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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Steven Nolan'
_publ_contact_author_address     
;
Department of Chemistry
University of New Orleans
New Orleans
LA 70148
UNITED STATES OF AMERICA
;

_publ_contact_author_email       SNOLAN@UNO.EDU

_publ_section_title              
;
reactivity of a N-heterocyclic carbene, 1,3 di-9 1
adamantyl) imidazol-2-ylidene, with a Pseudo-Acid: Structural
Characterization of a Claisen Condensation adduct.
;
loop_
_publ_author_name
'Steven Nolan'
'Gabriela A. Grasa'
'Rohit Singh'
'Edwin D. Stevens'

data_nol101m
_database_code_depnum_ccdc_archive 'CCDC 244497'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '[C23 H33 N2]+ [C5 H7 O3]-'
_chemical_formula_weight         452.62

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.5366(13)
_cell_length_b                   11.6995(12)
_cell_length_c                   15.7153(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.217(2)
_cell_angle_gamma                90.00
_cell_volume                     2484.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19716
_cell_measurement_theta_min      2.171
_cell_measurement_theta_max      31.042

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.55
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.078
_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      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19166
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         22.50
_reflns_number_total             3247
_reflns_number_gt                2964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections.  The weighted R-factor wR and
goodness 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 threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.8102P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     458
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.101
_refine_ls_shift/su_mean         0.016

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
N1 N 0.45835(9) 0.98690(10) 0.24765(7) 0.0243(3) Uani 1 1 d U . .
C2 C 0.49952(11) 1.07823(13) 0.21330(10) 0.0261(4) Uani 1 1 d U . .
H2 H 0.4937(11) 1.0972(13) 0.1555(10) 0.021(4) Uiso 1 1 d . . .
N3 N 0.54151(9) 1.14317(10) 0.27539(7) 0.0245(3) Uani 1 1 d U . .
C4 C 0.52430(12) 1.09171(13) 0.35264(10) 0.0270(4) Uani 1 1 d U . .
H4 H 0.5468(12) 1.1217(14) 0.4052(11) 0.030(4) Uiso 1 1 d . . .
C5 C 0.47274(12) 0.99500(13) 0.33534(10) 0.0269(4) Uani 1 1 d U . .
H5 H 0.4493(11) 0.9382(14) 0.3728(10) 0.027(4) Uiso 1 1 d . . .
C6 C 0.40506(11) 0.89306(12) 0.19893(9) 0.0228(4) Uani 1 1 d U . .
C7 C 0.29296(12) 0.90847(15) 0.20423(11) 0.0315(4) Uani 1 1 d U . .
H7A H 0.2749(12) 0.9832(16) 0.1812(11) 0.035(5) Uiso 1 1 d . . .
H7B H 0.2770(13) 0.9061(15) 0.2637(12) 0.040(5) Uiso 1 1 d . . .
C8 C 0.23932(13) 0.81222(15) 0.15396(11) 0.0355(4) Uani 1 1 d U . .
H8 H 0.1688(15) 0.8255(16) 0.1557(12) 0.049(5) Uiso 1 1 d . . .
C9 C 0.27029(14) 0.69684(16) 0.19274(12) 0.0409(5) Uani 1 1 d U . .
H9A H 0.2497(14) 0.6928(16) 0.2514(13) 0.046(5) Uiso 1 1 d . . .
H9B H 0.2348(14) 0.6350(16) 0.1605(11) 0.042(5) Uiso 1 1 d . . .
C10 C 0.38219(14) 0.68129(14) 0.18731(11) 0.0361(4) Uani 1 1 d U . .
H10 H 0.4036(14) 0.6069(18) 0.2115(12) 0.051(5) Uiso 1 1 d . . .
C11 C 0.43670(14) 0.77768(14) 0.23744(11) 0.0328(4) Uani 1 1 d U . .
H11A H 0.4189(12) 0.7748(14) 0.2953(12) 0.033(4) Uiso 1 1 d . . .
H11B H 0.5086(15) 0.7682(15) 0.2348(11) 0.042(5) Uiso 1 1 d . . .
C12 C 0.43141(12) 0.89776(14) 0.10565(10) 0.0260(4) Uani 1 1 d U . .
H12A H 0.4104(12) 0.9720(16) 0.0807(10) 0.032(4) Uiso 1 1 d . . .
H12B H 0.5031(14) 0.8890(14) 0.1021(10) 0.032(4) Uiso 1 1 d . . .
C13 C 0.37769(12) 0.80047(13) 0.05651(10) 0.0275(4) Uani 1 1 d U . .
H13 H 0.3952(12) 0.8041(14) -0.0036(11) 0.030(4) Uiso 1 1 d . . .
C14 C 0.40917(14) 0.68570(14) 0.09493(11) 0.0343(4) Uani 1 1 d U . .
H14A H 0.3752(13) 0.6244(16) 0.0633(11) 0.038(5) Uiso 1 1 d . . .
H14B H 0.4825(15) 0.6781(15) 0.0906(11) 0.042(5) Uiso 1 1 d . . .
C15 C 0.26642(12) 0.81573(15) 0.06092(11) 0.0321(4) Uani 1 1 d U . .
H15A H 0.2301(13) 0.7534(16) 0.0289(11) 0.038(5) Uiso 1 1 d . . .
H15B H 0.2460(12) 0.8875(16) 0.0349(10) 0.035(5) Uiso 1 1 d . . .
C16 C 0.59673(11) 1.25244(12) 0.26332(9) 0.0220(3) Uani 1 1 d U . .
C17 C 0.53287(12) 1.35284(13) 0.28949(10) 0.0273(4) Uani 1 1 d U . .
H17A H 0.5173(11) 1.3443(13) 0.3524(10) 0.026(4) Uiso 1 1 d . . .
H17B H 0.4692(13) 1.3519(14) 0.2512(10) 0.032(4) Uiso 1 1 d . . .
C18 C 0.59010(12) 1.46496(14) 0.27727(10) 0.0312(4) Uani 1 1 d U . .
H18 H 0.5481(13) 1.5267(15) 0.2942(10) 0.036(4) Uiso 1 1 d . . .
C19 C 0.68581(13) 1.46142(15) 0.33346(11) 0.0334(4) Uani 1 1 d U . .
H19A H 0.6722(11) 1.4553(14) 0.3935(11) 0.030(4) Uiso 1 1 d . . .
H19B H 0.7236(13) 1.5368(17) 0.3271(11) 0.043(5) Uiso 1 1 d . . .
C20 C 0.75041(12) 1.36217(14) 0.30716(11) 0.0327(4) Uani 1 1 d U . .
H20 H 0.8092(13) 1.3587(14) 0.3429(11) 0.034(4) Uiso 1 1 d . . .
C21 C 0.69367(12) 1.24955(14) 0.31912(11) 0.0288(4) Uani 1 1 d U . .
H21A H 0.6788(11) 1.2418(14) 0.3821(11) 0.031(4) Uiso 1 1 d . . .
H21B H 0.7354(13) 1.1814(16) 0.2996(11) 0.040(5) Uiso 1 1 d . . .
C22 C 0.62033(12) 1.26464(14) 0.16965(10) 0.0270(4) Uani 1 1 d U . .
H22A H 0.5561(12) 1.2644(13) 0.1328(10) 0.024(4) Uiso 1 1 d . . .
H22B H 0.6612(12) 1.1981(14) 0.1529(10) 0.030(4) Uiso 1 1 d . . .
C23 C 0.67770(12) 1.37708(14) 0.15788(11) 0.0317(4) Uani 1 1 d U . .
H23 H 0.6927(12) 1.3834(14) 0.0976(12) 0.038(5) Uiso 1 1 d . . .
C24 C 0.77374(13) 1.37445(18) 0.21360(12) 0.0392(4) Uani 1 1 d U . .
H24A H 0.8141(13) 1.3090(16) 0.1959(11) 0.038(5) Uiso 1 1 d . . .
H24B H 0.8118(14) 1.4487(18) 0.2060(12) 0.052(5) Uiso 1 1 d . . .
C25 C 0.61245(13) 1.47611(14) 0.18371(11) 0.0342(4) Uani 1 1 d U . .
H25A H 0.6462(14) 1.5514(18) 0.1737(11) 0.049(5) Uiso 1 1 d . . .
H25B H 0.5483(13) 1.4759(14) 0.1483(11) 0.035(4) Uiso 1 1 d . . .
C26 C 0.32543(16) 0.37045(16) 0.04180(14) 0.0407(5) Uani 1 1 d U . .
H26A H 0.277(2) 0.396(3) 0.001(2) 0.116(11) Uiso 1 1 d . . .
H26B H 0.385(2) 0.401(2) 0.0278(17) 0.096(9) Uiso 1 1 d . . .
H26C H 0.303(2) 0.406(3) 0.091(2) 0.103(10) Uiso 1 1 d . . .
C27 C 0.32912(11) 0.24142(13) 0.04881(9) 0.0270(4) Uani 1 1 d U . .
O28 O 0.41402(8) 0.19626(10) 0.05308(8) 0.0404(3) Uani 1 1 d U . .
C29 C 0.24222(11) 0.17672(14) 0.05018(9) 0.0259(4) Uani 1 1 d U . .
H29 H 0.2506(12) 0.0958(17) 0.0545(10) 0.035(5) Uiso 1 1 d . . .
C30 C 0.14397(11) 0.21657(13) 0.04369(9) 0.0244(4) Uani 1 1 d U . .
O31 O 0.11144(8) 0.31532(9) 0.03555(7) 0.0304(3) Uani 1 1 d U . .
O32 O 0.07698(8) 0.12695(9) 0.04600(8) 0.0385(3) Uani 1 1 d U . .
C33 C -0.02546(13) 0.15712(19) 0.03715(13) 0.0404(5) Uani 1 1 d U . .
H33A H -0.0467(15) 0.1935(17) 0.0883(14) 0.054(6) Uiso 1 1 d . . .
H33B H -0.0407(15) 0.2088(18) -0.0120(14) 0.056(6) Uiso 1 1 d . . .
H33C H -0.0647(17) 0.087(2) 0.0265(14) 0.069(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0327(7) 0.0192(7) 0.0208(7) -0.0010(5) 0.0003(5) -0.0057(6)
C2 0.0350(9) 0.0231(9) 0.0199(9) 0.0011(7) -0.0014(7) -0.0059(7)
N3 0.0328(7) 0.0195(7) 0.0209(7) -0.0013(5) 0.0004(5) -0.0054(6)
C4 0.0364(9) 0.0252(9) 0.0194(8) -0.0022(7) 0.0016(7) -0.0052(7)
C5 0.0374(9) 0.0229(9) 0.0206(8) 0.0004(7) 0.0023(7) -0.0052(7)
C6 0.0279(8) 0.0173(8) 0.0228(8) -0.0024(6) -0.0021(6) -0.0049(6)
C7 0.0327(9) 0.0299(10) 0.0325(10) -0.0066(8) 0.0075(7) -0.0009(8)
C8 0.0221(9) 0.0405(10) 0.0440(10) -0.0115(8) 0.0039(7) -0.0037(7)
C9 0.0528(12) 0.0366(11) 0.0335(10) -0.0033(8) 0.0051(9) -0.0227(9)
C10 0.0491(11) 0.0173(9) 0.0403(10) 0.0028(7) -0.0124(8) -0.0036(8)
C11 0.0427(11) 0.0233(9) 0.0314(10) 0.0018(7) -0.0084(8) -0.0040(8)
C12 0.0274(10) 0.0253(9) 0.0256(8) -0.0027(7) 0.0029(7) -0.0034(7)
C13 0.0323(9) 0.0270(9) 0.0234(9) -0.0060(7) 0.0024(7) -0.0040(7)
C14 0.0340(10) 0.0240(9) 0.0440(10) -0.0122(8) -0.0050(8) 0.0012(8)
C15 0.0332(9) 0.0265(10) 0.0352(9) -0.0034(8) -0.0093(7) -0.0010(8)
C16 0.0251(8) 0.0172(8) 0.0237(8) -0.0005(6) 0.0012(6) -0.0049(6)
C17 0.0256(9) 0.0271(9) 0.0293(9) -0.0022(7) 0.0017(7) -0.0009(7)
C18 0.0354(9) 0.0212(9) 0.0368(9) -0.0032(7) -0.0011(7) 0.0042(7)
C19 0.0409(10) 0.0252(9) 0.0335(10) -0.0016(7) -0.0029(8) -0.0084(8)
C20 0.0241(9) 0.0370(10) 0.0359(9) 0.0006(8) -0.0076(7) -0.0059(7)
C21 0.0301(9) 0.0263(9) 0.0297(9) -0.0007(7) -0.0007(7) 0.0017(7)
C22 0.0288(9) 0.0261(9) 0.0262(9) -0.0012(7) 0.0024(7) -0.0003(7)
C23 0.0324(9) 0.0368(10) 0.0262(9) 0.0022(7) 0.0044(7) -0.0076(7)
C24 0.0302(10) 0.0437(11) 0.0440(11) 0.0023(9) 0.0059(8) -0.0046(9)
C25 0.0387(10) 0.0248(9) 0.0382(10) 0.0068(7) -0.0066(8) -0.0071(8)
C26 0.0385(11) 0.0304(10) 0.0536(13) 0.0019(9) 0.0052(10) -0.0078(8)
C27 0.0297(9) 0.0291(9) 0.0219(8) 0.0018(7) -0.0020(6) 0.0031(7)
O28 0.0271(7) 0.0446(8) 0.0488(7) 0.0075(6) -0.0035(5) 0.0037(6)
C29 0.0298(9) 0.0196(9) 0.0278(9) 0.0019(7) -0.0022(7) 0.0016(7)
C30 0.0320(9) 0.0227(9) 0.0186(8) 0.0005(6) 0.0013(6) -0.0020(7)
O31 0.0338(6) 0.0257(6) 0.0319(6) 0.0008(5) 0.0037(5) 0.0072(5)
O32 0.0290(7) 0.0313(7) 0.0549(8) 0.0038(5) -0.0005(5) -0.0046(5)
C33 0.0271(10) 0.0529(12) 0.0411(11) 0.0019(10) 0.0018(8) -0.0040(9)

_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
N1 C2 1.333(2) . ?
N1 C5 1.384(2) . ?
N1 C6 1.4999(18) . ?
C2 N3 1.3380(19) . ?
C2 H2 0.933(16) . ?
N3 C4 1.386(2) . ?
N3 C16 1.4984(19) . ?
C4 C5 1.349(2) . ?
C4 H4 0.932(17) . ?
C5 H5 0.953(17) . ?
C6 C12 1.529(2) . ?
C6 C11 1.531(2) . ?
C6 C7 1.535(2) . ?
C7 C8 1.535(2) . ?
C7 H7A 0.973(19) . ?
C7 H7B 0.972(18) . ?
C8 C15 1.528(2) . ?
C8 C9 1.530(3) . ?
C8 H8 0.97(2) . ?
C9 C10 1.533(3) . ?
C9 H9A 0.98(2) . ?
C9 H9B 0.99(2) . ?
C10 C14 1.518(3) . ?
C10 C11 1.540(2) . ?
C10 H10 0.99(2) . ?
C11 H11A 0.955(18) . ?
C11 H11B 0.983(19) . ?
C12 C13 1.536(2) . ?
C12 H12A 0.988(18) . ?
C12 H12B 0.981(18) . ?
C13 C14 1.523(2) . ?
C13 C15 1.522(2) . ?
C13 H13 0.988(17) . ?
C14 H14A 0.973(19) . ?
C14 H14B 1.002(19) . ?
C15 H15A 1.000(19) . ?
C15 H15B 0.967(19) . ?
C16 C17 1.528(2) . ?
C16 C22 1.531(2) . ?
C16 C21 1.537(2) . ?
C17 C18 1.541(2) . ?
C17 H17A 1.027(16) . ?
C17 H17B 1.023(17) . ?
C18 C25 1.523(2) . ?
C18 C19 1.527(2) . ?
C18 H18 0.966(18) . ?
C19 C20 1.525(2) . ?
C19 H19A 0.975(17) . ?
C19 H19B 1.03(2) . ?
C20 C24 1.528(2) . ?
C20 C21 1.542(2) . ?
C20 H20 0.949(18) . ?
C21 H21A 1.026(17) . ?
C21 H21B 1.033(19) . ?
C22 C23 1.544(2) . ?
C22 H22A 1.017(16) . ?
C22 H22B 1.000(17) . ?
C23 C25 1.526(2) . ?
C23 C24 1.526(2) . ?
C23 H23 0.983(18) . ?
C24 H24A 0.990(19) . ?
C24 H24B 1.02(2) . ?
C25 H25A 1.01(2) . ?
C25 H25B 1.005(18) . ?
C26 C27 1.514(3) . ?
C26 H26A 0.95(3) . ?
C26 H26B 0.92(3) . ?
C26 H26C 0.95(3) . ?
C27 O28 1.2633(19) . ?
C27 C29 1.400(2) . ?
C29 C30 1.408(2) . ?
C29 H29 0.956(19) . ?
C30 O31 1.2404(18) . ?
C30 O32 1.3881(19) . ?
O32 C33 1.430(2) . ?
C33 H33A 0.97(2) . ?
C33 H33B 0.99(2) . ?
C33 H33C 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.03(12) . . ?
C2 N1 C6 125.45(12) . . ?
C5 N1 C6 126.52(12) . . ?
N1 C2 N3 109.26(13) . . ?
N1 C2 H2 124.7(9) . . ?
N3 C2 H2 125.7(9) . . ?
C2 N3 C4 107.86(13) . . ?
C2 N3 C16 125.93(12) . . ?
C4 N3 C16 126.21(12) . . ?
C5 C4 N3 107.35(14) . . ?
C5 C4 H4 129.3(10) . . ?
N3 C4 H4 123.3(10) . . ?
C4 C5 N1 107.48(14) . . ?
C4 C5 H5 130.3(9) . . ?
N1 C5 H5 122.2(9) . . ?
N1 C6 C12 109.37(12) . . ?
N1 C6 C11 109.14(12) . . ?
C12 C6 C11 109.61(13) . . ?
N1 C6 C7 109.57(12) . . ?
C12 C6 C7 109.41(13) . . ?
C11 C6 C7 109.73(14) . . ?
C6 C7 C8 109.06(13) . . ?
C6 C7 H7A 108.3(10) . . ?
C8 C7 H7A 111.5(10) . . ?
C6 C7 H7B 108.8(10) . . ?
C8 C7 H7B 110.5(10) . . ?
H7A C7 H7B 108.6(14) . . ?
C15 C8 C9 109.26(14) . . ?
C15 C8 C7 109.93(14) . . ?
C9 C8 C7 109.34(14) . . ?
C15 C8 H8 108.2(11) . . ?
C9 C8 H8 112.3(11) . . ?
C7 C8 H8 107.8(11) . . ?
C8 C9 C10 109.40(14) . . ?
C8 C9 H9A 109.4(11) . . ?
C10 C9 H9A 112.4(11) . . ?
C8 C9 H9B 109.0(10) . . ?
C10 C9 H9B 109.7(10) . . ?
H9A C9 H9B 106.9(15) . . ?
C14 C10 C9 109.93(14) . . ?
C14 C10 C11 109.29(15) . . ?
C9 C10 C11 109.34(15) . . ?
C14 C10 H10 108.5(11) . . ?
C9 C10 H10 110.6(11) . . ?
C11 C10 H10 109.1(11) . . ?
C6 C11 C10 109.16(13) . . ?
C6 C11 H11A 109.1(10) . . ?
C10 C11 H11A 108.8(10) . . ?
C6 C11 H11B 109.8(11) . . ?
C10 C11 H11B 110.0(11) . . ?
H11A C11 H11B 109.9(15) . . ?
C6 C12 C13 109.03(13) . . ?
C6 C12 H12A 109.6(9) . . ?
C13 C12 H12A 109.5(9) . . ?
C6 C12 H12B 109.6(9) . . ?
C13 C12 H12B 109.7(10) . . ?
H12A C12 H12B 109.4(14) . . ?
C14 C13 C15 109.94(14) . . ?
C14 C13 C12 109.88(13) . . ?
C15 C13 C12 109.39(13) . . ?
C14 C13 H13 109.9(9) . . ?
C15 C13 H13 109.3(9) . . ?
C12 C13 H13 108.5(9) . . ?
C10 C14 C13 109.40(13) . . ?
C10 C14 H14A 109.3(10) . . ?
C13 C14 H14A 109.5(10) . . ?
C10 C14 H14B 110.8(10) . . ?
C13 C14 H14B 107.9(10) . . ?
H14A C14 H14B 109.9(15) . . ?
C13 C15 C8 109.37(13) . . ?
C13 C15 H15A 110.6(10) . . ?
C8 C15 H15A 109.0(10) . . ?
C13 C15 H15B 110.0(10) . . ?
C8 C15 H15B 110.4(10) . . ?
H15A C15 H15B 107.5(14) . . ?
N3 C16 C17 109.15(12) . . ?
N3 C16 C22 109.50(11) . . ?
C17 C16 C22 109.81(12) . . ?
N3 C16 C21 108.97(12) . . ?
C17 C16 C21 109.95(12) . . ?
C22 C16 C21 109.46(13) . . ?
C16 C17 C18 108.96(13) . . ?
C16 C17 H17A 109.5(9) . . ?
C18 C17 H17A 109.5(9) . . ?
C16 C17 H17B 107.7(9) . . ?
C18 C17 H17B 110.4(9) . . ?
H17A C17 H17B 110.7(12) . . ?
C25 C18 C19 110.64(14) . . ?
C25 C18 C17 108.76(13) . . ?
C19 C18 C17 108.72(13) . . ?
C25 C18 H18 110.7(10) . . ?
C19 C18 H18 110.7(10) . . ?
C17 C18 H18 107.1(10) . . ?
C20 C19 C18 110.17(14) . . ?
C20 C19 H19A 110.4(10) . . ?
C18 C19 H19A 111.2(9) . . ?
C20 C19 H19B 109.3(10) . . ?
C18 C19 H19B 109.4(10) . . ?
H19A C19 H19B 106.2(13) . . ?
C19 C20 C24 109.99(15) . . ?
C19 C20 C21 108.70(14) . . ?
C24 C20 C21 109.20(14) . . ?
C19 C20 H20 110.3(10) . . ?
C24 C20 H20 111.2(10) . . ?
C21 C20 H20 107.3(10) . . ?
C16 C21 C20 109.08(13) . . ?
C16 C21 H21A 110.2(9) . . ?
C20 C21 H21A 108.6(9) . . ?
C16 C21 H21B 108.1(10) . . ?
C20 C21 H21B 109.8(10) . . ?
H21A C21 H21B 111.0(13) . . ?
C16 C22 C23 109.16(13) . . ?
C16 C22 H22A 109.2(8) . . ?
C23 C22 H22A 110.7(9) . . ?
C16 C22 H22B 109.3(9) . . ?
C23 C22 H22B 110.0(9) . . ?
H22A C22 H22B 108.5(13) . . ?
C25 C23 C24 110.47(15) . . ?
C25 C23 C22 108.21(13) . . ?
C24 C23 C22 109.39(14) . . ?
C25 C23 H23 110.7(10) . . ?
C24 C23 H23 109.8(10) . . ?
C22 C23 H23 108.2(10) . . ?
C20 C24 C23 109.79(14) . . ?
C20 C24 H24A 110.1(10) . . ?
C23 C24 H24A 108.7(10) . . ?
C20 C24 H24B 109.0(11) . . ?
C23 C24 H24B 109.6(11) . . ?
H24A C24 H24B 109.6(15) . . ?
C18 C25 C23 109.95(13) . . ?
C18 C25 H25A 110.0(10) . . ?
C23 C25 H25A 110.4(11) . . ?
C18 C25 H25B 108.7(9) . . ?
C23 C25 H25B 110.3(10) . . ?
H25A C25 H25B 107.5(14) . . ?
C27 C26 H26A 112.9(19) . . ?
C27 C26 H26B 111.9(18) . . ?
H26A C26 H26B 107(2) . . ?
C27 C26 H26C 113.0(18) . . ?
H26A C26 H26C 100(2) . . ?
H26B C26 H26C 111(2) . . ?
O28 C27 C29 122.39(15) . . ?
O28 C27 C26 116.55(15) . . ?
C29 C27 C26 121.06(15) . . ?
C27 C29 C30 127.67(15) . . ?
C27 C29 H29 116.1(10) . . ?
C30 C29 H29 116.2(10) . . ?
O31 C30 O32 118.53(13) . . ?
O31 C30 C29 130.13(14) . . ?
O32 C30 C29 111.34(13) . . ?
C30 O32 C33 116.25(13) . . ?
O32 C33 H33A 111.1(12) . . ?
O32 C33 H33B 112.6(12) . . ?
H33A C33 H33B 108.6(17) . . ?
O32 C33 H33C 108.7(13) . . ?
H33A C33 H33C 109.0(18) . . ?
H33B C33 H33C 106.7(17) . . ?

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
C5 N1 C2 N3 1.32(17) . . . . ?
C6 N1 C2 N3 -179.26(13) . . . . ?
N1 C2 N3 C4 -1.28(17) . . . . ?
N1 C2 N3 C16 179.07(13) . . . . ?
C2 N3 C4 C5 0.74(17) . . . . ?
C16 N3 C4 C5 -179.61(14) . . . . ?
N3 C4 C5 N1 0.06(17) . . . . ?
C2 N1 C5 C4 -0.84(17) . . . . ?
C6 N1 C5 C4 179.75(14) . . . . ?
C2 N1 C6 C12 17.1(2) . . . . ?
C5 N1 C6 C12 -163.61(14) . . . . ?
C2 N1 C6 C11 136.99(16) . . . . ?
C5 N1 C6 C11 -43.7(2) . . . . ?
C2 N1 C6 C7 -102.84(17) . . . . ?
C5 N1 C6 C7 76.48(18) . . . . ?
N1 C6 C7 C8 179.83(13) . . . . ?
C12 C6 C7 C8 59.94(17) . . . . ?
C11 C6 C7 C8 -60.36(17) . . . . ?
C6 C7 C8 C15 -59.48(18) . . . . ?
C6 C7 C8 C9 60.46(18) . . . . ?
C15 C8 C9 C10 59.59(18) . . . . ?
C7 C8 C9 C10 -60.76(18) . . . . ?
C8 C9 C10 C14 -59.58(18) . . . . ?
C8 C9 C10 C11 60.40(18) . . . . ?
N1 C6 C11 C10 -179.86(14) . . . . ?
C12 C6 C11 C10 -60.11(18) . . . . ?
C7 C6 C11 C10 60.06(18) . . . . ?
C14 C10 C11 C6 60.45(19) . . . . ?
C9 C10 C11 C6 -59.92(19) . . . . ?
N1 C6 C12 C13 179.24(12) . . . . ?
C11 C6 C12 C13 59.62(17) . . . . ?
C7 C6 C12 C13 -60.74(17) . . . . ?
C6 C12 C13 C14 -59.77(17) . . . . ?
C6 C12 C13 C15 61.00(17) . . . . ?
C9 C10 C14 C13 59.41(17) . . . . ?
C11 C10 C14 C13 -60.59(18) . . . . ?
C15 C13 C14 C10 -59.90(17) . . . . ?
C12 C13 C14 C10 60.54(18) . . . . ?
C14 C13 C15 C8 60.31(17) . . . . ?
C12 C13 C15 C8 -60.43(18) . . . . ?
C9 C8 C15 C13 -60.06(18) . . . . ?
C7 C8 C15 C13 59.93(18) . . . . ?
C2 N3 C16 C17 106.44(16) . . . . ?
C4 N3 C16 C17 -73.14(18) . . . . ?
C2 N3 C16 C22 -13.8(2) . . . . ?
C4 N3 C16 C22 166.63(14) . . . . ?
C2 N3 C16 C21 -133.48(15) . . . . ?
C4 N3 C16 C21 46.94(19) . . . . ?
N3 C16 C17 C18 179.80(12) . . . . ?
C22 C16 C17 C18 -60.15(16) . . . . ?
C21 C16 C17 C18 60.33(16) . . . . ?
C16 C17 C18 C25 60.25(17) . . . . ?
C16 C17 C18 C19 -60.29(17) . . . . ?
C25 C18 C19 C20 -57.96(18) . . . . ?
C17 C18 C19 C20 61.42(18) . . . . ?
C18 C19 C20 C24 58.38(18) . . . . ?
C18 C19 C20 C21 -61.14(18) . . . . ?
N3 C16 C21 C20 -179.73(12) . . . . ?
C17 C16 C21 C20 -60.14(17) . . . . ?
C22 C16 C21 C20 60.55(16) . . . . ?
C19 C20 C21 C16 59.73(17) . . . . ?
C24 C20 C21 C16 -60.27(18) . . . . ?
N3 C16 C22 C23 -179.69(12) . . . . ?
C17 C16 C22 C23 60.48(16) . . . . ?
C21 C16 C22 C23 -60.30(16) . . . . ?
C16 C22 C23 C25 -60.42(17) . . . . ?
C16 C22 C23 C24 59.99(17) . . . . ?
C19 C20 C24 C23 -58.76(19) . . . . ?
C21 C20 C24 C23 60.44(19) . . . . ?
C25 C23 C24 C20 58.77(19) . . . . ?
C22 C23 C24 C20 -60.25(19) . . . . ?
C19 C18 C25 C23 57.55(17) . . . . ?
C17 C18 C25 C23 -61.81(17) . . . . ?
C24 C23 C25 C18 -58.06(18) . . . . ?
C22 C23 C25 C18 61.67(17) . . . . ?
O28 C27 C29 C30 -178.24(15) . . . . ?
C26 C27 C29 C30 1.6(2) . . . . ?
C27 C29 C30 O31 -0.1(3) . . . . ?
C27 C29 C30 O32 178.91(14) . . . . ?
O31 C30 O32 C33 1.0(2) . . . . ?
C29 C30 O32 C33 -178.07(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034