13) 0.0284(4) Uani 1 1 d . . .
O3 O 0.67635(15) 0.82076(12) 0.17053(12) 0.0260(4) Uani 1 1 d . . .
H1N H 0.504(2) 0.673(2) 0.0485(19) 0.043(8) Uiso 1 1 d . . .
H2O H 0.851(3) 0.908(3) 0.284(2) 0.080(11) Uiso 1 1 d . . .
H3N H 0.177(2) 0.6169(18) 0.0301(16) 0.020(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.243(2) . ?
C1 N1 1.341(3) . ?
C1 C13 1.521(3) . ?
C2 N2 1.285(3) . ?
C2 N3 1.391(3) . ?
C2 C8 1.501(3) . ?
C3 N4 1.328(3) . ?
C3 N3 1.393(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(3) . ?
C6 H6 0.9300 . ?
C7 N4 1.352(3) . ?
C7 H7 0.9300 . ?
C8 N5 1.343(3) . ?
C8 C9 1.383(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 N5 1.343(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.524(3) . ?
C13 C14 1.541(3) . ?
C13 H13 0.9800 . ?
C14 C19 1.525(3) . ?
C14 C15 1.536(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.519(3) . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C16 C17 1.527(3) . ?
C16 H161 0.9700 . ?
C16 H162 0.9700 . ?
C17 C18 1.531(3) . ?
C17 H171 0.9700 . ?
C17 H172 0.9700 . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C19 O3 1.204(2) . ?
C19 O2 1.331(3) . ?
N1 N2 1.388(2) . ?
N1 H1N 0.92(3) . ?
N3 H3N 0.85(2) . ?
O2 H2O 0.96(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
O1 C1 N1 124.38(19) . . ?
O1 C1 C13 118.97(19) . . ?
N1 C1 C13 116.64(19) . . ?
N2 C2 N3 132.6(2) . . ?
N2 C2 C8 115.52(19) . . ?
N3 C2 C8 111.73(18) . . ?
N4 C3 N3 118.8(2) . . ?
N4 C3 C4 122.6(2) . . ?
N3 C3 C4 118.5(2) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 118.0(2) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N4 C7 C6 124.1(2) . . ?
N4 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?
N5 C8 C9 122.73(19) . . ?
N5 C8 C2 115.47(19) . . ?
C9 C8 C2 121.79(19) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N5 C12 C11 123.3(2) . . ?
N5 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C1 C13 C18 116.75(18) . . ?
C1 C13 C14 111.29(17) . . ?
C18 C13 C14 112.08(18) . . ?
C1 C13 H13 105.2 . . ?
C18 C13 H13 105.2 . . ?
C14 C13 H13 105.2 . . ?
C19 C14 C15 110.32(18) . . ?
C19 C14 C13 114.12(18) . . ?
C15 C14 C13 108.83(18) . . ?
C19 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C16 C15 C14 111.98(18) . . ?
C16 C15 H151 109.2 . . ?
C14 C15 H151 109.2 . . ?
C16 C15 H152 109.2 . . ?
C14 C15 H152 109.2 . . ?
H151 C15 H152 107.9 . . ?
C15 C16 C17 110.08(18) . . ?
C15 C16 H161 109.6 . . ?
C17 C16 H161 109.6 . . ?
C15 C16 H162 109.6 . . ?
C17 C16 H162 109.6 . . ?
H161 C16 H162 108.2 . . ?
C16 C17 C18 111.10(19) . . ?
C16 C17 H171 109.4 . . ?
C18 C17 H171 109.4 . . ?
C16 C17 H172 109.4 . . ?
C18 C17 H172 109.4 . . ?
H171 C17 H172 108.0 . . ?
C13 C18 C17 111.55(18) . . ?
C13 C18 H181 109.3 . . ?
C17 C18 H181 109.3 . . ?
C13 C18 H182 109.3 . . ?
C17 C18 H182 109.3 . . ?
H181 C18 H182 108.0 . . ?
O3 C19 O2 124.1(2) . . ?
O3 C19 C14 125.2(2) . . ?
O2 C19 C14 110.73(19) . . ?
C1 N1 N2 118.58(18) . . ?
C1 N1 H1N 122.4(16) . . ?
N2 N1 H1N 116.4(16) . . ?
C2 N2 N1 118.80(18) . . ?
C2 N3 C3 134.2(2) . . ?
C2 N3 H3N 110.4(15) . . ?
C3 N3 H3N 112.7(15) . . ?
C3 N4 C7 117.19(19) . . ?
C8 N5 C12 117.48(19) . . ?
C19 O2 H2O 113.8(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
N4 C3 C4 C5 -1.3(3) . . . . ?
N3 C3 C4 C5 176.3(2) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 N4 -1.5(3) . . . . ?
N2 C2 C8 N5 -172.30(18) . . . . ?
N3 C2 C8 N5 4.4(3) . . . . ?
N2 C2 C8 C9 7.7(3) . . . . ?
N3 C2 C8 C9 -175.57(19) . . . . ?
N5 C8 C9 C10 -1.0(3) . . . . ?
C2 C8 C9 C10 178.9(2) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 N5 -0.2(3) . . . . ?
O1 C1 C13 C18 163.30(19) . . . . ?
N1 C1 C13 C18 -15.6(3) . . . . ?
O1 C1 C13 C14 -66.3(2) . . . . ?
N1 C1 C13 C14 114.8(2) . . . . ?
C1 C13 C14 C19 -64.2(2) . . . . ?
C18 C13 C14 C19 68.5(2) . . . . ?
C1 C13 C14 C15 172.07(17) . . . . ?
C18 C13 C14 C15 -55.1(2) . . . . ?
C19 C14 C15 C16 -68.4(2) . . . . ?
C13 C14 C15 C16 57.5(2) . . . . ?
C14 C15 C16 C17 -58.8(2) . . . . ?
C15 C16 C17 C18 56.3(2) . . . . ?
C1 C13 C18 C17 -175.22(19) . . . . ?
C14 C13 C18 C17 54.7(2) . . . . ?
C16 C17 C18 C13 -54.7(3) . . . . ?
C15 C14 C19 O3 120.8(2) . . . . ?
C13 C14 C19 O3 -2.1(3) . . . . ?
C15 C14 C19 O2 -58.4(2) . . . . ?
C13 C14 C19 O2 178.72(17) . . . . ?
O1 C1 N1 N2 10.0(3) . . . . ?
C13 C1 N1 N2 -171.12(17) . . . . ?
N3 C2 N2 N1 2.5(3) . . . . ?
C8 C2 N2 N1 178.33(17) . . . . ?
C1 N1 N2 C2 -171.42(19) . . . . ?
N2 C2 N3 C3 -32.4(4) . . . . ?
C8 C2 N3 C3 151.7(2) . . . . ?
N4 C3 N3 C2 -0.4(4) . . . . ?
C4 C3 N3 C2 -178.0(2) . . . . ?
N3 C3 N4 C7 -177.04(19) . . . . ?
C4 C3 N4 C7 0.5(3) . . . . ?
C6 C7 N4 C3 0.9(3) . . . . ?
C9 C8 N5 C12 0.5(3) . . . . ?
C2 C8 N5 C12 -179.46(19) . . . . ?
C11 C12 N5 C8 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.250
_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_3
_database_code_depnum_ccdc_archive 'CCDC 1550973'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 2-{2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinecarbonyl}nicotinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N6 O3'
_chemical_formula_sum            'C18 H14 N6 O3'
_chemical_formula_weight         362.35

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.2194(6)
_cell_length_b                   10.2234(5)
_cell_length_c                   17.0821(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.026(5)
_cell_angle_gamma                90.00
_cell_volume                     1590.11(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3076
_cell_measurement_theta_min      2.9898
_cell_measurement_theta_max      32.1926

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_min  0.92552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12728
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3634
_reflns_number_gt                2145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0298P)²] 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         3634
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_restrained_S_all      0.802
_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
C1 C 0.90304(16) 0.57129(15) 0.11869(9) 0.0170(3) Uani 1 1 d . . .
C2 C 0.99431(16) 0.77080(14) -0.03154(9) 0.0150(3) Uani 1 1 d . . .
C3 C 0.79658(16) 0.67455(14) -0.13951(9) 0.0159(3) Uani 1 1 d . . .
C4 C 0.72555(16) 0.70365(15) -0.21571(9) 0.0179(4) Uani 1 1 d . . .
H4 H 0.7449 0.7812 -0.2406 0.021 Uiso 1 1 calc R . .
C5 C 0.62642(16) 0.61510(15) -0.25312(9) 0.0186(4) Uani 1 1 d . . .
H5 H 0.5783 0.6314 -0.3042 0.022 Uiso 1 1 calc R . .
C6 C 0.59842(17) 0.50106(14) -0.21422(9) 0.0184(3) Uani 1 1 d . . .
H6 H 0.5310 0.4400 -0.2383 0.022 Uiso 1 1 calc R . .
C7 C 0.67285(17) 0.48076(14) -0.13923(9) 0.0203(4) Uani 1 1 d . . .
H7 H 0.6539 0.4045 -0.1129 0.024 Uiso 1 1 calc R . .
C8 C 1.10747(16) 0.87574(14) -0.03212(9) 0.0150(3) Uani 1 1 d . . .
C9 C 1.21796(16) 0.89543(15) 0.03190(9) 0.0179(4) Uani 1 1 d . . .
H9 H 1.2246 0.8429 0.0768 0.021 Uiso 1 1 calc R . .
C10 C 1.31747(17) 0.99447(15) 0.02750(9) 0.0208(4) Uani 1 1 d . . .
H10 H 1.3927 1.0098 0.0695 0.025 Uiso 1 1 calc R . .
C11 C 1.30442(16) 1.07086(15) -0.03998(9) 0.0204(4) Uani 1 1 d . . .
H11 H 1.3706 1.1382 -0.0443 0.024 Uiso 1 1 calc R . .
C12 C 1.19128(16) 1.04503(15) -0.10063(9) 0.0194(4) Uani 1 1 d . . .
H12 H 1.1823 1.0969 -0.1459 0.023 Uiso 1 1 calc R . .
C13 C 0.79991(16) 0.45935(14) 0.12634(9) 0.0165(3) Uani 1 1 d . . .
C14 C 0.81022(17) 0.37238(15) 0.19060(9) 0.0179(3) Uani 1 1 d . . .
C15 C 0.70587(17) 0.27288(15) 0.18430(9) 0.0221(4) Uani 1 1 d . . .
H15 H 0.7102 0.2112 0.2246 0.027 Uiso 1 1 calc R . .
C16 C 0.59674(18) 0.26384(15) 0.11994(9) 0.0228(4) Uani 1 1 d . . .
H16 H 0.5265 0.1979 0.1165 0.027 Uiso 1 1 calc R . .
C17 C 0.59436(18) 0.35536(15) 0.06062(10) 0.0233(4) Uani 1 1 d . . .
H17 H 0.5197 0.3509 0.0172 0.028 Uiso 1 1 calc R . .
C18 C 0.92007(17) 0.36850(16) 0.26719(9) 0.0207(4) Uani 1 1 d . . .
N1 N 0.90218(14) 0.61407(12) 0.04533(8) 0.0169(3) Uani 1 1 d . . .
N2 N 1.00308(13) 0.71026(12) 0.03526(7) 0.0173(3) Uani 1 1 d . . .
N3 N 0.89982(14) 0.76463(13) -0.10269(8) 0.0183(3) Uani 1 1 d . . .
N4 N 0.77203(13) 0.56560(12) -0.10157(7) 0.0180(3) Uani 1 1 d . . .
N5 N 1.09343(13) 0.94912(12) -0.09788(7) 0.0172(3) Uani 1 1 d . . .
N6 N 0.69407(14) 0.44983(12) 0.06263(7) 0.0201(3) Uani 1 1 d . . .
O1 O 0.98225(12) 0.62184(11) 0.17723(6) 0.0233(3) Uani 1 1 d . . .
O2 O 1.00021(12) 0.47271(11) 0.28919(6) 0.0257(3) Uani 1 1 d . . .
O3 O 0.92859(13) 0.27164(11) 0.30849(6) 0.0303(3) Uani 1 1 d . . .
H1N H 0.846(2) 0.5763(18) -0.0006(11) 0.046(6) Uiso 1 1 d . . .
H2O H 0.993(2) 0.5380(19) 0.2422(12) 0.057(6) Uiso 1 1 d . . .
H3N H 0.9255(19) 0.8268(17) -0.1356(10) 0.038(5) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2534(17) . ?
C1 N1 1.3262(18) . ?
C1 C13 1.507(2) . ?
C2 N2 1.2895(18) . ?
C2 N3 1.3812(18) . ?
C2 C8 1.498(2) . ?
C3 N4 1.3259(18) . ?
C3 C4 1.394(2) . ?
C3 N3 1.4006(18) . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(2) . ?
C6 H6 0.9300 . ?
C7 N4 1.3482(19) . ?
C7 H7 0.9300 . ?
C8 N5 1.3400(18) . ?
C8 C9 1.387(2) . ?
C9 C10 1.376(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9300 . ?
C12 N5 1.3382(18) . ?
C12 H12 0.9300 . ?
C13 N6 1.3464(18) . ?
C13 C14 1.404(2) . ?
C14 C15 1.393(2) . ?
C14 C18 1.524(2) . ?
C15 C16 1.372(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 N6 1.3301(19) . ?
C17 H17 0.9300 . ?
C18 O3 1.2113(18) . ?
C18 O2 1.3172(19) . ?
N1 N2 1.3828(17) . ?
N1 H1N 0.953(19) . ?
N3 H3N 0.903(17) . ?
O1 H2O 1.39(2) . ?
O2 H2O 1.04(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
O1 C1 N1 122.29(14) . . ?
O1 C1 C13 122.73(13) . . ?
N1 C1 C13 114.97(13) . . ?
N2 C2 N3 134.43(14) . . ?
N2 C2 C8 113.74(13) . . ?
N3 C2 C8 111.77(13) . . ?
N4 C3 C4 122.99(14) . . ?
N4 C3 N3 119.27(13) . . ?
C4 C3 N3 117.74(14) . . ?
C5 C4 C3 118.38(14) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.51(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 118.15(14) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N4 C7 C6 123.44(14) . . ?
N4 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
N5 C8 C9 122.82(14) . . ?
N5 C8 C2 115.52(13) . . ?
C9 C8 C2 121.66(13) . . ?
C10 C9 C8 118.49(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 119.33(14) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 118.44(14) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N5 C12 C11 123.37(14) . . ?
N5 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N6 C13 C14 122.53(14) . . ?
N6 C13 C1 111.84(12) . . ?
C14 C13 C1 125.63(14) . . ?
C15 C14 C13 116.16(14) . . ?
C15 C14 C18 113.91(14) . . ?
C13 C14 C18 129.93(14) . . ?
C16 C15 C14 121.47(15) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 117.96(15) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
N6 C17 C16 122.91(15) . . ?
N6 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
O3 C18 O2 120.85(15) . . ?
O3 C18 C14 119.65(15) . . ?
O2 C18 C14 119.43(14) . . ?
C1 N1 N2 116.60(12) . . ?
C1 N1 H1N 124.4(11) . . ?
N2 N1 H1N 118.6(11) . . ?
C2 N2 N1 120.09(12) . . ?
C2 N3 C3 135.69(14) . . ?
C2 N3 H3N 108.9(11) . . ?
C3 N3 H3N 114.1(11) . . ?
C3 N4 C7 117.53(13) . . ?
C12 N5 C8 117.55(13) . . ?
C17 N6 C13 118.92(13) . . ?
C1 O1 H2O 110.0(8) . . ?
C18 O2 H2O 109.6(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
N4 C3 C4 C5 -0.3(2) . . . . ?
N3 C3 C4 C5 178.69(14) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 N4 -0.3(2) . . . . ?
N2 C2 C8 N5 -173.94(13) . . . . ?
N3 C2 C8 N5 3.67(18) . . . . ?
N2 C2 C8 C9 5.4(2) . . . . ?
N3 C2 C8 C9 -176.97(13) . . . . ?
N5 C8 C9 C10 -0.1(2) . . . . ?
C2 C8 C9 C10 -179.45(14) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 N5 -0.4(2) . . . . ?
O1 C1 C13 N6 159.44(14) . . . . ?
N1 C1 C13 N6 -19.51(18) . . . . ?
O1 C1 C13 C14 -21.3(2) . . . . ?
N1 C1 C13 C14 159.74(14) . . . . ?
N6 C13 C14 C15 1.3(2) . . . . ?
C1 C13 C14 C15 -177.89(14) . . . . ?
N6 C13 C14 C18 -179.37(14) . . . . ?
C1 C13 C14 C18 1.5(2) . . . . ?
C13 C14 C15 C16 -2.1(2) . . . . ?
C18 C14 C15 C16 178.45(14) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C15 C16 C17 N6 1.2(2) . . . . ?
C15 C14 C18 O3 13.7(2) . . . . ?
C13 C14 C18 O3 -165.66(15) . . . . ?
C15 C14 C18 O2 -163.51(13) . . . . ?
C13 C14 C18 O2 17.1(2) . . . . ?
O1 C1 N1 N2 5.6(2) . . . . ?
C13 C1 N1 N2 -175.41(12) . . . . ?
N3 C2 N2 N1 0.8(2) . . . . ?
C8 C2 N2 N1 177.66(12) . . . . ?
C1 N1 N2 C2 -169.34(14) . . . . ?
N2 C2 N3 C3 -17.7(3) . . . . ?
C8 C2 N3 C3 165.37(15) . . . . ?
N4 C3 N3 C2 1.7(3) . . . . ?
C4 C3 N3 C2 -177.35(15) . . . . ?
C4 C3 N4 C7 -0.4(2) . . . . ?
N3 C3 N4 C7 -179.42(13) . . . . ?
C6 C7 N4 C3 0.7(2) . . . . ?
C11 C12 N5 C8 0.3(2) . . . . ?
C9 C8 N5 C12 -0.1(2) . . . . ?
C2 C8 N5 C12 179.29(13) . . . . ?
C16 C17 N6 C13 -2.0(2) . . . . ?
C14 C13 N6 C17 0.7(2) . . . . ?
C1 C13 N6 C17 179.97(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1550976'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N5 O3, C H4 O'
_chemical_formula_sum            'C16 H19 N5 O4'
_chemical_formula_weight         345.36

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   20.6565(13)
_cell_length_b                   4.9157(3)
_cell_length_c                   16.5160(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1677.05(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3274
_cell_measurement_theta_min      3.1521
_cell_measurement_theta_max      32.1682

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_min  0.90133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12554
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3825
_reflns_number_gt                2581
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0210P)²] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(1)
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_restrained_S_all      0.806
_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
C1 C 0.17272(9) 1.0162(4) 0.36835(12) 0.0207(5) Uani 1 1 d . . .
C2 C 0.03491(10) 0.7220(4) 0.45812(11) 0.0199(5) Uani 1 1 d . . .
C3 C -0.04457(9) 1.0448(4) 0.38281(12) 0.0184(5) Uani 1 1 d . . .
C4 C -0.11201(10) 1.0896(4) 0.38132(12) 0.0227(5) Uani 1 1 d . . .
H4 H -0.1396 0.9890 0.4142 0.027 Uiso 1 1 calc R . .
C5 C -0.13607(9) 1.2863(4) 0.32986(12) 0.0244(5) Uani 1 1 d . . .
H5 H -0.1803 1.3203 0.3274 0.029 Uiso 1 1 calc R . .
C6 C -0.09329(10) 1.4328(4) 0.28173(13) 0.0257(5) Uani 1 1 d . . .
H6 H -0.1083 1.5654 0.2462 0.031 Uiso 1 1 calc R . .
C7 C -0.02844(11) 1.3770(4) 0.28790(13) 0.0256(5) Uani 1 1 d . . .
H7 H 0.0002 1.4776 0.2563 0.031 Uiso 1 1 calc R . .
C8 C 0.02273(9) 0.5029(4) 0.52037(12) 0.0178(5) Uani 1 1 d . . .
C9 C 0.07290(10) 0.3474(4) 0.55278(11) 0.0221(5) Uani 1 1 d . . .
H9 H 0.1156 0.3767 0.5373 0.026 Uiso 1 1 calc R . .
C10 C 0.05707(10) 0.1461(4) 0.60934(12) 0.0232(5) Uani 1 1 d . . .
H10 H 0.0891 0.0379 0.6323 0.028 Uiso 1 1 calc R . .
C11 C -0.00711(10) 0.1115(4) 0.63038(13) 0.0238(5) Uani 1 1 d . . .
H11 H -0.0189 -0.0210 0.6678 0.029 Uiso 1 1 calc R . .
C12 C -0.05333(10) 0.2751(4) 0.59546(13) 0.0265(5) Uani 1 1 d . . .
H12 H -0.0964 0.2504 0.6102 0.032 Uiso 1 1 calc R . .
C13 C 0.18280(9) 1.2558(4) 0.31210(12) 0.0233(5) Uani 1 1 d . . .
H13B H 0.1881 1.4200 0.3440 0.028 Uiso 1 1 calc R . .
H13A H 0.1447 1.2786 0.2785 0.028 Uiso 1 1 calc R . .
C14 C 0.24171(10) 1.2180(4) 0.25828(12) 0.0230(5) Uani 1 1 d . . .
H14A H 0.2491 1.3844 0.2281 0.028 Uiso 1 1 calc R . .
H14B H 0.2793 1.1866 0.2922 0.028 Uiso 1 1 calc R . .
C15 C 0.23514(9) 0.9858(4) 0.19961(12) 0.0208(5) Uani 1 1 d . . .
O1 O 0.21900(7) 0.8886(3) 0.39745(8) 0.0246(4) Uani 1 1 d . . .
O2 O 0.28779(7) 0.9478(3) 0.15501(9) 0.0299(4) Uani 1 1 d . . .
O3 O 0.18699(7) 0.8461(3) 0.19390(9) 0.0307(4) Uani 1 1 d . . .
N1 N 0.11005(9) 0.9640(3) 0.38480(11) 0.0232(4) Uani 1 1 d . . .
N2 N 0.09518(8) 0.7599(3) 0.43894(9) 0.0217(4) Uani 1 1 d . . .
N3 N -0.02278(9) 0.8428(3) 0.43597(11) 0.0233(4) Uani 1 1 d . . .
N4 N -0.00390(8) 1.1851(3) 0.33705(11) 0.0237(4) Uani 1 1 d . . .
N5 N -0.03921(8) 0.4677(3) 0.54128(10) 0.0223(4) Uani 1 1 d . . .
C16 C 0.21730(10) 0.4420(4) 0.02580(15) 0.0347(6) Uani 1 1 d . . .
H16A H 0.1988 0.3970 0.0774 0.052 Uiso 1 1 calc R . .
H16B H 0.2278 0.2778 -0.0028 0.052 Uiso 1 1 calc R . .
H16C H 0.1867 0.5458 -0.0052 0.052 Uiso 1 1 calc R . .
O4 O 0.27450(7) 0.5981(3) 0.03759(10) 0.0294(4) Uani 1 1 d . . .
H4O H 0.2862(10) 0.681(4) -0.0084(13) 0.027(6) Uiso 1 1 d . . .
H1N H 0.0781(10) 1.056(4) 0.3630(12) 0.030(6) Uiso 1 1 d . . .
H2O H 0.2791(13) 0.813(5) 0.112(2) 0.085(10) Uiso 1 1 d . . .
H3N H -0.0525(11) 0.762(4) 0.4638(14) 0.034(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.240(2) . ?
C1 N1 1.347(2) . ?
C1 C13 1.515(3) . ?
C2 N2 1.298(2) . ?
C2 N3 1.381(3) . ?
C2 C8 1.510(3) . ?
C3 N4 1.324(2) . ?
C3 N3 1.400(2) . ?
C3 C4 1.411(3) . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 N4 1.344(2) . ?
C7 H7 0.9300 . ?
C8 N5 1.336(2) . ?
C8 C9 1.394(3) . ?
C9 C10 1.400(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 N5 1.335(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.518(3) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 C15 1.503(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O3 1.212(2) . ?
C15 O2 1.327(2) . ?
O2 H2O 0.99(3) . ?
N1 N2 1.379(2) . ?
N1 H1N 0.88(2) . ?
N3 H3N 0.86(2) . ?
C16 O4 1.422(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O4 H4O 0.90(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
O1 C1 N1 124.49(19) . . ?
O1 C1 C13 121.67(17) . . ?
N1 C1 C13 113.81(17) . . ?
N2 C2 N3 134.54(19) . . ?
N2 C2 C8 115.35(18) . . ?
N3 C2 C8 110.08(17) . . ?
N4 C3 N3 121.57(18) . . ?
N4 C3 C4 122.36(18) . . ?
N3 C3 C4 116.07(18) . . ?
C5 C4 C3 118.42(19) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.11(18) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 118.36(19) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N4 C7 C6 123.6(2) . . ?
N4 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N5 C8 C9 122.78(17) . . ?
N5 C8 C2 115.32(17) . . ?
C9 C8 C2 121.90(17) . . ?
C8 C9 C10 118.04(19) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N5 C12 C11 123.0(2) . . ?
N5 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C1 C13 C14 111.95(16) . . ?
C1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
H13B C13 H13A 107.9 . . ?
C15 C14 C13 113.47(17) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O3 C15 O2 123.33(19) . . ?
O3 C15 C14 123.66(18) . . ?
O2 C15 C14 113.01(17) . . ?
C15 O2 H2O 110.2(16) . . ?
C1 N1 N2 118.90(18) . . ?
C1 N1 H1N 122.8(13) . . ?
N2 N1 H1N 118.3(13) . . ?
C2 N2 N1 118.44(17) . . ?
C2 N3 C3 138.49(19) . . ?
C2 N3 H3N 105.9(15) . . ?
C3 N3 H3N 115.6(15) . . ?
C3 N4 C7 118.12(17) . . ?
C12 N5 C8 118.30(17) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16 O4 H4O 110.7(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
N4 C3 C4 C5 0.3(3) . . . . ?
N3 C3 C4 C5 -179.90(17) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 N4 1.1(3) . . . . ?
N2 C2 C8 N5 178.73(17) . . . . ?
N3 C2 C8 N5 0.2(2) . . . . ?
N2 C2 C8 C9 -1.9(3) . . . . ?
N3 C2 C8 C9 179.61(18) . . . . ?
N5 C8 C9 C10 0.2(3) . . . . ?
C2 C8 C9 C10 -179.13(17) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 N5 0.2(3) . . . . ?
O1 C1 C13 C14 34.7(3) . . . . ?
N1 C1 C13 C14 -147.26(17) . . . . ?
C1 C13 C14 C15 65.2(2) . . . . ?
C13 C14 C15 O3 1.9(3) . . . . ?
C13 C14 C15 O2 -177.57(16) . . . . ?
O1 C1 N1 N2 1.6(3) . . . . ?
C13 C1 N1 N2 -176.42(15) . . . . ?
N3 C2 N2 N1 0.5(3) . . . . ?
C8 C2 N2 N1 -177.52(16) . . . . ?
C1 N1 N2 C2 175.89(18) . . . . ?
N2 C2 N3 C3 3.4(4) . . . . ?
C8 C2 N3 C3 -178.5(2) . . . . ?
N4 C3 N3 C2 -1.9(4) . . . . ?
C4 C3 N3 C2 178.3(2) . . . . ?
N3 C3 N4 C7 -179.56(18) . . . . ?
C4 C3 N4 C7 0.2(3) . . . . ?
C6 C7 N4 C3 -0.9(3) . . . . ?
C11 C12 N5 C8 -0.2(3) . . . . ?
C9 C8 N5 C12 -0.1(3) . . . . ?
C2 C8 N5 C12 179.32(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1550971'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 {2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinecarbonyl}cyclohexanecarboxylic acid 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N5 O3'
_chemical_formula_sum            'C19 H21 N5 O3'
_chemical_formula_weight         367.41

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   10.7168(6)
_cell_length_b                   11.1292(5)
_cell_length_c                   15.2937(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.246(6)
_cell_angle_gamma                90.00
_cell_volume                     1751.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4339
_cell_measurement_theta_min      3.2670
_cell_measurement_theta_max      32.7769

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_min  0.94481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13441
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.1051
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         26.37
_reflns_number_total             6872
_reflns_number_gt                4569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0423P)²] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_number_reflns         6872
_refine_ls_number_parameters     499
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.004
_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
C1 C 0.5266(3) 0.9622(3) 0.3613(2) 0.0182(7) Uani 1 1 d . . .
C2 C 0.8534(3) 1.0012(3) 0.3658(2) 0.0179(7) Uani 1 1 d . . .
C3 C 0.8340(3) 0.8667(3) 0.2265(2) 0.0199(7) Uani 1 1 d . . .
C4 C 0.8911(3) 0.8520(3) 0.1559(2) 0.0265(8) Uani 1 1 d . . .
H4 H 0.9540 0.9053 0.1483 0.032 Uiso 1 1 calc R . .
C5 C 0.8519(3) 0.7563(3) 0.0977(2) 0.0295(8) Uani 1 1 d . . .
H5 H 0.8893 0.7427 0.0506 0.035 Uiso 1 1 calc R . .
C6 C 0.7558(3) 0.6803(3) 0.1102(2) 0.0290(8) Uani 1 1 d . . .
H6 H 0.7265 0.6159 0.0712 0.035 Uiso 1 1 calc R . .
C7 C 0.7054(3) 0.7020(3) 0.1807(2) 0.0297(8) Uani 1 1 d . . .
H7 H 0.6415 0.6503 0.1890 0.036 Uiso 1 1 calc R . .
C8 C 0.9654(3) 1.0697(3) 0.42468(19) 0.0161(7) Uani 1 1 d . . .
C9 C 0.9540(3) 1.1313(3) 0.5002(2) 0.0219(7) Uani 1 1 d . . .
H9 H 0.8767 1.1298 0.5166 0.026 Uiso 1 1 calc R . .
C10 C 1.0609(3) 1.1957(3) 0.5512(2) 0.0276(8) Uani 1 1 d . . .
H10 H 1.0553 1.2401 0.6015 0.033 Uiso 1 1 calc R . .
C11 C 1.1755(3) 1.1931(3) 0.5265(2) 0.0265(8) Uani 1 1 d . . .
H11 H 1.2489 1.2337 0.5605 0.032 Uiso 1 1 calc R . .
C12 C 1.1779(3) 1.1282(3) 0.4498(2) 0.0223(7) Uani 1 1 d . . .
H12 H 1.2545 1.1269 0.4325 0.027 Uiso 1 1 calc R . .
C13 C 0.4070(3) 0.8977(3) 0.3039(2) 0.0181(7) Uani 1 1 d . . .
H13 H 0.3515 0.9608 0.2683 0.022 Uiso 1 1 calc R . .
C14 C 0.3276(3) 0.8420(3) 0.3625(2) 0.0193(7) Uani 1 1 d . . .
H14 H 0.3081 0.9062 0.4005 0.023 Uiso 1 1 calc R . .
C15 C 0.1981(3) 0.7958(3) 0.3020(2) 0.0265(8) Uani 1 1 d . . .
H151 H 0.1504 0.7578 0.3398 0.032 Uiso 1 1 calc R . .
H152 H 0.1471 0.8632 0.2712 0.032 Uiso 1 1 calc R . .
C16 C 0.2150(3) 0.7069(3) 0.2319(2) 0.0289(8) Uani 1 1 d . . .
H161 H 0.1304 0.6841 0.1927 0.035 Uiso 1 1 calc R . .
H162 H 0.2572 0.6351 0.2622 0.035 Uiso 1 1 calc R . .
C17 C 0.2969(3) 0.7614(3) 0.1743(2) 0.0283(8) Uani 1 1 d . . .
H171 H 0.3120 0.7010 0.1326 0.034 Uiso 1 1 calc R . .
H172 H 0.2495 0.8273 0.1384 0.034 Uiso 1 1 calc R . .
C18 C 0.4269(3) 0.8071(3) 0.2338(2) 0.0221(7) Uani 1 1 d . . .
H181 H 0.4745 0.8449 0.1958 0.026 Uiso 1 1 calc R . .
H182 H 0.4780 0.7399 0.2651 0.026 Uiso 1 1 calc R . .
C19 C 0.4064(3) 0.7470(3) 0.4263(2) 0.0201(7) Uani 1 1 d . . .
C1A C 0.8684(3) 0.6734(3) 0.8479(2) 0.0223(7) Uani 1 1 d . . .
C2A C 0.5456(3) 0.6260(3) 0.8568(2) 0.0198(7) Uani 1 1 d . . .
C3A C 0.4465(3) 0.7713(3) 0.7245(2) 0.0233(8) Uani 1 1 d . . .
C4A C 0.3273(3) 0.7938(3) 0.6598(2) 0.0268(8) Uani 1 1 d . . .
H4A H 0.2563 0.7439 0.6558 0.032 Uiso 1 1 calc R . .
C5A C 0.3168(3) 0.8889(3) 0.6031(2) 0.0284(8) Uani 1 1 d . . .
H5A H 0.2373 0.9070 0.5617 0.034 Uiso 1 1 calc R . .
C6A C 0.4242(3) 0.9590(3) 0.6068(2) 0.0386(9) Uani 1 1 d . . .
H6A H 0.4196 1.0247 0.5684 0.046 Uiso 1 1 calc R . .
C7A C 0.5393(3) 0.9273(3) 0.6701(3) 0.0443(11) Uani 1 1 d . . .
H7A H 0.6132 0.9720 0.6716 0.053 Uiso 1 1 calc R . .
C8A C 0.4868(3) 0.5567(3) 0.91867(19) 0.0181(7) Uani 1 1 d . . .
C9A C 0.5534(3) 0.4672(3) 0.97383(19) 0.0217(7) Uani 1 1 d . . .
H9A H 0.6362 0.4451 0.9718 0.026 Uiso 1 1 calc R . .
C10A C 0.4957(3) 0.4105(3) 1.0323(2) 0.0275(8) Uani 1 1 d . . .
H10A H 0.5389 0.3491 1.0700 0.033 Uiso 1 1 calc R . .
C11A C 0.3733(3) 0.4455(3) 1.0345(2) 0.0275(8) Uani 1 1 d . . .
H11A H 0.3338 0.4111 1.0754 0.033 Uiso 1 1 calc R . .
C12A C 0.3120(3) 0.5323(3) 0.9747(2) 0.0257(8) Uani 1 1 d . . .
H12A H 0.2278 0.5533 0.9741 0.031 Uiso 1 1 calc R . .
C13A C 0.9379(3) 0.7500(3) 0.7960(2) 0.0195(7) Uani 1 1 d . . .
H13A H 0.9732 0.6932 0.7601 0.023 Uiso 1 1 calc R . .
C14A C 1.0576(3) 0.8102(3) 0.8605(2) 0.0290(8) Uani 1 1 d . . .
H14A H 1.1117 0.7468 0.8968 0.035 Uiso 1 1 calc R . .
C15A C 1.1388(3) 0.8741(3) 0.8057(2) 0.0342(9) Uani 1 1 d . . .
H153 H 1.2103 0.9163 0.8474 0.041 Uiso 1 1 calc R . .
H154 H 1.1754 0.8145 0.7736 0.041 Uiso 1 1 calc R . .
C16A C 1.0602(3) 0.9612(3) 0.7387(2) 0.0357(9) Uani 1 1 d . . .
H163 H 1.1140 0.9959 0.7037 0.043 Uiso 1 1 calc R . .
H164 H 1.0318 1.0258 0.7712 0.043 Uiso 1 1 calc R . .
C17A C 0.9416(3) 0.9021(3) 0.6738(2) 0.0363(9) Uani 1 1 d . . .
H173 H 0.9698 0.8439 0.6361 0.044 Uiso 1 1 calc R . .
H174 H 0.8900 0.9627 0.6341 0.044 Uiso 1 1 calc R . .
C18A C 0.8585(3) 0.8395(3) 0.7265(2) 0.0306(8) Uani 1 1 d . . .
H183 H 0.7877 0.7974 0.6840 0.037 Uiso 1 1 calc R . .
H184 H 0.8211 0.8993 0.7578 0.037 Uiso 1 1 calc R . .
C19A C 1.0180(3) 0.8955(3) 0.9258(2) 0.0253(8) Uani 1 1 d . . .
O1 O 0.51397(19) 1.03408(18) 0.42001(14) 0.0251(5) Uani 1 1 d . . .
O2 O 0.3331(2) 0.6708(2) 0.45685(15) 0.0256(5) Uani 1 1 d . . .
O3 O 0.5245(2) 0.7440(2) 0.44826(15) 0.0261(5) Uani 1 1 d . . .
O1A O 0.9298(2) 0.6007(2) 0.90461(15) 0.0301(6) Uani 1 1 d . . .
O3A O 0.9126(2) 0.9119(2) 0.93097(16) 0.0391(7) Uani 1 1 d . . .
O2A O 1.1243(2) 0.9478(2) 0.98002(15) 0.0343(6) Uani 1 1 d . . .
H2A H 1.1031 0.9938 1.0152 0.051 Uiso 1 1 calc R . .
N1 N 0.6392(2) 0.9437(2) 0.34005(17) 0.0187(6) Uani 1 1 d . . .
N2 N 0.7502(2) 0.9996(2) 0.39321(16) 0.0183(6) Uani 1 1 d . . .
N3 N 0.8790(2) 0.9597(2) 0.28699(16) 0.0233(6) Uani 1 1 d . . .
N4 N 0.7425(2) 0.7939(2) 0.23950(17) 0.0232(6) Uani 1 1 d . . .
N5 N 1.0756(2) 1.0674(2) 0.39936(16) 0.0193(6) Uani 1 1 d . . .
N1A N 0.7374(3) 0.6845(3) 0.82602(18) 0.0215(6) Uani 1 1 d . . .
N2A N 0.6713(3) 0.6222(2) 0.87778(17) 0.0211(6) Uani 1 1 d . . .
N3A N 0.4507(3) 0.6800(3) 0.78746(17) 0.0258(7) Uani 1 1 d . . .
N4A N 0.5511(3) 0.8374(3) 0.7288(2) 0.0331(7) Uani 1 1 d . . .
N5A N 0.3657(2) 0.5889(2) 0.91703(17) 0.0229(6) Uani 1 1 d . . .
H1N H 0.6427 0.8697 0.3056 0.034 Uiso 1 1 d . . .
H3N H 0.9626 0.9938 0.2844 0.034 Uiso 1 1 d . . .
H2O H 0.385(4) 0.615(4) 0.496(3) 0.053(12) Uiso 1 1 d . . .
H1A H 0.698(3) 0.738(3) 0.788(2) 0.015(9) Uiso 1 1 d . . .
H3A H 0.368(4) 0.652(3) 0.789(3) 0.055(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.238(3) . ?
C1 N1 1.351(4) . ?
C1 C13 1.517(4) . ?
C2 N2 1.288(4) . ?
C2 N3 1.388(4) . ?
C2 C8 1.492(4) . ?
C3 N4 1.329(4) . ?
C3 N3 1.382(4) . ?
C3 C4 1.392(4) . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.355(4) . ?
C6 H6 0.9300 . ?
C7 N4 1.346(4) . ?
C7 H7 0.9300 . ?
C8 N5 1.343(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 N5 1.334(4) . ?
C12 H12 0.9300 . ?
C13 C18 1.529(4) . ?
C13 C14 1.529(4) . ?
C13 H13 0.9800 . ?
C14 C19 1.524(4) . ?
C14 C15 1.525(4) . ?
C14 H14 0.9800 . ?
C15 C16 1.506(5) . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C16 C17 1.532(4) . ?
C16 H161 0.9700 . ?
C16 H162 0.9700 . ?
C17 C18 1.523(4) . ?
C17 H171 0.9700 . ?
C17 H172 0.9700 . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C19 O3 1.216(3) . ?
C19 O2 1.327(4) . ?
C1A O1A 1.234(4) . ?
C1A N1A 1.354(4) . ?
C1A C13A 1.497(4) . ?
C2A N2A 1.295(4) . ?
C2A N3A 1.385(4) . ?
C2A C8A 1.490(4) . ?
C3A N4A 1.327(4) . ?
C3A N3A 1.392(4) . ?
C3A C4A 1.403(4) . ?
C4A C5A 1.353(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.378(5) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.384(5) . ?
C6A H6A 0.9300 . ?
C7A N4A 1.327(4) . ?
C7A H7A 0.9300 . ?
C8A N5A 1.340(4) . ?
C8A C9A 1.370(4) . ?
C9A C10A 1.374(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.377(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.365(4) . ?
C11A H11A 0.9300 . ?
C12A N5A 1.339(4) . ?
C12A H12A 0.9300 . ?
C13A C18A 1.530(4) . ?
C13A C14A 1.536(4) . ?
C13A H13A 0.9800 . ?
C14A C19A 1.522(5) . ?
C14A C15A 1.541(5) . ?
C14A H14A 0.9800 . ?
C15A C16A 1.489(5) . ?
C15A H153 0.9700 . ?
C15A H154 0.9700 . ?
C16A C17A 1.525(5) . ?
C16A H163 0.9700 . ?
C16A H164 0.9700 . ?
C17A C18A 1.526(4) . ?
C17A H173 0.9700 . ?
C17A H174 0.9700 . ?
C18A H183 0.9700 . ?
C18A H184 0.9700 . ?
C19A O3A 1.169(4) . ?
C19A O2A 1.340(4) . ?
O2 H2O 0.93(4) . ?
O2A H2A 0.8200 . ?
N1 N2 1.386(3) . ?
N1 H1N 0.9842 . ?
N3 H3N 0.9842 . ?
N1A N2A 1.387(3) . ?
N1A H1A 0.85(3) . ?
N3A H3A 0.95(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
O1 C1 N1 124.0(3) . . ?
O1 C1 C13 118.7(3) . . ?
N1 C1 C13 117.1(3) . . ?
N2 C2 N3 132.4(3) . . ?
N2 C2 C8 115.4(3) . . ?
N3 C2 C8 112.0(2) . . ?
N4 C3 N3 119.4(3) . . ?
N4 C3 C4 123.2(3) . . ?
N3 C3 C4 117.4(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N4 C7 C6 123.9(3) . . ?
N4 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
N5 C8 C9 122.9(3) . . ?
N5 C8 C2 116.1(3) . . ?
C9 C8 C2 121.0(3) . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 118.1(3) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
N5 C12 C11 123.2(3) . . ?
N5 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C1 C13 C18 117.2(2) . . ?
C1 C13 C14 111.8(2) . . ?
C18 C13 C14 110.6(2) . . ?
C1 C13 H13 105.4 . . ?
C18 C13 H13 105.4 . . ?
C14 C13 H13 105.4 . . ?
C19 C14 C15 113.7(3) . . ?
C19 C14 C13 110.9(2) . . ?
C15 C14 C13 110.0(2) . . ?
C19 C14 H14 107.3 . . ?
C15 C14 H14 107.3 . . ?
C13 C14 H14 107.3 . . ?
C16 C15 C14 112.5(3) . . ?
C16 C15 H151 109.1 . . ?
C14 C15 H151 109.1 . . ?
C16 C15 H152 109.1 . . ?
C14 C15 H152 109.1 . . ?
H151 C15 H152 107.8 . . ?
C15 C16 C17 110.6(3) . . ?
C15 C16 H161 109.5 . . ?
C17 C16 H161 109.5 . . ?
C15 C16 H162 109.5 . . ?
C17 C16 H162 109.5 . . ?
H161 C16 H162 108.1 . . ?
C18 C17 C16 111.3(3) . . ?
C18 C17 H171 109.4 . . ?
C16 C17 H171 109.4 . . ?
C18 C17 H172 109.4 . . ?
C16 C17 H172 109.4 . . ?
H171 C17 H172 108.0 . . ?
C17 C18 C13 110.8(3) . . ?
C17 C18 H181 109.5 . . ?
C13 C18 H181 109.5 . . ?
C17 C18 H182 109.5 . . ?
C13 C18 H182 109.5 . . ?
H181 C18 H182 108.1 . . ?
O3 C19 O2 123.9(3) . . ?
O3 C19 C14 122.9(3) . . ?
O2 C19 C14 113.1(3) . . ?
O1A C1A N1A 123.1(3) . . ?
O1A C1A C13A 120.0(3) . . ?
N1A C1A C13A 116.9(3) . . ?
N2A C2A N3A 134.0(3) . . ?
N2A C2A C8A 114.9(3) . . ?
N3A C2A C8A 111.1(3) . . ?
N4A C3A N3A 120.5(3) . . ?
N4A C3A C4A 121.7(3) . . ?
N3A C3A C4A 117.7(3) . . ?
C5A C4A C3A 119.2(3) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C4A C5A C6A 119.9(3) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A C7A 117.1(3) . . ?
C5A C6A H6A 121.5 . . ?
C7A C6A H6A 121.5 . . ?
N4A C7A C6A 124.3(3) . . ?
N4A C7A H7A 117.9 . . ?
C6A C7A H7A 117.9 . . ?
N5A C8A C9A 122.8(3) . . ?
N5A C8A C2A 115.4(3) . . ?
C9A C8A C2A 121.9(3) . . ?
C8A C9A C10A 118.9(3) . . ?
C8A C9A H9A 120.6 . . ?
C10A C9A H9A 120.6 . . ?
C9A C10A C11A 119.4(3) . . ?
C9A C10A H10A 120.3 . . ?
C11A C10A H10A 120.3 . . ?
C12A C11A C10A 117.8(3) . . ?
C12A C11A H11A 121.1 . . ?
C10A C11A H11A 121.1 . . ?
N5A C12A C11A 124.0(3) . . ?
N5A C12A H12A 118.0 . . ?
C11A C12A H12A 118.0 . . ?
C1A C13A C18A 118.4(3) . . ?
C1A C13A C14A 111.0(2) . . ?
C18A C13A C14A 111.4(3) . . ?
C1A C13A H13A 104.9 . . ?
C18A C13A H13A 104.9 . . ?
C14A C13A H13A 104.9 . . ?
C19A C14A C13A 110.9(3) . . ?
C19A C14A C15A 111.9(3) . . ?
C13A C14A C15A 110.4(3) . . ?
C19A C14A H14A 107.8 . . ?
C13A C14A H14A 107.8 . . ?
C15A C14A H14A 107.8 . . ?
C16A C15A C14A 112.2(3) . . ?
C16A C15A H153 109.2 . . ?
C14A C15A H153 109.2 . . ?
C16A C15A H154 109.2 . . ?
C14A C15A H154 109.2 . . ?
H153 C15A H154 107.9 . . ?
C15A C16A C17A 112.0(3) . . ?
C15A C16A H163 109.2 . . ?
C17A C16A H163 109.2 . . ?
C15A C16A H164 109.2 . . ?
C17A C16A H164 109.2 . . ?
H163 C16A H164 107.9 . . ?
C16A C17A C18A 110.9(3) . . ?
C16A C17A H173 109.5 . . ?
C18A C17A H173 109.5 . . ?
C16A C17A H174 109.5 . . ?
C18A C17A H174 109.5 . . ?
H173 C17A H174 108.0 . . ?
C17A C18A C13A 111.8(3) . . ?
C17A C18A H183 109.3 . . ?
C13A C18A H183 109.3 . . ?
C17A C18A H184 109.3 . . ?
C13A C18A H184 109.3 . . ?
H183 C18A H184 107.9 . . ?
O3A C19A O2A 124.1(3) . . ?
O3A C19A C14A 126.5(3) . . ?
O2A C19A C14A 109.4(3) . . ?
C19 O2 H2O 110(2) . . ?
C19A O2A H2A 109.5 . . ?
C1 N1 N2 118.0(2) . . ?
C1 N1 H1N 115.2 . . ?
N2 N1 H1N 122.3 . . ?
C2 N2 N1 119.3(2) . . ?
C3 N3 C2 135.6(3) . . ?
C3 N3 H3N 114.4 . . ?
C2 N3 H3N 108.0 . . ?
C3 N4 C7 117.1(3) . . ?
C12 N5 C8 118.0(3) . . ?
C1A N1A N2A 118.3(3) . . ?
C1A N1A H1A 120(2) . . ?
N2A N1A H1A 120(2) . . ?
C2A N2A N1A 120.3(3) . . ?
C2A N3A C3A 136.2(3) . . ?
C2A N3A H3A 109(2) . . ?
C3A N3A H3A 114(2) . . ?
C7A N4A C3A 117.7(3) . . ?
C12A N5A C8A 117.0(3) . . ?

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
N4 C3 C4 C5 -1.0(4) . . . . ?
N3 C3 C4 C5 176.9(3) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 C7 -1.2(5) . . . . ?
C5 C6 C7 N4 0.5(5) . . . . ?
N2 C2 C8 N5 176.9(3) . . . . ?
N3 C2 C8 N5 -8.2(4) . . . . ?
N2 C2 C8 C9 -3.2(4) . . . . ?
N3 C2 C8 C9 171.7(3) . . . . ?
N5 C8 C9 C10 1.3(5) . . . . ?
C2 C8 C9 C10 -178.6(3) . . . . ?
C8 C9 C10 C11 -2.0(5) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C10 C11 C12 N5 -0.7(5) . . . . ?
O1 C1 C13 C18 -178.4(3) . . . . ?
N1 C1 C13 C18 6.5(4) . . . . ?
O1 C1 C13 C14 -49.2(4) . . . . ?
N1 C1 C13 C14 135.7(3) . . . . ?
C1 C13 C14 C19 -62.3(3) . . . . ?
C18 C13 C14 C19 70.2(3) . . . . ?
C1 C13 C14 C15 171.0(3) . . . . ?
C18 C13 C14 C15 -56.4(3) . . . . ?
C19 C14 C15 C16 -68.6(3) . . . . ?
C13 C14 C15 C16 56.5(3) . . . . ?
C14 C15 C16 C17 -55.5(3) . . . . ?
C15 C16 C17 C18 54.9(4) . . . . ?
C16 C17 C18 C13 -56.1(4) . . . . ?
C1 C13 C18 C17 -173.3(3) . . . . ?
C14 C13 C18 C17 57.0(3) . . . . ?
C15 C14 C19 O3 146.3(3) . . . . ?
C13 C14 C19 O3 21.7(4) . . . . ?
C15 C14 C19 O2 -35.3(4) . . . . ?
C13 C14 C19 O2 -159.9(2) . . . . ?
N4A C3A C4A C5A -3.3(5) . . . . ?
N3A C3A C4A C5A 173.9(3) . . . . ?
C3A C4A C5A C6A 2.9(5) . . . . ?
C4A C5A C6A C7A -0.2(5) . . . . ?
C5A C6A C7A N4A -2.5(6) . . . . ?
N2A C2A C8A N5A 159.5(3) . . . . ?
N3A C2A C8A N5A -21.3(4) . . . . ?
N2A C2A C8A C9A -19.8(4) . . . . ?
N3A C2A C8A C9A 159.4(3) . . . . ?
N5A C8A C9A C10A -2.2(4) . . . . ?
C2A C8A C9A C10A 177.0(3) . . . . ?
C8A C9A C10A C11A -0.5(4) . . . . ?
C9A C10A C11A C12A 3.0(5) . . . . ?
C10A C11A C12A N5A -3.0(5) . . . . ?
O1A C1A C13A C18A -179.8(3) . . . . ?
N1A C1A C13A C18A 3.3(4) . . . . ?
O1A C1A C13A C14A -49.0(4) . . . . ?
N1A C1A C13A C14A 134.0(3) . . . . ?
C1A C13A C14A C19A -63.3(3) . . . . ?
C18A C13A C14A C19A 71.0(3) . . . . ?
C1A C13A C14A C15A 172.1(3) . . . . ?
C18A C13A C14A C15A -53.6(3) . . . . ?
C19A C14A C15A C16A -69.3(4) . . . . ?
C13A C14A C15A C16A 54.8(4) . . . . ?
C14A C15A C16A C17A -55.9(4) . . . . ?
C15A C16A C17A C18A 55.3(4) . . . . ?
C16A C17A C18A C13A -54.5(4) . . . . ?
C1A C13A C18A C17A -174.9(3) . . . . ?
C14A C13A C18A C17A 54.5(4) . . . . ?
C13A C14A C19A O3A 2.9(5) . . . . ?
C15A C14A C19A O3A 126.7(4) . . . . ?
C13A C14A C19A O2A -179.0(3) . . . . ?
C15A C14A C19A O2A -55.2(3) . . . . ?
O1 C1 N1 N2 6.6(4) . . . . ?
C13 C1 N1 N2 -178.5(2) . . . . ?
N3 C2 N2 N1 2.8(5) . . . . ?
C8 C2 N2 N1 176.5(2) . . . . ?
C1 N1 N2 C2 -168.0(3) . . . . ?
N4 C3 N3 C2 1.1(5) . . . . ?
C4 C3 N3 C2 -176.9(3) . . . . ?
N2 C2 N3 C3 -30.8(6) . . . . ?
C8 C2 N3 C3 155.4(3) . . . . ?
N3 C3 N4 C7 -177.6(3) . . . . ?
C4 C3 N4 C7 0.3(4) . . . . ?
C6 C7 N4 C3 0.0(5) . . . . ?
C11 C12 N5 C8 0.1(4) . . . . ?
C9 C8 N5 C12 -0.4(4) . . . . ?
C2 C8 N5 C12 179.5(3) . . . . ?
O1A C1A N1A N2A 8.3(4) . . . . ?
C13A C1A N1A N2A -174.8(2) . . . . ?
N3A C2A N2A N1A 1.9(5) . . . . ?
C8A C2A N2A N1A -179.1(3) . . . . ?
C1A N1A N2A C2A -176.9(3) . . . . ?
N2A C2A N3A C3A -17.5(6) . . . . ?
C8A C2A N3A C3A 163.5(3) . . . . ?
N4A C3A N3A C2A -6.9(5) . . . . ?
C4A C3A N3A C2A 175.8(3) . . . . ?
C6A C7A N4A C3A 2.2(6) . . . . ?
N3A C3A N4A C7A -176.4(3) . . . . ?
C4A C3A N4A C7A 0.8(5) . . . . ?
C11A C12A N5A C8A 0.4(5) . . . . ?
C9A C8A N5A C12A 2.3(4) . . . . ?
C2A C8A N5A C12A -177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1550972'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-{2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinecarbonyl}benzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N5 O3'
_chemical_formula_sum            'C19 H15 N5 O3'
_chemical_formula_weight         361.36

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.5625(9)
_cell_length_b                   11.9958(10)
_cell_length_c                   14.2676(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.793(8)
_cell_angle_gamma                90.00
_cell_volume                     1747.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3231
_cell_measurement_theta_min      2.7660
_cell_measurement_theta_max      28.0720

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_min  0.56554
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12747
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3568
_reflns_number_gt                2362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0889P)²+1.2389P] 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         3568
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.2033
_refine_ls_wR_factor_gt          0.1724
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
C1 C 0.2580(3) 0.8786(2) 0.1467(2) 0.0291(7) Uani 1 1 d . . .
C2 C 0.5926(3) 0.9390(3) 0.1769(2) 0.0381(8) Uani 1 1 d . . .
C3 C 0.5911(3) 0.8522(3) 0.0094(2) 0.0424(8) Uani 1 1 d . . .
C4 C 0.6787(4) 0.8277(3) -0.0441(2) 0.0418(8) Uani 1 1 d . . .
H4 H 0.7668 0.8451 -0.0198 0.050 Uiso 1 1 calc R . .
C5 C 0.6374(4) 0.7783(3) -0.1323(2) 0.0434(8) Uani 1 1 d . . .
H5 H 0.6969 0.7614 -0.1684 0.052 Uiso 1 1 calc R . .
C6 C 0.5056(4) 0.7535(3) -0.1680(3) 0.0549(10) Uani 1 1 d . . .
H6 H 0.4739 0.7191 -0.2279 0.066 Uiso 1 1 calc R . .
C7 C 0.4223(4) 0.7826(3) -0.1095(2) 0.0464(9) Uani 1 1 d . . .
H7 H 0.3332 0.7679 -0.1315 0.056 Uiso 1 1 calc R . .
C8 C 0.6962(3) 0.9882(3) 0.2555(2) 0.0419(8) Uani 1 1 d . . .
C9 C 0.6700(3) 1.0319(3) 0.3409(2) 0.0414(8) Uani 1 1 d . . .
H9 H 0.5860 1.0320 0.3502 0.050 Uiso 1 1 calc R . .
C10 C 0.7751(4) 1.0742(3) 0.4093(3) 0.0526(10) Uani 1 1 d . . .
H10 H 0.7617 1.1029 0.4666 0.063 Uiso 1 1 calc R . .
C11 C 0.8979(4) 1.0752(3) 0.3960(3) 0.0578(11) Uani 1 1 d . . .
H11 H 0.9683 1.1047 0.4424 0.069 Uiso 1 1 calc R . .
C12 C 0.9134(4) 1.0314(3) 0.3121(3) 0.0560(10) Uani 1 1 d . . .
H12 H 0.9975 1.0313 0.3029 0.067 Uiso 1 1 calc R . .
C13 C 0.1621(3) 0.8243(2) 0.06304(19) 0.0255(6) Uani 1 1 d . . .
C14 C 0.1334(2) 0.7105(2) 0.05929(18) 0.0240(6) Uani 1 1 d . . .
C15 C 0.0443(3) 0.6677(2) -0.02176(19) 0.0297(7) Uani 1 1 d . . .
H15 H 0.0247 0.5920 -0.0244 0.036 Uiso 1 1 calc R . .
C16 C -0.0160(3) 0.7360(2) -0.0989(2) 0.0333(7) Uani 1 1 d . . .
H16 H -0.0744 0.7061 -0.1531 0.040 Uiso 1 1 calc R . .
C17 C 0.0114(3) 0.8479(2) -0.0942(2) 0.0365(7) Uani 1 1 d . . .
H17 H -0.0297 0.8943 -0.1452 0.044 Uiso 1 1 calc R . .
C18 C 0.1000(3) 0.8922(3) -0.0140(2) 0.0355(7) Uani 1 1 d . . .
H18 H 0.1182 0.9682 -0.0117 0.043 Uiso 1 1 calc R . .
C19 C 0.2038(3) 0.6358(2) 0.13957(19) 0.0264(6) Uani 1 1 d . . .
N1 N 0.3744(2) 0.8931(2) 0.1267(2) 0.0371(6) Uani 1 1 d . . .
N2 N 0.4776(3) 0.9383(2) 0.19444(18) 0.0375(6) Uani 1 1 d . . .
N3 N 0.6396(3) 0.9026(2) 0.10232(19) 0.0402(7) Uani 1 1 d . . .
N4 N 0.4672(3) 0.8307(2) -0.02314(19) 0.0465(7) Uani 1 1 d . . .
N5 N 0.8168(3) 0.9879(2) 0.2409(2) 0.0447(7) Uani 1 1 d . . .
O1 O 0.2259(2) 0.90914(16) 0.22039(14) 0.0354(5) Uani 1 1 d . . .
O2 O 0.1502(2) 0.53593(17) 0.13632(16) 0.0410(6) Uani 1 1 d . . .
O3 O 0.29970(19) 0.66404(15) 0.20060(13) 0.0319(5) Uani 1 1 d . . .
H1N H 0.398(3) 0.866(3) 0.070(2) 0.038 Uiso 1 1 d . . .
H2O H 0.200(4) 0.492(3) 0.184(3) 0.074(13) Uiso 1 1 d . . .
H3N H 0.726(4) 0.916(3) 0.113(3) 0.049(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.240(3) . ?
C1 N1 1.342(4) . ?
C1 C13 1.502(4) . ?
C2 N2 1.301(4) . ?
C2 N3 1.356(4) . ?
C2 C8 1.475(4) . ?
C3 N4 1.298(4) . ?
C3 C4 1.374(5) . ?
C3 N3 1.427(4) . ?
C4 C5 1.359(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(5) . ?
C6 H6 0.9300 . ?
C7 N4 1.333(4) . ?
C7 H7 0.9300 . ?
C8 N5 1.343(4) . ?
C8 C9 1.418(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(6) . ?
C11 H11 0.9300 . ?
C12 N5 1.347(4) . ?
C12 H12 0.9300 . ?
C13 C18 1.391(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.494(4) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O3 1.203(3) . ?
C19 O2 1.321(3) . ?
N1 N2 1.371(3) . ?
N1 H1N 0.96(3) . ?
N3 H3N 0.90(4) . ?
O2 H2O 0.91(5) . ?

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
O1 C1 N1 127.3(3) . . ?
O1 C1 C13 121.8(3) . . ?
N1 C1 C13 110.9(3) . . ?
N2 C2 N3 134.1(3) . . ?
N2 C2 C8 113.8(3) . . ?
N3 C2 C8 112.1(3) . . ?
N4 C3 C4 121.3(3) . . ?
N4 C3 N3 120.4(3) . . ?
C4 C3 N3 118.3(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 116.8(3) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N4 C7 C6 121.9(3) . . ?
N4 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N5 C8 C9 122.4(3) . . ?
N5 C8 C2 115.5(3) . . ?
C9 C8 C2 122.1(3) . . ?
C10 C9 C8 116.6(3) . . ?
C10 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
C11 C10 C9 122.1(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 117.1(3) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
N5 C12 C11 125.3(4) . . ?
N5 C12 H12 117.4 . . ?
C11 C12 H12 117.4 . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 C1 117.4(2) . . ?
C14 C13 C1 123.4(2) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 C19 121.0(2) . . ?
C13 C14 C19 119.8(2) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O3 C19 O2 123.7(2) . . ?
O3 C19 C14 123.3(2) . . ?
O2 C19 C14 113.1(2) . . ?
C1 N1 N2 120.6(3) . . ?
C1 N1 H1N 125.6(19) . . ?
N2 N1 H1N 113.5(19) . . ?
C2 N2 N1 118.7(3) . . ?
C2 N3 C3 138.4(3) . . ?
C2 N3 H3N 112(2) . . ?
C3 N3 H3N 110(2) . . ?
C3 N4 C7 120.4(3) . . ?
C8 N5 C12 116.6(3) . . ?
C19 O2 H2O 110(3) . . ?

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
N4 C3 C4 C5 -1.1(5) . . . . ?
N3 C3 C4 C5 179.1(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 N4 -0.8(5) . . . . ?
N2 C2 C8 N5 178.5(3) . . . . ?
N3 C2 C8 N5 -0.5(4) . . . . ?
N2 C2 C8 C9 -1.0(4) . . . . ?
N3 C2 C8 C9 -180.0(3) . . . . ?
N5 C8 C9 C10 -0.2(5) . . . . ?
C2 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 N5 0.6(6) . . . . ?
O1 C1 C13 C18 96.1(3) . . . . ?
N1 C1 C13 C18 -80.6(3) . . . . ?
O1 C1 C13 C14 -84.2(4) . . . . ?
N1 C1 C13 C14 99.1(3) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C1 C13 C14 C15 -179.3(3) . . . . ?
C18 C13 C14 C19 177.3(3) . . . . ?
C1 C13 C14 C19 -2.5(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C19 C14 C15 C16 -176.5(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C1 C13 C18 C17 179.3(3) . . . . ?
C15 C14 C19 O3 164.2(3) . . . . ?
C13 C14 C19 O3 -12.5(4) . . . . ?
C15 C14 C19 O2 -15.6(4) . . . . ?
C13 C14 C19 O2 167.7(2) . . . . ?
O1 C1 N1 N2 5.5(4) . . . . ?
C13 C1 N1 N2 -178.0(2) . . . . ?
N3 C2 N2 N1 -0.4(5) . . . . ?
C8 C2 N2 N1 -179.1(2) . . . . ?
C1 N1 N2 C2 172.1(3) . . . . ?
N2 C2 N3 C3 3.0(7) . . . . ?
C8 C2 N3 C3 -178.3(3) . . . . ?
N4 C3 N3 C2 0.6(6) . . . . ?
C4 C3 N3 C2 -179.6(3) . . . . ?
C4 C3 N4 C7 0.9(5) . . . . ?
N3 C3 N4 C7 -179.3(3) . . . . ?
C6 C7 N4 C3 0.0(5) . . . . ?
C9 C8 N5 C12 0.1(5) . . . . ?
C2 C8 N5 C12 -179.3(3) . . . . ?
C11 C12 N5 C8 -0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.069

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1550974'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 4-{2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinecarbonyl}nicotinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N6 O3'
_chemical_formula_sum            'C18 H14 N6 O3'
_chemical_formula_weight         362.35

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.6450(10)
_cell_length_b                   9.8790(10)
_cell_length_c                   15.864(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.520(10)
_cell_angle_gamma                90.00
_cell_volume                     1666.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2632
_cell_measurement_theta_min      3.0510
_cell_measurement_theta_max      28.7970

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_min  0.92617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7733
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3812
_reflns_number_gt                2807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'


_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)+(0.0455P)²+0.2212P] 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         3812
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.62581(17) 0.18713(16) 0.11872(11) 0.0187(4) Uani 1 1 d . . .
C2 C 0.80705(17) -0.03881(17) 0.00689(11) 0.0197(4) Uani 1 1 d . . .
C3 C 0.72467(18) 0.05623(17) -0.13446(11) 0.0214(4) Uani 1 1 d . . .
C4 C 0.7646(2) 0.0892(2) -0.21447(12) 0.0319(5) Uani 1 1 d . . .
H4 H 0.8481 0.0782 -0.2279 0.038 Uiso 1 1 calc R . .
C5 C 0.6765(2) 0.1386(2) -0.27337(12) 0.0362(5) Uani 1 1 d . . .
H5 H 0.7006 0.1628 -0.3270 0.043 Uiso 1 1 calc R . .
C6 C 0.5519(2) 0.15210(19) -0.25211(11) 0.0282(5) Uani 1 1 d . . .
H6 H 0.4907 0.1833 -0.2910 0.034 Uiso 1 1 calc R . .
C7 C 0.52248(19) 0.11781(17) -0.17173(11) 0.0239(4) Uani 1 1 d . . .
H7 H 0.4393 0.1273 -0.1571 0.029 Uiso 1 1 calc R . .
C8 C 0.89699(17) -0.15029(17) 0.03021(11) 0.0209(4) Uani 1 1 d . . .
C9 C 0.90210(18) -0.20768(17) 0.11030(11) 0.0232(4) Uani 1 1 d . . .
H9 H 0.8502 -0.1766 0.1518 0.028 Uiso 1 1 calc R . .
C10 C 0.9860(2) -0.31185(18) 0.12688(12) 0.0303(5) Uani 1 1 d . . .
H10 H 0.9906 -0.3535 0.1795 0.036 Uiso 1 1 calc R . .
C11 C 1.0628(2) -0.3530(2) 0.06407(13) 0.0345(5) Uani 1 1 d . . .
H11 H 1.1211 -0.4220 0.0739 0.041 Uiso 1 1 calc R . .
C12 C 1.05202(19) -0.29061(19) -0.01357(12) 0.0303(5) Uani 1 1 d . . .
H12 H 1.1049 -0.3188 -0.0553 0.036 Uiso 1 1 calc R . .
C13 C 0.53243(17) 0.29547(16) 0.09600(10) 0.0171(4) Uani 1 1 d . . .
C14 C 0.54413(17) 0.42487(16) 0.13178(10) 0.0177(4) Uani 1 1 d . . .
C15 C 0.45046(17) 0.51825(17) 0.11256(11) 0.0218(4) Uani 1 1 d . . .
H15 H 0.4567 0.6028 0.1381 0.026 Uiso 1 1 calc R . .
C16 C 0.34288(18) 0.37122(18) 0.02479(11) 0.0237(4) Uani 1 1 d . . .
H16 H 0.2755 0.3529 -0.0128 0.028 Uiso 1 1 calc R . .
C17 C 0.42922(17) 0.27025(17) 0.04212(11) 0.0212(4) Uani 1 1 d . . .
H17 H 0.4183 0.1852 0.0177 0.025 Uiso 1 1 calc R . .
C18 C 0.66120(18) 0.46815(17) 0.18127(11) 0.0213(4) Uani 1 1 d . . .
N1 N 0.66538(15) 0.11743(13) 0.05237(10) 0.0202(3) Uani 1 1 d . . .
N2 N 0.74329(14) 0.00731(13) 0.06820(9) 0.0197(3) Uani 1 1 d . . .
N3 N 0.81348(16) 0.00152(16) -0.07613(9) 0.0233(4) Uani 1 1 d . . .
N4 N 0.60627(15) 0.07115(14) -0.11236(9) 0.0215(3) Uani 1 1 d . . .
N5 N 0.96954(14) -0.19165(14) -0.03232(9) 0.0236(4) Uani 1 1 d . . .
N6 N 0.35135(16) 0.49512(15) 0.05960(10) 0.0278(4) Uani 1 1 d . . .
O1 O 0.66001(13) 0.16724(12) 0.19304(7) 0.0272(3) Uani 1 1 d . . .
O2 O 0.63522(14) 0.55181(13) 0.24340(8) 0.0279(3) Uani 1 1 d . . .
O3 O 0.76486(13) 0.43419(14) 0.16317(9) 0.0354(4) Uani 1 1 d . . .
H1N H 0.6345(19) 0.1240(19) -0.0027(13) 0.029(5) Uiso 1 1 d . . .
H2O H 0.715(3) 0.586(3) 0.2715(18) 0.080(9) Uiso 1 1 d . . .
H3N H 0.877(2) -0.0406(19) -0.0980(13) 0.033(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.234(2) . ?
C1 N1 1.341(2) . ?
C1 C13 1.494(2) . ?
C2 N2 1.293(2) . ?
C2 N3 1.380(2) . ?
C2 C8 1.495(3) . ?
C3 N4 1.331(2) . ?
C3 C4 1.395(2) . ?
C3 N3 1.402(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(2) . ?
C6 H6 0.9300 . ?
C7 N4 1.349(2) . ?
C7 H7 0.9300 . ?
C8 N5 1.347(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 N5 1.339(2) . ?
C12 H12 0.9300 . ?
C13 C17 1.385(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.383(2) . ?
C14 C18 1.505(3) . ?
C15 N6 1.339(2) . ?
C15 H15 0.9300 . ?
C16 N6 1.344(2) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.200(2) . ?
C18 O2 1.325(2) . ?
N1 N2 1.384(2) . ?
N1 H1N 0.92(2) . ?
N3 H3N 0.88(2) . ?
O2 H2O 1.00(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
O1 C1 N1 125.33(17) . . ?
O1 C1 C13 120.65(15) . . ?
N1 C1 C13 114.02(15) . . ?
N2 C2 N3 131.72(17) . . ?
N2 C2 C8 115.15(15) . . ?
N3 C2 C8 112.99(15) . . ?
N4 C3 C4 122.92(17) . . ?
N4 C3 N3 119.19(15) . . ?
C4 C3 N3 117.86(17) . . ?
C5 C4 C3 118.22(19) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 119.71(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 117.52(18) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
N4 C7 C6 124.30(18) . . ?
N4 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N5 C8 C9 123.27(17) . . ?
N5 C8 C2 115.01(15) . . ?
C9 C8 C2 121.71(15) . . ?
C10 C9 C8 118.50(17) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 118.82(19) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 119.03(19) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N5 C12 C11 123.62(18) . . ?
N5 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C17 C13 C14 117.90(16) . . ?
C17 C13 C1 121.43(15) . . ?
C14 C13 C1 120.61(16) . . ?
C15 C14 C13 117.95(17) . . ?
C15 C14 C18 119.87(15) . . ?
C13 C14 C18 121.80(16) . . ?
N6 C15 C14 124.42(16) . . ?
N6 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
N6 C16 C17 123.09(18) . . ?
N6 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C16 C17 C13 119.86(17) . . ?
C16 C17 H17 120.1 . . ?
C13 C17 H17 120.1 . . ?
O3 C18 O2 125.21(18) . . ?
O3 C18 C14 122.99(16) . . ?
O2 C18 C14 111.73(16) . . ?
C1 N1 N2 117.87(15) . . ?
C1 N1 H1N 126.6(12) . . ?
N2 N1 H1N 114.4(12) . . ?
C2 N2 N1 118.07(15) . . ?
C2 N3 C3 132.90(16) . . ?
C2 N3 H3N 108.2(14) . . ?
C3 N3 H3N 115.5(14) . . ?
C3 N4 C7 117.29(15) . . ?
C12 N5 C8 116.72(16) . . ?
C15 N6 C16 116.73(16) . . ?
C18 O2 H2O 109.8(16) . . ?

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
N4 C3 C4 C5 -0.5(3) . . . . ?
N3 C3 C4 C5 177.69(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C5 C6 C7 N4 -0.5(3) . . . . ?
N2 C2 C8 N5 -175.56(15) . . . . ?
N3 C2 C8 N5 0.7(2) . . . . ?
N2 C2 C8 C9 5.7(3) . . . . ?
N3 C2 C8 C9 -178.02(15) . . . . ?
N5 C8 C9 C10 0.3(3) . . . . ?
C2 C8 C9 C10 178.90(17) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 N5 -0.6(3) . . . . ?
O1 C1 C13 C17 -131.66(18) . . . . ?
N1 C1 C13 C17 48.0(2) . . . . ?
O1 C1 C13 C14 45.6(2) . . . . ?
N1 C1 C13 C14 -134.73(16) . . . . ?
C17 C13 C14 C15 1.4(2) . . . . ?
C1 C13 C14 C15 -175.88(15) . . . . ?
C17 C13 C14 C18 -171.41(15) . . . . ?
C1 C13 C14 C18 11.3(2) . . . . ?
C13 C14 C15 N6 -2.5(3) . . . . ?
C18 C14 C15 N6 170.47(16) . . . . ?
N6 C16 C17 C13 -1.7(3) . . . . ?
C14 C13 C17 C16 0.5(2) . . . . ?
C1 C13 C17 C16 177.83(15) . . . . ?
C15 C14 C18 O3 -136.13(19) . . . . ?
C13 C14 C18 O3 36.6(3) . . . . ?
C15 C14 C18 O2 40.9(2) . . . . ?
C13 C14 C18 O2 -146.35(16) . . . . ?
O1 C1 N1 N2 5.4(3) . . . . ?
C13 C1 N1 N2 -174.32(14) . . . . ?
N3 C2 N2 N1 -0.2(3) . . . . ?
C8 C2 N2 N1 175.19(15) . . . . ?
C1 N1 N2 C2 -162.67(16) . . . . ?
N2 C2 N3 C3 -34.0(3) . . . . ?
C8 C2 N3 C3 150.58(18) . . . . ?
N4 C3 N3 C2 -3.3(3) . . . . ?
C4 C3 N3 C2 178.46(18) . . . . ?
C4 C3 N4 C7 1.4(3) . . . . ?
N3 C3 N4 C7 -176.76(15) . . . . ?
C6 C7 N4 C3 -0.9(3) . . . . ?
C11 C12 N5 C8 2.0(3) . . . . ?
C9 C8 N5 C12 -1.9(3) . . . . ?
C2 C8 N5 C12 179.45(16) . . . . ?
C14 C15 N6 C16 1.4(3) . . . . ?
C17 C16 N6 C15 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1550975'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 4-oxo-4-{2-[pyridin-2-yl(pyridin-2-ylamino)methylidene]hydrazinyl}butanoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N5 O3'
_chemical_formula_sum            'C15 H15 N5 O3'
_chemical_formula_weight         313.32

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.7517(7)
_cell_length_b                   21.1933(15)
_cell_length_c                   14.2957(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.149(7)
_cell_angle_gamma                90.00
_cell_volume                     2877.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3421
_cell_measurement_theta_min      2.8740
_cell_measurement_theta_max      25.5670

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_min  0.93977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32058
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_av_sigmaI/netI    0.1135
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5884
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

_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)+(0.0389P)²] 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         5884
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
O1A O 0.5886(2) 0.67931(9) 0.34526(14) 0.0230(5) Uani 1 1 d . . .
O1 O 0.9927(2) 0.30903(9) 0.30066(14) 0.0222(5) Uani 1 1 d . . .
N1A N 0.4099(2) 0.74352(11) 0.35415(17) 0.0176(6) Uani 1 1 d . . .
N2 N 0.6962(2) 0.23256(11) 0.34129(16) 0.0175(6) Uani 1 1 d . . .
N2A N 0.2818(2) 0.74909(11) 0.37813(15) 0.0165(6) Uani 1 1 d . . .
N1 N 0.8216(2) 0.24114(12) 0.31457(18) 0.0181(6) Uani 1 1 d . . .
O3 O 0.9545(2) 0.43551(10) 0.59485(14) 0.0296(6) Uani 1 1 d . . .
O2A O 0.7104(2) 0.54830(9) 0.59226(13) 0.0222(5) Uani 1 1 d . . .
O3A O 0.5618(2) 0.61974(9) 0.62629(14) 0.0263(5) Uani 1 1 d . . .
N3 N 0.6630(3) 0.13424(11) 0.25583(18) 0.0182(6) Uani 1 1 d . . .
N5 N 0.4065(2) 0.12700(11) 0.30169(16) 0.0207(6) Uani 1 1 d . . .
N3A N 0.2435(2) 0.84719(11) 0.29344(17) 0.0170(6) Uani 1 1 d . . .
C8 C 0.4793(3) 0.17998(13) 0.32849(19) 0.0161(7) Uani 1 1 d . . .
O2 O 0.7861(2) 0.47044(10) 0.47376(15) 0.0248(5) Uani 1 1 d . . .
C4A C 0.4413(3) 0.88439(13) 0.4190(2) 0.0185(7) Uani 1 1 d . . .
H4A H 0.4304 0.8527 0.4616 0.022 Uiso 1 1 calc R . .
C13A C 0.4245(3) 0.63926(13) 0.43289(19) 0.0186(7) Uani 1 1 d . . .
H13C H 0.3364 0.6232 0.3944 0.022 Uiso 1 1 calc R . .
H13D H 0.4045 0.6592 0.4894 0.022 Uiso 1 1 calc R . .
C8A C 0.0623(3) 0.79950(13) 0.36662(19) 0.0160(7) Uani 1 1 d . . .
C2A C 0.2052(3) 0.79751(13) 0.34808(19) 0.0162(7) Uani 1 1 d . . .
N4A N 0.3682(2) 0.93550(11) 0.26895(18) 0.0173(6) Uani 1 1 d . . .
N4 N 0.8578(2) 0.10515(11) 0.37618(17) 0.0224(6) Uani 1 1 d . . .
C2 C 0.6236(3) 0.18272(14) 0.31064(19) 0.0174(7) Uani 1 1 d . . .
C14 C 0.9416(3) 0.39411(13) 0.4372(2) 0.0190(7) Uani 1 1 d . . .
H14A H 1.0312 0.3747 0.4664 0.023 Uiso 1 1 calc R . .
H14B H 0.9556 0.4203 0.3845 0.023 Uiso 1 1 calc R . .
C13 C 0.8351(3) 0.34251(13) 0.3975(2) 0.0178(7) Uani 1 1 d . . .
H13A H 0.8124 0.3194 0.4506 0.021 Uiso 1 1 calc R . .
H13B H 0.7491 0.3618 0.3614 0.021 Uiso 1 1 calc R . .
C1A C 0.4818(3) 0.68774(13) 0.37588(19) 0.0167(7) Uani 1 1 d . . .
N5A N -0.0062(2) 0.85472(11) 0.35003(16) 0.0190(6) Uani 1 1 d . . .
C3A C 0.3499(3) 0.88765(13) 0.3277(2) 0.0156(7) Uani 1 1 d . . .
C14A C 0.5244(3) 0.58413(13) 0.46453(19) 0.0189(7) Uani 1 1 d . . .
H14C H 0.4705 0.5453 0.4532 0.023 Uiso 1 1 calc R . .
H14D H 0.5922 0.5832 0.4243 0.023 Uiso 1 1 calc R . .
C11A C -0.2010(3) 0.80586(14) 0.3984(2) 0.0216(7) Uani 1 1 d . . .
H11A H -0.2910 0.8096 0.4094 0.026 Uiso 1 1 calc R . .
C9A C 0.0027(3) 0.74577(14) 0.3968(2) 0.0203(7) Uani 1 1 d . . .
H9A H 0.0521 0.7079 0.4052 0.024 Uiso 1 1 calc R . .
C9 C 0.4234(3) 0.23171(14) 0.36788(19) 0.0204(7) Uani 1 1 d . . .
H9 H 0.4769 0.2679 0.3855 0.025 Uiso 1 1 calc R . .
C11 C 0.2112(3) 0.17311(15) 0.3531(2) 0.0259(8) Uani 1 1 d . . .
H11 H 0.1196 0.1692 0.3611 0.031 Uiso 1 1 calc R . .
C3 C 0.7762(3) 0.09331(13) 0.2897(2) 0.0166(7) Uani 1 1 d . . .
C10 C 0.2877(3) 0.22787(15) 0.3799(2) 0.0235(7) Uani 1 1 d . . .
H10 H 0.2478 0.2616 0.4058 0.028 Uiso 1 1 calc R . .
C1 C 0.8897(3) 0.29727(14) 0.3337(2) 0.0180(7) Uani 1 1 d . . .
C4 C 0.7962(3) 0.04315(13) 0.2314(2) 0.0186(7) Uani 1 1 d . . .
H4 H 0.7363 0.0371 0.1715 0.022 Uiso 1 1 calc R . .
C15 C 0.8962(3) 0.43498(13) 0.5103(2) 0.0173(7) Uani 1 1 d . . .
C7A C 0.4711(3) 0.97854(13) 0.2939(2) 0.0202(7) Uani 1 1 d . . .
H7A H 0.4797 1.0104 0.2509 0.024 Uiso 1 1 calc R . .
C6 C 0.9937(3) 0.01320(14) 0.3547(2) 0.0269(8) Uani 1 1 d . . .
H6 H 1.0690 -0.0135 0.3790 0.032 Uiso 1 1 calc R . .
C12A C -0.1367(3) 0.85647(14) 0.3660(2) 0.0219(7) Uani 1 1 d . . .
H12A H -0.1864 0.8942 0.3546 0.026 Uiso 1 1 calc R . .
C12 C 0.2744(3) 0.12462(15) 0.3145(2) 0.0236(7) Uani 1 1 d . . .
H12 H 0.2224 0.0881 0.2961 0.028 Uiso 1 1 calc R . .
C10A C -0.1293(3) 0.74939(15) 0.4141(2) 0.0235(7) Uani 1 1 d . . .
H10A H -0.1701 0.7143 0.4360 0.028 Uiso 1 1 calc R . .
C5A C 0.5467(3) 0.92800(14) 0.4449(2) 0.0227(7) Uani 1 1 d . . .
H5A H 0.6076 0.9256 0.5051 0.027 Uiso 1 1 calc R . .
C5 C 0.9063(3) 0.00291(14) 0.2647(2) 0.0232(7) Uani 1 1 d . . .
H5 H 0.9225 -0.0310 0.2273 0.028 Uiso 1 1 calc R . .
C15A C 0.6039(3) 0.58521(14) 0.5680(2) 0.0180(7) Uani 1 1 d . . .
C6A C 0.5632(3) 0.97619(14) 0.3813(2) 0.0244(7) Uani 1 1 d . . .
H6A H 0.6351 1.0058 0.3982 0.029 Uiso 1 1 calc R . .
C7 C 0.9649(3) 0.06439(14) 0.4068(2) 0.0261(8) Uani 1 1 d . . .
H7 H 1.0232 0.0712 0.4671 0.031 Uiso 1 1 calc R . .
H3N H 0.592(3) 0.1176(13) 0.213(2) 0.022(9) Uiso 1 1 d . . .
H3A H 0.173(3) 0.8626(14) 0.239(2) 0.037(9) Uiso 1 1 d . . .
H4N H 0.300(3) 0.9386(14) 0.207(2) 0.047(10) Uiso 1 1 d . . .
H1N H 0.841(3) 0.2167(14) 0.269(2) 0.033(10) Uiso 1 1 d . . .
H2 H 0.765(4) 0.4978(17) 0.523(3) 0.066(13) Uiso 1 1 d . . .
H1A H 0.435(3) 0.7717(15) 0.306(2) 0.044(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.231(3) . ?
O1 C1 1.228(3) . ?
N1A N2A 1.374(3) . ?
N1A C1A 1.374(3) . ?
N1A H1A 0.98(3) . ?
N2 C2 1.292(3) . ?
N2 N1 1.373(3) . ?
N2A C2A 1.284(3) . ?
N1 C1 1.359(3) . ?
N1 H1N 0.89(3) . ?
O3 C15 1.213(3) . ?
O2A C15A 1.284(3) . ?
O3A C15A 1.247(3) . ?
N3 C2 1.398(3) . ?
N3 C3 1.401(3) . ?
N3 H3N 0.88(3) . ?
N5 C8 1.337(3) . ?
N5 C12 1.343(3) . ?
N3A C3A 1.349(3) . ?
N3A C2A 1.411(3) . ?
N3A H3A 0.97(3) . ?
C8 C9 1.398(4) . ?
C8 C2 1.487(4) . ?
O2 C15 1.317(3) . ?
O2 H2 0.97(4) . ?
C4A C5A 1.369(4) . ?
C4A C3A 1.404(4) . ?
C4A H4A 0.9300 . ?
C13A C1A 1.496(4) . ?
C13A C14A 1.523(4) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C8A N5A 1.342(3) . ?
C8A C9A 1.391(4) . ?
C8A C2A 1.477(4) . ?
N4A C7A 1.343(3) . ?
N4A C3A 1.354(3) . ?
N4A H4N 0.98(3) . ?
N4 C3 1.333(3) . ?
N4 C7 1.349(3) . ?
C14 C15 1.499(4) . ?
C14 C13 1.526(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 C1 1.502(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N5A C12A 1.344(3) . ?
C14A C15A 1.505(4) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C11A C12A 1.375(4) . ?
C11A C10A 1.379(4) . ?
C11A H11A 0.9300 . ?
C9A C10A 1.367(4) . ?
C9A H9A 0.9300 . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C11 C12 1.377(4) . ?
C11 C10 1.386(4) . ?
C11 H11 0.9300 . ?
C3 C4 1.391(4) . ?
C10 H10 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C7A C6A 1.363(4) . ?
C7A H7A 0.9300 . ?
C6 C7 1.380(4) . ?
C6 C5 1.390(4) . ?
C6 H6 0.9300 . ?
C12A H12A 0.9300 . ?
C12 H12 0.9300 . ?
C10A H10A 0.9300 . ?
C5A C6A 1.401(4) . ?
C5A H5A 0.9300 . ?
C5 H5 0.9300 . ?
C6A H6A 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2A N1A C1A 117.7(2) . . ?
N2A N1A H1A 120.7(18) . . ?
C1A N1A H1A 118.9(18) . . ?
C2 N2 N1 117.9(2) . . ?
C2A N2A N1A 118.5(2) . . ?
C1 N1 N2 119.0(2) . . ?
C1 N1 H1N 119(2) . . ?
N2 N1 H1N 118.9(19) . . ?
C2 N3 C3 123.9(2) . . ?
C2 N3 H3N 114.0(18) . . ?
C3 N3 H3N 114.9(18) . . ?
C8 N5 C12 117.1(3) . . ?
C3A N3A C2A 123.5(2) . . ?
C3A N3A H3A 115.0(17) . . ?
C2A N3A H3A 117.9(18) . . ?
N5 C8 C9 122.9(3) . . ?
N5 C8 C2 116.4(3) . . ?
C9 C8 C2 120.6(3) . . ?
C15 O2 H2 110(2) . . ?
C5A C4A C3A 119.8(3) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C1A C13A C14A 113.3(2) . . ?
C1A C13A H13C 108.9 . . ?
C14A C13A H13C 108.9 . . ?
C1A C13A H13D 108.9 . . ?
C14A C13A H13D 108.9 . . ?
H13C C13A H13D 107.7 . . ?
N5A C8A C9A 122.9(3) . . ?
N5A C8A C2A 116.4(2) . . ?
C9A C8A C2A 120.7(3) . . ?
N2A C2A N3A 125.1(3) . . ?
N2A C2A C8A 117.6(3) . . ?
N3A C2A C8A 117.2(2) . . ?
C7A N4A C3A 122.7(3) . . ?
C7A N4A H4N 120.4(19) . . ?
C3A N4A H4N 116.9(19) . . ?
C3 N4 C7 115.8(3) . . ?
N2 C2 N3 126.3(3) . . ?
N2 C2 C8 116.2(3) . . ?
N3 C2 C8 117.3(2) . . ?
C15 C14 C13 112.9(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C13 C14 112.2(2) . . ?
C1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O1A C1A N1A 118.3(3) . . ?
O1A C1A C13A 123.0(3) . . ?
N1A C1A C13A 118.6(3) . . ?
C8A N5A C12A 116.5(3) . . ?
N3A C3A N4A 116.7(3) . . ?
N3A C3A C4A 125.4(3) . . ?
N4A C3A C4A 117.9(3) . . ?
C15A C14A C13A 115.6(2) . . ?
C15A C14A H14C 108.4 . . ?
C13A C14A H14C 108.4 . . ?
C15A C14A H14D 108.4 . . ?
C13A C14A H14D 108.4 . . ?
H14C C14A H14D 107.4 . . ?
C12A C11A C10A 118.6(3) . . ?
C12A C11A H11A 120.7 . . ?
C10A C11A H11A 120.7 . . ?
C10A C9A C8A 119.2(3) . . ?
C10A C9A H9A 120.4 . . ?
C8A C9A H9A 120.4 . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N4 C3 C4 124.3(3) . . ?
N4 C3 N3 117.5(3) . . ?
C4 C3 N3 118.2(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O1 C1 N1 120.4(3) . . ?
O1 C1 C13 122.5(3) . . ?
N1 C1 C13 117.1(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
O3 C15 O2 123.0(3) . . ?
O3 C15 C14 123.6(3) . . ?
O2 C15 C14 113.4(3) . . ?
N4A C7A C6A 121.0(3) . . ?
N4A C7A H7A 119.5 . . ?
C6A C7A H7A 119.5 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
N5A C12A C11A 123.9(3) . . ?
N5A C12A H12A 118.0 . . ?
C11A C12A H12A 118.0 . . ?
N5 C12 C11 123.9(3) . . ?
N5 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C9A C10A C11A 118.9(3) . . ?
C9A C10A H10A 120.6 . . ?
C11A C10A H10A 120.6 . . ?
C4A C5A C6A 120.4(3) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A H5A 119.8 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
O3A C15A O2A 123.1(3) . . ?
O3A C15A C14A 119.4(3) . . ?
O2A C15A C14A 117.4(3) . . ?
C7A C6A C5A 118.2(3) . . ?
C7A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
N4 C7 C6 124.4(3) . . ?
N4 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?

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
C1A N1A N2A C2A -171.6(2) . . . . ?
C2 N2 N1 C1 170.3(3) . . . . ?
C12 N5 C8 C9 -0.3(4) . . . . ?
C12 N5 C8 C2 -177.9(2) . . . . ?
N1A N2A C2A N3A -1.6(4) . . . . ?
N1A N2A C2A C8A 174.2(2) . . . . ?
C3A N3A C2A N2A -66.6(4) . . . . ?
C3A N3A C2A C8A 117.6(3) . . . . ?
N5A C8A C2A N2A 168.7(2) . . . . ?
C9A C8A C2A N2A -13.2(4) . . . . ?
N5A C8A C2A N3A -15.2(4) . . . . ?
C9A C8A C2A N3A 162.9(3) . . . . ?
N1 N2 C2 N3 3.3(4) . . . . ?
N1 N2 C2 C8 -171.0(2) . . . . ?
C3 N3 C2 N2 66.3(4) . . . . ?
C3 N3 C2 C8 -119.5(3) . . . . ?
N5 C8 C2 N2 -176.4(2) . . . . ?
C9 C8 C2 N2 6.0(4) . . . . ?
N5 C8 C2 N3 8.8(4) . . . . ?
C9 C8 C2 N3 -168.8(3) . . . . ?
C15 C14 C13 C1 -173.1(2) . . . . ?
N2A N1A C1A O1A 171.9(2) . . . . ?
N2A N1A C1A C13A -6.2(4) . . . . ?
C14A C13A C1A O1A 10.5(4) . . . . ?
C14A C13A C1A N1A -171.5(2) . . . . ?
C9A C8A N5A C12A 1.4(4) . . . . ?
C2A C8A N5A C12A 179.4(2) . . . . ?
C2A N3A C3A N4A -175.7(2) . . . . ?
C2A N3A C3A C4A 3.7(4) . . . . ?
C7A N4A C3A N3A -179.2(3) . . . . ?
C7A N4A C3A C4A 1.4(4) . . . . ?
C5A C4A C3A N3A 179.2(3) . . . . ?
C5A C4A C3A N4A -1.4(4) . . . . ?
C1A C13A C14A C15A 102.6(3) . . . . ?
N5A C8A C9A C10A -2.5(4) . . . . ?
C2A C8A C9A C10A 179.5(2) . . . . ?
N5 C8 C9 C10 0.2(4) . . . . ?
C2 C8 C9 C10 177.7(2) . . . . ?
C7 N4 C3 C4 -0.6(4) . . . . ?
C7 N4 C3 N3 179.3(3) . . . . ?
C2 N3 C3 N4 -6.1(4) . . . . ?
C2 N3 C3 C4 173.8(3) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C12 C11 C10 C9 -0.6(4) . . . . ?
N2 N1 C1 O1 -171.3(2) . . . . ?
N2 N1 C1 C13 9.9(4) . . . . ?
C14 C13 C1 O1 -15.4(4) . . . . ?
C14 C13 C1 N1 163.4(2) . . . . ?
N4 C3 C4 C5 0.2(4) . . . . ?
N3 C3 C4 C5 -179.6(3) . . . . ?
C13 C14 C15 O3 112.0(3) . . . . ?
C13 C14 C15 O2 -68.0(3) . . . . ?
C3A N4A C7A C6A -0.3(4) . . . . ?
C8A N5A C12A C11A 0.5(4) . . . . ?
C10A C11A C12A N5A -1.1(4) . . . . ?
C8 N5 C12 C11 0.0(4) . . . . ?
C10 C11 C12 N5 0.5(5) . . . . ?
C8A C9A C10A C11A 1.8(4) . . . . ?
C12A C11A C10A C9A -0.1(4) . . . . ?
C3A C4A C5A C6A 0.5(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 C6 C5 C4 -0.2(4) . . . . ?
C13A C14A C15A O3A 17.4(4) . . . . ?
C13A C14A C15A O2A -164.9(2) . . . . ?
N4A C7A C6A C5A -0.7(4) . . . . ?
C4A C5A C6A C7A 0.6(4) . . . . ?
C3 N4 C7 C6 0.5(4) . . . . ?
C5 C6 C7 N4 -0.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.063
