# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

 
data_nd041b 

_publ_section_title  nd041
_publ_contact_author_name
'Jeff Baumes'

_publ_contact_author_address  '378 Stepan'

_publ_contact_author_email    jbaumes@nd.edu

_publ_contact_author_phone    1-7629

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C56 H56 N4 O4, C44 H36 N2 O2, C H Cl3, 2(H2 O)'  
_chemical_formula_sum 
 'C101 H97 Cl3 N6 O8' 
_chemical_formula_weight          1629.20 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0040   0.0020 
 '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'   0.0076   0.0040 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0133   0.0073 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1704   0.1889 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_Hall  '-P 1' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    11.1735(15) 
_cell_length_b                    11.7304(13) 
_cell_length_c                    17.822(3) 
_cell_angle_alpha                 100.460(8) 
_cell_angle_beta                  99.693(9) 
_cell_angle_gamma                 107.086(6) 
_cell_volume                      2133.7(5) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     2381
_cell_measurement_theta_min       2.42 
_cell_measurement_theta_max       22.11 
 
_exptl_crystal_description        blade
_exptl_crystal_colour             turquoise 
_exptl_crystal_size_max           0.08 
_exptl_crystal_size_mid           0.03 
_exptl_crystal_size_min           0.005 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.268 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              860 
_exptl_absorpt_coefficient_mu     0.176 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5875
_exptl_absorpt_correction_T_max   0.7458 
_exptl_absorpt_process_details    'SADABS, Sheldrick, 2008' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.77490 
_diffrn_radiation_type            synchrotron 
_diffrn_radiation_source          synchrotron 
_diffrn_radiation_monochromator   'channel-cut Si-<111> crystal' 
_diffrn_measurement_device_type   'Bruker APEX-II'
_diffrn_measurement_method        
'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             25755 
_diffrn_reflns_av_R_equivalents   0.1228 
_diffrn_reflns_av_sigmaI/netI     0.1019 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.04 
_diffrn_reflns_theta_max          24.07 
_reflns_number_total              5094 
_reflns_number_gt                 3094 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker APEX-II v2010-3' 
_computing_cell_refinement        'Bruker SAINT v7.68A' 
_computing_data_reduction         'Bruker SAINT v7.68A' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_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)+(0.1646P)²+6.0562P] 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        0.043(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          5094 
_refine_ls_number_parameters      551 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1785 
_refine_ls_R_factor_gt            0.1220 
_refine_ls_wR_factor_ref          0.3490 
_refine_ls_wR_factor_gt           0.3117 
_refine_ls_goodness_of_fit_ref    1.087 
_refine_ls_restrained_S_all       1.087 
_refine_ls_shift/su_max           0.014 
_refine_ls_shift/su_mean          0.002 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O -0.0348(5) -0.1187(5) 0.0863(3) 0.0513(15) Uani 1 1 d . . . 
N1 N 0.4282(6) 0.4614(6) 0.2804(5) 0.059(2) Uani 1 1 d . . . 
C1 C -0.0164(7) -0.0548(7) 0.0385(5) 0.042(2) Uani 1 1 d . . . 
C2 C 0.0677(7) 0.0706(7) 0.0433(5) 0.046(2) Uani 1 1 d . . . 
C3 C 0.1603(7) 0.1680(7) 0.1027(5) 0.042(2) Uani 1 1 d . . . 
C4 C 0.1954(7) 0.1571(7) 0.1793(5) 0.046(2) Uani 1 1 d . . . 
H4A H 0.1574 0.0809 0.1913 0.056 Uiso 1 1 calc R . . 
C5 C 0.2814(7) 0.2507(8) 0.2371(5) 0.051(2) Uani 1 1 d . . . 
H5A H 0.3015 0.2390 0.2885 0.061 Uiso 1 1 calc R . . 
C6 C 0.3423(7) 0.3667(8) 0.2223(6) 0.051(2) Uani 1 1 d . . . 
C7 C 0.3110(7) 0.3791(8) 0.1451(6) 0.054(2) Uani 1 1 d . . . 
H7A H 0.3513 0.4546 0.1329 0.064 Uiso 1 1 calc R . . 
C8 C 0.2216(7) 0.2821(7) 0.0864(5) 0.050(2) Uani 1 1 d . . . 
H8A H 0.2012 0.2924 0.0346 0.060 Uiso 1 1 calc R . . 
C9 C 0.4624(8) 0.4484(9) 0.3594(6) 0.069(3) Uani 1 1 d . . . 
H9A H 0.5381 0.5202 0.3899 0.082 Uiso 1 1 calc R . . 
H9B H 0.4872 0.3738 0.3577 0.082 Uiso 1 1 calc R . . 
C10 C 0.3526(9) 0.4390(8) 0.4006(6) 0.067(3) Uani 1 1 d . . . 
C11 C 0.2690(12) 0.5051(10) 0.3875(8) 0.108(4) Uani 1 1 d . . . 
H11A H 0.2797 0.5587 0.3533 0.129 Uiso 1 1 calc R . . 
C12 C 0.1706(15) 0.4900(14) 0.4261(10) 0.154(7) Uani 1 1 d . . . 
H12A H 0.1140 0.5358 0.4185 0.185 Uiso 1 1 calc R . . 
C13 C 0.1508(13) 0.4126(13) 0.4744(8) 0.117(5) Uani 1 1 d . . . 
H13A H 0.0827 0.4063 0.5006 0.140 Uiso 1 1 calc R . . 
C14 C 0.2272(10) 0.3453(10) 0.4850(6) 0.084(3) Uani 1 1 d . . . 
H14A H 0.2122 0.2892 0.5175 0.101 Uiso 1 1 calc R . . 
C15 C 0.3290(10) 0.3582(9) 0.4481(6) 0.073(3) Uani 1 1 d . . . 
H15A H 0.3834 0.3104 0.4557 0.088 Uiso 1 1 calc R . . 
C16 C 0.4923(8) 0.5793(8) 0.2628(6) 0.070(3) Uani 1 1 d . . . 
H16A H 0.5412 0.6407 0.3127 0.084 Uiso 1 1 calc R . . 
H16B H 0.4258 0.6093 0.2373 0.084 Uiso 1 1 calc R . . 
C17 C 0.5843(7) 0.5692(7) 0.2092(6) 0.063(3) Uani 1 1 d . . . 
C18 C 0.6517(8) 0.4885(8) 0.2114(6) 0.070(3) Uani 1 1 d . . . 
H18A H 0.6413 0.4365 0.2467 0.084 Uiso 1 1 calc R . . 
C19 C 0.7352(8) 0.4824(8) 0.1621(7) 0.075(3) Uani 1 1 d . . . 
H19A H 0.7804 0.4254 0.1634 0.090 Uiso 1 1 calc R . . 
C20 C 0.7526(9) 0.5585(9) 0.1116(7) 0.084(3) Uani 1 1 d . . . 
H20A H 0.8069 0.5532 0.0763 0.100 Uiso 1 1 calc R . . 
C21 C 0.6890(9) 0.6422(9) 0.1138(7) 0.088(4) Uani 1 1 d . . . 
H21A H 0.7056 0.7002 0.0827 0.106 Uiso 1 1 calc R . . 
C22 C 0.6024(9) 0.6452(9) 0.1593(7) 0.081(3) Uani 1 1 d . . . 
H22A H 0.5548 0.7000 0.1562 0.097 Uiso 1 1 calc R . . 
O2 O 0.2923(9) -0.2610(8) 0.2436(4) 0.116(3) Uani 1 1 d . . . 
O3 O -0.2197(7) -0.0215(7) 0.3236(4) 0.091(2) Uani 1 1 d . . . 
N2 N 0.1813(6) -0.1970(6) 0.1537(4) 0.0548(19) Uani 1 1 d . . . 
H2A H 0.1206 -0.1656 0.1406 0.066 Uiso 1 1 calc R . . 
N3 N -0.1578(6) -0.0222(6) 0.2109(4) 0.0550(19) Uani 1 1 d . . . 
H3A H -0.1081 -0.0412 0.1809 0.066 Uiso 1 1 calc R . . 
C23 C 0.2571(8) -0.2242(9) 0.0964(5) 0.061(2) Uani 1 1 d . . . 
H23A H 0.2312 -0.3145 0.0766 0.074 Uiso 1 1 calc R . . 
H23B H 0.3495 -0.1935 0.1236 0.074 Uiso 1 1 calc R . . 
C24 C 0.2025(9) -0.2186(8) 0.2237(6) 0.065(3) Uani 1 1 d . . . 
C25 C 0.1326(9) -0.1818(8) 0.2832(5) 0.062(2) Uani 1 1 d . . . 
C26 C 0.0243(8) -0.1355(8) 0.2498(5) 0.055(2) Uani 1 1 d . . . 
H26A H 0.0611 -0.0655 0.2273 0.066 Uiso 1 1 calc R . . 
H26B H -0.0400 -0.2022 0.2068 0.066 Uiso 1 1 calc R . . 
C27 C -0.0428(8) -0.0948(8) 0.3121(5) 0.057(2) Uani 1 1 d . . . 
C28 C 0.0691(12) -0.2923(10) 0.3142(7) 0.092(4) Uani 1 1 d . . . 
H28A H 0.0092 -0.3595 0.2698 0.111 Uiso 1 1 calc R . . 
H28B H 0.1362 -0.3225 0.3386 0.111 Uiso 1 1 calc R . . 
C29 C -0.0031(15) -0.2593(14) 0.3731(9) 0.109(5) Uani 1 1 d . . . 
H29A H -0.0450 -0.3343 0.3907 0.131 Uiso 1 1 calc R . . 
C30 C -0.1040(10) -0.2085(9) 0.3425(7) 0.080(3) Uani 1 1 d . . . 
H30A H -0.1456 -0.1848 0.3849 0.097 Uiso 1 1 calc R . . 
H30B H -0.1711 -0.2722 0.2993 0.097 Uiso 1 1 calc R . . 
C31 C 0.2274(10) -0.0794(12) 0.3515(7) 0.097(4) Uani 1 1 d . . . 
H31A H 0.2631 -0.0050 0.3327 0.116 Uiso 1 1 calc R . . 
H31B H 0.2997 -0.1059 0.3728 0.116 Uiso 1 1 calc R . . 
C32 C 0.1578(11) -0.0485(15) 0.4177(8) 0.124(6) Uani 1 1 d . . . 
H32A H 0.2212 0.0145 0.4638 0.149 Uiso 1 1 calc R . . 
C33 C 0.0929(18) -0.164(2) 0.4428(10) 0.136(6) Uani 1 1 d . . . 
H33A H 0.1588 -0.1980 0.4647 0.163 Uiso 1 1 calc R . . 
H33B H 0.0483 -0.1439 0.4842 0.163 Uiso 1 1 calc R . . 
C34 C 0.0550(10) 0.0063(10) 0.3802(7) 0.101(4) Uani 1 1 d . . . 
H34A H 0.0109 0.0339 0.4200 0.121 Uiso 1 1 calc R . . 
H34B H 0.0982 0.0779 0.3608 0.121 Uiso 1 1 calc R . . 
C35 C -0.1483(9) -0.0456(8) 0.2815(6) 0.063(3) Uani 1 1 d . . . 
C36 C -0.2519(9) 0.0358(9) 0.1829(6) 0.067(3) Uani 1 1 d . . . 
H36A H -0.2427 0.1084 0.2246 0.080 Uiso 1 1 calc R . . 
H36B H -0.3399 -0.0232 0.1742 0.080 Uiso 1 1 calc R . . 
C37 C -0.2377(8) 0.0753(8) 0.1095(6) 0.055(2) Uani 1 1 d . . . 
C38 C -0.1514(7) 0.1931(8) 0.1131(5) 0.048(2) Uani 1 1 d . . . 
C39 C -0.0622(9) 0.2692(9) 0.1834(6) 0.062(3) Uani 1 1 d . . . 
H39A H -0.0592 0.2404 0.2300 0.074 Uiso 1 1 calc R . . 
C40 C 0.0195(8) 0.3827(9) 0.1858(6) 0.065(3) Uani 1 1 d . . . 
H40A H 0.0775 0.4322 0.2338 0.078 Uiso 1 1 calc R . . 
C41 C 0.0183(8) 0.4268(8) 0.1178(7) 0.059(2) Uani 1 1 d . . . 
H41A H 0.0757 0.5058 0.1198 0.071 Uiso 1 1 calc R . . 
C42 C -0.0629(8) 0.3585(8) 0.0507(6) 0.052(2) Uani 1 1 d . . . 
H42A H -0.0608 0.3906 0.0055 0.062 Uiso 1 1 calc R . . 
C43 C -0.1534(7) 0.2393(7) 0.0424(6) 0.050(2) Uani 1 1 d . . . 
C44 C -0.2400(7) 0.1678(8) -0.0282(5) 0.047(2) Uani 1 1 d . . . 
C45 C -0.3171(7) 0.0470(8) -0.0320(6) 0.050(2) Uani 1 1 d . . . 
C46 C -0.3997(9) -0.0306(9) -0.1028(6) 0.066(3) Uani 1 1 d . . . 
H46A H -0.4024 -0.0005 -0.1489 0.079 Uiso 1 1 calc R . . 
C47 C -0.4781(9) -0.1508(10) -0.1082(8) 0.080(3) Uani 1 1 d . . . 
H47A H -0.5324 -0.2019 -0.1570 0.096 Uiso 1 1 calc R . . 
C48 C -0.4744(11) -0.1937(11) -0.0402(9) 0.083(3) Uani 1 1 d . . . 
H48A H -0.5271 -0.2751 -0.0431 0.100 Uiso 1 1 calc R . . 
C49 C -0.3977(10) -0.1223(9) 0.0303(8) 0.073(3) Uani 1 1 d . . . 
H49A H -0.3982 -0.1537 0.0758 0.088 Uiso 1 1 calc R . . 
C50 C -0.3154(8) 0.0010(7) 0.0362(6) 0.050(2) Uani 1 1 d . . . 
C1S C 0.3511(17) 0.824(2) 0.6188(13) 0.090(7) Uani 0.50 1 d P . . 
H1SA H 0.3160 0.8932 0.6221 0.108 Uiso 0.50 1 calc PR . . 
Cl1 Cl 0.4644(5) 0.8652(6) 0.6968(3) 0.0845(17) Uani 0.50 1 d P . . 
Cl2 Cl 0.4212(7) 0.8248(10) 0.5323(3) 0.154(4) Uani 0.50 1 d P . . 
Cl3 Cl 0.2222(8) 0.6986(6) 0.6156(5) 0.133(3) Uani 0.50 1 d P . . 
O1S O -0.4496(11) -0.1368(9) 0.3744(8) 0.196(6) 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 
O1 C1 1.238(8) . ? 
N1 C6 1.359(10) . ? 
N1 C9 1.442(11) . ? 
N1 C16 1.475(11) . ? 
C1 C2 1.429(11) 2 ? 
C1 C2 1.472(11) . ? 
C2 C3 1.413(11) . ? 
C2 C1 1.429(11) 2 ? 
C3 C4 1.395(11) . ? 
C3 C8 1.419(10) . ? 
C4 C5 1.351(11) . ? 
C5 C6 1.425(11) . ? 
C6 C7 1.407(12) . ? 
C7 C8 1.391(11) . ? 
C9 C10 1.521(12) . ? 
C10 C15 1.380(13) . ? 
C10 C11 1.394(14) . ? 
C11 C12 1.378(14) . ? 
C12 C13 1.358(15) . ? 
C13 C14 1.336(14) . ? 
C14 C15 1.392(13) . ? 
C16 C17 1.531(12) . ? 
C17 C22 1.367(13) . ? 
C17 C18 1.374(11) . ? 
C18 C19 1.392(12) . ? 
C19 C20 1.377(13) . ? 
C20 C21 1.369(13) . ? 
C21 C22 1.366(13) . ? 
O2 C24 1.271(10) . ? 
O3 C35 1.239(9) . ? 
N2 C24 1.315(10) . ? 
N2 C23 1.481(10) . ? 
N3 C35 1.330(10) . ? 
N3 C36 1.477(10) . ? 
C23 C44 1.496(11) 2 ? 
C24 C25 1.493(12) . ? 
C25 C31 1.528(14) . ? 
C25 C28 1.530(13) . ? 
C25 C26 1.540(11) . ? 
C26 C27 1.524(11) . ? 
C27 C35 1.521(12) . ? 
C27 C34 1.531(13) . ? 
C27 C30 1.547(12) . ? 
C28 C29 1.492(14) . ? 
C29 C30 1.494(14) . ? 
C29 C33 1.51(2) . ? 
C31 C32 1.565(15) . ? 
C32 C33 1.52(2) . ? 
C32 C34 1.585(17) . ? 
C36 C37 1.484(12) . ? 
C37 C50 1.407(12) . ? 
C37 C38 1.417(11) . ? 
C38 C39 1.418(12) . ? 
C38 C43 1.459(11) . ? 
C39 C40 1.364(12) . ? 
C40 C41 1.401(13) . ? 
C41 C42 1.324(12) . ? 
C42 C43 1.430(11) . ? 
C43 C44 1.397(11) . ? 
C44 C45 1.409(11) . ? 
C44 C23 1.496(11) 2 ? 
C45 C46 1.404(12) . ? 
C45 C50 1.415(11) . ? 
C46 C47 1.401(13) . ? 
C47 C48 1.393(15) . ? 
C48 C49 1.359(14) . ? 
C49 C50 1.441(13) . ? 
C1S Cl1 1.60(2) . ? 
C1S Cl3 1.71(2) . ? 
C1S Cl2 1.84(2) . ? 
C4 H4A 0.9500 . ? 
C5 H5A 0.9500 . ? 
C7 H7A 0.9500 . ? 
C8 H8A 0.9500 . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C11 H11A 0.9500 . ? 
C12 H12A 0.9500 . ? 
C13 H13A 0.9500 . ? 
C14 H14A 0.9500 . ? 
C15 H15A 0.9500 . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C18 H18A 0.9500 . ? 
C19 H19A 0.9500 . ? 
C20 H20A 0.9500 . ? 
C21 H21A 0.9500 . ? 
C22 H22A 0.9500 . ? 
N2 H2A 0.8800 . ? 
N3 H3A 0.8800 . ? 
C23 H23A 0.9900 . ? 
C23 H23B 0.9900 . ? 
C26 H26A 0.9900 . ? 
C26 H26B 0.9900 . ? 
C28 H28A 0.9900 . ? 
C28 H28B 0.9900 . ? 
C29 H29A 1.0000 . ? 
C30 H30A 0.9900 . ? 
C30 H30B 0.9900 . ? 
C31 H31A 0.9900 . ? 
C31 H31B 0.9900 . ? 
C32 H32A 1.0000 . ? 
C33 H33A 0.9900 . ? 
C33 H33B 0.9900 . ? 
C34 H34A 0.9900 . ? 
C34 H34B 0.9900 . ? 
C36 H36A 0.9900 . ? 
C36 H36B 0.9900 . ? 
C39 H39A 0.9500 . ? 
C40 H40A 0.9500 . ? 
C41 H41A 0.9500 . ? 
C42 H42A 0.9500 . ? 
C46 H46A 0.9500 . ? 
C47 H47A 0.9500 . ? 
C48 H48A 0.9500 . ? 
C49 H49A 0.9500 . ? 
C1S H1SA 1.0000 . ? 
 
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 
C6 N1 C9 121.5(7) . . ? 
C6 N1 C16 120.1(8) . . ? 
C9 N1 C16 118.4(8) . . ? 
O1 C1 C2 135.4(7) . 2 ? 
O1 C1 C2 134.4(8) . . ? 
C2 C1 C2 90.2(7) 2 . ? 
C3 C2 C1 134.1(7) . 2 ? 
C3 C2 C1 136.1(8) . . ? 
C1 C2 C1 89.8(7) 2 . ? 
C4 C3 C2 122.1(7) . . ? 
C4 C3 C8 117.2(8) . . ? 
C2 C3 C8 120.7(8) . . ? 
C5 C4 C3 122.6(7) . . ? 
C4 C5 C6 121.1(8) . . ? 
N1 C6 C7 121.2(8) . . ? 
N1 C6 C5 121.4(8) . . ? 
C7 C6 C5 117.4(8) . . ? 
C8 C7 C6 120.8(8) . . ? 
C7 C8 C3 120.9(8) . . ? 
N1 C9 C10 112.3(8) . . ? 
C15 C10 C11 118.7(9) . . ? 
C15 C10 C9 120.0(9) . . ? 
C11 C10 C9 121.1(9) . . ? 
C12 C11 C10 117.7(10) . . ? 
C13 C12 C11 122.9(11) . . ? 
C14 C13 C12 120.0(11) . . ? 
C13 C14 C15 119.3(10) . . ? 
C10 C15 C14 121.4(9) . . ? 
N1 C16 C17 113.0(7) . . ? 
C22 C17 C18 119.2(8) . . ? 
C22 C17 C16 118.9(8) . . ? 
C18 C17 C16 121.9(9) . . ? 
C17 C18 C19 120.3(9) . . ? 
C20 C19 C18 120.4(8) . . ? 
C21 C20 C19 117.7(9) . . ? 
C22 C21 C20 122.3(10) . . ? 
C21 C22 C17 119.9(9) . . ? 
C24 N2 C23 121.6(6) . . ? 
C35 N3 C36 120.0(7) . . ? 
N2 C23 C44 113.3(6) . 2 ? 
O2 C24 N2 119.3(8) . . ? 
O2 C24 C25 119.3(8) . . ? 
N2 C24 C25 121.0(7) . . ? 
C24 C25 C31 109.7(8) . . ? 
C24 C25 C28 109.9(7) . . ? 
C31 C25 C28 109.2(9) . . ? 
C24 C25 C26 113.2(7) . . ? 
C31 C25 C26 108.1(7) . . ? 
C28 C25 C26 106.6(8) . . ? 
C27 C26 C25 112.3(7) . . ? 
C35 C27 C26 113.7(7) . . ? 
C35 C27 C34 107.7(7) . . ? 
C26 C27 C34 110.3(7) . . ? 
C35 C27 C30 108.5(7) . . ? 
C26 C27 C30 107.2(7) . . ? 
C34 C27 C30 109.4(8) . . ? 
C29 C28 C25 111.4(8) . . ? 
C28 C29 C30 113.5(10) . . ? 
C28 C29 C33 107.9(12) . . ? 
C30 C29 C33 108.9(11) . . ? 
C29 C30 C27 110.0(9) . . ? 
C25 C31 C32 110.1(9) . . ? 
C33 C32 C31 110.3(11) . . ? 
C33 C32 C34 111.2(10) . . ? 
C31 C32 C34 105.3(12) . . ? 
C29 C33 C32 109.9(12) . . ? 
C27 C34 C32 108.0(8) . . ? 
O3 C35 N3 120.5(8) . . ? 
O3 C35 C27 120.4(8) . . ? 
N3 C35 C27 119.0(7) . . ? 
N3 C36 C37 114.2(6) . . ? 
C50 C37 C38 119.1(8) . . ? 
C50 C37 C36 120.9(8) . . ? 
C38 C37 C36 119.8(9) . . ? 
C37 C38 C39 122.5(8) . . ? 
C37 C38 C43 119.4(9) . . ? 
C39 C38 C43 118.1(8) . . ? 
C40 C39 C38 121.6(9) . . ? 
C39 C40 C41 120.4(9) . . ? 
C42 C41 C40 120.1(9) . . ? 
C41 C42 C43 123.8(9) . . ? 
C44 C43 C42 123.8(8) . . ? 
C44 C43 C38 120.2(7) . . ? 
C42 C43 C38 116.1(9) . . ? 
C43 C44 C45 119.3(8) . . ? 
C43 C44 C23 119.5(8) . 2 ? 
C45 C44 C23 121.1(8) . 2 ? 
C46 C45 C44 121.2(9) . . ? 
C46 C45 C50 118.0(8) . . ? 
C44 C45 C50 120.8(8) . . ? 
C47 C46 C45 122.5(10) . . ? 
C48 C47 C46 118.3(11) . . ? 
C49 C48 C47 121.9(11) . . ? 
C48 C49 C50 120.2(11) . . ? 
C37 C50 C45 120.7(8) . . ? 
C37 C50 C49 120.1(9) . . ? 
C45 C50 C49 119.2(10) . . ? 
Cl1 C1S Cl3 114.5(15) . . ? 
Cl1 C1S Cl2 109.5(9) . . ? 
Cl3 C1S Cl2 118.3(12) . . ? 
C5 C4 H4A 118.7 . . ? 
C3 C4 H4A 118.7 . . ? 
C4 C5 H5A 119.5 . . ? 
C6 C5 H5A 119.5 . . ? 
C8 C7 H7A 119.6 . . ? 
C6 C7 H7A 119.6 . . ? 
C7 C8 H8A 119.5 . . ? 
C3 C8 H8A 119.6 . . ? 
N1 C9 H9A 109.1 . . ? 
C10 C9 H9A 109.1 . . ? 
N1 C9 H9B 109.1 . . ? 
C10 C9 H9B 109.1 . . ? 
H9A C9 H9B 107.9 . . ? 
C12 C11 H11A 121.2 . . ? 
C10 C11 H11A 121.2 . . ? 
C13 C12 H12A 118.6 . . ? 
C11 C12 H12A 118.6 . . ? 
C14 C13 H13A 120.0 . . ? 
C12 C13 H13A 120.0 . . ? 
C13 C14 H14A 120.3 . . ? 
C15 C14 H14A 120.3 . . ? 
C10 C15 H15A 119.3 . . ? 
C14 C15 H15A 119.3 . . ? 
N1 C16 H16A 109.0 . . ? 
C17 C16 H16A 109.0 . . ? 
N1 C16 H16B 109.0 . . ? 
C17 C16 H16B 109.0 . . ? 
H16A C16 H16B 107.8 . . ? 
C17 C18 H18A 119.8 . . ? 
C19 C18 H18A 119.8 . . ? 
C20 C19 H19A 119.8 . . ? 
C18 C19 H19A 119.8 . . ? 
C21 C20 H20A 121.1 . . ? 
C19 C20 H20A 121.1 . . ? 
C22 C21 H21A 118.8 . . ? 
C20 C21 H21A 118.8 . . ? 
C21 C22 H22A 120.1 . . ? 
C17 C22 H22A 120.1 . . ? 
C24 N2 H2A 119.2 . . ? 
C23 N2 H2A 119.2 . . ? 
C35 N3 H3A 120.0 . . ? 
C36 N3 H3A 120.0 . . ? 
N2 C23 H23A 108.9 . . ? 
C44 C23 H23A 108.9 2 . ? 
N2 C23 H23B 108.9 . . ? 
C44 C23 H23B 108.9 2 . ? 
H23A C23 H23B 107.7 . . ? 
C27 C26 H26A 109.2 . . ? 
C25 C26 H26A 109.1 . . ? 
C27 C26 H26B 109.1 . . ? 
C25 C26 H26B 109.1 . . ? 
H26A C26 H26B 107.9 . . ? 
C29 C28 H28A 109.3 . . ? 
C25 C28 H28A 109.3 . . ? 
C29 C28 H28B 109.3 . . ? 
C25 C28 H28B 109.3 . . ? 
H28A C28 H28B 108.0 . . ? 
C28 C29 H29A 108.8 . . ? 
C30 C29 H29A 108.8 . . ? 
C33 C29 H29A 108.8 . . ? 
C29 C30 H30A 109.7 . . ? 
C27 C30 H30A 109.7 . . ? 
C29 C30 H30B 109.7 . . ? 
C27 C30 H30B 109.7 . . ? 
H30A C30 H30B 108.2 . . ? 
C25 C31 H31A 109.6 . . ? 
C32 C31 H31A 109.6 . . ? 
C25 C31 H31B 109.6 . . ? 
C32 C31 H31B 109.6 . . ? 
H31A C31 H31B 108.2 . . ? 
C33 C32 H32A 110.0 . . ? 
C31 C32 H32A 110.0 . . ? 
C34 C32 H32A 110.0 . . ? 
C29 C33 H33A 109.7 . . ? 
C32 C33 H33A 109.7 . . ? 
C29 C33 H33B 109.7 . . ? 
C32 C33 H33B 109.7 . . ? 
H33A C33 H33B 108.2 . . ? 
C27 C34 H34A 110.1 . . ? 
C32 C34 H34A 110.1 . . ? 
C27 C34 H34B 110.1 . . ? 
C32 C34 H34B 110.1 . . ? 
H34A C34 H34B 108.4 . . ? 
N3 C36 H36A 108.7 . . ? 
C37 C36 H36A 108.7 . . ? 
N3 C36 H36B 108.7 . . ? 
C37 C36 H36B 108.7 . . ? 
H36A C36 H36B 107.6 . . ? 
C40 C39 H39A 119.2 . . ? 
C38 C39 H39A 119.2 . . ? 
C39 C40 H40A 119.8 . . ? 
C41 C40 H40A 119.8 . . ? 
C42 C41 H41A 120.0 . . ? 
C40 C41 H41A 120.0 . . ? 
C41 C42 H42A 118.1 . . ? 
C43 C42 H42A 118.1 . . ? 
C47 C46 H46A 118.8 . . ? 
C45 C46 H46A 118.8 . . ? 
C48 C47 H47A 120.9 . . ? 
C46 C47 H47A 120.9 . . ? 
C49 C48 H48A 119.1 . . ? 
C47 C48 H48A 119.0 . . ? 
C48 C49 H49A 119.9 . . ? 
C50 C49 H49A 119.9 . . ? 
Cl1 C1S H1SA 104.3 . . ? 
Cl3 C1S H1SA 104.3 . . ? 
Cl2 C1S H1SA 104.3 . . ? 
 
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 
O1 C1 C2 C3 0.2(13) . . . . ? 
C2 C1 C2 C3 179.6(9) 2 . . . ? 
O1 C1 C2 C1 -179.5(10) . . . 2 ? 
C2 C1 C2 C1 0.0 2 . . 2 ? 
C1 C2 C3 C4 -178.2(7) 2 . . . ? 
C1 C2 C3 C4 2.3(12) . . . . ? 
C1 C2 C3 C8 2.0(11) 2 . . . ? 
C1 C2 C3 C8 -177.5(7) . . . . ? 
C2 C3 C4 C5 -178.2(6) . . . . ? 
C8 C3 C4 C5 1.6(10) . . . . ? 
C3 C4 C5 C6 -0.6(11) . . . . ? 
C9 N1 C6 C7 -178.9(7) . . . . ? 
C16 N1 C6 C7 -1.0(10) . . . . ? 
C9 N1 C6 C5 0.6(10) . . . . ? 
C16 N1 C6 C5 178.4(7) . . . . ? 
C4 C5 C6 N1 179.6(7) . . . . ? 
C4 C5 C6 C7 -1.0(10) . . . . ? 
N1 C6 C7 C8 -179.1(6) . . . . ? 
C5 C6 C7 C8 1.4(10) . . . . ? 
C6 C7 C8 C3 -0.4(10) . . . . ? 
C4 C3 C8 C7 -1.1(10) . . . . ? 
C2 C3 C8 C7 178.7(6) . . . . ? 
C6 N1 C9 C10 -70.3(10) . . . . ? 
C16 N1 C9 C10 111.9(8) . . . . ? 
N1 C9 C10 C15 140.2(9) . . . . ? 
N1 C9 C10 C11 -35.7(13) . . . . ? 
C15 C10 C11 C12 3.0(19) . . . . ? 
C9 C10 C11 C12 178.9(12) . . . . ? 
C10 C11 C12 C13 -1(3) . . . . ? 
C11 C12 C13 C14 -1(3) . . . . ? 
C12 C13 C14 C15 2(2) . . . . ? 
C11 C10 C15 C14 -2.4(16) . . . . ? 
C9 C10 C15 C14 -178.4(9) . . . . ? 
C13 C14 C15 C10 -0.1(17) . . . . ? 
C6 N1 C16 C17 -66.8(10) . . . . ? 
C9 N1 C16 C17 111.0(9) . . . . ? 
N1 C16 C17 C22 149.3(9) . . . . ? 
N1 C16 C17 C18 -32.4(13) . . . . ? 
C22 C17 C18 C19 -1.4(14) . . . . ? 
C16 C17 C18 C19 -179.6(8) . . . . ? 
C17 C18 C19 C20 1.0(15) . . . . ? 
C18 C19 C20 C21 2.3(16) . . . . ? 
C19 C20 C21 C22 -5.4(18) . . . . ? 
C20 C21 C22 C17 5.1(18) . . . . ? 
C18 C17 C22 C21 -1.6(15) . . . . ? 
C16 C17 C22 C21 176.7(9) . . . . ? 
C24 N2 C23 C44 -166.9(8) . . . 2 ? 
C23 N2 C24 O2 1.8(14) . . . . ? 
C23 N2 C24 C25 175.2(8) . . . . ? 
O2 C24 C25 C31 60.7(12) . . . . ? 
N2 C24 C25 C31 -112.7(10) . . . . ? 
O2 C24 C25 C28 -59.3(13) . . . . ? 
N2 C24 C25 C28 127.2(10) . . . . ? 
O2 C24 C25 C26 -178.4(9) . . . . ? 
N2 C24 C25 C26 8.1(13) . . . . ? 
C24 C25 C26 C27 -178.2(8) . . . . ? 
C31 C25 C26 C27 -56.5(10) . . . . ? 
C28 C25 C26 C27 60.8(10) . . . . ? 
C25 C26 C27 C35 178.6(7) . . . . ? 
C25 C26 C27 C34 57.6(10) . . . . ? 
C25 C26 C27 C30 -61.5(10) . . . . ? 
C24 C25 C28 C29 -179.3(10) . . . . ? 
C31 C25 C28 C29 60.3(12) . . . . ? 
C26 C25 C28 C29 -56.3(12) . . . . ? 
C25 C28 C29 C30 57.1(16) . . . . ? 
C25 C28 C29 C33 -63.7(13) . . . . ? 
C28 C29 C30 C27 -56.7(15) . . . . ? 
C33 C29 C30 C27 63.5(12) . . . . ? 
C35 C27 C30 C29 -179.9(9) . . . . ? 
C26 C27 C30 C29 56.9(11) . . . . ? 
C34 C27 C30 C29 -62.7(11) . . . . ? 
C24 C25 C31 C32 -174.8(10) . . . . ? 
C28 C25 C31 C32 -54.3(12) . . . . ? 
C26 C25 C31 C32 61.3(12) . . . . ? 
C25 C31 C32 C33 54.8(15) . . . . ? 
C25 C31 C32 C34 -65.4(13) . . . . ? 
C28 C29 C33 C32 62.4(12) . . . . ? 
C30 C29 C33 C32 -61.2(13) . . . . ? 
C31 C32 C33 C29 -58.6(14) . . . . ? 
C34 C32 C33 C29 57.8(13) . . . . ? 
C35 C27 C34 C32 174.5(9) . . . . ? 
C26 C27 C34 C32 -60.9(11) . . . . ? 
C30 C27 C34 C32 56.7(11) . . . . ? 
C33 C32 C34 C27 -55.7(14) . . . . ? 
C31 C32 C34 C27 63.8(12) . . . . ? 
C36 N3 C35 O3 1.5(13) . . . . ? 
C36 N3 C35 C27 -174.6(8) . . . . ? 
C26 C27 C35 O3 172.3(8) . . . . ? 
C34 C27 C35 O3 -65.2(11) . . . . ? 
C30 C27 C35 O3 53.2(12) . . . . ? 
C26 C27 C35 N3 -11.6(12) . . . . ? 
C34 C27 C35 N3 110.9(9) . . . . ? 
C30 C27 C35 N3 -130.8(9) . . . . ? 
C35 N3 C36 C37 170.5(8) . . . . ? 
N3 C36 C37 C50 97.6(9) . . . . ? 
N3 C36 C37 C38 -86.9(9) . . . . ? 
C50 C37 C38 C39 -174.5(7) . . . . ? 
C36 C37 C38 C39 9.9(10) . . . . ? 
C50 C37 C38 C43 5.7(9) . . . . ? 
C36 C37 C38 C43 -169.9(6) . . . . ? 
C37 C38 C39 C40 -179.5(7) . . . . ? 
C43 C38 C39 C40 0.3(10) . . . . ? 
C38 C39 C40 C41 -0.8(11) . . . . ? 
C39 C40 C41 C42 0.3(11) . . . . ? 
C40 C41 C42 C43 0.7(11) . . . . ? 
C41 C42 C43 C44 179.3(7) . . . . ? 
C41 C42 C43 C38 -1.1(10) . . . . ? 
C37 C38 C43 C44 0.0(9) . . . . ? 
C39 C38 C43 C44 -179.8(6) . . . . ? 
C37 C38 C43 C42 -179.6(6) . . . . ? 
C39 C38 C43 C42 0.6(9) . . . . ? 
C42 C43 C44 C45 174.2(6) . . . . ? 
C38 C43 C44 C45 -5.4(10) . . . . ? 
C42 C43 C44 C23 -10.9(10) . . . 2 ? 
C38 C43 C44 C23 169.5(6) . . . 2 ? 
C43 C44 C45 C46 -176.1(6) . . . . ? 
C23 C44 C45 C46 9.1(10) 2 . . . ? 
C43 C44 C45 C50 5.1(10) . . . . ? 
C23 C44 C45 C50 -169.7(7) 2 . . . ? 
C44 C45 C46 C47 -179.6(7) . . . . ? 
C50 C45 C46 C47 -0.8(10) . . . . ? 
C45 C46 C47 C48 0.8(11) . . . . ? 
C46 C47 C48 C49 0.1(13) . . . . ? 
C47 C48 C49 C50 -0.9(13) . . . . ? 
C38 C37 C50 C45 -6.1(10) . . . . ? 
C36 C37 C50 C45 169.5(6) . . . . ? 
C38 C37 C50 C49 175.9(6) . . . . ? 
C36 C37 C50 C49 -8.6(10) . . . . ? 
C46 C45 C50 C37 -178.1(6) . . . . ? 
C44 C45 C50 C37 0.7(10) . . . . ? 
C46 C45 C50 C49 0.0(10) . . . . ? 
C44 C45 C50 C49 178.8(6) . . . . ? 
C48 C49 C50 C37 178.9(7) . . . . ? 
C48 C49 C50 C45 0.8(11) . . . . ? 
 
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 O1  0.88 2.11 2.974(8) 167.8 . 
N3 H3A O1  0.88 2.16 3.021(8) 164.7 . 
 
_diffrn_measured_fraction_theta_max    0.975 
_diffrn_reflns_theta_full              24.07 
_diffrn_measured_fraction_theta_full   0.975 
_refine_diff_density_max    1.072 
_refine_diff_density_min   -0.359 
_refine_diff_density_rms    0.119 

_vrf_THETM01_nd041b
;
RESPONSE: Use of synchrotron-intensity radiation failed to produce
data higher than 0.9 \%A in resolution.  The real, diffracted 
resolution of the sample was 1.0 \%A.  Only connectivity is
confirmed by these data.
;

_vrf_PLAT306_nd041b
;
RESPONSE: O1S is a water of crystallization.  The data are not of
sufficient quality to locate or predict hydrogen atom locations.
However, the hydrogen count has been adjusted to account for these
missing hydrogens yielding several other mninor alerts below.
;
