# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Tom McCabe'
_publ_contact_author_email       TMCCABE@tcd.ie
loop_
_publ_author_name
T.Gunnlaugsson
C.Lincheneau
T.McCabe
J.Leonard

data_jpl030dm
_database_code_depnum_ccdc_archive 'CCDC 814612'
#TrackingRef 'jpl030dm.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H29 N5 O6'
_chemical_formula_weight         567.59

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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.3915(6)
_cell_length_b                   12.7730(8)
_cell_length_c                   23.7777(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2852.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7885
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      571(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33990
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.33
_reflns_number_total             7093
_reflns_number_gt                4095
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Smart'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  'Shelxtl and Mercury'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       ?
_chemical_absolute_configuration ad
loop_
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_number_reflns         7093
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   0.774
_refine_ls_restrained_S_all      0.774
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002

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
O6 O 0.68240(13) 0.65149(10) 0.23875(5) 0.0606(3) Uani 1 1 d . . .
N1 N 0.44453(12) 0.84960(9) 0.07728(5) 0.0347(3) Uani 1 1 d . . .
O2 O 0.19316(11) 0.80645(8) -0.03180(4) 0.0503(3) Uani 1 1 d . . .
N3 N 0.68034(12) 0.80288(9) 0.14165(5) 0.0402(3) Uani 1 1 d . . .
H3 H 0.6503 0.7615 0.1157 0.048 Uiso 1 1 calc R . .
O1 O 0.64857(12) 0.95486(8) 0.18804(4) 0.0528(3) Uani 1 1 d . . .
C17 C 0.34706(16) 0.87680(11) 0.03877(6) 0.0361(4) Uani 1 1 d . . .
C12 C 0.61583(15) 0.89494(12) 0.14975(6) 0.0383(4) Uani 1 1 d . . .
C13 C 0.50376(15) 0.92582(11) 0.10758(6) 0.0359(4) Uani 1 1 d . . .
O8 O 0.32754(14) 0.47076(8) -0.07035(5) 0.0641(3) Uani 1 1 d . . .
C10 C 0.80093(15) 0.77202(12) 0.17635(6) 0.0407(4) Uani 1 1 d . . .
H10 H 0.8594 0.8342 0.1833 0.049 Uiso 1 1 calc R . .
C7 C 1.01931(16) 0.65965(12) 0.18256(6) 0.0443(4) Uani 1 1 d . . .
C18 C 0.28047(17) 0.79006(12) 0.00567(6) 0.0418(4) Uani 1 1 d . . .
N2 N 0.32452(16) 0.69558(10) 0.02094(6) 0.0636(4) Uani 1 1 d . . .
H50 H 0.3882 0.6921 0.0469 0.076 Uiso 1 1 calc R . .
C16 C 0.30825(18) 0.97950(12) 0.02869(7) 0.0490(4) Uani 1 1 d . . .
H16 H 0.2408 0.9958 0.0014 0.059 Uiso 1 1 calc R . .
C4 C 1.13150(16) 0.72673(12) 0.20137(6) 0.0422(4) Uani 1 1 d . . .
N4 N 1.16767(15) 0.56721(11) 0.23699(5) 0.0560(4) Uani 1 1 d . . .
H4 H 1.2043 0.5153 0.2549 0.067 Uiso 1 1 calc R . .
O5 O 0.48060(15) 0.60380(10) -0.06271(6) 0.0782(4) Uani 1 1 d . . .
C20 C 0.3747(2) 0.55992(13) -0.04774(7) 0.0530(4) Uani 1 1 d . . .
C9 C 0.89358(16) 0.69033(12) 0.14670(6) 0.0455(4) Uani 1 1 d . . .
H9A H 0.8368 0.6287 0.1386 0.055 Uiso 1 1 calc R . .
H9B H 0.9273 0.7186 0.1113 0.055 Uiso 1 1 calc R . .
C23 C 0.37787(18) 0.50118(13) 0.08070(7) 0.0480(4) Uani 1 1 d . . .
C3 C 1.22115(17) 0.66668(14) 0.23551(6) 0.0457(4) Uani 1 1 d . . .
C19 C 0.27427(19) 0.59823(12) -0.00241(7) 0.0539(5) Uani 1 1 d . . .
H19 H 0.1821 0.6121 -0.0203 0.065 Uiso 1 1 calc R . .
C11 C 0.75123(17) 0.72980(14) 0.23260(7) 0.0454(4) Uani 1 1 d . . .
O7 O 0.79610(14) 0.79000(10) 0.27459(5) 0.0697(4) Uani 1 1 d . . .
C8 C 1.04626(18) 0.56400(14) 0.20526(7) 0.0512(4) Uani 1 1 d . . .
H8 H 0.9902 0.5048 0.2000 0.061 Uiso 1 1 calc R . .
N5 N 0.54657(18) 0.52626(12) 0.14599(6) 0.0650(4) Uani 1 1 d . . .
H26 H 0.5902 0.5520 0.1746 0.078 Uiso 1 1 calc R . .
C2 C 1.34285(18) 0.70743(15) 0.26019(7) 0.0574(5) Uani 1 1 d . . .
H2 H 1.4022 0.6659 0.2822 0.069 Uiso 1 1 calc R . .
C24 C 0.49082(19) 0.42801(12) 0.07130(6) 0.0474(4) Uani 1 1 d . . .
C15 C 0.37232(18) 1.05741(13) 0.06021(7) 0.0572(5) Uani 1 1 d . . .
H15 H 0.3492 1.1273 0.0542 0.069 Uiso 1 1 calc R . .
C5 C 1.16521(19) 0.83235(13) 0.19257(7) 0.0545(4) Uani 1 1 d . . .
H5 H 1.1076 0.8742 0.1700 0.065 Uiso 1 1 calc R . .
C26 C 0.4171(2) 0.55828(14) 0.12617(7) 0.0585(5) Uani 1 1 d . . .
H5A H 0.3632 0.6120 0.1418 0.070 Uiso 1 1 calc R . .
C14 C 0.47052(17) 1.03029(12) 0.10047(7) 0.0493(4) Uani 1 1 d . . .
H14 H 0.5138 1.0813 0.1225 0.059 Uiso 1 1 calc R . .
C27 C 0.5139(2) 0.34766(13) 0.03291(7) 0.0614(5) Uani 1 1 d . . .
H27 H 0.4458 0.3323 0.0057 0.074 Uiso 1 1 calc R . .
C22 C 0.2488(2) 0.51880(13) 0.04506(7) 0.0591(5) Uani 1 1 d . . .
H22A H 0.1717 0.5437 0.0687 0.071 Uiso 1 1 calc R . .
H22B H 0.2194 0.4526 0.0287 0.071 Uiso 1 1 calc R . .
C25 C 0.5952(2) 0.44657(14) 0.11280(7) 0.0561(5) Uani 1 1 d . . .
C1 C 1.37257(19) 0.81066(17) 0.25110(7) 0.0637(5) Uani 1 1 d . . .
H51 H 1.4532 0.8399 0.2675 0.076 Uiso 1 1 calc R . .
C6 C 1.28502(19) 0.87334(14) 0.21780(8) 0.0627(5) Uani 1 1 d . . .
H6 H 1.3077 0.9435 0.2126 0.075 Uiso 1 1 calc R . .
C29 C 0.7401(3) 0.31319(17) 0.07574(10) 0.0901(7) Uani 1 1 d . . .
H29 H 0.8241 0.2746 0.0760 0.108 Uiso 1 1 calc R . .
C33 C 0.4139(2) 0.42991(16) -0.11568(8) 0.0831(6) Uani 1 1 d . . .
H33A H 0.4999 0.4007 -0.1006 0.125 Uiso 1 1 calc R . .
H33B H 0.4372 0.4855 -0.1413 0.125 Uiso 1 1 calc R . .
H33C H 0.3619 0.3765 -0.1353 0.125 Uiso 1 1 calc R . .
C28 C 0.6381(3) 0.29114(16) 0.03551(9) 0.0810(6) Uani 1 1 d . . .
H28 H 0.6537 0.2373 0.0099 0.097 Uiso 1 1 calc R . .
C32 C 0.7555(3) 0.75712(19) 0.33092(7) 0.1061(8) Uani 1 1 d . . .
H32A H 0.7852 0.6861 0.3369 0.159 Uiso 1 1 calc R . .
H32B H 0.6540 0.7618 0.3349 0.159 Uiso 1 1 calc R . .
H32C H 0.8005 0.8017 0.3581 0.159 Uiso 1 1 calc R . .
C30 C 0.7215(2) 0.39000(16) 0.11512(8) 0.0757(6) Uani 1 1 d . . .
H30 H 0.7903 0.4038 0.1423 0.091 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0553(8) 0.0684(8) 0.0582(7) 0.0062(7) -0.0016(6) -0.0060(7)
N1 0.0307(7) 0.0393(7) 0.0341(7) -0.0037(6) -0.0016(6) 0.0020(6)
O2 0.0482(7) 0.0562(7) 0.0464(6) -0.0068(6) -0.0160(6) 0.0048(6)
N3 0.0385(7) 0.0398(7) 0.0422(7) -0.0067(6) -0.0125(6) 0.0056(6)
O1 0.0535(7) 0.0514(7) 0.0534(6) -0.0171(6) -0.0180(6) 0.0046(6)
C17 0.0317(8) 0.0413(9) 0.0355(8) -0.0020(7) 0.0002(7) 0.0030(7)
C12 0.0348(9) 0.0403(9) 0.0399(9) -0.0019(8) -0.0012(8) -0.0006(8)
C13 0.0312(8) 0.0383(9) 0.0383(8) -0.0044(7) -0.0013(7) 0.0032(7)
O8 0.0822(9) 0.0481(7) 0.0620(7) -0.0106(6) -0.0001(7) -0.0087(7)
C10 0.0363(9) 0.0441(9) 0.0417(9) -0.0012(7) -0.0091(8) 0.0029(8)
C7 0.0392(9) 0.0514(10) 0.0422(9) 0.0048(8) -0.0021(8) 0.0119(8)
C18 0.0389(9) 0.0470(10) 0.0394(9) -0.0061(8) -0.0018(8) 0.0049(8)
N2 0.0713(10) 0.0405(8) 0.0790(10) -0.0102(7) -0.0427(9) 0.0045(8)
C16 0.0484(11) 0.0471(10) 0.0515(10) 0.0042(8) -0.0121(9) 0.0075(8)
C4 0.0363(9) 0.0504(10) 0.0397(9) 0.0013(8) 0.0034(8) 0.0095(8)
N4 0.0534(9) 0.0593(9) 0.0552(9) 0.0174(7) -0.0086(8) 0.0133(8)
O5 0.0741(9) 0.0765(9) 0.0839(9) 0.0080(8) -0.0071(8) -0.0247(8)
C20 0.0602(12) 0.0431(10) 0.0556(11) 0.0074(9) -0.0196(10) -0.0015(10)
C9 0.0410(9) 0.0509(10) 0.0446(9) 0.0010(8) -0.0048(8) 0.0079(8)
C23 0.0556(11) 0.0450(10) 0.0433(10) -0.0017(8) 0.0081(9) -0.0045(9)
C3 0.0391(10) 0.0610(11) 0.0369(8) 0.0037(8) 0.0015(8) 0.0081(9)
C19 0.0522(11) 0.0424(10) 0.0670(12) -0.0079(9) -0.0181(10) -0.0005(9)
C11 0.0377(10) 0.0560(11) 0.0425(10) -0.0033(9) -0.0081(8) 0.0151(9)
O7 0.0863(9) 0.0813(8) 0.0415(6) -0.0068(7) -0.0129(7) 0.0000(8)
C8 0.0433(10) 0.0557(11) 0.0547(11) 0.0045(9) -0.0055(8) 0.0031(9)
N5 0.0833(12) 0.0691(10) 0.0426(9) -0.0030(8) -0.0073(8) -0.0026(9)
C2 0.0441(10) 0.0807(14) 0.0474(10) 0.0069(10) -0.0043(9) 0.0097(10)
C24 0.0635(11) 0.0391(9) 0.0398(9) 0.0062(8) 0.0077(9) -0.0048(9)
C15 0.0632(12) 0.0348(9) 0.0735(12) -0.0004(9) -0.0210(11) 0.0074(9)
C5 0.0440(10) 0.0608(11) 0.0589(10) 0.0079(9) 0.0023(9) 0.0091(10)
C26 0.0673(13) 0.0602(12) 0.0481(10) -0.0025(10) 0.0102(10) 0.0040(11)
C14 0.0513(11) 0.0395(10) 0.0572(11) -0.0092(8) -0.0148(9) 0.0008(8)
C27 0.0838(14) 0.0403(10) 0.0602(11) 0.0026(9) 0.0103(11) -0.0041(10)
C22 0.0523(11) 0.0580(11) 0.0669(12) -0.0175(10) 0.0018(10) -0.0060(9)
C25 0.0702(14) 0.0504(11) 0.0476(11) 0.0086(9) 0.0045(10) 0.0000(10)
C1 0.0445(11) 0.0883(15) 0.0581(11) -0.0077(11) -0.0012(9) -0.0049(11)
C6 0.0534(12) 0.0613(11) 0.0733(12) -0.0017(10) 0.0054(11) -0.0025(10)
C29 0.0976(18) 0.0734(16) 0.0994(17) 0.0252(14) 0.0156(16) 0.0340(14)
C33 0.1174(18) 0.0651(12) 0.0667(13) -0.0025(11) 0.0132(13) 0.0013(13)
C28 0.1114(19) 0.0493(12) 0.0823(15) 0.0007(11) 0.0209(15) 0.0166(13)
C32 0.139(2) 0.141(2) 0.0387(11) -0.0032(12) -0.0061(14) -0.0024(19)
C30 0.0766(15) 0.0775(14) 0.0731(14) 0.0185(12) -0.0081(12) 0.0095(13)

_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
O6 C11 1.1999(18) . ?
N1 C13 1.3328(17) . ?
N1 C17 1.3406(17) . ?
O2 C18 1.2288(16) . ?
N3 C12 1.3367(17) . ?
N3 C10 1.4556(17) . ?
O1 C12 1.2285(16) . ?
C17 C16 1.3824(19) . ?
C17 C18 1.496(2) . ?
C12 C13 1.5062(19) . ?
C13 C14 1.381(2) . ?
O8 C20 1.3352(19) . ?
O8 C33 1.446(2) . ?
C10 C11 1.516(2) . ?
C10 C9 1.531(2) . ?
C7 C8 1.359(2) . ?
C7 C4 1.430(2) . ?
C7 C9 1.5083(19) . ?
C18 N2 1.3264(18) . ?
N2 C19 1.4413(18) . ?
C16 C15 1.384(2) . ?
C4 C3 1.399(2) . ?
C4 C5 1.401(2) . ?
N4 C3 1.367(2) . ?
N4 C8 1.368(2) . ?
O5 C20 1.196(2) . ?
C20 C19 1.514(2) . ?
C23 C26 1.355(2) . ?
C23 C24 1.431(2) . ?
C23 C22 1.496(2) . ?
C3 C2 1.386(2) . ?
C19 C22 1.536(2) . ?
C11 O7 1.3288(18) . ?
O7 C32 1.455(2) . ?
N5 C25 1.367(2) . ?
N5 C26 1.367(2) . ?
C2 C1 1.365(2) . ?
C24 C27 1.391(2) . ?
C24 C25 1.411(2) . ?
C15 C14 1.374(2) . ?
C5 C6 1.378(2) . ?
C27 C28 1.373(3) . ?
C25 C30 1.390(2) . ?
C1 C6 1.394(2) . ?
C29 C30 1.368(3) . ?
C29 C28 1.383(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C17 117.71(12) . . ?
C12 N3 C10 120.61(12) . . ?
N1 C17 C16 122.98(14) . . ?
N1 C17 C18 116.93(12) . . ?
C16 C17 C18 120.09(13) . . ?
O1 C12 N3 122.78(14) . . ?
O1 C12 C13 120.34(13) . . ?
N3 C12 C13 116.82(13) . . ?
N1 C13 C14 123.04(14) . . ?
N1 C13 C12 117.40(13) . . ?
C14 C13 C12 119.52(13) . . ?
C20 O8 C33 114.95(15) . . ?
N3 C10 C11 110.91(12) . . ?
N3 C10 C9 111.46(11) . . ?
C11 C10 C9 109.81(12) . . ?
C8 C7 C4 106.09(14) . . ?
C8 C7 C9 127.14(15) . . ?
C4 C7 C9 126.73(14) . . ?
O2 C18 N2 124.17(14) . . ?
O2 C18 C17 122.29(14) . . ?
N2 C18 C17 113.54(13) . . ?
C18 N2 C19 125.27(13) . . ?
C15 C16 C17 118.29(15) . . ?
C3 C4 C5 118.59(16) . . ?
C3 C4 C7 107.25(14) . . ?
C5 C4 C7 134.16(15) . . ?
C3 N4 C8 108.65(14) . . ?
O5 C20 O8 123.77(18) . . ?
O5 C20 C19 125.37(16) . . ?
O8 C20 C19 110.84(16) . . ?
C7 C9 C10 111.21(12) . . ?
C26 C23 C24 105.94(16) . . ?
C26 C23 C22 126.23(16) . . ?
C24 C23 C22 127.61(15) . . ?
N4 C3 C2 129.88(16) . . ?
N4 C3 C4 107.68(14) . . ?
C2 C3 C4 122.42(16) . . ?
N2 C19 C20 110.43(15) . . ?
N2 C19 C22 109.75(13) . . ?
C20 C19 C22 114.01(13) . . ?
O6 C11 O7 124.17(16) . . ?
O6 C11 C10 124.76(15) . . ?
O7 C11 C10 111.06(15) . . ?
C11 O7 C32 116.21(15) . . ?
C7 C8 N4 110.33(15) . . ?
C25 N5 C26 108.72(16) . . ?
C1 C2 C3 117.67(16) . . ?
C27 C24 C25 118.35(17) . . ?
C27 C24 C23 134.43(18) . . ?
C25 C24 C23 107.21(14) . . ?
C14 C15 C16 119.21(15) . . ?
C6 C5 C4 119.02(16) . . ?
C23 C26 N5 110.83(17) . . ?
C15 C14 C13 118.75(15) . . ?
C28 C27 C24 119.41(19) . . ?
C23 C22 C19 112.89(14) . . ?
N5 C25 C30 130.48(19) . . ?
N5 C25 C24 107.28(16) . . ?
C30 C25 C24 122.23(17) . . ?
C2 C1 C6 121.60(17) . . ?
C5 C6 C1 120.69(17) . . ?
C30 C29 C28 122.1(2) . . ?
C27 C28 C29 120.8(2) . . ?
C29 C30 C25 117.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.025

# Attachment 'jpl030lm.cif'

data_jpl030lm
_database_code_depnum_ccdc_archive 'CCDC 814613'
#TrackingRef 'jpl030lm.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H27 N5 O6'
_chemical_formula_weight         565.58

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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.3996(6)
_cell_length_b                   12.7720(9)
_cell_length_c                   23.7627(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2852.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8131
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      571(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30360
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5000
_reflns_number_gt                3486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  'Shelxtl and Mercury'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0564P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.0103(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration ad
loop_
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(13)
_refine_ls_number_reflns         5000
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.200
_refine_ls_shift/su_mean         0.057

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
N2 N 1.0548(2) 0.34952(16) 0.07760(9) 0.0355(5) Uani 1 1 d . . .
O6 O 1.3064(2) 0.30600(14) -0.03174(7) 0.0512(5) Uani 1 1 d . . .
N3 N 0.8197(2) 0.30312(16) 0.14209(9) 0.0408(5) Uani 1 1 d . . .
H3 H 0.8499 0.2619 0.1161 0.049 Uiso 1 1 calc R . .
O5 O 0.8515(2) 0.45509(15) 0.18837(8) 0.0532(5) Uani 1 1 d . . .
C13 C 1.1526(3) 0.3766(2) 0.03907(10) 0.0375(6) Uani 1 1 d . . .
O2 O 0.8172(2) 0.15203(18) 0.23906(8) 0.0616(6) Uani 1 1 d . . .
C18 C 0.8835(3) 0.3952(2) 0.15036(11) 0.0393(7) Uani 1 1 d . . .
C22 C 0.4805(3) 0.1595(2) 0.18311(11) 0.0438(7) Uani 1 1 d . . .
O3 O 1.1724(3) -0.02941(15) -0.07063(9) 0.0664(6) Uani 1 1 d . . .
C17 C 0.9959(3) 0.4258(2) 0.10808(10) 0.0369(6) Uani 1 1 d . . .
C14 C 1.1915(3) 0.4789(2) 0.02910(12) 0.0496(8) Uani 1 1 d . . .
H14 H 1.2588 0.4952 0.0018 0.060 Uiso 1 1 calc R . .
C12 C 1.2193(3) 0.2900(2) 0.00573(11) 0.0426(7) Uani 1 1 d . . .
N4 N 0.3322(3) 0.0674(2) 0.23683(10) 0.0563(7) Uani 1 1 d . . .
H4 H 0.2951 0.0153 0.2545 0.068 Uiso 1 1 calc R . .
O4 O 1.0193(3) 0.10365(18) -0.06307(11) 0.0797(7) Uani 1 1 d . . .
N1 N 1.1752(3) 0.19531(18) 0.02110(11) 0.0659(8) Uani 1 1 d . . .
H1 H 1.1115 0.1919 0.0470 0.079 Uiso 1 1 calc R . .
C19 C 0.6986(3) 0.2720(2) 0.17701(10) 0.0415(7) Uani 1 1 d . . .
H19 H 0.6401 0.3341 0.1840 0.050 Uiso 1 1 calc R . .
C11 C 1.1255(4) 0.0597(2) -0.04818(13) 0.0543(8) Uani 1 1 d . . .
C1 C 1.1211(3) 0.0009(2) 0.08190(12) 0.0504(8) Uani 1 1 d . . .
C23 C 0.3689(3) 0.2268(2) 0.20178(11) 0.0430(7) Uani 1 1 d . . .
C21 C 0.6061(3) 0.1902(2) 0.14775(11) 0.0465(7) Uani 1 1 d . . .
H21A H 0.5727 0.2182 0.1122 0.056 Uiso 1 1 calc R . .
H21B H 0.6629 0.1286 0.1398 0.056 Uiso 1 1 calc R . .
C3 C 1.0081(3) -0.0722(2) 0.07197(12) 0.0493(7) Uani 1 1 d . . .
C10 C 1.2255(3) 0.0980(2) -0.00213(13) 0.0565(9) Uani 1 1 d . . .
H10 H 1.3179 0.1119 -0.0197 0.068 Uiso 1 1 calc R . .
N5 N 0.9533(3) 0.0261(2) 0.14689(11) 0.0656(8) Uani 1 1 d . . .
H5 H 0.9099 0.0516 0.1757 0.079 Uiso 1 1 calc R . .
C20 C 0.7483(3) 0.2301(2) 0.23285(12) 0.0455(7) Uani 1 1 d . . .
C28 C 0.2786(3) 0.1669(2) 0.23546(11) 0.0463(7) Uani 1 1 d . . .
C27 C 0.1568(3) 0.2072(3) 0.26025(12) 0.0581(8) Uani 1 1 d . . .
H27 H 0.0976 0.1655 0.2822 0.070 Uiso 1 1 calc R . .
O1 O 0.7039(2) 0.29003(17) 0.27465(8) 0.0702(6) Uani 1 1 d . . .
C15 C 1.1277(3) 0.5571(2) 0.06088(13) 0.0589(8) Uani 1 1 d . . .
H15 H 1.1513 0.6269 0.0550 0.071 Uiso 1 1 calc R . .
C8 C 0.9841(4) -0.1529(2) 0.03331(14) 0.0657(9) Uani 1 1 d . . .
H8 H 1.0510 -0.1686 0.0058 0.079 Uiso 1 1 calc R . .
C29 C 0.4542(3) 0.0642(2) 0.20562(12) 0.0513(8) Uani 1 1 d . . .
H29 H 0.5108 0.0052 0.2006 0.062 Uiso 1 1 calc R . .
C16 C 1.0297(3) 0.5303(2) 0.10108(12) 0.0499(8) Uani 1 1 d . . .
H16 H 0.9867 0.5814 0.1232 0.060 Uiso 1 1 calc R . .
C24 C 0.3344(3) 0.3325(2) 0.19308(12) 0.0554(8) Uani 1 1 d . . .
H24 H 0.3918 0.3744 0.1706 0.066 Uiso 1 1 calc R . .
C2 C 1.0815(4) 0.0581(3) 0.12734(13) 0.0591(9) Uani 1 1 d . . .
H2 H 1.1351 0.1120 0.1430 0.071 Uiso 1 1 calc R . .
C9 C 1.2510(4) 0.0184(2) 0.04622(13) 0.0608(9) Uani 1 1 d . . .
H9A H 1.2808 -0.0479 0.0302 0.073 Uiso 1 1 calc R . .
H9B H 1.3277 0.0437 0.0699 0.073 Uiso 1 1 calc R . .
C26 C 0.1272(3) 0.3104(3) 0.25128(12) 0.0643(9) Uani 1 1 d . . .
H26 H 0.0465 0.3394 0.2677 0.077 Uiso 1 1 calc R . .
C25 C 0.2147(3) 0.3736(3) 0.21819(13) 0.0623(9) Uani 1 1 d . . .
H25 H 0.1921 0.4439 0.2130 0.075 Uiso 1 1 calc R . .
C4 C 0.9041(4) -0.0528(2) 0.11375(13) 0.0572(8) Uani 1 1 d . . .
C7 C 0.8592(5) -0.2087(3) 0.03696(17) 0.0837(12) Uani 1 1 d . . .
H7 H 0.8422 -0.2631 0.0119 0.100 Uiso 1 1 calc R . .
C6 C 0.7576(5) -0.1845(3) 0.07789(19) 0.0942(13) Uani 1 1 d . . .
H6 H 0.6728 -0.2220 0.0786 0.113 Uiso 1 1 calc R . .
C31 C 1.0863(4) -0.0706(3) -0.11704(14) 0.0822(11) Uani 1 1 d . . .
H31A H 1.0007 -0.1011 -0.1023 0.123 Uiso 1 1 calc R . .
H31B H 1.1395 -0.1231 -0.1369 0.123 Uiso 1 1 calc R . .
H31C H 1.0624 -0.0147 -0.1423 0.123 Uiso 1 1 calc R . .
C30 C 0.7441(5) 0.2578(4) 0.32976(12) 0.1049(14) Uani 1 1 d . . .
H30A H 0.7124 0.1873 0.3361 0.157 Uiso 1 1 calc R . .
H30B H 0.7012 0.3034 0.3570 0.157 Uiso 1 1 calc R . .
H30C H 0.8457 0.2608 0.3333 0.157 Uiso 1 1 calc R . .
C5 C 0.7788(4) -0.1084(3) 0.11657(15) 0.0780(11) Uani 1 1 d . . .
H50 H 0.7112 -0.0941 0.1441 0.094 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0339(12) 0.0395(13) 0.0332(12) -0.0024(10) 0.0004(10) -0.0027(10)
O6 0.0478(12) 0.0582(12) 0.0476(11) -0.0067(10) 0.0154(10) -0.0048(10)
N3 0.0402(13) 0.0407(13) 0.0414(12) -0.0074(10) 0.0114(10) -0.0060(11)
O5 0.0549(12) 0.0524(12) 0.0522(11) -0.0185(10) 0.0183(10) -0.0044(10)
C13 0.0341(15) 0.0411(16) 0.0374(15) -0.0003(12) 0.0012(13) -0.0040(13)
O2 0.0594(13) 0.0713(15) 0.0542(12) 0.0060(12) 0.0028(11) 0.0054(13)
C18 0.0363(15) 0.0410(17) 0.0408(16) 0.0022(14) 0.0008(14) 0.0000(13)
C22 0.0409(16) 0.0525(17) 0.0381(15) 0.0033(14) 0.0002(13) -0.0121(15)
O3 0.0871(16) 0.0464(12) 0.0658(14) -0.0101(11) 0.0013(13) 0.0108(12)
C17 0.0351(15) 0.0371(15) 0.0385(15) -0.0058(12) 0.0018(13) -0.0023(13)
C14 0.0481(18) 0.0497(18) 0.0510(17) 0.0045(15) 0.0115(15) -0.0080(15)
C12 0.0396(16) 0.0468(17) 0.0413(15) -0.0056(14) 0.0027(14) -0.0027(14)
N4 0.0542(15) 0.0603(16) 0.0543(15) 0.0157(13) 0.0082(14) -0.0133(14)
O4 0.0770(16) 0.0764(17) 0.0856(17) 0.0091(13) 0.0069(15) 0.0238(15)
N1 0.0777(18) 0.0404(14) 0.0796(18) -0.0130(13) 0.0432(16) -0.0063(14)
C19 0.0369(15) 0.0462(16) 0.0414(15) -0.0021(13) 0.0083(13) -0.0020(13)
C11 0.062(2) 0.0443(18) 0.0567(19) 0.0076(16) 0.0196(17) -0.0010(17)
C1 0.0578(19) 0.0455(17) 0.0478(18) -0.0003(14) -0.0100(16) 0.0023(15)
C23 0.0352(15) 0.0526(18) 0.0412(15) 0.0020(14) -0.0019(13) -0.0087(14)
C21 0.0432(16) 0.0517(17) 0.0445(15) -0.0001(14) -0.0008(14) -0.0082(14)
C3 0.067(2) 0.0374(16) 0.0438(16) 0.0056(14) -0.0130(17) 0.0046(16)
C10 0.056(2) 0.0423(17) 0.071(2) -0.0087(16) 0.0221(18) 0.0030(15)
N5 0.084(2) 0.0682(18) 0.0447(15) -0.0035(14) 0.0093(15) -0.0002(16)
C20 0.0403(16) 0.0552(19) 0.0409(17) -0.0034(16) 0.0056(14) -0.0143(15)
C28 0.0405(16) 0.0606(19) 0.0376(15) 0.0060(14) -0.0028(14) -0.0090(15)
C27 0.0444(17) 0.085(3) 0.0453(17) 0.0043(17) 0.0031(15) -0.0052(18)
O1 0.0902(16) 0.0819(15) 0.0386(11) -0.0058(11) 0.0143(12) 0.0000(13)
C15 0.067(2) 0.0331(15) 0.077(2) -0.0024(16) 0.018(2) -0.0062(16)
C8 0.091(3) 0.0404(18) 0.065(2) 0.0033(16) -0.013(2) 0.0081(19)
C29 0.0461(18) 0.0532(19) 0.0545(18) 0.0061(16) 0.0064(15) -0.0056(15)
C16 0.0541(19) 0.0422(17) 0.0535(18) -0.0104(14) 0.0165(16) -0.0015(15)
C24 0.0488(18) 0.060(2) 0.0573(18) 0.0058(16) 0.0002(16) -0.0107(17)
C2 0.074(2) 0.058(2) 0.0448(18) -0.0070(17) -0.0089(17) -0.0005(19)
C9 0.056(2) 0.0560(19) 0.070(2) -0.0163(17) -0.0029(18) 0.0072(16)
C26 0.0460(18) 0.089(3) 0.058(2) -0.0060(19) 0.0010(17) 0.0053(19)
C25 0.055(2) 0.064(2) 0.068(2) -0.0066(17) -0.0029(19) 0.0028(18)
C4 0.071(2) 0.054(2) 0.0473(19) 0.0127(16) -0.0011(18) -0.0013(18)
C7 0.117(3) 0.0440(19) 0.090(3) 0.0062(19) -0.036(3) -0.020(2)
C6 0.094(3) 0.083(3) 0.106(3) 0.035(3) 0.000(3) -0.029(3)
C31 0.116(3) 0.066(2) 0.065(2) -0.004(2) -0.012(2) -0.004(2)
C30 0.140(4) 0.138(4) 0.0366(19) -0.007(2) 0.010(2) 0.000(3)
C5 0.088(3) 0.075(2) 0.071(2) 0.010(2) 0.008(2) -0.011(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C13 1.343(3) . ?
N2 C17 1.334(3) . ?
O6 C12 1.227(3) . ?
N3 C18 1.334(3) . ?
N3 C19 1.464(3) . ?
O5 C18 1.221(3) . ?
C13 C14 1.378(3) . ?
C13 C12 1.498(4) . ?
O2 C20 1.199(3) . ?
C18 C17 1.510(3) . ?
C22 C29 1.352(4) . ?
C22 C23 1.427(4) . ?
C22 C21 1.501(4) . ?
O3 C11 1.332(3) . ?
O3 C31 1.466(4) . ?
C17 C16 1.382(4) . ?
C14 C15 1.388(4) . ?
C12 N1 1.330(3) . ?
N4 C28 1.367(4) . ?
N4 C29 1.367(4) . ?
O4 C11 1.199(4) . ?
N1 C10 1.440(3) . ?
C19 C20 1.505(4) . ?
C19 C21 1.526(4) . ?
C11 C10 1.523(4) . ?
C1 C2 1.356(4) . ?
C1 C3 1.433(4) . ?
C1 C9 1.504(4) . ?
C23 C28 1.395(4) . ?
C23 C24 1.404(4) . ?
C3 C8 1.400(4) . ?
C3 C4 1.416(4) . ?
C10 C9 1.552(4) . ?
N5 C2 1.355(4) . ?
N5 C4 1.360(4) . ?
C20 O1 1.321(3) . ?
C28 C27 1.387(4) . ?
C27 C26 1.364(4) . ?
O1 C30 1.424(4) . ?
C15 C16 1.371(4) . ?
C8 C7 1.375(5) . ?
C24 C25 1.377(4) . ?
C26 C25 1.395(4) . ?
C4 C5 1.376(5) . ?
C7 C6 1.398(6) . ?
C6 C5 1.353(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 C17 117.8(2) . . ?
C18 N3 C19 120.4(2) . . ?
N2 C13 C14 122.9(2) . . ?
N2 C13 C12 117.2(2) . . ?
C14 C13 C12 119.9(2) . . ?
O5 C18 N3 123.4(2) . . ?
O5 C18 C17 120.2(2) . . ?
N3 C18 C17 116.4(2) . . ?
C29 C22 C23 106.5(2) . . ?
C29 C22 C21 126.9(3) . . ?
C23 C22 C21 126.5(3) . . ?
C11 O3 C31 115.2(3) . . ?
N2 C17 C16 123.0(2) . . ?
N2 C17 C18 117.6(2) . . ?
C16 C17 C18 119.4(2) . . ?
C13 C14 C15 118.3(3) . . ?
O6 C12 N1 124.0(2) . . ?
O6 C12 C13 122.7(2) . . ?
N1 C12 C13 113.3(2) . . ?
C28 N4 C29 108.9(2) . . ?
C12 N1 C10 125.3(2) . . ?
N3 C19 C20 110.8(2) . . ?
N3 C19 C21 111.8(2) . . ?
C20 C19 C21 109.6(2) . . ?
O4 C11 O3 123.9(3) . . ?
O4 C11 C10 125.2(3) . . ?
O3 C11 C10 111.0(3) . . ?
C2 C1 C3 106.2(3) . . ?
C2 C1 C9 126.3(3) . . ?
C3 C1 C9 127.3(3) . . ?
C28 C23 C24 118.1(3) . . ?
C28 C23 C22 107.2(2) . . ?
C24 C23 C22 134.7(3) . . ?
C22 C21 C19 111.8(2) . . ?
C8 C3 C4 118.5(3) . . ?
C8 C3 C1 135.0(3) . . ?
C4 C3 C1 106.4(3) . . ?
N1 C10 C11 110.5(3) . . ?
N1 C10 C9 109.4(2) . . ?
C11 C10 C9 114.6(2) . . ?
C2 N5 C4 109.1(3) . . ?
O2 C20 O1 124.0(3) . . ?
O2 C20 C19 124.9(3) . . ?
O1 C20 C19 111.1(3) . . ?
N4 C28 C27 129.7(3) . . ?
N4 C28 C23 107.4(3) . . ?
C27 C28 C23 122.8(3) . . ?
C26 C27 C28 117.5(3) . . ?
C20 O1 C30 116.1(3) . . ?
C16 C15 C14 119.3(3) . . ?
C7 C8 C3 118.6(4) . . ?
C22 C29 N4 109.9(3) . . ?
C15 C16 C17 118.6(3) . . ?
C25 C24 C23 119.4(3) . . ?
C1 C2 N5 110.7(3) . . ?
C1 C9 C10 112.9(3) . . ?
C27 C26 C25 121.8(3) . . ?
C24 C25 C26 120.3(3) . . ?
N5 C4 C5 130.1(3) . . ?
N5 C4 C3 107.5(3) . . ?
C5 C4 C3 122.4(3) . . ?
C8 C7 C6 120.9(3) . . ?
C5 C6 C7 122.1(4) . . ?
C6 C5 C4 117.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N2 C13 C14 -1.5(4) . . . . ?
C17 N2 C13 C12 179.1(2) . . . . ?
C19 N3 C18 O5 4.2(4) . . . . ?
C19 N3 C18 C17 -173.1(2) . . . . ?
C13 N2 C17 C16 1.0(4) . . . . ?
C13 N2 C17 C18 178.6(2) . . . . ?
O5 C18 C17 N2 161.9(2) . . . . ?
N3 C18 C17 N2 -20.7(3) . . . . ?
O5 C18 C17 C16 -20.4(4) . . . . ?
N3 C18 C17 C16 157.0(2) . . . . ?
N2 C13 C14 C15 0.8(4) . . . . ?
C12 C13 C14 C15 -179.9(3) . . . . ?
N2 C13 C12 O6 177.6(2) . . . . ?
C14 C13 C12 O6 -1.8(4) . . . . ?
N2 C13 C12 N1 -2.7(3) . . . . ?
C14 C13 C12 N1 177.9(3) . . . . ?
O6 C12 N1 C10 2.2(5) . . . . ?
C13 C12 N1 C10 -177.4(3) . . . . ?
C18 N3 C19 C20 -80.3(3) . . . . ?
C18 N3 C19 C21 157.1(2) . . . . ?
C31 O3 C11 O4 1.6(4) . . . . ?
C31 O3 C11 C10 -177.7(3) . . . . ?
C29 C22 C23 C28 0.0(3) . . . . ?
C21 C22 C23 C28 -177.3(2) . . . . ?
C29 C22 C23 C24 -179.3(3) . . . . ?
C21 C22 C23 C24 3.4(5) . . . . ?
C29 C22 C21 C19 -115.2(3) . . . . ?
C23 C22 C21 C19 61.5(3) . . . . ?
N3 C19 C21 C22 -179.1(2) . . . . ?
C20 C19 C21 C22 57.7(3) . . . . ?
C2 C1 C3 C8 -178.4(3) . . . . ?
C9 C1 C3 C8 7.0(5) . . . . ?
C2 C1 C3 C4 0.1(3) . . . . ?
C9 C1 C3 C4 -174.5(3) . . . . ?
C12 N1 C10 C11 -96.4(3) . . . . ?
C12 N1 C10 C9 136.5(3) . . . . ?
O4 C11 C10 N1 -0.4(4) . . . . ?
O3 C11 C10 N1 178.9(2) . . . . ?
O4 C11 C10 C9 123.8(3) . . . . ?
O3 C11 C10 C9 -56.9(3) . . . . ?
N3 C19 C20 O2 -64.7(3) . . . . ?
C21 C19 C20 O2 59.1(3) . . . . ?
N3 C19 C20 O1 116.3(2) . . . . ?
C21 C19 C20 O1 -119.9(2) . . . . ?
C29 N4 C28 C27 179.3(3) . . . . ?
C29 N4 C28 C23 0.8(3) . . . . ?
C24 C23 C28 N4 178.9(2) . . . . ?
C22 C23 C28 N4 -0.5(3) . . . . ?
C24 C23 C28 C27 0.3(4) . . . . ?
C22 C23 C28 C27 -179.1(2) . . . . ?
N4 C28 C27 C26 -179.1(3) . . . . ?
C23 C28 C27 C26 -0.8(4) . . . . ?
O2 C20 O1 C30 0.7(4) . . . . ?
C19 C20 O1 C30 179.7(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C4 C3 C8 C7 1.2(4) . . . . ?
C1 C3 C8 C7 179.5(3) . . . . ?
C23 C22 C29 N4 0.6(3) . . . . ?
C21 C22 C29 N4 177.8(2) . . . . ?
C28 N4 C29 C22 -0.9(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
N2 C17 C16 C15 0.2(4) . . . . ?
C18 C17 C16 C15 -177.3(3) . . . . ?
C28 C23 C24 C25 0.6(4) . . . . ?
C22 C23 C24 C25 179.8(3) . . . . ?
C3 C1 C2 N5 0.5(3) . . . . ?
C9 C1 C2 N5 175.2(3) . . . . ?
C4 N5 C2 C1 -1.0(4) . . . . ?
C2 C1 C9 C10 -87.2(4) . . . . ?
C3 C1 C9 C10 86.4(3) . . . . ?
N1 C10 C9 C1 56.2(3) . . . . ?
C11 C10 C9 C1 -68.6(3) . . . . ?
C28 C27 C26 C25 0.5(4) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C27 C26 C25 C24 0.4(5) . . . . ?
C2 N5 C4 C5 -178.9(3) . . . . ?
C2 N5 C4 C3 1.0(3) . . . . ?
C8 C3 C4 N5 178.1(3) . . . . ?
C1 C3 C4 N5 -0.7(3) . . . . ?
C8 C3 C4 C5 -2.0(4) . . . . ?
C1 C3 C4 C5 179.2(3) . . . . ?
C3 C8 C7 C6 0.8(5) . . . . ?
C8 C7 C6 C5 -2.2(6) . . . . ?
C7 C6 C5 C4 1.4(6) . . . . ?
N5 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.099