# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global
_publ_contact_author_email       DIEDERICH@ORG.CHEM.ETHZ.CH

_publ_contact_author_name        'Prof. Francois Diederich'
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?
_publ_contact_author_address     
;
Department of Chemistry
ETH Zuerich
ETH Hoenggerberg
HCI G313
Zuerich
CH-8093
SWITZERLAND
;

_publ_section_title              
;
H-bonded complexes of adenine with Rebek imide receptors are stabilised by
cation-pi interactions and destabilised by stacking with
perfluoroaromatics
;

loop_
_publ_author_name
'Raffaella Faraoni'
'Ronald K. Castellano'
'Volker Gramlich'
'Francois Diederich'

data_complex1c-2
_database_code_depnum_ccdc_archive 'CCDC 224117'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C29 H37 I N8 O4'
_chemical_formula_weight         688.57
_chemical_melting_point          ?
_chemical_compound_source        ?
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.578(2)
_cell_length_b                   12.724(3)
_cell_length_c                   15.621(3)
_cell_angle_alpha                109.03(3)
_cell_angle_beta                 95.46(3)
_cell_angle_gamma                102.40(3)
_cell_volume                     1548.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'PICKER 4-circle Stoe upgrade'
_diffrn_measurement_method       ' \w scans'
_diffrn_standards_number         1
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2457
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         19.97
_reflns_number_total             2457
_reflns_number_observed          1891
_reflns_observed_criterion       >2sigma(I)
_computing_data_collection       'PICKER STOE DIF4'
_computing_cell_refinement       'STOE DIF4'
_computing_data_reduction        'STOE REDU4'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELXLTL-Plus
_computing_publication_material  SHELXL-93

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^  or
flagged by the user for potential systematic errors. Weighted R-factors  wR and
all goodnesses 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 observed criterion  of F^2^ >
2sigma(F^2^) is used only for calculating _R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.0482P)^2^+3.2333P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     385
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_obs          0.0514
_refine_ls_wR_factor_all         0.1251
_refine_ls_wR_factor_obs         0.1093
_refine_ls_goodness_of_fit_all   1.153
_refine_ls_goodness_of_fit_obs   1.180
_refine_ls_restrained_S_all      1.156
_refine_ls_restrained_S_obs      1.183
_refine_ls_shift/esd_max         2.065
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
I I 0.97659(9) 1.26716(7) 0.92271(7) 0.0834(4) Uani 1 d . .
O4 O 0.7240(7) 0.6272(6) 0.6187(5) 0.056(2) Uani 1 d . .
N3" N 0.4397(8) 0.7940(7) 0.6404(5) 0.045(2) Uani 1 d . .
N5" N 0.0738(8) 0.7190(7) 0.6330(5) 0.049(2) Uani 1 d . .
H5"A H 0.1238(8) 0.6622(7) 0.6264(5) 0.069 Uiso 1 d R .
H5"B H -0.0340(8) 0.7042(7) 0.6316(5) 0.069 Uiso 1 d R .
C5" C 0.1559(12) 0.8237(11) 0.6439(7) 0.045(3) Uani 1 d . .
N3 N 0.4617(8) 0.5655(7) 0.6228(5) 0.039(2) Uani 1 d . .
H3A H 0.4475(8) 0.6291(7) 0.6133(5) 0.055 Uiso 1 d R .
C9 C 0.4856(9) 0.3494(8) 0.5948(6) 0.042(2) Uani 1 d . .
H9A H 0.4980(9) 0.2786(8) 0.6006(6) 0.058 Uiso 1 d R .
H9B H 0.4651(9) 0.3376(8) 0.5305(6) 0.058 Uiso 1 d R .
O2 O 0.1971(8) 0.5182(6) 0.6300(5) 0.061(2) Uani 1 d . .
O13 O 0.6653(8) 0.6831(6) 0.8220(5) 0.064(2) Uani 1 d . .
N6" N 0.0773(9) 0.9099(9) 0.6554(6) 0.064(3) Uani 1 d . .
N1' N 0.1742(8) 0.8515(8) 0.8677(5) 0.051(2) Uani 1 d . .
C2 C 0.3241(11) 0.4909(8) 0.6299(6) 0.039(2) Uani 1 d . .
C7 C 0.5422(10) 0.4843(8) 0.7949(6) 0.043(2) Uani 1 d . .
N1" N 0.5575(9) 0.9771(8) 0.6602(6) 0.050(2) Uani 1 d . .
C2' C 0.2169(12) 0.7539(10) 0.8536(7) 0.054(3) Uani 1 d . .
H2'A H 0.1342(12) 0.6845(10) 0.8425(7) 0.076 Uiso 1 d R .
C4 C 0.6183(11) 0.5526(9) 0.6253(6) 0.042(3) Uani 1 d . .
C12 C 0.1865(10) 0.2846(8) 0.5924(7) 0.061(3) Uani 1 d . .
H12A H 0.1653(10) 0.2737(8) 0.5282(7) 0.086 Uiso 1 d R .
H12B H 0.1991(10) 0.2144(8) 0.5991(7) 0.086 Uiso 1 d R .
H12C H 0.0974(10) 0.3057(8) 0.6204(7) 0.086 Uiso 1 d R .
C4' C 0.4936(11) 0.8486(9) 0.8682(6) 0.049(3) Uani 1 d . .
H4'A H 0.6047(11) 0.8460(9) 0.8684(6) 0.068 Uiso 1 d R .
C4" C 0.3255(11) 0.8590(11) 0.6468(7) 0.047(3) Uani 1 d . .
C13 C 0.5439(13) 0.6114(10) 0.8199(7) 0.050(3) Uani 1 d . .
C7" C 0.1648(14) 1.0132(12) 0.6670(8) 0.071(4) Uani 1 d . .
H7"A H 0.1031(14) 1.0691(12) 0.6737(8) 0.100 Uiso 1 d R .
C10' C 0.4498(11) 0.9530(8) 0.8820(6) 0.042(2) Uani 1 d . .
C2" C 0.5747(11) 0.8723(10) 0.6494(7) 0.055(3) Uani 1 d . .
H2A H 0.6781(11) 0.8548(10) 0.6489(7) 0.077 Uiso 1 d R .
C3' C 0.3752(11) 0.7485(9) 0.8538(6) 0.046(3) Uani 1 d . .
N14 N 0.4058(9) 0.6416(7) 0.8404(5) 0.054(2) Uani 1 d . .
H14A H 0.3255(9) 0.5885(7) 0.8477(5) 0.076 Uiso 1 d R .
N8" N 0.3196(11) 1.0553(8) 0.6697(6) 0.065(3) Uani 1 d . .
C5 C 0.6420(9) 0.4431(8) 0.6388(7) 0.041(3) Uani 1 d . .
C1 C 0.3438(9) 0.3799(7) 0.6386(7) 0.036(2) Uani 1 d . .
C5' C 0.5687(11) 1.0573(9) 0.8981(7) 0.059(3) Uani 1 d . .
H5'A H 0.6812(11) 1.0582(9) 0.9002(7) 0.082 Uiso 1 d R .
C10" C 0.6851(12) 1.0818(9) 0.6729(8) 0.073(3) Uani 1 d . .
H10A H 0.7752(12) 1.0876(9) 0.7173(8) 0.102 Uiso 1 d R .
H10B H 0.6450(12) 1.1486(9) 0.6961(8) 0.102 Uiso 1 d R .
C11 C 0.7834(11) 0.4126(9) 0.5924(7) 0.065(3) Uani 1 d . .
H11A H 0.8017(11) 0.3443(9) 0.6005(7) 0.090 Uiso 1 d R .
H11B H 0.7565(11) 0.3986(9) 0.5279(7) 0.090 Uiso 1 d R .
H11C H 0.8798(11) 0.4747(9) 0.6190(7) 0.090 Uiso 1 d R .
C9" C 0.3959(12) 0.9706(10) 0.6596(7) 0.049(3) Uani 1 d . .
C6 C 0.6778(10) 0.4599(8) 0.7406(7) 0.049(3) Uani 1 d . .
H6A H 0.7034(10) 0.3923(8) 0.7461(7) 0.069 Uiso 1 d R .
H6B H 0.7728(10) 0.5230(8) 0.7680(7) 0.069 Uiso 1 d R .
C8' C 0.2443(12) 1.0592(10) 0.8996(7) 0.060(3) Uani 1 d . .
H8'A H 0.1329(12) 1.0600(10) 0.9011(7) 0.084 Uiso 1 d R .
C9' C 0.2873(11) 0.9565(9) 0.8837(7) 0.047(3) Uani 1 d . .
C6' C 0.5231(13) 1.1563(9) 0.9124(7) 0.061(3) Uani 1 d . .
H6'A H 0.6014(13) 1.2270(9) 0.9212(7) 0.086 Uiso 1 d R .
C7' C 0.3611(13) 1.1572(9) 0.9138(7) 0.060(3) Uani 1 d . .
H7'A H 0.3312(13) 1.2284(9) 0.9257(7) 0.084 Uiso 1 d R .
C8 C 0.3793(10) 0.3977(8) 0.7404(7) 0.050(3) Uani 1 d . .
H8A H 0.2932(10) 0.4239(8) 0.7685(7) 0.070 Uiso 1 d R .
H8B H 0.3780(10) 0.3247(8) 0.7462(7) 0.070 Uiso 1 d R .
C11' C 0.0015(11) 0.8497(10) 0.8637(8) 0.071(3) Uani 1 d . .
H11D H -0.0629(11) 0.7732(10) 0.8524(8) 0.099 Uiso 1 d R .
H11E H -0.0110(11) 0.9008(10) 0.9217(8) 0.099 Uiso 1 d R .
H11F H -0.0337(11) 0.8753(10) 0.8155(8) 0.099 Uiso 1 d R .
C10 C 0.5802(14) 0.4714(10) 0.8886(7) 0.082(3) Uani 1 d . .
H10C H 0.4957(14) 0.4869(10) 0.9231(7) 0.114 Uiso 1 d R .
H10D H 0.5891(14) 0.3948(10) 0.8800(7) 0.114 Uiso 1 d R .
H10E H 0.6813(14) 0.5259(10) 0.9215(7) 0.114 Uiso 1 d R .
C11" C 0.7382(14) 1.0752(11) 0.5847(10) 0.110(5) Uani 1 d . .
H11G H 0.8225(14) 1.1428(11) 0.5932(10) 0.155 Uiso 1 d R .
H11H H 0.7784(14) 1.0082(11) 0.5623(10) 0.155 Uiso 1 d R .
H11I H 0.6474(14) 1.0696(11) 0.5410(10) 0.155 Uiso 1 d R .
O1X O 0.1222(11) 0.5252(7) 0.8903(7) 0.112(3) Uani 1 d D .
H1X H 0.0912(175) 0.4397(28) 0.8835(91) 0.200 Uiso 1 d D .
H1Y H 0.1216(192) 0.5874(106) 0.9558(27) 0.200 Uiso 1 d D .
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
I 0.0688(5) 0.0551(5) 0.1239(8) 0.0299(5) 0.0256(4) 0.0104(4)
O4 0.038(4) 0.052(5) 0.090(6) 0.042(4) 0.022(3) 0.006(3)
N3" 0.038(5) 0.034(6) 0.065(6) 0.024(4) 0.015(4) 0.005(4)
N5" 0.036(4) 0.047(6) 0.077(6) 0.035(5) 0.017(4) 0.013(4)
C5" 0.055(7) 0.039(9) 0.048(7) 0.021(6) 0.009(5) 0.019(6)
N3 0.039(5) 0.027(5) 0.058(6) 0.023(4) 0.009(4) 0.012(4)
C9 0.053(6) 0.025(6) 0.054(7) 0.019(5) 0.017(5) 0.014(5)
O2 0.035(4) 0.050(5) 0.120(6) 0.052(5) 0.022(4) 0.019(3)
O13 0.051(4) 0.040(5) 0.084(6) 0.007(4) 0.011(4) -0.002(4)
N6" 0.061(5) 0.050(7) 0.099(8) 0.041(6) 0.021(5) 0.022(5)
N1' 0.035(5) 0.066(8) 0.058(6) 0.033(5) 0.017(4) 0.003(5)
C2 0.033(6) 0.035(7) 0.055(7) 0.029(5) 0.008(5) 0.004(5)
C7 0.053(6) 0.042(7) 0.041(7) 0.027(5) 0.008(5) 0.008(5)
N1" 0.053(6) 0.040(7) 0.063(6) 0.030(5) 0.017(4) 0.004(5)
C2' 0.061(7) 0.036(8) 0.069(8) 0.020(6) 0.027(6) 0.010(6)
C4 0.030(6) 0.041(8) 0.058(7) 0.022(6) 0.005(5) 0.012(5)
C12 0.050(6) 0.030(6) 0.098(9) 0.025(6) 0.010(5) -0.003(5)
C4' 0.041(6) 0.053(8) 0.053(7) 0.021(6) 0.016(5) 0.010(6)
C4" 0.034(6) 0.060(11) 0.059(7) 0.030(6) 0.011(5) 0.020(7)
C13 0.057(7) 0.046(8) 0.048(7) 0.016(6) 0.011(5) 0.011(6)
C7" 0.068(8) 0.063(10) 0.102(10) 0.045(8) 0.020(7) 0.032(7)
C10' 0.054(6) 0.033(7) 0.044(7) 0.020(5) 0.014(5) 0.009(6)
C2" 0.048(7) 0.048(9) 0.082(9) 0.035(6) 0.019(5) 0.016(6)
C3' 0.045(7) 0.043(9) 0.048(7) 0.016(6) 0.017(5) 0.006(6)
N14 0.060(5) 0.031(6) 0.071(6) 0.013(5) 0.032(4) 0.006(4)
N8" 0.072(7) 0.035(6) 0.096(8) 0.028(5) 0.022(5) 0.018(5)
C5 0.035(5) 0.039(7) 0.064(8) 0.028(6) 0.022(5) 0.020(5)
C1 0.041(5) 0.020(6) 0.052(7) 0.019(5) 0.015(5) 0.006(4)
C5' 0.051(6) 0.044(8) 0.084(9) 0.029(6) 0.015(5) 0.007(6)
C10" 0.073(7) 0.051(8) 0.094(10) 0.034(7) 0.025(7) -0.005(6)
C11 0.054(6) 0.066(8) 0.093(9) 0.038(7) 0.034(6) 0.030(6)
C9" 0.061(8) 0.032(9) 0.055(8) 0.022(6) 0.014(5) 0.002(6)
C6 0.049(6) 0.041(6) 0.063(8) 0.029(6) 0.002(5) 0.010(5)
C8' 0.059(7) 0.046(8) 0.082(9) 0.031(6) 0.022(6) 0.011(6)
C9' 0.052(7) 0.044(8) 0.052(7) 0.024(6) 0.021(5) 0.007(6)
C6' 0.082(9) 0.037(8) 0.064(8) 0.026(6) 0.017(6) 0.000(6)
C7' 0.065(7) 0.041(8) 0.078(9) 0.024(6) 0.016(6) 0.015(6)
C8 0.053(6) 0.043(7) 0.066(8) 0.030(6) 0.024(5) 0.017(5)
C11' 0.054(7) 0.059(9) 0.097(10) 0.030(7) 0.023(6) 0.003(5)
C10 0.126(10) 0.065(9) 0.039(8) 0.014(7) -0.002(6) 0.010(7)
C11" 0.107(10) 0.090(11) 0.137(13) 0.069(10) 0.040(9) -0.021(7)
O1X 0.138(7) 0.070(6) 0.148(8) 0.049(6) 0.094(7) 0.021(5)

_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
O4 C4 1.202(12) . ?
N3" C2" 1.317(13) . ?
N3" C4" 1.401(12) . ?
N5" C5" 1.314(13) . ?
C5" N6" 1.380(13) . ?
C5" C4" 1.419(14) . ?
N3 C2 1.385(13) . ?
N3 C4 1.386(9) . ?
C9 C1 1.511(10) . ?
C9 C5 1.516(13) . ?
O2 C2 1.213(8) . ?
O13 C13 1.218(12) . ?
N6" C7" 1.310(15) . ?
N1' C2' 1.325(13) . ?
N1' C9' 1.403(13) . ?
N1' C11' 1.472(10) . ?
C2 C1 1.505(13) . ?
C7 C6 1.529(12) . ?
C7 C13 1.530(14) . ?
C7 C10 1.538(13) . ?
C7 C8 1.546(12) . ?
N1" C2" 1.331(13) . ?
N1" C9" 1.370(10) . ?
N1" C10" 1.473(13) . ?
C2' C3' 1.374(12) . ?
C4 C5 1.527(14) . ?
C12 C1 1.534(12) . ?
C4' C3' 1.385(14) . ?
C4' C10' 1.412(13) . ?
C4" C9" 1.36(2) . ?
C13 N14 1.357(11) . ?
C7" N8" 1.312(13) . ?
C10' C9' 1.407(11) . ?
C10' C5' 1.421(14) . ?
C3' N14 1.394(12) . ?
N8" C9" 1.352(13) . ?
C5 C6 1.526(12) . ?
C5 C11 1.527(11) . ?
C1 C8 1.523(12) . ?
C5' C6' 1.354(14) . ?
C10" C11" 1.47(2) . ?
C8' C7' 1.360(14) . ?
C8' C9' 1.385(14) . ?
C6' C7' 1.394(12) . ?
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" N3" C4" 101.3(10) . . ?
N5" C5" N6" 119.9(9) . . ?
N5" C5" C4" 125.3(10) . . ?
N6" C5" C4" 114.8(13) . . ?
C2 N3 C4 128.1(7) . . ?
C1 C9 C5 112.1(7) . . ?
C7" N6" C5" 117.6(9) . . ?
C2' N1' C9' 122.4(8) . . ?
C2' N1' C11' 119.1(8) . . ?
C9' N1' C11' 118.4(8) . . ?
O2 C2 N3 119.3(8) . . ?
O2 C2 C1 123.9(7) . . ?
N3 C2 C1 116.8(7) . . ?
C6 C7 C13 109.4(7) . . ?
C6 C7 C10 109.4(8) . . ?
C13 C7 C10 103.9(8) . . ?
C6 C7 C8 109.5(7) . . ?
C13 C7 C8 115.1(8) . . ?
C10 C7 C8 109.4(8) . . ?
C2" N1" C9" 106.4(8) . . ?
C2" N1" C10" 127.8(9) . . ?
C9" N1" C10" 125.7(9) . . ?
N1' C2' C3' 122.3(9) . . ?
O4 C4 N3 119.0(8) . . ?
O4 C4 C5 125.2(7) . . ?
N3 C4 C5 115.7(8) . . ?
C3' C4' C10' 119.7(8) . . ?
C9" C4" N3" 111.8(9) . . ?
C9" C4" C5" 119.3(10) . . ?
N3" C4" C5" 128.9(14) . . ?
O13 C13 N14 121.1(9) . . ?
O13 C13 C7 121.2(9) . . ?
N14 C13 C7 117.7(9) . . ?
N8" C7" N6" 133.0(10) . . ?
C9' C10' C4' 120.4(8) . . ?
C9' C10' C5' 118.4(8) . . ?
C4' C10' C5' 121.1(9) . . ?
N3" C2" N1" 115.3(8) . . ?
C2' C3' C4' 118.6(8) . . ?
C2' C3' N14 117.1(8) . . ?
C4' C3' N14 124.2(8) . . ?
C13 N14 C3' 126.8(8) . . ?
C7" N8" C9" 108.9(11) . . ?
C9 C5 C6 108.3(7) . . ?
C9 C5 C4 107.8(7) . . ?
C6 C5 C4 111.5(8) . . ?
C9 C5 C11 111.6(7) . . ?
C6 C5 C11 110.2(7) . . ?
C4 C5 C11 107.5(7) . . ?
C2 C1 C9 109.1(7) . . ?
C2 C1 C8 108.4(7) . . ?
C9 C1 C8 109.0(7) . . ?
C2 C1 C12 109.5(7) . . ?
C9 C1 C12 111.2(7) . . ?
C8 C1 C12 109.5(7) . . ?
C6' C5' C10' 119.7(9) . . ?
N1" C10" C11" 109.9(9) . . ?
N8" C9" C4" 126.3(9) . . ?
N8" C9" N1" 128.5(10) . . ?
C4" C9" N1" 105.2(8) . . ?
C5 C6 C7 116.0(7) . . ?
C7' C8' C9' 119.2(9) . . ?
C8' C9' N1' 122.9(9) . . ?
C8' C9' C10' 120.7(8) . . ?
N1' C9' C10' 116.4(8) . . ?
C5' C6' C7' 120.6(9) . . ?
C8' C7' C6' 121.4(9) . . ?
C1 C8 C7 115.6(7) . . ?
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
#====END

data_complex1d-2
_database_code_depnum_ccdc_archive 'CCDC 224118'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C28 H32 N8 O3'
_chemical_formula_weight         528.62
_chemical_melting_point          ?
_chemical_compound_source        ?
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           ?
_symmetry_space_group_name_H-M   ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   8.097(4)
_cell_length_b                   9.350(5)
_cell_length_c                   18.786(9)
_cell_angle_alpha                76.19(3)
_cell_angle_beta                 78.45(3)
_cell_angle_gamma                85.08(3)
_cell_volume                     1352.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2768
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         49.99
_reflns_number_total             2768
_reflns_number_observed          2010
_reflns_observed_criterion       >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for
0 with very negative F^2^  or flagged by the user for potential systematic
errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating
R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.1472P] 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    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0009(4)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_obs          0.0432
_refine_ls_wR_factor_all         0.1218
_refine_ls_wR_factor_obs         0.1065
_refine_ls_goodness_of_fit_all   1.041
_refine_ls_goodness_of_fit_obs   1.097
_refine_ls_restrained_S_all      1.041
_refine_ls_restrained_S_obs      1.097
_refine_ls_shift/esd_max         -0.560
_refine_ls_shift/esd_mean        0.127
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N3 N 0.2938(3) 0.7708(3) 0.26388(12) 0.0519(7) Uani 1 d . .
H1A H 0.3347(3) 0.8176(3) 0.21935(12) 0.080 Uiso 1 d R .
O2 O 0.5506(3) 0.6641(2) 0.27092(11) 0.0643(6) Uani 1 d . .
O4 O 0.0468(3) 0.8889(3) 0.25021(12) 0.0716(7) Uani 1 d . .
N14 N 0.2608(3) 1.0621(3) 0.33650(14) 0.0587(7) Uani 1 d . .
H4A H 0.1540(3) 1.0593(3) 0.35328(14) 0.080 Uiso 1 d R .
O13 O 0.5075(3) 0.9383(2) 0.35152(14) 0.0771(7) Uani 1 d . .
N1" N 0.3796(3) 1.1587(3) 0.03107(13) 0.0529(7) Uani 1 d . .
C4" C 0.5665(3) 1.0486(3) 0.0975(2) 0.0457(8) Uani 1 d . .
C5 C 0.0519(3) 0.7183(3) 0.3676(2) 0.0522(8) Uani 1 d . .
N3" N 0.4170(3) 0.9811(3) 0.13055(13) 0.0558(7) Uani 1 d . .
N8" N 0.6634(3) 1.2464(3) -0.00898(15) 0.0646(8) Uani 1 d . .
C9" C 0.5454(4) 1.1580(3) 0.0362(2) 0.0495(8) Uani 1 d . .
C9 C 0.1466(3) 0.5691(3) 0.3849(2) 0.0541(8) Uani 1 d . .
H12A H 0.0999(3) 0.5152(3) 0.4348(2) 0.080 Uiso 1 d R .
H12B H 0.1322(3) 0.5117(3) 0.3499(2) 0.080 Uiso 1 d R .
N1' N 0.0212(3) 1.2562(3) 0.29651(15) 0.0661(8) Uani 1 d . .
C1 C 0.3336(3) 0.5896(3) 0.3790(2) 0.0471(8) Uani 1 d . .
N5" N 0.7642(3) 0.9246(3) 0.17372(15) 0.0745(9) Uani 1 d . .
H15A H 0.8653(3) 0.9138(3) 0.18251(15) 0.080 Uiso 1 d R .
H15B H 0.6867(3) 0.8691(3) 0.20229(15) 0.080 Uiso 1 d R .
C2 C 0.4042(4) 0.6749(3) 0.3014(2) 0.0488(8) Uani 1 d . .
C8 C 0.3552(4) 0.6783(3) 0.4354(2) 0.0550(8) Uani 1 d . .
H17A H 0.3208(4) 0.6182(3) 0.4852(2) 0.080 Uiso 1 d R .
H17B H 0.4743(4) 0.6953(3) 0.4291(2) 0.080 Uiso 1 d R .
C4 C 0.1266(4) 0.7996(3) 0.2900(2) 0.0514(8) Uani 1 d . .
C9' C 0.3139(4) 1.1857(3) 0.2802(2) 0.0527(8) Uani 1 d . .
C13 C 0.3541(4) 0.9451(3) 0.3684(2) 0.0547(8) Uani 1 d . .
C5" C 0.7275(4) 1.0271(4) 0.1159(2) 0.0538(8) Uani 1 d . .
C10' C 0.1808(4) 1.2876(3) 0.2592(2) 0.0555(8) Uani 1 d . .
C6 C 0.0750(3) 0.8070(3) 0.4244(2) 0.0578(9) Uani 1 d . .
H23A H 0.0153(3) 0.7587(3) 0.4732(2) 0.080 Uiso 1 d R .
H23B H 0.0212(3) 0.9039(3) 0.4110(2) 0.080 Uiso 1 d R .
N6" N 0.8501(3) 1.1128(3) 0.0722(2) 0.0657(8) Uani 1 d . .
C2" C 0.3089(4) 1.0517(4) 0.0891(2) 0.0577(9) Uani 1 d . .
H25A H 0.1955(4) 1.0300(4) 0.0990(2) 0.080 Uiso 1 d R .
C11 C -0.1363(4) 0.7009(4) 0.3735(2) 0.0716(10) Uani 1 d . .
H26A H -0.1516(4) 0.6454(4) 0.3385(2) 0.080 Uiso 1 d R .
H26B H -0.1919(4) 0.7962(4) 0.3623(2) 0.080 Uiso 1 d R .
H26C H -0.1837(4) 0.6495(4) 0.4231(2) 0.080 Uiso 1 d R .
C8' C 0.4752(4) 1.2127(4) 0.2446(2) 0.0616(9) Uani 1 d . .
H27A H 0.5621(4) 1.1458(4) 0.2575(2) 0.080 Uiso 1 d R .
C7 C 0.2577(4) 0.8276(3) 0.4306(2) 0.0531(8) Uani 1 d . .
C5' C 0.2206(4) 1.4163(4) 0.2030(2) 0.0633(9) Uani 1 d . .
C4' C 0.0831(6) 1.5141(4) 0.1858(2) 0.0811(11) Uani 1 d . .
C12 C 0.4289(4) 0.4414(3) 0.3949(2) 0.0642(9) Uani 1 d . .
H31A H 0.5462(4) 0.4571(3) 0.3913(2) 0.080 Uiso 1 d R .
H31B H 0.4168(4) 0.3870(3) 0.3590(2) 0.080 Uiso 1 d R .
H31C H 0.3841(4) 0.3866(3) 0.4441(2) 0.080 Uiso 1 d R .
C10" C 0.2932(4) 1.2549(4) -0.0258(2) 0.0630(9) Uani 1 d . .
H32A H 0.1983(4) 1.2045(4) -0.0314(2) 0.080 Uiso 1 d R .
H32B H 0.3705(4) 1.2745(4) -0.0733(2) 0.080 Uiso 1 d R .
C10 C 0.2569(5) 0.8798(4) 0.5026(2) 0.0805(11) Uani 1 d . .
H33A H 0.1954(5) 0.9727(4) 0.5005(2) 0.080 Uiso 1 d R .
H33B H 0.3709(5) 0.8909(4) 0.5071(2) 0.080 Uiso 1 d R .
H33C H 0.2041(5) 0.8082(4) 0.5449(2) 0.080 Uiso 1 d R .
C3' C -0.0740(5) 1.4815(5) 0.2219(2) 0.0859(12) Uani 1 d . .
H34A H -0.1646(5) 1.5452(5) 0.2106(2) 0.080 Uiso 1 d R .
C7" C 0.8093(4) 1.2145(4) 0.0144(2) 0.0723(10) Uani 1 d . .
H35A H 0.8978(4) 1.2723(4) -0.0140(2) 0.080 Uiso 1 d R .
C6' C 0.3872(5) 1.4408(4) 0.1678(2) 0.0759(10) Uani 1 d . .
C7' C 0.5110(5) 1.3411(4) 0.1882(2) 0.0744(10) Uani 1 d . .
H37A H 0.6221(5) 1.3582(4) 0.1644(2) 0.080 Uiso 1 d R .
C2' C -0.1003(4) 1.3516(4) 0.2764(2) 0.0799(11) Uani 1 d . .
H38A H -0.2104(4) 1.3304(4) 0.3004(2) 0.080 Uiso 1 d R .
C11" C 0.2316(5) 1.3956(4) -0.0053(2) 0.0869(12) Uani 1 d . .
H1B H 0.1761(5) 1.4554(4) -0.0434(2) 0.080 Uiso 1 d R .
H1C H 0.3255(5) 1.4464(4) -0.0006(2) 0.080 Uiso 1 d R .
H1D H 0.1536(5) 1.3764(4) 0.0413(2) 0.080 Uiso 1 d R .
H2 H 0.4140(5) 1.5242(4) 0.1249(2) 0.069 Uiso 1 d R .
H1 H 0.1084(5) 1.6047(4) 0.1463(2) 0.107 Uiso 1 d 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
N3 0.034(2) 0.070(2) 0.0440(14) 0.0023(12) -0.0105(11) 0.0044(12)
O2 0.0379(14) 0.080(2) 0.0664(14) -0.0096(12) -0.0047(11) 0.0124(11)
O4 0.0428(13) 0.089(2) 0.0696(15) 0.0173(13) -0.0245(11) 0.0056(12)
N14 0.0391(15) 0.059(2) 0.069(2) -0.0049(15) -0.0033(13) 0.0042(13)
O13 0.039(2) 0.076(2) 0.106(2) -0.0020(14) -0.0146(12) 0.0067(11)
N1" 0.037(2) 0.058(2) 0.057(2) 0.0043(14) -0.0167(12) 0.0052(12)
C4" 0.032(2) 0.055(2) 0.046(2) -0.002(2) -0.0086(14) 0.0033(14)
C5 0.032(2) 0.064(2) 0.051(2) 0.004(2) -0.0071(13) 0.0025(14)
N3" 0.039(2) 0.070(2) 0.051(2) 0.0019(13) -0.0110(13) 0.0004(13)
N8" 0.041(2) 0.067(2) 0.076(2) 0.0081(15) -0.0159(15) -0.0044(14)
C9" 0.035(2) 0.054(2) 0.057(2) -0.007(2) -0.0102(15) 0.0034(15)
C9 0.044(2) 0.059(2) 0.053(2) 0.000(2) -0.0078(14) 0.0014(14)
N1' 0.047(2) 0.069(2) 0.074(2) -0.0091(15) -0.0089(15) 0.0132(15)
C1 0.038(2) 0.054(2) 0.045(2) -0.0041(15) -0.0124(13) 0.0097(14)
N5" 0.044(2) 0.100(2) 0.068(2) 0.010(2) -0.0204(14) -0.0004(15)
C2 0.036(2) 0.059(2) 0.051(2) -0.011(2) -0.012(2) 0.0059(15)
C8 0.047(2) 0.062(2) 0.050(2) -0.003(2) -0.0148(14) 0.010(2)
C4 0.035(2) 0.062(2) 0.053(2) -0.001(2) -0.015(2) -0.0001(15)
C9' 0.046(2) 0.053(2) 0.056(2) -0.010(2) -0.004(2) -0.003(2)
C13 0.045(2) 0.056(2) 0.064(2) -0.014(2) -0.014(2) 0.006(2)
C5" 0.044(2) 0.065(2) 0.047(2) -0.006(2) -0.010(2) 0.007(2)
C10' 0.051(2) 0.055(2) 0.056(2) -0.011(2) -0.005(2) 0.005(2)
C6 0.043(2) 0.061(2) 0.056(2) 0.001(2) -0.0005(15) 0.0101(15)
N6" 0.042(2) 0.080(2) 0.068(2) 0.001(2) -0.0143(14) 0.0008(15)
C2" 0.038(2) 0.069(2) 0.059(2) 0.000(2) -0.009(2) -0.002(2)
C11 0.038(2) 0.084(2) 0.078(2) 0.006(2) -0.006(2) 0.000(2)
C8' 0.049(2) 0.063(2) 0.069(2) -0.014(2) -0.006(2) 0.000(2)
C7 0.047(2) 0.061(2) 0.048(2) -0.009(2) -0.0090(14) 0.0090(15)
C5' 0.070(3) 0.059(2) 0.059(2) -0.011(2) -0.010(2) 0.002(2)
C4' 0.094(3) 0.072(3) 0.070(2) -0.006(2) -0.017(2) 0.016(2)
C12 0.063(2) 0.064(2) 0.061(2) -0.006(2) -0.017(2) 0.016(2)
C10" 0.048(2) 0.065(2) 0.074(2) -0.004(2) -0.020(2) 0.003(2)
C10 0.086(3) 0.084(3) 0.072(3) -0.021(2) -0.015(2) 0.010(2)
C3' 0.083(3) 0.087(3) 0.083(3) -0.012(2) -0.027(2) 0.035(2)
C7" 0.048(2) 0.077(2) 0.080(3) 0.008(2) -0.011(2) -0.010(2)
C6' 0.081(3) 0.068(2) 0.069(2) 0.000(2) -0.006(2) -0.011(2)
C7' 0.060(2) 0.083(3) 0.075(2) -0.019(2) 0.006(2) -0.015(2)
C2' 0.052(2) 0.093(3) 0.087(3) -0.015(2) -0.012(2) 0.018(2)
C11" 0.075(3) 0.080(3) 0.108(3) -0.017(2) -0.033(2) 0.013(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
N3 C4 1.371(4) . ?
N3 C2 1.383(4) . ?
O2 C2 1.216(3) . ?
O4 C4 1.215(3) . ?
N14 C13 1.361(4) . ?
N14 C9' 1.400(4) . ?
O13 C13 1.219(3) . ?
N1" C2" 1.358(4) . ?
N1" C9" 1.365(4) . ?
N1" C10" 1.473(4) . ?
C4" C9" 1.373(4) . ?
C4" N3" 1.376(4) . ?
C4" C5" 1.400(4) . ?
C5 C4 1.506(4) . ?
C5 C11 1.526(4) . ?
C5 C9 1.529(4) . ?
C5 C6 1.545(4) . ?
N3" C2" 1.317(4) . ?
N8" C7" 1.328(4) . ?
N8" C9" 1.339(4) . ?
C9 C1 1.521(4) . ?
N1' C2' 1.321(4) . ?
N1' C10' 1.361(4) . ?
C1 C2 1.509(4) . ?
C1 C12 1.523(4) . ?
C1 C8 1.536(4) . ?
N5" C5" 1.331(4) . ?
C8 C7 1.535(4) . ?
C9' C8' 1.358(4) . ?
C9' C10' 1.428(4) . ?
C13 C7 1.534(4) . ?
C5" N6" 1.341(4) . ?
C10' C5' 1.411(4) . ?
C6 C7 1.538(4) . ?
N6" C7" 1.337(4) . ?
C8' C7' 1.405(5) . ?
C7 C10 1.542(5) . ?
C5' C6' 1.391(5) . ?
C5' C4' 1.417(5) . ?
C4' C3' 1.339(5) . ?
C10" C11" 1.476(5) . ?
C3' C2' 1.390(5) . ?
C6' C7' 1.358(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
C4 N3 C2 127.1(2) . . ?
C13 N14 C9' 129.3(3) . . ?
C2" N1" C9" 106.1(2) . . ?
C2" N1" C10" 126.5(2) . . ?
C9" N1" C10" 127.5(3) . . ?
C9" C4" N3" 110.7(2) . . ?
C9" C4" C5" 117.3(3) . . ?
N3" C4" C5" 132.0(3) . . ?
C4 C5 C11 109.8(2) . . ?
C4 C5 C9 108.5(2) . . ?
C11 C5 C9 111.8(3) . . ?
C4 C5 C6 109.5(3) . . ?
C11 C5 C6 108.7(3) . . ?
C9 C5 C6 108.6(2) . . ?
C2" N3" C4" 103.8(2) . . ?
C7" N8" C9" 109.7(3) . . ?
N8" C9" N1" 127.0(3) . . ?
N8" C9" C4" 127.0(3) . . ?
N1" C9" C4" 106.0(3) . . ?
C1 C9 C5 110.7(2) . . ?
C2' N1' C10' 116.7(3) . . ?
C2 C1 C9 109.1(2) . . ?
C2 C1 C12 109.5(2) . . ?
C9 C1 C12 110.9(3) . . ?
C2 C1 C8 108.8(2) . . ?
C9 C1 C8 109.1(2) . . ?
C12 C1 C8 109.5(2) . . ?
O2 C2 N3 119.1(3) . . ?
O2 C2 C1 123.9(2) . . ?
N3 C2 C1 117.0(2) . . ?
C1 C8 C7 116.5(2) . . ?
O4 C4 N3 119.1(3) . . ?
O4 C4 C5 123.4(3) . . ?
N3 C4 C5 117.5(2) . . ?
C8' C9' N14 126.0(3) . . ?
C8' C9' C10' 119.5(3) . . ?
N14 C9' C10' 114.5(3) . . ?
O13 C13 N14 121.7(3) . . ?
O13 C13 C7 121.5(3) . . ?
N14 C13 C7 116.6(3) . . ?
N5" C5" N6" 118.9(3) . . ?
N5" C5" C4" 123.1(3) . . ?
N6" C5" C4" 118.1(3) . . ?
N1' C10' C5' 123.4(3) . . ?
N1' C10' C9' 117.5(3) . . ?
C5' C10' C9' 119.1(3) . . ?
C7 C6 C5 116.5(2) . . ?
C7" N6" C5" 117.5(3) . . ?
N3" C2" N1" 113.4(3) . . ?
C9' C8' C7' 120.1(3) . . ?
C13 C7 C8 109.8(2) . . ?
C13 C7 C6 115.9(2) . . ?
C8 C7 C6 108.7(3) . . ?
C13 C7 C10 104.3(3) . . ?
C8 C7 C10 108.6(2) . . ?
C6 C7 C10 109.2(3) . . ?
C6' C5' C10' 119.9(3) . . ?
C6' C5' C4' 123.8(3) . . ?
C10' C5' C4' 116.3(3) . . ?
C3' C4' C5' 120.1(3) . . ?
N1" C10" C11" 111.7(3) . . ?
C4' C3' C2' 119.3(3) . . ?
N8" C7" N6" 130.6(3) . . ?
C7' C6' C5' 119.7(3) . . ?
C6' C7' C8' 121.6(3) . . ?
N1' C2' C3' 124.2(3) . . ?
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.042
#====END

data_compound4
_database_code_depnum_ccdc_archive 'CCDC 224119'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C25 H34 Cl2 N2 O7'
_chemical_formula_weight         545.44
_chemical_melting_point          ?
_chemical_compound_source        ?

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   15.631(8)
_cell_length_b                   16.523(11)
_cell_length_c                   11.782(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.05(4)
_cell_angle_gamma                90.00
_cell_volume                     2778.9(27)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .09
_exptl_crystal_size_mid          .07
_exptl_crystal_size_min          .06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'PICKER 4-circle Stoe upgrade'
_diffrn_measurement_method       ' \w scans'
_diffrn_standards_number         1
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1278
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         47.52
_reflns_number_total             1278
_reflns_number_observed          692
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'PICKER STOE DIF4'
_computing_cell_refinement       'STOE DIF4'
_computing_data_reduction        'STOE REDU4'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELXLTL-Plus
_computing_publication_material  SHELXL-93

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.1477P)^2^+3.6548P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1278
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_obs          0.0834
_refine_ls_wR_factor_all         0.2555
_refine_ls_wR_factor_obs         0.2082
_refine_ls_goodness_of_fit_all   1.062
_refine_ls_goodness_of_fit_obs   1.238
_refine_ls_restrained_S_all      1.062
_refine_ls_restrained_S_obs      1.238
_refine_ls_shift/esd_max         -0.038
_refine_ls_shift/esd_mean        0.005

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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N7 N 0.2353(5) 0.1470(4) 0.4213(6) 0.057(2) Uani 1 d . .
H7A H 0.2342(5) 0.1701(4) 0.4900(6) 0.086 Uiso 1 d R .
O1 O 0.0000 0.1589(5) 0.2500 0.059(2) Uani 1 d S .
O8 O 0.3027(5) 0.2601(4) 0.3929(6) 0.073(2) Uani 1 d . .
C11 C 0.1836(6) 0.1794(5) 0.1281(8) 0.056(3) Uani 1 d . .
H11A H 0.1882(6) 0.1619(5) 0.0531(8) 0.084 Uiso 1 d R .
H11B H 0.1790(6) 0.2373(5) 0.1255(8) 0.084 Uiso 1 d R .
O2 O 0.0841(5) 0.2658(5) 0.2410(7) 0.083(2) Uani 1 d . .
C6 C 0.1971(6) 0.0697(5) 0.3927(8) 0.056(2) Uani 1 d . .
C10 C 0.2787(6) 0.0638(5) 0.2523(7) 0.054(2) Uani 1 d . .
H10A H 0.3359(6) 0.0497(5) 0.3212(7) 0.081 Uiso 1 d R .
H10B H 0.2792(6) 0.0393(5) 0.1788(7) 0.081 Uiso 1 d R .
C14 C 0.3588(6) 0.1895(5) 0.2184(9) 0.072(3) Uani 1 d . .
H14A H 0.3530(6) 0.2472(5) 0.2089(9) 0.108 Uiso 1 d R .
H14B H 0.4152(6) 0.1765(5) 0.2893(9) 0.108 Uiso 1 d R .
H14C H 0.3612(6) 0.1660(5) 0.1452(9) 0.108 Uiso 1 d R .
C8 C 0.2737(6) 0.1930(6) 0.3552(8) 0.054(3) Uani 1 d . .
O6 O 0.1663(5) 0.0377(4) 0.4610(6) 0.073(2) Uani 1 d . .
C2 C 0.0616(7) 0.1968(6) 0.2114(9) 0.063(3) Uani 1 d . .
C9 C 0.2737(6) 0.1570(5) 0.2381(8) 0.051(2) Uani 1 d . .
C13 C 0.1996(8) -0.0601(5) 0.2884(9) 0.080(3) Uani 1 d . .
H13A H 0.2566(8) -0.0760(5) 0.3563(9) 0.119 Uiso 1 d R .
H13B H 0.1469(8) -0.0778(5) 0.3041(9) 0.119 Uiso 1 d R .
H13C H 0.1968(8) -0.0843(5) 0.2129(9) 0.119 Uiso 1 d R .
C5 C 0.1965(6) 0.0315(5) 0.2762(8) 0.052(2) Uani 1 d . .
C4 C 0.1058(6) 0.0565(5) 0.1670(8) 0.057(3) Uani 1 d . .
H4A H 0.0544(6) 0.0410(5) 0.1872(8) 0.086 Uiso 1 d R .
H4B H 0.1006(6) 0.0254(5) 0.0957(8) 0.086 Uiso 1 d R .
C3 C 0.0919(6) 0.1456(5) 0.1294(7) 0.050(2) Uani 1 d . .
C12 C 0.0136(7) 0.1549(6) -0.0004(9) 0.081(3) Uani 1 d . .
H12A H -0.0437(7) 0.1334(6) -0.0013(9) 0.121 Uiso 1 d R .
H12B H 0.0056(7) 0.2113(6) -0.0214(9) 0.121 Uiso 1 d R .
H12C H 0.0298(7) 0.1263(6) -0.0598(9) 0.121 Uiso 1 d R .
Cl Cl 0.4571(4) -0.0112(4) 0.1195(6) 0.214(3) Uani 1 d . .
C C 0.5000 -0.0725(17) 0.2500 0.274(20) Uani 1 d S .
H0A H 0.5492 -0.1065(17) 0.2478 0.412 Uiso 1 d 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
N7 0.080(6) 0.058(5) 0.042(4) -0.013(4) 0.033(4) -0.015(4)
O1 0.070(6) 0.048(5) 0.078(6) 0.000 0.048(5) 0.000
O8 0.095(5) 0.057(4) 0.086(5) -0.024(4) 0.057(4) -0.025(4)
C11 0.064(7) 0.057(6) 0.053(6) 0.001(4) 0.029(6) 0.003(5)
O2 0.092(6) 0.059(5) 0.132(6) -0.003(4) 0.080(5) 0.004(4)
C6 0.061(7) 0.053(7) 0.058(7) -0.004(5) 0.030(6) 0.000(5)
C10 0.052(6) 0.066(6) 0.047(5) -0.009(5) 0.023(5) 0.005(5)
C14 0.070(7) 0.072(7) 0.098(8) -0.024(6) 0.058(7) -0.024(5)
C8 0.061(7) 0.057(7) 0.050(6) -0.003(5) 0.028(5) -0.003(5)
O6 0.107(6) 0.062(4) 0.068(4) 0.003(3) 0.053(4) -0.013(4)
C2 0.065(7) 0.044(6) 0.088(8) 0.006(6) 0.041(6) 0.009(5)
C9 0.057(6) 0.047(6) 0.058(6) -0.003(5) 0.034(5) -0.011(5)
C13 0.126(10) 0.045(6) 0.083(7) -0.001(5) 0.058(7) 0.000(6)
C5 0.058(6) 0.049(6) 0.054(6) 0.002(5) 0.026(5) -0.004(5)
C4 0.067(7) 0.063(6) 0.057(6) -0.013(5) 0.041(6) -0.006(5)
C3 0.052(6) 0.053(6) 0.049(6) 0.009(5) 0.025(5) 0.006(5)
C12 0.080(8) 0.090(8) 0.073(7) 0.018(6) 0.032(6) 0.011(6)
Cl 0.177(5) 0.268(7) 0.206(5) -0.057(5) 0.089(4) -0.050(5)
C 0.537(70) 0.157(27) 0.193(29) 0.000 0.215(39) 0.000

_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
N7 C8 1.388(10) . ?
N7 C6 1.392(10) . ?
O1 C2 1.372(10) . ?
O1 C2 1.372(10) 2 ?
O8 C8 1.211(9) . ?
C11 C9 1.520(12) . ?
C11 C3 1.544(12) . ?
O2 C2 1.203(10) . ?
C6 O6 1.213(9) . ?
C6 C5 1.508(12) . ?
C10 C5 1.520(11) . ?
C10 C9 1.548(11) . ?
C14 C9 1.538(11) . ?
C8 C9 1.502(11) . ?
C2 C3 1.499(12) . ?
C13 C5 1.518(11) . ?
C5 C4 1.533(11) . ?
C4 C3 1.526(11) . ?
C3 C12 1.528(12) . ?
Cl C 1.73(2) . ?
C Cl 1.73(2) 2_655 ?

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
C8 N7 C6 127.4(7) . . ?
C2 O1 C2 125.7(10) . 2 ?
C9 C11 C3 116.4(7) . . ?
O6 C6 N7 119.0(8) . . ?
O6 C6 C5 124.3(8) . . ?
N7 C6 C5 116.6(8) . . ?
C5 C10 C9 111.2(7) . . ?
O8 C8 N7 118.6(8) . . ?
O8 C8 C9 124.0(8) . . ?
N7 C8 C9 117.4(8) . . ?
O2 C2 O1 119.9(9) . . ?
O2 C2 C3 126.2(9) . . ?
O1 C2 C3 113.9(8) . . ?
C8 C9 C11 109.9(7) . . ?
C8 C9 C14 109.0(7) . . ?
C11 C9 C14 110.2(7) . . ?
C8 C9 C10 108.2(7) . . ?
C11 C9 C10 108.8(7) . . ?
C14 C9 C10 110.8(7) . . ?
C6 C5 C13 110.0(7) . . ?
C6 C5 C10 109.2(7) . . ?
C13 C5 C10 111.8(7) . . ?
C6 C5 C4 108.2(7) . . ?
C13 C5 C4 109.4(7) . . ?
C10 C5 C4 108.2(7) . . ?
C3 C4 C5 118.5(7) . . ?
C2 C3 C12 104.7(7) . . ?
C2 C3 C4 113.7(7) . . ?
C12 C3 C4 110.4(7) . . ?
C2 C3 C11 109.9(7) . . ?
C12 C3 C11 108.8(7) . . ?
C4 C3 C11 109.2(7) . . ?
Cl C Cl 108.4(16) 2_655 . ?

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
C2 O1 C2 C3 -157.1(8) 2 . . . ?
O1 C2 C3 C4 -37.6(10) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070