# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 188/189
 
data_nrb9810 
  
_audit_creation_method            'manual editing of SHELXL-97 template'

_publ_contact_author_name         'Dr Neil R Branda'
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton Alberta T6G 2G2
  Canada
;
_publ_contact_author_email        neil.branda@ualberta.ca
_publ_contact_author_fax          '+1 780 492 8231'
_publ_contact_author_phone        '+1 780 492 8187'
_publ_contact_letter
; Please accept the following CIF data which are being submitted
  in support of an upcoming communication to be published in
  Perkin 2 (manuscript 9/04223C).  Please forward any questions
  concerning this CIF to Neil Branda (neil.branda@ualberta.ca).
;
_publ_requested_journal
 'Journal of the Chemical Society: Perkin Transactions 2'
_publ_section_title
; Tautomerism of 4-Hydroxyterpyridine in the Solid, Solution and
  Gas Phases: an X-ray, FT-IR and NMR study
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
 'Murguly, Elisa' .
; Department of Chemistry
  University of Alberta
  Edmonton Alberta T6G 2G2
  Canada
;
 'Norsten, Tyler B.' .
; Department of Chemistry
  University of Alberta
  Edmonton Alberta T6G 2G2
  Canada
;
 'Branda, Neil' .
; Department of Chemistry
  University of Alberta
  Edmonton Alberta T6G 2G2
  Canada
;
_chemical_formula_sum             'C15.50 H11.50 Cl1.50 N3 O' 
_chemical_formula_weight          308.95 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0181    .0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'    .0311    .0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'    .0492    .0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'    .3639    .7018 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    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                    13.0933(5) 
_cell_length_b                    23.0093(8) 
_cell_length_c                    10.3128(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  111.328(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      2894.1(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     213(2) 
_cell_measurement_reflns_used     40 
_cell_measurement_theta_min       26.57 
_cell_measurement_theta_max       28.45 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.48 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.06 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.418 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1272 
_exptl_absorpt_coefficient_mu     3.202 
_exptl_absorpt_correction_type    integration 
_exptl_absorpt_correction_T_min   .5054 
_exptl_absorpt_correction_T_max   .8289 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       213(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuKa 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Siemens P4' 
_diffrn_measurement_method        '2\q/\w scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  297 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4062 
_diffrn_reflns_av_R_equivalents   0.0277 
_diffrn_reflns_av_sigmaI/netI     0.0486 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -1 
_diffrn_reflns_limit_k_max        25 
_diffrn_reflns_limit_l_min        -1 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          3.62 
_diffrn_reflns_theta_max          57.49 
_reflns_number_total              3801 
_reflns_number_observed           2748 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens SHELXTL' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   'Siemens SHELXTL' 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R 
 are based on F, with F set to zero for negative F^2^. The observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[s^2^(Fo^2^)+( 0.0439P)^2^+3.5258P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3801 
_refine_ls_number_parameters      379 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0875 
_refine_ls_R_factor_obs           0.0595 
_refine_ls_wR_factor_all          0.1415 
_refine_ls_wR_factor_obs          0.1241 
_refine_ls_goodness_of_fit_all    1.059 
_refine_ls_goodness_of_fit_obs    1.114 
_refine_ls_restrained_S_all       1.059 
_refine_ls_restrained_S_obs       1.114 
_refine_ls_shift/esd_max          0.004 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1A O 0.3819(2) 0.07596(12) -0.1744(3) 0.0439(7) Uani 1 d . . 
H1OA H 0.4019(2) 0.07041(12) -0.0892(3) 0.066 Uiso 1 calc R . 
N1A N 0.6204(2) 0.16235(13) -0.2748(3) 0.0317(8) Uani 1 d . . 
N2A N 0.4157(3) 0.1439(2) -0.6166(4) 0.0472(10) Uani 1 d . . 
N3A N 0.7547(3) 0.16774(15) 0.0972(4) 0.0426(9) Uani 1 d . . 
C1A C 0.5243(3) 0.1463(2) -0.3730(4) 0.0324(9) Uani 1 d . . 
C2A C 0.4435(3) 0.1175(2) -0.3395(4) 0.0342(10) Uani 1 d . . 
H2A H 0.3770(3) 0.1071(2) -0.4100(4) 0.041 Uiso 1 calc R . 
C3A C 0.4617(3) 0.1043(2) -0.2028(4) 0.0344(10) Uani 1 d . . 
C4A C 0.5598(3) 0.1215(2) -0.1004(4) 0.0327(9) Uani 1 d . . 
H4A H 0.5740(3) 0.1137(2) -0.0060(4) 0.039 Uiso 1 calc R . 
C5A C 0.6361(3) 0.1504(2) -0.1416(4) 0.0329(9) Uani 1 d . . 
C11A C 0.5093(3) 0.1612(2) -0.5186(4) 0.0321(9) Uani 1 d . . 
C12A C 0.5894(3) 0.1912(2) -0.5510(4) 0.0405(10) Uani 1 d . . 
H12A H 0.6544(3) 0.2031(2) -0.4799(4) 0.049 Uiso 1 calc R . 
C13A C 0.5724(3) 0.2032(2) -0.6883(4) 0.0447(11) Uani 1 d . . 
H13A H 0.6262(3) 0.2230(2) -0.7118(4) 0.054 Uiso 1 calc R . 
C14A C 0.4771(3) 0.1863(2) -0.7893(4) 0.0499(12) Uani 1 d . . 
H14A H 0.4629(3) 0.1942(2) -0.8836(4) 0.060 Uiso 1 calc R . 
C15A C 0.4021(3) 0.1570(2) -0.7483(5) 0.0550(13) Uani 1 d . . 
H15A H 0.3362(3) 0.1453(2) -0.8182(5) 0.066 Uiso 1 calc R . 
C21A C 0.7416(3) 0.1719(2) -0.0375(4) 0.0330(10) Uani 1 d . . 
C22A C 0.8207(3) 0.1955(2) -0.0809(4) 0.0430(11) Uani 1 d . . 
H22A H 0.8103(3) 0.1964(2) -0.1760(4) 0.052 Uiso 1 calc R . 
C23A C 0.9152(3) 0.2175(2) 0.0168(5) 0.0527(12) Uani 1 d . . 
H23A H 0.9697(3) 0.2342(2) -0.0107(5) 0.063 Uiso 1 calc R . 
C24A C 0.9286(3) 0.2149(2) 0.1549(5) 0.0509(12) Uani 1 d . . 
H24A H 0.9916(3) 0.2302(2) 0.2238(5) 0.061 Uiso 1 calc R . 
C25A C 0.8475(3) 0.1892(2) 0.1898(4) 0.0494(12) Uani 1 d . . 
H25A H 0.8578(3) 0.1866(2) 0.2847(4) 0.059 Uiso 1 calc R . 
O1B O 0.4241(2) 0.04263(13) 0.0717(3) 0.0459(8) Uani 1 d . . 
N1B N 0.1779(2) -0.04296(13) 0.1378(3) 0.0328(8) Uani 1 d . . 
H1NB H 0.1262(2) -0.06249(13) 0.1522(3) 0.039 Uiso 1 calc R . 
N2B N 0.1808(3) -0.0785(2) 0.3819(3) 0.0427(9) Uani 1 d . . 
N3B N -0.0047(2) -0.07878(15) -0.0500(3) 0.0402(9) Uani 1 d . . 
C1B C 0.2678(3) -0.0273(2) 0.2494(4) 0.0306(9) Uani 1 d . . 
C2B C 0.3498(3) 0.0022(2) 0.2277(4) 0.0352(10) Uani 1 d . . 
H2B H 0.4115(3) 0.0135(2) 0.3047(4) 0.042 Uiso 1 calc R . 
C3B C 0.3449(3) 0.0164(2) 0.0915(4) 0.0352(10) Uani 1 d . . 
C4B C 0.2472(3) -0.0003(2) -0.0209(4) 0.0346(10) Uani 1 d . . 
H4B H 0.2390(3) 0.0088(2) -0.1130(4) 0.042 Uiso 1 calc R . 
C5B C 0.1659(3) -0.0294(2) 0.0049(4) 0.0310(9) Uani 1 d . . 
C11B C 0.2656(3) -0.0448(2) 0.3865(4) 0.0308(9) Uani 1 d . . 
C12B C 0.3450(3) -0.0273(2) 0.5102(4) 0.0397(11) Uani 1 d . . 
H12B H 0.4025(3) -0.0030(2) 0.5096(4) 0.048 Uiso 1 calc R . 
C13B C 0.3394(3) -0.0455(2) 0.6345(4) 0.0447(11) Uani 1 d . . 
H13B H 0.3932(3) -0.0343(2) 0.7196(4) 0.054 Uiso 1 calc R . 
C14B C 0.2534(3) -0.0805(2) 0.6317(4) 0.0472(11) Uani 1 d . . 
H14B H 0.2471(3) -0.0938(2) 0.7147(4) 0.057 Uiso 1 calc R . 
C15B C 0.1766(3) -0.0954(2) 0.5039(5) 0.0510(12) Uani 1 d . . 
H15B H 0.1176(3) -0.1190(2) 0.5025(5) 0.061 Uiso 1 calc R . 
C21B C 0.0609(3) -0.0496(2) -0.1012(4) 0.0326(9) Uani 1 d . . 
C22B C 0.0326(3) -0.0390(2) -0.2425(4) 0.0429(11) Uani 1 d . . 
H22B H 0.0794(3) -0.0178(2) -0.2757(4) 0.051 Uiso 1 calc R . 
C23B C -0.0667(3) -0.0607(2) -0.3339(5) 0.0511(12) Uani 1 d . . 
H23B H -0.0881(3) -0.0543(2) -0.4302(5) 0.061 Uiso 1 calc R . 
C24B C -0.1329(3) -0.0913(2) -0.2823(5) 0.0493(12) Uani 1 d . . 
H24B H -0.1999(3) -0.1068(2) -0.3422(5) 0.059 Uiso 1 calc R . 
C25B C -0.0991(3) -0.0989(2) -0.1406(5) 0.0477(12) Uani 1 d . . 
H25B H -0.1453(3) -0.1196(2) -0.1055(5) 0.057 Uiso 1 calc R . 
Cl1 Cl 0.1592(2) 0.18401(10) -0.4158(2) 0.1210(8) Uani 1 d . . 
Cl2 Cl 0.08076(13) 0.13641(8) -0.2169(2) 0.1169(7) Uani 1 d . . 
Cl3 Cl 0.23943(15) 0.22664(9) -0.1405(2) 0.1468(10) Uani 1 d . . 
C99 C 0.1929(4) 0.1665(2) -0.2433(5) 0.0565(13) Uani 1 d . . 
H99 H 0.2524(4) 0.1372(2) -0.2177(5) 0.068 Uiso 1 calc R . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1A 0.0298(14) 0.056(2) 0.045(2) 0.0103(15) 0.0133(13) -0.0034(14) 
N1A 0.029(2) 0.034(2) 0.032(2) -0.002(2) 0.010(2) -0.0025(14) 
N2A 0.040(2) 0.065(3) 0.032(2) 0.001(2) 0.007(2) -0.011(2) 
N3A 0.046(2) 0.043(2) 0.035(2) -0.003(2) 0.010(2) -0.008(2) 
C1A 0.028(2) 0.029(2) 0.037(2) -0.002(2) 0.008(2) 0.001(2) 
C2A 0.024(2) 0.037(2) 0.039(3) 0.002(2) 0.008(2) -0.001(2) 
C3A 0.027(2) 0.033(2) 0.046(3) 0.008(2) 0.017(2) 0.002(2) 
C4A 0.029(2) 0.036(2) 0.034(2) 0.005(2) 0.011(2) 0.002(2) 
C5A 0.031(2) 0.029(2) 0.038(3) -0.001(2) 0.012(2) 0.000(2) 
C11A 0.030(2) 0.034(2) 0.031(2) 0.000(2) 0.010(2) 0.000(2) 
C12A 0.037(2) 0.042(3) 0.039(3) -0.001(2) 0.010(2) -0.008(2) 
C13A 0.048(3) 0.046(3) 0.042(3) 0.003(2) 0.019(2) -0.011(2) 
C14A 0.054(3) 0.060(3) 0.034(3) -0.002(2) 0.014(2) -0.005(2) 
C15A 0.040(3) 0.080(4) 0.039(3) -0.004(3) 0.008(2) -0.018(2) 
C21A 0.030(2) 0.028(2) 0.038(3) 0.001(2) 0.008(2) 0.000(2) 
C22A 0.034(2) 0.053(3) 0.038(3) 0.005(2) 0.007(2) -0.009(2) 
C23A 0.040(3) 0.059(3) 0.053(3) 0.009(3) 0.010(2) -0.011(2) 
C24A 0.042(3) 0.047(3) 0.052(3) -0.004(2) 0.003(2) -0.015(2) 
C25A 0.057(3) 0.048(3) 0.034(3) -0.004(2) 0.006(2) -0.013(2) 
O1B 0.0312(15) 0.062(2) 0.044(2) 0.0079(15) 0.0135(13) -0.0127(14) 
N1B 0.026(2) 0.035(2) 0.036(2) 0.001(2) 0.009(2) -0.0037(14) 
N2B 0.035(2) 0.055(2) 0.038(2) 0.004(2) 0.014(2) -0.011(2) 
N3B 0.026(2) 0.044(2) 0.045(2) 0.000(2) 0.007(2) -0.007(2) 
C1B 0.024(2) 0.030(2) 0.036(2) 0.000(2) 0.008(2) 0.002(2) 
C2B 0.025(2) 0.042(2) 0.034(2) -0.001(2) 0.006(2) -0.002(2) 
C3B 0.029(2) 0.041(2) 0.035(2) 0.002(2) 0.012(2) 0.001(2) 
C4B 0.032(2) 0.040(2) 0.032(2) 0.004(2) 0.011(2) 0.002(2) 
C5B 0.027(2) 0.035(2) 0.029(2) 0.003(2) 0.008(2) 0.004(2) 
C11B 0.027(2) 0.033(2) 0.034(2) 0.002(2) 0.013(2) 0.002(2) 
C12B 0.031(2) 0.050(3) 0.037(3) -0.002(2) 0.012(2) -0.008(2) 
C13B 0.042(2) 0.055(3) 0.037(3) -0.003(2) 0.014(2) -0.002(2) 
C14B 0.049(3) 0.057(3) 0.037(3) 0.008(2) 0.018(2) 0.003(2) 
C15B 0.042(3) 0.065(3) 0.048(3) 0.007(3) 0.019(2) -0.014(2) 
C21B 0.030(2) 0.032(2) 0.032(2) -0.002(2) 0.008(2) 0.004(2) 
C22B 0.036(2) 0.052(3) 0.037(3) 0.002(2) 0.010(2) 0.000(2) 
C23B 0.042(3) 0.062(3) 0.036(3) -0.004(2) -0.001(2) 0.005(2) 
C24B 0.032(2) 0.051(3) 0.051(3) -0.010(2) -0.001(2) 0.000(2) 
C25B 0.032(2) 0.050(3) 0.059(3) -0.003(2) 0.013(2) -0.005(2) 
Cl1 0.1290(15) 0.175(2) 0.0730(11) 0.0404(12) 0.0539(10) 0.0845(14) 
Cl2 0.0732(10) 0.1098(14) 0.181(2) 0.0661(13) 0.0618(12) 0.0162(9) 
Cl3 0.0901(12) 0.127(2) 0.169(2) -0.0820(15) -0.0174(12) 0.0085(11) 
C99 0.051(3) 0.057(3) 0.060(3) 0.000(3) 0.018(2) 0.010(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 
O1A C3A 1.351(4) . ? 
N1A C5A 1.342(5) . ? 
N1A C1A 1.349(4) . ? 
N2A C11A 1.335(5) . ? 
N2A C15A 1.337(5) . ? 
N3A C25A 1.337(5) . ? 
N3A C21A 1.340(5) . ? 
C1A C2A 1.393(5) . ? 
C1A C11A 1.482(5) . ? 
C2A C3A 1.376(5) . ? 
C3A C4A 1.391(5) . ? 
C4A C5A 1.389(5) . ? 
C5A C21A 1.492(5) . ? 
C11A C12A 1.393(5) . ? 
C12A C13A 1.379(6) . ? 
C13A C14A 1.360(5) . ? 
C14A C15A 1.378(6) . ? 
C21A C22A 1.380(5) . ? 
C22A C23A 1.377(5) . ? 
C23A C24A 1.372(6) . ? 
C24A C25A 1.372(6) . ? 
O1B C3B 1.279(4) . ? 
N1B C5B 1.357(5) . ? 
N1B C1B 1.362(4) . ? 
N2B C15B 1.337(5) . ? 
N2B C11B 1.341(5) . ? 
N3B C25B 1.333(5) . ? 
N3B C21B 1.341(5) . ? 
C1B C2B 1.356(5) . ? 
C1B C11B 1.480(5) . ? 
C2B C3B 1.420(5) . ? 
C3B C4B 1.432(5) . ? 
C4B C5B 1.363(5) . ? 
C5B C21B 1.486(5) . ? 
C11B C12B 1.381(5) . ? 
C12B C13B 1.375(6) . ? 
C13B C14B 1.375(6) . ? 
C14B C15B 1.380(6) . ? 
C21B C22B 1.388(5) . ? 
C22B C23B 1.392(5) . ? 
C23B C24B 1.366(6) . ? 
C24B C25B 1.376(6) . ? 
Cl1 C99 1.718(5) . ? 
Cl2 C99 1.732(5) . ? 
Cl3 C99 1.714(5) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C5A N1A C1A 117.7(3) . . ? 
C11A N2A C15A 116.7(4) . . ? 
C25A N3A C21A 117.0(4) . . ? 
N1A C1A C2A 122.0(4) . . ? 
N1A C1A C11A 116.1(3) . . ? 
C2A C1A C11A 121.9(3) . . ? 
C3A C2A C1A 119.7(4) . . ? 
O1A C3A C2A 118.0(3) . . ? 
O1A C3A C4A 123.1(4) . . ? 
C2A C3A C4A 118.9(3) . . ? 
C5A C4A C3A 118.2(4) . . ? 
N1A C5A C4A 123.5(3) . . ? 
N1A C5A C21A 115.1(3) . . ? 
C4A C5A C21A 121.3(4) . . ? 
N2A C11A C12A 121.9(4) . . ? 
N2A C11A C1A 116.4(3) . . ? 
C12A C11A C1A 121.6(3) . . ? 
C13A C12A C11A 119.5(4) . . ? 
C14A C13A C12A 119.2(4) . . ? 
C13A C14A C15A 117.6(4) . . ? 
N2A C15A C14A 125.0(4) . . ? 
N3A C21A C22A 122.4(4) . . ? 
N3A C21A C5A 117.2(3) . . ? 
C22A C21A C5A 120.3(4) . . ? 
C23A C22A C21A 119.2(4) . . ? 
C24A C23A C22A 119.0(4) . . ? 
C25A C24A C23A 118.2(4) . . ? 
N3A C25A C24A 124.1(4) . . ? 
C5B N1B C1B 122.7(3) . . ? 
C15B N2B C11B 116.9(3) . . ? 
C25B N3B C21B 117.5(4) . . ? 
C2B C1B N1B 119.1(4) . . ? 
C2B C1B C11B 125.8(3) . . ? 
N1B C1B C11B 115.1(3) . . ? 
C1B C2B C3B 121.6(4) . . ? 
O1B C3B C2B 121.2(3) . . ? 
O1B C3B C4B 122.3(4) . . ? 
C2B C3B C4B 116.4(4) . . ? 
C5B C4B C3B 120.3(4) . . ? 
N1B C5B C4B 119.9(3) . . ? 
N1B C5B C21B 114.1(3) . . ? 
C4B C5B C21B 126.0(4) . . ? 
N2B C11B C12B 122.4(4) . . ? 
N2B C11B C1B 115.3(3) . . ? 
C12B C11B C1B 122.3(3) . . ? 
C13B C12B C11B 119.7(4) . . ? 
C14B C13B C12B 118.6(4) . . ? 
C13B C14B C15B 118.2(4) . . ? 
N2B C15B C14B 124.1(4) . . ? 
N3B C21B C22B 122.4(4) . . ? 
N3B C21B C5B 114.8(3) . . ? 
C22B C21B C5B 122.8(4) . . ? 
C21B C22B C23B 118.4(4) . . ? 
C24B C23B C22B 119.4(4) . . ? 
C23B C24B C25B 118.3(4) . . ? 
N3B C25B C24B 124.0(4) . . ? 
Cl3 C99 Cl1 110.5(3) . . ? 
Cl3 C99 Cl2 110.9(3) . . ? 
Cl1 C99 Cl2 110.1(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 
 C5A N1A C1A C2A -0.9(5) . . . . ? 
 C5A N1A C1A C11A 178.9(3) . . . . ? 
 N1A C1A C2A C3A -0.6(6) . . . . ? 
 C11A C1A C2A C3A 179.6(4) . . . . ? 
 C1A C2A C3A O1A -179.5(3) . . . . ? 
 C1A C2A C3A C4A 1.6(6) . . . . ? 
 O1A C3A C4A C5A -180.0(3) . . . . ? 
 C2A C3A C4A C5A -1.1(6) . . . . ? 
 C1A N1A C5A C4A 1.4(5) . . . . ? 
 C1A N1A C5A C21A -177.0(3) . . . . ? 
 C3A C4A C5A N1A -0.4(6) . . . . ? 
 C3A C4A C5A C21A 177.9(3) . . . . ? 
 C15A N2A C11A C12A -0.2(6) . . . . ? 
 C15A N2A C11A C1A -179.6(4) . . . . ? 
 N1A C1A C11A N2A 178.1(3) . . . . ? 
 C2A C1A C11A N2A -2.1(5) . . . . ? 
 N1A C1A C11A C12A -1.3(5) . . . . ? 
 C2A C1A C11A C12A 178.5(4) . . . . ? 
 N2A C11A C12A C13A -0.5(6) . . . . ? 
 C1A C11A C12A C13A 178.9(4) . . . . ? 
 C11A C12A C13A C14A 0.9(6) . . . . ? 
 C12A C13A C14A C15A -0.7(7) . . . . ? 
 C11A N2A C15A C14A 0.4(7) . . . . ? 
 C13A C14A C15A N2A 0.0(8) . . . . ? 
 C25A N3A C21A C22A 2.1(6) . . . . ? 
 C25A N3A C21A C5A -177.4(3) . . . . ? 
 N1A C5A C21A N3A 171.6(3) . . . . ? 
 C4A C5A C21A N3A -6.9(5) . . . . ? 
 N1A C5A C21A C22A -7.9(5) . . . . ? 
 C4A C5A C21A C22A 173.6(4) . . . . ? 
 N3A C21A C22A C23A -2.5(6) . . . . ? 
 C5A C21A C22A C23A 176.9(4) . . . . ? 
 C21A C22A C23A C24A 0.8(7) . . . . ? 
 C22A C23A C24A C25A 1.1(7) . . . . ? 
 C21A N3A C25A C24A 0.0(7) . . . . ? 
 C23A C24A C25A N3A -1.6(7) . . . . ? 
 C5B N1B C1B C2B -1.2(5) . . . . ? 
 C5B N1B C1B C11B 178.7(3) . . . . ? 
 N1B C1B C2B C3B -0.9(6) . . . . ? 
 C11B C1B C2B C3B 179.2(4) . . . . ? 
 C1B C2B C3B O1B -177.8(4) . . . . ? 
 C1B C2B C3B C4B 2.1(6) . . . . ? 
 O1B C3B C4B C5B 178.5(4) . . . . ? 
 C2B C3B C4B C5B -1.4(6) . . . . ? 
 C1B N1B C5B C4B 1.9(5) . . . . ? 
 C1B N1B C5B C21B -178.9(3) . . . . ? 
 C3B C4B C5B N1B -0.5(6) . . . . ? 
 C3B C4B C5B C21B -179.6(4) . . . . ? 
 C15B N2B C11B C12B -0.9(6) . . . . ? 
 C15B N2B C11B C1B 179.6(4) . . . . ? 
 C2B C1B C11B N2B -173.9(4) . . . . ? 
 N1B C1B C11B N2B 6.2(5) . . . . ? 
 C2B C1B C11B C12B 6.6(6) . . . . ? 
 N1B C1B C11B C12B -173.3(4) . . . . ? 
 N2B C11B C12B C13B 1.3(6) . . . . ? 
 C1B C11B C12B C13B -179.2(4) . . . . ? 
 C11B C12B C13B C14B -0.7(6) . . . . ? 
 C12B C13B C14B C15B -0.1(6) . . . . ? 
 C11B N2B C15B C14B -0.1(7) . . . . ? 
 C13B C14B C15B N2B 0.6(7) . . . . ? 
 C25B N3B C21B C22B 1.3(6) . . . . ? 
 C25B N3B C21B C5B -178.8(3) . . . . ? 
 N1B C5B C21B N3B -1.0(5) . . . . ? 
 C4B C5B C21B N3B 178.1(4) . . . . ? 
 N1B C5B C21B C22B 178.9(4) . . . . ? 
 C4B C5B C21B C22B -2.0(6) . . . . ? 
 N3B C21B C22B C23B -1.2(6) . . . . ? 
 C5B C21B C22B C23B 178.9(4) . . . . ? 
 C21B C22B C23B C24B 0.1(6) . . . . ? 
 C22B C23B C24B C25B 0.9(7) . . . . ? 
 C21B N3B C25B C24B -0.3(6) . . . . ? 
 C23B C24B C25B N3B -0.8(7) . . . . ? 
  
_refine_diff_density_max     .405 
_refine_diff_density_min    -.469 
_refine_diff_density_rms     .053