# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Akhigbe, Joshua'
'Peters, Gretchen'
'Zeller, Matthias'
'Bruckner, Christian'

_publ_contact_author_name        'Bruckner, Christian'
_publ_contact_author_email       c.bruckner@uconn.edu

_publ_section_title              
;
Unexpected Hydroxylamine-induced Ring-closure Reactions
of meso Tetraphenylsecochlorin Bisaldehyde
;

# Attachment '- NitroTTP_ImidazoleTPP_Cifs.cif'

data_09mz434_0m #NitroTTPMonoclinic
_database_code_depnum_ccdc_archive 'CCDC 798353'
#TrackingRef '- NitroTTP_ImidazoleTPP_Cifs.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H33 N5 O3'
_chemical_formula_weight         691.76

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   38.963(16)
_cell_length_b                   9.070(4)
_cell_length_c                   25.863(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.953(5)
_cell_angle_gamma                90.00
_cell_volume                     6902(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1282
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      20.79

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2896
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16363
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_sigmaI/netI    0.1448
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7040
_reflns_number_gt                3065
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'

_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^)+(0.1485P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7040
_refine_ls_number_parameters     480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1951
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_ref         0.2784
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.001
_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
C1 C 0.40382(18) 0.3144(6) 0.2609(2) 0.0392(13) Uani 1 1 d . . .
C2 C 0.40483(17) 0.2389(6) 0.2143(2) 0.0375(12) Uani 1 1 d . . .
C3 C 0.44373(19) 0.2011(6) 0.2228(3) 0.0441(13) Uani 1 1 d . . .
H3 H 0.4745 0.2174 0.2629 0.053 Uiso 1 1 calc R . .
C4 C 0.42944(18) 0.1373(6) 0.1637(3) 0.0447(13) Uani 1 1 d . . .
H4 H 0.4484 0.1026 0.1554 0.054 Uiso 1 1 calc R . .
C5 C 0.38091(17) 0.1317(5) 0.1167(3) 0.0357(12) Uani 1 1 d . . .
C6 C 0.35199(17) 0.0733(5) 0.0496(2) 0.0324(11) Uani 1 1 d . . .
C7 C 0.30525(17) 0.0523(5) 0.0102(2) 0.0313(11) Uani 1 1 d . . .
C8 C 0.27469(18) 0.0024(5) -0.0611(2) 0.0357(12) Uani 1 1 d . . .
H8 H 0.2827 -0.0128 -0.0883 0.043 Uiso 1 1 calc R . .
C9 C 0.23323(18) -0.0180(5) -0.0812(2) 0.0326(11) Uani 1 1 d . . .
H9 H 0.2065 -0.0494 -0.1250 0.039 Uiso 1 1 calc R . .
C10 C 0.23793(17) 0.0178(5) -0.0220(2) 0.0297(11) Uani 1 1 d . . .
C11 C 0.20224(16) -0.0021(5) -0.0212(2) 0.0315(11) Uani 1 1 d . . .
C12 C 0.20375(17) 0.0478(5) 0.0321(2) 0.0326(11) Uani 1 1 d . . .
C13 C 0.17022(17) 0.0267(5) 0.0388(2) 0.0349(12) Uani 1 1 d . . .
H13 H 0.1430 -0.0289 0.0086 0.042 Uiso 1 1 calc R . .
C14 C 0.18402(18) 0.0998(5) 0.0958(2) 0.0370(12) Uani 1 1 d . . .
H14 H 0.1678 0.1065 0.1115 0.044 Uiso 1 1 calc R . .
C15 C 0.22691(17) 0.1642(5) 0.1274(2) 0.0343(12) Uani 1 1 d . . .
C16 C 0.25282(17) 0.2530(5) 0.1865(2) 0.0348(12) Uani 1 1 d . . .
C17 C 0.29650(19) 0.3074(5) 0.2185(2) 0.0371(12) Uani 1 1 d . . .
C18 C 0.31804(19) 0.4234(6) 0.2697(3) 0.0416(13) Uani 1 1 d . . .
H18 H 0.3060 0.4742 0.2868 0.050 Uiso 1 1 calc R . .
C19 C 0.35837(19) 0.4431(6) 0.2873(3) 0.0405(13) Uani 1 1 d . . .
C20 C 0.36393(18) 0.3404(6) 0.2499(2) 0.0395(13) Uani 1 1 d . . .
C21 C 0.44813(18) 0.3595(6) 0.3283(2) 0.0395(13) Uani 1 1 d . . .
C22 C 0.45766(19) 0.3136(6) 0.3878(3) 0.0438(13) Uani 1 1 d . . .
H22 H 0.4365 0.2534 0.3850 0.053 Uiso 1 1 calc R . .
C23 C 0.4980(2) 0.3556(7) 0.4516(3) 0.0496(15) Uani 1 1 d . . .
H23 H 0.5047 0.3208 0.4920 0.060 Uiso 1 1 calc R . .
C24 C 0.52854(19) 0.4476(7) 0.4568(3) 0.0503(15) Uani 1 1 d . . .
H24 H 0.5557 0.4780 0.5003 0.060 Uiso 1 1 calc R . .
C25 C 0.51900(18) 0.4944(7) 0.3979(3) 0.0487(14) Uani 1 1 d . . .
H25 H 0.5396 0.5582 0.4009 0.058 Uiso 1 1 calc R . .
C26 C 0.47968(18) 0.4494(7) 0.3343(3) 0.0490(15) Uani 1 1 d . . .
H26 H 0.4741 0.4801 0.2942 0.059 Uiso 1 1 calc R . .
C27 C 0.37346(17) 0.0228(5) 0.0212(2) 0.0369(12) Uani 1 1 d . . .
C28 C 0.39875(17) 0.1180(6) 0.0151(3) 0.0397(13) Uani 1 1 d . . .
H28 H 0.4028 0.2175 0.0296 0.048 Uiso 1 1 calc R . .
C29 C 0.41788(19) 0.0703(6) -0.0114(3) 0.0458(14) Uani 1 1 d . . .
H29 H 0.4347 0.1371 -0.0156 0.055 Uiso 1 1 calc R . .
C30 C 0.4127(2) -0.0746(7) -0.0321(3) 0.0534(15) Uani 1 1 d . . .
H30 H 0.4262 -0.1075 -0.0502 0.064 Uiso 1 1 calc R . .
C31 C 0.3880(2) -0.1713(6) -0.0264(3) 0.0527(15) Uani 1 1 d . . .
H31 H 0.3842 -0.2708 -0.0409 0.063 Uiso 1 1 calc R . .
C32 C 0.3688(2) -0.1227(6) 0.0006(3) 0.0458(14) Uani 1 1 d . . .
H32 H 0.3522 -0.1900 0.0050 0.055 Uiso 1 1 calc R . .
C33 C 0.16075(17) -0.0816(5) -0.0791(2) 0.0340(12) Uani 1 1 d . . .
C34 C 0.16414(19) -0.2192(5) -0.1009(3) 0.0386(12) Uani 1 1 d . . .
H34 H 0.1932 -0.2613 -0.0783 0.046 Uiso 1 1 calc R . .
C35 C 0.1257(2) -0.2932(6) -0.1548(3) 0.0433(14) Uani 1 1 d . . .
H35 H 0.1287 -0.3839 -0.1698 0.052 Uiso 1 1 calc R . .
C36 C 0.0830(2) -0.2380(6) -0.1872(3) 0.0480(15) Uani 1 1 d . . .
H36 H 0.0567 -0.2910 -0.2237 0.058 Uiso 1 1 calc R . .
C37 C 0.07870(19) -0.1033(6) -0.1660(3) 0.0435(14) Uani 1 1 d . . .
H37 H 0.0494 -0.0649 -0.1877 0.052 Uiso 1 1 calc R . .
C38 C 0.11699(17) -0.0253(5) -0.1135(2) 0.0362(12) Uani 1 1 d . . .
H38 H 0.1136 0.0679 -0.1005 0.043 Uiso 1 1 calc R . .
C39 C 0.23267(18) 0.2942(5) 0.2180(2) 0.0364(12) Uani 1 1 d . . .
C40 C 0.19105(18) 0.3701(6) 0.1794(3) 0.0412(13) Uani 1 1 d . . .
H40 H 0.1753 0.3946 0.1329 0.049 Uiso 1 1 calc R . .
C41 C 0.17298(19) 0.4089(6) 0.2091(3) 0.0453(14) Uani 1 1 d . . .
H41 H 0.1446 0.4589 0.1827 0.054 Uiso 1 1 calc R . .
C42 C 0.1960(2) 0.3753(6) 0.2772(3) 0.0488(15) Uani 1 1 d . . .
H42 H 0.1837 0.4041 0.2975 0.059 Uiso 1 1 calc R . .
C43 C 0.2367(2) 0.3000(6) 0.3154(3) 0.0481(15) Uani 1 1 d . . .
H43 H 0.2523 0.2762 0.3619 0.058 Uiso 1 1 calc R . .
C44 C 0.25514(19) 0.2587(6) 0.2861(3) 0.0424(13) Uani 1 1 d . . .
H44 H 0.2831 0.2062 0.3125 0.051 Uiso 1 1 calc R . .
N5 N 0.38710(16) 0.5705(5) 0.3270(2) 0.0471(12) Uani 1 1 d . . .
N1 N 0.36790(14) 0.1914(4) 0.1501(2) 0.0371(10) Uani 1 1 d . . .
H1 H 0.3396 0.1983 0.1327 0.045 Uiso 1 1 calc R . .
N2 N 0.28139(13) 0.0646(4) 0.03182(19) 0.0307(9) Uani 1 1 d . . .
N3 N 0.23823(14) 0.1285(4) 0.08799(19) 0.0316(9) Uani 1 1 d . . .
H3A H 0.2636 0.1537 0.0974 0.038 Uiso 1 1 calc R . .
N4 N 0.32440(14) 0.2613(5) 0.2062(2) 0.0375(10) Uani 1 1 d . . .
O3 O 0.39114(13) 0.6062(4) 0.37760(19) 0.0581(11) Uani 1 1 d . . .
O4 O 0.40422(14) 0.6399(4) 0.3083(2) 0.0568(11) Uani 1 1 d . . .
O1 O 0.4538(3) 0.9100(8) 0.3958(4) 0.130(2) Uani 1 1 d . . .
H1A H 0.4404 0.8285 0.3851 0.195 Uiso 1 1 calc R . .
C46 C 0.4682(3) 0.9305(9) 0.3596(4) 0.097(3) Uani 1 1 d . . .
H46A H 0.4890 1.0148 0.3786 0.145 Uiso 1 1 calc R . .
H46B H 0.4419 0.9494 0.3114 0.145 Uiso 1 1 calc R . .
H46C H 0.4840 0.8417 0.3632 0.145 Uiso 1 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
C1 0.042(3) 0.045(3) 0.031(3) 0.006(2) 0.024(3) 0.002(2)
C2 0.038(3) 0.047(3) 0.028(3) -0.002(2) 0.021(3) -0.003(2)
C3 0.044(3) 0.054(4) 0.030(3) 0.004(3) 0.023(3) 0.006(3)
C4 0.047(3) 0.052(4) 0.041(3) 0.002(3) 0.031(3) 0.008(3)
C5 0.044(3) 0.030(3) 0.036(3) 0.004(2) 0.028(3) 0.006(2)
C6 0.046(3) 0.028(3) 0.031(3) 0.006(2) 0.028(3) 0.004(2)
C7 0.052(3) 0.020(2) 0.030(3) 0.003(2) 0.030(3) 0.004(2)
C8 0.055(3) 0.028(3) 0.031(3) 0.001(2) 0.031(3) 0.001(2)
C9 0.049(3) 0.023(3) 0.032(3) 0.000(2) 0.029(3) -0.001(2)
C10 0.048(3) 0.019(2) 0.029(3) 0.003(2) 0.028(3) 0.004(2)
C11 0.043(3) 0.026(3) 0.027(3) 0.003(2) 0.024(2) 0.004(2)
C12 0.042(3) 0.026(3) 0.025(3) 0.000(2) 0.020(2) 0.002(2)
C13 0.041(3) 0.035(3) 0.031(3) -0.001(2) 0.025(3) 0.000(2)
C14 0.043(3) 0.041(3) 0.031(3) 0.000(2) 0.026(3) 0.003(2)
C15 0.044(3) 0.037(3) 0.028(3) 0.001(2) 0.026(3) 0.005(2)
C16 0.047(3) 0.037(3) 0.027(3) -0.001(2) 0.027(3) 0.001(2)
C17 0.054(3) 0.035(3) 0.027(3) 0.001(2) 0.029(3) 0.005(3)
C18 0.049(3) 0.046(3) 0.033(3) -0.003(2) 0.028(3) -0.005(3)
C19 0.047(3) 0.040(3) 0.030(3) -0.007(2) 0.023(3) 0.000(3)
C20 0.051(3) 0.042(3) 0.030(3) 0.001(2) 0.029(3) 0.000(3)
C21 0.045(3) 0.049(3) 0.028(3) 0.000(2) 0.025(3) 0.000(3)
C22 0.051(3) 0.050(3) 0.032(3) 0.002(2) 0.028(3) -0.003(3)
C23 0.058(4) 0.062(4) 0.026(3) 0.003(3) 0.026(3) 0.003(3)
C24 0.045(3) 0.068(4) 0.032(3) -0.010(3) 0.023(3) -0.006(3)
C25 0.041(3) 0.066(4) 0.036(3) 0.000(3) 0.023(3) -0.003(3)
C26 0.051(3) 0.067(4) 0.033(3) 0.004(3) 0.030(3) -0.005(3)
C27 0.046(3) 0.038(3) 0.032(3) 0.002(2) 0.029(3) 0.004(2)
C28 0.048(3) 0.039(3) 0.042(3) -0.002(2) 0.034(3) -0.001(3)
C29 0.055(4) 0.051(4) 0.046(3) -0.003(3) 0.039(3) -0.002(3)
C30 0.064(4) 0.059(4) 0.056(4) 0.000(3) 0.048(3) 0.008(3)
C31 0.074(4) 0.042(3) 0.061(4) 0.000(3) 0.052(4) 0.007(3)
C32 0.066(4) 0.035(3) 0.047(3) 0.002(3) 0.042(3) 0.004(3)
C33 0.047(3) 0.037(3) 0.025(3) 0.000(2) 0.027(3) -0.002(2)
C34 0.057(3) 0.032(3) 0.034(3) -0.001(2) 0.034(3) -0.002(3)
C35 0.065(4) 0.038(3) 0.038(3) -0.009(3) 0.039(3) -0.013(3)
C36 0.067(4) 0.050(4) 0.035(3) -0.011(3) 0.037(3) -0.018(3)
C37 0.046(3) 0.057(4) 0.030(3) 0.003(3) 0.027(3) -0.001(3)
C38 0.052(3) 0.033(3) 0.029(3) -0.001(2) 0.028(3) -0.002(2)
C39 0.053(3) 0.036(3) 0.031(3) -0.010(2) 0.032(3) -0.012(2)
C40 0.047(3) 0.045(3) 0.036(3) -0.006(3) 0.030(3) 0.001(3)
C41 0.046(3) 0.051(4) 0.043(3) -0.005(3) 0.032(3) 0.002(3)
C42 0.066(4) 0.049(4) 0.053(4) -0.018(3) 0.048(4) -0.013(3)
C43 0.076(4) 0.046(3) 0.037(3) -0.013(3) 0.044(3) -0.019(3)
C44 0.052(3) 0.045(3) 0.030(3) -0.003(2) 0.027(3) -0.002(3)
N5 0.053(3) 0.049(3) 0.042(3) -0.001(2) 0.032(3) 0.004(2)
N1 0.043(3) 0.045(3) 0.031(2) -0.001(2) 0.027(2) 0.001(2)
N2 0.041(2) 0.029(2) 0.028(2) 0.0035(18) 0.025(2) 0.0048(19)
N3 0.041(2) 0.029(2) 0.027(2) 0.0011(18) 0.023(2) 0.0034(19)
N4 0.042(3) 0.040(3) 0.027(2) -0.0020(19) 0.021(2) -0.004(2)
O3 0.064(3) 0.070(3) 0.038(2) -0.014(2) 0.033(2) 0.001(2)
O4 0.068(3) 0.052(3) 0.064(3) -0.001(2) 0.049(3) -0.004(2)
O1 0.164(7) 0.128(6) 0.153(6) -0.025(5) 0.128(6) -0.030(5)
C46 0.154(8) 0.077(5) 0.098(6) -0.019(5) 0.099(7) -0.031(5)

_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 C20 1.404(7) . ?
C1 C2 1.409(7) . ?
C1 C21 1.497(7) . ?
C2 N1 1.371(6) . ?
C2 C3 1.423(7) . ?
C3 C4 1.366(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.429(7) . ?
C4 H4 0.9500 . ?
C5 N1 1.368(6) . ?
C5 C6 1.414(7) . ?
C6 C7 1.399(7) . ?
C6 C27 1.501(6) . ?
C7 N2 1.369(5) . ?
C7 C8 1.463(6) . ?
C8 C9 1.346(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(6) . ?
C9 H9 0.9500 . ?
C10 N2 1.377(6) . ?
C10 C11 1.415(6) . ?
C11 C12 1.417(6) . ?
C11 C33 1.484(7) . ?
C12 N3 1.372(6) . ?
C12 C13 1.439(6) . ?
C13 C14 1.365(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.419(7) . ?
C14 H14 0.9500 . ?
C15 N3 1.388(5) . ?
C15 C16 1.407(7) . ?
C16 C17 1.407(7) . ?
C16 C39 1.503(6) . ?
C17 N4 1.381(6) . ?
C17 C18 1.452(7) . ?
C18 C19 1.330(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.459(7) . ?
C19 N5 1.462(7) . ?
C20 N4 1.372(6) . ?
C21 C22 1.390(7) . ?
C21 C26 1.396(7) . ?
C22 C23 1.393(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.391(7) . ?
C27 C28 1.394(7) . ?
C28 C29 1.373(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(7) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.404(7) . ?
C33 C34 1.412(7) . ?
C34 C35 1.378(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.376(8) . ?
C35 H35 0.9500 . ?
C36 C37 1.393(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.384(7) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.396(7) . ?
C39 C40 1.406(7) . ?
C40 C41 1.386(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.389(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(8) . ?
C42 H42 0.9500 . ?
C43 C44 1.395(7) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
N5 O4 1.224(5) . ?
N5 O3 1.253(5) . ?
N1 H1 0.8800 . ?
N3 H3A 0.8800 . ?
O1 C46 1.385(8) . ?
O1 H1A 0.8400 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
C20 C1 C2 123.8(5) . . ?
C20 C1 C21 118.0(4) . . ?
C2 C1 C21 118.1(5) . . ?
N1 C2 C1 126.3(5) . . ?
N1 C2 C3 106.1(4) . . ?
C1 C2 C3 127.5(5) . . ?
C4 C3 C2 108.5(5) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 C5 108.0(5) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
N1 C5 C6 126.6(5) . . ?
N1 C5 C4 106.2(4) . . ?
C6 C5 C4 127.1(4) . . ?
C7 C6 C5 123.7(4) . . ?
C7 C6 C27 118.6(4) . . ?
C5 C6 C27 117.6(4) . . ?
N2 C7 C6 126.8(4) . . ?
N2 C7 C8 109.3(4) . . ?
C6 C7 C8 123.8(4) . . ?
C9 C8 C7 108.0(4) . . ?
C9 C8 H8 126.0 . . ?
C7 C8 H8 126.0 . . ?
C8 C9 C10 105.7(5) . . ?
C8 C9 H9 127.1 . . ?
C10 C9 H9 127.1 . . ?
N2 C10 C11 126.4(4) . . ?
N2 C10 C9 110.9(4) . . ?
C11 C10 C9 122.6(4) . . ?
C10 C11 C12 124.0(4) . . ?
C10 C11 C33 118.6(4) . . ?
C12 C11 C33 117.3(4) . . ?
N3 C12 C11 125.6(4) . . ?
N3 C12 C13 106.5(4) . . ?
C11 C12 C13 127.9(4) . . ?
C14 C13 C12 108.6(4) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
C13 C14 C15 107.6(4) . . ?
C13 C14 H14 126.2 . . ?
C15 C14 H14 126.2 . . ?
N3 C15 C16 125.7(4) . . ?
N3 C15 C14 107.6(4) . . ?
C16 C15 C14 126.6(4) . . ?
C17 C16 C15 124.7(4) . . ?
C17 C16 C39 117.0(4) . . ?
C15 C16 C39 118.3(4) . . ?
N4 C17 C16 126.2(4) . . ?
N4 C17 C18 110.9(5) . . ?
C16 C17 C18 123.0(5) . . ?
C19 C18 C17 104.9(5) . . ?
C19 C18 H18 127.5 . . ?
C17 C18 H18 127.5 . . ?
C18 C19 C20 110.0(5) . . ?
C18 C19 N5 122.4(5) . . ?
C20 C19 N5 126.3(5) . . ?
N4 C20 C1 125.2(5) . . ?
N4 C20 C19 107.7(4) . . ?
C1 C20 C19 126.8(5) . . ?
C22 C21 C26 118.4(5) . . ?
C22 C21 C1 118.3(5) . . ?
C26 C21 C1 123.3(4) . . ?
C21 C22 C23 120.3(5) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.1(5) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.6(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 120.9(5) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C32 C27 C28 117.9(5) . . ?
C32 C27 C6 120.3(4) . . ?
C28 C27 C6 121.9(4) . . ?
C29 C28 C27 121.1(5) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.2(5) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.9(5) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 119.6(5) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C31 C32 C27 121.2(5) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C38 C33 C34 117.5(5) . . ?
C38 C33 C11 122.0(4) . . ?
C34 C33 C11 120.5(5) . . ?
C35 C34 C33 120.7(5) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 121.2(5) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 119.2(5) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C38 C37 C36 120.3(5) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C33 121.1(5) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?
C44 C39 C40 119.2(4) . . ?
C44 C39 C16 120.5(5) . . ?
C40 C39 C16 120.3(4) . . ?
C41 C40 C39 119.9(5) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C40 C41 C42 120.5(5) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C43 C42 C41 119.9(5) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.2(5) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C43 C44 C39 120.2(5) . . ?
C43 C44 H44 119.9 . . ?
C39 C44 H44 119.9 . . ?
O4 N5 O3 123.5(5) . . ?
O4 N5 C19 119.6(4) . . ?
O3 N5 C19 116.9(4) . . ?
C5 N1 C2 111.1(4) . . ?
C5 N1 H1 124.5 . . ?
C2 N1 H1 124.5 . . ?
C7 N2 C10 106.0(4) . . ?
C12 N3 C15 109.5(4) . . ?
C12 N3 H3A 125.2 . . ?
C15 N3 H3A 125.2 . . ?
C20 N4 C17 106.4(4) . . ?
C46 O1 H1A 109.5 . . ?
O1 C46 H46A 109.5 . . ?
O1 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O1 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C20 C1 C2 N1 5.9(8) . . . . ?
C21 C1 C2 N1 -178.8(5) . . . . ?
C20 C1 C2 C3 -176.5(5) . . . . ?
C21 C1 C2 C3 -1.2(8) . . . . ?
N1 C2 C3 C4 2.0(6) . . . . ?
C1 C2 C3 C4 -176.0(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 N1 -0.8(6) . . . . ?
C3 C4 C5 C6 -179.4(5) . . . . ?
N1 C5 C6 C7 -8.0(8) . . . . ?
C4 C5 C6 C7 170.3(5) . . . . ?
N1 C5 C6 C27 175.9(4) . . . . ?
C4 C5 C6 C27 -5.8(7) . . . . ?
C5 C6 C7 N2 -9.4(7) . . . . ?
C27 C6 C7 N2 166.7(4) . . . . ?
C5 C6 C7 C8 175.2(4) . . . . ?
C27 C6 C7 C8 -8.7(7) . . . . ?
N2 C7 C8 C9 -1.4(5) . . . . ?
C6 C7 C8 C9 174.7(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 N2 2.3(5) . . . . ?
C8 C9 C10 C11 -174.6(4) . . . . ?
N2 C10 C11 C12 11.4(7) . . . . ?
C9 C10 C11 C12 -172.1(4) . . . . ?
N2 C10 C11 C33 -167.7(4) . . . . ?
C9 C10 C11 C33 8.7(6) . . . . ?
C10 C11 C12 N3 3.9(7) . . . . ?
C33 C11 C12 N3 -177.0(4) . . . . ?
C10 C11 C12 C13 -176.8(4) . . . . ?
C33 C11 C12 C13 2.3(7) . . . . ?
N3 C12 C13 C14 2.8(5) . . . . ?
C11 C12 C13 C14 -176.6(5) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C13 C14 C15 N3 0.2(5) . . . . ?
C13 C14 C15 C16 178.1(5) . . . . ?
N3 C15 C16 C17 -6.5(8) . . . . ?
C14 C15 C16 C17 176.0(5) . . . . ?
N3 C15 C16 C39 173.1(4) . . . . ?
C14 C15 C16 C39 -4.4(7) . . . . ?
C15 C16 C17 N4 -13.4(8) . . . . ?
C39 C16 C17 N4 167.0(4) . . . . ?
C15 C16 C17 C18 166.1(5) . . . . ?
C39 C16 C17 C18 -13.5(7) . . . . ?
N4 C17 C18 C19 -0.6(6) . . . . ?
C16 C17 C18 C19 179.8(5) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C17 C18 C19 N5 166.9(5) . . . . ?
C2 C1 C20 N4 21.6(8) . . . . ?
C21 C1 C20 N4 -153.6(5) . . . . ?
C2 C1 C20 C19 -165.7(5) . . . . ?
C21 C1 C20 C19 19.1(8) . . . . ?
C18 C19 C20 N4 2.6(6) . . . . ?
N5 C19 C20 N4 -164.9(5) . . . . ?
C18 C19 C20 C1 -171.1(5) . . . . ?
N5 C19 C20 C1 21.4(8) . . . . ?
C20 C1 C21 C22 50.9(7) . . . . ?
C2 C1 C21 C22 -124.6(5) . . . . ?
C20 C1 C21 C26 -126.9(6) . . . . ?
C2 C1 C21 C26 57.5(7) . . . . ?
C26 C21 C22 C23 -0.7(8) . . . . ?
C1 C21 C22 C23 -178.7(5) . . . . ?
C21 C22 C23 C24 2.2(9) . . . . ?
C22 C23 C24 C25 -1.6(9) . . . . ?
C23 C24 C25 C26 -0.5(9) . . . . ?
C24 C25 C26 C21 2.0(9) . . . . ?
C22 C21 C26 C25 -1.4(8) . . . . ?
C1 C21 C26 C25 176.4(5) . . . . ?
C7 C6 C27 C32 -55.5(6) . . . . ?
C5 C6 C27 C32 120.8(6) . . . . ?
C7 C6 C27 C28 125.0(5) . . . . ?
C5 C6 C27 C28 -58.6(6) . . . . ?
C32 C27 C28 C29 1.1(8) . . . . ?
C6 C27 C28 C29 -179.5(5) . . . . ?
C27 C28 C29 C30 -0.7(8) . . . . ?
C28 C29 C30 C31 0.4(9) . . . . ?
C29 C30 C31 C32 -0.5(9) . . . . ?
C30 C31 C32 C27 0.9(9) . . . . ?
C28 C27 C32 C31 -1.2(8) . . . . ?
C6 C27 C32 C31 179.4(5) . . . . ?
C10 C11 C33 C38 -130.8(5) . . . . ?
C12 C11 C33 C38 50.0(6) . . . . ?
C10 C11 C33 C34 49.9(6) . . . . ?
C12 C11 C33 C34 -129.3(5) . . . . ?
C38 C33 C34 C35 1.0(7) . . . . ?
C11 C33 C34 C35 -179.7(4) . . . . ?
C33 C34 C35 C36 -2.3(7) . . . . ?
C34 C35 C36 C37 1.4(8) . . . . ?
C35 C36 C37 C38 0.8(7) . . . . ?
C36 C37 C38 C33 -2.1(7) . . . . ?
C34 C33 C38 C37 1.2(7) . . . . ?
C11 C33 C38 C37 -178.1(4) . . . . ?
C17 C16 C39 C44 -57.9(6) . . . . ?
C15 C16 C39 C44 122.5(5) . . . . ?
C17 C16 C39 C40 121.7(5) . . . . ?
C15 C16 C39 C40 -57.9(6) . . . . ?
C44 C39 C40 C41 0.2(8) . . . . ?
C16 C39 C40 C41 -179.4(5) . . . . ?
C39 C40 C41 C42 0.9(8) . . . . ?
C40 C41 C42 C43 -1.3(8) . . . . ?
C41 C42 C43 C44 0.6(8) . . . . ?
C42 C43 C44 C39 0.5(8) . . . . ?
C40 C39 C44 C43 -0.9(8) . . . . ?
C16 C39 C44 C43 178.7(5) . . . . ?
C18 C19 N5 O4 -132.5(5) . . . . ?
C20 C19 N5 O4 33.6(8) . . . . ?
C18 C19 N5 O3 44.5(7) . . . . ?
C20 C19 N5 O3 -149.4(5) . . . . ?
C6 C5 N1 C2 -179.3(5) . . . . ?
C4 C5 N1 C2 2.1(5) . . . . ?
C1 C2 N1 C5 175.5(5) . . . . ?
C3 C2 N1 C5 -2.5(6) . . . . ?
C6 C7 N2 C10 -173.2(4) . . . . ?
C8 C7 N2 C10 2.7(5) . . . . ?
C11 C10 N2 C7 173.6(4) . . . . ?
C9 C10 N2 C7 -3.1(5) . . . . ?
C11 C12 N3 C15 176.7(4) . . . . ?
C13 C12 N3 C15 -2.7(5) . . . . ?
C16 C15 N3 C12 -176.3(5) . . . . ?
C14 C15 N3 C12 1.6(5) . . . . ?
C1 C20 N4 C17 171.0(5) . . . . ?
C19 C20 N4 C17 -2.8(5) . . . . ?
C16 C17 N4 C20 -178.2(5) . . . . ?
C18 C17 N4 C20 2.2(5) . . . . ?

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
O1 H1A O4 0.84 2.28 3.021(8) 147.7 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.316
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.135

data_09mz366_0m #ImidazoleTTP-triclinic
_database_code_depnum_ccdc_archive 'CCDC 798354'
#TrackingRef '- NitroTTP_ImidazoleTPP_Cifs.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H29 N5'
_chemical_formula_weight         615.71

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.334(2)
_cell_length_b                   10.352(3)
_cell_length_c                   12.149(4)
_cell_angle_alpha                94.288(5)
_cell_angle_beta                 99.895(5)
_cell_angle_gamma                101.107(5)
_cell_volume                     765.2(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1342
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.37

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5295
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'

_exptl_special_details           
;
Nitrogen atom N3 is disordered over four chemically equivalent positions
and across the inversion center of the molecule. It was thus refined as
being disordered over the four positions with a combined occupancy of one
half. The four partially occupied nitrogen atoms were constrained to have
the same positions and thermal parameters as the carbon atoms it is
sharing the site with. Occupancies of the N atoms refined to 0.090(4),
0.061(3), 0.171(3) and 0.171(3).

The N-H hydrogen atoms were refined as disordered over the two alternative
sites, the occupancy ratio refined to 0.663(4) to 0.337(4).

The occupancies of N atom and H atom, while refined independently of each
other, follow the same trend (the dinitrogen heterocycle seems to be not
protonated).
;

_diffrn_ambient_temperature      100(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 AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7609
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.1062
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3744
_reflns_number_gt                2093
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'

_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^)+(0.0351P)^2^+0.6297P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.004
_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
N1 N 0.3633(4) 0.5132(2) 0.6446(2) 0.0209(5) Uani 1 1 d . A .
H1 H 0.4056 0.5214 0.5797 0.025 Uiso 0.663(4) 1 calc PR . .
N2 N 0.2357(4) 0.3626(2) 0.4226(2) 0.0203(5) Uani 1 1 d . A .
H2A H 0.3526 0.4221 0.4557 0.024 Uiso 0.337(4) 1 calc PR . .
C1 C 0.4706(4) 0.5824(3) 0.7460(2) 0.0201(6) Uani 1 1 d . . .
C2 C 0.3475(5) 0.5408(3) 0.8287(3) 0.0265(7) Uani 0.903(4) 1 d P A 1
H2 H 0.3835 0.5724 0.9064 0.032 Uiso 0.903(4) 1 calc PR A 1
N3A N 0.3475(5) 0.5408(3) 0.8287(3) 0.0265(7) Uani 0.097(4) 1 d P A 2
C3 C 0.1700(5) 0.4484(3) 0.7775(2) 0.0236(8) Uani 0.94(3) 1 d P A 1
H3 H 0.0584 0.4040 0.8128 0.028 Uiso 0.94(3) 1 calc PR A 1
N3B N 0.1700(5) 0.4484(3) 0.7775(2) 0.0236(8) Uani 0.06(3) 1 d P A 2
C4 C 0.1796(4) 0.4292(3) 0.6616(2) 0.0198(6) Uani 1 1 d . . .
C5 C 0.0375(4) 0.3337(3) 0.5806(2) 0.0195(6) Uani 1 1 d . A .
C6 C -0.1468(4) 0.2465(3) 0.6180(2) 0.0205(6) Uani 1 1 d . . .
C7 C -0.3031(5) 0.2991(3) 0.6642(3) 0.0250(7) Uani 1 1 d . A .
H7 H -0.2947 0.3920 0.6707 0.030 Uiso 1 1 calc R . .
C8 C -0.4709(5) 0.2164(3) 0.7008(3) 0.0269(7) Uani 1 1 d . . .
H8 H -0.5752 0.2533 0.7333 0.032 Uiso 1 1 calc R A .
C9 C -0.4873(5) 0.0817(3) 0.6902(3) 0.0278(7) Uani 1 1 d . A .
H9 H -0.6038 0.0255 0.7143 0.033 Uiso 1 1 calc R . .
C10 C -0.3331(5) 0.0278(3) 0.6443(3) 0.0289(7) Uani 1 1 d . . .
H10 H -0.3436 -0.0654 0.6374 0.035 Uiso 1 1 calc R A .
C11 C -0.1640(5) 0.1095(3) 0.6087(3) 0.0262(7) Uani 1 1 d . A .
H11 H -0.0587 0.0720 0.5777 0.031 Uiso 1 1 calc R . .
C12 C 0.0634(4) 0.3084(3) 0.4698(2) 0.0196(6) Uani 1 1 d . . .
C13 C -0.0942(5) 0.2172(3) 0.3866(2) 0.0248(8) Uani 0.83(3) 1 d P A 1
H13 H -0.2300 0.1672 0.3975 0.030 Uiso 0.83(3) 1 calc PR A 1
N3C N -0.0942(5) 0.2172(3) 0.3866(2) 0.0248(8) Uani 0.17(3) 1 d P A 2
C14 C -0.0168(4) 0.2151(3) 0.2920(2) 0.0234(8) Uani 0.83(3) 1 d P A 1
H14 H -0.0859 0.1631 0.2228 0.028 Uiso 0.83(3) 1 calc PR A 1
N3D N -0.0168(4) 0.2151(3) 0.2920(2) 0.0234(8) Uani 0.17(3) 1 d P A 2
C15 C 0.1906(4) 0.3060(3) 0.3139(2) 0.0206(6) Uani 1 1 d . . .
C16 C 0.6742(5) 0.6701(3) 0.7658(2) 0.0207(6) Uani 1 1 d . . .
C17 C 0.7523(5) 0.7423(3) 0.8809(2) 0.0232(7) Uani 1 1 d . . .
C18 C 0.6262(5) 0.8210(3) 0.9267(3) 0.0286(7) Uani 1 1 d . A .
H18 H 0.4894 0.8286 0.8842 0.034 Uiso 1 1 calc R . .
C19 C 0.6988(6) 0.8879(3) 1.0335(3) 0.0336(8) Uani 1 1 d . . .
H19 H 0.6107 0.9403 1.0642 0.040 Uiso 1 1 calc R A .
C20 C 0.8965(6) 0.8792(3) 1.0952(3) 0.0372(8) Uani 1 1 d . A .
H20 H 0.9462 0.9265 1.1681 0.045 Uiso 1 1 calc R . .
C21 C 1.0242(5) 0.8017(3) 1.0518(3) 0.0359(8) Uani 1 1 d . . .
H21 H 1.1617 0.7958 1.0946 0.043 Uiso 1 1 calc R A .
C22 C 0.9514(5) 0.7328(3) 0.9461(3) 0.0315(7) Uani 1 1 d . A .
H22 H 1.0383 0.6781 0.9174 0.038 Uiso 1 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
N1 0.0200(13) 0.0168(12) 0.0231(14) -0.0039(10) 0.0012(10) 0.0018(10)
N2 0.0199(13) 0.0152(12) 0.0223(14) -0.0017(10) -0.0012(10) 0.0012(10)
C1 0.0161(14) 0.0198(14) 0.0238(16) -0.0018(12) 0.0049(12) 0.0028(11)
C2 0.0265(17) 0.0233(15) 0.0264(17) -0.0035(12) 0.0030(13) 0.0012(13)
N3A 0.0265(17) 0.0233(15) 0.0264(17) -0.0035(12) 0.0030(13) 0.0012(13)
C3 0.0216(16) 0.0230(15) 0.0263(18) -0.0019(12) 0.0107(13) 0.0010(12)
N3B 0.0216(16) 0.0230(15) 0.0263(18) -0.0019(12) 0.0107(13) 0.0010(12)
C4 0.0148(14) 0.0183(14) 0.0276(17) 0.0018(12) 0.0082(12) 0.0034(11)
C5 0.0143(14) 0.0175(14) 0.0264(17) -0.0001(12) 0.0034(12) 0.0040(11)
C6 0.0196(15) 0.0196(14) 0.0194(16) 0.0009(11) -0.0002(12) 0.0010(12)
C7 0.0214(16) 0.0215(15) 0.0333(18) 0.0011(13) 0.0078(13) 0.0056(12)
C8 0.0175(15) 0.0307(17) 0.0341(19) 0.0030(14) 0.0070(13) 0.0071(13)
C9 0.0189(16) 0.0290(17) 0.0317(19) 0.0031(14) 0.0049(13) -0.0041(13)
C10 0.0295(18) 0.0168(14) 0.0347(19) 0.0007(13) -0.0010(14) -0.0024(13)
C11 0.0247(16) 0.0217(15) 0.0297(18) -0.0011(13) 0.0019(13) 0.0032(13)
C12 0.0139(14) 0.0171(14) 0.0258(16) -0.0021(12) 0.0014(12) 0.0021(11)
C13 0.0181(16) 0.0235(15) 0.0281(18) -0.0022(12) 0.0017(13) -0.0026(12)
N3C 0.0181(16) 0.0235(15) 0.0281(18) -0.0022(12) 0.0017(13) -0.0026(12)
C14 0.0195(15) 0.0219(15) 0.0244(18) -0.0028(12) 0.0015(12) -0.0021(12)
N3D 0.0195(15) 0.0219(15) 0.0244(18) -0.0028(12) 0.0015(12) -0.0021(12)
C15 0.0190(15) 0.0164(14) 0.0239(16) -0.0014(12) 0.0005(12) 0.0023(11)
C16 0.0193(15) 0.0184(14) 0.0235(16) -0.0003(12) 0.0022(12) 0.0047(12)
C17 0.0240(16) 0.0194(14) 0.0214(16) -0.0013(12) 0.0009(13) -0.0029(12)
C18 0.0305(18) 0.0256(16) 0.0257(18) -0.0029(13) 0.0021(14) 0.0014(13)
C19 0.042(2) 0.0288(17) 0.0274(19) -0.0061(14) 0.0065(16) 0.0044(15)
C20 0.048(2) 0.0341(19) 0.0207(18) -0.0030(14) 0.0001(16) -0.0047(16)
C21 0.0310(19) 0.042(2) 0.0266(19) 0.0045(15) -0.0057(15) -0.0019(16)
C22 0.0314(18) 0.0319(18) 0.0271(18) 0.0010(14) -0.0002(14) 0.0025(14)

_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 C4 1.368(3) . ?
N1 C1 1.373(4) . ?
N1 H1 0.8800 . ?
N2 C15 1.363(4) . ?
N2 C12 1.364(3) . ?
N2 H2A 0.8800 . ?
C1 C16 1.398(4) . ?
C1 C2 1.417(4) . ?
C2 C3 1.350(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.421(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(4) . ?
C5 C12 1.395(4) . ?
C5 C6 1.491(4) . ?
C6 C7 1.394(4) . ?
C6 C11 1.396(4) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.434(4) . ?
C13 C14 1.325(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.431(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(4) 2_666 ?
C16 C15 1.403(4) 2_666 ?
C16 C17 1.491(4) . ?
C17 C22 1.394(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C4 N1 C1 108.4(2) . . ?
C4 N1 H1 125.8 . . ?
C1 N1 H1 125.8 . . ?
C15 N2 C12 106.3(2) . . ?
C15 N2 H2A 126.9 . . ?
C12 N2 H2A 126.9 . . ?
N1 C1 C16 126.0(3) . . ?
N1 C1 C2 107.8(2) . . ?
C16 C1 C2 126.0(3) . . ?
C3 C2 C1 108.0(3) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
C2 C3 C4 107.9(3) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 125.6(3) . . ?
N1 C4 C3 107.9(2) . . ?
C5 C4 C3 126.3(2) . . ?
C12 C5 C4 125.1(2) . . ?
C12 C5 C6 117.6(2) . . ?
C4 C5 C6 117.2(3) . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 C5 121.3(3) . . ?
C11 C6 C5 120.1(3) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N2 C12 C5 127.4(2) . . ?
N2 C12 C13 109.1(2) . . ?
C5 C12 C13 123.5(3) . . ?
C14 C13 C12 107.8(3) . . ?
C14 C13 H13 126.1 . . ?
C12 C13 H13 126.1 . . ?
C13 C14 C15 106.9(3) . . ?
C13 C14 H14 126.5 . . ?
C15 C14 H14 126.5 . . ?
N2 C15 C16 126.1(3) . 2_666 ?
N2 C15 C14 109.8(2) . . ?
C16 C15 C14 124.1(3) 2_666 . ?
C1 C16 C15 125.0(3) . 2_666 ?
C1 C16 C17 116.8(3) . . ?
C15 C16 C17 118.2(2) 2_666 . ?
C22 C17 C18 118.0(3) . . ?
C22 C17 C16 121.4(3) . . ?
C18 C17 C16 120.6(3) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?

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
C4 N1 C1 C16 174.5(3) . . . . ?
C4 N1 C1 C2 -0.6(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C16 C1 C2 C3 -175.1(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 N1 C4 C5 -174.0(3) . . . . ?
C1 N1 C4 C3 1.0(3) . . . . ?
C2 C3 C4 N1 -1.0(3) . . . . ?
C2 C3 C4 C5 174.0(3) . . . . ?
N1 C4 C5 C12 0.8(4) . . . . ?
C3 C4 C5 C12 -173.3(3) . . . . ?
N1 C4 C5 C6 176.5(3) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C12 C5 C6 C7 -124.7(3) . . . . ?
C4 C5 C6 C7 59.3(4) . . . . ?
C12 C5 C6 C11 56.2(4) . . . . ?
C4 C5 C6 C11 -119.8(3) . . . . ?
C11 C6 C7 C8 0.5(4) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C6 -0.2(5) . . . . ?
C7 C6 C11 C10 0.2(4) . . . . ?
C5 C6 C11 C10 179.3(3) . . . . ?
C15 N2 C12 C5 178.7(3) . . . . ?
C15 N2 C12 C13 -1.0(3) . . . . ?
C4 C5 C12 N2 5.5(5) . . . . ?
C6 C5 C12 N2 -170.1(3) . . . . ?
C4 C5 C12 C13 -174.9(3) . . . . ?
C6 C5 C12 C13 9.4(4) . . . . ?
N2 C12 C13 C14 0.9(3) . . . . ?
C5 C12 C13 C14 -178.7(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C12 N2 C15 C16 -178.3(3) . . . 2_666 ?
C12 N2 C15 C14 0.7(3) . . . . ?
C13 C14 C15 N2 -0.1(3) . . . . ?
C13 C14 C15 C16 178.9(3) . . . 2_666 ?
N1 C1 C16 C15 -4.9(4) . . . 2_666 ?
C2 C1 C16 C15 169.3(3) . . . 2_666 ?
N1 C1 C16 C17 175.6(3) . . . . ?
C2 C1 C16 C17 -10.2(4) . . . . ?
C1 C16 C17 C22 122.3(3) . . . . ?
C15 C16 C17 C22 -57.2(4) 2_666 . . . ?
C1 C16 C17 C18 -57.3(4) . . . . ?
C15 C16 C17 C18 123.2(3) 2_666 . . . ?
C22 C17 C18 C19 0.4(4) . . . . ?
C16 C17 C18 C19 -180.0(3) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C17 1.4(5) . . . . ?
C18 C17 C22 C21 -1.5(5) . . . . ?
C16 C17 C22 C21 178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.059