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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2
# start Validation Reply Form
_vrf_PLAT353_2                   
;
PROBLEM: Long    N-H (N0.87,N1.01A) N3     -   H1     ...       1.12 Ang.       
RESPONSE: Probably because of the location that this hydrogen atom is located 
in between the two pyrazolyl nitrogen atoms and hydrogen bonded.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.35

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   Cc

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

_cell_length_a                   19.167(6)
_cell_length_b                   4.5557(15)
_cell_length_c                   18.226(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.720(10)
_cell_angle_gamma                90.00
_cell_volume                     1563.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8729
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9583
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8729
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2449
_reflns_number_gt                1825
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0799P)²+0.8483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(3)
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     212
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.2248(3) 0.5738(11) -0.1607(3) 0.0705(14) Uani 1 1 d . . .
H1A H 0.2694 0.6276 -0.1303 0.106 Uiso 1 1 calc R . .
H1B H 0.1977 0.7477 -0.1761 0.106 Uiso 1 1 calc R . .
H1C H 0.2332 0.4691 -0.2039 0.106 Uiso 1 1 calc R . .
C2 C 0.1850(2) 0.3849(10) -0.1172(2) 0.0561(11) Uani 1 1 d . . .
C3 C 0.1175(2) 0.2552(10) -0.1410(3) 0.0598(11) Uani 1 1 d . . .
H3 H 0.0888 0.2766 -0.1878 0.072 Uiso 1 1 calc R . .
C4 C 0.1026(2) 0.0979(10) -0.0848(3) 0.0573(12) Uani 1 1 d . . .
C5 C 0.0373(3) -0.0742(11) -0.0795(3) 0.0728(14) Uani 1 1 d . . .
H5A H 0.0427 -0.1629 -0.0310 0.109 Uiso 1 1 calc R . .
H5B H 0.0305 -0.2246 -0.1171 0.109 Uiso 1 1 calc R . .
H5C H -0.0031 0.0542 -0.0871 0.109 Uiso 1 1 calc R . .
C6 C 0.1718(2) 0.0015(10) 0.0441(2) 0.0571(11) Uani 1 1 d . . .
C7 C 0.2359(2) 0.0650(9) 0.0985(2) 0.0545(11) Uani 1 1 d . . .
C8 C 0.2518(2) -0.0656(11) 0.1685(3) 0.0677(13) Uani 1 1 d . . .
H8 H 0.2240 -0.2017 0.1879 0.081 Uiso 1 1 calc R . .
C9 C 0.3166(3) 0.0447(11) 0.2037(3) 0.0667(13) Uani 1 1 d . . .
H9 H 0.3402 -0.0030 0.2516 0.080 Uiso 1 1 calc R . .
C10 C 0.3399(2) 0.2374(9) 0.1554(2) 0.0549(10) Uani 1 1 d . . .
C11 C 0.4080(2) 0.3949(9) 0.1730(2) 0.0578(11) Uani 1 1 d . . .
C12 C 0.5511(3) 0.7276(13) 0.1902(3) 0.0814(15) Uani 1 1 d . . .
H12A H 0.5402 0.5903 0.2264 0.122 Uiso 1 1 calc R . .
H12B H 0.5600 0.9173 0.2130 0.122 Uiso 1 1 calc R . .
H12C H 0.5925 0.6628 0.1723 0.122 Uiso 1 1 calc R . .
C13 C 0.4904(2) 0.7469(10) 0.1270(3) 0.0565(11) Uani 1 1 d . . .
C14 C 0.4825(2) 0.9113(11) 0.0644(3) 0.0620(12) Uani 1 1 d . . .
H14 H 0.5156 1.0435 0.0523 0.074 Uiso 1 1 calc R . .
C15 C 0.4163(2) 0.8490(9) 0.0210(3) 0.0562(11) Uani 1 1 d . . .
C16 C 0.3832(2) 0.9719(12) -0.0525(3) 0.0720(14) Uani 1 1 d . . .
H16A H 0.3371 0.8862 -0.0683 0.108 Uiso 1 1 calc R . .
H16B H 0.4124 0.9284 -0.0885 0.108 Uiso 1 1 calc R . .
H16C H 0.3785 1.1808 -0.0483 0.108 Uiso 1 1 calc R . .
N1 N 0.21107(19) 0.3087(8) -0.0486(2) 0.0575(9) Uani 1 1 d . . .
N2 N 0.16034(18) 0.1313(8) -0.02713(19) 0.0553(9) Uani 1 1 d . . .
N3 N 0.28990(17) 0.2521(7) 0.09227(19) 0.0500(8) Uani 1 1 d . . .
H1 H 0.293(2) 0.368(9) 0.039(3) 0.060 Uiso 1 1 d . . .
N4 N 0.42767(18) 0.5863(8) 0.1196(2) 0.0547(9) Uani 1 1 d . . .
N5 N 0.38194(18) 0.6498(7) 0.0544(2) 0.0544(9) Uani 1 1 d . . .
O1 O 0.12771(18) -0.1701(8) 0.0594(2) 0.0811(11) Uani 1 1 d . . .
O2 O 0.44801(18) 0.3533(8) 0.23183(19) 0.0799(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.475(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.305(5) . ?
C2 C3 1.415(6) . ?
C3 C4 1.325(6) . ?
C3 H3 0.9300 . ?
C4 N2 1.386(5) . ?
C4 C5 1.494(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O1 1.220(5) . ?
C6 N2 1.407(5) . ?
C6 C7 1.458(6) . ?
C7 N3 1.361(5) . ?
C7 C8 1.388(6) . ?
C8 C9 1.383(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(6) . ?
C9 H9 0.9300 . ?
C10 N3 1.356(5) . ?
C10 C11 1.470(6) . ?
C11 O2 1.212(5) . ?
C11 N4 1.410(5) . ?
C12 C13 1.479(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.350(7) . ?
C13 N4 1.393(5) . ?
C14 C15 1.395(6) . ?
C14 H14 0.9300 . ?
C15 N5 1.333(6) . ?
C15 C16 1.480(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.376(5) . ?
N3 H1 1.12(5) . ?
N4 N5 1.370(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.4(4) . . ?
N1 C2 C1 121.7(4) . . ?
C3 C2 C1 127.9(4) . . ?
C4 C3 C2 107.8(4) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C3 C4 N2 105.6(4) . . ?
C3 C4 C5 129.6(4) . . ?
N2 C4 C5 124.7(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N2 119.0(4) . . ?
O1 C6 C7 120.2(4) . . ?
N2 C6 C7 120.7(4) . . ?
N3 C7 C8 107.8(4) . . ?
N3 C7 C6 128.7(4) . . ?
C8 C7 C6 123.5(4) . . ?
C9 C8 C7 107.2(4) . . ?
C9 C8 H8 126.4 . . ?
C7 C8 H8 126.4 . . ?
C10 C9 C8 107.8(4) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
N3 C10 C9 108.2(4) . . ?
N3 C10 C11 128.3(4) . . ?
C9 C10 C11 123.5(4) . . ?
O2 C11 N4 120.1(4) . . ?
O2 C11 C10 120.4(4) . . ?
N4 C11 C10 119.5(4) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N4 104.5(4) . . ?
C14 C13 C12 129.8(4) . . ?
N4 C13 C12 125.7(5) . . ?
C13 C14 C15 108.3(4) . . ?
C13 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
N5 C15 C14 110.7(4) . . ?
N5 C15 C16 120.4(4) . . ?
C14 C15 C16 128.9(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 N1 N2 105.3(3) . . ?
N1 N2 C4 110.9(3) . . ?
N1 N2 C6 120.8(3) . . ?
C4 N2 C6 128.2(4) . . ?
C10 N3 C7 109.0(4) . . ?
C10 N3 H1 128(2) . . ?
C7 N3 H1 122(2) . . ?
N5 N4 C13 112.0(4) . . ?
N5 N4 C11 121.3(3) . . ?
C13 N4 C11 126.5(4) . . ?
C15 N5 N4 104.5(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
N1 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C4 178.6(4) . . . . ?
C2 C3 C4 N2 0.1(5) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
O1 C6 C7 N3 -178.7(4) . . . . ?
N2 C6 C7 N3 2.7(7) . . . . ?
O1 C6 C7 C8 1.5(7) . . . . ?
N2 C6 C7 C8 -177.1(4) . . . . ?
N3 C7 C8 C9 -0.6(5) . . . . ?
C6 C7 C8 C9 179.3(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 N3 1.4(5) . . . . ?
C8 C9 C10 C11 -178.9(4) . . . . ?
N3 C10 C11 O2 -178.4(4) . . . . ?
C9 C10 C11 O2 2.0(7) . . . . ?
N3 C10 C11 N4 -1.0(6) . . . . ?
C9 C10 C11 N4 179.4(4) . . . . ?
N4 C13 C14 C15 0.1(5) . . . . ?
C12 C13 C14 C15 179.0(5) . . . . ?
C13 C14 C15 N5 0.1(5) . . . . ?
C13 C14 C15 C16 -179.9(5) . . . . ?
C3 C2 N1 N2 -0.6(5) . . . . ?
C1 C2 N1 N2 -179.0(4) . . . . ?
C2 N1 N2 C4 0.6(5) . . . . ?
C2 N1 N2 C6 178.3(4) . . . . ?
C3 C4 N2 N1 -0.4(5) . . . . ?
C5 C4 N2 N1 -178.3(4) . . . . ?
C3 C4 N2 C6 -177.9(4) . . . . ?
C5 C4 N2 C6 4.3(7) . . . . ?
O1 C6 N2 N1 -175.1(4) . . . . ?
C7 C6 N2 N1 3.5(6) . . . . ?
O1 C6 N2 C4 2.1(7) . . . . ?
C7 C6 N2 C4 -179.3(4) . . . . ?
C9 C10 N3 C7 -1.8(5) . . . . ?
C11 C10 N3 C7 178.5(4) . . . . ?
C8 C7 N3 C10 1.5(5) . . . . ?
C6 C7 N3 C10 -178.4(4) . . . . ?
C14 C13 N4 N5 -0.2(5) . . . . ?
C12 C13 N4 N5 -179.2(5) . . . . ?
C14 C13 N4 C11 -175.7(4) . . . . ?
C12 C13 N4 C11 5.4(7) . . . . ?
O2 C11 N4 N5 -176.4(4) . . . . ?
C10 C11 N4 N5 6.1(5) . . . . ?
O2 C11 N4 C13 -1.3(6) . . . . ?
C10 C11 N4 C13 -178.8(4) . . . . ?
C14 C15 N5 N4 -0.2(5) . . . . ?
C16 C15 N5 N4 179.8(4) . . . . ?
C13 N4 N5 C15 0.3(4) . . . . ?
C11 N4 N5 C15 176.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5A O1 0.96 2.09 2.824(6) 131.8 .
C12 H12A O2 0.96 2.09 2.819(6) 131.6 .
N3 H1 N1 1.12(5) 2.03(5) 2.738(5) 118(3) .
N3 H1 N5 1.12(5) 2.11(4) 2.706(5) 110(3) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 998866'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N5 O'
_chemical_formula_weight         297.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.6780(9)
_cell_length_b                   10.1309(12)
_cell_length_c                   10.3932(11)
_cell_angle_alpha                104.171(6)
_cell_angle_beta                 108.391(6)
_cell_angle_gamma                110.259(6)
_cell_volume                     746.32(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1018
_cell_measurement_theta_min      4.89
_cell_measurement_theta_max      58.78

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8494
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.89
_diffrn_reflns_theta_max         59.08
_reflns_number_total             2031
_reflns_number_gt                1688
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0203(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50448(16) 0.29653(14) 0.48960(12) 0.0259(3) Uani 1 1 d . . .
N1 N 0.85826(18) 0.56543(15) 1.22340(13) 0.0142(3) Uani 1 1 d . . .
N2 N 0.95893(18) 0.65481(15) 1.17063(14) 0.0168(4) Uani 1 1 d . . .
N3 N 0.82033(17) 0.31039(15) 1.15398(13) 0.0137(3) Uani 1 1 d . . .
N4 N 0.97565(17) 0.34129(15) 1.13446(13) 0.0157(4) Uani 1 1 d . . .
N5 N 0.70921(19) 0.40267(16) 0.88193(14) 0.0150(3) Uani 1 1 d . . .
H5 H 0.825(3) 0.467(2) 0.9117(18) 0.018 Uiso 1 1 d . . .
C1 C 0.7294(2) 0.40652(18) 1.13216(16) 0.0140(4) Uani 1 1 d . . .
H1A H 0.6347 0.3790 1.1695 0.017 Uiso 1 1 calc R . .
C2 C 1.0762(2) 0.78607(18) 1.28689(17) 0.0171(4) Uani 1 1 d . . .
C3 C 1.0530(2) 0.77982(19) 1.41446(17) 0.0180(4) Uani 1 1 d . . .
H3 H 1.1206 0.8589 1.5110 0.022 Uiso 1 1 calc R . .
C4 C 0.9141(2) 0.63770(19) 1.37137(16) 0.0154(4) Uani 1 1 d . . .
C5 C 1.2125(2) 0.9140(2) 1.27368(19) 0.0255(5) Uani 1 1 d . . .
H5A H 1.1888 0.8876 1.1698 0.038 Uiso 1 1 calc R . .
H5B H 1.3361 0.9308 1.3321 0.038 Uiso 1 1 calc R . .
H5C H 1.2021 1.0078 1.3105 0.038 Uiso 1 1 calc R . .
C6 C 0.8244(2) 0.5639(2) 1.45326(17) 0.0216(4) Uani 1 1 d . . .
H6A H 0.8845 0.6342 1.5575 0.032 Uiso 1 1 calc R . .
H6B H 0.8346 0.4693 1.4456 0.032 Uiso 1 1 calc R . .
H6C H 0.6950 0.5398 1.4106 0.032 Uiso 1 1 calc R . .
C7 C 0.7594(2) 0.17863(17) 1.17634(15) 0.0142(4) Uani 1 1 d . . .
C8 C 0.8843(2) 0.12396(19) 1.17464(16) 0.0163(4) Uani 1 1 d . . .
H8 H 0.8823 0.0341 1.1882 0.020 Uiso 1 1 calc R . .
C9 C 1.0154(2) 0.22837(19) 1.14883(15) 0.0146(4) Uani 1 1 d . . .
C10 C 0.5899(2) 0.11689(19) 1.19688(17) 0.0189(4) Uani 1 1 d . . .
H10A H 0.6018 0.1921 1.2841 0.028 Uiso 1 1 calc R . .
H10B H 0.5720 0.0213 1.2107 0.028 Uiso 1 1 calc R . .
H10C H 0.4845 0.0967 1.1093 0.028 Uiso 1 1 calc R . .
C11 C 1.1839(2) 0.2279(2) 1.14028(18) 0.0205(4) Uani 1 1 d . . .
H11A H 1.2287 0.2980 1.0953 0.031 Uiso 1 1 calc R . .
H11B H 1.1552 0.1239 1.0799 0.031 Uiso 1 1 calc R . .
H11C H 1.2784 0.2613 1.2400 0.031 Uiso 1 1 calc R . .
C12 C 0.6295(2) 0.37069(18) 0.97127(17) 0.0134(4) Uani 1 1 d . . .
C13 C 0.4435(2) 0.28246(18) 0.88466(17) 0.0168(4) Uani 1 1 d . . .
H13A H 0.3545 0.2440 0.9185 0.020 Uiso 1 1 calc R . .
C14 C 0.4095(2) 0.25988(18) 0.73826(17) 0.0174(4) Uani 1 1 d . . .
H14A H 0.2936 0.2026 0.6544 0.021 Uiso 1 1 calc R . .
C16 C 0.5758(2) 0.33633(18) 0.73834(16) 0.0153(4) Uani 1 1 d . . .
C17 C 0.6190(2) 0.35215(19) 0.61782(17) 0.0184(4) Uani 1 1 d . . .
H17 H 0.7529 0.4134 0.6448 0.028 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2207(19) . ?
N1 C4 1.3670(19) . ?
N1 N2 1.3717(18) . ?
N1 C1 1.442(2) . ?
N2 C2 1.328(2) . ?
N3 C7 1.362(2) . ?
N3 N4 1.3665(18) . ?
N3 C1 1.466(2) . ?
N4 C9 1.332(2) . ?
N5 C12 1.358(2) . ?
N5 C16 1.378(2) . ?
N5 H5 0.882(19) . ?
C1 C12 1.500(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.415(2) . ?
C2 C5 1.492(2) . ?
C3 C4 1.367(2) . ?
C3 H3 0.9500 . ?
C4 C6 1.489(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.381(2) . ?
C7 C10 1.492(2) . ?
C8 C9 1.408(2) . ?
C8 H8 0.9500 . ?
C9 C11 1.494(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.380(2) . ?
C13 C14 1.398(2) . ?
C13 H13A 0.9500 . ?
C14 C16 1.381(2) . ?
C14 H14A 0.9500 . ?
C16 C17 1.445(2) . ?
C17 H17 1.0116 . ?

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
C4 N1 N2 112.35(13) . . ?
C4 N1 C1 126.13(13) . . ?
N2 N1 C1 120.88(12) . . ?
C2 N2 N1 104.71(12) . . ?
C7 N3 N4 112.57(13) . . ?
C7 N3 C1 128.04(13) . . ?
N4 N3 C1 118.96(12) . . ?
C9 N4 N3 104.75(13) . . ?
C12 N5 C16 109.03(14) . . ?
C12 N5 H5 125.7(11) . . ?
C16 N5 H5 124.6(11) . . ?
N1 C1 N3 109.70(12) . . ?
N1 C1 C12 115.27(13) . . ?
N3 C1 C12 111.42(12) . . ?
N1 C1 H1A 106.6 . . ?
N3 C1 H1A 106.6 . . ?
C12 C1 H1A 106.6 . . ?
N2 C2 C3 110.76(14) . . ?
N2 C2 C5 120.79(14) . . ?
C3 C2 C5 128.43(15) . . ?
C4 C3 C2 106.50(14) . . ?
C4 C3 H3 126.8 . . ?
C2 C3 H3 126.8 . . ?
N1 C4 C3 105.66(14) . . ?
N1 C4 C6 122.17(14) . . ?
C3 C4 C6 132.13(14) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 105.55(14) . . ?
N3 C7 C10 123.34(14) . . ?
C8 C7 C10 131.11(15) . . ?
C7 C8 C9 106.13(15) . . ?
C7 C8 H8 126.9 . . ?
C9 C8 H8 126.9 . . ?
N4 C9 C8 110.97(15) . . ?
N4 C9 C11 119.92(15) . . ?
C8 C9 C11 129.09(16) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 108.14(14) . . ?
N5 C12 C1 125.44(14) . . ?
C13 C12 C1 125.91(14) . . ?
C12 C13 C14 107.79(14) . . ?
C12 C13 H13A 126.1 . . ?
C14 C13 H13A 126.1 . . ?
C16 C14 C13 107.18(14) . . ?
C16 C14 H14A 126.4 . . ?
C13 C14 H14A 126.4 . . ?
N5 C16 C14 107.85(13) . . ?
N5 C16 C17 121.82(15) . . ?
C14 C16 C17 130.32(14) . . ?
O1 C17 C16 123.70(15) . . ?
O1 C17 H17 120.1 . . ?
C16 C17 H17 116.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C2 -1.52(18) . . . . ?
C1 N1 N2 C2 -172.88(14) . . . . ?
C7 N3 N4 C9 -1.62(15) . . . . ?
C1 N3 N4 C9 -174.69(12) . . . . ?
C4 N1 C1 N3 -79.08(18) . . . . ?
N2 N1 C1 N3 91.01(16) . . . . ?
C4 N1 C1 C12 154.19(15) . . . . ?
N2 N1 C1 C12 -35.7(2) . . . . ?
C7 N3 C1 N1 133.68(14) . . . . ?
N4 N3 C1 N1 -54.46(16) . . . . ?
C7 N3 C1 C12 -97.45(17) . . . . ?
N4 N3 C1 C12 74.41(16) . . . . ?
N1 N2 C2 C3 1.08(18) . . . . ?
N1 N2 C2 C5 179.33(15) . . . . ?
N2 C2 C3 C4 -0.3(2) . . . . ?
C5 C2 C3 C4 -178.39(18) . . . . ?
N2 N1 C4 C3 1.35(18) . . . . ?
C1 N1 C4 C3 172.16(15) . . . . ?
N2 N1 C4 C6 179.49(15) . . . . ?
C1 N1 C4 C6 -9.7(2) . . . . ?
C2 C3 C4 N1 -0.62(18) . . . . ?
C2 C3 C4 C6 -178.49(18) . . . . ?
N4 N3 C7 C8 1.47(16) . . . . ?
C1 N3 C7 C8 173.76(13) . . . . ?
N4 N3 C7 C10 -178.44(12) . . . . ?
C1 N3 C7 C10 -6.2(2) . . . . ?
N3 C7 C8 C9 -0.71(16) . . . . ?
C10 C7 C8 C9 179.20(15) . . . . ?
N3 N4 C9 C8 1.12(16) . . . . ?
N3 N4 C9 C11 -177.47(13) . . . . ?
C7 C8 C9 N4 -0.27(17) . . . . ?
C7 C8 C9 C11 178.16(14) . . . . ?
C16 N5 C12 C13 0.31(18) . . . . ?
C16 N5 C12 C1 172.50(15) . . . . ?
N1 C1 C12 N5 56.3(2) . . . . ?
N3 C1 C12 N5 -69.5(2) . . . . ?
N1 C1 C12 C13 -132.84(17) . . . . ?
N3 C1 C12 C13 101.31(19) . . . . ?
N5 C12 C13 C14 0.18(19) . . . . ?
C1 C12 C13 C14 -171.97(15) . . . . ?
C12 C13 C14 C16 -0.59(18) . . . . ?
C12 N5 C16 C14 -0.68(18) . . . . ?
C12 N5 C16 C17 179.25(15) . . . . ?
C13 C14 C16 N5 0.78(18) . . . . ?
C13 C14 C16 C17 -179.15(17) . . . . ?
N5 C16 C17 O1 -179.16(16) . . . . ?
C14 C16 C17 O1 0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 N4 0.882(19) 2.376(18) 3.136(2) 144.4(15) 2_767
N5 H5 N2 0.882(19) 2.489(16) 2.9215(19) 110.9(13) .

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        59.08
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 998867'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H31 N9 O'
_chemical_formula_weight         485.60

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   19.389(3)
_cell_length_b                   13.8717(17)
_cell_length_c                   9.8796(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.655(4)
_cell_angle_gamma                90.00
_cell_volume                     2570.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    30038
_cell_measurement_theta_min      1.09
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30038
_diffrn_reflns_av_R_equivalents  0.1460
_diffrn_reflns_av_sigmaI/netI    0.1009
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4528
_reflns_number_gt                1897
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0808P)²+3.2186P] 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         4528
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1961
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2341
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1073(4) 0.1679(5) -0.1952(8) 0.109(3) Uani 1 1 d . . .
H1A H 0.1543 0.1474 -0.1465 0.163 Uiso 1 1 calc R . .
H1B H 0.1085 0.2346 -0.2203 0.163 Uiso 1 1 calc R . .
H1C H 0.0909 0.1299 -0.2784 0.163 Uiso 1 1 calc R . .
C2 C 0.0582(4) 0.1552(4) -0.1032(8) 0.0801(19) Uani 1 1 d . . .
C3 C -0.0149(4) 0.1766(5) -0.1325(10) 0.103(3) Uani 1 1 d . . .
H3 H -0.0421 0.2038 -0.2148 0.124 Uiso 1 1 calc R . .
C4 C -0.0387(4) 0.1511(5) -0.0216(10) 0.092(2) Uani 1 1 d . . .
C5 C -0.1127(3) 0.1568(7) 0.0012(9) 0.139(4) Uani 1 1 d . . .
H5A H -0.1120 0.1327 0.0926 0.208 Uiso 1 1 calc R . .
H5B H -0.1448 0.1187 -0.0683 0.208 Uiso 1 1 calc R . .
H5C H -0.1284 0.2227 -0.0063 0.208 Uiso 1 1 calc R . .
C6 C 0.0233(3) 0.0789(5) 0.2103(8) 0.0746(18) Uani 1 1 d . . .
C7 C 0.0919(3) 0.0474(4) 0.2994(7) 0.0619(15) Uani 1 1 d . . .
C8 C 0.1015(3) 0.0043(5) 0.4271(7) 0.0743(17) Uani 1 1 d . . .
H8 H 0.0658 -0.0094 0.4720 0.089 Uiso 1 1 calc R . .
C9 C 0.1734(3) -0.0154(4) 0.4783(6) 0.0634(15) Uani 1 1 d . . .
H9 H 0.1946 -0.0446 0.5635 0.076 Uiso 1 1 calc R . .
C10 C 0.2079(3) 0.0161(4) 0.3801(5) 0.0499(13) Uani 1 1 d . . .
C11 C 0.2864(2) 0.0182(3) 0.3881(5) 0.0442(12) Uani 1 1 d . . .
C12 C 0.4311(3) -0.0840(4) 0.3598(6) 0.0665(16) Uani 1 1 d . . .
H12A H 0.4218 -0.0722 0.4494 0.100 Uiso 1 1 calc R . .
H12B H 0.4707 -0.0452 0.3506 0.100 Uiso 1 1 calc R . .
H12C H 0.4422 -0.1509 0.3524 0.100 Uiso 1 1 calc R . .
C13 C 0.3667(3) -0.0584(3) 0.2467(5) 0.0488(13) Uani 1 1 d . . .
C14 C 0.3581(3) -0.0645(4) 0.1055(6) 0.0579(15) Uani 1 1 d . . .
H14 H 0.3908 -0.0893 0.0601 0.069 Uiso 1 1 calc R . .
C15 C 0.2917(3) -0.0268(4) 0.0427(5) 0.0533(14) Uani 1 1 d . . .
C16 C 0.2579(3) -0.0149(5) -0.1108(5) 0.0797(19) Uani 1 1 d . . .
H16A H 0.2114 0.0131 -0.1237 0.120 Uiso 1 1 calc R . .
H16B H 0.2537 -0.0767 -0.1558 0.120 Uiso 1 1 calc R . .
H16C H 0.2870 0.0265 -0.1511 0.120 Uiso 1 1 calc R . .
C17 C 0.2665(3) -0.2042(4) 0.4158(7) 0.0790(19) Uani 1 1 d . . .
H17A H 0.2392 -0.1657 0.3404 0.118 Uiso 1 1 calc R . .
H17B H 0.2348 -0.2378 0.4601 0.118 Uiso 1 1 calc R . .
H17C H 0.2944 -0.2500 0.3799 0.118 Uiso 1 1 calc R . .
C18 C 0.3152(3) -0.1400(4) 0.5211(6) 0.0555(14) Uani 1 1 d . . .
C19 C 0.3627(3) -0.1638(4) 0.6432(6) 0.0622(15) Uani 1 1 d . . .
H19 H 0.3701 -0.2248 0.6831 0.075 Uiso 1 1 calc R . .
C20 C 0.3984(3) -0.0791(4) 0.6976(5) 0.0556(14) Uani 1 1 d . . .
C21 C 0.4582(3) -0.0670(4) 0.8248(6) 0.0760(18) Uani 1 1 d . . .
H21A H 0.4718 -0.0003 0.8352 0.114 Uiso 1 1 calc R . .
H21B H 0.4981 -0.1050 0.8156 0.114 Uiso 1 1 calc R . .
H21C H 0.4433 -0.0878 0.9055 0.114 Uiso 1 1 calc R . .
C22 C 0.2485(3) 0.1887(4) 0.5782(6) 0.0781(18) Uani 1 1 d . . .
H22A H 0.2230 0.1287 0.5639 0.117 Uiso 1 1 calc R . .
H22B H 0.2155 0.2411 0.5515 0.117 Uiso 1 1 calc R . .
H22C H 0.2731 0.1949 0.6752 0.117 Uiso 1 1 calc R . .
C23 C 0.3011(3) 0.1907(4) 0.4916(5) 0.0523(13) Uani 1 1 d . . .
C24 C 0.3475(3) 0.2619(4) 0.4810(6) 0.0641(16) Uani 1 1 d . . .
H24 H 0.3514 0.3218 0.5245 0.077 Uiso 1 1 calc R . .
C25 C 0.3883(3) 0.2288(4) 0.3931(5) 0.0540(14) Uani 1 1 d . . .
C26 C 0.4451(3) 0.2792(4) 0.3424(7) 0.0810(19) Uani 1 1 d . . .
H26A H 0.4631 0.2367 0.2826 0.121 Uiso 1 1 calc R . .
H26B H 0.4832 0.2973 0.4209 0.121 Uiso 1 1 calc R . .
H26C H 0.4255 0.3358 0.2910 0.121 Uiso 1 1 calc R . .
N1 N 0.0805(3) 0.1191(4) 0.0243(6) 0.0750(15) Uani 1 1 d . . .
N2 N 0.0205(3) 0.1160(4) 0.0757(6) 0.0757(15) Uani 1 1 d . . .
N3 N 0.1576(2) 0.0555(3) 0.2729(5) 0.0536(12) Uani 1 1 d . . .
H2 H 0.166(3) 0.069(4) 0.188(5) 0.064 Uiso 1 1 d . . .
N4 N 0.3037(2) -0.0199(3) 0.2627(4) 0.0433(10) Uani 1 1 d . . .
N5 N 0.2580(2) 0.0022(3) 0.1359(4) 0.0503(11) Uani 1 1 d . . .
N6 N 0.3229(2) -0.0426(3) 0.5066(4) 0.0452(10) Uani 1 1 d . . .
N7 N 0.3739(2) -0.0042(3) 0.6148(4) 0.0495(11) Uani 1 1 d . . .
N8 N 0.3143(2) 0.1173(3) 0.4077(4) 0.0443(10) Uani 1 1 d . . .
N9 N 0.3691(2) 0.1399(3) 0.3477(4) 0.0498(11) Uani 1 1 d . . .
O1 O -0.0307(2) 0.0725(4) 0.2489(5) 0.1058(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.484(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.323(8) . ?
C2 C3 1.403(9) . ?
C3 C4 1.341(10) . ?
C3 H3 0.9300 . ?
C4 N2 1.386(8) . ?
C4 C5 1.509(10) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O1 1.204(7) . ?
C6 N2 1.415(8) . ?
C6 C7 1.464(8) . ?
C7 C8 1.365(8) . ?
C7 N3 1.369(6) . ?
C8 C9 1.385(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(7) . ?
C9 H9 0.9300 . ?
C10 N3 1.359(6) . ?
C10 C11 1.505(7) . ?
C11 N4 1.462(6) . ?
C11 N6 1.471(6) . ?
C11 N8 1.472(6) . ?
C12 C13 1.492(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.365(6) . ?
C13 N4 1.378(6) . ?
C14 C15 1.383(7) . ?
C14 H14 0.9300 . ?
C15 N5 1.319(6) . ?
C15 C16 1.501(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.507(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.360(7) . ?
C18 N6 1.371(6) . ?
C19 C20 1.400(7) . ?
C19 H19 0.9300 . ?
C20 N7 1.333(6) . ?
C20 C21 1.488(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.487(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.359(7) . ?
C23 N8 1.377(6) . ?
C24 C25 1.391(7) . ?
C24 H24 0.9300 . ?
C25 N9 1.332(6) . ?
C25 C26 1.494(7) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 N2 1.382(7) . ?
N3 H2 0.91(5) . ?
N4 N5 1.374(5) . ?
N6 N7 1.368(5) . ?
N8 N9 1.377(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.2(7) . . ?
N1 C2 C1 121.5(6) . . ?
C3 C2 C1 128.3(8) . . ?
C4 C3 C2 108.3(7) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 N2 105.3(7) . . ?
C3 C4 C5 130.2(8) . . ?
N2 C4 C5 124.5(9) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N2 119.7(6) . . ?
O1 C6 C7 121.2(7) . . ?
N2 C6 C7 119.1(6) . . ?
C8 C7 N3 107.3(5) . . ?
C8 C7 C6 125.2(6) . . ?
N3 C7 C6 127.5(6) . . ?
C7 C8 C9 108.2(5) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
C10 C9 C8 107.6(5) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
N3 C10 C9 107.2(5) . . ?
N3 C10 C11 123.3(4) . . ?
C9 C10 C11 129.2(5) . . ?
N4 C11 N6 107.5(4) . . ?
N4 C11 N8 107.1(4) . . ?
N6 C11 N8 110.2(4) . . ?
N4 C11 C10 113.2(4) . . ?
N6 C11 C10 107.8(4) . . ?
N8 C11 C10 111.0(4) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N4 105.0(4) . . ?
C14 C13 C12 127.8(5) . . ?
N4 C13 C12 127.2(5) . . ?
C13 C14 C15 107.1(5) . . ?
C13 C14 H14 126.4 . . ?
C15 C14 H14 126.4 . . ?
N5 C15 C14 111.8(5) . . ?
N5 C15 C16 120.3(5) . . ?
C14 C15 C16 127.9(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N6 105.3(5) . . ?
C19 C18 C17 129.4(5) . . ?
N6 C18 C17 125.2(5) . . ?
C18 C19 C20 107.2(5) . . ?
C18 C19 H19 126.4 . . ?
C20 C19 H19 126.4 . . ?
N7 C20 C19 110.8(5) . . ?
N7 C20 C21 120.7(5) . . ?
C19 C20 C21 128.5(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N8 105.2(5) . . ?
C24 C23 C22 128.5(5) . . ?
N8 C23 C22 126.3(5) . . ?
C23 C24 C25 107.5(5) . . ?
C23 C24 H24 126.3 . . ?
C25 C24 H24 126.3 . . ?
N9 C25 C24 111.2(5) . . ?
N9 C25 C26 119.1(5) . . ?
C24 C25 C26 129.6(5) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 N1 N2 105.0(5) . . ?
N1 N2 C4 111.1(7) . . ?
N1 N2 C6 121.4(5) . . ?
C4 N2 C6 127.4(7) . . ?
C10 N3 C7 109.7(5) . . ?
C10 N3 H2 122(3) . . ?
C7 N3 H2 126(3) . . ?
N5 N4 C13 111.6(4) . . ?
N5 N4 C11 117.3(4) . . ?
C13 N4 C11 129.6(4) . . ?
C15 N5 N4 104.4(4) . . ?
N7 N6 C18 112.3(4) . . ?
N7 N6 C11 120.3(4) . . ?
C18 N6 C11 127.3(4) . . ?
C20 N7 N6 104.5(4) . . ?
N9 N8 C23 111.9(4) . . ?
N9 N8 C11 117.0(4) . . ?
C23 N8 C11 130.6(4) . . ?
C25 N9 N8 104.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.4(8) . . . . ?
C1 C2 C3 C4 178.1(7) . . . . ?
C2 C3 C4 N2 1.0(8) . . . . ?
C2 C3 C4 C5 -178.8(7) . . . . ?
O1 C6 C7 C8 3.7(10) . . . . ?
N2 C6 C7 C8 -175.3(6) . . . . ?
O1 C6 C7 N3 -175.8(6) . . . . ?
N2 C6 C7 N3 5.2(9) . . . . ?
N3 C7 C8 C9 -0.9(7) . . . . ?
C6 C7 C8 C9 179.5(5) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C8 C9 C10 N3 1.1(6) . . . . ?
C8 C9 C10 C11 175.3(5) . . . . ?
N3 C10 C11 N4 -53.4(6) . . . . ?
C9 C10 C11 N4 133.2(5) . . . . ?
N3 C10 C11 N6 -172.2(4) . . . . ?
C9 C10 C11 N6 14.5(7) . . . . ?
N3 C10 C11 N8 67.1(6) . . . . ?
C9 C10 C11 N8 -106.3(6) . . . . ?
N4 C13 C14 C15 1.8(5) . . . . ?
C12 C13 C14 C15 -175.9(5) . . . . ?
C13 C14 C15 N5 -0.2(6) . . . . ?
C13 C14 C15 C16 178.3(5) . . . . ?
N6 C18 C19 C20 -0.8(6) . . . . ?
C17 C18 C19 C20 175.8(5) . . . . ?
C18 C19 C20 N7 0.9(6) . . . . ?
C18 C19 C20 C21 -176.2(5) . . . . ?
N8 C23 C24 C25 -1.0(6) . . . . ?
C22 C23 C24 C25 176.9(5) . . . . ?
C23 C24 C25 N9 0.2(6) . . . . ?
C23 C24 C25 C26 177.6(5) . . . . ?
C3 C2 N1 N2 1.0(7) . . . . ?
C1 C2 N1 N2 -178.5(6) . . . . ?
C2 N1 N2 C4 -0.4(7) . . . . ?
C2 N1 N2 C6 178.5(5) . . . . ?
C3 C4 N2 N1 -0.4(8) . . . . ?
C5 C4 N2 N1 179.5(6) . . . . ?
C3 C4 N2 C6 -179.3(6) . . . . ?
C5 C4 N2 C6 0.6(10) . . . . ?
O1 C6 N2 N1 -176.1(5) . . . . ?
C7 C6 N2 N1 2.9(8) . . . . ?
O1 C6 N2 C4 2.6(10) . . . . ?
C7 C6 N2 C4 -178.4(5) . . . . ?
C9 C10 N3 C7 -1.7(6) . . . . ?
C11 C10 N3 C7 -176.3(5) . . . . ?
C8 C7 N3 C10 1.6(6) . . . . ?
C6 C7 N3 C10 -178.9(5) . . . . ?
C14 C13 N4 N5 -2.9(5) . . . . ?
C12 C13 N4 N5 174.9(5) . . . . ?
C14 C13 N4 C11 -168.2(4) . . . . ?
C12 C13 N4 C11 9.5(8) . . . . ?
N6 C11 N4 N5 157.8(4) . . . . ?
N8 C11 N4 N5 -83.8(5) . . . . ?
C10 C11 N4 N5 38.9(5) . . . . ?
N6 C11 N4 C13 -37.5(6) . . . . ?
N8 C11 N4 C13 80.9(5) . . . . ?
C10 C11 N4 C13 -156.4(5) . . . . ?
C14 C15 N5 N4 -1.5(5) . . . . ?
C16 C15 N5 N4 179.9(4) . . . . ?
C13 N4 N5 C15 2.7(5) . . . . ?
C11 N4 N5 C15 170.1(4) . . . . ?
C19 C18 N6 N7 0.4(6) . . . . ?
C17 C18 N6 N7 -176.3(5) . . . . ?
C19 C18 N6 C11 176.4(4) . . . . ?
C17 C18 N6 C11 -0.3(8) . . . . ?
N4 C11 N6 N7 117.1(4) . . . . ?
N8 C11 N6 N7 0.8(5) . . . . ?
C10 C11 N6 N7 -120.5(4) . . . . ?
N4 C11 N6 C18 -58.6(6) . . . . ?
N8 C11 N6 C18 -175.0(4) . . . . ?
C10 C11 N6 C18 63.8(6) . . . . ?
C19 C20 N7 N6 -0.6(5) . . . . ?
C21 C20 N7 N6 176.7(4) . . . . ?
C18 N6 N7 C20 0.1(5) . . . . ?
C11 N6 N7 C20 -176.2(4) . . . . ?
C24 C23 N8 N9 1.5(5) . . . . ?
C22 C23 N8 N9 -176.5(5) . . . . ?
C24 C23 N8 C11 172.8(4) . . . . ?
C22 C23 N8 C11 -5.2(8) . . . . ?
N4 C11 N8 N9 -23.2(5) . . . . ?
N6 C11 N8 N9 93.4(4) . . . . ?
C10 C11 N8 N9 -147.2(4) . . . . ?
N4 C11 N8 C23 165.9(4) . . . . ?
N6 C11 N8 C23 -77.5(6) . . . . ?
C10 C11 N8 C23 41.9(6) . . . . ?
C24 C25 N9 N8 0.7(5) . . . . ?
C26 C25 N9 N8 -177.0(4) . . . . ?
C23 N8 N9 C25 -1.4(5) . . . . ?
C11 N8 N9 C25 -173.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H2 N1 0.91(5) 2.13(5) 2.682(7) 118(4) .
N3 H2 N5 0.91(5) 2.18(5) 2.739(6) 119(4) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 998868'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H33 Cl2 N11 O2'
_chemical_formula_weight         698.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.1453(7)
_cell_length_b                   12.1246(10)
_cell_length_c                   18.4077(16)
_cell_angle_alpha                106.647(3)
_cell_angle_beta                 99.820(3)
_cell_angle_gamma                94.826(3)
_cell_volume                     1699.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20611
_cell_measurement_theta_min      1.18
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9457
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20611
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5978
_reflns_number_gt                3128
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0768P)²+0.7243P] 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         5978
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.5640(7) 0.1571(5) 0.5144(3) 0.0730(16) Uani 1 1 d . . .
H1A H 0.5852 0.1144 0.4651 0.110 Uiso 1 1 calc R . .
H1B H 0.5538 0.1058 0.5451 0.110 Uiso 1 1 calc R . .
H1C H 0.6555 0.2185 0.5406 0.110 Uiso 1 1 calc R . .
C2 C 0.4054(6) 0.2075(4) 0.5026(2) 0.0488(12) Uani 1 1 d . . .
C3 C 0.3242(6) 0.2762(4) 0.5567(2) 0.0492(12) Uani 1 1 d . . .
H3 H 0.3563 0.2966 0.6103 0.059 Uiso 1 1 calc R . .
C4 C 0.1901(5) 0.3074(4) 0.5163(2) 0.0411(11) Uani 1 1 d . . .
C5 C 0.0616(6) 0.3798(4) 0.5427(2) 0.0583(14) Uani 1 1 d . . .
H5A H -0.0166 0.3839 0.4985 0.087 Uiso 1 1 calc R . .
H5B H 0.1155 0.4566 0.5730 0.087 Uiso 1 1 calc R . .
H5C H 0.0026 0.3458 0.5737 0.087 Uiso 1 1 calc R . .
C6 C -0.0536(7) 0.0593(4) 0.4310(3) 0.0645(15) Uani 1 1 d . . .
H6A H 0.0315 0.1214 0.4640 0.097 Uiso 1 1 calc R . .
H6B H -0.0100 -0.0133 0.4239 0.097 Uiso 1 1 calc R . .
H6C H -0.1499 0.0574 0.4545 0.097 Uiso 1 1 calc R . .
C7 C -0.1036(6) 0.0787(4) 0.3548(2) 0.0449(11) Uani 1 1 d . . .
C8 C -0.2194(6) 0.0113(4) 0.2923(3) 0.0507(12) Uani 1 1 d . . .
H8 H -0.2840 -0.0577 0.2889 0.061 Uiso 1 1 calc R . .
C9 C -0.2240(6) 0.0638(4) 0.2342(3) 0.0502(12) Uani 1 1 d . . .
C10 C -0.3268(7) 0.0256(5) 0.1540(3) 0.0722(17) Uani 1 1 d . . .
H10A H -0.3012 0.0815 0.1282 0.108 Uiso 1 1 calc R . .
H10B H -0.4442 0.0195 0.1560 0.108 Uiso 1 1 calc R . .
H10C H -0.3014 -0.0487 0.1261 0.108 Uiso 1 1 calc R . .
C11 C 0.0829(5) 0.2664(4) 0.3739(2) 0.0372(10) Uani 1 1 d . . .
C12 C 0.1165(5) 0.3597(4) 0.3497(2) 0.0368(10) Uani 1 1 d . . .
C13 C 0.2526(5) 0.4547(4) 0.3863(2) 0.0416(11) Uani 1 1 d . . .
H13 H 0.3271 0.4651 0.4328 0.050 Uiso 1 1 calc R . .
C14 C 0.2535(5) 0.5250(4) 0.3419(2) 0.0402(11) Uani 1 1 d . . .
H14 H 0.3294 0.5920 0.3526 0.048 Uiso 1 1 calc R . .
C15 C 0.1174(5) 0.4801(4) 0.2748(2) 0.0346(10) Uani 1 1 d . . .
C16 C 0.0840(5) 0.5251(4) 0.2159(2) 0.0382(10) Uani 1 1 d . . .
C17 C -0.3253(7) 0.2269(5) 0.0283(3) 0.0728(16) Uani 1 1 d . . .
H17A H -0.2971 0.1767 0.0591 0.109 Uiso 1 1 calc R . .
H17B H -0.3021 0.1942 -0.0224 0.109 Uiso 1 1 calc R . .
H17C H -0.4427 0.2345 0.0237 0.109 Uiso 1 1 calc R . .
C18 C -0.2238(6) 0.3425(4) 0.0656(2) 0.0498(12) Uani 1 1 d . . .
C19 C -0.2242(6) 0.4408(4) 0.0396(3) 0.0535(13) Uani 1 1 d . . .
H19 H -0.2916 0.4465 -0.0049 0.064 Uiso 1 1 calc R . .
C20 C -0.1070(6) 0.5262(4) 0.0921(2) 0.0453(12) Uani 1 1 d . . .
C21 C -0.0557(6) 0.6463(4) 0.0908(3) 0.0585(14) Uani 1 1 d . . .
H21A H 0.0297 0.6862 0.1358 0.088 Uiso 1 1 calc R . .
H21B H -0.1515 0.6873 0.0908 0.088 Uiso 1 1 calc R . .
H21C H -0.0123 0.6427 0.0450 0.088 Uiso 1 1 calc R . .
C22 C 0.0836(7) 0.7838(4) 0.2999(3) 0.0673(15) Uani 1 1 d . . .
H22A H 0.0013 0.7216 0.2989 0.101 Uiso 1 1 calc R . .
H22B H 0.0289 0.8374 0.2780 0.101 Uiso 1 1 calc R . .
H22C H 0.1395 0.8236 0.3525 0.101 Uiso 1 1 calc R . .
C23 C 0.2098(6) 0.7355(4) 0.2539(2) 0.0455(12) Uani 1 1 d . . .
C24 C 0.3477(6) 0.7873(4) 0.2380(3) 0.0519(13) Uani 1 1 d . . .
H24 H 0.3888 0.8662 0.2559 0.062 Uiso 1 1 calc R . .
C25 C 0.4164(6) 0.6997(4) 0.1897(3) 0.0450(11) Uani 1 1 d . . .
C26 C 0.5694(6) 0.7058(4) 0.1563(3) 0.0635(15) Uani 1 1 d . . .
H26A H 0.5812 0.6294 0.1255 0.095 Uiso 1 1 calc R . .
H26B H 0.6666 0.7357 0.1974 0.095 Uiso 1 1 calc R . .
H26C H 0.5593 0.7561 0.1244 0.095 Uiso 1 1 calc R . .
C27 C 0.2598(6) 0.1982(4) 0.1255(2) 0.0436(11) Uani 1 1 d . . .
C28 C 0.3564(6) 0.3076(4) 0.1499(2) 0.0411(11) Uani 1 1 d . . .
C29 C 0.4662(5) 0.3403(4) 0.2214(2) 0.0403(11) Uani 1 1 d . . .
C30 C 0.4693(5) 0.2679(4) 0.2700(2) 0.0422(11) Uani 1 1 d . . .
C31 C 0.3651(6) 0.1628(4) 0.2470(2) 0.0411(11) Uani 1 1 d . . .
C32 C 0.2632(5) 0.1268(4) 0.1722(2) 0.0420(11) Uani 1 1 d . . .
C33 C 0.5843(6) 0.3050(4) 0.3444(3) 0.0483(12) Uani 1 1 d . . .
C34 C 0.5806(6) 0.4473(4) 0.2459(2) 0.0471(12) Uani 1 1 d . . .
N1 N 0.3254(4) 0.5971(3) 0.17588(19) 0.0414(9) Uani 1 1 d . . .
N2 N 0.1975(4) 0.6202(3) 0.21598(19) 0.0387(9) Uani 1 1 d . . .
N3 N -0.0408(4) 0.4776(3) 0.14776(19) 0.0416(9) Uani 1 1 d . . .
N4 N -0.1140(5) 0.3648(3) 0.13171(19) 0.0480(10) Uani 1 1 d . . .
N5 N 0.0347(4) 0.3827(3) 0.28429(19) 0.0394(9) Uani 1 1 d . . .
H5N H -0.039(5) 0.335(4) 0.249(2) 0.047 Uiso 1 1 d . . .
N6 N -0.1152(5) 0.1612(3) 0.25834(19) 0.0487(10) Uani 1 1 d . . .
N7 N -0.0391(4) 0.1693(3) 0.33260(19) 0.0424(9) Uani 1 1 d . . .
N8 N 0.1890(4) 0.2579(3) 0.44057(18) 0.0378(9) Uani 1 1 d . . .
N9 N 0.3224(4) 0.1960(3) 0.43127(19) 0.0435(9) Uani 1 1 d . . .
N10 N 0.6750(5) 0.3350(4) 0.4024(2) 0.0667(13) Uani 1 1 d . . .
N11 N 0.6762(5) 0.5300(4) 0.2660(2) 0.0597(12) Uani 1 1 d . . .
O1 O 0.3652(4) 0.0907(3) 0.29061(18) 0.0535(9) Uani 1 1 d . . .
H1O H 0.363(5) 0.127(4) 0.347(3) 0.064 Uiso 1 1 d . . .
O2 O 0.3445(4) 0.3737(3) 0.10266(17) 0.0533(9) Uani 1 1 d . . .
H2O H 0.347(6) 0.451(4) 0.128(3) 0.064 Uiso 1 1 d . . .
Cl1 Cl 0.14406(17) -0.00801(10) 0.14176(7) 0.0629(4) Uani 1 1 d . . .
Cl2 Cl 0.13341(17) 0.15121(11) 0.03429(6) 0.0650(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.484(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N9 1.333(5) . ?
C2 C3 1.401(6) . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 N8 1.349(5) . ?
C4 C5 1.479(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.484(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.357(6) . ?
C7 N7 1.371(5) . ?
C8 C9 1.389(6) . ?
C8 H8 0.9300 . ?
C9 N6 1.329(5) . ?
C9 C10 1.489(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.353(6) . ?
C11 N7 1.409(5) . ?
C11 N8 1.411(5) . ?
C12 N5 1.387(5) . ?
C12 C13 1.448(6) . ?
C13 C14 1.339(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.448(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.345(5) . ?
C15 N5 1.380(5) . ?
C16 N3 1.411(5) . ?
C16 N2 1.416(5) . ?
C17 C18 1.477(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N4 1.324(5) . ?
C18 C19 1.405(6) . ?
C19 C20 1.365(6) . ?
C19 H19 0.9300 . ?
C20 N3 1.378(5) . ?
C20 C21 1.489(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.495(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.356(6) . ?
C23 N2 1.358(5) . ?
C24 C25 1.400(6) . ?
C24 H24 0.9300 . ?
C25 N1 1.327(5) . ?
C25 C26 1.486(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C32 1.381(6) . ?
C27 C28 1.394(6) . ?
C27 Cl2 1.723(4) . ?
C28 O2 1.339(5) . ?
C28 C29 1.389(5) . ?
C29 C30 1.420(6) . ?
C29 C34 1.440(6) . ?
C30 C31 1.383(6) . ?
C30 C33 1.447(6) . ?
C31 O1 1.345(5) . ?
C31 C32 1.407(6) . ?
C32 Cl1 1.717(4) . ?
C33 N10 1.132(5) . ?
C34 N11 1.143(5) . ?
N1 N2 1.379(5) . ?
N3 N4 1.373(5) . ?
N5 H5N 0.84(4) . ?
N6 N7 1.373(4) . ?
N8 N9 1.379(4) . ?
O1 H1O 1.00(5) . ?
O2 H2O 0.92(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N9 C2 C3 109.3(4) . . ?
N9 C2 C1 120.4(4) . . ?
C3 C2 C1 130.3(4) . . ?
C4 C3 C2 107.3(4) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
N8 C4 C3 106.7(4) . . ?
N8 C4 C5 122.1(4) . . ?
C3 C4 C5 131.1(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N7 105.5(4) . . ?
C8 C7 C6 128.0(4) . . ?
N7 C7 C6 126.5(4) . . ?
C7 C8 C9 107.7(4) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
N6 C9 C8 110.4(4) . . ?
N6 C9 C10 119.7(4) . . ?
C8 C9 C10 129.8(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N7 124.8(4) . . ?
C12 C11 N8 118.4(4) . . ?
N7 C11 N8 116.4(4) . . ?
C11 C12 N5 128.1(4) . . ?
C11 C12 C13 126.2(4) . . ?
N5 C12 C13 105.6(4) . . ?
C14 C13 C12 108.6(4) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
C13 C14 C15 109.2(4) . . ?
C13 C14 H14 125.4 . . ?
C15 C14 H14 125.4 . . ?
C16 C15 N5 128.6(4) . . ?
C16 C15 C14 126.0(4) . . ?
N5 C15 C14 105.4(3) . . ?
C15 C16 N3 126.4(4) . . ?
C15 C16 N2 117.8(4) . . ?
N3 C16 N2 115.2(3) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C19 110.7(4) . . ?
N4 C18 C17 121.1(4) . . ?
C19 C18 C17 128.1(4) . . ?
C20 C19 C18 107.1(4) . . ?
C20 C19 H19 126.5 . . ?
C18 C19 H19 126.5 . . ?
C19 C20 N3 105.4(4) . . ?
C19 C20 C21 128.7(4) . . ?
N3 C20 C21 126.0(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N2 106.2(4) . . ?
C24 C23 C22 131.8(4) . . ?
N2 C23 C22 122.0(4) . . ?
C23 C24 C25 107.2(4) . . ?
C23 C24 H24 126.4 . . ?
C25 C24 H24 126.4 . . ?
N1 C25 C24 110.2(4) . . ?
N1 C25 C26 119.2(4) . . ?
C24 C25 C26 130.6(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 122.0(4) . . ?
C32 C27 Cl2 119.4(3) . . ?
C28 C27 Cl2 118.6(3) . . ?
O2 C28 C29 123.3(4) . . ?
O2 C28 C27 119.1(4) . . ?
C29 C28 C27 117.6(4) . . ?
C28 C29 C30 120.6(4) . . ?
C28 C29 C34 119.8(4) . . ?
C30 C29 C34 119.6(4) . . ?
C31 C30 C29 120.9(4) . . ?
C31 C30 C33 119.9(4) . . ?
C29 C30 C33 119.2(4) . . ?
O1 C31 C30 123.0(4) . . ?
O1 C31 C32 119.0(4) . . ?
C30 C31 C32 117.9(4) . . ?
C27 C32 C31 120.7(4) . . ?
C27 C32 Cl1 121.7(3) . . ?
C31 C32 Cl1 117.5(3) . . ?
N10 C33 C30 179.3(6) . . ?
N11 C34 C29 177.5(5) . . ?
C25 N1 N2 105.1(3) . . ?
C23 N2 N1 111.3(3) . . ?
C23 N2 C16 130.4(4) . . ?
N1 N2 C16 118.1(3) . . ?
N4 N3 C20 111.6(3) . . ?
N4 N3 C16 117.7(3) . . ?
C20 N3 C16 130.7(4) . . ?
C18 N4 N3 105.2(4) . . ?
C15 N5 C12 110.9(3) . . ?
C15 N5 H5N 123(3) . . ?
C12 N5 H5N 124(3) . . ?
C9 N6 N7 105.1(3) . . ?
C7 N7 N6 111.3(3) . . ?
C7 N7 C11 130.7(3) . . ?
N6 N7 C11 117.9(3) . . ?
C4 N8 N9 110.9(3) . . ?
C4 N8 C11 130.6(4) . . ?
N9 N8 C11 118.5(3) . . ?
C2 N9 N8 105.8(3) . . ?
C31 O1 H1O 116(3) . . ?
C28 O2 H2O 113(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
N9 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 175.3(5) . . . . ?
C2 C3 C4 N8 0.8(5) . . . . ?
C2 C3 C4 C5 -179.4(5) . . . . ?
N7 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C9 179.8(5) . . . . ?
C7 C8 C9 N6 0.1(6) . . . . ?
C7 C8 C9 C10 179.1(5) . . . . ?
N7 C11 C12 N5 4.3(7) . . . . ?
N8 C11 C12 N5 176.6(4) . . . . ?
N7 C11 C12 C13 -172.8(4) . . . . ?
N8 C11 C12 C13 -0.5(7) . . . . ?
C11 C12 C13 C14 174.7(4) . . . . ?
N5 C12 C13 C14 -2.9(5) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -176.9(4) . . . . ?
C13 C14 C15 N5 2.1(5) . . . . ?
N5 C15 C16 N3 -3.5(7) . . . . ?
C14 C15 C16 N3 175.3(4) . . . . ?
N5 C15 C16 N2 -174.2(4) . . . . ?
C14 C15 C16 N2 4.6(6) . . . . ?
N4 C18 C19 C20 0.9(6) . . . . ?
C17 C18 C19 C20 -178.5(5) . . . . ?
C18 C19 C20 N3 -0.3(5) . . . . ?
C18 C19 C20 C21 178.6(5) . . . . ?
N2 C23 C24 C25 0.1(5) . . . . ?
C22 C23 C24 C25 -178.0(5) . . . . ?
C23 C24 C25 N1 0.0(5) . . . . ?
C23 C24 C25 C26 -178.1(5) . . . . ?
C32 C27 C28 O2 -178.5(4) . . . . ?
Cl2 C27 C28 O2 1.7(6) . . . . ?
C32 C27 C28 C29 4.3(7) . . . . ?
Cl2 C27 C28 C29 -175.6(3) . . . . ?
O2 C28 C29 C30 178.0(4) . . . . ?
C27 C28 C29 C30 -4.8(6) . . . . ?
O2 C28 C29 C34 -3.3(7) . . . . ?
C27 C28 C29 C34 173.8(4) . . . . ?
C28 C29 C30 C31 0.9(7) . . . . ?
C34 C29 C30 C31 -177.7(4) . . . . ?
C28 C29 C30 C33 -179.5(4) . . . . ?
C34 C29 C30 C33 1.8(6) . . . . ?
C29 C30 C31 O1 179.1(4) . . . . ?
C33 C30 C31 O1 -0.4(7) . . . . ?
C29 C30 C31 C32 3.6(6) . . . . ?
C33 C30 C31 C32 -176.0(4) . . . . ?
C28 C27 C32 C31 0.3(7) . . . . ?
Cl2 C27 C32 C31 -179.9(3) . . . . ?
C28 C27 C32 Cl1 -180.0(3) . . . . ?
Cl2 C27 C32 Cl1 -0.2(5) . . . . ?
O1 C31 C32 C27 -179.9(4) . . . . ?
C30 C31 C32 C27 -4.2(6) . . . . ?
O1 C31 C32 Cl1 0.3(6) . . . . ?
C30 C31 C32 Cl1 176.0(3) . . . . ?
C31 C30 C33 N10 175(100) . . . . ?
C29 C30 C33 N10 -5(50) . . . . ?
C28 C29 C34 N11 -131(11) . . . . ?
C30 C29 C34 N11 47(12) . . . . ?
C24 C25 N1 N2 0.0(5) . . . . ?
C26 C25 N1 N2 178.3(4) . . . . ?
C24 C23 N2 N1 -0.1(5) . . . . ?
C22 C23 N2 N1 178.3(4) . . . . ?
C24 C23 N2 C16 175.7(4) . . . . ?
C22 C23 N2 C16 -5.9(7) . . . . ?
C25 N1 N2 C23 0.1(4) . . . . ?
C25 N1 N2 C16 -176.3(3) . . . . ?
C15 C16 N2 C23 -82.0(6) . . . . ?
N3 C16 N2 C23 106.3(5) . . . . ?
C15 C16 N2 N1 93.5(5) . . . . ?
N3 C16 N2 N1 -78.2(5) . . . . ?
C19 C20 N3 N4 -0.4(5) . . . . ?
C21 C20 N3 N4 -179.3(4) . . . . ?
C19 C20 N3 C16 -179.6(4) . . . . ?
C21 C20 N3 C16 1.4(8) . . . . ?
C15 C16 N3 N4 -13.7(6) . . . . ?
N2 C16 N3 N4 157.2(3) . . . . ?
C15 C16 N3 C20 165.5(4) . . . . ?
N2 C16 N3 C20 -23.6(6) . . . . ?
C19 C18 N4 N3 -1.1(5) . . . . ?
C17 C18 N4 N3 178.4(4) . . . . ?
C20 N3 N4 C18 0.9(5) . . . . ?
C16 N3 N4 C18 -179.7(4) . . . . ?
C16 C15 N5 C12 174.9(4) . . . . ?
C14 C15 N5 C12 -4.0(5) . . . . ?
C11 C12 N5 C15 -173.2(4) . . . . ?
C13 C12 N5 C15 4.3(5) . . . . ?
C8 C9 N6 N7 0.8(5) . . . . ?
C10 C9 N6 N7 -178.4(4) . . . . ?
C8 C7 N7 N6 1.5(5) . . . . ?
C6 C7 N7 N6 -179.3(4) . . . . ?
C8 C7 N7 C11 178.9(4) . . . . ?
C6 C7 N7 C11 -1.8(8) . . . . ?
C9 N6 N7 C7 -1.4(5) . . . . ?
C9 N6 N7 C11 -179.2(4) . . . . ?
C12 C11 N7 C7 -168.7(4) . . . . ?
N8 C11 N7 C7 18.8(7) . . . . ?
C12 C11 N7 N6 8.6(6) . . . . ?
N8 C11 N7 N6 -163.9(4) . . . . ?
C3 C4 N8 N9 -0.7(5) . . . . ?
C5 C4 N8 N9 179.4(4) . . . . ?
C3 C4 N8 C11 -176.5(4) . . . . ?
C5 C4 N8 C11 3.6(7) . . . . ?
C12 C11 N8 C4 82.0(6) . . . . ?
N7 C11 N8 C4 -105.0(5) . . . . ?
C12 C11 N8 N9 -93.5(5) . . . . ?
N7 C11 N8 N9 79.4(5) . . . . ?
C3 C2 N9 N8 0.2(5) . . . . ?
C1 C2 N9 N8 -176.3(4) . . . . ?
C4 N8 N9 C2 0.4(5) . . . . ?
C11 N8 N9 C2 176.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5N N6 0.84(4) 2.21(4) 2.730(5) 120(4) .
N5 H5N N4 0.84(4) 2.28(4) 2.801(5) 121(4) .
O1 H1O N9 1.00(5) 1.65(5) 2.635(5) 168(4) .
O1 H1O N8 1.00(5) 2.68(5) 3.525(5) 142(3) .
O2 H2O N1 0.92(5) 1.77(5) 2.688(5) 173(4) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 998869'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6
# start Validation Reply Form
_vrf_RINTA01_6                   
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.220       
RESPONSE: The crystal did not diffract in higher angles.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H31 N9'
_chemical_formula_weight         469.60

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   23.991(4)
_cell_length_b                   8.3841(13)
_cell_length_c                   25.825(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5194.6(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8778
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60401
_diffrn_reflns_av_R_equivalents  0.2203
_diffrn_reflns_av_sigmaI/netI    0.1392
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.36
_reflns_number_total             9046
_reflns_number_gt                4430
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0607P)²+4.1431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   6(4)
_refine_ls_number_reflns         9046
_refine_ls_number_parameters     638
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2220
_refine_ls_R_factor_gt           0.0994
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.0944(4) 0.1060(11) 0.1344(4) 0.084(3) Uani 1 1 d . . .
H1A H 0.1301 0.1549 0.1289 0.126 Uiso 1 1 calc R . .
H1B H 0.0797 0.0697 0.1019 0.126 Uiso 1 1 calc R . .
H1C H 0.0985 0.0170 0.1575 0.126 Uiso 1 1 calc R . .
C2 C 0.0549(4) 0.2268(10) 0.1580(3) 0.058(2) Uani 1 1 d . . .
C3 C 0.0000(4) 0.2045(10) 0.1742(4) 0.067(3) Uani 1 1 d . . .
H3 H -0.0206 0.1106 0.1728 0.080 Uiso 1 1 calc R . .
C4 C -0.0171(4) 0.3482(10) 0.1921(3) 0.062(2) Uani 1 1 d . . .
C5 C -0.0715(4) 0.3998(11) 0.2155(4) 0.093(3) Uani 1 1 d . . .
H5A H -0.0701 0.5119 0.2230 0.140 Uiso 1 1 calc R . .
H5B H -0.0780 0.3414 0.2469 0.140 Uiso 1 1 calc R . .
H5C H -0.1012 0.3792 0.1915 0.140 Uiso 1 1 calc R . .
C6 C -0.0110(5) 0.6629(12) 0.0906(4) 0.094(3) Uani 1 1 d . . .
H6A H 0.0230 0.6097 0.0998 0.141 Uiso 1 1 calc R . .
H6B H -0.0030 0.7484 0.0670 0.141 Uiso 1 1 calc R . .
H6C H -0.0359 0.5884 0.0743 0.141 Uiso 1 1 calc R . .
C7 C -0.0380(4) 0.7293(9) 0.1385(3) 0.056(2) Uani 1 1 d . . .
C8 C -0.0842(4) 0.8157(10) 0.1456(4) 0.067(2) Uani 1 1 d . . .
H8 H -0.1091 0.8481 0.1201 0.081 Uiso 1 1 calc R . .
C9 C -0.0882(3) 0.8481(9) 0.1984(3) 0.054(2) Uani 1 1 d . . .
C10 C -0.1312(4) 0.9418(10) 0.2272(4) 0.078(3) Uani 1 1 d . . .
H10A H -0.1223 0.9419 0.2635 0.117 Uiso 1 1 calc R . .
H10B H -0.1671 0.8941 0.2222 0.117 Uiso 1 1 calc R . .
H10C H -0.1317 1.0494 0.2146 0.117 Uiso 1 1 calc R . .
C11 C 0.0309(3) 0.6140(9) 0.2002(3) 0.047(2) Uani 1 1 d . . .
C12 C 0.0747(3) 0.6691(8) 0.2266(3) 0.045(2) Uani 1 1 d . . .
C13 C 0.0866(3) 0.8297(9) 0.2444(3) 0.056(2) Uani 1 1 d . . .
H13 H 0.0656 0.9202 0.2370 0.068 Uiso 1 1 calc R . .
C14 C 0.1338(3) 0.8253(9) 0.2737(3) 0.051(2) Uani 1 1 d . . .
H14 H 0.1495 0.9119 0.2908 0.061 Uiso 1 1 calc R . .
C15 C 0.1554(3) 0.6668(8) 0.2739(3) 0.0410(19) Uani 1 1 d . . .
C16 C 0.2010(3) 0.6095(8) 0.2993(3) 0.0454(19) Uani 1 1 d . . .
C17 C 0.1623(4) 0.7484(10) 0.4030(4) 0.070(3) Uani 1 1 d . . .
H17A H 0.1395 0.6837 0.3808 0.105 Uiso 1 1 calc R . .
H17B H 0.1449 0.8505 0.4078 0.105 Uiso 1 1 calc R . .
H17C H 0.1664 0.6967 0.4360 0.105 Uiso 1 1 calc R . .
C18 C 0.2180(3) 0.7706(8) 0.3790(3) 0.048(2) Uani 1 1 d . . .
C19 C 0.2651(3) 0.8524(9) 0.3952(3) 0.053(2) Uani 1 1 d . . .
H19 H 0.2692 0.9108 0.4256 0.064 Uiso 1 1 calc R . .
C20 C 0.3053(3) 0.8294(9) 0.3568(3) 0.048(2) Uani 1 1 d . . .
C21 C 0.3643(3) 0.8940(12) 0.3548(4) 0.083(3) Uani 1 1 d . . .
H21A H 0.3820 0.8591 0.3235 0.125 Uiso 1 1 calc R . .
H21B H 0.3849 0.8554 0.3841 0.125 Uiso 1 1 calc R . .
H21C H 0.3633 1.0085 0.3556 0.125 Uiso 1 1 calc R . .
C22 C 0.2459(3) 0.3858(10) 0.3848(3) 0.071(3) Uani 1 1 d . . .
H22A H 0.2339 0.4935 0.3907 0.107 Uiso 1 1 calc R . .
H22B H 0.2840 0.3743 0.3957 0.107 Uiso 1 1 calc R . .
H22C H 0.2228 0.3141 0.4043 0.107 Uiso 1 1 calc R . .
C23 C 0.2413(3) 0.3478(9) 0.3285(3) 0.049(2) Uani 1 1 d . . .
C24 C 0.2530(4) 0.2122(9) 0.3016(4) 0.062(3) Uani 1 1 d . . .
H24 H 0.2682 0.1188 0.3148 0.074 Uiso 1 1 calc R . .
C25 C 0.2376(3) 0.2404(9) 0.2505(4) 0.052(2) Uani 1 1 d . . .
C26 C 0.2424(4) 0.1268(11) 0.2058(4) 0.092(3) Uani 1 1 d . . .
H26A H 0.2293 0.1777 0.1748 0.138 Uiso 1 1 calc R . .
H26B H 0.2203 0.0336 0.2126 0.138 Uiso 1 1 calc R . .
H26C H 0.2807 0.0964 0.2014 0.138 Uiso 1 1 calc R . .
C27 C -0.1688(5) 0.1676(11) 0.1013(4) 0.105(4) Uani 1 1 d . . .
H27A H -0.1354 0.2182 0.1135 0.157 Uiso 1 1 calc R . .
H27B H -0.1593 0.0854 0.0770 0.157 Uiso 1 1 calc R . .
H27C H -0.1885 0.1215 0.1300 0.157 Uiso 1 1 calc R . .
C28 C -0.2054(5) 0.2897(11) 0.0751(4) 0.073(3) Uani 1 1 d . . .
C29 C -0.2586(5) 0.2671(11) 0.0552(4) 0.079(3) Uani 1 1 d . . .
H29 H -0.2787 0.1722 0.0550 0.095 Uiso 1 1 calc R . .
C30 C -0.2758(4) 0.4107(10) 0.0361(3) 0.063(2) Uani 1 1 d . . .
C31 C -0.3279(4) 0.4620(11) 0.0097(4) 0.088(3) Uani 1 1 d . . .
H31A H -0.3258 0.5739 0.0020 0.132 Uiso 1 1 calc R . .
H31B H -0.3592 0.4421 0.0319 0.132 Uiso 1 1 calc R . .
H31C H -0.3323 0.4031 -0.0219 0.132 Uiso 1 1 calc R . .
C32 C -0.2635(4) 0.7560(11) 0.1381(4) 0.083(3) Uani 1 1 d . . .
H32A H -0.2303 0.6979 0.1296 0.125 Uiso 1 1 calc R . .
H32B H -0.2884 0.6882 0.1571 0.125 Uiso 1 1 calc R . .
H32C H -0.2540 0.8470 0.1588 0.125 Uiso 1 1 calc R . .
C33 C -0.2906(4) 0.8088(9) 0.0907(4) 0.056(2) Uani 1 1 d . . .
C34 C -0.3389(3) 0.8961(9) 0.0819(3) 0.061(2) Uani 1 1 d . . .
H34 H -0.3632 0.9353 0.1068 0.073 Uiso 1 1 calc R . .
C35 C -0.3439(3) 0.9137(8) 0.0284(3) 0.054(2) Uani 1 1 d . . .
C36 C -0.3887(3) 1.0005(11) -0.0003(4) 0.079(3) Uani 1 1 d . . .
H36A H -0.3820 0.9931 -0.0368 0.118 Uiso 1 1 calc R . .
H36B H -0.3888 1.1106 0.0100 0.118 Uiso 1 1 calc R . .
H36C H -0.4242 0.9536 0.0077 0.118 Uiso 1 1 calc R . .
C37 C -0.2262(3) 0.6723(9) 0.0302(3) 0.048(2) Uani 1 1 d . . .
C38 C -0.1805(3) 0.7197(8) 0.0032(3) 0.046(2) Uani 1 1 d . . .
C39 C -0.1668(3) 0.8727(8) -0.0175(3) 0.054(2) Uani 1 1 d . . .
H39 H -0.1872 0.9659 -0.0127 0.064 Uiso 1 1 calc R . .
C40 C -0.1197(3) 0.8595(9) -0.0448(3) 0.056(2) Uani 1 1 d . . .
H40 H -0.1016 0.9431 -0.0615 0.067 Uiso 1 1 calc R . .
C41 C -0.1014(3) 0.6968(8) -0.0446(3) 0.043(2) Uani 1 1 d . . .
C42 C -0.0571(3) 0.6313(9) -0.0696(3) 0.048(2) Uani 1 1 d . . .
C43 C -0.0225(4) 0.1491(10) 0.0254(4) 0.092(3) Uani 1 1 d . . .
H43A H -0.0371 0.2004 0.0557 0.138 Uiso 1 1 calc R . .
H43B H 0.0156 0.1192 0.0313 0.138 Uiso 1 1 calc R . .
H43C H -0.0442 0.0555 0.0179 0.138 Uiso 1 1 calc R . .
C44 C -0.0254(3) 0.2600(9) -0.0189(4) 0.054(2) Uani 1 1 d . . .
C45 C -0.0077(4) 0.2315(9) -0.0703(4) 0.059(3) Uani 1 1 d . . .
H45 H 0.0075 0.1375 -0.0831 0.070 Uiso 1 1 calc R . .
C46 C -0.0174(3) 0.3682(10) -0.0973(3) 0.053(2) Uani 1 1 d . . .
C47 C -0.0086(3) 0.4056(10) -0.1537(3) 0.066(2) Uani 1 1 d . . .
H47A H -0.0195 0.5138 -0.1604 0.099 Uiso 1 1 calc R . .
H47B H -0.0307 0.3348 -0.1744 0.099 Uiso 1 1 calc R . .
H47C H 0.0301 0.3922 -0.1622 0.099 Uiso 1 1 calc R . .
C48 C 0.1097(4) 0.8930(12) -0.1278(4) 0.096(3) Uani 1 1 d . . .
H48A H 0.1266 0.8544 -0.0966 0.144 Uiso 1 1 calc R . .
H48B H 0.1115 1.0074 -0.1285 0.144 Uiso 1 1 calc R . .
H48C H 0.1293 0.8506 -0.1572 0.144 Uiso 1 1 calc R . .
C49 C 0.0499(4) 0.8409(10) -0.1298(4) 0.060(2) Uani 1 1 d . . .
C50 C 0.0089(3) 0.8688(9) -0.1669(3) 0.054(2) Uani 1 1 d . . .
H50 H 0.0125 0.9276 -0.1973 0.065 Uiso 1 1 calc R . .
C51 C -0.0382(3) 0.7910(9) -0.1492(4) 0.051(2) Uani 1 1 d . . .
C52 C -0.0935(3) 0.7732(10) -0.1741(4) 0.066(3) Uani 1 1 d . . .
H52A H -0.1177 0.7137 -0.1517 0.099 Uiso 1 1 calc R . .
H52B H -0.0893 0.7175 -0.2063 0.099 Uiso 1 1 calc R . .
H52C H -0.1092 0.8767 -0.1804 0.099 Uiso 1 1 calc R . .
N1 N 0.0722(3) 0.3740(8) 0.1650(3) 0.0568(18) Uani 1 1 d . . .
N2 N 0.0266(3) 0.4502(7) 0.1859(2) 0.0478(16) Uani 1 1 d . . .
N3 N -0.0149(3) 0.7112(7) 0.1866(3) 0.0510(18) Uani 1 1 d . . .
N4 N -0.0452(3) 0.7845(7) 0.2249(3) 0.0544(18) Uani 1 1 d . . .
N5 N 0.1185(3) 0.5760(7) 0.2449(2) 0.0495(17) Uani 1 1 d . . .
H2 H 0.129(3) 0.477(8) 0.232(3) 0.059 Uiso 1 1 d . . .
N6 N 0.2322(2) 0.7102(7) 0.3322(3) 0.0434(16) Uani 1 1 d . . .
N7 N 0.2862(3) 0.7443(7) 0.3184(3) 0.0511(19) Uani 1 1 d . . .
N8 N 0.2200(2) 0.4518(7) 0.2928(3) 0.0491(16) Uani 1 1 d . . .
N9 N 0.2185(3) 0.3853(7) 0.2437(2) 0.0520(17) Uani 1 1 d . . .
N10 N -0.1885(3) 0.4364(8) 0.0696(2) 0.0611(18) Uani 1 1 d . . .
N11 N -0.2324(3) 0.5132(7) 0.0454(2) 0.0526(17) Uani 1 1 d . . .
N12 N -0.2697(3) 0.7780(7) 0.0424(3) 0.0476(18) Uani 1 1 d . . .
N13 N -0.3032(3) 0.8409(7) 0.0031(2) 0.0533(18) Uani 1 1 d . . .
N14 N -0.1396(3) 0.6171(7) -0.0147(3) 0.0469(17) Uani 1 1 d . . .
H1 H -0.131(3) 0.529(8) -0.001(3) 0.056 Uiso 1 1 d . . .
N15 N -0.0452(3) 0.4063(7) -0.0143(3) 0.0546(17) Uani 1 1 d . . .
N16 N -0.0397(2) 0.4732(7) -0.0629(2) 0.0433(15) Uani 1 1 d . . .
N17 N -0.0243(3) 0.7277(7) -0.1030(3) 0.0438(17) Uani 1 1 d . . .
N18 N 0.0308(3) 0.7551(8) -0.0900(3) 0.0522(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.516(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.314(9) . ?
C2 C3 1.394(12) . ?
C3 C4 1.355(11) . ?
C3 H3 0.9300 . ?
C4 N2 1.362(9) . ?
C4 C5 1.502(11) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.503(12) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.338(11) . ?
C7 N3 1.368(10) . ?
C8 C9 1.392(11) . ?
C8 H8 0.9300 . ?
C9 N4 1.348(9) . ?
C9 C10 1.495(11) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.336(10) . ?
C11 N3 1.413(9) . ?
C11 N2 1.425(9) . ?
C12 N5 1.392(9) . ?
C12 C13 1.451(10) . ?
C13 C14 1.363(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.426(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(10) . ?
C15 N5 1.387(9) . ?
C16 N6 1.414(9) . ?
C16 N8 1.408(9) . ?
C17 C18 1.486(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N6 1.353(10) . ?
C18 C19 1.387(10) . ?
C19 C20 1.395(10) . ?
C19 H19 0.9300 . ?
C20 N7 1.305(9) . ?
C20 C21 1.517(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.494(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.361(11) . ?
C23 N8 1.367(9) . ?
C24 C25 1.390(12) . ?
C24 H24 0.9300 . ?
C25 N9 1.310(9) . ?
C25 C26 1.501(12) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.508(13) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 N10 1.303(10) . ?
C28 C29 1.389(14) . ?
C29 C30 1.366(12) . ?
C29 H29 0.9300 . ?
C30 N11 1.370(9) . ?
C30 C31 1.487(12) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.455(12) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 N12 1.368(10) . ?
C33 C34 1.389(11) . ?
C34 C35 1.393(11) . ?
C34 H34 0.9300 . ?
C35 N13 1.325(9) . ?
C35 C36 1.496(11) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.360(10) . ?
C37 N11 1.399(9) . ?
C37 N12 1.405(9) . ?
C38 N14 1.384(9) . ?
C38 C39 1.427(10) . ?
C39 C40 1.336(9) . ?
C39 H39 0.9300 . ?
C40 C41 1.433(9) . ?
C40 H40 0.9300 . ?
C41 N14 1.371(9) . ?
C41 C42 1.360(10) . ?
C42 N16 1.401(9) . ?
C42 N17 1.420(9) . ?
C43 C44 1.476(13) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 N15 1.321(9) . ?
C44 C45 1.412(12) . ?
C45 C46 1.362(11) . ?
C45 H45 0.9300 . ?
C46 N16 1.360(9) . ?
C46 C47 1.504(11) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.501(11) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 N18 1.335(10) . ?
C49 C50 1.393(11) . ?
C50 C51 1.383(10) . ?
C50 H50 0.9300 . ?
C51 N17 1.348(10) . ?
C51 C52 1.482(11) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
N1 N2 1.377(8) . ?
N3 N4 1.372(9) . ?
N5 H2 0.93(7) . ?
N6 N7 1.376(8) . ?
N8 N9 1.387(8) . ?
N10 N11 1.384(8) . ?
N12 N13 1.398(9) . ?
N14 H1 0.84(7) . ?
N15 N16 1.382(8) . ?
N17 N18 1.381(8) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 112.5(8) . . ?
N1 C2 C1 119.0(9) . . ?
C3 C2 C1 128.4(8) . . ?
C4 C3 C2 105.6(7) . . ?
C4 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
N2 C4 C3 106.5(8) . . ?
N2 C4 C5 122.4(8) . . ?
C3 C4 C5 131.1(8) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N3 105.7(8) . . ?
C8 C7 C6 132.1(9) . . ?
N3 C7 C6 122.2(8) . . ?
C7 C8 C9 107.3(8) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N4 C9 C8 111.6(8) . . ?
N4 C9 C10 118.8(8) . . ?
C8 C9 C10 129.6(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N3 122.6(7) . . ?
C12 C11 N2 121.5(7) . . ?
N3 C11 N2 115.9(7) . . ?
C11 C12 N5 125.0(7) . . ?
C11 C12 C13 129.6(7) . . ?
N5 C12 C13 105.4(7) . . ?
C14 C13 C12 108.3(7) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
C13 C14 C15 109.3(7) . . ?
C13 C14 H14 125.4 . . ?
C15 C14 H14 125.4 . . ?
C16 C15 N5 125.3(6) . . ?
C16 C15 C14 128.5(7) . . ?
N5 C15 C14 106.1(7) . . ?
C15 C16 N6 120.3(7) . . ?
C15 C16 N8 122.3(7) . . ?
N6 C16 N8 117.4(7) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 C19 104.5(7) . . ?
N6 C18 C17 123.4(7) . . ?
C19 C18 C17 132.1(8) . . ?
C18 C19 C20 106.3(7) . . ?
C18 C19 H19 126.9 . . ?
C20 C19 H19 126.9 . . ?
N7 C20 C19 112.0(7) . . ?
N7 C20 C21 119.8(8) . . ?
C19 C20 C21 128.2(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N8 105.5(8) . . ?
C24 C23 C22 131.3(8) . . ?
N8 C23 C22 123.2(7) . . ?
C23 C24 C25 106.7(7) . . ?
C23 C24 H24 126.7 . . ?
C25 C24 H24 126.7 . . ?
N9 C25 C24 112.2(7) . . ?
N9 C25 C26 120.8(9) . . ?
C24 C25 C26 127.0(8) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N10 C28 C29 112.0(9) . . ?
N10 C28 C27 120.6(11) . . ?
C29 C28 C27 127.4(10) . . ?
C30 C29 C28 106.9(8) . . ?
C30 C29 H29 126.5 . . ?
C28 C29 H29 126.5 . . ?
C29 C30 N11 105.1(8) . . ?
C29 C30 C31 132.5(9) . . ?
N11 C30 C31 122.5(7) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C33 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N12 C33 C34 104.8(8) . . ?
N12 C33 C32 123.0(8) . . ?
C34 C33 C32 132.1(9) . . ?
C33 C34 C35 106.8(7) . . ?
C33 C34 H34 126.6 . . ?
C35 C34 H34 126.6 . . ?
N13 C35 C34 112.2(7) . . ?
N13 C35 C36 120.7(8) . . ?
C34 C35 C36 127.1(8) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N11 120.7(7) . . ?
C38 C37 N12 122.0(7) . . ?
N11 C37 N12 117.3(7) . . ?
C37 C38 N14 124.1(7) . . ?
C37 C38 C39 129.8(7) . . ?
N14 C38 C39 105.7(7) . . ?
C40 C39 C38 108.5(7) . . ?
C40 C39 H39 125.7 . . ?
C38 C39 H39 125.7 . . ?
C39 C40 C41 109.6(7) . . ?
C39 C40 H40 125.2 . . ?
C41 C40 H40 125.2 . . ?
N14 C41 C42 126.3(6) . . ?
N14 C41 C40 105.2(7) . . ?
C42 C41 C40 128.5(7) . . ?
C41 C42 N16 123.8(7) . . ?
C41 C42 N17 119.5(7) . . ?
N16 C42 N17 116.6(6) . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N15 C44 C45 110.5(8) . . ?
N15 C44 C43 122.1(9) . . ?
C45 C44 C43 127.3(8) . . ?
C46 C45 C44 106.7(8) . . ?
C46 C45 H45 126.6 . . ?
C44 C45 H45 126.6 . . ?
N16 C46 C45 106.1(8) . . ?
N16 C46 C47 123.5(8) . . ?
C45 C46 C47 130.4(8) . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C49 C48 H48A 109.5 . . ?
C49 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C49 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N18 C49 C50 112.2(7) . . ?
N18 C49 C48 117.4(9) . . ?
C50 C49 C48 130.5(9) . . ?
C51 C50 C49 105.7(8) . . ?
C51 C50 H50 127.2 . . ?
C49 C50 H50 127.2 . . ?
N17 C51 C50 106.0(7) . . ?
N17 C51 C52 124.5(8) . . ?
C50 C51 C52 129.5(8) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C2 N1 N2 103.8(7) . . ?
C4 N2 N1 111.5(6) . . ?
C4 N2 C11 129.0(7) . . ?
N1 N2 C11 119.4(6) . . ?
N4 N3 C7 113.0(6) . . ?
N4 N3 C11 119.4(7) . . ?
C7 N3 C11 127.1(7) . . ?
C9 N4 N3 102.5(7) . . ?
C15 N5 C12 111.0(6) . . ?
C15 N5 H2 120(4) . . ?
C12 N5 H2 126(4) . . ?
C18 N6 N7 113.0(6) . . ?
C18 N6 C16 129.0(7) . . ?
N7 N6 C16 117.8(6) . . ?
C20 N7 N6 104.2(6) . . ?
C23 N8 N9 111.6(6) . . ?
C23 N8 C16 129.9(7) . . ?
N9 N8 C16 118.5(6) . . ?
C25 N9 N8 103.9(6) . . ?
C28 N10 N11 104.6(7) . . ?
C30 N11 N10 111.5(6) . . ?
C30 N11 C37 129.0(7) . . ?
N10 N11 C37 119.2(7) . . ?
C33 N12 N13 112.3(7) . . ?
C33 N12 C37 126.6(7) . . ?
N13 N12 C37 120.1(7) . . ?
C35 N13 N12 103.8(6) . . ?
C41 N14 C38 111.0(6) . . ?
C41 N14 H1 119(5) . . ?
C38 N14 H1 126(5) . . ?
C44 N15 N16 105.1(7) . . ?
C46 N16 N15 111.6(6) . . ?
C46 N16 C42 130.5(7) . . ?
N15 N16 C42 117.8(6) . . ?
C51 N17 N18 112.7(6) . . ?
C51 N17 C42 128.6(7) . . ?
N18 N17 C42 118.6(7) . . ?
C49 N18 N17 103.4(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.0(11) . . . . ?
C1 C2 C3 C4 -179.7(9) . . . . ?
C2 C3 C4 N2 0.6(10) . . . . ?
C2 C3 C4 C5 -178.7(10) . . . . ?
N3 C7 C8 C9 0.0(9) . . . . ?
C6 C7 C8 C9 -178.2(9) . . . . ?
C7 C8 C9 N4 0.2(10) . . . . ?
C7 C8 C9 C10 179.1(8) . . . . ?
N3 C11 C12 N5 174.0(7) . . . . ?
N2 C11 C12 N5 -3.2(12) . . . . ?
N3 C11 C12 C13 -2.9(13) . . . . ?
N2 C11 C12 C13 179.9(8) . . . . ?
C11 C12 C13 C14 174.6(8) . . . . ?
N5 C12 C13 C14 -2.8(9) . . . . ?
C12 C13 C14 C15 2.8(9) . . . . ?
C13 C14 C15 C16 -178.3(8) . . . . ?
C13 C14 C15 N5 -1.7(9) . . . . ?
N5 C15 C16 N6 -173.1(7) . . . . ?
C14 C15 C16 N6 3.0(13) . . . . ?
N5 C15 C16 N8 8.9(12) . . . . ?
C14 C15 C16 N8 -175.1(7) . . . . ?
N6 C18 C19 C20 -2.0(8) . . . . ?
C17 C18 C19 C20 179.3(9) . . . . ?
C18 C19 C20 N7 1.5(9) . . . . ?
C18 C19 C20 C21 179.4(8) . . . . ?
N8 C23 C24 C25 -0.4(9) . . . . ?
C22 C23 C24 C25 176.4(8) . . . . ?
C23 C24 C25 N9 1.5(10) . . . . ?
C23 C24 C25 C26 179.9(8) . . . . ?
N10 C28 C29 C30 -0.1(13) . . . . ?
C27 C28 C29 C30 179.0(9) . . . . ?
C28 C29 C30 N11 -0.3(11) . . . . ?
C28 C29 C30 C31 179.1(10) . . . . ?
N12 C33 C34 C35 -0.5(9) . . . . ?
C32 C33 C34 C35 178.8(9) . . . . ?
C33 C34 C35 N13 1.5(9) . . . . ?
C33 C34 C35 C36 -179.2(8) . . . . ?
N11 C37 C38 N14 5.2(12) . . . . ?
N12 C37 C38 N14 -172.5(7) . . . . ?
N11 C37 C38 C39 177.6(8) . . . . ?
N12 C37 C38 C39 -0.1(13) . . . . ?
C37 C38 C39 C40 -174.9(8) . . . . ?
N14 C38 C39 C40 -1.4(9) . . . . ?
C38 C39 C40 C41 1.7(9) . . . . ?
C39 C40 C41 N14 -1.3(9) . . . . ?
C39 C40 C41 C42 176.7(8) . . . . ?
N14 C41 C42 N16 -8.6(13) . . . . ?
C40 C41 C42 N16 173.8(7) . . . . ?
N14 C41 C42 N17 174.2(7) . . . . ?
C40 C41 C42 N17 -3.4(13) . . . . ?
N15 C44 C45 C46 0.2(10) . . . . ?
C43 C44 C45 C46 -178.7(8) . . . . ?
C44 C45 C46 N16 0.3(9) . . . . ?
C44 C45 C46 C47 -177.8(8) . . . . ?
N18 C49 C50 C51 -1.7(10) . . . . ?
C48 C49 C50 C51 179.3(9) . . . . ?
C49 C50 C51 N17 2.3(9) . . . . ?
C49 C50 C51 C52 -176.6(8) . . . . ?
C3 C2 N1 N2 -0.5(10) . . . . ?
C1 C2 N1 N2 179.1(7) . . . . ?
C3 C4 N2 N1 -1.0(9) . . . . ?
C5 C4 N2 N1 178.4(8) . . . . ?
C3 C4 N2 C11 -177.8(8) . . . . ?
C5 C4 N2 C11 1.6(13) . . . . ?
C2 N1 N2 C4 1.0(8) . . . . ?
C2 N1 N2 C11 178.1(7) . . . . ?
C12 C11 N2 C4 130.9(9) . . . . ?
N3 C11 N2 C4 -46.4(11) . . . . ?
C12 C11 N2 N1 -45.6(10) . . . . ?
N3 C11 N2 N1 137.1(7) . . . . ?
C8 C7 N3 N4 -0.1(9) . . . . ?
C6 C7 N3 N4 178.2(8) . . . . ?
C8 C7 N3 C11 172.2(7) . . . . ?
C6 C7 N3 C11 -9.4(13) . . . . ?
C12 C11 N3 N4 -59.6(10) . . . . ?
N2 C11 N3 N4 117.7(7) . . . . ?
C12 C11 N3 C7 128.5(9) . . . . ?
N2 C11 N3 C7 -54.2(10) . . . . ?
C8 C9 N4 N3 -0.3(8) . . . . ?
C10 C9 N4 N3 -179.3(6) . . . . ?
C7 N3 N4 C9 0.3(8) . . . . ?
C11 N3 N4 C9 -172.7(6) . . . . ?
C16 C15 N5 C12 176.6(7) . . . . ?
C14 C15 N5 C12 -0.2(9) . . . . ?
C11 C12 N5 C15 -175.7(7) . . . . ?
C13 C12 N5 C15 1.8(9) . . . . ?
C19 C18 N6 N7 2.0(8) . . . . ?
C17 C18 N6 N7 -179.2(7) . . . . ?
C19 C18 N6 C16 176.4(7) . . . . ?
C17 C18 N6 C16 -4.7(12) . . . . ?
C15 C16 N6 C18 70.8(11) . . . . ?
N8 C16 N6 C18 -111.1(9) . . . . ?
C15 C16 N6 N7 -115.0(8) . . . . ?
N8 C16 N6 N7 63.1(9) . . . . ?
C19 C20 N7 N6 -0.3(9) . . . . ?
C21 C20 N7 N6 -178.4(7) . . . . ?
C18 N6 N7 C20 -1.1(8) . . . . ?
C16 N6 N7 C20 -176.2(6) . . . . ?
C24 C23 N8 N9 -0.7(8) . . . . ?
C22 C23 N8 N9 -177.8(7) . . . . ?
C24 C23 N8 C16 -180.0(7) . . . . ?
C22 C23 N8 C16 2.9(12) . . . . ?
C15 C16 N8 C23 -141.3(8) . . . . ?
N6 C16 N8 C23 40.6(11) . . . . ?
C15 C16 N8 N9 39.5(10) . . . . ?
N6 C16 N8 N9 -138.6(7) . . . . ?
C24 C25 N9 N8 -1.9(9) . . . . ?
C26 C25 N9 N8 179.6(7) . . . . ?
C23 N8 N9 C25 1.6(8) . . . . ?
C16 N8 N9 C25 -179.0(6) . . . . ?
C29 C28 N10 N11 0.4(10) . . . . ?
C27 C28 N10 N11 -178.8(8) . . . . ?
C29 C30 N11 N10 0.5(9) . . . . ?
C31 C30 N11 N10 -179.0(8) . . . . ?
C29 C30 N11 C37 174.6(8) . . . . ?
C31 C30 N11 C37 -4.9(13) . . . . ?
C28 N10 N11 C30 -0.6(9) . . . . ?
C28 N10 N11 C37 -175.3(7) . . . . ?
C38 C37 N11 C30 -125.1(9) . . . . ?
N12 C37 N11 C30 52.8(11) . . . . ?
C38 C37 N11 N10 48.6(10) . . . . ?
N12 C37 N11 N10 -133.6(7) . . . . ?
C34 C33 N12 N13 -0.6(8) . . . . ?
C32 C33 N12 N13 179.9(8) . . . . ?
C34 C33 N12 C37 -169.2(7) . . . . ?
C32 C33 N12 C37 11.4(12) . . . . ?
C38 C37 N12 C33 -125.2(8) . . . . ?
N11 C37 N12 C33 57.1(10) . . . . ?
C38 C37 N12 N13 67.1(10) . . . . ?
N11 C37 N12 N13 -110.7(8) . . . . ?
C34 C35 N13 N12 -1.9(8) . . . . ?
C36 C35 N13 N12 178.9(7) . . . . ?
C33 N12 N13 C35 1.6(8) . . . . ?
C37 N12 N13 C35 170.9(6) . . . . ?
C42 C41 N14 C38 -177.6(8) . . . . ?
C40 C41 N14 C38 0.4(9) . . . . ?
C37 C38 N14 C41 174.5(7) . . . . ?
C39 C38 N14 C41 0.6(9) . . . . ?
C45 C44 N15 N16 -0.6(9) . . . . ?
C43 C44 N15 N16 178.4(8) . . . . ?
C45 C46 N16 N15 -0.6(8) . . . . ?
C47 C46 N16 N15 177.6(7) . . . . ?
C45 C46 N16 C42 179.4(7) . . . . ?
C47 C46 N16 C42 -2.3(12) . . . . ?
C44 N15 N16 C46 0.8(8) . . . . ?
C44 N15 N16 C42 -179.3(7) . . . . ?
C41 C42 N16 C46 145.0(8) . . . . ?
N17 C42 N16 C46 -37.7(11) . . . . ?
C41 C42 N16 N15 -34.9(11) . . . . ?
N17 C42 N16 N15 142.4(7) . . . . ?
C50 C51 N17 N18 -2.3(9) . . . . ?
C52 C51 N17 N18 176.7(7) . . . . ?
C50 C51 N17 C42 -177.5(7) . . . . ?
C52 C51 N17 C42 1.5(13) . . . . ?
C41 C42 N17 C51 -69.4(11) . . . . ?
N16 C42 N17 C51 113.2(8) . . . . ?
C41 C42 N17 N18 115.6(8) . . . . ?
N16 C42 N17 N18 -61.8(9) . . . . ?
C50 C49 N18 N17 0.3(9) . . . . ?
C48 C49 N18 N17 179.5(7) . . . . ?
C51 N17 N18 C49 1.2(8) . . . . ?
C42 N17 N18 C49 177.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H2 N9 0.93(7) 2.30(7) 2.885(9) 121(5) .
N14 H1 N15 0.84(7) 2.32(7) 2.873(8) 123(6) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 998870'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_palladiumcomplex9
# start Validation Reply Form
_vrf_PLAT020_palladiumcomplex9   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.234       
RESPONSE: The crystal did not diffract in higher angles
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H37 Cl4 N10 O1.50 Pd2'
_chemical_formula_weight         892.28

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   13.058(3)
_cell_length_b                   15.125(3)
_cell_length_c                   20.479(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.625(7)
_cell_angle_gamma                90.00
_cell_volume                     3875.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    44801
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1788
_exptl_absorpt_coefficient_mu    1.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_T_max  0.8860
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44801
_diffrn_reflns_av_R_equivalents  0.2343
_diffrn_reflns_av_sigmaI/netI    0.1684
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6824
_reflns_number_gt                3052
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.1425P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6824
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2083
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.2836
_refine_ls_wR_factor_gt          0.2214
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.003
_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
C24 C 0.8532(14) 0.1836(11) 0.1888(9) 0.069(5) Uani 1 1 d . . .
H24 H 0.8895 0.1319 0.2060 0.082 Uiso 1 1 calc R . .
C26 C 0.7170(14) 0.1231(10) 0.0798(9) 0.076(5) Uani 1 1 d . . .
H26A H 0.6611 0.1514 0.0452 0.114 Uiso 1 1 calc R . .
H26B H 0.6869 0.0775 0.1012 0.114 Uiso 1 1 calc R . .
H26C H 0.7678 0.0976 0.0594 0.114 Uiso 1 1 calc R . .
C27 C 0.059(2) 0.0124(18) 0.1257(17) 0.168(13) Uani 1 1 d . . .
H27A H 0.1094 0.0293 0.1681 0.251 Uiso 1 1 calc R . .
H27B H 0.0228 -0.0405 0.1322 0.251 Uiso 1 1 calc R . .
H27C H 0.0084 0.0591 0.1101 0.251 Uiso 1 1 calc R . .
C28 C 0.118(2) -0.0043(17) 0.0734(17) 0.121(9) Uani 1 1 d . . .
N10 N 0.158(3) -0.020(2) 0.0319(15) 0.186(14) Uani 1 1 d . . .
O1 O 0.5913(11) 0.1937(14) 0.2179(7) 0.151(7) Uani 1 1 d . . .
O2 O 0.506(3) 0.505(6) -0.169(4) 0.40(6) Uani 0.50 1 d P . .
C1 C 0.275(2) 0.0963(13) 0.2792(10) 0.119(8) Uani 1 1 d . . .
H1A H 0.2342 0.1483 0.2822 0.178 Uiso 1 1 calc R . .
H1B H 0.3347 0.0918 0.3192 0.178 Uiso 1 1 calc R . .
H1C H 0.2302 0.0450 0.2758 0.178 Uiso 1 1 calc R . .
C2 C 0.3140(15) 0.1022(11) 0.2171(9) 0.076(5) Uani 1 1 d . . .
C3 C 0.3728(15) 0.0386(10) 0.1952(9) 0.080(6) Uani 1 1 d . . .
H3 H 0.3966 -0.0146 0.2170 0.096 Uiso 1 1 calc R . .
C4 C 0.3894(12) 0.0673(10) 0.1368(8) 0.057(4) Uani 1 1 d . . .
C5 C 0.4413(14) 0.0275(10) 0.0874(9) 0.075(5) Uani 1 1 d . . .
H5A H 0.4332 0.0667 0.0494 0.113 Uiso 1 1 calc R . .
H5B H 0.4081 -0.0282 0.0716 0.113 Uiso 1 1 calc R . .
H5C H 0.5160 0.0184 0.1096 0.113 Uiso 1 1 calc R . .
C6 C -0.0550(13) 0.2457(12) 0.0336(10) 0.088(6) Uani 1 1 d . . .
H6A H -0.0424 0.2659 0.0797 0.132 Uiso 1 1 calc R . .
H6B H -0.0966 0.1924 0.0272 0.132 Uiso 1 1 calc R . .
H6C H -0.0932 0.2903 0.0028 0.132 Uiso 1 1 calc R . .
C7 C 0.0482(14) 0.2281(10) 0.0200(10) 0.067(5) Uani 1 1 d . . .
C8 C 0.0605(13) 0.1977(9) -0.0410(9) 0.057(4) Uani 1 1 d . . .
H8 H 0.0052 0.1851 -0.0800 0.069 Uiso 1 1 calc R . .
C9 C 0.1656(13) 0.1892(9) -0.0348(7) 0.049(4) Uani 1 1 d . . .
C10 C 0.2283(13) 0.1551(11) -0.0810(7) 0.067(5) Uani 1 1 d . . .
H10A H 0.3033 0.1584 -0.0579 0.101 Uiso 1 1 calc R . .
H10B H 0.2125 0.1905 -0.1216 0.101 Uiso 1 1 calc R . .
H10C H 0.2088 0.0948 -0.0929 0.101 Uiso 1 1 calc R . .
C11 C 0.3239(12) 0.2068(9) 0.0705(8) 0.049(4) Uani 1 1 d . . .
C12 C 0.4002(11) 0.2573(8) 0.0553(7) 0.043(3) Uani 1 1 d . . .
C13 C 0.3867(12) 0.3222(9) 0.0011(7) 0.048(4) Uani 1 1 d . . .
H13 H 0.3218 0.3381 -0.0296 0.058 Uiso 1 1 calc R . .
C14 C 0.4806(12) 0.3550(9) 0.0022(7) 0.052(4) Uani 1 1 d . . .
H14 H 0.4923 0.3987 -0.0267 0.062 Uiso 1 1 calc R . .
C15 C 0.5629(12) 0.3124(9) 0.0556(7) 0.042(3) Uani 1 1 d . . .
C16 C 0.6657(12) 0.3214(9) 0.0701(6) 0.044(3) Uani 1 1 d . . .
C17 C 0.9001(12) 0.5662(10) 0.0543(8) 0.063(4) Uani 1 1 d . . .
H17A H 0.9079 0.5799 0.1012 0.094 Uiso 1 1 calc R . .
H17B H 0.8743 0.6174 0.0267 0.094 Uiso 1 1 calc R . .
H17C H 0.9680 0.5490 0.0490 0.094 Uiso 1 1 calc R . .
C18 C 0.8213(12) 0.4912(10) 0.0319(8) 0.056(4) Uani 1 1 d . . .
C19 C 0.7890(12) 0.4539(9) -0.0314(7) 0.054(4) Uani 1 1 d . . .
H19 H 0.8087 0.4718 -0.0695 0.064 Uiso 1 1 calc R . .
C20 C 0.7217(13) 0.3844(10) -0.0281(7) 0.057(4) Uani 1 1 d . . .
C21 C 0.6685(13) 0.3176(12) -0.0800(8) 0.074(5) Uani 1 1 d . . .
H21A H 0.6248 0.2796 -0.0615 0.112 Uiso 1 1 calc R . .
H21B H 0.7217 0.2829 -0.0923 0.112 Uiso 1 1 calc R . .
H21C H 0.6246 0.3471 -0.1197 0.112 Uiso 1 1 calc R . .
C22 C 0.9610(14) 0.2958(11) 0.2785(8) 0.080(6) Uani 1 1 d . . .
H22A H 0.9543 0.3579 0.2863 0.120 Uiso 1 1 calc R . .
H22B H 1.0289 0.2845 0.2708 0.120 Uiso 1 1 calc R . .
H22C H 0.9560 0.2632 0.3177 0.120 Uiso 1 1 calc R . .
C23 C 0.8745(12) 0.2680(10) 0.2184(8) 0.056(4) Uani 1 1 d . . .
C25 C 0.7720(13) 0.1901(10) 0.1321(9) 0.056(4) Uani 1 1 d . . .
N1 N 0.2975(10) 0.1715(8) 0.1765(6) 0.059(4) Uani 1 1 d . . .
N2 N 0.3436(9) 0.1500(7) 0.1274(6) 0.046(3) Uani 1 1 d . . .
N3 N 0.1422(10) 0.2372(7) 0.0645(6) 0.050(3) Uani 1 1 d . . .
N4 N 0.2159(10) 0.2138(7) 0.0306(6) 0.052(3) Uani 1 1 d . . .
N5 N 0.5089(9) 0.2529(7) 0.0868(6) 0.047(3) Uani 1 1 d . . .
H5 H 0.5389 0.2189 0.1204 0.057 Uiso 1 1 calc R . .
N6 N 0.8075(9) 0.3239(7) 0.1771(6) 0.052(3) Uani 1 1 d . . .
N7 N 0.7422(9) 0.2750(8) 0.1231(6) 0.048(3) Uani 1 1 d . . .
N8 N 0.7773(9) 0.4503(7) 0.0737(6) 0.052(3) Uani 1 1 d . . .
N9 N 0.7142(9) 0.3825(7) 0.0350(5) 0.045(3) Uani 1 1 d . . .
Cl1 Cl 0.2726(5) 0.3230(4) 0.2727(2) 0.1027(18) Uani 1 1 d . . .
Cl2 Cl 0.0905(4) 0.3984(3) 0.1427(2) 0.0810(14) Uani 1 1 d . . .
Cl3 Cl 0.7767(5) 0.4600(3) 0.2833(2) 0.0894(15) Uani 1 1 d . . .
Cl4 Cl 0.7337(4) 0.6029(3) 0.1623(2) 0.0824(14) Uani 1 1 d . . .
Pd1 Pd 0.20015(10) 0.27791(8) 0.16262(6) 0.0557(4) Uani 1 1 d . . .
Pd2 Pd 0.78064(10) 0.45692(7) 0.17310(6) 0.0540(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C24 C25 1.33(2) . ?
C24 C23 1.41(2) . ?
C24 H24 0.9300 . ?
C26 C25 1.50(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.51(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 N10 1.14(3) . ?
C1 C2 1.50(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.316(19) . ?
C2 C3 1.38(2) . ?
C3 C4 1.35(2) . ?
C3 H3 0.9300 . ?
C4 N2 1.376(17) . ?
C4 C5 1.50(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.48(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N3 1.310(19) . ?
C7 C8 1.38(2) . ?
C8 C9 1.35(2) . ?
C8 H8 0.9300 . ?
C9 N4 1.362(17) . ?
C9 C10 1.508(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.360(18) . ?
C11 N2 1.410(17) . ?
C11 N4 1.418(18) . ?
C12 N5 1.382(17) . ?
C12 C13 1.455(18) . ?
C13 C14 1.317(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.446(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.297(18) . ?
C15 N5 1.404(16) . ?
C16 N9 1.425(16) . ?
C16 N7 1.431(16) . ?
C17 C18 1.51(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N8 1.314(17) . ?
C18 C19 1.37(2) . ?
C19 C20 1.384(19) . ?
C19 H19 0.9300 . ?
C20 N9 1.323(16) . ?
C20 C21 1.49(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.47(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N6 1.331(17) . ?
C25 N7 1.339(18) . ?
N1 N2 1.351(15) . ?
N1 Pd1 2.020(11) . ?
N3 N4 1.384(15) . ?
N3 Pd1 2.031(13) . ?
N5 H5 0.8600 . ?
N6 N7 1.400(15) . ?
N6 Pd2 2.039(11) . ?
N8 N9 1.410(15) . ?
N8 Pd2 2.025(12) . ?
Cl1 Pd1 2.284(5) . ?
Cl2 Pd1 2.281(4) . ?
Cl3 Pd2 2.273(4) . ?
Cl4 Pd2 2.285(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
C25 C24 C23 108.6(15) . . ?
C25 C24 H24 125.7 . . ?
C23 C24 H24 125.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N10 C28 C27 176(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.7(14) . . ?
N1 C2 C1 123.3(15) . . ?
C3 C2 C1 126.0(16) . . ?
C4 C3 C2 108.0(14) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N2 104.1(13) . . ?
C3 C4 C5 133.7(15) . . ?
N2 C4 C5 122.2(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 109.6(15) . . ?
N3 C7 C6 125.0(18) . . ?
C8 C7 C6 125.3(18) . . ?
C9 C8 C7 108.9(14) . . ?
C9 C8 H8 125.5 . . ?
C7 C8 H8 125.5 . . ?
C8 C9 N4 105.0(13) . . ?
C8 C9 C10 133.9(15) . . ?
N4 C9 C10 121.0(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N2 124.0(13) . . ?
C12 C11 N4 119.9(13) . . ?
N2 C11 N4 116.0(11) . . ?
C11 C12 N5 126.0(13) . . ?
C11 C12 C13 128.1(14) . . ?
N5 C12 C13 105.8(12) . . ?
C14 C13 C12 109.3(13) . . ?
C14 C13 H13 125.3 . . ?
C12 C13 H13 125.3 . . ?
C13 C14 C15 109.4(12) . . ?
C13 C14 H14 125.3 . . ?
C15 C14 H14 125.3 . . ?
C16 C15 N5 125.8(13) . . ?
C16 C15 C14 128.5(13) . . ?
N5 C15 C14 105.6(12) . . ?
C15 C16 N9 122.2(13) . . ?
C15 C16 N7 125.1(12) . . ?
N9 C16 N7 112.8(12) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N8 C18 C19 110.5(14) . . ?
N8 C18 C17 122.9(14) . . ?
C19 C18 C17 126.6(13) . . ?
C18 C19 C20 107.2(13) . . ?
C18 C19 H19 126.4 . . ?
C20 C19 H19 126.4 . . ?
N9 C20 C19 106.8(13) . . ?
N9 C20 C21 122.2(14) . . ?
C19 C20 C21 130.9(13) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N6 C23 C24 106.9(14) . . ?
N6 C23 C22 123.8(14) . . ?
C24 C23 C22 129.0(15) . . ?
C24 C25 N7 108.5(14) . . ?
C24 C25 C26 132.2(16) . . ?
N7 C25 C26 119.2(15) . . ?
C2 N1 N2 104.6(11) . . ?
C2 N1 Pd1 134.9(11) . . ?
N2 N1 Pd1 118.9(9) . . ?
N1 N2 C4 112.5(11) . . ?
N1 N2 C11 117.0(11) . . ?
C4 N2 C11 129.7(12) . . ?
C7 N3 N4 105.8(13) . . ?
C7 N3 Pd1 136.9(11) . . ?
N4 N3 Pd1 117.3(10) . . ?
C9 N4 N3 110.7(12) . . ?
C9 N4 C11 131.8(12) . . ?
N3 N4 C11 116.7(12) . . ?
C12 N5 C15 109.8(11) . . ?
C12 N5 H5 125.1 . . ?
C15 N5 H5 125.1 . . ?
C23 N6 N7 107.8(12) . . ?
C23 N6 Pd2 136.6(11) . . ?
N7 N6 Pd2 115.5(9) . . ?
C25 N7 N6 108.1(11) . . ?
C25 N7 C16 133.4(13) . . ?
N6 N7 C16 118.4(11) . . ?
C18 N8 N9 105.7(12) . . ?
C18 N8 Pd2 138.0(11) . . ?
N9 N8 Pd2 116.3(8) . . ?
C20 N9 N8 109.8(11) . . ?
C20 N9 C16 132.4(12) . . ?
N8 N9 C16 117.4(10) . . ?
N1 Pd1 N3 86.5(5) . . ?
N1 Pd1 Cl2 177.8(4) . . ?
N3 Pd1 Cl2 91.6(3) . . ?
N1 Pd1 Cl1 91.9(4) . . ?
N3 Pd1 Cl1 177.5(4) . . ?
Cl2 Pd1 Cl1 89.99(18) . . ?
N8 Pd2 N6 86.9(5) . . ?
N8 Pd2 Cl3 177.0(4) . . ?
N6 Pd2 Cl3 91.9(4) . . ?
N8 Pd2 Cl4 91.3(3) . . ?
N6 Pd2 Cl4 174.4(4) . . ?
Cl3 Pd2 Cl4 89.72(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 O1 0.86 1.95 2.741(17) 151.9 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.685
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.170
_database_code_depnum_ccdc_archive 'CCDC 1011058'
