# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_cook126
_database_code_depnum_ccdc_archive 'CCDC 1040831'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'Fdd2 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   22.4744(9)
_cell_length_b                   49.168(2)
_cell_length_c                   12.4218(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     13726.4(10)
_cell_formula_units_Z            48
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5532
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      67.89

_exptl_crystal_description       'thin rod'
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_max          0.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5760
_exptl_absorpt_coefficient_mu    0.699
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.7745
_exptl_absorpt_correction_T_max  0.9773

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
# PLATINUM 135 parameters
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19212
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         68.23
_reflns_number_total             5970
_reflns_number_gt                1910
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1318P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_number_reflns         5970
_refine_ls_number_parameters     460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1599
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_refine_ls_shift/su_max          1.715
_refine_ls_shift/su_mean         0.412

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
N1' N 0.11915(13) 0.95705(6) 0.8029(2) 0.0440(8) Uani 1 1 d . . .
C2' C 0.13445(15) 0.93280(7) 0.7591(3) 0.0382(9) Uani 1 1 d . . .
C3' C 0.10359(15) 0.90721(8) 0.7616(3) 0.0402(8) Uani 1 1 d . . .
C4' C 0.05115(16) 0.89769(8) 0.8070(4) 0.0475(9) Uani 1 1 d . . .
H4'A H 0.0274 0.9097 0.8456 0.057 Uiso 1 1 calc R . .
N5' N 0.03353(17) 0.87185(9) 0.7971(3) 0.0534(10) Uani 1 1 d . . .
C6' C 0.06929(17) 0.85467(10) 0.7427(4) 0.0555(11) Uani 1 1 d . . .
H6'A H 0.0572 0.8366 0.7380 0.067 Uiso 1 1 calc R . .
C7' C 0.12182(18) 0.86146(9) 0.6939(4) 0.0525(12) Uani 1 1 d . . .
H7'A H 0.1443 0.8488 0.6558 0.063 Uiso 1 1 calc R . .
C8' C 0.13971(17) 0.88866(8) 0.7048(4) 0.0447(9) Uani 1 1 d . . .
N9' N 0.18910(14) 0.90154(12) 0.6674(4) 0.0477(8) Uani 1 1 d . . .
H9'A H 0.2169 0.8943 0.6293 0.057 Uiso 1 1 calc R . .
C10' C 0.18687(19) 0.92828(11) 0.7011(3) 0.0438(8) Uani 1 1 d . . .
C11' C 0.22741(19) 0.94964(9) 0.6869(4) 0.0520(10) Uani 1 1 d . . .
H11B H 0.2625 0.9474 0.6483 0.062 Uiso 1 1 calc R . .
C12' C 0.2126(2) 0.97391(10) 0.7328(4) 0.0520(17) Uani 1 1 d . . .
H12B H 0.2383 0.9887 0.7275 0.062 Uiso 1 1 calc R . .
C13' C 0.15831(19) 0.97641(7) 0.7884(3) 0.0469(16) Uani 1 1 d . . .
O14' O 0.14816(12) 1.00175(7) 0.8297(2) 0.0571(12) Uani 1 1 d . . .
C15' C 0.09290(16) 1.00598(10) 0.8849(3) 0.0497(10) Uani 1 1 d . . .
H15E H 0.0898 0.9937 0.9457 0.060 Uiso 1 1 calc R . .
H15F H 0.0598 1.0025 0.8367 0.060 Uiso 1 1 calc R . .
C16' C 0.0915(4) 1.03514(9) 0.9233(3) 0.0607(12) Uani 1 1 d . . .
H16E H 0.1222 1.0377 0.9773 0.073 Uiso 1 1 calc R . .
H16F H 0.1004 1.0471 0.8632 0.073 Uiso 1 1 calc R . .
C17' C 0.03228(19) 1.04298(9) 0.9704(4) 0.0693(15) Uani 1 1 d . . .
H17D H 0.0336 1.0616 0.9934 0.104 Uiso 1 1 calc R . .
H17E H 0.0236 1.0315 1.0310 0.104 Uiso 1 1 calc R . .
H17F H 0.0018 1.0408 0.9169 0.104 Uiso 1 1 calc R . .
N1" N 0.11927(15) 0.95700(6) 1.1363(3) 0.0432(10) Uani 1 1 d . . .
N1 N 0.11915(13) 0.95704(6) 0.4701(3) 0.0443(7) Uani 1 1 d . . .
C2 C 0.1343(2) 0.93285(7) 0.4262(3) 0.0407(15) Uani 1 1 d . . .
C3 C 0.10372(16) 0.90727(7) 0.4288(4) 0.0416(11) Uani 1 1 d . . .
C4 C 0.05121(16) 0.89762(8) 0.4738(3) 0.0463(10) Uani 1 1 d . . .
H4A H 0.0274 0.9096 0.5124 0.056 Uiso 1 1 calc R . .
N5 N 0.03354(13) 0.87181(7) 0.4640(3) 0.0535(9) Uani 1 1 d . . .
C6 C 0.06908(18) 0.85459(9) 0.4088(5) 0.0553(10) Uani 1 1 d . . .
H6A H 0.0567 0.8366 0.4032 0.066 Uiso 1 1 calc R . .
C7 C 0.12180(18) 0.86142(8) 0.3603(4) 0.0530(13) Uani 1 1 d . . .
H7A H 0.1444 0.8488 0.3224 0.064 Uiso 1 1 calc R . .
C8 C 0.13948(18) 0.88858(8) 0.3713(3) 0.0436(12) Uani 1 1 d . . .
N9 N 0.18921(14) 0.90149(12) 0.3349(6) 0.0482(8) Uani 1 1 d . . .
H9A H 0.2172 0.8942 0.2976 0.058 Uiso 1 1 calc R . .
C10 C 0.18702(15) 0.92825(8) 0.3681(4) 0.0431(9) Uani 1 1 d . . .
C11 C 0.2277(2) 0.94941(13) 0.3534(3) 0.0487(16) Uani 1 1 d . . .
H11A H 0.2628 0.9471 0.3147 0.058 Uiso 1 1 calc R . .
C12 C 0.21274(17) 0.97385(8) 0.3994(3) 0.0519(11) Uani 1 1 d . . .
H12A H 0.2384 0.9886 0.3938 0.062 Uiso 1 1 calc R . .
C13 C 0.15864(17) 0.97654(8) 0.4550(3) 0.0452(13) Uani 1 1 d . . .
O14 O 0.14804(13) 1.00185(9) 0.4960(2) 0.0559(10) Uani 1 1 d . . .
C15 C 0.09297(17) 1.00594(7) 0.5516(3) 0.0496(10) Uani 1 1 d . . .
H15C H 0.0902 0.9937 0.6126 0.060 Uiso 1 1 calc R . .
H15D H 0.0597 1.0024 0.5038 0.060 Uiso 1 1 calc R . .
C16 C 0.0916(2) 1.03517(8) 0.5895(4) 0.0583(14) Uani 1 1 d . . .
H16C H 0.1002 1.0470 0.5291 0.070 Uiso 1 1 calc R . .
H16D H 0.1225 1.0378 0.6430 0.070 Uiso 1 1 calc R . .
C17 C 0.03224(19) 1.04293(9) 0.6373(3) 0.0689(17) Uani 1 1 d . . .
H17A H 0.0334 1.0616 0.6602 0.103 Uiso 1 1 calc R . .
H17B H 0.0239 1.0315 0.6981 0.103 Uiso 1 1 calc R . .
H17C H 0.0016 1.0407 0.5842 0.103 Uiso 1 1 calc R . .
O14" O 0.14803(13) 1.00182(6) 1.1630(2) 0.0548(7) Uani 1 1 d . . .
C2" C 0.1344(2) 0.93281(8) 1.0929(3) 0.0399(10) Uani 1 1 d . . .
N9" N 0.18920(13) 0.90139(6) 1.0013(3) 0.0479(9) Uani 1 1 d . . .
H9"A H 0.2171 0.8941 0.9638 0.057 Uiso 1 1 calc R . .
C17" C 0.0323(2) 1.04290(8) 1.3038(4) 0.0680(13) Uani 1 1 d . . .
H17G H 0.0332 1.0615 1.3268 0.102 Uiso 1 1 calc R . .
H17H H 0.0239 1.0314 1.3644 0.102 Uiso 1 1 calc R . .
H17I H 0.0019 1.0406 1.2503 0.102 Uiso 1 1 calc R . .
C16" C 0.0920(3) 1.03526(8) 1.2565(4) 0.0609(18) Uani 1 1 d . . .
H16A H 0.1227 1.0378 1.3104 0.073 Uiso 1 1 calc R . .
H16B H 0.1008 1.0472 1.1963 0.073 Uiso 1 1 calc R . .
C15" C 0.09292(17) 1.00608(9) 1.2184(3) 0.0500(9) Uani 1 1 d . . .
H15A H 0.0898 0.9938 1.2793 0.060 Uiso 1 1 calc R . .
H15B H 0.0597 1.0027 1.1705 0.060 Uiso 1 1 calc R . .
C13" C 0.1585(2) 0.97646(8) 1.1217(3) 0.0451(10) Uani 1 1 d . . .
C3" C 0.10353(16) 0.90723(7) 1.0951(5) 0.0405(11) Uani 1 1 d . . .
C4" C 0.05090(17) 0.89766(7) 1.1401(3) 0.0466(9) Uani 1 1 d . . .
H4"A H 0.0269 0.9097 1.1783 0.056 Uiso 1 1 calc R . .
N5" N 0.03363(16) 0.87181(8) 1.1304(3) 0.0528(11) Uani 1 1 d . . .
C6" C 0.06909(19) 0.85457(8) 1.0753(3) 0.0543(11) Uani 1 1 d . . .
H6"A H 0.0567 0.8366 1.0693 0.065 Uiso 1 1 calc R . .
C10" C 0.18704(18) 0.92810(10) 1.0347(4) 0.0446(9) Uani 1 1 d . . .
C8" C 0.13951(16) 0.88858(8) 1.0377(3) 0.0441(12) Uani 1 1 d . . .
C7" C 0.1218(2) 0.86150(9) 1.0276(3) 0.0518(10) Uani 1 1 d . . .
H7"A H 0.1447 0.8488 0.9904 0.062 Uiso 1 1 calc R . .
C11" C 0.2273(3) 0.94939(9) 1.0209(4) 0.0495(13) Uani 1 1 d . . .
H11C H 0.2625 0.9470 0.9828 0.059 Uiso 1 1 calc R . .
C12" C 0.2128(2) 0.97402(9) 1.0658(3) 0.0501(13) Uani 1 1 d . . .
H12C H 0.2383 0.9888 1.0595 0.060 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1' C13' 1.309(5) . ?
N1' C2' 1.355(4) . ?
C2' C10' 1.399(6) . ?
C2' C3' 1.437(4) . ?
C3' C4' 1.388(4) . ?
C3' C8' 1.410(5) . ?
C4' N5' 1.337(4) . ?
C4' H4'A 0.9300 . ?
N5' C6' 1.347(5) . ?
C6' C7' 1.369(6) . ?
C6' H6'A 0.9300 . ?
C7' C8' 1.403(6) . ?
C7' H7'A 0.9300 . ?
C8' N9' 1.360(5) . ?
N9' C10' 1.381(4) . ?
N9' H9'A 0.8600 . ?
C10' C11' 1.401(5) . ?
C11' C12' 1.364(6) . ?
C11' H11B 0.9300 . ?
C12' C13' 1.408(5) . ?
C12' H12B 0.9300 . ?
C13' O14' 1.366(5) . ?
O14' C15' 1.434(4) . ?
C15' C16' 1.511(5) . ?
C15' H15E 0.9700 . ?
C15' H15F 0.9700 . ?
C16' C17' 1.504(7) . ?
C16' H16E 0.9700 . ?
C16' H16F 0.9700 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
N1" C13" 1.313(6) . ?
N1" C2" 1.350(4) . ?
N1 C13 1.320(5) . ?
N1 C2 1.352(5) . ?
C2 C10 1.405(5) . ?
C2 C3 1.434(5) . ?
C3 C4 1.389(5) . ?
C3 C8 1.415(6) . ?
C4 N5 1.335(4) . ?
C4 H4A 0.9300 . ?
N5 C6 1.351(6) . ?
C6 C7 1.371(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.400(5) . ?
C7 H7A 0.9300 . ?
C8 N9 1.362(5) . ?
N9 C10 1.380(6) . ?
N9 H9A 0.8600 . ?
C10 C11 1.397(5) . ?
C11 C12 1.373(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.405(5) . ?
C12 H12A 0.9300 . ?
C13 O14 1.365(5) . ?
O14 C15 1.432(5) . ?
C15 C16 1.513(5) . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C16 C17 1.509(7) . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O14" C13" 1.369(4) . ?
O14" C15" 1.433(5) . ?
C2" C10" 1.405(4) . ?
C2" C3" 1.437(5) . ?
N9" C8" 1.360(4) . ?
N9" C10" 1.379(6) . ?
N9" H9"A 0.8600 . ?
C17" C16" 1.513(5) . ?
C17" H17G 0.9600 . ?
C17" H17H 0.9600 . ?
C17" H17I 0.9600 . ?
C16" C15" 1.511(4) . ?
C16" H16A 0.9700 . ?
C16" H16B 0.9700 . ?
C15" H15A 0.9700 . ?
C15" H15B 0.9700 . ?
C13" C12" 1.409(5) . ?
C3" C4" 1.390(5) . ?
C3" C8" 1.415(5) . ?
C4" N5" 1.334(5) . ?
C4" H4"A 0.9300 . ?
N5" C6" 1.350(5) . ?
C6" C7" 1.369(5) . ?
C6" H6"A 0.9300 . ?
C10" C11" 1.394(5) . ?
C8" C7" 1.395(5) . ?
C7" H7"A 0.9300 . ?
C11" C12" 1.373(5) . ?
C11" H11C 0.9300 . ?
C12" H12C 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13' N1' C2' 114.5(3) . . ?
N1' C2' C10' 124.1(3) . . ?
N1' C2' C3' 129.7(3) . . ?
C10' C2' C3' 106.2(4) . . ?
C4' C3' C8' 118.3(4) . . ?
C4' C3' C2' 135.6(3) . . ?
C8' C3' C2' 106.1(3) . . ?
N5' C4' C3' 122.4(4) . . ?
N5' C4' H4'A 118.7 . . ?
C3' C4' H4'A 118.9 . . ?
C4' N5' C6' 117.7(3) . . ?
N5' C6' C7' 125.7(5) . . ?
N5' C6' H6'A 117.2 . . ?
C7' C6' H6'A 117.1 . . ?
C6' C7' C8' 115.9(6) . . ?
C6' C7' H7'A 122.1 . . ?
C8' C7' H7'A 122.0 . . ?
N9' C8' C7' 130.1(4) . . ?
N9' C8' C3' 109.9(3) . . ?
C7' C8' C3' 120.0(4) . . ?
C8' N9' C10' 108.1(3) . . ?
C8' N9' H9'A 125.9 . . ?
C10' N9' H9'A 126.0 . . ?
N9' C10' C11' 130.7(5) . . ?
N9' C10' C2' 109.8(3) . . ?
C11' C10' C2' 119.6(5) . . ?
C12' C11' C10' 116.4(5) . . ?
C12' C11' H11B 121.8 . . ?
C10' C11' H11B 121.8 . . ?
C11' C12' C13' 119.5(4) . . ?
C11' C12' H12B 120.1 . . ?
C13' C12' H12B 120.4 . . ?
N1' C13' O14' 120.0(4) . . ?
N1' C13' C12' 125.9(3) . . ?
O14' C13' C12' 114.1(4) . . ?
C13' O14' C15' 117.1(3) . . ?
O14' C15' C16' 107.9(4) . . ?
O14' C15' H15E 110.1 . . ?
C16' C15' H15E 110.1 . . ?
O14' C15' H15F 110.3 . . ?
C16' C15' H15F 110.0 . . ?
H15E C15' H15F 108.5 . . ?
C17' C16' C15' 112.6(6) . . ?
C17' C16' H16E 109.0 . . ?
C15' C16' H16E 109.0 . . ?
C17' C16' H16F 109.1 . . ?
C15' C16' H16F 109.1 . . ?
H16E C16' H16F 107.9 . . ?
C16' C17' H17D 109.7 . . ?
C16' C17' H17E 109.4 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.3 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C13" N1" C2" 114.7(3) . . ?
C13 N1 C2 114.3(3) . . ?
N1 C2 C10 124.2(3) . . ?
N1 C2 C3 129.9(4) . . ?
C10 C2 C3 106.0(3) . . ?
C4 C3 C8 117.7(4) . . ?
C4 C3 C2 135.7(3) . . ?
C8 C3 C2 106.6(4) . . ?
N5 C4 C3 122.7(4) . . ?
N5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.6 . . ?
C4 N5 C6 117.8(3) . . ?
N5 C6 C7 125.5(4) . . ?
N5 C6 H6A 117.2 . . ?
C7 C6 H6A 117.3 . . ?
C6 C7 C8 115.8(5) . . ?
C6 C7 H7A 122.0 . . ?
C8 C7 H7A 122.2 . . ?
N9 C8 C7 130.2(3) . . ?
N9 C8 C3 109.3(3) . . ?
C7 C8 C3 120.5(3) . . ?
C8 N9 C10 108.4(3) . . ?
C8 N9 H9A 125.9 . . ?
C10 N9 H9A 125.7 . . ?
N9 C10 C11 130.4(4) . . ?
N9 C10 C2 109.7(3) . . ?
C11 C10 C2 119.9(5) . . ?
C12 C11 C10 115.9(5) . . ?
C12 C11 H11A 122.1 . . ?
C10 C11 H11A 122.0 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
N1 C13 O14 119.5(3) . . ?
N1 C13 C12 125.7(4) . . ?
O14 C13 C12 114.8(4) . . ?
C13 O14 C15 117.3(3) . . ?
O14 C15 C16 107.5(4) . . ?
O14 C15 H15C 110.2 . . ?
C16 C15 H15C 110.2 . . ?
O14 C15 H15D 110.2 . . ?
C16 C15 H15D 110.2 . . ?
H15C C15 H15D 108.5 . . ?
C15 C16 C17 112.4(4) . . ?
C15 C16 H16C 109.1 . . ?
C17 C16 H16C 109.1 . . ?
C15 C16 H16D 109.2 . . ?
C17 C16 H16D 109.1 . . ?
H16C C16 H16D 107.8 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13" O14" C15" 117.5(3) . . ?
N1" C2" C10" 124.3(4) . . ?
N1" C2" C3" 129.9(3) . . ?
C10" C2" C3" 105.8(3) . . ?
C8" N9" C10" 108.2(3) . . ?
C8" N9" H9"A 125.9 . . ?
C10" N9" H9"A 125.9 . . ?
C16" C17" H17G 109.3 . . ?
C16" C17" H17H 109.5 . . ?
H17G C17" H17H 109.5 . . ?
C16" C17" H17I 109.5 . . ?
H17G C17" H17I 109.5 . . ?
H17H C17" H17I 109.5 . . ?
C17" C16" C15" 111.7(4) . . ?
C17" C16" H16A 109.3 . . ?
C15" C16" H16A 109.3 . . ?
C17" C16" H16B 109.3 . . ?
C15" C16" H16B 109.3 . . ?
H16A C16" H16B 107.9 . . ?
O14" C15" C16" 107.5(3) . . ?
O14" C15" H15A 110.2 . . ?
C16" C15" H15A 110.3 . . ?
O14" C15" H15B 110.1 . . ?
C16" C15" H15B 110.3 . . ?
H15A C15" H15B 108.5 . . ?
N1" C13" O14" 119.8(4) . . ?
N1" C13" C12" 126.0(4) . . ?
O14" C13" C12" 114.2(4) . . ?
C4" C3" C8" 118.0(3) . . ?
C4" C3" C2" 135.6(3) . . ?
C8" C3" C2" 106.3(3) . . ?
N5" C4" C3" 122.2(4) . . ?
N5" C4" H4"A 118.9 . . ?
C3" C4" H4"A 118.9 . . ?
C4" N5" C6" 118.2(3) . . ?
N5" C6" C7" 125.1(4) . . ?
N5" C6" H6"A 117.5 . . ?
C7" C6" H6"A 117.4 . . ?
N9" C10" C11" 131.0(7) . . ?
N9" C10" C2" 110.0(3) . . ?
C11" C10" C2" 119.1(7) . . ?
N9" C8" C7" 130.2(3) . . ?
N9" C8" C3" 109.7(3) . . ?
C7" C8" C3" 120.1(3) . . ?
C6" C7" C8" 116.4(4) . . ?
C6" C7" H7"A 121.8 . . ?
C8" C7" H7"A 121.8 . . ?
C12" C11" C10" 117.2(8) . . ?
C12" C11" H11C 121.3 . . ?
C10" C11" H11C 121.4 . . ?
C11" C12" C13" 118.8(5) . . ?
C11" C12" H12C 120.7 . . ?
C13" C12" H12C 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13' N1' C2' C10' -1.1(5) . . . . ?
C13' N1' C2' C3' 178.1(4) . . . . ?
N1' C2' C3' C4' -1.2(7) . . . . ?
C10' C2' C3' C4' 178.1(4) . . . . ?
N1' C2' C3' C8' -179.1(4) . . . . ?
C10' C2' C3' C8' 0.2(4) . . . . ?
C8' C3' C4' N5' -1.1(7) . . . . ?
C2' C3' C4' N5' -178.8(5) . . . . ?
C3' C4' N5' C6' 1.4(8) . . . . ?
C4' N5' C6' C7' -1.7(10) . . . . ?
N5' C6' C7' C8' 1.7(11) . . . . ?
C6' C7' C8' N9' 179.3(5) . . . . ?
C6' C7' C8' C3' -1.2(9) . . . . ?
C4' C3' C8' N9' -179.4(4) . . . . ?
C2' C3' C8' N9' -1.1(5) . . . . ?
C4' C3' C8' C7' 1.0(7) . . . . ?
C2' C3' C8' C7' 179.3(5) . . . . ?
C7' C8' N9' C10' -178.9(5) . . . . ?
C3' C8' N9' C10' 1.5(7) . . . . ?
C8' N9' C10' C11' 177.8(5) . . . . ?
C8' N9' C10' C2' -1.4(6) . . . . ?
N1' C2' C10' N9' -179.9(3) . . . . ?
C3' C2' C10' N9' 0.7(5) . . . . ?
N1' C2' C10' C11' 0.8(6) . . . . ?
C3' C2' C10' C11' -178.6(3) . . . . ?
N9' C10' C11' C12' -178.6(4) . . . . ?
C2' C10' C11' C12' 0.6(7) . . . . ?
C10' C11' C12' C13' -1.5(8) . . . . ?
C2' N1' C13' O14' -179.4(4) . . . . ?
C2' N1' C13' C12' 0.2(6) . . . . ?
C11' C12' C13' N1' 1.1(8) . . . . ?
C11' C12' C13' O14' -179.2(6) . . . . ?
N1' C13' O14' C15' -2.0(6) . . . . ?
C12' C13' O14' C15' 178.4(4) . . . . ?
C13' O14' C15' C16' 179.9(3) . . . . ?
O14' C15' C16' C17' 172.8(3) . . . . ?
C13 N1 C2 C10 -0.6(6) . . . . ?
C13 N1 C2 C3 178.1(4) . . . . ?
N1 C2 C3 C4 -0.6(9) . . . . ?
C10 C2 C3 C4 178.3(4) . . . . ?
N1 C2 C3 C8 -179.3(3) . . . . ?
C10 C2 C3 C8 -0.4(7) . . . . ?
C8 C3 C4 N5 -0.5(7) . . . . ?
C2 C3 C4 N5 -179.1(4) . . . . ?
C3 C4 N5 C6 0.8(8) . . . . ?
C4 N5 C6 C7 -0.9(9) . . . . ?
N5 C6 C7 C8 0.8(10) . . . . ?
C6 C7 C8 N9 178.7(6) . . . . ?
C6 C7 C8 C3 -0.5(9) . . . . ?
C4 C3 C8 N9 -179.0(4) . . . . ?
C2 C3 C8 N9 0.0(9) . . . . ?
C4 C3 C8 C7 0.4(8) . . . . ?
C2 C3 C8 C7 179.3(3) . . . . ?
C7 C8 N9 C10 -178.8(4) . . . . ?
C3 C8 N9 C10 0.4(9) . . . . ?
C8 N9 C10 C11 178.4(6) . . . . ?
C8 N9 C10 C2 -0.7(6) . . . . ?
N1 C2 C10 N9 179.6(5) . . . . ?
C3 C2 C10 N9 0.7(4) . . . . ?
N1 C2 C10 C11 0.4(7) . . . . ?
C3 C2 C10 C11 -178.5(3) . . . . ?
N9 C10 C11 C12 -178.4(4) . . . . ?
C2 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C2 N1 C13 O14 -179.9(4) . . . . ?
C2 N1 C13 C12 -0.2(5) . . . . ?
C11 C12 C13 N1 1.3(7) . . . . ?
C11 C12 C13 O14 -179.0(4) . . . . ?
N1 C13 O14 C15 -1.5(5) . . . . ?
C12 C13 O14 C15 178.8(3) . . . . ?
C13 O14 C15 C16 179.8(3) . . . . ?
O14 C15 C16 C17 172.9(3) . . . . ?
C13" N1" C2" C10" -1.0(6) . . . . ?
C13" N1" C2" C3" 178.4(6) . . . . ?
C13" O14" C15" C16" 179.7(3) . . . . ?
C17" C16" C15" O14" 172.8(3) . . . . ?
C2" N1" C13" O14" -179.5(5) . . . . ?
C2" N1" C13" C12" 0.4(5) . . . . ?
C15" O14" C13" N1" -1.8(7) . . . . ?
C15" O14" C13" C12" 178.3(4) . . . . ?
N1" C2" C3" C4" -1.3(11) . . . . ?
C10" C2" C3" C4" 178.2(4) . . . . ?
N1" C2" C3" C8" -179.6(4) . . . . ?
C10" C2" C3" C8" -0.1(6) . . . . ?
C8" C3" C4" N5" -0.3(5) . . . . ?
C2" C3" C4" N5" -178.4(7) . . . . ?
C3" C4" N5" C6" 0.4(6) . . . . ?
C4" N5" C6" C7" -0.3(6) . . . . ?
C8" N9" C10" C11" 178.3(4) . . . . ?
C8" N9" C10" C2" -0.8(4) . . . . ?
N1" C2" C10" N9" -179.9(4) . . . . ?
C3" C2" C10" N9" 0.5(5) . . . . ?
N1" C2" C10" C11" 0.8(7) . . . . ?
C3" C2" C10" C11" -178.7(3) . . . . ?
C10" N9" C8" C7" -178.2(4) . . . . ?
C10" N9" C8" C3" 0.7(5) . . . . ?
C4" C3" C8" N9" -179.0(3) . . . . ?
C2" C3" C8" N9" -0.4(6) . . . . ?
C4" C3" C8" C7" 0.0(6) . . . . ?
C2" C3" C8" C7" 178.7(5) . . . . ?
N5" C6" C7" C8" 0.1(6) . . . . ?
N9" C8" C7" C6" 178.9(4) . . . . ?
C3" C8" C7" C6" 0.1(5) . . . . ?
N9" C10" C11" C12" -179.0(4) . . . . ?
C2" C10" C11" C12" 0.0(7) . . . . ?
C10" C11" C12" C13" -0.6(6) . . . . ?
N1" C13" C12" C11" 0.4(6) . . . . ?
O14" C13" C12" C11" -179.7(5) . . . . ?

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
N9 H9A N5 0.86 1.98 2.839(4) 177.8 8_564
N9' H9'A N5' 0.86 1.98 2.839(4) 177.3 8_564
N9" H9"A N5" 0.86 1.98 2.839(4) 178.0 8_564

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cook133
_database_code_depnum_ccdc_archive 'CCDC 1040832'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H42 N6 O3'
_chemical_formula_sum            'C42 H42 N6 O3'
_chemical_formula_weight         678.82

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   9.1046(2)
_cell_length_b                   10.2134(2)
_cell_length_c                   19.7287(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6870(10)
_cell_angle_gamma                90.00
_cell_volume                     1834.42(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.253
_exptl_crystal_size_mid          0.479
_exptl_crystal_size_max          0.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.079
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  0.9803

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
# APEX 2 parameters
_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 SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11850
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.03
_diffrn_reflns_theta_max         29.15
_reflns_number_total             6765
_reflns_number_gt                5986
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0558P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_number_reflns         6765
_refine_ls_number_parameters     466
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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
N1 N 0.71000(14) 0.80957(14) 0.35154(7) 0.0214(3) Uani 1 1 d . . .
C2 C 0.59577(17) 0.72867(17) 0.36342(8) 0.0209(3) Uani 1 1 d . . .
H2A H 0.5934 0.6468 0.3428 0.025 Uiso 1 1 calc R . .
C3 C 0.48306(16) 0.76453(16) 0.40516(8) 0.0188(3) Uani 1 1 d . . .
N4 N 0.35918(15) 0.69654(15) 0.42531(7) 0.0231(3) Uani 1 1 d . . .
H4A H 0.3369 0.6175 0.4142 0.028 Uiso 1 1 calc R . .
C5 C 0.27784(17) 0.77794(18) 0.46636(8) 0.0221(3) Uani 1 1 d . . .
C6 C 0.14354(18) 0.7541(2) 0.49836(9) 0.0304(4) Uani 1 1 d . . .
H6A H 0.0950 0.6745 0.4934 0.037 Uiso 1 1 calc R . .
C7 C 0.08654(19) 0.8529(2) 0.53735(10) 0.0345(5) Uani 1 1 d . . .
H7A H -0.0029 0.8395 0.5586 0.041 Uiso 1 1 calc R . .
C8 C 0.1583(2) 0.9729(2) 0.54624(10) 0.0315(4) Uani 1 1 d . . .
H8A H 0.1164 1.0372 0.5732 0.038 Uiso 1 1 calc R . .
C9 C 0.29145(18) 0.99659(19) 0.51513(8) 0.0254(4) Uani 1 1 d . . .
H9A H 0.3397 1.0761 0.5210 0.030 Uiso 1 1 calc R . .
C10 C 0.35113(16) 0.89868(17) 0.47500(8) 0.0197(3) Uani 1 1 d . . .
C11 C 0.48467(16) 0.89009(16) 0.43579(8) 0.0179(3) Uani 1 1 d . . .
C12 C 0.60263(17) 0.97198(16) 0.42458(8) 0.0197(3) Uani 1 1 d . . .
H12A H 0.6088 1.0541 0.4448 0.024 Uiso 1 1 calc R . .
C13 C 0.71195(17) 0.92665(17) 0.38173(8) 0.0202(3) Uani 1 1 d . . .
O14 O 0.82658(12) 1.00926(13) 0.37246(6) 0.0269(3) Uani 1 1 d . . .
C15 C 0.93309(17) 0.98137(19) 0.31989(10) 0.0282(4) Uani 1 1 d . . .
H15A H 0.9611 0.8888 0.3218 0.034 Uiso 1 1 calc R . .
C16 C 0.8679(2) 1.0120(3) 0.25129(10) 0.0434(5) Uani 1 1 d . . .
H16A H 0.7823 0.9589 0.2437 0.065 Uiso 1 1 calc R . .
H16B H 0.9389 0.9939 0.2169 0.065 Uiso 1 1 calc R . .
H16C H 0.8410 1.1028 0.2494 0.065 Uiso 1 1 calc R . .
C17 C 1.0641(2) 1.0656(2) 0.33823(12) 0.0428(5) Uani 1 1 d . . .
H17A H 1.0997 1.0422 0.3826 0.064 Uiso 1 1 calc R . .
H17B H 1.0356 1.1561 0.3379 0.064 Uiso 1 1 calc R . .
H17C H 1.1404 1.0520 0.3058 0.064 Uiso 1 1 calc R . .
N1' N 0.21883(14) 0.51643(14) 0.32910(7) 0.0214(3) Uani 1 1 d . . .
C2' C 0.09654(17) 0.59039(17) 0.32452(8) 0.0213(3) Uani 1 1 d . . .
H2'A H 0.0833 0.6582 0.3553 0.026 Uiso 1 1 calc R . .
C3' C -0.00920(17) 0.56820(16) 0.27543(8) 0.0200(3) Uani 1 1 d . . .
N4' N -0.14056(15) 0.63222(15) 0.26180(8) 0.0257(3) Uani 1 1 d . . .
H4'A H -0.1738 0.6990 0.2833 0.031 Uiso 1 1 calc R . .
C5' C -0.20844(18) 0.57039(18) 0.20804(9) 0.0254(4) Uani 1 1 d . . .
C6' C -0.3450(2) 0.5973(2) 0.17747(10) 0.0350(4) Uani 1 1 d . . .
H6'A H -0.4037 0.6657 0.1924 0.042 Uiso 1 1 calc R . .
C7' C -0.3885(2) 0.5184(2) 0.12454(11) 0.0435(5) Uani 1 1 d . . .
H7'A H -0.4790 0.5338 0.1037 0.052 Uiso 1 1 calc R . .
C8' C -0.3016(3) 0.4160(2) 0.10091(12) 0.0474(6) Uani 1 1 d . . .
H8'A H -0.3347 0.3652 0.0647 0.057 Uiso 1 1 calc R . .
C9' C -0.1667(2) 0.3891(2) 0.13086(10) 0.0366(5) Uani 1 1 d . . .
H9'A H -0.1083 0.3212 0.1150 0.044 Uiso 1 1 calc R . .
C10' C -0.12045(19) 0.46618(18) 0.18534(9) 0.0249(4) Uani 1 1 d . . .
C11' C 0.00872(18) 0.46483(17) 0.22878(8) 0.0211(3) Uani 1 1 d . . .
C12' C 0.13452(18) 0.38886(17) 0.23355(9) 0.0243(4) Uani 1 1 d . . .
H12C H 0.1504 0.3195 0.2040 0.029 Uiso 1 1 calc R . .
C13' C 0.23577(18) 0.42004(17) 0.28405(9) 0.0232(3) Uani 1 1 d . . .
O14' O 0.36124(13) 0.34748(14) 0.28471(6) 0.0315(3) Uani 1 1 d . . .
C15' C 0.45432(17) 0.34788(18) 0.34478(9) 0.0276(4) Uani 1 1 d . . .
H15C H 0.4697 0.4381 0.3602 0.033 Uiso 1 1 calc R . .
C16' C 0.59859(19) 0.2901(2) 0.32257(11) 0.0393(5) Uani 1 1 d . . .
H16G H 0.6354 0.3392 0.2849 0.059 Uiso 1 1 calc R . .
H16H H 0.5839 0.2006 0.3092 0.059 Uiso 1 1 calc R . .
H16I H 0.6682 0.2936 0.3595 0.059 Uiso 1 1 calc R . .
C17' C 0.3819(2) 0.2695(2) 0.39988(10) 0.0332(4) Uani 1 1 d . . .
H17G H 0.2913 0.3107 0.4122 0.050 Uiso 1 1 calc R . .
H17H H 0.4460 0.2653 0.4388 0.050 Uiso 1 1 calc R . .
H17I H 0.3623 0.1825 0.3837 0.050 Uiso 1 1 calc R . .
N1" N 0.09717(15) 0.23936(15) -0.01425(7) 0.0251(3) Uani 1 1 d . . .
C2" C 0.05603(17) 0.11802(18) 0.00230(9) 0.0239(4) Uani 1 1 d . . .
H2"A H -0.0154 0.0757 -0.0237 0.029 Uiso 1 1 calc R . .
C3" C 0.11841(17) 0.05412(17) 0.05772(8) 0.0208(3) Uani 1 1 d . . .
N4" N 0.09623(15) -0.07023(15) 0.08289(7) 0.0244(3) Uani 1 1 d . . .
H4"A H 0.0359 -0.1273 0.0667 0.029 Uiso 1 1 calc R . .
C5" C 0.18752(17) -0.08751(17) 0.13866(8) 0.0219(3) Uani 1 1 d . . .
C6" C 0.20736(19) -0.19764(19) 0.17943(9) 0.0284(4) Uani 1 1 d . . .
H6"A H 0.1544 -0.2742 0.1717 0.034 Uiso 1 1 calc R . .
C7" C 0.30883(19) -0.1886(2) 0.23186(9) 0.0317(4) Uani 1 1 d . . .
H7"A H 0.3248 -0.2611 0.2595 0.038 Uiso 1 1 calc R . .
C8" C 0.38803(19) -0.0743(2) 0.24463(9) 0.0300(4) Uani 1 1 d . . .
H8"A H 0.4549 -0.0719 0.2806 0.036 Uiso 1 1 calc R . .
C9" C 0.36870(17) 0.03555(19) 0.20458(8) 0.0230(4) Uani 1 1 d . . .
H9"A H 0.4211 0.1120 0.2133 0.028 Uiso 1 1 calc R . .
C10" C 0.26795(16) 0.02847(17) 0.15049(8) 0.0197(3) Uani 1 1 d . . .
C11" C 0.22493(16) 0.11920(16) 0.09818(8) 0.0181(3) Uani 1 1 d . . .
C12" C 0.26902(17) 0.24451(17) 0.07957(8) 0.0212(3) Uani 1 1 d . . .
H12B H 0.3403 0.2898 0.1042 0.025 Uiso 1 1 calc R . .
C13" C 0.20228(18) 0.29863(17) 0.02293(9) 0.0226(3) Uani 1 1 d . . .
O14" O 0.24116(14) 0.42235(13) 0.00352(6) 0.0288(3) Uani 1 1 d . . .
C15" C 0.30670(19) 0.42956(19) -0.06353(9) 0.0281(4) Uani 1 1 d . . .
H15B H 0.2418 0.3867 -0.0967 0.034 Uiso 1 1 calc R . .
C16" C 0.4540(2) 0.3630(2) -0.06304(10) 0.0343(4) Uani 1 1 d . . .
H16D H 0.4435 0.2748 -0.0470 0.051 Uiso 1 1 calc R . .
H16E H 0.5204 0.4098 -0.0337 0.051 Uiso 1 1 calc R . .
H16F H 0.4923 0.3617 -0.1082 0.051 Uiso 1 1 calc R . .
C17" C 0.3176(3) 0.5724(2) -0.07986(13) 0.0496(6) Uani 1 1 d . . .
H17D H 0.2212 0.6105 -0.0802 0.074 Uiso 1 1 calc R . .
H17E H 0.3609 0.5831 -0.1236 0.074 Uiso 1 1 calc R . .
H17F H 0.3776 0.6152 -0.0462 0.074 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.336(2) . ?
N1 C2 1.351(2) . ?
C2 C3 1.373(2) . ?
C2 H2A 0.9300 . ?
C3 N4 1.387(2) . ?
C3 C11 1.418(2) . ?
N4 C5 1.382(2) . ?
N4 H4A 0.8600 . ?
C5 C6 1.404(2) . ?
C5 C10 1.411(2) . ?
C6 C7 1.374(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.399(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.387(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.452(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.393(2) . ?
C12 H12A 0.9300 . ?
C13 O14 1.356(2) . ?
O14 C15 1.456(2) . ?
C15 C16 1.504(3) . ?
C15 C17 1.511(3) . ?
C15 H15A 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1' C13' 1.336(2) . ?
N1' C2' 1.348(2) . ?
C2' C3' 1.376(2) . ?
C2' H2'A 0.9300 . ?
C3' N4' 1.387(2) . ?
C3' C11' 1.411(2) . ?
N4' C5' 1.375(2) . ?
N4' H4'A 0.8600 . ?
C5' C6' 1.403(2) . ?
C5' C10' 1.408(2) . ?
C6' C7' 1.374(3) . ?
C6' H6'A 0.9300 . ?
C7' C8' 1.395(3) . ?
C7' H7'A 0.9300 . ?
C8' C9' 1.385(3) . ?
C8' H8'A 0.9300 . ?
C9' C10' 1.393(3) . ?
C9' H9'A 0.9300 . ?
C10' C11' 1.447(2) . ?
C11' C12' 1.386(2) . ?
C12' C13' 1.386(2) . ?
C12' H12C 0.9300 . ?
C13' O14' 1.3616(19) . ?
O14' C15' 1.449(2) . ?
C15' C17' 1.509(3) . ?
C15' C16' 1.510(2) . ?
C15' H15C 0.9800 . ?
C16' H16G 0.9600 . ?
C16' H16H 0.9600 . ?
C16' H16I 0.9600 . ?
C17' H17G 0.9600 . ?
C17' H17H 0.9600 . ?
C17' H17I 0.9600 . ?
N1" C2" 1.336(2) . ?
N1" C13" 1.343(2) . ?
C2" C3" 1.389(2) . ?
C2" H2"A 0.9300 . ?
C3" N4" 1.379(2) . ?
C3" C11" 1.414(2) . ?
N4" C5" 1.382(2) . ?
N4" H4"A 0.8600 . ?
C5" C6" 1.393(2) . ?
C5" C10" 1.411(2) . ?
C6" C7" 1.382(3) . ?
C6" H6"A 0.9300 . ?
C7" C8" 1.393(3) . ?
C7" H7"A 0.9300 . ?
C8" C9" 1.382(3) . ?
C8" H8"A 0.9300 . ?
C9" C10" 1.401(2) . ?
C9" H9"A 0.9300 . ?
C10" C11" 1.438(2) . ?
C11" C12" 1.392(2) . ?
C12" C13" 1.381(2) . ?
C12" H12B 0.9300 . ?
C13" O14" 1.368(2) . ?
O14" C15" 1.460(2) . ?
C15" C17" 1.498(3) . ?
C15" C16" 1.504(3) . ?
C15" H15B 0.9800 . ?
C16" H16D 0.9600 . ?
C16" H16E 0.9600 . ?
C16" H16F 0.9600 . ?
C17" H17D 0.9600 . ?
C17" H17E 0.9600 . ?
C17" H17F 0.9600 . ?

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
C13 N1 C2 118.44(13) . . ?
N1 C2 C3 121.55(15) . . ?
N1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 N4 130.88(15) . . ?
C2 C3 C11 119.54(15) . . ?
N4 C3 C11 109.58(13) . . ?
C5 N4 C3 108.07(14) . . ?
C5 N4 H4A 126.0 . . ?
C3 N4 H4A 126.0 . . ?
N4 C5 C6 129.41(17) . . ?
N4 C5 C10 109.91(13) . . ?
C6 C5 C10 120.67(17) . . ?
C7 C6 C5 117.46(18) . . ?
C7 C6 H6A 121.3 . . ?
C5 C6 H6A 121.3 . . ?
C6 C7 C8 122.30(17) . . ?
C6 C7 H7A 118.9 . . ?
C8 C7 H7A 118.9 . . ?
C9 C8 C7 120.48(18) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 118.43(17) . . ?
C8 C9 H9A 120.8 . . ?
C10 C9 H9A 120.8 . . ?
C9 C10 C5 120.65(15) . . ?
C9 C10 C11 133.05(16) . . ?
C5 C10 C11 106.30(14) . . ?
C12 C11 C3 118.93(14) . . ?
C12 C11 C10 134.96(15) . . ?
C3 C11 C10 106.10(14) . . ?
C11 C12 C13 117.30(15) . . ?
C11 C12 H12A 121.4 . . ?
C13 C12 H12A 121.4 . . ?
N1 C13 O14 120.19(14) . . ?
N1 C13 C12 124.22(15) . . ?
O14 C13 C12 115.58(15) . . ?
C13 O14 C15 119.63(13) . . ?
O14 C15 C16 109.94(14) . . ?
O14 C15 C17 104.40(15) . . ?
C16 C15 C17 113.50(18) . . ?
O14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C17 C15 H15A 109.6 . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13' N1' C2' 118.04(14) . . ?
N1' C2' C3' 121.70(15) . . ?
N1' C2' H2'A 119.2 . . ?
C3' C2' H2'A 119.2 . . ?
C2' C3' N4' 130.80(15) . . ?
C2' C3' C11' 119.78(14) . . ?
N4' C3' C11' 109.41(14) . . ?
C5' N4' C3' 108.17(14) . . ?
C5' N4' H4'A 125.9 . . ?
C3' N4' H4'A 125.9 . . ?
N4' C5' C6' 129.03(17) . . ?
N4' C5' C10' 109.90(14) . . ?
C6' C5' C10' 121.06(17) . . ?
C7' C6' C5' 117.25(19) . . ?
C7' C6' H6'A 121.4 . . ?
C5' C6' H6'A 121.4 . . ?
C6' C7' C8' 122.32(19) . . ?
C6' C7' H7'A 118.8 . . ?
C8' C7' H7'A 118.8 . . ?
C9' C8' C7' 120.7(2) . . ?
C9' C8' H8'A 119.7 . . ?
C7' C8' H8'A 119.7 . . ?
C8' C9' C10' 118.38(19) . . ?
C8' C9' H9'A 120.8 . . ?
C10' C9' H9'A 120.8 . . ?
C9' C10' C5' 120.31(16) . . ?
C9' C10' C11' 133.41(17) . . ?
C5' C10' C11' 106.28(15) . . ?
C12' C11' C3' 118.46(15) . . ?
C12' C11' C10' 135.30(16) . . ?
C3' C11' C10' 106.24(14) . . ?
C11' C12' C13' 117.52(15) . . ?
C11' C12' H12C 121.2 . . ?
C13' C12' H12C 121.2 . . ?
N1' C13' O14' 119.87(15) . . ?
N1' C13' C12' 124.48(15) . . ?
O14' C13' C12' 115.62(15) . . ?
C13' O14' C15' 119.27(13) . . ?
O14' C15' C17' 109.36(14) . . ?
O14' C15' C16' 105.31(15) . . ?
C17' C15' C16' 113.01(16) . . ?
O14' C15' H15C 109.7 . . ?
C17' C15' H15C 109.7 . . ?
C16' C15' H15C 109.7 . . ?
C15' C16' H16G 109.5 . . ?
C15' C16' H16H 109.5 . . ?
H16G C16' H16H 109.5 . . ?
C15' C16' H16I 109.5 . . ?
H16G C16' H16I 109.5 . . ?
H16H C16' H16I 109.5 . . ?
C15' C17' H17G 109.5 . . ?
C15' C17' H17H 109.5 . . ?
H17G C17' H17H 109.5 . . ?
C15' C17' H17I 109.5 . . ?
H17G C17' H17I 109.5 . . ?
H17H C17' H17I 109.5 . . ?
C2" N1" C13" 118.98(15) . . ?
N1" C2" C3" 120.99(16) . . ?
N1" C2" H2"A 119.5 . . ?
C3" C2" H2"A 119.5 . . ?
N4" C3" C2" 130.97(16) . . ?
N4" C3" C11" 109.39(14) . . ?
C2" C3" C11" 119.64(15) . . ?
C3" N4" C5" 108.35(14) . . ?
C3" N4" H4"A 125.8 . . ?
C5" N4" H4"A 125.8 . . ?
N4" C5" C6" 129.43(16) . . ?
N4" C5" C10" 109.30(15) . . ?
C6" C5" C10" 121.26(15) . . ?
C7" C6" C5" 117.33(17) . . ?
C7" C6" H6"A 121.3 . . ?
C5" C6" H6"A 121.3 . . ?
C6" C7" C8" 122.09(17) . . ?
C6" C7" H7"A 119.0 . . ?
C8" C7" H7"A 119.0 . . ?
C9" C8" C7" 120.97(16) . . ?
C9" C8" H8"A 119.5 . . ?
C7" C8" H8"A 119.5 . . ?
C8" C9" C10" 118.12(17) . . ?
C8" C9" H9"A 120.9 . . ?
C10" C9" H9"A 120.9 . . ?
C9" C10" C5" 120.22(16) . . ?
C9" C10" C11" 133.14(16) . . ?
C5" C10" C11" 106.62(14) . . ?
C12" C11" C3" 118.77(15) . . ?
C12" C11" C10" 134.82(15) . . ?
C3" C11" C10" 106.33(14) . . ?
C13" C12" C11" 117.12(15) . . ?
C13" C12" H12B 121.4 . . ?
C11" C12" H12B 121.4 . . ?
N1" C13" O14" 116.64(15) . . ?
N1" C13" C12" 124.42(16) . . ?
O14" C13" C12" 118.91(15) . . ?
C13" O14" C15" 114.22(14) . . ?
O14" C15" C17" 105.84(17) . . ?
O14" C15" C16" 110.22(15) . . ?
C17" C15" C16" 112.37(16) . . ?
O14" C15" H15B 109.4 . . ?
C17" C15" H15B 109.4 . . ?
C16" C15" H15B 109.4 . . ?
C15" C16" H16D 109.5 . . ?
C15" C16" H16E 109.5 . . ?
H16D C16" H16E 109.5 . . ?
C15" C16" H16F 109.5 . . ?
H16D C16" H16F 109.5 . . ?
H16E C16" H16F 109.5 . . ?
C15" C17" H17D 109.5 . . ?
C15" C17" H17E 109.5 . . ?
H17D C17" H17E 109.5 . . ?
C15" C17" H17F 109.5 . . ?
H17D C17" H17F 109.5 . . ?
H17E C17" H17F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C2 C3 0.3(2) . . . . ?
N1 C2 C3 N4 -178.21(15) . . . . ?
N1 C2 C3 C11 1.1(2) . . . . ?
C2 C3 N4 C5 -178.41(16) . . . . ?
C11 C3 N4 C5 2.26(18) . . . . ?
C3 N4 C5 C6 179.29(18) . . . . ?
C3 N4 C5 C10 -1.88(18) . . . . ?
N4 C5 C6 C7 179.42(17) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C5 -0.2(2) . . . . ?
C8 C9 C10 C11 179.84(17) . . . . ?
N4 C5 C10 C9 -179.22(14) . . . . ?
C6 C5 C10 C9 -0.3(2) . . . . ?
N4 C5 C10 C11 0.78(18) . . . . ?
C6 C5 C10 C11 179.73(15) . . . . ?
C2 C3 C11 C12 -2.1(2) . . . . ?
N4 C3 C11 C12 177.30(14) . . . . ?
C2 C3 C11 C10 178.83(14) . . . . ?
N4 C3 C11 C10 -1.75(17) . . . . ?
C9 C10 C11 C12 1.8(3) . . . . ?
C5 C10 C11 C12 -178.24(17) . . . . ?
C9 C10 C11 C3 -179.41(17) . . . . ?
C5 C10 C11 C3 0.59(17) . . . . ?
C3 C11 C12 C13 1.8(2) . . . . ?
C10 C11 C12 C13 -179.48(17) . . . . ?
C2 N1 C13 O14 178.30(14) . . . . ?
C2 N1 C13 C12 -0.6(2) . . . . ?
C11 C12 C13 N1 -0.5(2) . . . . ?
C11 C12 C13 O14 -179.42(14) . . . . ?
N1 C13 O14 C15 11.7(2) . . . . ?
C12 C13 O14 C15 -169.35(15) . . . . ?
C13 O14 C15 C16 74.8(2) . . . . ?
C13 O14 C15 C17 -163.09(16) . . . . ?
C13' N1' C2' C3' 0.3(2) . . . . ?
N1' C2' C3' N4' -179.58(16) . . . . ?
N1' C2' C3' C11' 0.7(2) . . . . ?
C2' C3' N4' C5' -178.74(17) . . . . ?
C11' C3' N4' C5' 1.05(19) . . . . ?
C3' N4' C5' C6' 177.92(18) . . . . ?
C3' N4' C5' C10' -0.90(19) . . . . ?
N4' C5' C6' C7' -179.02(19) . . . . ?
C10' C5' C6' C7' -0.3(3) . . . . ?
C5' C6' C7' C8' -0.6(3) . . . . ?
C6' C7' C8' C9' 0.5(4) . . . . ?
C7' C8' C9' C10' 0.4(3) . . . . ?
C8' C9' C10' C5' -1.3(3) . . . . ?
C8' C9' C10' C11' 178.4(2) . . . . ?
N4' C5' C10' C9' -179.80(17) . . . . ?
C6' C5' C10' C9' 1.3(3) . . . . ?
N4' C5' C10' C11' 0.40(19) . . . . ?
C6' C5' C10' C11' -178.53(17) . . . . ?
C2' C3' C11' C12' -0.6(2) . . . . ?
N4' C3' C11' C12' 179.55(15) . . . . ?
C2' C3' C11' C10' 179.03(15) . . . . ?
N4' C3' C11' C10' -0.78(18) . . . . ?
C9' C10' C11' C12' 0.1(4) . . . . ?
C5' C10' C11' C12' 179.82(19) . . . . ?
C9' C10' C11' C3' -179.5(2) . . . . ?
C5' C10' C11' C3' 0.23(18) . . . . ?
C3' C11' C12' C13' -0.3(2) . . . . ?
C10' C11' C12' C13' -179.86(19) . . . . ?
C2' N1' C13' O14' 176.57(15) . . . . ?
C2' N1' C13' C12' -1.4(2) . . . . ?
C11' C12' C13' N1' 1.4(3) . . . . ?
C11' C12' C13' O14' -176.66(15) . . . . ?
N1' C13' O14' C15' 18.2(2) . . . . ?
C12' C13' O14' C15' -163.61(15) . . . . ?
C13' O14' C15' C17' 73.0(2) . . . . ?
C13' O14' C15' C16' -165.26(16) . . . . ?
C13" N1" C2" C3" 1.1(2) . . . . ?
N1" C2" C3" N4" -178.13(16) . . . . ?
N1" C2" C3" C11" 1.3(2) . . . . ?
C2" C3" N4" C5" 178.94(17) . . . . ?
C11" C3" N4" C5" -0.54(18) . . . . ?
C3" N4" C5" C6" -177.85(17) . . . . ?
C3" N4" C5" C10" 1.14(18) . . . . ?
N4" C5" C6" C7" 178.92(16) . . . . ?
C10" C5" C6" C7" 0.0(2) . . . . ?
C5" C6" C7" C8" 0.6(3) . . . . ?
C6" C7" C8" C9" -0.4(3) . . . . ?
C7" C8" C9" C10" -0.4(3) . . . . ?
C8" C9" C10" C5" 1.1(2) . . . . ?
C8" C9" C10" C11" -177.24(16) . . . . ?
N4" C5" C10" C9" -179.99(14) . . . . ?
C6" C5" C10" C9" -0.9(2) . . . . ?
N4" C5" C10" C11" -1.27(17) . . . . ?
C6" C5" C10" C11" 177.82(15) . . . . ?
N4" C3" C11" C12" 176.95(14) . . . . ?
C2" C3" C11" C12" -2.6(2) . . . . ?
N4" C3" C11" C10" -0.24(17) . . . . ?
C2" C3" C11" C10" -179.79(14) . . . . ?
C9" C10" C11" C12" 2.9(3) . . . . ?
C5" C10" C11" C12" -175.61(17) . . . . ?
C9" C10" C11" C3" 179.39(16) . . . . ?
C5" C10" C11" C3" 0.91(17) . . . . ?
C3" C11" C12" C13" 1.5(2) . . . . ?
C10" C11" C12" C13" 177.65(16) . . . . ?
C2" N1" C13" O14" 179.49(14) . . . . ?
C2" N1" C13" C12" -2.4(2) . . . . ?
C11" C12" C13" N1" 1.1(2) . . . . ?
C11" C12" C13" O14" 179.12(14) . . . . ?
N1" C13" O14" C15" -63.80(19) . . . . ?
C12" C13" O14" C15" 117.98(16) . . . . ?
C13" O14" C15" C17" 170.77(16) . . . . ?
C13" O14" C15" C16" -67.5(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
N4" H4"A N1" 0.86 2.09 2.943(2) 172.0 2_545
N4' H4'A N1 0.86 2.06 2.8852(19) 160.6 1_455
N4 H4A N1' 0.86 2.24 2.926(2) 137.3 .

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cook142
_database_code_depnum_ccdc_archive 'CCDC 1040833'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N4 O2'
_chemical_formula_sum            'C28 H28 N4 O2'
_chemical_formula_weight         452.54

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'

_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+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, z'

_cell_length_a                   14.2584(5)
_cell_length_b                   14.3343(5)
_cell_length_c                   11.7845(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2408.57(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.204
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_max          0.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.080
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.984

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
# APEX 2 parameters
_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 SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28311
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.728
_diffrn_reflns_theta_max         29.165
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
#_diffrn_reflns_Laue_measured_fraction_max    0.997
#_diffrn_reflns_Laue_measured_fraction_full   0.998
#_diffrn_reflns_point_group_measured_fraction_max   0.995
#_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total             6485
_reflns_number_gt                5586
_reflns_threshold_expression     'I > 2σ(I)'
#_reflns_Friedel_coverage          0.782
#_reflns_Friedel_fraction_max      0.992
#_reflns_Friedel_fraction_full     1.000

_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       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_refine_special_details          
;
 ?
;
_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)+(0.0599P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_number_reflns         6485
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N1 N 0.48145(7) 0.13014(7) 0.56947(9) 0.0206(2) Uani 1 1 d . . .
C2 C 0.54999(9) 0.12587(9) 0.49029(10) 0.0208(3) Uani 1 1 d . . .
C3 C 0.65026(9) 0.13033(9) 0.50339(10) 0.0212(3) Uani 1 1 d . . .
C4 C 0.71083(9) 0.14205(9) 0.59578(11) 0.0240(3) Uani 1 1 d . . .
H4A H 0.6867 0.1496 0.6703 0.029 Uiso 1 1 calc R . .
C5 C 0.80652(10) 0.14244(10) 0.57654(12) 0.0297(3) Uani 1 1 d . . .
H5A H 0.8483 0.1513 0.6384 0.036 Uiso 1 1 calc R . .
C6 C 0.84260(10) 0.12999(11) 0.46690(12) 0.0325(3) Uani 1 1 d . . .
H6A H 0.9086 0.1297 0.4561 0.039 Uiso 1 1 calc R . .
C7 C 0.78437(10) 0.11814(11) 0.37416(12) 0.0297(3) Uani 1 1 d . . .
H7A H 0.8093 0.1093 0.3002 0.036 Uiso 1 1 calc R . .
C8 C 0.68792(9) 0.11960(9) 0.39283(10) 0.0236(3) Uani 1 1 d . . .
N9 N 0.61613(8) 0.11227(8) 0.31534(9) 0.0259(2) Uani 1 1 d . . .
H9A H 0.6227 0.1070 0.2414 0.031 Uiso 1 1 calc R . .
C10 C 0.53218(9) 0.11455(9) 0.37317(10) 0.0225(3) Uani 1 1 d . . .
C11 C 0.44070(10) 0.10701(10) 0.33558(10) 0.0258(3) Uani 1 1 d . . .
H11A H 0.4266 0.0996 0.2573 0.031 Uiso 1 1 calc R . .
C12 C 0.37107(9) 0.11059(10) 0.41583(11) 0.0249(3) Uani 1 1 d . . .
H12A H 0.3073 0.1050 0.3937 0.030 Uiso 1 1 calc R . .
C13 C 0.39429(9) 0.12248(9) 0.53106(10) 0.0214(3) Uani 1 1 d . . .
O14 O 0.32899(6) 0.12567(7) 0.61559(7) 0.0252(2) Uani 1 1 d . . .
C15 C 0.23240(8) 0.12206(10) 0.58062(11) 0.0251(3) Uani 1 1 d . . .
H15A H 0.2210 0.0650 0.5354 0.030 Uiso 1 1 calc R . .
H15B H 0.2175 0.1769 0.5328 0.030 Uiso 1 1 calc R . .
C16 C 0.17094(9) 0.12178(12) 0.68482(12) 0.0300(3) Uani 1 1 d . . .
H16A H 0.1841 0.1779 0.7312 0.036 Uiso 1 1 calc R . .
H16B H 0.1849 0.0660 0.7314 0.036 Uiso 1 1 calc R . .
C17 C 0.06765(9) 0.12103(13) 0.65003(14) 0.0378(4) Uani 1 1 d . . .
H17A H 0.0285 0.1111 0.7173 0.057 Uiso 1 1 calc R . .
H17B H 0.0568 0.0706 0.5954 0.057 Uiso 1 1 calc R . .
H17C H 0.0515 0.1809 0.6151 0.057 Uiso 1 1 calc R . .
N1' N 0.37432(7) -0.07021(8) 0.07129(9) 0.0207(2) Uani 1 1 d . . .
C2' C 0.42448(8) -0.11500(9) -0.00913(10) 0.0195(2) Uani 1 1 d . . .
C3' C 0.48888(9) -0.19195(9) 0.00088(10) 0.0226(3) Uani 1 1 d . . .
C4' C 0.51914(11) -0.24878(10) 0.08987(12) 0.0317(3) Uani 1 1 d . . .
H4'A H 0.4946 -0.2408 0.1642 0.038 Uiso 1 1 calc R . .
C5' C 0.58532(13) -0.31677(12) 0.06817(15) 0.0449(4) Uani 1 1 d . . .
H5'A H 0.6062 -0.3560 0.1280 0.054 Uiso 1 1 calc R . .
C6' C 0.62201(13) -0.32847(13) -0.04127(15) 0.0492(5) Uani 1 1 d . . .
H6'A H 0.6682 -0.3751 -0.0540 0.059 Uiso 1 1 calc R . .
C7' C 0.59279(11) -0.27401(13) -0.13061(14) 0.0395(4) Uani 1 1 d . . .
H7'A H 0.6182 -0.2822 -0.2044 0.047 Uiso 1 1 calc R . .
C8' C 0.52511(9) -0.20690(10) -0.10963(11) 0.0260(3) Uani 1 1 d . . .
N9' N 0.48379(8) -0.14579(8) -0.18448(9) 0.0254(2) Uani 1 1 d . . .
H9'A H 0.4941 -0.1434 -0.2580 0.031 Uiso 1 1 calc R . .
C10' C 0.42381(9) -0.08918(9) -0.12511(10) 0.0210(3) Uani 1 1 d . . .
C11' C 0.36837(10) -0.01584(9) -0.16010(11) 0.0263(3) Uani 1 1 d . . .
H11B H 0.3658 0.0024 -0.2375 0.032 Uiso 1 1 calc R . .
C12' C 0.31690(10) 0.02983(10) -0.07845(11) 0.0277(3) Uani 1 1 d . . .
H12B H 0.2775 0.0805 -0.0990 0.033 Uiso 1 1 calc R . .
C13' C 0.32271(9) 0.00120(10) 0.03595(10) 0.0228(3) Uani 1 1 d . . .
O14' O 0.27523(7) 0.04443(7) 0.12129(8) 0.0313(2) Uani 1 1 d . . .
C15' C 0.22190(11) 0.12655(12) 0.09075(13) 0.0385(4) Uani 1 1 d . . .
H15C H 0.1679 0.1086 0.0427 0.046 Uiso 1 1 calc R . .
H15D H 0.2619 0.1700 0.0469 0.046 Uiso 1 1 calc R . .
C16' C 0.18804(14) 0.17298(14) 0.19564(15) 0.0504(5) Uani 1 1 d . . .
H16C H 0.1584 0.2329 0.1744 0.060 Uiso 1 1 calc R . .
H16D H 0.2428 0.1874 0.2441 0.060 Uiso 1 1 calc R . .
C17' C 0.11896(14) 0.11717(17) 0.26419(19) 0.0684(6) Uani 1 1 d . . .
H17D H 0.0956 0.1553 0.3272 0.103 Uiso 1 1 calc R . .
H17E H 0.1499 0.0614 0.2943 0.103 Uiso 1 1 calc R . .
H17F H 0.0663 0.0985 0.2157 0.103 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.3273(15) . ?
N1 C2 1.3525(16) . ?
C2 C10 1.4127(16) . ?
C2 C3 1.4394(17) . ?
C3 C4 1.3998(17) . ?
C3 C8 1.4176(17) . ?
C4 C5 1.3831(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3830(19) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3929(19) . ?
C7 H7A 0.9500 . ?
C8 N9 1.3758(16) . ?
N9 C10 1.3778(17) . ?
N9 H9A 0.8800 . ?
C10 C11 1.3818(18) . ?
C11 C12 1.3720(19) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4081(16) . ?
C12 H12A 0.9500 . ?
C13 O14 1.3642(15) . ?
O14 C15 1.4384(14) . ?
C15 C16 1.5085(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5288(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1' C13' 1.3276(17) . ?
N1' C2' 1.3498(16) . ?
C2' C10' 1.4160(16) . ?
C2' C3' 1.4401(19) . ?
C3' C4' 1.3962(18) . ?
C3' C8' 1.4172(17) . ?
C4' C5' 1.380(2) . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.402(2) . ?
C5' H5'A 0.9500 . ?
C6' C7' 1.375(2) . ?
C6' H6'A 0.9500 . ?
C7' C8' 1.385(2) . ?
C7' H7'A 0.9500 . ?
C8' N9' 1.3758(18) . ?
N9' C10' 1.3709(17) . ?
N9' H9'A 0.8800 . ?
C10' C11' 1.3785(19) . ?
C11' C12' 1.376(2) . ?
C11' H11B 0.9500 . ?
C12' C13' 1.4117(17) . ?
C12' H12B 0.9500 . ?
C13' O14' 1.3615(15) . ?
O14' C15' 1.4468(17) . ?
C15' C16' 1.485(2) . ?
C15' H15C 0.9900 . ?
C15' H15D 0.9900 . ?
C16' C17' 1.504(3) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?

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
C13 N1 C2 115.95(10) . . ?
N1 C2 C10 123.32(12) . . ?
N1 C2 C3 129.91(11) . . ?
C10 C2 C3 106.77(11) . . ?
C4 C3 C8 119.61(11) . . ?
C4 C3 C2 134.56(12) . . ?
C8 C3 C2 105.83(10) . . ?
C5 C4 C3 118.79(12) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 120.83(13) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 121.58(13) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 117.77(13) . . ?
C6 C7 H7A 121.1 . . ?
C8 C7 H7A 121.1 . . ?
N9 C8 C7 128.94(12) . . ?
N9 C8 C3 109.67(11) . . ?
C7 C8 C3 121.39(12) . . ?
C8 N9 C10 108.44(10) . . ?
C8 N9 H9A 125.8 . . ?
C10 N9 H9A 125.8 . . ?
N9 C10 C11 131.28(12) . . ?
N9 C10 C2 109.25(11) . . ?
C11 C10 C2 119.47(12) . . ?
C12 C11 C10 117.33(11) . . ?
C12 C11 H11A 121.3 . . ?
C10 C11 H11A 121.3 . . ?
C11 C12 C13 119.95(12) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
N1 C13 O14 112.79(10) . . ?
N1 C13 C12 123.98(12) . . ?
O14 C13 C12 123.22(11) . . ?
C13 O14 C15 116.30(9) . . ?
O14 C15 C16 108.85(10) . . ?
O14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
O14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 C17 109.96(11) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13' N1' C2' 116.12(11) . . ?
N1' C2' C10' 123.36(12) . . ?
N1' C2' C3' 130.14(11) . . ?
C10' C2' C3' 106.47(11) . . ?
C4' C3' C8' 119.30(12) . . ?
C4' C3' C2' 134.86(12) . . ?
C8' C3' C2' 105.84(11) . . ?
C5' C4' C3' 118.95(13) . . ?
C5' C4' H4'A 120.5 . . ?
C3' C4' H4'A 120.5 . . ?
C4' C5' C6' 120.66(15) . . ?
C4' C5' H5'A 119.7 . . ?
C6' C5' H5'A 119.7 . . ?
C7' C6' C5' 121.55(15) . . ?
C7' C6' H6'A 119.2 . . ?
C5' C6' H6'A 119.2 . . ?
C6' C7' C8' 117.95(14) . . ?
C6' C7' H7'A 121.0 . . ?
C8' C7' H7'A 121.0 . . ?
N9' C8' C7' 128.77(13) . . ?
N9' C8' C3' 109.68(12) . . ?
C7' C8' C3' 121.54(13) . . ?
C10' N9' C8' 108.47(11) . . ?
C10' N9' H9'A 125.8 . . ?
C8' N9' H9'A 125.8 . . ?
N9' C10' C11' 131.04(12) . . ?
N9' C10' C2' 109.50(11) . . ?
C11' C10' C2' 119.46(12) . . ?
C10' C11' C12' 117.37(12) . . ?
C10' C11' H11B 121.3 . . ?
C12' C11' H11B 121.3 . . ?
C11' C12' C13' 119.88(12) . . ?
C11' C12' H12B 120.1 . . ?
C13' C12' H12B 120.1 . . ?
N1' C13' O14' 113.25(11) . . ?
N1' C13' C12' 123.79(12) . . ?
O14' C13' C12' 122.96(12) . . ?
C13' O14' C15' 116.60(11) . . ?
O14' C15' C16' 109.18(12) . . ?
O14' C15' H15C 109.8 . . ?
C16' C15' H15C 109.8 . . ?
O14' C15' H15D 109.8 . . ?
C16' C15' H15D 109.8 . . ?
H15C C15' H15D 108.3 . . ?
C15' C16' C17' 114.95(17) . . ?
C15' C16' H16C 108.5 . . ?
C17' C16' H16C 108.5 . . ?
C15' C16' H16D 108.5 . . ?
C17' C16' H16D 108.5 . . ?
H16C C16' H16D 107.5 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C2 C10 0.38(19) . . . . ?
C13 N1 C2 C3 -178.95(13) . . . . ?
N1 C2 C3 C4 -1.6(3) . . . . ?
C10 C2 C3 C4 178.95(15) . . . . ?
N1 C2 C3 C8 178.32(13) . . . . ?
C10 C2 C3 C8 -1.09(15) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 179.68(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 N9 177.90(14) . . . . ?
C6 C7 C8 C3 -1.7(2) . . . . ?
C4 C3 C8 N9 -178.04(12) . . . . ?
C2 C3 C8 N9 2.00(15) . . . . ?
C4 C3 C8 C7 1.6(2) . . . . ?
C2 C3 C8 C7 -178.36(13) . . . . ?
C7 C8 N9 C10 178.25(14) . . . . ?
C3 C8 N9 C10 -2.15(15) . . . . ?
C8 N9 C10 C11 -177.89(15) . . . . ?
C8 N9 C10 C2 1.43(15) . . . . ?
N1 C2 C10 N9 -179.63(12) . . . . ?
C3 C2 C10 N9 -0.17(15) . . . . ?
N1 C2 C10 C11 -0.2(2) . . . . ?
C3 C2 C10 C11 179.24(12) . . . . ?
N9 C10 C11 C12 178.97(14) . . . . ?
C2 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C2 N1 C13 O14 178.87(11) . . . . ?
C2 N1 C13 C12 0.0(2) . . . . ?
C11 C12 C13 N1 -0.5(2) . . . . ?
C11 C12 C13 O14 -179.27(12) . . . . ?
N1 C13 O14 C15 177.28(11) . . . . ?
C12 C13 O14 C15 -3.81(19) . . . . ?
C13 O14 C15 C16 177.38(11) . . . . ?
O14 C15 C16 C17 178.25(12) . . . . ?
C13' N1' C2' C10' 0.05(18) . . . . ?
C13' N1' C2' C3' 177.76(13) . . . . ?
N1' C2' C3' C4' 3.3(3) . . . . ?
C10' C2' C3' C4' -178.69(15) . . . . ?
N1' C2' C3' C8' -176.74(13) . . . . ?
C10' C2' C3' C8' 1.26(14) . . . . ?
C8' C3' C4' C5' 1.5(2) . . . . ?
C2' C3' C4' C5' -178.59(16) . . . . ?
C3' C4' C5' C6' 0.3(3) . . . . ?
C4' C5' C6' C7' -0.9(3) . . . . ?
C5' C6' C7' C8' -0.3(3) . . . . ?
C6' C7' C8' N9' -178.70(16) . . . . ?
C6' C7' C8' C3' 2.1(2) . . . . ?
C4' C3' C8' N9' 177.95(12) . . . . ?
C2' C3' C8' N9' -2.01(15) . . . . ?
C4' C3' C8' C7' -2.8(2) . . . . ?
C2' C3' C8' C7' 177.29(14) . . . . ?
C7' C8' N9' C10' -177.24(15) . . . . ?
C3' C8' N9' C10' 2.00(15) . . . . ?
C8' N9' C10' C11' 178.03(13) . . . . ?
C8' N9' C10' C2' -1.16(14) . . . . ?
N1' C2' C10' N9' 178.08(11) . . . . ?
C3' C2' C10' N9' -0.09(14) . . . . ?
N1' C2' C10' C11' -1.22(19) . . . . ?
C3' C2' C10' C11' -179.39(12) . . . . ?
N9' C10' C11' C12' -178.17(13) . . . . ?
C2' C10' C11' C12' 0.95(18) . . . . ?
C10' C11' C12' C13' 0.3(2) . . . . ?
C2' N1' C13' O14' -178.86(11) . . . . ?
C2' N1' C13' C12' 1.34(19) . . . . ?
C11' C12' C13' N1' -1.6(2) . . . . ?
C11' C12' C13' O14' 178.63(13) . . . . ?
N1' C13' O14' C15' 176.30(12) . . . . ?
C12' C13' O14' C15' -3.9(2) . . . . ?
C13' O14' C15' C16' -170.81(14) . . . . ?
O14' C15' C16' C17' -65.09(19) . . . . ?

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
N9 H9A N1' 0.88 2.07 2.9417(15) 169.0 4_655
N9' H9'A N1 0.88 2.07 2.9502(14) 176.9 4_654

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cook141
_database_code_depnum_ccdc_archive 'CCDC 1044936'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C16 H16 N2 O2), C H3 Br'
_chemical_formula_sum            'C65 H67 Br N8 O8'

_chemical_formula_weight         1168.17

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   16.0850(12)
_cell_length_b                   15.4499(15)
_cell_length_c                   25.045(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.694(4)
_cell_angle_gamma                90
_cell_volume                     6094.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7723
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.01

_exptl_crystal_description       prisim
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.277
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_max          0.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    0.735
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.822

##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.7495
_exptl_absorpt_correction_T_max  0.8222

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
# SMART APEX 2 parameters
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30149
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         29.172
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8179
_reflns_number_gt                5960
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1212P)²+11.4547P] 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         8179
_refine_ls_number_parameters     390
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2204
_refine_ls_wR_factor_gt          0.1978
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.006
_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
N1 N -0.12003(11) 0.20342(11) 0.12926(7) 0.0277(4) Uani 1 1 d . . . . .
C2 C -0.19981(13) 0.23015(14) 0.12384(9) 0.0307(4) Uani 1 1 d . . . . .
H2A H -0.2338 0.2078 0.1476 0.037 Uiso 1 1 calc R U . . .
C3 C -0.23475(12) 0.29030(13) 0.08404(8) 0.0260(4) Uani 1 1 d . . . . .
N4 N -0.31387(11) 0.32699(12) 0.07282(7) 0.0300(4) Uani 1 1 d . . . . .
H4A H -0.3552 0.3165 0.0902 0.036 Uiso 1 1 calc R U . . .
C5 C -0.31774(13) 0.38312(13) 0.02979(8) 0.0279(4) Uani 1 1 d . . . . .
C6 C -0.38610(15) 0.43418(15) 0.00397(9) 0.0344(5) Uani 1 1 d . . . . .
H6A H -0.4387 0.4341 0.0157 0.041 Uiso 1 1 calc R U . . .
C7 C -0.37370(17) 0.48448(16) -0.03911(9) 0.0395(5) Uani 1 1 d . . . . .
H7A H -0.4189 0.5200 -0.0572 0.047 Uiso 1 1 calc R U . . .
C8 C -0.29658(17) 0.48514(16) -0.05720(9) 0.0395(5) Uani 1 1 d . . . . .
H8A H -0.2905 0.5208 -0.0871 0.047 Uiso 1 1 calc R U . . .
C9 C -0.22956(15) 0.43426(15) -0.03186(9) 0.0332(5) Uani 1 1 d . . . . .
H9A H -0.1774 0.4343 -0.0442 0.040 Uiso 1 1 calc R U . . .
C10 C -0.23975(13) 0.38276(13) 0.01221(8) 0.0257(4) Uani 1 1 d . . . . .
C11 C -0.18579(13) 0.32299(12) 0.04763(8) 0.0241(4) Uani 1 1 d . . . . .
C12 C -0.10290(13) 0.29451(12) 0.05334(8) 0.0248(4) Uani 1 1 d . . . . .
H12A H -0.0678 0.3145 0.0296 0.030 Uiso 1 1 calc R U . . .
C13 C -0.07260(12) 0.23586(12) 0.09479(8) 0.0245(4) Uani 1 1 d . . . . .
C14 C 0.01619(13) 0.20368(12) 0.10508(8) 0.0257(4) Uani 1 1 d . . . . .
O14 O 0.04230(9) 0.14438(9) 0.13549(7) 0.0324(3) Uani 1 1 d . . . . .
O15 O 0.06299(9) 0.25036(10) 0.07716(6) 0.0331(3) Uani 1 1 d . . . . .
C16 C 0.15438(14) 0.23423(15) 0.08015(9) 0.0335(5) Uani 1 1 d . . . . .
C17 C 0.17587(18) 0.3022(2) 0.04129(13) 0.0543(7) Uani 1 1 d . . . . .
H17A H 0.1618 0.3598 0.0534 0.081 Uiso 1 1 calc R U . . .
H17B H 0.1430 0.2913 0.0045 0.081 Uiso 1 1 calc R U . . .
H17C H 0.2366 0.2996 0.0409 0.081 Uiso 1 1 calc R U . . .
C18 C 0.20271(16) 0.2512(2) 0.13716(12) 0.0496(7) Uani 1 1 d . . . . .
H18A H 0.1838 0.2109 0.1624 0.074 Uiso 1 1 calc R U . . .
H18B H 0.1923 0.3108 0.1476 0.074 Uiso 1 1 calc R U . . .
H18C H 0.2636 0.2431 0.1386 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1673(2) 0.1438(2) 0.06073(15) 0.0682(8) Uani 1 1 d . . . . .
H19A H 0.1553 0.1018 0.0875 0.102 Uiso 1 1 calc R U . . .
H19B H 0.2262 0.1371 0.0565 0.102 Uiso 1 1 calc R U . . .
H19C H 0.1288 0.1338 0.0256 0.102 Uiso 1 1 calc R U . . .
N1' N -0.04562(11) -0.15490(11) 0.37005(7) 0.0266(4) Uani 1 1 d . . . . .
C2' C -0.02725(12) -0.07371(13) 0.35881(8) 0.0260(4) Uani 1 1 d . . . . .
H2'A H -0.0571 -0.0272 0.3712 0.031 Uiso 1 1 calc R U . . .
C3' C 0.03531(12) -0.05615(12) 0.32907(8) 0.0233(4) Uani 1 1 d . . . . .
N4' N 0.06538(11) 0.02165(10) 0.31447(7) 0.0269(4) Uani 1 1 d . . . . .
H4'A H 0.0486 0.0731 0.3230 0.032 Uiso 1 1 calc R U . . .
C5' C 0.12659(13) 0.00538(13) 0.28403(8) 0.0259(4) Uani 1 1 d . . . . .
C6' C 0.17283(15) 0.06424(14) 0.25920(9) 0.0338(5) Uani 1 1 d . . . . .
H6'A H 0.1667 0.1249 0.2631 0.041 Uiso 1 1 calc R U . . .
C7' C 0.22756(15) 0.03063(15) 0.22894(10) 0.0374(5) Uani 1 1 d . . . . .
H7'A H 0.2599 0.0692 0.2118 0.045 Uiso 1 1 calc R U . . .
C8' C 0.23725(14) -0.05968(15) 0.22252(9) 0.0344(5) Uani 1 1 d . . . . .
H8'A H 0.2752 -0.0806 0.2009 0.041 Uiso 1 1 calc R U . . .
C9' C 0.19176(13) -0.11741(14) 0.24752(8) 0.0294(4) Uani 1 1 d . . . . .
H9'A H 0.1984 -0.1780 0.2436 0.035 Uiso 1 1 calc R U . . .
C10' C 0.13566(12) -0.08499(12) 0.27878(8) 0.0240(4) Uani 1 1 d . . . . .
C11' C 0.07779(12) -0.12461(12) 0.30835(8) 0.0226(4) Uani 1 1 d . . . . .
C12' C 0.05734(12) -0.20929(12) 0.32024(8) 0.0243(4) Uani 1 1 d . . . . .
H12B H 0.0842 -0.2574 0.3072 0.029 Uiso 1 1 calc R U . . .
C13' C -0.00332(12) -0.22081(12) 0.35171(8) 0.0250(4) Uani 1 1 d . . . . .
C14' C -0.02895(13) -0.30856(13) 0.36866(9) 0.0290(4) Uani 1 1 d . . . . .
O14' O -0.08624(11) -0.31991(10) 0.39196(8) 0.0446(4) Uani 1 1 d . . . . .
O15' O 0.02202(10) -0.37054(9) 0.35568(6) 0.0310(3) Uani 1 1 d . . . . .
C16' C 0.01099(15) -0.46190(13) 0.37032(9) 0.0323(5) Uani 1 1 d . . . . .
C17' C -0.0764(2) -0.49385(18) 0.34370(14) 0.0565(8) Uani 1 1 d . . . . .
H17D H -0.1193 -0.4631 0.3592 0.085 Uiso 1 1 calc R U . . .
H17E H -0.0804 -0.5561 0.3503 0.085 Uiso 1 1 calc R U . . .
H17F H -0.0862 -0.4830 0.3044 0.085 Uiso 1 1 calc R U . . .
C18' C 0.07930(19) -0.50730(15) 0.34678(11) 0.0460(6) Uani 1 1 d . . . . .
H18D H 0.1350 -0.4832 0.3632 0.069 Uiso 1 1 calc R U . . .
H18E H 0.0683 -0.4987 0.3072 0.069 Uiso 1 1 calc R U . . .
H18F H 0.0786 -0.5694 0.3548 0.069 Uiso 1 1 calc R U . . .
C19' C 0.0286(2) -0.47065(18) 0.43184(11) 0.0521(7) Uani 1 1 d . . . . .
H19D H 0.0851 -0.4474 0.4472 0.078 Uiso 1 1 calc R U . . .
H19E H 0.0264 -0.5319 0.4417 0.078 Uiso 1 1 calc R U . . .
H19F H -0.0143 -0.4384 0.4464 0.078 Uiso 1 1 calc R U . . .
Br1S Br 0.08645(4) 0.30756(4) 0.24099(3) 0.05724(16) Uani 0.5 1 d . . P . .
C1S C 0.0000 0.24257(8) 0.2500 0.0297(6) Uani 1 2 d DS T P . .
H1SA H -0.0020(3) 0.21596(15) 0.28435(5) 0.036 Uiso 0.5 1 d D U P . .
H1SB H -0.0310(2) 0.20738(12) 0.22112(7) 0.036 Uiso 0.5 1 d D U P . .
H1SC H -0.0260(2) 0.29864(8) 0.24856(14) 0.036 Uiso 0.5 1 d D U P . .


_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
N1 C2 1.329(3) . ?
N1 C13 1.359(3) . ?
C2 C3 1.395(3) . ?
C2 H2A 0.9500 . ?
C3 N4 1.369(3) . ?
C3 C11 1.413(3) . ?
N4 C5 1.375(3) . ?
N4 H4A 0.8800 . ?
C5 C6 1.400(3) . ?
C5 C10 1.411(3) . ?
C6 C7 1.377(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.404(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.443(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.390(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.485(3) . ?
C14 O14 1.211(2) . ?
C14 O15 1.338(2) . ?
O15 C16 1.478(3) . ?
C16 C18 1.504(4) . ?
C16 C19 1.507(4) . ?
C16 C17 1.519(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1' C2' 1.332(3) . ?
N1' C13' 1.356(2) . ?
C2' C3' 1.395(3) . ?
C2' H2'A 0.9500 . ?
C3' N4' 1.373(3) . ?
C3' C11' 1.414(3) . ?
N4' C5' 1.385(3) . ?
N4' H4'A 0.8800 . ?
C5' C6' 1.398(3) . ?
C5' C10' 1.413(3) . ?
C6' C7' 1.375(3) . ?
C6' H6'A 0.9500 . ?
C7' C8' 1.417(3) . ?
C7' H7'A 0.9500 . ?
C8' C9' 1.382(3) . ?
C8' H8'A 0.9500 . ?
C9' C10' 1.401(3) . ?
C9' H9'A 0.9500 . ?
C10' C11' 1.438(3) . ?
C11' C12' 1.396(3) . ?
C12' C13' 1.384(3) . ?
C12' H12B 0.9500 . ?
C13' C14' 1.503(3) . ?
C14' O14' 1.199(3) . ?
C14' O15' 1.343(2) . ?
O15' C16' 1.478(2) . ?
C16' C17' 1.512(4) . ?
C16' C19' 1.515(3) . ?
C16' C18' 1.520(3) . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
Br1S C1S 1.7663(9) . ?
Br1S H1SC 1.862(4) . ?
C1S Br1S 1.7663(9) 2 ?
C1S H1SA 0.9598(10) . ?
C1S H1SB 0.9598(9) . ?
C1S H1SC 0.9597(9) . ?

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 N1 C13 118.40(17) . . ?
N1 C2 C3 121.39(19) . . ?
N1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
N4 C3 C2 130.20(19) . . ?
N4 C3 C11 109.63(17) . . ?
C2 C3 C11 120.17(18) . . ?
C3 N4 C5 108.33(17) . . ?
C3 N4 H4A 125.8 . . ?
C5 N4 H4A 125.8 . . ?
N4 C5 C6 128.6(2) . . ?
N4 C5 C10 109.89(18) . . ?
C6 C5 C10 121.5(2) . . ?
C7 C6 C5 117.1(2) . . ?
C7 C6 H6A 121.5 . . ?
C5 C6 H6A 121.5 . . ?
C6 C7 C8 122.3(2) . . ?
C6 C7 H7A 118.8 . . ?
C8 C7 H7A 118.8 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C9 C10 C5 119.89(19) . . ?
C9 C10 C11 134.3(2) . . ?
C5 C10 C11 105.83(17) . . ?
C12 C11 C3 118.10(18) . . ?
C12 C11 C10 135.58(18) . . ?
C3 C11 C10 106.32(17) . . ?
C11 C12 C13 117.98(18) . . ?
C11 C12 H12A 121.0 . . ?
C13 C12 H12A 121.0 . . ?
N1 C13 C12 123.93(18) . . ?
N1 C13 C14 114.24(17) . . ?
C12 C13 C14 121.83(18) . . ?
O14 C14 O15 125.21(19) . . ?
O14 C14 C13 124.15(18) . . ?
O15 C14 C13 110.63(17) . . ?
C14 O15 C16 122.82(17) . . ?
O15 C16 C18 109.64(18) . . ?
O15 C16 C19 109.9(2) . . ?
C18 C16 C19 112.9(2) . . ?
O15 C16 C17 101.77(18) . . ?
C18 C16 C17 110.3(2) . . ?
C19 C16 C17 111.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2' N1' C13' 119.19(18) . . ?
N1' C2' C3' 120.74(17) . . ?
N1' C2' H2'A 119.6 . . ?
C3' C2' H2'A 119.6 . . ?
N4' C3' C2' 130.09(17) . . ?
N4' C3' C11' 109.56(17) . . ?
C2' C3' C11' 120.35(18) . . ?
C3' N4' C5' 108.41(16) . . ?
C3' N4' H4'A 125.8 . . ?
C5' N4' H4'A 125.8 . . ?
N4' C5' C6' 128.94(19) . . ?
N4' C5' C10' 109.21(17) . . ?
C6' C5' C10' 121.81(19) . . ?
C7' C6' C5' 117.2(2) . . ?
C7' C6' H6'A 121.4 . . ?
C5' C6' H6'A 121.4 . . ?
C6' C7' C8' 122.1(2) . . ?
C6' C7' H7'A 118.9 . . ?
C8' C7' H7'A 118.9 . . ?
C9' C8' C7' 120.3(2) . . ?
C9' C8' H8'A 119.9 . . ?
C7' C8' H8'A 119.9 . . ?
C8' C9' C10' 118.8(2) . . ?
C8' C9' H9'A 120.6 . . ?
C10' C9' H9'A 120.6 . . ?
C9' C10' C5' 119.71(19) . . ?
C9' C10' C11' 133.83(18) . . ?
C5' C10' C11' 106.42(17) . . ?
C12' C11' C3' 118.08(18) . . ?
C12' C11' C10' 135.54(18) . . ?
C3' C11' C10' 106.38(16) . . ?
C13' C12' C11' 117.75(17) . . ?
C13' C12' H12B 121.1 . . ?
C11' C12' H12B 121.1 . . ?
N1' C13' C12' 123.82(18) . . ?
N1' C13' C14' 113.36(17) . . ?
C12' C13' C14' 122.82(17) . . ?
O14' C14' O15' 125.49(19) . . ?
O14' C14' C13' 123.44(18) . . ?
O15' C14' C13' 111.04(17) . . ?
C14' O15' C16' 120.74(16) . . ?
O15' C16' C17' 110.49(19) . . ?
O15' C16' C19' 109.30(18) . . ?
C17' C16' C19' 112.6(2) . . ?
O15' C16' C18' 102.24(17) . . ?
C17' C16' C18' 111.0(2) . . ?
C19' C16' C18' 110.6(2) . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C16' C18' H18D 109.5 . . ?
C16' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C16' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C16' C19' H19D 109.5 . . ?
C16' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C16' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C1S Br1S H1SC 30.53(4) . . ?
Br1S C1S Br1S 110.71(8) . 2 ?
Br1S C1S H1SA 121.9(3) . . ?
Br1S C1S H1SA 87.7(3) 2 . ?
Br1S C1S H1SB 121.9(2) . . ?
Br1S C1S H1SB 96.7(2) 2 . ?
H1SA C1S H1SB 109.05(19) . . ?
Br1S C1S H1SC 80.3(2) . . ?
Br1S C1S H1SC 31.0(2) 2 . ?
H1SA C1S H1SC 109.1(2) . . ?
H1SB C1S H1SC 109.07(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C2 C3 -0.3(3) . . . . ?
N1 C2 C3 N4 -178.3(2) . . . . ?
N1 C2 C3 C11 1.3(3) . . . . ?
C2 C3 N4 C5 179.6(2) . . . . ?
C11 C3 N4 C5 0.0(2) . . . . ?
C3 N4 C5 C6 179.2(2) . . . . ?
C3 N4 C5 C10 0.4(2) . . . . ?
N4 C5 C6 C7 -179.1(2) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C8 C9 C10 C11 179.8(2) . . . . ?
N4 C5 C10 C9 179.01(18) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
N4 C5 C10 C11 -0.6(2) . . . . ?
C6 C5 C10 C11 -179.54(18) . . . . ?
N4 C3 C11 C12 178.80(17) . . . . ?
C2 C3 C11 C12 -0.9(3) . . . . ?
N4 C3 C11 C10 -0.4(2) . . . . ?
C2 C3 C11 C10 179.97(18) . . . . ?
C9 C10 C11 C12 2.1(4) . . . . ?
C5 C10 C11 C12 -178.4(2) . . . . ?
C9 C10 C11 C3 -179.0(2) . . . . ?
C5 C10 C11 C3 0.6(2) . . . . ?
C3 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 178.4(2) . . . . ?
C2 N1 C13 C12 -1.1(3) . . . . ?
C2 N1 C13 C14 178.52(18) . . . . ?
C11 C12 C13 N1 1.5(3) . . . . ?
C11 C12 C13 C14 -178.16(17) . . . . ?
N1 C13 C14 O14 10.7(3) . . . . ?
C12 C13 C14 O14 -169.61(19) . . . . ?
N1 C13 C14 O15 -167.94(16) . . . . ?
C12 C13 C14 O15 11.7(3) . . . . ?
O14 C14 O15 C16 0.2(3) . . . . ?
C13 C14 O15 C16 178.89(17) . . . . ?
C14 O15 C16 C18 -64.0(3) . . . . ?
C14 O15 C16 C19 60.7(3) . . . . ?
C14 O15 C16 C17 179.2(2) . . . . ?
C13' N1' C2' C3' -0.7(3) . . . . ?
N1' C2' C3' N4' -178.04(18) . . . . ?
N1' C2' C3' C11' 2.7(3) . . . . ?
C2' C3' N4' C5' -178.83(19) . . . . ?
C11' C3' N4' C5' 0.5(2) . . . . ?
C3' N4' C5' C6' 178.0(2) . . . . ?
C3' N4' C5' C10' 0.3(2) . . . . ?
N4' C5' C6' C7' -177.1(2) . . . . ?
C10' C5' C6' C7' 0.4(3) . . . . ?
C5' C6' C7' C8' 0.3(3) . . . . ?
C6' C7' C8' C9' -0.8(3) . . . . ?
C7' C8' C9' C10' 0.5(3) . . . . ?
C8' C9' C10' C5' 0.1(3) . . . . ?
C8' C9' C10' C11' 177.8(2) . . . . ?
N4' C5' C10' C9' 177.31(17) . . . . ?
C6' C5' C10' C9' -0.6(3) . . . . ?
N4' C5' C10' C11' -0.9(2) . . . . ?
C6' C5' C10' C11' -178.83(18) . . . . ?
N4' C3' C11' C12' 178.35(16) . . . . ?
C2' C3' C11' C12' -2.3(3) . . . . ?
N4' C3' C11' C10' -1.0(2) . . . . ?
C2' C3' C11' C10' 178.34(17) . . . . ?
C9' C10' C11' C12' 4.1(4) . . . . ?
C5' C10' C11' C12' -178.0(2) . . . . ?
C9' C10' C11' C3' -176.7(2) . . . . ?
C5' C10' C11' C3' 1.2(2) . . . . ?
C3' C11' C12' C13' -0.1(3) . . . . ?
C10' C11' C12' C13' 179.1(2) . . . . ?
C2' N1' C13' C12' -1.8(3) . . . . ?
C2' N1' C13' C14' 178.49(17) . . . . ?
C11' C12' C13' N1' 2.1(3) . . . . ?
C11' C12' C13' C14' -178.15(18) . . . . ?
N1' C13' C14' O14' 6.2(3) . . . . ?
C12' C13' C14' O14' -173.5(2) . . . . ?
N1' C13' C14' O15' -171.99(17) . . . . ?
C12' C13' C14' O15' 8.3(3) . . . . ?
O14' C14' O15' C16' -0.5(3) . . . . ?
C13' C14' O15' C16' 177.66(17) . . . . ?
C14' O15' C16' C17' 60.4(3) . . . . ?
C14' O15' C16' C19' -64.1(3) . . . . ?
C14' O15' C16' C18' 178.60(19) . . . . ?

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
N4 H4A N1' 0.88 2.09 2.923(3) 157.1 4_455
N4 H4A O14' 0.88 2.39 3.014(2) 128.5 4_455
C18 H18A O14 0.98 2.46 3.056(3) 118.6 .
C19 H19A O14 0.98 2.46 3.012(4) 115.1 .
N4' H4'A N1 0.88 2.50 3.185(2) 135.3 2
N4' H4'A O14 0.88 2.25 3.008(2) 144.6 2
C17' H17D O14' 0.98 2.38 2.964(3) 117.4 .
C19' H19F O14' 0.98 2.43 3.014(3) 117.7 .
C1S H1SA N1 0.9598(10) 2.617(4) 3.2970(18) 128.1(4) 2
C1S H1SA O14 0.9598(10) 2.490(2) 3.4322(17) 166.9(4) 2
C1S H1SB N1 0.9598(9) 2.452(2) 3.2970(18) 146.79(18) .
C1S H1SC Br1S 0.9597(9) 1.065(3) 1.7663(9) 121.4(3) 2

_refine_diff_density_max         0.484
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.077

