# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N4 O4, 2 C2 H6 S O'
_chemical_formula_sum            'C34 H38 N4 O6 S2'
_chemical_formula_weight         662.80

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   22.6373(7)
_cell_length_b                   9.5570(3)
_cell_length_c                   16.0764(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.708(2)
_cell_angle_gamma                90.00
_cell_volume                     3348.15(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.2

_exptl_crystal_description       plates
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. Apex II release 2010, Bruker AXS, Inc.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52202
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3843
_reflns_number_gt                3155
_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'








_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
	The complex sits around a crystallographic inversion center at 
1/4, 1/4, 1/2.  The DMSO molecule is disordered.  The disorder involves the 
sulfur atom and the two methyl groups.  The disorder was modeled by 
assigning the variable x to the site occupancy factors for one component 
of the disorder.  The variable (1-x) was assigned to the site occupancy 
factors of the alternate component.  The geometry of the two components 
was restrained to be equivalent throughout the refinement process.  A 
common isotropic displacement parameter was refined for the S atoms and 
a second isotropic displacement parameter was refined for the C atoms 
while refining the variable x.  In this way, the site occupancy for the 
major component refined to 58(2)%. 
;

_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)+(0.0478P)²+3.1524P] 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         3843
_refine_ls_number_parameters     259
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07729(6) 0.74015(12) 0.49914(8) 0.0407(3) Uani 1 1 d . . .
O2 O 0.14153(7) 0.38413(14) 0.80511(8) 0.0524(4) Uani 1 1 d . . .
O3 O 0.18359(5) 0.49817(12) 0.62751(7) 0.0376(3) Uani 1 1 d . . .
S1A S 0.22505(7) 0.61578(14) 0.65817(10) 0.0451(3) Uani 0.42 1 d PD A 1
C16A C 0.2303(3) 0.7090(7) 0.5644(5) 0.0742(19) Uani 0.42 1 d PD A 1
H16A H 0.2534 0.6532 0.5328 0.111 Uiso 0.42 1 calc PR A 1
H16B H 0.2514 0.7982 0.5817 0.111 Uiso 0.42 1 calc PR A 1
H16C H 0.1890 0.7269 0.5271 0.111 Uiso 0.42 1 calc PR A 1
C17A C 0.1812(5) 0.7395(8) 0.6972(5) 0.102(3) Uani 0.42 1 d PD A 1
H17A H 0.1452 0.7662 0.6505 0.153 Uiso 0.42 1 calc PR A 1
H17B H 0.2062 0.8226 0.7178 0.153 Uiso 0.42 1 calc PR A 1
H17C H 0.1677 0.6985 0.7448 0.153 Uiso 0.42 1 calc PR A 1
S1B S 0.20883(5) 0.61472(10) 0.69338(7) 0.0406(2) Uani 0.58 1 d PD A 2
C16B C 0.2283(2) 0.7478(4) 0.6268(4) 0.0713(13) Uani 0.58 1 d PD A 2
H16D H 0.2620 0.7148 0.6044 0.107 Uiso 0.58 1 calc PR A 2
H16E H 0.2410 0.8326 0.6612 0.107 Uiso 0.58 1 calc PR A 2
H16F H 0.1924 0.7686 0.5785 0.107 Uiso 0.58 1 calc PR A 2
C17B C 0.14565(19) 0.7010(4) 0.7153(3) 0.0486(9) Uani 0.58 1 d PD A 2
H17D H 0.1158 0.7256 0.6607 0.073 Uiso 0.58 1 calc PR A 2
H17E H 0.1598 0.7864 0.7485 0.073 Uiso 0.58 1 calc PR A 2
H17F H 0.1263 0.6390 0.7487 0.073 Uiso 0.58 1 calc PR A 2
N1 N 0.08626(5) 0.44455(12) 0.47633(7) 0.0203(2) Uani 1 1 d . . .
N2 N 0.12546(5) 0.24926(12) 0.64096(7) 0.0204(2) Uani 1 1 d . . .
C1 C 0.03886(7) 0.67659(16) 0.44469(10) 0.0303(3) Uani 1 1 d . . .
H1 H 0.0050 0.7282 0.4107 0.036 Uiso 1 1 calc R . .
C2 C 0.04089(6) 0.53006(15) 0.42798(9) 0.0244(3) Uani 1 1 d . . .
C3 C 0.00311(7) 0.44887(18) 0.36485(10) 0.0337(4) Uani 1 1 d . . .
H3 H -0.0322 0.4799 0.3221 0.040 Uiso 1 1 calc R . .
C4 C 0.02622(7) 0.31205(17) 0.37495(9) 0.0304(3) Uani 1 1 d . . .
H4 H 0.0096 0.2336 0.3402 0.037 Uiso 1 1 calc R . .
C5 C 0.07790(6) 0.31240(14) 0.44494(8) 0.0199(3) Uani 1 1 d . . .
C6 C 0.11983(6) 0.19292(13) 0.48613(8) 0.0185(3) Uani 1 1 d . . .
C7 C 0.10880(6) 0.15988(13) 0.57311(8) 0.0183(3) Uani 1 1 d . . .
C8 C 0.07951(6) 0.04630(14) 0.59836(9) 0.0238(3) Uani 1 1 d . . .
H8 H 0.0632 -0.0328 0.5640 0.029 Uiso 1 1 calc R . .
C9 C 0.07855(6) 0.07015(15) 0.68400(9) 0.0270(3) Uani 1 1 d . . .
H9 H 0.0613 0.0100 0.7183 0.032 Uiso 1 1 calc R . .
C10 C 0.10714(6) 0.19681(15) 0.70954(9) 0.0238(3) Uani 1 1 d . . .
C11 C 0.11683(8) 0.27049(18) 0.78952(10) 0.0356(4) Uani 1 1 d . . .
H11 H 0.1029 0.2273 0.8340 0.043 Uiso 1 1 calc R . .
C12 C 0.10418(7) 0.06280(15) 0.42775(9) 0.0268(3) Uani 1 1 d . . .
H12A H 0.1300 -0.0158 0.4552 0.040 Uiso 1 1 calc R . .
H12B H 0.1117 0.0829 0.3717 0.040 Uiso 1 1 calc R . .
H12C H 0.0609 0.0385 0.4191 0.040 Uiso 1 1 calc R . .
C13 C 0.18767(6) 0.22797(13) 0.49544(8) 0.0178(3) Uani 1 1 d . . .
C14 C 0.20497(6) 0.32579(14) 0.44224(8) 0.0209(3) Uani 1 1 d . . .
C15 C 0.23356(6) 0.15309(14) 0.55312(9) 0.0208(3) Uani 1 1 d . . .
H15 H 0.2222(7) 0.0871(17) 0.5917(10) 0.023(4) Uiso 1 1 d . . .
H14 H 0.1757(8) 0.3814(18) 0.4037(11) 0.029(4) Uiso 1 1 d . . .
H2N H 0.1465(8) 0.327(2) 0.6422(11) 0.031(4) Uiso 1 1 d . . .
H1N H 0.1164(8) 0.4757(18) 0.5208(11) 0.030(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(2) . ?
O2 C11 1.216(2) . ?
O3 S1A 1.4618(17) . ?
O3 S1B 1.5365(15) . ?
S1A C17A 1.765(6) . ?
S1A C16A 1.783(6) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
S1B C17B 1.767(4) . ?
S1B C16B 1.792(5) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
N1 C5 1.3542(18) . ?
N1 C2 1.3764(17) . ?
N1 H1N 0.894(18) . ?
N2 C7 1.3561(17) . ?
N2 C10 1.3735(17) . ?
N2 H2N 0.883(19) . ?
C1 C2 1.429(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(2) . ?
C3 C4 1.401(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3864(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.5175(18) . ?
C6 C7 1.5186(17) . ?
C6 C13 1.5391(17) . ?
C6 C12 1.5404(18) . ?
C7 C8 1.3887(18) . ?
C8 C9 1.402(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.430(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.3891(18) . ?
C13 C14 1.3929(18) . ?
C14 C15 1.3880(18) 7_556 ?
C14 H14 0.940(17) . ?
C15 C14 1.3879(18) 7_556 ?
C15 H15 0.966(16) . ?

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
O3 S1A C17A 105.3(4) . . ?
O3 S1A C16A 106.4(3) . . ?
C17A S1A C16A 97.9(4) . . ?
O3 S1B C17B 107.80(15) . . ?
O3 S1B C16B 102.0(2) . . ?
C17B S1B C16B 97.5(2) . . ?
S1B C16B H16D 109.5 . . ?
S1B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
S1B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
S1B C17B H17D 109.5 . . ?
S1B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
S1B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C5 N1 C2 109.61(12) . . ?
C5 N1 H1N 127.4(11) . . ?
C2 N1 H1N 123.0(11) . . ?
C7 N2 C10 109.70(12) . . ?
C7 N2 H2N 125.6(11) . . ?
C10 N2 H2N 124.7(11) . . ?
O1 C1 C2 124.86(14) . . ?
O1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 N1 107.55(13) . . ?
C3 C2 C1 130.24(14) . . ?
N1 C2 C1 122.19(14) . . ?
C2 C3 C4 107.62(13) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
C5 C4 C3 107.36(14) . . ?
C5 C4 H4 126.3 . . ?
C3 C4 H4 126.3 . . ?
N1 C5 C4 107.86(12) . . ?
N1 C5 C6 122.10(11) . . ?
C4 C5 C6 130.02(13) . . ?
C5 C6 C7 108.60(10) . . ?
C5 C6 C13 111.62(10) . . ?
C7 C6 C13 111.36(10) . . ?
C5 C6 C12 109.15(11) . . ?
C7 C6 C12 108.98(11) . . ?
C13 C6 C12 107.08(10) . . ?
N2 C7 C8 107.95(11) . . ?
N2 C7 C6 122.03(11) . . ?
C8 C7 C6 129.95(12) . . ?
C7 C8 C9 107.20(12) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C10 C9 C8 107.68(12) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
N2 C10 C9 107.47(12) . . ?
N2 C10 C11 122.40(14) . . ?
C9 C10 C11 130.10(13) . . ?
O2 C11 C10 125.11(15) . . ?
O2 C11 H11 117.4 . . ?
C10 C11 H11 117.4 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 118.16(12) . . ?
C15 C13 C6 119.93(11) . . ?
C14 C13 C6 121.69(11) . . ?
C15 C14 C13 120.60(12) 7_556 . ?
C15 C14 H14 118.1(10) 7_556 . ?
C13 C14 H14 121.3(10) . . ?
C14 C15 C13 121.24(12) 7_556 . ?
C14 C15 H15 119.8(9) 7_556 . ?
C13 C15 H15 119.0(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1B O3 S1A C17A -39.6(3) . . . . ?
S1B O3 S1A C16A -142.9(3) . . . . ?
S1A O3 S1B C17B 134.2(2) . . . . ?
S1A O3 S1B C16B 32.2(2) . . . . ?
C5 N1 C2 C3 0.17(15) . . . . ?
C5 N1 C2 C1 -178.28(12) . . . . ?
O1 C1 C2 C3 -174.72(15) . . . . ?
O1 C1 C2 N1 3.3(2) . . . . ?
N1 C2 C3 C4 -0.30(16) . . . . ?
C1 C2 C3 C4 177.98(14) . . . . ?
C2 C3 C4 C5 0.32(17) . . . . ?
C2 N1 C5 C4 0.04(15) . . . . ?
C2 N1 C5 C6 -178.48(11) . . . . ?
C3 C4 C5 N1 -0.22(16) . . . . ?
C3 C4 C5 C6 178.14(13) . . . . ?
N1 C5 C6 C7 69.78(15) . . . . ?
C4 C5 C6 C7 -108.37(15) . . . . ?
N1 C5 C6 C13 -53.35(15) . . . . ?
C4 C5 C6 C13 128.49(14) . . . . ?
N1 C5 C6 C12 -171.53(11) . . . . ?
C4 C5 C6 C12 10.32(18) . . . . ?
C10 N2 C7 C8 -0.54(15) . . . . ?
C10 N2 C7 C6 176.73(11) . . . . ?
C5 C6 C7 N2 -69.05(15) . . . . ?
C13 C6 C7 N2 54.24(15) . . . . ?
C12 C6 C7 N2 172.14(12) . . . . ?
C5 C6 C7 C8 107.56(15) . . . . ?
C13 C6 C7 C8 -129.15(14) . . . . ?
C12 C6 C7 C8 -11.24(18) . . . . ?
N2 C7 C8 C9 0.39(15) . . . . ?
C6 C7 C8 C9 -176.59(12) . . . . ?
C7 C8 C9 C10 -0.10(15) . . . . ?
C7 N2 C10 C9 0.48(15) . . . . ?
C7 N2 C10 C11 -178.11(13) . . . . ?
C8 C9 C10 N2 -0.22(15) . . . . ?
C8 C9 C10 C11 178.22(15) . . . . ?
N2 C10 C11 O2 0.1(3) . . . . ?
C9 C10 C11 O2 -178.18(16) . . . . ?
C5 C6 C13 C15 160.94(12) . . . . ?
C7 C6 C13 C15 39.38(16) . . . . ?
C12 C6 C13 C15 -79.66(14) . . . . ?
C5 C6 C13 C14 -24.48(16) . . . . ?
C7 C6 C13 C14 -146.03(12) . . . . ?
C12 C6 C13 C14 94.92(14) . . . . ?
C15 C13 C14 C15 0.2(2) . . . 7_556 ?
C6 C13 C14 C15 -174.44(12) . . . 7_556 ?
C14 C13 C15 C14 -0.2(2) . . . 7_556 ?
C6 C13 C15 C14 174.54(12) . . . 7_556 ?

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
N2 H2N O3 0.883(19) 1.879(19) 2.7552(16) 171.1(17) .
N1 H1N O3 0.894(18) 1.973(18) 2.8504(16) 166.5(16) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1012698'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N4 O4, 2 C3 H7 N O'
_chemical_formula_sum            'C36 H40 N6 O6'
_chemical_formula_weight         652.74

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.1665(12)
_cell_length_b                   17.7506(16)
_cell_length_c                   24.997(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6729.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8436
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       octahedron
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             2768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81471
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7708
_reflns_number_gt                5351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;




_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+4.3345P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7708
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.043
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20998(16) 0.35426(15) 0.11531(9) 0.0283(6) Uani 1 1 d . . . . .
H1 H 0.2036 0.4022 0.1318 0.034 Uiso 1 1 calc R U . . .
C2 C 0.29400(14) 0.33729(12) 0.09180(8) 0.0192(5) Uani 1 1 d . . . . .
C3 C 0.36787(15) 0.38183(13) 0.08764(9) 0.0229(5) Uani 1 1 d . . . . .
H3 H 0.3733 0.4324 0.0997 0.028 Uiso 1 1 calc R U . . .
C4 C 0.43356(15) 0.33927(12) 0.06243(8) 0.0203(5) Uani 1 1 d . . . . .
H4 H 0.4916 0.3557 0.0543 0.024 Uiso 1 1 calc R U . . .
C5 C 0.39862(13) 0.26907(12) 0.05154(8) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.44157(13) 0.19997(11) 0.02674(8) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.39947(13) 0.18370(11) -0.02753(8) 0.0159(4) Uani 1 1 d . . . . .
C8 C 0.43361(14) 0.19200(12) -0.07872(8) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.4910 0.2095 -0.0876 0.023 Uiso 1 1 calc R U . . .
C9 C 0.36778(14) 0.16982(12) -0.11484(8) 0.0193(5) Uani 1 1 d . . . . .
H9 H 0.3726 0.1695 -0.1527 0.023 Uiso 1 1 calc R U . . .
C10 C 0.29475(14) 0.14855(11) -0.08548(8) 0.0169(4) Uani 1 1 d . . . . .
C11 C 0.21164(15) 0.12089(12) -0.10460(9) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.2041 0.1176 -0.1423 0.026 Uiso 1 1 calc R U . . .
C12 C 0.54044(14) 0.21663(13) 0.01838(9) 0.0210(5) Uani 1 1 d . . . . .
H12A H 0.5471 0.2593 -0.0062 0.032 Uiso 1 1 calc R U . . .
H12B H 0.5694 0.1721 0.0032 0.032 Uiso 1 1 calc R U . . .
H12C H 0.5676 0.2291 0.0528 0.032 Uiso 1 1 calc R U . . .
C13 C 0.43520(13) 0.13181(11) 0.06462(8) 0.0152(4) Uani 1 1 d . . . . .
C14 C 0.43223(13) 0.14117(11) 0.11999(8) 0.0157(4) Uani 1 1 d . . . . .
H14 H 0.4305 0.1907 0.1344 0.019 Uiso 1 1 calc R U . . .
C15 C 0.43179(13) 0.07975(11) 0.15480(8) 0.0155(4) Uani 1 1 d . . . . .
C16 C 0.43415(14) 0.00744(12) 0.13322(8) 0.0188(5) Uani 1 1 d . . . . .
H16 H 0.4331 -0.0351 0.1563 0.023 Uiso 1 1 calc R U . . .
C17 C 0.43801(14) -0.00273(12) 0.07830(8) 0.0204(5) Uani 1 1 d . . . . .
H17 H 0.4404 -0.0522 0.0639 0.024 Uiso 1 1 calc R U . . .
C18 C 0.43835(14) 0.05901(12) 0.04422(8) 0.0179(5) Uani 1 1 d . . . . .
H18 H 0.4408 0.0514 0.0066 0.021 Uiso 1 1 calc R U . . .
C19 C 0.42175(13) 0.09154(12) 0.21561(8) 0.0162(4) Uani 1 1 d . . . . .
C20 C 0.45904(14) 0.02518(11) 0.24642(8) 0.0170(4) Uani 1 1 d . . . . .
C21 C 0.42116(15) -0.02002(13) 0.28515(9) 0.0230(5) Uani 1 1 d . . . . .
H21 H 0.3628 -0.0157 0.2986 0.028 Uiso 1 1 calc R U . . .
C22 C 0.48387(15) -0.07330(13) 0.30095(9) 0.0249(5) Uani 1 1 d . . . . .
H22 H 0.4758 -0.1117 0.3270 0.030 Uiso 1 1 calc R U . . .
C23 C 0.55995(15) -0.05997(12) 0.27166(8) 0.0203(5) Uani 1 1 d . . . . .
C24 C 0.64279(16) -0.09875(13) 0.27048(9) 0.0259(5) Uani 1 1 d . . . . .
H24 H 0.6488 -0.1423 0.2923 0.031 Uiso 1 1 calc R U . . .
C25 C 0.46824(13) 0.16238(11) 0.23471(8) 0.0145(4) Uani 1 1 d . . . . .
C26 C 0.44014(14) 0.21715(12) 0.27050(8) 0.0200(5) Uani 1 1 d . . . . .
H26 H 0.3836 0.2202 0.2867 0.024 Uiso 1 1 calc R U . . .
C27 C 0.51031(14) 0.26703(12) 0.27841(9) 0.0209(5) Uani 1 1 d . . . . .
H27 H 0.5100 0.3099 0.3011 0.025 Uiso 1 1 calc R U . . .
C28 C 0.57974(14) 0.24310(11) 0.24751(8) 0.0165(4) Uani 1 1 d . . . . .
C29 C 0.66548(14) 0.27595(12) 0.23959(9) 0.0199(5) Uani 1 1 d . . . . .
H29 H 0.6796 0.3198 0.2596 0.024 Uiso 1 1 calc R U . . .
C30 C 0.32209(13) 0.09832(13) 0.22754(9) 0.0214(5) Uani 1 1 d . . . . .
H30A H 0.3133 0.1064 0.2659 0.032 Uiso 1 1 calc R U . . .
H30B H 0.2922 0.0518 0.2166 0.032 Uiso 1 1 calc R U . . .
H30C H 0.2975 0.1410 0.2076 0.032 Uiso 1 1 calc R U . . .
C31 C 0.66781(14) 0.05054(12) 0.11437(9) 0.0220(5) Uani 1 1 d . . . . .
H31 H 0.6445 0.0034 0.1033 0.026 Uiso 1 1 calc R U . . .
C32 C 0.73741(17) 0.05711(15) 0.02728(9) 0.0310(6) Uani 1 1 d . . . . .
H32A H 0.7090 0.0078 0.0234 0.047 Uiso 1 1 calc R U . . .
H32B H 0.8014 0.0514 0.0235 0.047 Uiso 1 1 calc R U . . .
H32C H 0.7154 0.0913 -0.0004 0.047 Uiso 1 1 calc R U . . .
C33 C 0.75297(17) 0.16148(14) 0.09265(10) 0.0335(6) Uani 1 1 d . . . . .
H33A H 0.7294 0.1782 0.1272 0.050 Uiso 1 1 calc R U . . .
H33B H 0.7362 0.1976 0.0648 0.050 Uiso 1 1 calc R U . . .
H33C H 0.8174 0.1584 0.0948 0.050 Uiso 1 1 calc R U . . .
C34 C 0.13616(15) 0.10545(13) 0.05242(9) 0.0232(5) Uani 1 1 d . . . . .
H34 H 0.1168 0.0944 0.0171 0.028 Uiso 1 1 calc R U . . .
C35 C -0.00946(17) 0.0678(2) 0.08179(12) 0.0538(9) Uani 1 1 d . . . . .
H35A H -0.0514 0.1056 0.0948 0.081 Uiso 1 1 calc R U . . .
H35B H -0.0192 0.0201 0.1007 0.081 Uiso 1 1 calc R U . . .
H35C H -0.0181 0.0602 0.0433 0.081 Uiso 1 1 calc R U . . .
C36 C 0.10471(19) 0.11012(17) 0.14643(10) 0.0434(7) Uani 1 1 d . . . . .
H36A H 0.0953 0.0653 0.1686 0.065 Uiso 1 1 calc R U . . .
H36B H 0.0685 0.1516 0.1600 0.065 Uiso 1 1 calc R U . . .
H36C H 0.1671 0.1245 0.1477 0.065 Uiso 1 1 calc R U . . .
N1 N 0.31344(12) 0.26852(10) 0.06893(7) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.31542(11) 0.15747(10) -0.03221(7) 0.0167(4) Uani 1 1 d . . . . .
N3 N 0.54341(12) 0.00068(10) 0.23881(7) 0.0171(4) Uani 1 1 d . . . . .
N4 N 0.55311(11) 0.17848(10) 0.22128(7) 0.0159(4) Uani 1 1 d . . . . .
N5 N 0.71731(12) 0.08780(10) 0.07965(7) 0.0203(4) Uani 1 1 d . . . . .
N6 N 0.07984(12) 0.09368(11) 0.09153(7) 0.0233(4) Uani 1 1 d . . . . .
O1 O 0.14604(11) 0.31260(11) 0.11603(7) 0.0376(5) Uani 1 1 d . . . . .
O2 O 0.14961(10) 0.10121(10) -0.07654(6) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.70638(11) -0.07987(9) 0.24350(7) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.72144(10) 0.25145(9) 0.20898(6) 0.0278(4) Uani 1 1 d . . . . .
O5 O 0.64952(10) 0.07225(9) 0.15998(6) 0.0262(4) Uani 1 1 d . . . . .
O6 O 0.21208(10) 0.12970(9) 0.05761(6) 0.0271(4) Uani 1 1 d . . . . .
H1N H 0.2779(17) 0.2290(15) 0.0712(10) 0.036(8) Uiso 1 1 d . . . . .
H3N H 0.5824(17) 0.0176(15) 0.2133(10) 0.041(8) Uiso 1 1 d . . . . .
H4N H 0.5886(15) 0.1526(13) 0.1978(9) 0.027(7) Uiso 1 1 d . . . . .
H2N H 0.2811(16) 0.1446(13) -0.0053(10) 0.028(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.220(3) . ?
C1 C2 1.435(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(3) . ?
C2 N1 1.380(3) . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.363(3) . ?
C5 C6 1.521(3) . ?
C6 C7 1.527(3) . ?
C6 C13 1.539(3) . ?
C6 C12 1.543(3) . ?
C7 N2 1.362(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.403(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.377(3) . ?
C10 C11 1.435(3) . ?
C11 O2 1.224(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.390(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 C19 1.542(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.517(3) . ?
C19 C25 1.519(3) . ?
C19 C30 1.545(3) . ?
C20 N3 1.365(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.398(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 N3 1.377(3) . ?
C23 C24 1.433(3) . ?
C24 O3 1.224(3) . ?
C24 H24 0.9500 . ?
C25 N4 1.361(3) . ?
C25 C26 1.388(3) . ?
C26 C27 1.398(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.373(3) . ?
C27 H27 0.9500 . ?
C28 N4 1.382(3) . ?
C28 C29 1.439(3) . ?
C29 O4 1.223(3) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 O5 1.235(3) . ?
C31 N5 1.324(3) . ?
C31 H31 0.9500 . ?
C32 N5 1.450(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 N5 1.452(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 O6 1.236(3) . ?
C34 N6 1.315(3) . ?
C34 H34 0.9500 . ?
C35 N6 1.451(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N6 1.453(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N1 H1N 0.89(3) . ?
N2 H2N 0.88(2) . ?
N3 H3N 0.92(3) . ?
N4 H4N 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.8(2) . . ?
O1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C3 C2 N1 107.65(19) . . ?
C3 C2 C1 129.3(2) . . ?
N1 C2 C1 123.0(2) . . ?
C2 C3 C4 107.7(2) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
C5 C4 C3 107.61(19) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
N1 C5 C4 107.90(19) . . ?
N1 C5 C6 122.01(18) . . ?
C4 C5 C6 130.07(19) . . ?
C5 C6 C7 109.61(16) . . ?
C5 C6 C13 110.87(16) . . ?
C7 C6 C13 111.81(16) . . ?
C5 C6 C12 108.48(17) . . ?
C7 C6 C12 108.80(17) . . ?
C13 C6 C12 107.16(16) . . ?
N2 C7 C8 107.83(18) . . ?
N2 C7 C6 122.16(18) . . ?
C8 C7 C6 130.01(19) . . ?
C7 C8 C9 107.35(19) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
C10 C9 C8 107.79(18) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
N2 C10 C9 107.44(18) . . ?
N2 C10 C11 124.15(19) . . ?
C9 C10 C11 128.40(19) . . ?
O2 C11 C10 125.6(2) . . ?
O2 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.41(19) . . ?
C18 C13 C6 120.19(18) . . ?
C14 C13 C6 121.25(18) . . ?
C13 C14 C15 121.74(19) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 118.59(19) . . ?
C16 C15 C19 120.63(18) . . ?
C14 C15 C19 120.62(18) . . ?
C17 C16 C15 120.32(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.58(19) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C25 108.08(16) . . ?
C20 C19 C15 111.00(17) . . ?
C25 C19 C15 112.12(16) . . ?
C20 C19 C30 109.09(17) . . ?
C25 C19 C30 109.21(17) . . ?
C15 C19 C30 107.30(16) . . ?
N3 C20 C21 107.60(19) . . ?
N3 C20 C19 121.75(18) . . ?
C21 C20 C19 130.65(19) . . ?
C20 C21 C22 107.9(2) . . ?
C20 C21 H21 126.0 . . ?
C22 C21 H21 126.0 . . ?
C23 C22 C21 107.54(19) . . ?
C23 C22 H22 126.2 . . ?
C21 C22 H22 126.2 . . ?
N3 C23 C22 107.26(19) . . ?
N3 C23 C24 121.5(2) . . ?
C22 C23 C24 131.2(2) . . ?
O3 C24 C23 124.8(2) . . ?
O3 C24 H24 117.6 . . ?
C23 C24 H24 117.6 . . ?
N4 C25 C26 107.60(18) . . ?
N4 C25 C19 122.39(18) . . ?
C26 C25 C19 129.78(18) . . ?
C25 C26 C27 107.50(18) . . ?
C25 C26 H26 126.3 . . ?
C27 C26 H26 126.3 . . ?
C28 C27 C26 107.96(19) . . ?
C28 C27 H27 126.0 . . ?
C26 C27 H27 126.0 . . ?
C27 C28 N4 107.43(18) . . ?
C27 C28 C29 130.2(2) . . ?
N4 C28 C29 122.36(19) . . ?
O4 C29 C28 124.7(2) . . ?
O4 C29 H29 117.6 . . ?
C28 C29 H29 117.6 . . ?
C19 C30 H30A 109.5 . . ?
C19 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C19 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 N5 125.2(2) . . ?
O5 C31 H31 117.4 . . ?
N5 C31 H31 117.4 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N5 C33 H33A 109.5 . . ?
N5 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N5 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O6 C34 N6 125.6(2) . . ?
O6 C34 H34 117.2 . . ?
N6 C34 H34 117.2 . . ?
N6 C35 H35A 109.5 . . ?
N6 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N6 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N6 C36 H36A 109.5 . . ?
N6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C5 N1 C2 109.16(18) . . ?
C5 N1 H1N 127.0(17) . . ?
C2 N1 H1N 123.0(16) . . ?
C7 N2 C10 109.60(18) . . ?
C7 N2 H2N 125.2(15) . . ?
C10 N2 H2N 125.0(15) . . ?
C20 N3 C23 109.68(18) . . ?
C20 N3 H3N 126.5(16) . . ?
C23 N3 H3N 123.4(16) . . ?
C25 N4 C28 109.50(17) . . ?
C25 N4 H4N 127.3(15) . . ?
C28 N4 H4N 123.2(15) . . ?
C31 N5 C32 121.54(19) . . ?
C31 N5 C33 120.95(19) . . ?
C32 N5 C33 117.51(19) . . ?
C34 N6 C35 122.2(2) . . ?
C34 N6 C36 120.1(2) . . ?
C35 N6 C36 117.7(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
O1 C1 C2 C3 177.4(2) . . . . ?
O1 C1 C2 N1 -3.2(4) . . . . ?
N1 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 N1 0.7(2) . . . . ?
C3 C4 C5 C6 -177.3(2) . . . . ?
N1 C5 C6 C7 68.5(2) . . . . ?
C4 C5 C6 C7 -113.7(2) . . . . ?
N1 C5 C6 C13 -55.4(2) . . . . ?
C4 C5 C6 C13 122.4(2) . . . . ?
N1 C5 C6 C12 -172.80(18) . . . . ?
C4 C5 C6 C12 4.9(3) . . . . ?
C5 C6 C7 N2 -70.3(2) . . . . ?
C13 C6 C7 N2 53.1(3) . . . . ?
C12 C6 C7 N2 171.22(18) . . . . ?
C5 C6 C7 C8 108.9(2) . . . . ?
C13 C6 C7 C8 -127.7(2) . . . . ?
C12 C6 C7 C8 -9.5(3) . . . . ?
N2 C7 C8 C9 -0.1(2) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 N2 0.0(2) . . . . ?
C8 C9 C10 C11 -179.2(2) . . . . ?
N2 C10 C11 O2 -0.8(4) . . . . ?
C9 C10 C11 O2 178.3(2) . . . . ?
C5 C6 C13 C18 155.49(19) . . . . ?
C7 C6 C13 C18 32.8(3) . . . . ?
C12 C6 C13 C18 -86.3(2) . . . . ?
C5 C6 C13 C14 -28.9(3) . . . . ?
C7 C6 C13 C14 -151.57(19) . . . . ?
C12 C6 C13 C14 89.3(2) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
C6 C13 C14 C15 -176.09(18) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 C15 C19 -175.58(18) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C19 C15 C16 C17 176.23(19) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C6 C13 C18 C17 176.09(19) . . . . ?
C16 C15 C19 C20 27.7(3) . . . . ?
C14 C15 C19 C20 -156.98(18) . . . . ?
C16 C15 C19 C25 148.70(19) . . . . ?
C14 C15 C19 C25 -36.0(3) . . . . ?
C16 C15 C19 C30 -91.4(2) . . . . ?
C14 C15 C19 C30 83.9(2) . . . . ?
C25 C19 C20 N3 -68.9(2) . . . . ?
C15 C19 C20 N3 54.4(2) . . . . ?
C30 C19 C20 N3 172.45(18) . . . . ?
C25 C19 C20 C21 110.4(2) . . . . ?
C15 C19 C20 C21 -126.3(2) . . . . ?
C30 C19 C20 C21 -8.3(3) . . . . ?
N3 C20 C21 C22 -0.4(2) . . . . ?
C19 C20 C21 C22 -179.8(2) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 N3 0.2(2) . . . . ?
C21 C22 C23 C24 -177.7(2) . . . . ?
N3 C23 C24 O3 4.3(4) . . . . ?
C22 C23 C24 O3 -178.0(2) . . . . ?
C20 C19 C25 N4 73.3(2) . . . . ?
C15 C19 C25 N4 -49.3(3) . . . . ?
C30 C19 C25 N4 -168.12(18) . . . . ?
C20 C19 C25 C26 -100.4(2) . . . . ?
C15 C19 C25 C26 136.9(2) . . . . ?
C30 C19 C25 C26 18.1(3) . . . . ?
N4 C25 C26 C27 0.1(2) . . . . ?
C19 C25 C26 C27 174.5(2) . . . . ?
C25 C26 C27 C28 0.4(2) . . . . ?
C26 C27 C28 N4 -0.7(2) . . . . ?
C26 C27 C28 C29 177.3(2) . . . . ?
C27 C28 C29 O4 -176.5(2) . . . . ?
N4 C28 C29 O4 1.3(3) . . . . ?
C4 C5 N1 C2 -1.2(2) . . . . ?
C6 C5 N1 C2 177.03(18) . . . . ?
C3 C2 N1 C5 1.2(2) . . . . ?
C1 C2 N1 C5 -178.35(19) . . . . ?
C8 C7 N2 C10 0.1(2) . . . . ?
C6 C7 N2 C10 179.50(18) . . . . ?
C9 C10 N2 C7 0.0(2) . . . . ?
C11 C10 N2 C7 179.17(19) . . . . ?
C21 C20 N3 C23 0.6(2) . . . . ?
C19 C20 N3 C23 -179.98(18) . . . . ?
C22 C23 N3 C20 -0.5(2) . . . . ?
C24 C23 N3 C20 177.68(19) . . . . ?
C26 C25 N4 C28 -0.5(2) . . . . ?
C19 C25 N4 C28 -175.49(17) . . . . ?
C27 C28 N4 C25 0.8(2) . . . . ?
C29 C28 N4 C25 -177.44(19) . . . . ?
O5 C31 N5 C32 178.3(2) . . . . ?
O5 C31 N5 C33 -2.1(3) . . . . ?
O6 C34 N6 C35 177.5(3) . . . . ?
O6 C34 N6 C36 0.6(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
C4 H4 O2 0.95 2.58 3.461(3) 155 3
C8 H8 O1 0.95 2.49 3.355(3) 152 3
C26 H26 O4 0.95 2.52 3.411(3) 156 6_556
C29 H29 O3 0.95 2.51 3.215(3) 131 7_765
C33 H33A O4 0.98 2.43 3.352(3) 157 .
C34 H34 O2 0.95 2.40 3.231(3) 146 .
N1 H1N O6 0.89(3) 2.05(3) 2.918(2) 165(2) .
N3 H3N O5 0.92(3) 1.94(3) 2.844(2) 168(2) .
N4 H4N O5 0.92(2) 1.94(2) 2.836(2) 163(2) .
N2 H2N O6 0.88(2) 1.91(2) 2.782(2) 172(2) .

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1012699'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N4 O4, 2 C3 H7 N O'
_chemical_formula_sum            'C36 H40 N6 O6'
_chemical_formula_weight         652.74

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3870(4)
_cell_length_b                   14.2432(5)
_cell_length_c                   14.6816(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.354(2)
_cell_angle_gamma                90
_cell_volume                     1699.08(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6603
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.2

_exptl_crystal_description       prisms
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29051
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3904
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
The N,N'-dimethyl formamide solvate molecule was disordered.  The disorder 
was modeled by assigning the variable x to the site occupancy factors for 
one component of the disorder, while (1-x) was assigned to the site 
occupancy factors for the alternate component.  The geometry of the two 
components were restrained to be equivalent throughout the refinement 
process.  A common isotropic displacement parameter was refined while 
refining x.  In this way, the major component of the disordered solvate 
molecule had a site occupancy of 80(2)%.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.8566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3904
_refine_ls_number_parameters     247
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.022
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38130(19) 0.82756(11) 0.32909(12) 0.0269(3) Uani 1 1 d . . . . .
C2 C 0.4270(2) 0.88840(11) 0.40398(13) 0.0341(4) Uani 1 1 d . . . . .
H2 H 0.3878 0.9507 0.4066 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5414(2) 0.84215(11) 0.47542(12) 0.0328(4) Uani 1 1 d . . . . .
H3 H 0.5937 0.8672 0.5354 0.039 Uiso 1 1 calc R U . . .
C4 C 0.56424(19) 0.75335(10) 0.44284(11) 0.0234(3) Uani 1 1 d . . . . .
C5 C 0.68011(19) 0.67540(10) 0.48939(11) 0.0240(3) Uani 1 1 d . . . . .
C6 C 0.81493(18) 0.66642(10) 0.43756(11) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.9778(2) 0.69568(13) 0.46496(13) 0.0356(4) Uani 1 1 d . . . . .
H7 H 1.0317 0.7215 0.5242 0.043 Uiso 1 1 calc R U . . .
C8 C 1.0475(2) 0.68016(14) 0.38970(14) 0.0392(4) Uani 1 1 d . . . . .
H8 H 1.1573 0.6948 0.3880 0.047 Uiso 1 1 calc R U . . .
C9 C 0.93015(19) 0.63997(11) 0.31812(12) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.2664(2) 0.83991(13) 0.24005(14) 0.0391(4) Uani 1 1 d . . . . .
H10 H 0.2144 0.8994 0.2271 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9478(2) 0.60750(12) 0.22953(14) 0.0351(4) Uani 1 1 d . . . . .
H11 H 1.0499 0.6199 0.2149 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7590(2) 0.70265(13) 0.59204(12) 0.0360(4) Uani 1 1 d . . . . .
H12A H 0.8343 0.6529 0.6222 0.054 Uiso 1 1 calc R U . . .
H12B H 0.6726 0.7110 0.6257 0.054 Uiso 1 1 calc R U . . .
H12C H 0.8201 0.7615 0.5935 0.054 Uiso 1 1 calc R U . . .
C13 C 0.58516(18) 0.58327(10) 0.49111(10) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.65339(19) 0.49618(11) 0.48091(11) 0.0252(3) Uani 1 1 d . . . . .
C15 C 0.43163(19) 0.58577(11) 0.51071(11) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.46679(15) 0.74527(9) 0.35460(9) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.4593 0.6950 0.3190 0.028 Uiso 1 1 calc R U . . .
N2 N 0.78820(15) 0.63237(9) 0.34887(9) 0.0242(3) Uani 1 1 d . . . . .
H2A H 0.6945 0.6090 0.3159 0.029 Uiso 1 1 calc R U . . .
O1 O 0.23061(19) 0.77962(11) 0.17980(11) 0.0599(4) Uani 1 1 d . . . . .
O2 O 0.84488(17) 0.56539(9) 0.17059(10) 0.0431(3) Uani 1 1 d . . . . .
O3 O 0.4668(6) 0.5787(3) 0.2457(2) 0.0349(8) Uani 0.8 1 d D U P A 1
N3 N 0.2521(3) 0.49097(14) 0.16421(12) 0.0257(5) Uani 0.8 1 d D U P A 1
C16 C 0.2121(3) 0.55608(17) 0.08517(17) 0.0390(5) Uani 0.8 1 d D U P A 1
H16A H 0.2801 0.6126 0.1005 0.059 Uiso 0.8 1 calc R U P A 1
H16B H 0.0956 0.5734 0.0724 0.059 Uiso 0.8 1 calc R U P A 1
H16C H 0.2339 0.5260 0.0294 0.059 Uiso 0.8 1 calc R U P A 1
C17 C 0.1557(3) 0.40550(16) 0.15570(17) 0.0378(5) Uani 0.8 1 d D U P A 1
H17A H 0.1991 0.3654 0.2105 0.057 Uiso 0.8 1 calc R U P A 1
H17B H 0.1621 0.3721 0.0984 0.057 Uiso 0.8 1 calc R U P A 1
H17C H 0.0407 0.4212 0.1525 0.057 Uiso 0.8 1 calc R U P A 1
C18 C 0.3770(2) 0.50770(14) 0.23690(15) 0.0296(4) Uani 0.8 1 d D U P A 1
H18 H 0.4003 0.4625 0.2860 0.036 Uiso 0.8 1 calc R U P A 1
O3A O 0.473(3) 0.5689(17) 0.2616(11) 0.032 Uiso 0.2 1 d D U P B 2
N3A N 0.2665(13) 0.5105(7) 0.1448(6) 0.032 Uiso 0.2 1 d D U P B 2
C16A C 0.2465(11) 0.4287(6) 0.2010(6) 0.032 Uiso 0.2 1 d D U P B 2
H16D H 0.2584 0.3713 0.1666 0.048 Uiso 0.2 1 calc R U P B 2
H16E H 0.1369 0.4301 0.2135 0.048 Uiso 0.2 1 calc R U P B 2
H16F H 0.3306 0.4299 0.2607 0.048 Uiso 0.2 1 calc R U P B 2
C17A C 0.1626(11) 0.5182(7) 0.0511(6) 0.032 Uiso 0.2 1 d D U P B 2
H17D H 0.0476 0.5246 0.0542 0.048 Uiso 0.2 1 calc R U P B 2
H17E H 0.1745 0.4618 0.0152 0.048 Uiso 0.2 1 calc R U P B 2
H17F H 0.1948 0.5735 0.0202 0.048 Uiso 0.2 1 calc R U P B 2
C18A C 0.3819(10) 0.5734(5) 0.1800(6) 0.032 Uiso 0.2 1 d D U P B 2
H18A H 0.3962 0.6245 0.1413 0.038 Uiso 0.2 1 calc R U P B 2
H15 H 0.384(2) 0.6457(12) 0.5201(12) 0.025(4) Uiso 1 1 d . . . . .
H14 H 0.762(2) 0.4915(12) 0.4685(12) 0.029(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3766(19) . ?
C1 C2 1.378(2) . ?
C1 C10 1.430(2) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.354(2) . ?
C4 C5 1.522(2) . ?
C5 C6 1.517(2) . ?
C5 C12 1.538(2) . ?
C5 C13 1.538(2) . ?
C6 N2 1.355(2) . ?
C6 C7 1.389(2) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.378(2) . ?
C9 C11 1.422(3) . ?
C10 O1 1.216(2) . ?
C10 H10 0.9500 . ?
C11 O2 1.218(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.388(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.389(2) 3_666 ?
C14 H14 0.971(18) . ?
C15 C14 1.389(2) 3_666 ?
C15 H15 0.968(17) . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
O3 C18 1.248(5) . ?
N3 C18 1.319(3) . ?
N3 C17 1.450(3) . ?
N3 C16 1.458(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
O3A C18A 1.254(9) . ?
N3A C18A 1.326(8) . ?
N3A C17A 1.438(8) . ?
N3A C16A 1.461(8) . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18A 0.9500 . ?

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
N1 C1 C2 107.18(14) . . ?
N1 C1 C10 122.76(15) . . ?
C2 C1 C10 130.05(16) . . ?
C1 C2 C3 107.80(14) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
C4 C3 C2 107.45(15) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
N1 C4 C3 107.82(14) . . ?
N1 C4 C5 122.30(13) . . ?
C3 C4 C5 129.81(15) . . ?
C6 C5 C4 107.98(12) . . ?
C6 C5 C12 108.66(13) . . ?
C4 C5 C12 109.12(13) . . ?
C6 C5 C13 112.93(13) . . ?
C4 C5 C13 110.75(12) . . ?
C12 C5 C13 107.32(12) . . ?
N2 C6 C7 107.59(15) . . ?
N2 C6 C5 123.09(13) . . ?
C7 C6 C5 129.15(15) . . ?
C6 C7 C8 107.42(16) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C9 C8 C7 108.15(15) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
C8 C9 N2 107.18(16) . . ?
C8 C9 C11 128.15(16) . . ?
N2 C9 C11 124.62(16) . . ?
O1 C10 C1 124.55(17) . . ?
O1 C10 H10 117.7 . . ?
C1 C10 H10 117.7 . . ?
O2 C11 C9 126.43(17) . . ?
O2 C11 H11 116.8 . . ?
C9 C11 H11 116.8 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 118.25(14) . . ?
C15 C13 C5 119.48(13) . . ?
C14 C13 C5 122.07(13) . . ?
C15 C14 C13 120.42(14) 3_666 . ?
C15 C14 H14 118.9(10) 3_666 . ?
C13 C14 H14 120.7(10) . . ?
C13 C15 C14 121.32(14) . 3_666 ?
C13 C15 H15 119.5(10) . . ?
C14 C15 H15 119.2(10) 3_666 . ?
C4 N1 C1 109.75(13) . . ?
C4 N1 H1 125.1 . . ?
C1 N1 H1 125.1 . . ?
C6 N2 C9 109.64(13) . . ?
C6 N2 H2A 125.2 . . ?
C9 N2 H2A 125.2 . . ?
C18 N3 C17 122.39(19) . . ?
C18 N3 C16 120.59(19) . . ?
C17 N3 C16 116.89(19) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 N3 124.6(2) . . ?
O3 C18 H18 117.7 . . ?
N3 C18 H18 117.7 . . ?
C18A N3A C17A 122.2(8) . . ?
C18A N3A C16A 119.5(8) . . ?
C17A N3A C16A 118.3(7) . . ?
N3A C16A H16D 109.5 . . ?
N3A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
N3A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
N3A C17A H17D 109.5 . . ?
N3A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
N3A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
O3A C18A N3A 123.6(12) . . ?
O3A C18A H18A 118.2 . . ?
N3A C18A H18A 118.2 . . ?

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
N1 C1 C2 C3 0.00(18) . . . . ?
C10 C1 C2 C3 178.82(17) . . . . ?
C1 C2 C3 C4 0.14(19) . . . . ?
C2 C3 C4 N1 -0.23(18) . . . . ?
C2 C3 C4 C5 176.92(15) . . . . ?
N1 C4 C5 C6 67.79(17) . . . . ?
C3 C4 C5 C6 -108.99(18) . . . . ?
N1 C4 C5 C12 -174.26(14) . . . . ?
C3 C4 C5 C12 8.9(2) . . . . ?
N1 C4 C5 C13 -56.33(19) . . . . ?
C3 C4 C5 C13 126.88(17) . . . . ?
C4 C5 C6 N2 -69.89(17) . . . . ?
C12 C5 C6 N2 171.87(14) . . . . ?
C13 C5 C6 N2 52.91(19) . . . . ?
C4 C5 C6 C7 104.85(18) . . . . ?
C12 C5 C6 C7 -13.4(2) . . . . ?
C13 C5 C6 C7 -132.35(17) . . . . ?
N2 C6 C7 C8 1.23(19) . . . . ?
C5 C6 C7 C8 -174.15(15) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C7 C8 C9 N2 0.99(19) . . . . ?
C7 C8 C9 C11 -176.50(16) . . . . ?
N1 C1 C10 O1 1.6(3) . . . . ?
C2 C1 C10 O1 -177.08(19) . . . . ?
C8 C9 C11 O2 173.69(18) . . . . ?
N2 C9 C11 O2 -3.4(3) . . . . ?
C6 C5 C13 C15 -161.41(13) . . . . ?
C4 C5 C13 C15 -40.16(19) . . . . ?
C12 C5 C13 C15 78.86(17) . . . . ?
C6 C5 C13 C14 23.8(2) . . . . ?
C4 C5 C13 C14 145.00(15) . . . . ?
C12 C5 C13 C14 -95.98(17) . . . . ?
C15 C13 C14 C15 0.6(3) . . . 3_666 ?
C5 C13 C14 C15 175.54(14) . . . 3_666 ?
C14 C13 C15 C14 -0.7(3) . . . 3_666 ?
C5 C13 C15 C14 -175.69(14) . . . 3_666 ?
C3 C4 N1 C1 0.24(17) . . . . ?
C5 C4 N1 C1 -177.17(13) . . . . ?
C2 C1 N1 C4 -0.15(17) . . . . ?
C10 C1 N1 C4 -179.07(15) . . . . ?
C7 C6 N2 C9 -0.62(17) . . . . ?
C5 C6 N2 C9 175.10(13) . . . . ?
C8 C9 N2 C6 -0.23(18) . . . . ?
C11 C9 N2 C6 177.37(15) . . . . ?
C17 N3 C18 O3 177.4(4) . . . . ?
C16 N3 C18 O3 1.6(5) . . . . ?
C17A N3A C18A O3A 179.3(19) . . . . ?
C16A N3A C18A O3A -3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.95 2.58 3.393(2) 144 2_655
C7 H7 O1 0.95 2.47 3.354(2) 155 4_676
N1 H1 O3 0.88 1.98 2.861(6) 174 .
N1 H1 O3A 0.88 2.00 2.87(3) 168 .
N2 H2A O3 0.88 1.98 2.850(4) 170 .
N2 H2A O3A 0.88 1.92 2.785(17) 169 .
C2 H2 O2 0.95 2.58 3.393(2) 144 2_655
C7 H7 O1 0.95 2.47 3.354(2) 155 4_676
N1 H1 O3 0.88 1.98 2.861(6) 174 .
N1 H1 O3A 0.88 2.00 2.87(3) 168 .
N2 H2A O3 0.88 1.98 2.850(4) 170 .
N2 H2A O3A 0.88 1.92 2.785(17) 169 .

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1012700'
