# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Kumar Biradha'
_publ_contact_author_email       KBIRADHA@CHEM.IITKGP.ERNET.IN

_publ_section_title              
;
Stepwise Dimerization of Double [2+2] reaction in the
Co-crystals of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one and
Phloroglucinol: A Single Crystal to Single Crystal Transformation
;
loop_
_publ_author_name
'Kumar Biradha'
'Ramkinkar Santra'

data_1
_database_code_depnum_ccdc_archive 'CCDC 688730'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.1243(4)
_cell_length_b                   15.3477(7)
_cell_length_c                   10.0546(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.0370(10)
_cell_angle_gamma                90.00
_cell_volume                     1216.26(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-APEX-2 CCD area detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16461
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.00
_reflns_number_total             2932
_reflns_number_gt                2089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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)+(0.0672P)²+0.1537P] 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_number_reflns         2932
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_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
N11 N -0.19182(17) 0.07310(10) 0.55406(13) 0.0739(4) Uani 1 1 d . . .
C11 C -0.1683(2) 0.14889(11) 0.61959(17) 0.0684(4) Uani 1 1 d . . .
H11 H -0.2268 0.1971 0.5757 0.082 Uiso 1 1 calc R . .
C12 C -0.06386(17) 0.16098(9) 0.74751(15) 0.0575(4) Uani 1 1 d . . .
H12 H -0.0526 0.2160 0.7876 0.069 Uiso 1 1 calc R . .
C13 C 0.02499(15) 0.09074(8) 0.81685(13) 0.0486(3) Uani 1 1 d . . .
C14 C 0.00234(18) 0.01176(9) 0.74938(15) 0.0568(3) Uani 1 1 d . . .
H14 H 0.0589 -0.0376 0.7908 0.068 Uiso 1 1 calc R . .
C15 C -0.1038(2) 0.00634(11) 0.62108(16) 0.0677(4) Uani 1 1 d . . .
H15 H -0.1153 -0.0476 0.5776 0.081 Uiso 1 1 calc R . .
C16 C 0.13525(17) 0.10233(8) 0.95491(14) 0.0527(3) Uani 1 1 d . . .
H16 H 0.1261 0.1549 0.9984 0.063 Uiso 1 1 calc R . .
N21 N 0.75924(16) -0.29953(8) 1.40153(12) 0.0643(3) Uani 1 1 d . . .
C21 C 0.71400(19) -0.23288(11) 1.46978(14) 0.0635(4) Uani 1 1 d . . .
H21 H 0.7470 -0.2343 1.5650 0.076 Uiso 1 1 calc R . .
C22 C 0.62177(17) -0.16195(9) 1.40903(13) 0.0551(3) Uani 1 1 d . . .
H22 H 0.5940 -0.1173 1.4622 0.066 Uiso 1 1 calc R . .
C23 C 0.57072(14) -0.15840(8) 1.26623(12) 0.0451(3) Uani 1 1 d . . .
C24 C 0.61543(16) -0.22785(8) 1.19529(12) 0.0484(3) Uani 1 1 d . . .
H24 H 0.5820 -0.2291 1.1001 0.058 Uiso 1 1 calc R . .
C25 C 0.70963(17) -0.29519(9) 1.26573(14) 0.0562(3) Uani 1 1 d . . .
H25 H 0.7404 -0.3404 1.2152 0.067 Uiso 1 1 calc R . .
C26 C 0.47053(15) -0.08662(8) 1.19091(12) 0.0474(3) Uani 1 1 d . . .
H26 H 0.4095 -0.0983 1.1018 0.057 Uiso 1 1 calc R . .
O32 O 0.34614(16) 0.13314(6) 1.21846(12) 0.0771(3) Uani 1 1 d . . .
C31 C 0.24521(17) 0.04594(8) 1.02290(13) 0.0520(3) Uani 1 1 d . . .
H31 H 0.2577 -0.0071 0.9816 0.062 Uiso 1 1 calc R . .
C32 C 0.35019(17) 0.06299(8) 1.16242(13) 0.0515(3) Uani 1 1 d . . .
C33 C 0.45863(17) -0.00688(8) 1.23757(13) 0.0528(3) Uani 1 1 d . . .
H33 H 0.5239 0.0062 1.3248 0.063 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
N11 C11 1.328(2) . ?
N11 C15 1.335(2) . ?
C11 C12 1.371(2) . ?
C12 C13 1.3875(17) . ?
C13 C14 1.3795(18) . ?
C13 C16 1.4689(19) . ?
C14 C15 1.369(2) . ?
C16 C31 1.3108(18) . ?
N21 C25 1.3283(18) . ?
N21 C21 1.332(2) . ?
C21 C22 1.3776(19) . ?
C22 C23 1.3956(17) . ?
C23 C24 1.3793(17) . ?
C23 C26 1.4664(16) . ?
C24 C25 1.3757(17) . ?
C26 C33 1.3226(17) . ?
O32 C32 1.2193(15) . ?
C31 C32 1.4777(19) . ?
C32 C33 1.4745(18) . ?

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
C11 N11 C15 115.29(14) . . ?
N11 C11 C12 124.46(14) . . ?
C11 C12 C13 119.63(14) . . ?
C14 C13 C12 116.39(13) . . ?
C14 C13 C16 123.31(12) . . ?
C12 C13 C16 120.29(12) . . ?
C15 C14 C13 119.67(13) . . ?
N11 C15 C14 124.53(15) . . ?
C31 C16 C13 126.53(13) . . ?
C25 N21 C21 115.99(12) . . ?
N21 C21 C22 124.52(13) . . ?
C21 C22 C23 118.76(13) . . ?
C24 C23 C22 116.87(11) . . ?
C24 C23 C26 119.76(11) . . ?
C22 C23 C26 123.36(12) . . ?
C25 C24 C23 119.85(12) . . ?
N21 C25 C24 123.99(13) . . ?
C33 C26 C23 126.24(11) . . ?
C16 C31 C32 122.80(12) . . ?
O32 C32 C33 119.02(12) . . ?
O32 C32 C31 121.40(12) . . ?
C33 C32 C31 119.55(11) . . ?
C26 C33 C32 125.25(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041

data_2
_database_code_depnum_ccdc_archive 'CCDC 688731'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.543(4)
_cell_length_b                   21.387(9)
_cell_length_c                   8.802(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.868(13)
_cell_angle_gamma                90.00
_cell_volume                     1790.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3912
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.16

_exptl_crystal_description       blocks
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-APEX-2 CCD area detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23691
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.16
_reflns_number_total             3912
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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)+(0.0567P)²+0.2049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.76694(13) 0.02859(6) 0.05457(15) 0.0769(4) Uani 1 1 d . . .
C1 C -0.74622(16) 0.06507(8) 0.16073(19) 0.0521(4) Uani 1 1 d . . .
C2 C -0.85144(15) 0.07507(7) 0.27238(18) 0.0525(4) Uani 1 1 d . . .
H2 H -0.8296 0.1027 0.3525 0.063 Uiso 1 1 calc R . .
C3 C -0.97463(15) 0.04680(7) 0.26399(18) 0.0487(4) Uani 1 1 d . . .
H3 H -0.9938 0.0191 0.1834 0.058 Uiso 1 1 calc R . .
C4 C -0.61742(16) 0.10271(8) 0.18400(19) 0.0562(4) Uani 1 1 d . . .
H4 H -0.6113 0.1315 0.2635 0.067 Uiso 1 1 calc R . .
C5 C -0.51004(15) 0.09846(7) 0.09991(17) 0.0520(4) Uani 1 1 d . . .
H5 H -0.5160 0.0686 0.0228 0.062 Uiso 1 1 calc R . .
N11 N -1.29881(13) 0.06846(7) 0.56525(16) 0.0580(4) Uani 1 1 d . . .
C11 C -1.17733(18) 0.09844(9) 0.5890(2) 0.0646(5) Uani 1 1 d . . .
H11 H -1.1646 0.1246 0.6735 0.077 Uiso 1 1 calc R . .
C12 C -1.06918(16) 0.09327(8) 0.49619(19) 0.0595(4) Uani 1 1 d . . .
H12 H -0.9862 0.1155 0.5184 0.071 Uiso 1 1 calc R . .
C13 C -1.08453(14) 0.05473(7) 0.36938(17) 0.0453(4) Uani 1 1 d . . .
C14 C -1.21057(15) 0.02322(7) 0.34478(18) 0.0527(4) Uani 1 1 d . . .
H14 H -1.2263 -0.0035 0.2617 0.063 Uiso 1 1 calc R . .
C15 C -1.31307(16) 0.03159(8) 0.4442(2) 0.0585(4) Uani 1 1 d . . .
H15 H -1.3973 0.0100 0.4250 0.070 Uiso 1 1 calc R . .
N21 N -0.13353(14) 0.20755(7) 0.15006(18) 0.0669(4) Uani 1 1 d . . .
C21 C -0.2416(2) 0.21903(9) 0.2321(2) 0.0729(5) Uani 1 1 d . . .
H21 H -0.2327 0.2514 0.3028 0.087 Uiso 1 1 calc R . .
C22 C -0.36546(17) 0.18592(8) 0.2185(2) 0.0630(5) Uani 1 1 d . . .
H22 H -0.4381 0.1967 0.2775 0.076 Uiso 1 1 calc R . .
C23 C -0.38182(15) 0.13662(7) 0.11699(17) 0.0487(4) Uani 1 1 d . . .
C24 C -0.26948(16) 0.12454(8) 0.03134(18) 0.0557(4) Uani 1 1 d . . .
H24 H -0.2748 0.0921 -0.0393 0.067 Uiso 1 1 calc R . .
C25 C -0.14972(17) 0.16078(9) 0.0513(2) 0.0612(4) Uani 1 1 d . . .
H25 H -0.0761 0.1519 -0.0080 0.073 Uiso 1 1 calc R . .
O1A O 0.05679(12) 0.29812(6) 0.25435(15) 0.0654(3) Uani 1 1 d . . .
O2A O 0.47616(12) 0.41236(5) 0.23583(13) 0.0590(3) Uani 1 1 d . . .
C1A C 0.18271(15) 0.30395(7) 0.19387(18) 0.0490(4) Uani 1 1 d . . .
C2A C 0.26774(15) 0.35360(7) 0.24346(17) 0.0484(4) Uani 1 1 d . . .
H2A H 0.2382 0.3812 0.3159 0.058 Uiso 1 1 calc R . .
C3A C 0.39704(15) 0.36228(7) 0.18532(16) 0.0447(3) Uani 1 1 d . . .
C4A C 0.44157(16) 0.32063(8) 0.07961(18) 0.0577(4) Uani 1 1 d . . .
H4A H 0.5290 0.3255 0.0418 0.069 Uiso 1 1 calc R . .
C5A C 0.35522(19) 0.27177(9) 0.0307(2) 0.0697(5) Uani 1 1 d . . .
H5A H 0.3850 0.2440 -0.0412 0.084 Uiso 1 1 calc R . .
C6A C 0.22566(18) 0.26307(8) 0.0858(2) 0.0613(4) Uani 1 1 d . . .
H6A H 0.1681 0.2301 0.0507 0.074 Uiso 1 1 calc R . .
H2AO H 0.555(2) 0.4168(9) 0.182(2) 0.094(7) Uiso 1 1 d . . .
H1AO H 0.010(3) 0.2639(12) 0.211(3) 0.122(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2204(19) . ?
C1 C4 1.469(2) . ?
C1 C2 1.479(2) . ?
C2 C3 1.318(2) . ?
C3 C13 1.468(2) . ?
C4 C5 1.317(2) . ?
C5 C23 1.468(2) . ?
N11 C15 1.324(2) . ?
N11 C11 1.326(2) . ?
C11 C12 1.374(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.380(2) . ?
C14 C15 1.378(2) . ?
N21 C25 1.326(2) . ?
N21 C21 1.331(2) . ?
C21 C22 1.375(2) . ?
C22 C23 1.382(2) . ?
C23 C24 1.386(2) . ?
C24 C25 1.380(2) . ?
O1A C1A 1.3607(18) . ?
O2A C3A 1.3631(18) . ?
C1A C6A 1.379(2) . ?
C1A C2A 1.384(2) . ?
C2A C3A 1.388(2) . ?
C3A C4A 1.381(2) . ?
C4A C5A 1.377(2) . ?
C5A C6A 1.379(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 122.44(14) . . ?
O1 C1 C2 121.74(14) . . ?
C4 C1 C2 115.81(14) . . ?
C3 C2 C1 123.30(15) . . ?
C2 C3 C13 126.39(15) . . ?
C5 C4 C1 124.43(16) . . ?
C4 C5 C23 125.85(15) . . ?
C15 N11 C11 116.34(14) . . ?
N11 C11 C12 123.96(16) . . ?
C11 C12 C13 119.56(15) . . ?
C14 C13 C12 116.64(13) . . ?
C14 C13 C3 120.30(14) . . ?
C12 C13 C3 123.06(13) . . ?
C15 C14 C13 119.55(15) . . ?
N11 C15 C14 123.96(15) . . ?
C25 N21 C21 116.25(14) . . ?
N21 C21 C22 123.93(18) . . ?
C21 C22 C23 119.89(16) . . ?
C22 C23 C24 116.32(14) . . ?
C22 C23 C5 122.53(14) . . ?
C24 C23 C5 121.15(15) . . ?
C25 C24 C23 119.77(16) . . ?
N21 C25 C24 123.83(15) . . ?
O1A C1A C6A 122.38(14) . . ?
O1A C1A C2A 117.42(14) . . ?
C6A C1A C2A 120.20(14) . . ?
C1A C2A C3A 120.14(14) . . ?
O2A C3A C4A 122.21(13) . . ?
O2A C3A C2A 118.04(13) . . ?
C4A C3A C2A 119.75(14) . . ?
C5A C4A C3A 119.33(15) . . ?
C4A C5A C6A 121.56(16) . . ?
C5A C6A C1A 119.00(15) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032

data_3
_database_code_depnum_ccdc_archive 'CCDC 688732'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N3 O4'
_chemical_formula_weight         403.43

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   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                   15.7801(13)
_cell_length_b                   13.6092(11)
_cell_length_c                   19.7644(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.767(3)
_cell_angle_gamma                90.00
_cell_volume                     4242.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4169
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      26.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER-APEX-2 CCD area detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26692
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4169
_reflns_number_gt                2160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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.
To correct the Hirshfeld test differences of C-C bonds of C33-C36, N21-C25
and C10-C11 three following restraints
were applied.
DELU 0.002 0.002 C33 C36
DELU 0.003 0.003 N21 C25
DELU 0.003 0.003 C10 C11

;

_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)+(0.0748P)²+0.4044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4169
_refine_ls_number_parameters     283
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.17441(11) 0.35003(18) 0.13601(9) 0.0946(7) Uani 1 1 d . . .
O3 O 0.02158(13) 0.33991(16) -0.04353(9) 0.0878(6) Uani 1 1 d . . .
O5 O 0.09355(12) 0.20917(14) 0.17371(9) 0.0726(5) Uani 1 1 d . . .
C1 C -0.09797(13) 0.32636(19) 0.11088(11) 0.0630(7) Uani 1 1 d . . .
C2 C -0.07805(14) 0.34810(18) 0.04508(11) 0.0638(7) Uani 1 1 d . . .
H2 H -0.1171 0.3802 0.0167 0.077 Uiso 1 1 calc R . .
C3 C 0.00020(14) 0.32186(18) 0.02159(11) 0.0602(6) Uani 1 1 d . . .
C4 C 0.05885(14) 0.27528(17) 0.06370(11) 0.0598(6) Uani 1 1 d . . .
H4 H 0.1118 0.2579 0.0481 0.072 Uiso 1 1 calc R . .
C5 C 0.03747(13) 0.25513(17) 0.12910(11) 0.0556(6) Uani 1 1 d . . .
C6 C -0.04031(13) 0.27855(18) 0.15336(11) 0.0618(7) Uani 1 1 d . . .
H6 H -0.0540 0.2626 0.1975 0.074 Uiso 1 1 calc R . .
O10 O 0.57712(12) 0.32790(18) 0.17905(10) 0.0979(7) Uani 1 1 d . . .
C10 C 0.57254(15) 0.4171(3) 0.18051(13) 0.0710(7) Uani 1 1 d U . .
C11 C 0.63188(16) 0.4779(2) 0.22405(12) 0.0715(7) Uani 1 1 d U . .
H11 H 0.6188 0.5436 0.2311 0.086 Uiso 1 1 calc R . .
C12 C 0.51156(15) 0.4700(2) 0.13818(12) 0.0682(7) Uani 1 1 d . . .
H12 H 0.5141 0.5382 0.1380 0.082 Uiso 1 1 calc R . .
N21 N 0.27588(14) 0.5611(2) -0.03751(11) 0.0818(7) Uani 1 1 d U . .
C21 C 0.34259(17) 0.6089(2) -0.01324(14) 0.0798(8) Uani 1 1 d . . .
H21 H 0.3507 0.6731 -0.0278 0.096 Uiso 1 1 calc R . .
C22 C 0.40079(15) 0.5702(2) 0.03215(12) 0.0706(7) Uani 1 1 d . . .
H22 H 0.4464 0.6080 0.0478 0.085 Uiso 1 1 calc R . .
C23 C 0.39156(14) 0.4750(2) 0.05448(12) 0.0603(6) Uani 1 1 d . . .
C24 C 0.32049(16) 0.4251(2) 0.03073(14) 0.0808(8) Uani 1 1 d . . .
H24 H 0.3104 0.3611 0.0449 0.097 Uiso 1 1 calc R . .
C25 C 0.26497(18) 0.4706(3) -0.01392(16) 0.0922(9) Uani 1 1 d U . .
H25 H 0.2169 0.4362 -0.0285 0.111 Uiso 1 1 calc R . .
C26 C 0.45297(14) 0.4273(2) 0.10012(12) 0.0662(7) Uani 1 1 d . . .
H26 H 0.4503 0.3592 0.1025 0.079 Uiso 1 1 calc R . .
N31 N 0.88488(15) 0.58717(19) 0.37768(10) 0.0730(6) Uani 1 1 d . . .
C31 C 0.89568(17) 0.4986(2) 0.35297(14) 0.0808(8) Uani 1 1 d . . .
H31 H 0.9460 0.4662 0.3642 0.097 Uiso 1 1 calc R . .
C32 C 0.83769(17) 0.4509(2) 0.31182(14) 0.0770(7) Uani 1 1 d . . .
H32 H 0.8496 0.3886 0.2952 0.092 Uiso 1 1 calc R . .
C33 C 0.76213(15) 0.49548(19) 0.29524(11) 0.0622(6) Uani 1 1 d U . .
C34 C 0.74880(16) 0.5892(2) 0.32131(12) 0.0700(7) Uani 1 1 d . . .
H34 H 0.6985 0.6227 0.3116 0.084 Uiso 1 1 calc R . .
C35 C 0.81175(18) 0.6312(2) 0.36187(12) 0.0751(8) Uani 1 1 d . . .
H35 H 0.8025 0.6938 0.3791 0.090 Uiso 1 1 calc R . .
C36 C 0.69974(15) 0.4431(2) 0.25191(12) 0.0709(7) Uani 1 1 d U . .
H36 H 0.7109 0.3771 0.2438 0.085 Uiso 1 1 calc R . .
N100 N 0.26677(16) 0.2036(2) 0.14123(14) 0.1088(9) Uani 1 1 d . . .
C100 C 0.32963(17) 0.1825(2) 0.16410(14) 0.0785(8) Uani 1 1 d . . .
C101 C 0.40955(16) 0.1550(3) 0.19418(14) 0.1078(12) Uani 1 1 d . . .
H10A H 0.4540 0.1905 0.1728 0.162 Uiso 1 1 calc R . .
H10B H 0.4181 0.0857 0.1883 0.162 Uiso 1 1 calc R . .
H10C H 0.4102 0.1703 0.2416 0.162 Uiso 1 1 calc R . .
H5O H 0.140(2) 0.210(2) 0.1554(15) 0.107(12) Uiso 1 1 d . . .
H3O H -0.0245(18) 0.361(2) -0.0644(15) 0.098(10) Uiso 1 1 d . . .
H1O H -0.206(2) 0.379(3) 0.1028(18) 0.135(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.357(3) . ?
O3 C3 1.363(3) . ?
O5 C5 1.380(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.369(3) . ?
O10 C10 1.217(3) . ?
C10 C12 1.447(4) . ?
C10 C11 1.500(4) . ?
C11 C36 1.279(3) . ?
C12 C26 1.309(3) . ?
N21 C21 1.315(3) . ?
N21 C25 1.330(4) . ?
C21 C22 1.369(3) . ?
C22 C23 1.377(3) . ?
C23 C24 1.381(3) . ?
C23 C26 1.456(3) . ?
C24 C25 1.372(4) . ?
N31 C31 1.313(3) . ?
N31 C35 1.329(3) . ?
C31 C32 1.369(3) . ?
C32 C33 1.368(3) . ?
C33 C34 1.394(3) . ?
C33 C36 1.469(3) . ?
C34 C35 1.381(3) . ?
N100 C100 1.115(3) . ?
C100 C101 1.428(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.7(2) . . ?
O1 C1 C6 117.7(2) . . ?
C2 C1 C6 120.6(2) . . ?
C1 C2 C3 119.6(2) . . ?
O3 C3 C4 118.1(2) . . ?
O3 C3 C2 121.4(2) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 118.7(2) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 O5 116.5(2) . . ?
C4 C5 O5 121.4(2) . . ?
C5 C6 C1 118.5(2) . . ?
O10 C10 C12 121.4(3) . . ?
O10 C10 C11 121.8(2) . . ?
C12 C10 C11 116.8(3) . . ?
C36 C11 C10 122.9(3) . . ?
C26 C12 C10 123.9(3) . . ?
C21 N21 C25 116.2(2) . . ?
N21 C21 C22 124.2(3) . . ?
C21 C22 C23 119.8(3) . . ?
C22 C23 C24 116.5(2) . . ?
C22 C23 C26 122.9(2) . . ?
C24 C23 C26 120.6(3) . . ?
C25 C24 C23 119.5(3) . . ?
N21 C25 C24 123.8(3) . . ?
C12 C26 C23 127.1(3) . . ?
C31 N31 C35 116.6(2) . . ?
N31 C31 C32 124.3(3) . . ?
C33 C32 C31 119.6(3) . . ?
C32 C33 C34 117.2(2) . . ?
C32 C33 C36 119.2(3) . . ?
C34 C33 C36 123.6(2) . . ?
C35 C34 C33 118.7(2) . . ?
N31 C35 C34 123.6(3) . . ?
C11 C36 C33 127.5(3) . . ?
N100 C100 C101 179.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032

data_4
_database_code_depnum_ccdc_archive 'CCDC 688733'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H42 N6 O8'
_chemical_formula_weight         806.86

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   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                   15.333(7)
_cell_length_b                   13.061(6)
_cell_length_c                   20.359(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.412(16)
_cell_angle_gamma                90.00
_cell_volume                     4077(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3205
_cell_measurement_theta_min      2
_cell_measurement_theta_max      24

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-APpex-2 CCD area Detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21363
_diffrn_reflns_av_R_equivalents  0.1465
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         24.00
_reflns_number_total             3205
_reflns_number_gt                1439
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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.

To correct the Hirshfeld test differences of C-O bonds of C1-O1
SIMU 0.005 0.005 C1 O1 has been applied.
Which created the following six restrains
SIMU U11 O1 C1
SIMU U22 O1 C1
SIMU U33 O1 C1
SIMU U23 O1 C1
SIMU U12 O1 C1

;

_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)+(0.1014P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     284
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9166(3) 0.3735(4) 0.6783(2) 0.1152(15) Uani 1 1 d U . .
C1 C 0.9440(3) 0.4516(5) 0.6998(3) 0.0695(14) Uani 1 1 d U . .
C2 C 0.9053(3) 0.5050(4) 0.7577(3) 0.0673(16) Uani 1 1 d . . .
H2 H 0.8900 0.5762 0.7477 0.081 Uiso 1 1 calc R . .
C3 C 0.8339(3) 0.4507(4) 0.7967(2) 0.0551(13) Uani 1 1 d . . .
H3 H 0.8164 0.3865 0.7754 0.066 Uiso 1 1 calc R . .
C4 C 0.9711(3) 0.4964(3) 0.8192(2) 0.0600(14) Uani 1 1 d . . .
H4 H 0.9789 0.5628 0.8409 0.072 Uiso 1 1 calc R . .
C5 C 0.9036(3) 0.4301(3) 0.8553(2) 0.0521(13) Uani 1 1 d . . .
H5 H 0.9221 0.3583 0.8544 0.063 Uiso 1 1 calc R . .
N11 N 0.6166(3) 0.6144(3) 0.87567(18) 0.0583(11) Uani 1 1 d . . .
C11 C 0.6120(3) 0.5163(4) 0.8594(2) 0.0609(14) Uani 1 1 d . . .
H11 H 0.5607 0.4813 0.8685 0.073 Uiso 1 1 calc R . .
C12 C 0.6787(3) 0.4631(4) 0.8300(2) 0.0569(13) Uani 1 1 d . . .
H12 H 0.6711 0.3948 0.8185 0.068 Uiso 1 1 calc R . .
C13 C 0.7562(3) 0.5111(3) 0.8175(2) 0.0444(11) Uani 1 1 d . . .
C14 C 0.7598(3) 0.6144(4) 0.8323(2) 0.0578(13) Uani 1 1 d . . .
H14 H 0.8101 0.6515 0.8232 0.069 Uiso 1 1 calc R . .
C15 C 0.6900(3) 0.6624(4) 0.8602(2) 0.0581(13) Uani 1 1 d . . .
H15 H 0.6941 0.7322 0.8687 0.070 Uiso 1 1 calc R . .
N21 N 0.7956(3) 0.5189(4) 1.0410(2) 0.0688(13) Uani 1 1 d . . .
C21 C 0.7706(4) 0.4358(5) 1.0093(3) 0.0739(16) Uani 1 1 d . . .
H21 H 0.7242 0.3984 1.0261 0.089 Uiso 1 1 calc R . .
C22 C 0.8091(3) 0.4015(4) 0.9528(2) 0.0643(14) Uani 1 1 d . . .
H22 H 0.7912 0.3398 0.9342 0.077 Uiso 1 1 calc R . .
C23 C 0.8738(3) 0.4575(4) 0.9234(2) 0.0489(12) Uani 1 1 d . . .
C24 C 0.9018(3) 0.5420(4) 0.9573(2) 0.0701(15) Uani 1 1 d . . .
H24 H 0.9477 0.5810 0.9414 0.084 Uiso 1 1 calc R . .
C25 C 0.8612(4) 0.5693(4) 1.0155(2) 0.0727(16) Uani 1 1 d . . .
H25 H 0.8818 0.6267 1.0378 0.087 Uiso 1 1 calc R . .
O1A O 0.4257(3) 0.2274(3) 0.67993(17) 0.0659(10) Uani 1 1 d . . .
O2A O 0.6887(2) 0.3945(3) 0.63516(16) 0.0714(11) Uani 1 1 d . . .
O3A O 0.4918(2) 0.3097(3) 0.45869(18) 0.0842(13) Uani 1 1 d . . .
C1A C 0.4804(3) 0.2693(3) 0.6337(2) 0.0494(12) Uani 1 1 d . . .
C2A C 0.5566(3) 0.3102(3) 0.6552(2) 0.0523(12) Uani 1 1 d . . .
H2A H 0.5707 0.3088 0.6997 0.063 Uiso 1 1 calc R . .
C3A C 0.6130(3) 0.3541(4) 0.6111(2) 0.0526(12) Uani 1 1 d . . .
C4A C 0.5923(3) 0.3555(4) 0.5441(2) 0.0578(13) Uani 1 1 d . . .
H4A H 0.6304 0.3848 0.5141 0.069 Uiso 1 1 calc R . .
C5A C 0.5158(3) 0.3134(4) 0.5233(2) 0.0587(13) Uani 1 1 d . . .
C6A C 0.4570(3) 0.2694(3) 0.5678(3) 0.0588(13) Uani 1 1 d . . .
H6A H 0.4044 0.2413 0.5535 0.071 Uiso 1 1 calc R . .
N100 N 0.7514(3) -0.1843(4) 0.3436(2) 0.0835(15) Uani 1 1 d . . .
C101 C 0.9031(4) -0.1218(5) 0.3105(3) 0.098(2) Uani 1 1 d . . .
H10A H 0.9453 -0.1471 0.3415 0.147 Uiso 1 1 calc R . .
H10B H 0.9043 -0.0483 0.3103 0.147 Uiso 1 1 calc R . .
H10C H 0.9167 -0.1469 0.2674 0.147 Uiso 1 1 calc R . .
C100 C 0.8167(4) -0.1567(4) 0.3289(2) 0.0612(14) Uani 1 1 d . . .
H1AO H 0.373(4) 0.200(4) 0.661(2) 0.09(2) Uiso 1 1 d . . .
H3AO H 0.534(4) 0.343(4) 0.429(3) 0.096(18) Uiso 1 1 d . . .
H2AO H 0.725(5) 0.436(6) 0.601(4) 0.18(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.186(6) . ?
C1 C4 1.482(7) 2_756 ?
C1 C2 1.495(7) . ?
C2 C3 1.532(6) . ?
C2 C4 1.607(7) . ?
C3 C13 1.493(6) . ?
C3 C5 1.619(7) . ?
C4 C1 1.482(7) 2_756 ?
C4 C5 1.540(6) . ?
C5 C23 1.506(6) . ?
N11 C11 1.325(6) . ?
N11 C15 1.329(5) . ?
C11 C12 1.377(6) . ?
C12 C13 1.368(6) . ?
C13 C14 1.383(6) . ?
C14 C15 1.368(6) . ?
N21 C25 1.313(6) . ?
N21 C21 1.319(6) . ?
C21 C22 1.372(6) . ?
C22 C23 1.374(6) . ?
C23 C24 1.369(7) . ?
C24 C25 1.389(6) . ?
O1A C1A 1.379(5) . ?
O2A C3A 1.362(5) . ?
O3A C5A 1.364(6) . ?
C1A C2A 1.355(6) . ?
C1A C6A 1.386(6) . ?
C2A C3A 1.377(6) . ?
C3A C4A 1.398(6) . ?
C4A C5A 1.359(6) . ?
C5A C6A 1.406(6) . ?
N100 C100 1.108(6) . ?
C101 C100 1.452(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 123.6(5) . 2_756 ?
O1 C1 C2 123.4(5) . . ?
C4 C1 C2 112.1(5) 2_756 . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 C4 109.4(4) . . ?
C3 C2 C4 90.6(4) . . ?
C13 C3 C2 118.5(4) . . ?
C13 C3 C5 113.7(4) . . ?
C2 C3 C5 89.3(4) . . ?
C1 C4 C5 119.8(4) 2_756 . ?
C1 C4 C2 111.8(4) 2_756 . ?
C5 C4 C2 89.5(4) . . ?
C23 C5 C4 121.0(4) . . ?
C23 C5 C3 115.8(4) . . ?
C4 C5 C3 89.9(3) . . ?
C11 N11 C15 116.1(4) . . ?
N11 C11 C12 124.0(5) . . ?
C13 C12 C11 119.9(5) . . ?
C12 C13 C14 116.1(4) . . ?
C12 C13 C3 120.4(4) . . ?
C14 C13 C3 123.1(4) . . ?
C15 C14 C13 120.5(5) . . ?
N11 C15 C14 123.3(5) . . ?
C25 N21 C21 116.1(4) . . ?
N21 C21 C22 123.7(5) . . ?
C21 C22 C23 120.5(5) . . ?
C24 C23 C22 115.8(4) . . ?
C24 C23 C5 124.1(4) . . ?
C22 C23 C5 119.9(4) . . ?
C23 C24 C25 119.8(5) . . ?
N21 C25 C24 123.9(5) . . ?
C2A C1A O1A 117.6(4) . . ?
C2A C1A C6A 122.0(4) . . ?
O1A C1A C6A 120.5(5) . . ?
C1A C2A C3A 119.9(4) . . ?
O2A C3A C2A 117.7(4) . . ?
O2A C3A C4A 122.2(4) . . ?
C2A C3A C4A 120.1(5) . . ?
C5A C4A C3A 119.2(4) . . ?
C4A C5A O3A 122.8(4) . . ?
C4A C5A C6A 121.4(5) . . ?
O3A C5A C6A 115.8(5) . . ?
C1A C6A C5A 117.4(5) . . ?
N100 C100 C101 179.0(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061

data_5
_database_code_depnum_ccdc_archive 'CCDC 688736'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H42 N6 O8'
_chemical_formula_weight         806.86

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   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                   15.415(3)
_cell_length_b                   13.170(3)
_cell_length_c                   20.423(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.224(6)
_cell_angle_gamma                90.00
_cell_volume                     4145.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3636
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-APEX-2 CCD area detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23872
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3636
_reflns_number_gt                1757
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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)+(0.0983P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.073
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0585(2) 0.5672(4) 0.6972(2) 0.0719(11) Uani 1 1 d . . .
O1 O 1.0727(2) 0.6548(3) 0.6869(2) 0.1516(17) Uani 1 1 d . A .
C2 C 1.1069(18) 0.5016(19) 0.7442(15) 0.122(12) Uani 0.411(8) 1 d P A 1
H2 H 1.0834 0.4443 0.7638 0.146 Uiso 0.411(8) 1 calc PR A 1
C3 C 1.1918(6) 0.5354(7) 0.7557(6) 0.059(3) Uani 0.411(8) 1 d P A 1
H3 H 1.2140 0.5864 0.7294 0.071 Uiso 0.411(8) 1 calc PR A 1
C4 C 1.0128(7) 0.5346(7) 0.6437(5) 0.059(3) Uani 0.411(8) 1 d P A 1
H4 H 1.0226 0.4676 0.6315 0.071 Uiso 0.411(8) 1 calc PR A 1
C5 C 0.9570(6) 0.5841(7) 0.6071(5) 0.058(3) Uani 0.411(8) 1 d P A 1
H5 H 0.9649 0.6540 0.6042 0.070 Uiso 0.411(8) 1 calc PR A 1
C2' C 1.1025(10) 0.5082(7) 0.7495(7) 0.064(5) Uani 0.589(8) 1 d P . 2
H2' H 1.1190 0.4394 0.7363 0.077 Uiso 0.589(8) 1 calc PR A 2
C3' C 1.1672(4) 0.5585(5) 0.7968(4) 0.0542(19) Uani 0.589(8) 1 d P . 2
H3' H 1.1849 0.6246 0.7796 0.065 Uiso 0.589(8) 1 calc PR A 2
C4' C 0.9674(4) 0.5119(5) 0.6842(4) 0.061(2) Uani 0.589(8) 1 d P . 2
H4' H 0.9750 0.4444 0.6649 0.073 Uiso 0.589(8) 1 calc PR A 2
C5' C 0.9007(4) 0.5740(4) 0.6457(3) 0.050(2) Uani 0.589(8) 1 d P . 2
H5' H 0.9195 0.6450 0.6462 0.060 Uiso 0.589(8) 1 calc PR A 2
C24 C 0.8136(3) 0.5938(3) 0.5426(2) 0.0817(12) Uani 1 1 d . A .
H24 H 0.7982 0.6561 0.5604 0.098 Uiso 1 1 calc R . .
C23 C 0.8817(3) 0.5408(3) 0.5696(2) 0.0928(15) Uani 1 1 d . . .
N11 N 1.3812(2) 0.3912(2) 0.87875(14) 0.0650(8) Uani 1 1 d . A .
C11 C 1.3880(2) 0.4868(3) 0.86152(18) 0.0655(10) Uani 1 1 d . . .
H11 H 1.4384 0.5215 0.8736 0.079 Uiso 1 1 calc R . .
C12 C 1.3253(2) 0.5379(3) 0.82693(18) 0.0687(11) Uani 1 1 d . A .
H12 H 1.3345 0.6050 0.8147 0.082 Uiso 1 1 calc R . .
C13 C 1.2487(2) 0.4908(3) 0.81016(18) 0.0644(10) Uani 1 1 d . . .
C14 C 1.2417(2) 0.3901(3) 0.82681(17) 0.0634(10) Uani 1 1 d . A .
H14 H 1.1919 0.3537 0.8155 0.076 Uiso 1 1 calc R . .
C15 C 1.3087(3) 0.3438(3) 0.86013(18) 0.0693(10) Uani 1 1 d . . .
H15 H 1.3033 0.2753 0.8703 0.083 Uiso 1 1 calc R A .
N21 N 0.7884(2) 0.4711(3) 0.46088(15) 0.0766(9) Uani 1 1 d . A .
C21 C 0.8553(3) 0.4212(3) 0.4860(2) 0.0887(13) Uani 1 1 d . . .
H21 H 0.8715 0.3607 0.4662 0.106 Uiso 1 1 calc R A .
C22 C 0.9025(3) 0.4536(3) 0.5399(2) 0.0974(15) Uani 1 1 d . A .
H22 H 0.9490 0.4151 0.5557 0.117 Uiso 1 1 calc R . .
C25 C 0.7680(3) 0.5568(4) 0.49030(19) 0.0812(12) Uani 1 1 d . . .
H25 H 0.7204 0.5934 0.4745 0.097 Uiso 1 1 calc R A .
O1A O 0.68338(17) 0.3855(2) 0.36501(13) 0.0786(8) Uani 1 1 d . . .
O2A O 0.41933(19) 0.22063(19) 0.32078(13) 0.0725(8) Uani 1 1 d . . .
O3A O 0.48869(18) 0.3157(2) 0.53967(13) 0.0847(9) Uani 1 1 d . . .
C1A C 0.6079(2) 0.3470(3) 0.38907(17) 0.0571(9) Uani 1 1 d . . .
C2A C 0.5511(2) 0.3023(2) 0.34450(17) 0.0579(9) Uani 1 1 d . . .
H2A H 0.5646 0.2981 0.3004 0.069 Uiso 1 1 calc R . .
C3A C 0.4738(2) 0.2638(2) 0.36696(17) 0.0543(9) Uani 1 1 d . . .
C4A C 0.4524(2) 0.2693(2) 0.43175(18) 0.0593(9) Uani 1 1 d . . .
H4A H 0.4000 0.2434 0.4461 0.071 Uiso 1 1 calc R . .
C5A C 0.5111(2) 0.3144(3) 0.47538(17) 0.0586(9) Uani 1 1 d . . .
C6A C 0.5879(2) 0.3535(3) 0.45488(17) 0.0603(9) Uani 1 1 d . . .
H6A H 0.6263 0.3840 0.4846 0.072 Uiso 1 1 calc R . .
C100 C 0.1781(3) 0.1596(3) 0.33090(19) 0.0743(11) Uani 1 1 d . . .
C101 C 0.0936(3) 0.1237(4) 0.3103(2) 0.1014(15) Uani 1 1 d . . .
H10A H 0.0617 0.1034 0.3480 0.152 Uiso 1 1 calc R . .
H10B H 0.0999 0.0667 0.2815 0.152 Uiso 1 1 calc R . .
H10C H 0.0629 0.1771 0.2878 0.152 Uiso 1 1 calc R . .
N100 N 0.2435(3) 0.1876(3) 0.34737(18) 0.0993(12) Uani 1 1 d . . .
H1AO H 0.717(3) 0.423(3) 0.397(2) 0.107(15) Uiso 1 1 d . . .
H3AO H 0.538(3) 0.341(3) 0.568(2) 0.109(14) Uiso 1 1 d . . .
H2AO H 0.367(3) 0.206(3) 0.337(2) 0.107(17) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.194(5) . ?
C1 C4 1.357(9) . ?
C1 C2' 1.475(14) . ?
C1 C2 1.48(3) . ?
C1 C4' 1.599(8) . ?
C2 C3 1.40(3) . ?
C3 C13 1.519(11) . ?
C4 C5 1.303(11) . ?
C5 C23 1.490(9) . ?
C2' C3' 1.525(14) . ?
C2' C4' 1.749(19) 2_756 ?
C3' C13 1.560(7) . ?
C3' C5' 1.602(14) 2_756 ?
C4' C5' 1.519(7) . ?
C4' C2' 1.749(19) 2_756 ?
C5' C23 1.635(7) . ?
C5' C3' 1.602(14) 2_756 ?
C24 C23 1.367(5) . ?
C24 C25 1.357(5) . ?
C23 C22 1.341(6) . ?
N11 C11 1.312(4) . ?
N11 C15 1.328(4) . ?
C11 C12 1.364(5) . ?
C12 C13 1.371(5) . ?
C13 C14 1.374(4) . ?
C14 C15 1.369(5) . ?
N21 C21 1.317(5) . ?
N21 C25 1.320(5) . ?
C21 C22 1.374(5) . ?
O1A C1A 1.370(4) . ?
O2A C3A 1.373(4) . ?
O3A C5A 1.365(4) . ?
C1A C6A 1.388(4) . ?
C1A C2A 1.381(4) . ?
C2A C3A 1.383(5) . ?
C3A C4A 1.372(4) . ?
C4A C5A 1.389(4) . ?
C5A C6A 1.364(5) . ?
C100 N100 1.118(5) . ?
C100 C101 1.439(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 104.9(6) . . ?
O1 C1 C2' 123.6(5) . . ?
C4 C1 C2' 129.7(7) . . ?
O1 C1 C2 125.9(11) . . ?
C4 C1 C2 125.6(11) . . ?
C2' C1 C2 6.0(16) . . ?
O1 C1 C4' 125.0(4) . . ?
C4 C1 C4' 44.2(4) . . ?
C2' C1 C4' 105.6(6) . . ?
C2 C1 C4' 105.7(11) . . ?
C3 C2 C1 112(2) . . ?
C2 C3 C13 121.6(14) . . ?
C5 C4 C1 129.0(8) . . ?
C4 C5 C23 126.9(8) . . ?
C1 C2' C3' 120.9(6) . . ?
C1 C2' C4' 105.3(9) . 2_756 ?
C3' C2' C4' 84.4(8) . 2_756 ?
C2' C3' C13 112.1(7) . . ?
C2' C3' C5' 95.2(7) . 2_756 ?
C13 C3' C5' 118.7(5) . 2_756 ?
C5' C4' C1 115.1(5) . . ?
C5' C4' C2' 89.7(6) . 2_756 ?
C1 C4' C2' 115.9(6) . 2_756 ?
C23 C5' C4' 117.0(5) . . ?
C23 C5' C3' 123.8(4) . 2_756 ?
C4' C5' C3' 89.9(5) . 2_756 ?
C23 C24 C25 121.0(4) . . ?
C24 C23 C22 116.4(4) . . ?
C24 C23 C5' 111.5(4) . . ?
C22 C23 C5' 128.3(4) . . ?
C24 C23 C5 126.5(5) . . ?
C22 C23 C5 111.7(5) . . ?
C5' C23 C5 44.5(4) . . ?
C11 N11 C15 116.5(3) . . ?
N11 C11 C12 123.6(3) . . ?
C11 C12 C13 120.2(3) . . ?
C14 C13 C12 116.6(3) . . ?
C14 C13 C3 120.5(5) . . ?
C12 C13 C3 119.2(5) . . ?
C14 C13 C3' 121.9(4) . . ?
C12 C13 C3' 118.1(4) . . ?
C3 C13 C3' 37.0(4) . . ?
C13 C14 C15 119.4(3) . . ?
N11 C15 C14 123.7(3) . . ?
C21 N21 C25 116.2(3) . . ?
N21 C21 C22 123.6(4) . . ?
C21 C22 C23 120.0(4) . . ?
N21 C25 C24 122.7(4) . . ?
O1A C1A C6A 122.2(3) . . ?
O1A C1A C2A 116.9(3) . . ?
C6A C1A C2A 120.9(3) . . ?
C3A C2A C1A 118.4(3) . . ?
C2A C3A C4A 121.8(3) . . ?
C2A C3A O2A 116.3(3) . . ?
C4A C3A O2A 121.9(3) . . ?
C3A C4A C5A 118.3(3) . . ?
O3A C5A C6A 122.0(3) . . ?
O3A C5A C4A 116.6(3) . . ?
C6A C5A C4A 121.4(3) . . ?
C5A C6A C1A 119.1(3) . . ?
N100 C100 C101 179.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038

data_6
_database_code_depnum_ccdc_archive 'CCDC 688737'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N4 O4'
_chemical_formula_weight         536.62

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.1425(8)
_cell_length_b                   18.5623(16)
_cell_length_c                   16.1103(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.989(3)
_cell_angle_gamma                90.00
_cell_volume                     2664.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4589
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Apex-2 CCD area detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30448
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4589
_reflns_number_gt                2928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

The two methanol molecules are haveing high thermal parameters
and unusually short C...O distances. Therefore, the final structure was
refined without
MeOH molecules by using PLATON squeeze option.
;

_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)+(0.2000P)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_number_reflns         4589
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   0.710
_refine_ls_restrained_S_all      0.710
_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
O1A O -0.0094(2) -0.00121(9) 0.61605(12) 0.0645(5) Uani 1 1 d . . .
C11A C -0.0776(3) -0.05259(12) 0.63403(13) 0.0455(5) Uani 1 1 d . . .
C12A C -0.2001(2) -0.04494(11) 0.68231(13) 0.0429(5) Uani 1 1 d . . .
H12A H -0.1606 -0.0513 0.7436 0.052 Uiso 1 1 calc R . .
C13A C -0.0570(3) -0.12857(11) 0.60489(13) 0.0444(5) Uani 1 1 d . . .
H13A H -0.0124 -0.1608 0.6519 0.053 Uiso 1 1 calc R . .
N21A N -0.2462(4) 0.20587(16) 0.8300(2) 0.1007(10) Uani 1 1 d . . .
N31A N 0.2914(4) -0.31998(19) 0.5115(2) 0.1013(10) Uani 1 1 d . . .
C21A C -0.1587(4) 0.1489(2) 0.8475(2) 0.0942(11) Uani 1 1 d . . .
H21A H -0.0843 0.1495 0.8975 0.113 Uiso 1 1 calc R . .
C22A C -0.1701(3) 0.08905(16) 0.79682(18) 0.0710(8) Uani 1 1 d . . .
H22A H -0.1035 0.0509 0.8123 0.085 Uiso 1 1 calc R . .
C23A C -0.2790(3) 0.08528(13) 0.72361(14) 0.0497(6) Uani 1 1 d . . .
C24A C -0.3715(4) 0.14447(16) 0.70523(19) 0.0849(10) Uani 1 1 d . . .
H24A H -0.4472 0.1455 0.6558 0.102 Uiso 1 1 calc R . .
C25A C -0.3516(5) 0.2013(2) 0.7596(2) 0.1078(14) Uani 1 1 d . . .
H25A H -0.4174 0.2399 0.7460 0.129 Uiso 1 1 calc R . .
C26A C -0.3015(3) 0.02210(12) 0.66397(13) 0.0453(5) Uani 1 1 d . . .
H26A H -0.3005 0.0396 0.6067 0.054 Uiso 1 1 calc R . .
C31A C 0.3194(5) -0.2559(3) 0.4859(4) 0.1299(17) Uani 1 1 d . . .
H31A H 0.4019 -0.2505 0.4616 0.156 Uiso 1 1 calc R . .
C32A C 0.2354(4) -0.19620(19) 0.4924(3) 0.0970(12) Uani 1 1 d . . .
H32A H 0.2623 -0.1520 0.4730 0.116 Uiso 1 1 calc R . .
C33A C 0.1124(3) -0.20069(13) 0.52707(15) 0.0522(6) Uani 1 1 d . . .
C34A C 0.0834(3) -0.26709(14) 0.55609(18) 0.0642(7) Uani 1 1 d . . .
H34A H 0.0026 -0.2736 0.5815 0.077 Uiso 1 1 calc R . .
C35A C 0.1756(4) -0.32497(17) 0.5474(2) 0.0804(9) Uani 1 1 d . . .
H35A H 0.1544 -0.3696 0.5681 0.096 Uiso 1 1 calc R . .
C36A C 0.0141(3) -0.13654(12) 0.52754(14) 0.0478(6) Uani 1 1 d . . .
H36A H 0.0623 -0.0919 0.5152 0.057 Uiso 1 1 calc R . .
O1B O -0.44756(19) -0.10198(11) 0.50037(10) 0.0654(5) Uani 1 1 d . . .
C11B C -0.3463(3) -0.11692(12) 0.56040(14) 0.0454(5) Uani 1 1 d . . .
C12B C -0.3424(3) -0.09208(12) 0.65005(13) 0.0457(5) Uani 1 1 d . . .
H12B H -0.3516 -0.1317 0.6888 0.055 Uiso 1 1 calc R . .
C13B C -0.2094(2) -0.15681(11) 0.55110(12) 0.0425(5) Uani 1 1 d . . .
H13B H -0.2204 -0.2084 0.5611 0.051 Uiso 1 1 calc R . .
N21B N -0.6525(3) -0.01338(16) 0.87090(17) 0.0795(7) Uani 1 1 d . . .
N31B N -0.2366(4) -0.29840(19) 0.26362(17) 0.0976(10) Uani 1 1 d . . .
C21B C -0.5188(4) -0.0420(2) 0.87798(19) 0.0853(10) Uani 1 1 d . . .
H21B H -0.4689 -0.0583 0.9315 0.102 Uiso 1 1 calc R . .
C22B C -0.4476(4) -0.04958(19) 0.81224(17) 0.0755(9) Uani 1 1 d . . .
H22B H -0.3535 -0.0712 0.8217 0.091 Uiso 1 1 calc R . .
C23B C -0.5151(3) -0.02535(12) 0.73269(14) 0.0497(6) Uani 1 1 d . . .
C24B C -0.6551(3) 0.0031(2) 0.72517(19) 0.0785(9) Uani 1 1 d . . .
H24B H -0.7083 0.0194 0.6724 0.094 Uiso 1 1 calc R . .
C25B C -0.7177(4) 0.0078(2) 0.7941(2) 0.0893(10) Uani 1 1 d . . .
H25B H -0.8134 0.0275 0.7860 0.107 Uiso 1 1 calc R . .
C26B C -0.4434(3) -0.02756(12) 0.65770(13) 0.0477(6) Uani 1 1 d . . .
H26B H -0.5175 -0.0193 0.6043 0.057 Uiso 1 1 calc R . .
C31B C -0.1501(5) -0.2406(3) 0.26412(19) 0.0979(12) Uani 1 1 d . . .
H31B H -0.1076 -0.2335 0.2175 0.118 Uiso 1 1 calc R . .
C32B C -0.1191(4) -0.19061(18) 0.32902(16) 0.0765(9) Uani 1 1 d . . .
H32B H -0.0574 -0.1514 0.3254 0.092 Uiso 1 1 calc R . .
C33B C -0.1799(3) -0.19903(13) 0.39909(14) 0.0518(6) Uani 1 1 d . . .
C34B C -0.2679(3) -0.25923(15) 0.39984(17) 0.0637(7) Uani 1 1 d . . .
H34B H -0.3102 -0.2683 0.4462 0.076 Uiso 1 1 calc R . .
C35B C -0.2929(4) -0.30607(18) 0.3312(2) 0.0861(10) Uani 1 1 d . . .
H35B H -0.3540 -0.3458 0.3331 0.103 Uiso 1 1 calc R . .
C36B C -0.1495(3) -0.14493(12) 0.47025(13) 0.0459(6) Uani 1 1 d . . .
H36B H -0.1835 -0.0976 0.4466 0.055 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
O1A C11A 1.210(3) . ?
C11A C12A 1.507(3) . ?
C11A C13A 1.512(3) . ?
C12A C26A 1.540(3) . ?
C12A C12B 1.556(3) . ?
C13A C36A 1.537(3) . ?
C13A C13B 1.557(3) . ?
N21A C25A 1.316(5) . ?
N21A C21A 1.317(4) . ?
N31A C31A 1.302(6) . ?
N31A C35A 1.320(5) . ?
C21A C22A 1.370(4) . ?
C22A C23A 1.364(4) . ?
C23A C24A 1.378(4) . ?
C23A C26A 1.501(3) . ?
C24A C25A 1.356(4) . ?
C26A C26B 1.576(3) . ?
C31A C32A 1.366(5) . ?
C32A C33A 1.367(4) . ?
C33A C34A 1.365(4) . ?
C33A C36A 1.493(3) . ?
C34A C35A 1.392(4) . ?
C36A C36B 1.579(3) . ?
O1B C11B 1.211(3) . ?
C11B C13B 1.491(3) . ?
C11B C12B 1.509(3) . ?
C12B C26B 1.534(3) . ?
C13B C36B 1.538(3) . ?
N21B C21B 1.314(4) . ?
N21B C25B 1.307(4) . ?
N31B C35B 1.313(5) . ?
N31B C31B 1.332(5) . ?
C21B C22B 1.369(4) . ?
C22B C23B 1.367(4) . ?
C23B C24B 1.364(4) . ?
C23B C26B 1.499(3) . ?
C24B C25B 1.362(4) . ?
C31B C32B 1.379(5) . ?
C32B C33B 1.375(4) . ?
C33B C34B 1.379(4) . ?
C33B C36B 1.502(3) . ?
C34B C35B 1.385(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C11A C12A 122.2(2) . . ?
O1A C11A C13A 123.7(2) . . ?
C12A C11A C13A 114.01(19) . . ?
C11A C12A C26A 117.52(18) . . ?
C11A C12A C12B 115.89(17) . . ?
C26A C12A C12B 88.21(16) . . ?
C11A C13A C36A 116.52(18) . . ?
C11A C13A C13B 109.20(18) . . ?
C36A C13A C13B 90.29(16) . . ?
C25A N21A C21A 115.1(3) . . ?
C31A N31A C35A 115.9(3) . . ?
N21A C21A C22A 124.2(3) . . ?
C23A C22A C21A 120.0(3) . . ?
C22A C23A C24A 116.0(2) . . ?
C22A C23A C26A 124.2(2) . . ?
C24A C23A C26A 119.8(2) . . ?
C23A C24A C25A 119.6(3) . . ?
N21A C25A C24A 125.0(3) . . ?
C23A C26A C12A 121.24(18) . . ?
C23A C26A C26B 119.38(19) . . ?
C12A C26A C26B 89.47(16) . . ?
N31A C31A C32A 124.3(4) . . ?
C31A C32A C33A 120.7(4) . . ?
C34A C33A C32A 115.9(3) . . ?
C34A C33A C36A 123.7(2) . . ?
C32A C33A C36A 120.3(2) . . ?
C33A C34A C35A 119.6(3) . . ?
N31A C35A C34A 123.6(3) . . ?
C33A C36A C13A 116.47(19) . . ?
C33A C36A C36B 114.24(18) . . ?
C13A C36A C36B 88.02(16) . . ?
O1B C11B C13B 122.8(2) . . ?
O1B C11B C12B 123.0(2) . . ?
C13B C11B C12B 114.08(18) . . ?
C11B C12B C26B 115.48(18) . . ?
C11B C12B C12A 109.27(18) . . ?
C26B C12B C12A 90.42(16) . . ?
C11B C13B C36B 118.73(18) . . ?
C11B C13B C13A 116.32(17) . . ?
C36B C13B C13A 88.78(16) . . ?
C21B N21B C25B 114.9(3) . . ?
C35B N31B C31B 115.2(3) . . ?
N21B C21B C22B 124.7(3) . . ?
C23B C22B C21B 119.9(3) . . ?
C22B C23B C24B 115.3(2) . . ?
C22B C23B C26B 124.0(2) . . ?
C24B C23B C26B 120.7(2) . . ?
C25B C24B C23B 120.7(3) . . ?
N21B C25B C24B 124.5(3) . . ?
C23B C26B C12B 117.80(18) . . ?
C23B C26B C26A 115.80(18) . . ?
C12B C26B C26A 87.70(16) . . ?
N31B C31B C32B 124.5(3) . . ?
C31B C32B C33B 119.6(3) . . ?
C34B C33B C32B 116.4(2) . . ?
C34B C33B C36B 122.9(2) . . ?
C32B C33B C36B 120.7(2) . . ?
C33B C34B C35B 119.6(3) . . ?
N31B C35B C34B 124.7(3) . . ?
C33B C36B C13B 120.69(19) . . ?
C33B C36B C36A 120.03(19) . . ?
C13B C36B C36A 89.42(16) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028

######END


