# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Santiago Luis'
_publ_contact_author_email       LUISS@QIO.UJI.ES

_publ_section_title              
;
Crystal structures of the HCl salts of pseudopeptidic
macrocycles display "knobs into holes" hydrophobic interactions between
aliphatic side chains
;
loop_
_publ_author_name
'Santiago Luis'
'Ignacio Alfonso'
'Michael Bolte'
'Miriam Bru'
'M Isabel Burguete'

data_a2v
_database_code_depnum_ccdc_archive 'CCDC 665568'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H72 Cl4 N8 O8'
_chemical_formula_weight         934.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'

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

_cell_length_a                   15.521(3)
_cell_length_b                   26.412(5)
_cell_length_c                   6.9655(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2855.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       omega-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23532
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_sigmaI/netI    0.1432
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         30.56
_reflns_number_total             8450
_reflns_number_gt                3769
_reflns_threshold_expression     I>2σ(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)+(0.1731P)²] 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     SHELXL
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_number_reflns         8450
_refine_ls_number_parameters     282
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2118
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.3160
_refine_ls_wR_factor_gt          0.2571
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.88204(9) 0.86039(5) -0.7669(2) 0.0466(4) Uani 1 1 d . . .
Cl2 Cl 0.80368(13) 0.76865(6) -0.2917(2) 0.0596(5) Uani 1 1 d . . .
C1 C 0.4679(3) 0.6071(2) -0.7383(12) 0.0509(15) Uani 1 1 d . . .
H1A H 0.4852 0.5812 -0.8293 0.061 Uiso 1 1 calc R . .
H1B H 0.4721 0.5926 -0.6107 0.061 Uiso 1 1 calc R . .
N1 N 0.3748(3) 0.62075(15) -0.7762(7) 0.0370(9) Uani 1 1 d . . .
H1C H 0.3647 0.6522 -0.7317 0.044 Uiso 1 1 calc R . .
H1D H 0.3656 0.6210 -0.9037 0.044 Uiso 1 1 calc R . .
C11 C 0.5305(3) 0.65091(19) -0.7524(10) 0.0461(14) Uani 1 1 d . . .
C12 C 0.5633(4) 0.6657(3) -0.9277(9) 0.0564(18) Uani 1 1 d . . .
H12 H 0.5454 0.6497 -1.0396 0.068 Uiso 1 1 calc R . .
C13 C 0.6236(4) 0.7049(3) -0.9365(9) 0.0528(16) Uani 1 1 d . . .
H13 H 0.6435 0.7159 -1.0553 0.063 Uiso 1 1 calc R . .
C14 C 0.6537(3) 0.72733(19) -0.7718(9) 0.0430(13) Uani 1 1 d . . .
C15 C 0.6207(4) 0.7115(3) -0.5982(9) 0.0541(16) Uani 1 1 d . . .
H15 H 0.6404 0.7265 -0.4858 0.065 Uiso 1 1 calc R . .
C16 C 0.5590(4) 0.6739(3) -0.5866(10) 0.0572(18) Uani 1 1 d . . .
H16 H 0.5369 0.6642 -0.4680 0.069 Uiso 1 1 calc R . .
C2 C 0.7208(3) 0.7682(2) -0.7810(10) 0.0478(14) Uani 1 1 d . . .
H2A H 0.7206 0.7828 -0.9088 0.057 Uiso 1 1 calc R . .
H2B H 0.7055 0.7948 -0.6911 0.057 Uiso 1 1 calc R . .
N2 N 0.8095(3) 0.75015(14) -0.7364(7) 0.0374(10) Uani 1 1 d . . .
H2C H 0.8461 0.7764 -0.7487 0.045 Uiso 1 1 calc R . .
H2D H 0.8110 0.7402 -0.6129 0.045 Uiso 1 1 calc R . .
C3 C 0.8410(3) 0.70795(19) -0.8579(8) 0.0357(11) Uani 1 1 d . . .
H3' H 0.8102 0.7086 -0.9808 0.043 Uiso 1 1 calc R . .
C31 C 0.9386(4) 0.7135(2) -0.8961(10) 0.0506(15) Uani 1 1 d . . .
H31 H 0.9468 0.7481 -0.9440 0.061 Uiso 1 1 calc R . .
C311 C 0.9923(5) 0.7096(3) -0.7157(13) 0.079(2) Uani 1 1 d . . .
H31A H 0.9707 0.7329 -0.6214 0.118 Uiso 1 1 calc R . .
H31B H 1.0511 0.7177 -0.7449 0.118 Uiso 1 1 calc R . .
H31C H 0.9891 0.6758 -0.6662 0.118 Uiso 1 1 calc R . .
C312 C 0.9674(5) 0.6791(3) -1.0550(12) 0.072(2) Uani 1 1 d . . .
H31D H 0.9302 0.6834 -1.1639 0.109 Uiso 1 1 calc R . .
H31E H 0.9649 0.6446 -1.0121 0.109 Uiso 1 1 calc R . .
H31F H 1.0254 0.6873 -1.0906 0.109 Uiso 1 1 calc R . .
C4 C 0.8206(3) 0.65790(18) -0.7544(8) 0.0382(11) Uani 1 1 d . . .
O4 O 0.8248(3) 0.65537(16) -0.5816(6) 0.0559(12) Uani 1 1 d . . .
N3 N 0.8031(3) 0.61876(17) -0.8687(7) 0.0481(12) Uani 1 1 d . . .
H3 H 0.7993 0.6236 -0.9905 0.058 Uiso 1 1 calc R . .
C5 C 0.7901(4) 0.56797(19) -0.7929(9) 0.0495(15) Uani 1 1 d . . .
H5A H 0.8257 0.5637 -0.6796 0.059 Uiso 1 1 calc R . .
H5B H 0.8092 0.5436 -0.8879 0.059 Uiso 1 1 calc R . .
C6 C 0.6997(3) 0.55683(18) -0.7419(9) 0.0440(12) Uani 1 1 d . . .
H6A H 0.6801 0.5810 -0.6466 0.053 Uiso 1 1 calc R . .
H6B H 0.6637 0.5605 -0.8550 0.053 Uiso 1 1 calc R . .
C7 C 0.6781(3) 0.46604(18) -0.7782(8) 0.0353(11) Uani 1 1 d . . .
O7 O 0.6624(3) 0.46897(15) -0.9490(6) 0.0609(13) Uani 1 1 d . . .
N4 N 0.6906(3) 0.50601(17) -0.6665(7) 0.0466(12) Uani 1 1 d . . .
H4 H 0.6934 0.5016 -0.5444 0.056 Uiso 1 1 calc R . .
C8 C 0.6863(4) 0.4145(2) -0.6858(9) 0.0462(14) Uani 1 1 d . . .
H8 H 0.6697 0.4180 -0.5507 0.055 Uiso 1 1 calc R . .
C81 C 0.7781(5) 0.3950(3) -0.6909(15) 0.080(3) Uani 1 1 d . . .
H81 H 0.7762 0.3589 -0.6579 0.096 Uiso 1 1 calc R . .
C811 C 0.8345(7) 0.4207(4) -0.545(2) 0.142(6) Uani 1 1 d . . .
H81A H 0.8920 0.4074 -0.5533 0.213 Uiso 1 1 calc R . .
H81B H 0.8121 0.4147 -0.4184 0.213 Uiso 1 1 calc R . .
H81C H 0.8356 0.4565 -0.5693 0.213 Uiso 1 1 calc R . .
C812 C 0.8166(6) 0.3992(4) -0.893(2) 0.130(5) Uani 1 1 d . . .
H81D H 0.7800 0.3820 -0.9826 0.195 Uiso 1 1 calc R . .
H81E H 0.8728 0.3840 -0.8942 0.195 Uiso 1 1 calc R . .
H81F H 0.8212 0.4343 -0.9279 0.195 Uiso 1 1 calc R . .
O1W O 0.7468(12) 0.5090(8) -1.2716(19) 0.145(9) Uani 0.544(19) 1 d P A 1
O1W' O 0.6590(10) 0.5286(4) -1.2656(14) 0.075(6) Uani 0.456(19) 1 d P A 2
O2W O 0.7437(6) 0.6183(5) -0.2558(10) 0.170(4) Uani 1 1 d D . .
H1W2 H 0.7936 0.6074 -0.2343 0.254 Uiso 1 1 d RD . .
H2W2 H 0.7437 0.6473 -0.3079 0.254 Uiso 1 1 d RD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.513(7) . ?
C1 C11 1.515(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C8 1.470(7) 2_665 ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
C11 C16 1.378(9) . ?
C11 C12 1.380(9) . ?
C12 C13 1.396(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(9) . ?
C14 C2 1.502(7) . ?
C15 C16 1.382(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C2 N2 1.490(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N2 C3 1.482(7) . ?
N2 H2C 0.9000 . ?
N2 H2D 0.9000 . ?
C3 C4 1.538(7) . ?
C3 C31 1.545(8) . ?
C3 H3' 0.9800 . ?
C31 C312 1.500(10) . ?
C31 C311 1.511(10) . ?
C31 H31 0.9800 . ?
C311 H31A 0.9600 . ?
C311 H31B 0.9600 . ?
C311 H31C 0.9600 . ?
C312 H31D 0.9600 . ?
C312 H31E 0.9600 . ?
C312 H31F 0.9600 . ?
C4 O4 1.207(7) . ?
C4 N3 1.333(7) . ?
N3 C5 1.455(7) . ?
N3 H3 0.8600 . ?
C5 C6 1.477(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N4 1.448(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O7 1.217(7) . ?
C7 N4 1.325(7) . ?
C7 C8 1.511(7) . ?
N4 H4 0.8600 . ?
C8 N1 1.470(7) 2_665 ?
C8 C81 1.515(10) . ?
C8 H8 0.9800 . ?
C81 C811 1.505(13) . ?
C81 C812 1.532(15) . ?
C81 H81 0.9800 . ?
C811 H81A 0.9600 . ?
C811 H81B 0.9600 . ?
C811 H81C 0.9600 . ?
C812 H81D 0.9600 . ?
C812 H81E 0.9600 . ?
C812 H81F 0.9600 . ?
O2W H1W2 0.8404 . ?
O2W H2W2 0.8463 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C11 114.8(4) . . ?
N1 C1 H1A 108.6 . . ?
C11 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C11 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C8 N1 C1 113.0(4) 2_665 . ?
C8 N1 H1C 109.0 2_665 . ?
C1 N1 H1C 109.0 . . ?
C8 N1 H1D 109.0 2_665 . ?
C1 N1 H1D 109.0 . . ?
H1C N1 H1D 107.8 . . ?
C16 C11 C12 119.9(5) . . ?
C16 C11 C1 119.2(6) . . ?
C12 C11 C1 120.7(6) . . ?
C11 C12 C13 119.7(6) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 118.4(5) . . ?
C13 C14 C2 120.7(6) . . ?
C15 C14 C2 120.9(6) . . ?
C14 C15 C16 121.8(6) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 119.3(6) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N2 C2 C14 113.7(4) . . ?
N2 C2 H2A 108.8 . . ?
C14 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
C14 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 N2 C2 115.2(4) . . ?
C3 N2 H2C 108.5 . . ?
C2 N2 H2C 108.5 . . ?
C3 N2 H2D 108.5 . . ?
C2 N2 H2D 108.5 . . ?
H2C N2 H2D 107.5 . . ?
N2 C3 C4 108.1(4) . . ?
N2 C3 C31 110.5(4) . . ?
C4 C3 C31 111.3(4) . . ?
N2 C3 H3' 109.0 . . ?
C4 C3 H3' 109.0 . . ?
C31 C3 H3' 109.0 . . ?
C312 C31 C311 114.1(6) . . ?
C312 C31 C3 111.2(5) . . ?
C311 C31 C3 113.0(6) . . ?
C312 C31 H31 105.9 . . ?
C311 C31 H31 105.9 . . ?
C3 C31 H31 105.9 . . ?
C31 C311 H31A 109.5 . . ?
C31 C311 H31B 109.5 . . ?
H31A C311 H31B 109.5 . . ?
C31 C311 H31C 109.5 . . ?
H31A C311 H31C 109.5 . . ?
H31B C311 H31C 109.5 . . ?
C31 C312 H31D 109.5 . . ?
C31 C312 H31E 109.5 . . ?
H31D C312 H31E 109.5 . . ?
C31 C312 H31F 109.5 . . ?
H31D C312 H31F 109.5 . . ?
H31E C312 H31F 109.5 . . ?
O4 C4 N3 124.3(5) . . ?
O4 C4 C3 120.2(5) . . ?
N3 C4 C3 115.4(5) . . ?
C4 N3 C5 121.8(5) . . ?
C4 N3 H3 119.1 . . ?
C5 N3 H3 119.1 . . ?
N3 C5 C6 113.7(5) . . ?
N3 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
N3 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N4 C6 C5 111.4(4) . . ?
N4 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O7 C7 N4 123.5(5) . . ?
O7 C7 C8 119.4(5) . . ?
N4 C7 C8 117.1(5) . . ?
C7 N4 C6 122.7(5) . . ?
C7 N4 H4 118.7 . . ?
C6 N4 H4 118.7 . . ?
N1 C8 C7 109.5(4) 2_665 . ?
N1 C8 C81 112.4(5) 2_665 . ?
C7 C8 C81 112.0(5) . . ?
N1 C8 H8 107.6 2_665 . ?
C7 C8 H8 107.6 . . ?
C81 C8 H8 107.6 . . ?
C811 C81 C8 112.2(8) . . ?
C811 C81 C812 111.2(9) . . ?
C8 C81 C812 111.3(7) . . ?
C811 C81 H81 107.3 . . ?
C8 C81 H81 107.3 . . ?
C812 C81 H81 107.3 . . ?
C81 C811 H81A 109.5 . . ?
C81 C811 H81B 109.5 . . ?
H81A C811 H81B 109.5 . . ?
C81 C811 H81C 109.5 . . ?
H81A C811 H81C 109.5 . . ?
H81B C811 H81C 109.5 . . ?
C81 C812 H81D 109.5 . . ?
C81 C812 H81E 109.5 . . ?
H81D C812 H81E 109.5 . . ?
C81 C812 H81F 109.5 . . ?
H81D C812 H81F 109.5 . . ?
H81E C812 H81F 109.5 . . ?
H1W2 O2W H2W2 112.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 N1 C8 -155.7(6) . . . 2_665 ?
N1 C1 C11 C16 100.4(7) . . . . ?
N1 C1 C11 C12 -83.9(7) . . . . ?
C16 C11 C12 C13 -1.7(10) . . . . ?
C1 C11 C12 C13 -177.4(6) . . . . ?
C11 C12 C13 C14 3.1(11) . . . . ?
C12 C13 C14 C15 -2.3(9) . . . . ?
C12 C13 C14 C2 177.8(6) . . . . ?
C13 C14 C15 C16 0.2(9) . . . . ?
C2 C14 C15 C16 -179.9(6) . . . . ?
C12 C11 C16 C15 -0.3(10) . . . . ?
C1 C11 C16 C15 175.5(6) . . . . ?
C14 C15 C16 C11 1.1(11) . . . . ?
C13 C14 C2 N2 -100.6(7) . . . . ?
C15 C14 C2 N2 79.5(7) . . . . ?
C14 C2 N2 C3 56.4(7) . . . . ?
C2 N2 C3 C4 -93.4(5) . . . . ?
C2 N2 C3 C31 144.6(5) . . . . ?
N2 C3 C31 C312 -166.2(5) . . . . ?
C4 C3 C31 C312 73.6(7) . . . . ?
N2 C3 C31 C311 63.9(6) . . . . ?
C4 C3 C31 C311 -56.2(7) . . . . ?
N2 C3 C4 O4 -35.7(7) . . . . ?
C31 C3 C4 O4 85.8(7) . . . . ?
N2 C3 C4 N3 147.4(5) . . . . ?
C31 C3 C4 N3 -91.0(6) . . . . ?
O4 C4 N3 C5 -2.2(9) . . . . ?
C3 C4 N3 C5 174.5(5) . . . . ?
C4 N3 C5 C6 89.5(7) . . . . ?
N3 C5 C6 N4 -179.7(5) . . . . ?
O7 C7 N4 C6 -9.6(9) . . . . ?
C8 C7 N4 C6 168.9(5) . . . . ?
C5 C6 N4 C7 -87.0(7) . . . . ?
O7 C7 C8 N1 -35.2(7) . . . 2_665 ?
N4 C7 C8 N1 146.2(5) . . . 2_665 ?
O7 C7 C8 C81 90.2(7) . . . . ?
N4 C7 C8 C81 -88.3(7) . . . . ?
N1 C8 C81 C811 -160.5(7) 2_665 . . . ?
C7 C8 C81 C811 75.7(9) . . . . ?
N1 C8 C81 C812 74.2(7) 2_665 . . . ?
C7 C8 C81 C812 -49.6(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C Cl2 0.90 2.30 3.158(4) 159.1 4_464
N1 H1D Cl1 0.90 2.36 3.224(5) 160.8 4_463
N2 H2C Cl1 0.90 2.29 3.129(4) 154.8 .
N2 H2D O4 0.90 2.26 2.736(6) 112.6 .
N2 H2D Cl2 0.90 2.36 3.137(5) 144.1 .
N3 H3 O2W 0.86 2.04 2.849(9) 155.5 1_554
N4 H4 O1W 0.86 2.08 2.887(14) 155.5 1_556
N4 H4 O1W' 0.86 2.14 2.898(11) 147.3 1_556

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.756
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.197

data_ile
_database_code_depnum_ccdc_archive 'CCDC 706282'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H90 Cl4 N8 O11'
_chemical_formula_weight         1049.04

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'
Cl Cl 0.1484 0.1585 '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
_chemical_absolute_configuration ad

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

_cell_length_a                   26.700(5)
_cell_length_b                   7.0199(14)
_cell_length_c                   17.975(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.95(3)
_cell_angle_gamma                90.00
_cell_volume                     3029.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9170
_diffrn_reflns_av_R_equivalents  0.1510
_diffrn_reflns_av_sigmaI/netI    0.2157
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         25.71
_reflns_number_total             4906
_reflns_number_gt                2178
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1464P)²] 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     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         4906
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.1134
_refine_ls_wR_factor_ref         0.3102
_refine_ls_wR_factor_gt          0.2563
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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
Cl1 Cl 0.84269(12) 0.8528(4) 0.8347(2) 0.0553(9) Uani 1 1 d . . .
Cl2 Cl 0.73673(11) 0.3760(4) 0.8152(2) 0.0591(9) Uani 1 1 d . . .
C1 C 0.4720(4) 0.8523(19) 1.2016(7) 0.043(3) Uani 1 1 d . . .
H1A H 0.4601 0.9667 1.1659 0.052 Uiso 1 1 calc R . .
H1B H 0.4425 0.7548 1.1772 0.052 Uiso 1 1 calc R . .
N1 N 0.5247(4) 0.7778(13) 1.2031(6) 0.044(2) Uani 1 1 d . . .
H1 H 0.5308 0.6543 1.2064 0.052 Uiso 1 1 calc R . .
C2 C 0.5625(4) 0.8958(14) 1.1994(7) 0.042(3) Uani 1 1 d . . .
O2 O 0.5589(4) 1.0682(11) 1.1963(7) 0.064(3) Uani 1 1 d . . .
C3 C 0.6169(4) 0.7972(14) 1.2075(8) 0.041(3) Uani 1 1 d . . .
H3 H 0.6070 0.6644 1.1860 0.049 Uiso 1 1 calc R . .
C31 C 0.6634(5) 0.7839(18) 1.2949(8) 0.051(3) Uani 1 1 d . . .
H31 H 0.6967 0.7298 1.2905 0.061 Uiso 1 1 calc R . .
C311 C 0.6808(7) 0.975(2) 1.3381(12) 0.081(5) Uani 1 1 d . . .
H31A H 0.7109 0.9560 1.3938 0.122 Uiso 1 1 calc R . .
H31B H 0.6489 1.0343 1.3422 0.122 Uiso 1 1 calc R . .
H31C H 0.6938 1.0579 1.3064 0.122 Uiso 1 1 calc R . .
C312 C 0.6464(6) 0.641(3) 1.3435(11) 0.078(5) Uani 1 1 d . . .
H31D H 0.6269 0.5327 1.3068 0.117 Uiso 1 1 calc R . .
H31E H 0.6198 0.7026 1.3608 0.117 Uiso 1 1 calc R . .
C313 C 0.6959(9) 0.564(3) 1.4205(15) 0.121(8) Uani 1 1 d . . .
H31F H 0.6824 0.4759 1.4501 0.182 Uiso 1 1 calc R . .
H31G H 0.7156 0.6698 1.4570 0.182 Uiso 1 1 calc R . .
H31H H 0.7214 0.4958 1.4037 0.182 Uiso 1 1 calc R . .
N2 N 0.6349(4) 0.9029(11) 1.1498(6) 0.044(2) Uani 1 1 d . . .
H2A H 0.6388 1.0299 1.1638 0.053 Uiso 1 1 calc R . .
H2B H 0.6693 0.8582 1.1579 0.053 Uiso 1 1 calc R . .
C4 C 0.5968(5) 0.886(2) 1.0620(7) 0.057(3) Uani 1 1 d . . .
H4A H 0.5707 0.9947 1.0452 0.069 Uiso 1 1 calc R . .
H4B H 0.5746 0.7675 1.0530 0.069 Uiso 1 1 calc R . .
C41 C 0.6284(4) 0.880(2) 1.0070(7) 0.050(3) Uani 1 1 d . . .
C42 C 0.6465(5) 0.7089(18) 0.9896(9) 0.053(4) Uani 1 1 d . . .
H42 H 0.6371 0.5932 1.0079 0.063 Uiso 1 1 calc R . .
C43 C 0.6785(5) 0.7034(15) 0.9454(9) 0.044(3) Uani 1 1 d . . .
H43 H 0.6891 0.5846 0.9313 0.053 Uiso 1 1 calc R . .
C44 C 0.6954(4) 0.8783(18) 0.9215(7) 0.046(3) Uani 1 1 d . . .
C45 C 0.6762(6) 1.0446(16) 0.9394(9) 0.050(3) Uani 1 1 d . . .
H45 H 0.6870 1.1613 0.9239 0.060 Uiso 1 1 calc R . .
C46 C 0.6423(5) 1.0519(16) 0.9785(8) 0.046(3) Uani 1 1 d . . .
H46 H 0.6283 1.1705 0.9865 0.055 Uiso 1 1 calc R . .
C5 C 0.7370(4) 0.874(2) 0.8863(7) 0.053(3) Uani 1 1 d . . .
H5A H 0.7541 1.0018 0.8935 0.063 Uiso 1 1 calc R . .
H5B H 0.7669 0.7836 0.9195 0.063 Uiso 1 1 calc R . .
N3 N 0.7159(3) 0.8196(11) 0.7978(5) 0.038(2) Uani 1 1 d . . .
H3A H 0.7455 0.8206 0.7845 0.045 Uiso 1 1 calc R . .
H3B H 0.7031 0.6962 0.7920 0.045 Uiso 1 1 calc R . .
N4 N 0.5747(4) 0.9707(14) 0.7184(7) 0.053(3) Uani 1 1 d . . .
H4 H 0.5801 1.0941 0.7169 0.063 Uiso 1 1 calc R . .
C6 C 0.6710(4) 0.9389(15) 0.7365(8) 0.045(3) Uani 1 1 d . . .
H6 H 0.6741 1.0693 0.7604 0.054 Uiso 1 1 calc R . .
C61 C 0.6769(5) 0.956(3) 0.6558(9) 0.073(5) Uani 1 1 d . . .
H61 H 0.7155 1.0053 0.6722 0.087 Uiso 1 1 calc R . .
C611 C 0.6744(7) 0.766(3) 0.6149(10) 0.096(6) Uani 1 1 d . . .
H61A H 0.7016 0.6790 0.6549 0.144 Uiso 1 1 calc R . .
H61B H 0.6830 0.7835 0.5677 0.144 Uiso 1 1 calc R . .
H61C H 0.6369 0.7122 0.5956 0.144 Uiso 1 1 calc R . .
C612 C 0.6389(6) 1.106(3) 0.6008(11) 0.095(6) Uani 1 1 d . . .
H61D H 0.6400 1.2160 0.6362 0.143 Uiso 1 1 calc R . .
H61E H 0.6005 1.0549 0.5773 0.143 Uiso 1 1 calc R . .
C613 C 0.6492(11) 1.184(5) 0.528(2) 0.194(17) Uani 1 1 d . . .
H61F H 0.6196 1.2742 0.4957 0.292 Uiso 1 1 calc R . .
H61G H 0.6493 1.0784 0.4926 0.292 Uiso 1 1 calc R . .
H61H H 0.6853 1.2496 0.5499 0.292 Uiso 1 1 calc R . .
C7 C 0.6144(4) 0.8525(19) 0.7238(7) 0.047(3) Uani 1 1 d . . .
O7 O 0.6087(4) 0.6755(10) 0.7178(7) 0.065(3) Uani 1 1 d . . .
C8 C 0.5219(4) 0.9026(18) 0.7146(8) 0.050(3) Uani 1 1 d . . .
H8A H 0.5093 0.7893 0.6783 0.060 Uiso 1 1 calc R . .
H8B H 0.4932 1.0030 0.6905 0.060 Uiso 1 1 calc R . .
O1W O 0.5000 0.7490(11) 0.5000 0.0207(18) Uani 1 2 d S . .
O2W O 0.4932(4) 1.3871(13) 1.1627(8) 0.094(4) Uani 1 1 d . . .
O3W O 0.5944(6) 1.3465(16) 0.7831(8) 0.104(4) Uani 1 1 d . . .
O4W O 0.5102(6) 1.396(2) 0.4304(10) 0.207(12) Uani 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 C8 1.484(15) 2_657 ?
C1 N1 1.490(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N1 C2 1.330(12) . ?
N1 H1 0.8800 . ?
C2 O2 1.214(12) . ?
C2 C3 1.556(13) . ?
C3 N2 1.515(13) . ?
C3 C31 1.521(18) . ?
C3 H3 1.0000 . ?
C31 C311 1.517(19) . ?
C31 C312 1.526(18) . ?
C31 H31 1.0000 . ?
C311 H31A 0.9800 . ?
C311 H31B 0.9800 . ?
C311 H31C 0.9800 . ?
C312 C313 1.54(3) . ?
C312 H31D 0.9900 . ?
C312 H31E 0.9900 . ?
C313 H31F 0.9800 . ?
C313 H31G 0.9800 . ?
C313 H31H 0.9800 . ?
N2 C4 1.461(15) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C4 C41 1.554(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C41 C42 1.384(18) . ?
C41 C46 1.421(18) . ?
C42 C43 1.400(17) . ?
C42 H42 0.9500 . ?
C43 C44 1.436(15) . ?
C43 H43 0.9500 . ?
C44 C45 1.368(16) . ?
C44 C5 1.501(13) . ?
C45 C46 1.368(17) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C5 N3 1.486(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C6 1.481(14) . ?
N3 H3A 0.9200 . ?
N3 H3B 0.9200 . ?
N4 C7 1.314(14) . ?
N4 C8 1.464(13) . ?
N4 H4 0.8800 . ?
C6 C61 1.530(18) . ?
C6 C7 1.551(14) . ?
C6 H6 1.0000 . ?
C61 C612 1.50(2) . ?
C61 C611 1.51(2) . ?
C61 H61 1.0000 . ?
C611 H61A 0.9800 . ?
C611 H61B 0.9800 . ?
C611 H61C 0.9800 . ?
C612 C613 1.55(3) . ?
C612 H61D 0.9900 . ?
C612 H61E 0.9900 . ?
C613 H61F 0.9800 . ?
C613 H61G 0.9800 . ?
C613 H61H 0.9800 . ?
C7 O7 1.251(15) . ?
C8 C1 1.484(15) 2_657 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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 C1 N1 112.4(9) 2_657 . ?
C8 C1 H1A 109.1 2_657 . ?
N1 C1 H1A 109.1 . . ?
C8 C1 H1B 109.1 2_657 . ?
N1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C2 N1 C1 120.8(9) . . ?
C2 N1 H1 119.6 . . ?
C1 N1 H1 119.6 . . ?
O2 C2 N1 125.3(9) . . ?
O2 C2 C3 120.0(8) . . ?
N1 C2 C3 114.6(9) . . ?
N2 C3 C31 112.1(8) . . ?
N2 C3 C2 106.3(8) . . ?
C31 C3 C2 115.5(9) . . ?
N2 C3 H3 107.5 . . ?
C31 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C311 C31 C3 113.8(11) . . ?
C311 C31 C312 112.9(12) . . ?
C3 C31 C312 108.5(11) . . ?
C311 C31 H31 107.1 . . ?
C3 C31 H31 107.1 . . ?
C312 C31 H31 107.1 . . ?
C31 C311 H31A 109.5 . . ?
C31 C311 H31B 109.5 . . ?
H31A C311 H31B 109.5 . . ?
C31 C311 H31C 109.5 . . ?
H31A C311 H31C 109.5 . . ?
H31B C311 H31C 109.5 . . ?
C31 C312 C313 113.1(13) . . ?
C31 C312 H31D 109.0 . . ?
C313 C312 H31D 109.0 . . ?
C31 C312 H31E 109.0 . . ?
C313 C312 H31E 109.0 . . ?
H31D C312 H31E 107.8 . . ?
C312 C313 H31F 109.5 . . ?
C312 C313 H31G 109.5 . . ?
H31F C313 H31G 109.5 . . ?
C312 C313 H31H 109.5 . . ?
H31F C313 H31H 109.5 . . ?
H31G C313 H31H 109.5 . . ?
C4 N2 C3 114.8(8) . . ?
C4 N2 H2A 108.6 . . ?
C3 N2 H2A 108.6 . . ?
C4 N2 H2B 108.6 . . ?
C3 N2 H2B 108.6 . . ?
H2A N2 H2B 107.5 . . ?
N2 C4 C41 112.0(9) . . ?
N2 C4 H4A 109.2 . . ?
C41 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C41 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C42 C41 C46 118.8(9) . . ?
C42 C41 C4 120.3(13) . . ?
C46 C41 C4 120.7(12) . . ?
C41 C42 C43 120.9(11) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 119.7(10) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 117.4(8) . . ?
C45 C44 C5 122.6(11) . . ?
C43 C44 C5 119.6(11) . . ?
C46 C45 C44 123.5(11) . . ?
C46 C45 H45 118.2 . . ?
C44 C45 H45 118.2 . . ?
C45 C46 C41 119.4(11) . . ?
C45 C46 H46 120.3 . . ?
C41 C46 H46 120.3 . . ?
N3 C5 C44 116.9(9) . . ?
N3 C5 H5A 108.1 . . ?
C44 C5 H5A 108.1 . . ?
N3 C5 H5B 108.1 . . ?
C44 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C6 N3 C5 117.1(9) . . ?
C6 N3 H3A 108.0 . . ?
C5 N3 H3A 108.0 . . ?
C6 N3 H3B 108.0 . . ?
C5 N3 H3B 108.0 . . ?
H3A N3 H3B 107.3 . . ?
C7 N4 C8 121.7(10) . . ?
C7 N4 H4 119.1 . . ?
C8 N4 H4 119.1 . . ?
N3 C6 C61 111.4(9) . . ?
N3 C6 C7 107.9(9) . . ?
C61 C6 C7 112.9(10) . . ?
N3 C6 H6 108.1 . . ?
C61 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C612 C61 C611 115.3(15) . . ?
C612 C61 C6 111.2(13) . . ?
C611 C61 C6 112.9(12) . . ?
C612 C61 H61 105.5 . . ?
C611 C61 H61 105.5 . . ?
C6 C61 H61 105.5 . . ?
C61 C611 H61A 109.5 . . ?
C61 C611 H61B 109.5 . . ?
H61A C611 H61B 109.5 . . ?
C61 C611 H61C 109.5 . . ?
H61A C611 H61C 109.5 . . ?
H61B C611 H61C 109.5 . . ?
C61 C612 C613 119.1(15) . . ?
C61 C612 H61D 107.5 . . ?
C613 C612 H61D 107.5 . . ?
C61 C612 H61E 107.5 . . ?
C613 C612 H61E 107.5 . . ?
H61D C612 H61E 107.0 . . ?
C612 C613 H61F 109.5 . . ?
C612 C613 H61G 109.5 . . ?
H61F C613 H61G 109.5 . . ?
C612 C613 H61H 109.5 . . ?
H61F C613 H61H 109.5 . . ?
H61G C613 H61H 109.5 . . ?
O7 C7 N4 123.9(9) . . ?
O7 C7 C6 118.3(9) . . ?
N4 C7 C6 117.8(11) . . ?
N4 C8 C1 110.8(10) . 2_657 ?
N4 C8 H8A 109.5 . . ?
C1 C8 H8A 109.5 2_657 . ?
N4 C8 H8B 109.5 . . ?
C1 C8 H8B 109.5 2_657 . ?
H8A C8 H8B 108.1 . . ?

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
C8 C1 N1 C2 -86.9(14) 2_657 . . . ?
C1 N1 C2 O2 1.4(19) . . . . ?
C1 N1 C2 C3 176.1(10) . . . . ?
O2 C2 C3 N2 -42.0(15) . . . . ?
N1 C2 C3 N2 143.0(10) . . . . ?
O2 C2 C3 C31 83.1(14) . . . . ?
N1 C2 C3 C31 -91.9(12) . . . . ?
N2 C3 C31 C311 65.6(12) . . . . ?
C2 C3 C31 C311 -56.5(13) . . . . ?
N2 C3 C31 C312 -167.8(9) . . . . ?
C2 C3 C31 C312 70.1(13) . . . . ?
C311 C31 C312 C313 -72.6(18) . . . . ?
C3 C31 C312 C313 160.3(14) . . . . ?
C31 C3 N2 C4 167.3(10) . . . . ?
C2 C3 N2 C4 -65.5(12) . . . . ?
C3 N2 C4 C41 -145.1(11) . . . . ?
N2 C4 C41 C42 88.6(15) . . . . ?
N2 C4 C41 C46 -87.1(15) . . . . ?
C46 C41 C42 C43 0.6(19) . . . . ?
C4 C41 C42 C43 -175.2(12) . . . . ?
C41 C42 C43 C44 3(2) . . . . ?
C42 C43 C44 C45 -3.6(17) . . . . ?
C42 C43 C44 C5 170.3(12) . . . . ?
C43 C44 C45 C46 0.0(19) . . . . ?
C5 C44 C45 C46 -173.7(13) . . . . ?
C44 C45 C46 C41 4(2) . . . . ?
C42 C41 C46 C45 -4.2(18) . . . . ?
C4 C41 C46 C45 171.6(12) . . . . ?
C45 C44 C5 N3 -107.1(15) . . . . ?
C43 C44 C5 N3 79.2(15) . . . . ?
C44 C5 N3 C6 58.8(14) . . . . ?
C5 N3 C6 C61 145.1(10) . . . . ?
C5 N3 C6 C7 -90.4(10) . . . . ?
N3 C6 C61 C612 -168.7(12) . . . . ?
C7 C6 C61 C612 69.6(16) . . . . ?
N3 C6 C61 C611 59.8(14) . . . . ?
C7 C6 C61 C611 -61.8(15) . . . . ?
C611 C61 C612 C613 -66(3) . . . . ?
C6 C61 C612 C613 164(2) . . . . ?
C8 N4 C7 O7 8(2) . . . . ?
C8 N4 C7 C6 -173.9(10) . . . . ?
N3 C6 C7 O7 -42.8(15) . . . . ?
C61 C6 C7 O7 80.9(15) . . . . ?
N3 C6 C7 N4 138.6(11) . . . . ?
C61 C6 C7 N4 -97.7(14) . . . . ?
C7 N4 C8 C1 79.8(15) . . . 2_657 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2W 0.88 2.11 2.867(14) 143.8 1_545
N2 H2B Cl2 0.92 2.34 3.208(8) 156.9 4_657
N2 H2A Cl1 0.92 2.32 3.204(9) 161.6 4_657
N3 H3B O7 0.92 2.28 2.771(12) 112.7 .
N3 H3B Cl2 0.92 2.39 3.154(8) 140.7 .
N3 H3A Cl1 0.92 2.36 3.161(8) 145.9 .
N4 H4 O3W 0.88 2.07 2.837(16) 144.6 .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.142

data_miriam4
_database_code_depnum_ccdc_archive 'CCDC 706283'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;

;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H80 Cl4 N8 O6'
_chemical_formula_weight         958.96

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'
Cl Cl 0.1484 0.1585 '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   'C 2'

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

_cell_length_a                   26.413(5)
_cell_length_b                   7.1135(10)
_cell_length_c                   15.775(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.299(16)
_cell_angle_gamma                90.00
_cell_volume                     2946.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4971
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      22.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'

_exptl_special_details           
;

;

_diffrn_ambient_temperature      173(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  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14292
_diffrn_reflns_av_R_equivalents  0.2331
_diffrn_reflns_av_sigmaI/netI    0.2101
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5225
_reflns_number_gt                2281
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97

_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_number_reflns         5225
_refine_ls_number_parameters     271
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.2316
_refine_ls_R_factor_gt           0.1420
_refine_ls_wR_factor_ref         0.3527
_refine_ls_wR_factor_gt          0.3132
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.235
_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
Cl1 Cl 0.69769(9) 0.4404(6) 0.3141(2) 0.0607(8) Uani 1 1 d . . .
Cl2 Cl 0.90530(9) 0.4477(6) 0.6743(2) 0.0630(9) Uani 1 1 d . . .
O1W O 0.6686(9) -0.0082(16) 0.7374(11) 0.203(10) Uani 1 1 d . . .
H1WA H 0.6823 -0.1107 0.7532 0.304 Uiso 1 1 d R . .
H1WB H 0.6695 0.0762 0.7003 0.304 Uiso 1 1 d R . .
O1 O 0.4868(3) 0.2447(19) 0.3108(10) 0.120(5) Uani 1 1 d . . .
O2 O 0.7119(3) 0.6524(15) 0.7888(6) 0.071(3) Uani 1 1 d . . .
N1 N 0.4537(4) 0.5195(16) 0.2786(8) 0.068(3) Uani 1 1 d . . .
H1 H 0.4602 0.6363 0.2650 0.082 Uiso 1 1 calc R . .
N2 N 0.5830(3) 0.3874(14) 0.3458(6) 0.049(3) Uani 1 1 d . . .
H2A H 0.6155 0.4188 0.3354 0.059 Uiso 1 1 calc R . .
H2B H 0.5803 0.2586 0.3430 0.059 Uiso 1 1 calc R . .
N3 N 0.7916(3) 0.5022(13) 0.7045(6) 0.045(3) Uani 1 1 d . . .
H3A H 0.7832 0.6274 0.7069 0.054 Uiso 1 1 calc R . .
H3B H 0.8264 0.4932 0.7161 0.054 Uiso 1 1 calc R . .
N4 N 0.6783(4) 0.3651(16) 0.7906(7) 0.061(3) Uani 1 1 d . . .
H4 H 0.6851 0.2439 0.7917 0.073 Uiso 1 1 calc R . .
C1 C 0.4914(5) 0.4071(19) 0.2913(8) 0.058(4) Uani 1 1 d . . .
C2 C 0.5466(4) 0.470(3) 0.2774(8) 0.074(5) Uani 1 1 d . A .
H2 H 0.5494 0.6098 0.2766 0.089 Uiso 1 1 calc R . .
C3 C 0.5755(4) 0.449(3) 0.4337(8) 0.074(4) Uani 1 1 d . . .
H3C H 0.5498 0.3670 0.4563 0.088 Uiso 1 1 calc R . .
H3D H 0.5624 0.5791 0.4320 0.088 Uiso 1 1 calc R . .
C4 C 0.7768(4) 0.433(2) 0.6164(7) 0.062(3) Uani 1 1 d . . .
H4C H 0.7886 0.3013 0.6137 0.075 Uiso 1 1 calc R . .
H4D H 0.7959 0.5074 0.5775 0.075 Uiso 1 1 calc R . .
C5 C 0.7674(5) 0.399(2) 0.7731(8) 0.068(5) Uani 1 1 d . B .
H5 H 0.7629 0.2636 0.7570 0.082 Uiso 1 1 calc R . .
C6 C 0.7172(4) 0.4822(18) 0.7851(7) 0.050(3) Uani 1 1 d . . .
C7 C 0.6264(4) 0.420(3) 0.7947(8) 0.068(4) Uani 1 1 d . . .
H7A H 0.6262 0.5282 0.8343 0.081 Uiso 1 1 calc R . .
H7B H 0.6085 0.3151 0.8198 0.081 Uiso 1 1 calc R . .
C8 C 0.5980(4) 0.472(2) 0.7153(8) 0.060(4) Uani 1 1 d . . .
H8A H 0.6149 0.5802 0.6912 0.072 Uiso 1 1 calc R . .
H8B H 0.5989 0.3656 0.6750 0.072 Uiso 1 1 calc R . .
C11 C 0.6240(4) 0.440(3) 0.4919(7) 0.062(3) Uani 1 1 d . . .
C12 C 0.6521(5) 0.616(2) 0.5132(9) 0.057(4) Uani 1 1 d . . .
H12 H 0.6375 0.7334 0.4951 0.069 Uiso 1 1 calc R . .
C13 C 0.6991(5) 0.6109(18) 0.5590(9) 0.047(3) Uani 1 1 d . . .
H13 H 0.7162 0.7248 0.5756 0.057 Uiso 1 1 calc R . .
C14 C 0.7222(3) 0.437(2) 0.5817(7) 0.051(3) Uani 1 1 d . . .
C15 C 0.6950(5) 0.273(2) 0.5657(9) 0.056(4) Uani 1 1 d . . .
H15 H 0.7100 0.1565 0.5839 0.068 Uiso 1 1 calc R . .
C16 C 0.6446(5) 0.2753(19) 0.5222(9) 0.056(4) Uani 1 1 d . . .
H16 H 0.6256 0.1620 0.5146 0.067 Uiso 1 1 calc R . .
C21 C 0.5581(6) 0.382(4) 0.1891(9) 0.140(12) Uani 1 1 d D . .
H21A H 0.5244 0.3684 0.1553 0.168 Uiso 0.506(14) 1 calc PR A 1
H21B H 0.5701 0.2524 0.2027 0.168 Uiso 0.506(14) 1 calc PR A 1
H21C H 0.5952 0.3832 0.1851 0.168 Uiso 0.494(14) 1 calc PR A 2
H21D H 0.5463 0.2497 0.1853 0.168 Uiso 0.494(14) 1 calc PR A 2
C22 C 0.5933(12) 0.457(4) 0.1267(19) 0.124(6) Uiso 0.506(14) 1 d PD A 1
H22 H 0.6276 0.4742 0.1595 0.149 Uiso 0.506(14) 1 calc PR A 1
C23 C 0.5996(16) 0.311(5) 0.057(2) 0.124(6) Uiso 0.506(14) 1 d PD A 1
H23A H 0.6231 0.3590 0.0181 0.186 Uiso 0.506(14) 1 calc PR A 1
H23B H 0.5664 0.2855 0.0246 0.186 Uiso 0.506(14) 1 calc PR A 1
H23C H 0.6133 0.1938 0.0832 0.186 Uiso 0.506(14) 1 calc PR A 1
C24 C 0.5735(17) 0.654(4) 0.101(3) 0.124(6) Uiso 0.506(14) 1 d PD A 1
H24A H 0.5955 0.7099 0.0613 0.186 Uiso 0.506(14) 1 calc PR A 1
H24B H 0.5737 0.7329 0.1515 0.186 Uiso 0.506(14) 1 calc PR A 1
H24C H 0.5387 0.6441 0.0723 0.186 Uiso 0.506(14) 1 calc PR A 1
C22' C 0.5306(14) 0.496(4) 0.1154(16) 0.124(6) Uiso 0.494(14) 1 d PD A 2
H22' H 0.4947 0.4491 0.1064 0.149 Uiso 0.494(14) 1 calc PR A 2
C23' C 0.5278(17) 0.711(4) 0.127(3) 0.124(6) Uiso 0.494(14) 1 d PD A 2
H23D H 0.5102 0.7675 0.0749 0.186 Uiso 0.494(14) 1 calc PR A 2
H23E H 0.5624 0.7624 0.1369 0.186 Uiso 0.494(14) 1 calc PR A 2
H23F H 0.5091 0.7401 0.1753 0.186 Uiso 0.494(14) 1 calc PR A 2
C24' C 0.5533(15) 0.470(6) 0.0312(18) 0.124(6) Uiso 0.494(14) 1 d PD A 2
H24D H 0.5349 0.5492 -0.0127 0.186 Uiso 0.494(14) 1 calc PR A 2
H24E H 0.5502 0.3379 0.0138 0.186 Uiso 0.494(14) 1 calc PR A 2
H24F H 0.5893 0.5059 0.0387 0.186 Uiso 0.494(14) 1 calc PR A 2
C51 C 0.8052(5) 0.416(3) 0.8592(9) 0.128(9) Uani 1 1 d D . .
H51A H 0.8063 0.5481 0.8794 0.154 Uiso 0.63(3) 1 calc PR B 1
H51B H 0.8401 0.3795 0.8483 0.154 Uiso 0.63(3) 1 calc PR B 1
H51C H 0.8294 0.3100 0.8588 0.154 Uiso 0.37(3) 1 calc PR B 2
H51D H 0.8254 0.5322 0.8536 0.154 Uiso 0.37(3) 1 calc PR B 2
C52 C 0.7863(8) 0.284(3) 0.9293(12) 0.073(7) Uiso 0.63(3) 1 d PD B 1
H52 H 0.7497 0.3107 0.9350 0.087 Uiso 0.63(3) 1 calc PR B 1
C53 C 0.8192(12) 0.340(5) 1.0119(15) 0.113(13) Uiso 0.63(3) 1 d PD B 1
H53A H 0.8148 0.4745 1.0228 0.169 Uiso 0.63(3) 1 calc PR B 1
H53B H 0.8551 0.3148 1.0058 0.169 Uiso 0.63(3) 1 calc PR B 1
H53C H 0.8088 0.2670 1.0596 0.169 Uiso 0.63(3) 1 calc PR B 1
C54 C 0.7938(12) 0.071(3) 0.9146(19) 0.111(12) Uiso 0.63(3) 1 d PD B 1
H54A H 0.7727 0.0321 0.8626 0.166 Uiso 0.63(3) 1 calc PR B 1
H54B H 0.7838 0.0008 0.9634 0.166 Uiso 0.63(3) 1 calc PR B 1
H54C H 0.8297 0.0464 0.9083 0.166 Uiso 0.63(3) 1 calc PR B 1
C52' C 0.7883(9) 0.421(4) 0.9470(12) 0.044(9) Uiso 0.37(3) 1 d PD B 2
H52' H 0.7533 0.4759 0.9427 0.052 Uiso 0.37(3) 1 calc PR B 2
C53' C 0.786(4) 0.217(6) 0.982(4) 0.25(5) Uiso 0.37(3) 1 d PD B 2
H53D H 0.7732 0.2192 1.0377 0.369 Uiso 0.37(3) 1 calc PR B 2
H53E H 0.8198 0.1607 0.9865 0.369 Uiso 0.37(3) 1 calc PR B 2
H53F H 0.7625 0.1420 0.9421 0.369 Uiso 0.37(3) 1 calc PR B 2
C54' C 0.8220(18) 0.530(7) 1.014(2) 0.091(18) Uiso 0.37(3) 1 d PD B 2
H54D H 0.8078 0.5227 1.0689 0.136 Uiso 0.37(3) 1 calc PR B 2
H54E H 0.8235 0.6623 0.9967 0.136 Uiso 0.37(3) 1 calc PR B 2
H54F H 0.8564 0.4768 1.0201 0.136 Uiso 0.37(3) 1 calc PR B 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
O1W H1WA 0.8400 . ?
O1W H1WB 0.8400 . ?
O1 C1 1.205(17) . ?
O2 C6 1.221(15) . ?
N1 C1 1.276(16) . ?
N1 C8 1.419(14) 2_656 ?
N1 H1 0.8800 . ?
N2 C2 1.485(15) . ?
N2 C3 1.488(15) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N3 C4 1.486(15) . ?
N3 C5 1.507(15) . ?
N3 H3A 0.9200 . ?
N3 H3B 0.9200 . ?
N4 C6 1.332(15) . ?
N4 C7 1.435(14) . ?
N4 H4 0.8800 . ?
C1 C2 1.562(17) . ?
C2 C21 1.59(2) . ?
C2 H2 1.0000 . ?
C3 C11 1.494(15) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 C14 1.485(14) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C5 C6 1.482(16) . ?
C5 C51 1.600(19) . ?
C5 H5 1.0000 . ?
C7 C8 1.436(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.419(14) 2_656 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 C16 1.35(2) . ?
C11 C12 1.48(2) . ?
C12 C13 1.366(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.408(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(19) . ?
C15 C16 1.429(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22' 1.535(18) . ?
C21 C22 1.524(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C22 C23 1.540(19) . ?
C22 C24 1.534(19) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22' C24' 1.527(19) . ?
C22' C23' 1.542(19) . ?
C22' H22' 1.0000 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
C24' H24D 0.9800 . ?
C24' H24E 0.9800 . ?
C24' H24F 0.9800 . ?
C51 C52' 1.502(17) . ?
C51 C52 1.573(16) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 H51C 0.9900 . ?
C51 H51D 0.9900 . ?
C52 C53 1.537(18) . ?
C52 C54 1.549(17) . ?
C52 H52 1.0000 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C52' C54' 1.521(19) . ?
C52' C53' 1.55(2) . ?
C52' H52' 1.0000 . ?
C53' H53D 0.9800 . ?
C53' H53E 0.9800 . ?
C53' H53F 0.9800 . ?
C54' H54D 0.9800 . ?
C54' H54E 0.9800 . ?
C54' H54F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 141.5 . . ?
C1 N1 C8 125.3(12) . 2_656 ?
C1 N1 H1 117.3 . . ?
C8 N1 H1 117.3 2_656 . ?
C2 N2 C3 114.8(10) . . ?
C2 N2 H2A 108.6 . . ?
C3 N2 H2A 108.6 . . ?
C2 N2 H2B 108.6 . . ?
C3 N2 H2B 108.6 . . ?
H2A N2 H2B 107.5 . . ?
C4 N3 C5 114.9(10) . . ?
C4 N3 H3A 108.6 . . ?
C5 N3 H3A 108.6 . . ?
C4 N3 H3B 108.6 . . ?
C5 N3 H3B 108.6 . . ?
H3A N3 H3B 107.5 . . ?
C6 N4 C7 125.4(12) . . ?
C6 N4 H4 117.3 . . ?
C7 N4 H4 117.3 . . ?
O1 C1 N1 122.9(13) . . ?
O1 C1 C2 115.5(13) . . ?
N1 C1 C2 121.6(12) . . ?
N2 C2 C1 109.0(10) . . ?
N2 C2 C21 108.2(12) . . ?
C1 C2 C21 106.4(13) . . ?
N2 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
C21 C2 H2 111.0 . . ?
N2 C3 C11 111.5(9) . . ?
N2 C3 H3C 109.3 . . ?
C11 C3 H3C 109.3 . . ?
N2 C3 H3D 109.3 . . ?
C11 C3 H3D 109.3 . . ?
H3C C3 H3D 108.0 . . ?
N3 C4 C14 119.0(8) . . ?
N3 C4 H4C 107.6 . . ?
C14 C4 H4C 107.6 . . ?
N3 C4 H4D 107.6 . . ?
C14 C4 H4D 107.6 . . ?
H4C C4 H4D 107.0 . . ?
C6 C5 N3 110.7(10) . . ?
C6 C5 C51 110.2(12) . . ?
N3 C5 C51 107.2(10) . . ?
C6 C5 H5 109.5 . . ?
N3 C5 H5 109.5 . . ?
C51 C5 H5 109.5 . . ?
O2 C6 N4 121.6(10) . . ?
O2 C6 C5 120.7(12) . . ?
N4 C6 C5 117.7(12) . . ?
N4 C7 C8 116.2(10) . . ?
N4 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
N4 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 C7 114.7(11) 2_656 . ?
N1 C8 H8A 108.6 2_656 . ?
C7 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 2_656 . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C16 C11 C12 118.8(10) . . ?
C16 C11 C3 122.5(16) . . ?
C12 C11 C3 118.6(16) . . ?
C13 C12 C11 120.0(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.1(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.6(9) . . ?
C15 C14 C4 121.1(15) . . ?
C13 C14 C4 119.1(14) . . ?
C14 C15 C16 121.2(13) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 119.7(12) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C22' C21 C2 109.7(16) . . ?
C2 C21 C22 128(2) . . ?
C2 C21 H21A 105.2 . . ?
C22 C21 H21A 105.2 . . ?
C2 C21 H21B 105.2 . . ?
C22 C21 H21B 105.2 . . ?
H21A C21 H21B 106.0 . . ?
C22' C21 H21C 109.7 . . ?
C2 C21 H21C 109.7 . . ?
H21A C21 H21C 143.7 . . ?
H21B C21 H21C 74.1 . . ?
C22' C21 H21D 109.7 . . ?
C2 C21 H21D 109.7 . . ?
C22 C21 H21D 120.3 . . ?
H21A C21 H21D 67.5 . . ?
H21C C21 H21D 108.2 . . ?
C23 C22 C21 110(2) . . ?
C23 C22 C24 119(3) . . ?
C21 C22 C24 106(2) . . ?
C23 C22 H22 106.9 . . ?
C21 C22 H22 106.9 . . ?
C24 C22 H22 106.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24' C22' C21 113(2) . . ?
C24' C22' C23' 104(2) . . ?
C21 C22' C23' 118(3) . . ?
C24' C22' H22' 107.0 . . ?
C21 C22' H22' 107.0 . . ?
C23' C22' H22' 107.0 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C22' C24' H24D 109.5 . . ?
C22' C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C22' C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C52' C51 C5 124.2(14) . . ?
C5 C51 C52 109.5(14) . . ?
C52' C51 H51A 71.5 . . ?
C5 C51 H51A 109.8 . . ?
C52 C51 H51A 109.8 . . ?
C52' C51 H51B 122.9 . . ?
C5 C51 H51B 109.8 . . ?
C52 C51 H51B 109.8 . . ?
H51A C51 H51B 108.2 . . ?
C52' C51 H51C 106.3 . . ?
C5 C51 H51C 106.3 . . ?
C52 C51 H51C 78.7 . . ?
C52' C51 H51D 106.3 . . ?
C5 C51 H51D 106.3 . . ?
C52 C51 H51D 140.7 . . ?
H51C C51 H51D 106.4 . . ?
C53 C52 C51 104.3(17) . . ?
C53 C52 C54 108(2) . . ?
C51 C52 C54 115.0(18) . . ?
C53 C52 H52 109.8 . . ?
C51 C52 H52 109.8 . . ?
C54 C52 H52 109.8 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C51 C52' C54' 116(2) . . ?
C51 C52' C53' 109(3) . . ?
C54' C52' C53' 106(3) . . ?
C51 C52' H52' 108.3 . . ?
C54' C52' H52' 108.3 . . ?
C53' C52' H52' 108.3 . . ?
C52' C53' H53D 109.5 . . ?
C52' C53' H53E 109.5 . . ?
H53D C53' H53E 109.5 . . ?
C52' C53' H53F 109.5 . . ?
H53D C53' H53F 109.5 . . ?
H53E C53' H53F 109.5 . . ?
C52' C54' H54D 109.5 . . ?
C52' C54' H54E 109.5 . . ?
H54D C54' H54E 109.5 . . ?
C52' C54' H54F 109.5 . . ?
H54D C54' H54F 109.5 . . ?
H54E C54' H54F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 0(2) 2_656 . . . ?
C8 N1 C1 C2 176.0(12) 2_656 . . . ?
C3 N2 C2 C1 -61.7(16) . . . . ?
C3 N2 C2 C21 -177.1(14) . . . . ?
O1 C1 C2 N2 -42.6(19) . . . . ?
N1 C1 C2 N2 140.7(13) . . . . ?
O1 C1 C2 C21 73.9(17) . . . . ?
N1 C1 C2 C21 -102.9(17) . . . . ?
C2 N2 C3 C11 -153.2(14) . . . . ?
C5 N3 C4 C14 59.6(18) . . . . ?
C4 N3 C5 C6 -86.9(13) . . . . ?
C4 N3 C5 C51 152.8(12) . . . . ?
C7 N4 C6 O2 5(2) . . . . ?
C7 N4 C6 C5 -174.3(11) . . . . ?
N3 C5 C6 O2 -45.0(17) . . . . ?
C51 C5 C6 O2 73.5(16) . . . . ?
N3 C5 C6 N4 134.3(12) . . . . ?
C51 C5 C6 N4 -107.2(14) . . . . ?
C6 N4 C7 C8 79.1(19) . . . . ?
N4 C7 C8 N1 178.0(14) . . . 2_656 ?
N2 C3 C11 C16 -74.5(18) . . . . ?
N2 C3 C11 C12 102.1(15) . . . . ?
C16 C11 C12 C13 3.4(17) . . . . ?
C3 C11 C12 C13 -173.3(12) . . . . ?
C11 C12 C13 C14 3.7(18) . . . . ?
C12 C13 C14 C15 -7.1(16) . . . . ?
C12 C13 C14 C4 168.3(11) . . . . ?
N3 C4 C14 C15 -111.9(16) . . . . ?
N3 C4 C14 C13 72.7(17) . . . . ?
C13 C14 C15 C16 3.5(18) . . . . ?
C4 C14 C15 C16 -171.8(11) . . . . ?
C12 C11 C16 C15 -6.9(19) . . . . ?
C3 C11 C16 C15 169.6(12) . . . . ?
C14 C15 C16 C11 4(2) . . . . ?
N2 C2 C21 C22' -166.4(18) . . . . ?
C1 C2 C21 C22' 77(2) . . . . ?
N2 C2 C21 C22 -92(2) . . . . ?
C1 C2 C21 C22 151(2) . . . . ?
C22' C21 C22 C23 -92(3) . . . . ?
C2 C21 C22 C23 171(2) . . . . ?
C22' C21 C22 C24 38(3) . . . . ?
C2 C21 C22 C24 -59(3) . . . . ?
C2 C21 C22' C24' 159(3) . . . . ?
C22 C21 C22' C24' 35(3) . . . . ?
C2 C21 C22' C23' 37(3) . . . . ?
C22 C21 C22' C23' -87(3) . . . . ?
C6 C5 C51 C52' 29(3) . . . . ?
N3 C5 C51 C52' 149(2) . . . . ?
C6 C5 C51 C52 68.5(18) . . . . ?
N3 C5 C51 C52 -170.9(14) . . . . ?
C52' C51 C52 C53 -49(2) . . . . ?
C5 C51 C52 C53 -169.9(19) . . . . ?
C52' C51 C52 C54 -167(3) . . . . ?
C5 C51 C52 C54 72(2) . . . . ?
C5 C51 C52' C54' -150(3) . . . . ?
C52 C51 C52' C54' 132(4) . . . . ?
C5 C51 C52' C53' 89(4) . . . . ?
C52 C51 C52' C53' 12(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Cl1 0.92 2.24 3.146(9) 169.7 .
N2 H2B Cl2 0.92 2.26 3.162(11) 164.9 4_646
N3 H3A Cl1 0.92 2.32 3.147(10) 150.2 4_656
N3 H3B Cl2 0.92 2.28 3.116(9) 151.5 .
N4 H4 O1W 0.88 2.01 2.788(17) 146.0 .
O1W H1WA O2 0.84 1.92 2.755(18) 178.5 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.074
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.125

