# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_120410b_0m
_database_code_depnum_ccdc_archive 'CCDC 908906'
#TrackingRef 'TIE-Br-Acetone.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H36 Br I4 N'
_chemical_formula_weight         853.99
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   13.4297(11)
_cell_length_b                   14.0614(12)
_cell_length_c                   15.1348(13)
_cell_angle_alpha                98.1200(10)
_cell_angle_beta                 101.3600(10)
_cell_angle_gamma                106.2410(10)
_cell_volume                     2631.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4721
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.49
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    6.259
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_T_max  0.5205
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      110(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            13160
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.25
_reflns_number_total             9423
_reflns_number_gt                7843
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0286P)^2^+3.4025P] 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         9423
_refine_ls_number_parameters     479
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.022
_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
Br1 Br 0.71806(5) 0.36242(4) 0.89060(4) 0.02117(13) Uani 1 1 d . . .
Br2 Br 0.13500(5) 0.80166(5) 0.63316(4) 0.02470(14) Uani 1 1 d . . .
C1 C 0.5988(4) 0.7989(4) 0.1806(4) 0.0212(13) Uani 1 1 d . . .
H1A H 0.5966 0.7278 0.1800 0.025 Uiso 1 1 calc R . .
H1B H 0.5285 0.7972 0.1436 0.025 Uiso 1 1 calc R . .
C2 C 0.6836(5) 0.8459(4) 0.1331(4) 0.0255(14) Uani 1 1 d . . .
H2A H 0.7544 0.8458 0.1674 0.031 Uiso 1 1 calc R . .
H2B H 0.6870 0.9170 0.1325 0.031 Uiso 1 1 calc R . .
C3 C 0.6578(5) 0.7866(5) 0.0347(4) 0.0270(14) Uani 1 1 d . . .
H3A H 0.6547 0.7157 0.0362 0.032 Uiso 1 1 calc R . .
H3B H 0.5861 0.7857 0.0015 0.032 Uiso 1 1 calc R . .
C4 C 0.7385(5) 0.8298(5) -0.0178(4) 0.0287(15) Uani 1 1 d . . .
H4A H 0.7424 0.9002 -0.0192 0.043 Uiso 1 1 calc R . .
H4B H 0.7164 0.7899 -0.0809 0.043 Uiso 1 1 calc R . .
H4C H 0.8089 0.8274 0.0127 0.043 Uiso 1 1 calc R . .
C5 C 0.7153(4) 0.8509(4) 0.3412(4) 0.0217(13) Uani 1 1 d . . .
H5A H 0.7233 0.8910 0.4030 0.026 Uiso 1 1 calc R . .
H5B H 0.7754 0.8868 0.3170 0.026 Uiso 1 1 calc R . .
C6 C 0.7269(5) 0.7489(4) 0.3529(4) 0.0237(14) Uani 1 1 d . . .
H6A H 0.7080 0.7032 0.2918 0.028 Uiso 1 1 calc R . .
H6B H 0.6778 0.7175 0.3892 0.028 Uiso 1 1 calc R . .
C7 C 0.8420(5) 0.7637(5) 0.4023(4) 0.0261(14) Uani 1 1 d . . .
H7A H 0.8893 0.7867 0.3617 0.031 Uiso 1 1 calc R . .
H7B H 0.8636 0.8176 0.4585 0.031 Uiso 1 1 calc R . .
C8 C 0.8580(5) 0.6681(5) 0.4292(5) 0.0307(15) Uani 1 1 d . . .
H8A H 0.8097 0.6436 0.4677 0.046 Uiso 1 1 calc R . .
H8B H 0.9323 0.6829 0.4637 0.046 Uiso 1 1 calc R . .
H8C H 0.8423 0.6160 0.3735 0.046 Uiso 1 1 calc R . .
C9 C 0.5157(4) 0.7899(5) 0.3083(4) 0.0251(14) Uani 1 1 d . . .
H9A H 0.4501 0.7862 0.2627 0.030 Uiso 1 1 calc R . .
H9B H 0.5183 0.7199 0.3056 0.030 Uiso 1 1 calc R . .
C10 C 0.5053(5) 0.8294(5) 0.4027(4) 0.0326(16) Uani 1 1 d . . .
H10A H 0.4927 0.8957 0.4049 0.039 Uiso 1 1 calc R . .
H10B H 0.5721 0.8387 0.4494 0.039 Uiso 1 1 calc R . .
C11 C 0.4097(6) 0.7516(7) 0.4232(5) 0.059(2) Uani 1 1 d . . .
H11A H 0.3447 0.7379 0.3730 0.071 Uiso 1 1 calc R . .
H11B H 0.4253 0.6871 0.4254 0.071 Uiso 1 1 calc R . .
C12 C 0.3894(7) 0.7901(8) 0.5124(6) 0.076(3) Uani 1 1 d . . .
H12A H 0.4523 0.8003 0.5625 0.114 Uiso 1 1 calc R . .
H12B H 0.3272 0.7407 0.5226 0.114 Uiso 1 1 calc R . .
H12C H 0.3753 0.8546 0.5107 0.114 Uiso 1 1 calc R . .
C13 C 0.6167(5) 0.9594(4) 0.2851(4) 0.0235(14) Uani 1 1 d . . .
H13A H 0.6819 0.9959 0.2675 0.028 Uiso 1 1 calc R . .
H13B H 0.6240 0.9898 0.3501 0.028 Uiso 1 1 calc R . .
C14 C 0.5205(5) 0.9766(4) 0.2254(4) 0.0255(14) Uani 1 1 d . . .
H14A H 0.5151 0.9516 0.1595 0.031 Uiso 1 1 calc R . .
H14B H 0.4540 0.9387 0.2403 0.031 Uiso 1 1 calc R . .
C15 C 0.5333(7) 1.0878(6) 0.2426(6) 0.069(3) Uani 1 1 d . . .
H15A H 0.5996 1.1240 0.2263 0.083 Uiso 1 1 calc R . .
H15B H 0.5432 1.1121 0.3094 0.083 Uiso 1 1 calc R . .
C16 C 0.4422(6) 1.1165(6) 0.1909(6) 0.052(2) Uani 1 1 d . . .
H16A H 0.4300 1.0914 0.1246 0.078 Uiso 1 1 calc R . .
H16B H 0.4599 1.1904 0.2037 0.078 Uiso 1 1 calc R . .
H16C H 0.3772 1.0864 0.2105 0.078 Uiso 1 1 calc R . .
C17 C 0.1573(4) 0.3347(4) 0.1956(4) 0.0193(13) Uani 1 1 d . . .
H17A H 0.1639 0.2792 0.1513 0.023 Uiso 1 1 calc R . .
H17B H 0.2137 0.3974 0.1951 0.023 Uiso 1 1 calc R . .
C18 C 0.1803(4) 0.3117(4) 0.2906(4) 0.0179(12) Uani 1 1 d . . .
H18A H 0.1143 0.2666 0.3009 0.021 Uiso 1 1 calc R . .
H18B H 0.2049 0.3752 0.3378 0.021 Uiso 1 1 calc R . .
C19 C 0.2670(5) 0.2601(5) 0.2987(4) 0.0232(13) Uani 1 1 d . . .
H19A H 0.2392 0.1943 0.2543 0.028 Uiso 1 1 calc R . .
H19B H 0.3296 0.3027 0.2817 0.028 Uiso 1 1 calc R . .
C20 C 0.3030(5) 0.2422(5) 0.3945(4) 0.0282(15) Uani 1 1 d . . .
H20A H 0.3294 0.3069 0.4391 0.042 Uiso 1 1 calc R . .
H20B H 0.3605 0.2118 0.3961 0.042 Uiso 1 1 calc R . .
H20C H 0.2425 0.1964 0.4103 0.042 Uiso 1 1 calc R . .
C21 C 0.0248(5) 0.4184(4) 0.2335(4) 0.0181(12) Uani 1 1 d . . .
H21A H 0.0176 0.3850 0.2863 0.022 Uiso 1 1 calc R . .
H21B H -0.0452 0.4267 0.2078 0.022 Uiso 1 1 calc R . .
C22 C 0.1074(5) 0.5229(4) 0.2692(4) 0.0234(14) Uani 1 1 d . . .
H22A H 0.1068 0.5619 0.2197 0.028 Uiso 1 1 calc R . .
H22B H 0.1796 0.5161 0.2875 0.028 Uiso 1 1 calc R . .
C23 C 0.0832(5) 0.5798(4) 0.3521(4) 0.0276(15) Uani 1 1 d . . .
H23A H 0.1262 0.6522 0.3643 0.033 Uiso 1 1 calc R . .
H23B H 0.0067 0.5754 0.3366 0.033 Uiso 1 1 calc R . .
C24 C 0.1066(6) 0.5400(6) 0.4384(4) 0.0431(19) Uani 1 1 d . . .
H24A H 0.0645 0.4683 0.4271 0.065 Uiso 1 1 calc R . .
H24B H 0.0876 0.5784 0.4881 0.065 Uiso 1 1 calc R . .
H24C H 0.1830 0.5474 0.4563 0.065 Uiso 1 1 calc R . .
C25 C -0.0356(4) 0.2444(4) 0.1394(4) 0.0184(12) Uani 1 1 d . . .
H25A H -0.0123 0.1962 0.1005 0.022 Uiso 1 1 calc R . .
H25B H -0.0378 0.2217 0.1982 0.022 Uiso 1 1 calc R . .
C26 C -0.1484(4) 0.2381(4) 0.0913(4) 0.0231(13) Uani 1 1 d . . .
H26A H -0.1723 0.2879 0.1274 0.028 Uiso 1 1 calc R . .
H26B H -0.1496 0.2540 0.0295 0.028 Uiso 1 1 calc R . .
C27 C -0.2232(5) 0.1318(4) 0.0820(4) 0.0228(13) Uani 1 1 d . . .
H27A H -0.1960 0.0826 0.0489 0.027 Uiso 1 1 calc R . .
H27B H -0.2226 0.1177 0.1443 0.027 Uiso 1 1 calc R . .
C28 C -0.3367(5) 0.1164(5) 0.0315(5) 0.0406(18) Uani 1 1 d . . .
H28A H -0.3662 0.1613 0.0663 0.061 Uiso 1 1 calc R . .
H28B H -0.3801 0.0458 0.0249 0.061 Uiso 1 1 calc R . .
H28C H -0.3378 0.1321 -0.0297 0.061 Uiso 1 1 calc R . .
C29 C 0.0511(4) 0.3938(4) 0.0753(4) 0.0171(12) Uani 1 1 d . . .
H29A H -0.0208 0.3987 0.0506 0.020 Uiso 1 1 calc R . .
H29B H 0.1018 0.4637 0.0945 0.020 Uiso 1 1 calc R . .
C30 C 0.0824(5) 0.3373(4) -0.0019(4) 0.0197(13) Uani 1 1 d . . .
H30A H 0.1564 0.3360 0.0202 0.024 Uiso 1 1 calc R . .
H30B H 0.0340 0.2665 -0.0206 0.024 Uiso 1 1 calc R . .
C31 C 0.0758(5) 0.3876(4) -0.0837(4) 0.0221(13) Uani 1 1 d . . .
H31A H 0.1210 0.4595 -0.0638 0.026 Uiso 1 1 calc R . .
H31B H 0.0010 0.3858 -0.1074 0.026 Uiso 1 1 calc R . .
C32 C 0.1127(5) 0.3355(5) -0.1615(4) 0.0260(14) Uani 1 1 d . . .
H32A H 0.1879 0.3399 -0.1392 0.039 Uiso 1 1 calc R . .
H32B H 0.1054 0.3691 -0.2138 0.039 Uiso 1 1 calc R . .
H32C H 0.0685 0.2642 -0.1812 0.039 Uiso 1 1 calc R . .
C33A C 0.4244(6) 0.5567(5) 0.8044(5) 0.016(2) Uani 0.785(18) 1 d PU A 1
C34A C 0.3849(6) 0.5713(5) 0.7212(6) 0.016(2) Uani 0.785(18) 1 d PU A 1
C33B C 0.434(3) 0.549(2) 0.742(2) 0.018(7) Uani 0.215(18) 1 d PU A 2
C34B C 0.370(2) 0.585(2) 0.777(2) 0.016(7) Uani 0.215(18) 1 d PU A 2
C35A C 0.1357(11) 0.9045(10) 0.2922(9) 0.009(4) Uani 0.389(19) 1 d PU B 1
C36A C 0.0817(11) 0.9629(11) 0.2521(10) 0.010(4) Uani 0.389(19) 1 d PU B 1
C35B C 0.1159(8) 0.9258(7) 0.2346(8) 0.019(3) Uani 0.611(19) 1 d PU B 2
C36B C 0.0935(8) 0.9506(7) 0.3116(8) 0.021(3) Uani 0.611(19) 1 d PU B 2
I1 I 0.54919(3) 0.49258(3) 0.83266(3) 0.02605(10) Uani 1 1 d . . .
I2 I 0.44089(3) 0.53181(3) 0.60463(3) 0.02950(11) Uani 1 1 d . . .
I3 I 0.26833(3) 0.64608(3) 0.69478(3) 0.02616(10) Uani 1 1 d . . .
I4 I 0.36190(3) 0.59110(3) 0.91823(3) 0.02052(9) Uani 1 1 d . . .
I5 I 0.14142(3) 0.89299(3) 0.43094(3) 0.01985(9) Uani 1 1 d . . .
I6 I 0.20021(3) 0.81677(3) 0.21039(3) 0.02866(11) Uani 1 1 d . . .
I7 I 0.07045(3) 0.98078(3) 0.11585(3) 0.02671(10) Uani 1 1 d . . .
I8 I -0.00235(3) 1.04767(3) 0.32536(3) 0.02574(10) Uani 1 1 d . . .
N1 N 0.6119(4) 0.8503(3) 0.2789(3) 0.0185(10) Uani 1 1 d . . .
N2 N 0.0487(4) 0.3483(3) 0.1602(3) 0.0161(10) Uani 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
Br1 0.0179(3) 0.0229(3) 0.0228(3) 0.0008(2) 0.0056(2) 0.0081(2)
Br2 0.0258(3) 0.0279(3) 0.0246(3) 0.0062(3) 0.0059(3) 0.0151(3)
C1 0.015(3) 0.024(3) 0.019(3) 0.002(3) 0.000(2) 0.002(2)
C2 0.022(3) 0.024(3) 0.030(4) 0.005(3) 0.010(3) 0.007(3)
C3 0.026(3) 0.026(3) 0.028(4) 0.004(3) 0.004(3) 0.009(3)
C4 0.032(4) 0.034(4) 0.030(4) 0.011(3) 0.014(3) 0.020(3)
C5 0.018(3) 0.020(3) 0.022(3) 0.003(3) 0.000(3) 0.004(2)
C6 0.024(3) 0.028(3) 0.019(3) 0.008(3) 0.003(3) 0.010(3)
C7 0.019(3) 0.028(3) 0.027(4) 0.003(3) 0.003(3) 0.004(3)
C8 0.021(3) 0.037(4) 0.038(4) 0.012(3) 0.006(3) 0.013(3)
C9 0.014(3) 0.033(4) 0.029(4) 0.014(3) 0.006(3) 0.004(3)
C10 0.033(4) 0.044(4) 0.031(4) 0.018(3) 0.014(3) 0.020(3)
C11 0.043(5) 0.114(8) 0.033(4) 0.030(5) 0.018(4) 0.032(5)
C12 0.060(6) 0.148(10) 0.057(6) 0.051(7) 0.034(5) 0.062(7)
C13 0.027(3) 0.021(3) 0.023(3) 0.002(3) 0.004(3) 0.010(3)
C14 0.019(3) 0.028(3) 0.027(3) 0.010(3) -0.001(3) 0.007(3)
C15 0.077(6) 0.036(5) 0.076(7) -0.013(4) -0.035(5) 0.040(5)
C16 0.056(5) 0.036(4) 0.063(6) 0.009(4) -0.005(4) 0.028(4)
C17 0.019(3) 0.022(3) 0.019(3) 0.007(2) 0.007(2) 0.009(2)
C18 0.017(3) 0.023(3) 0.016(3) 0.005(2) 0.005(2) 0.009(2)
C19 0.025(3) 0.028(3) 0.023(3) 0.008(3) 0.006(3) 0.016(3)
C20 0.023(3) 0.035(4) 0.027(4) 0.011(3) 0.003(3) 0.010(3)
C21 0.025(3) 0.018(3) 0.017(3) 0.004(2) 0.008(3) 0.012(2)
C22 0.034(4) 0.020(3) 0.017(3) 0.002(2) 0.005(3) 0.010(3)
C23 0.027(4) 0.017(3) 0.031(4) -0.006(3) 0.000(3) 0.006(3)
C24 0.065(5) 0.045(4) 0.019(4) 0.000(3) 0.009(3) 0.021(4)
C25 0.019(3) 0.013(3) 0.022(3) 0.004(2) 0.005(2) 0.004(2)
C26 0.021(3) 0.023(3) 0.023(3) 0.007(3) -0.002(3) 0.007(3)
C27 0.024(3) 0.020(3) 0.021(3) 0.004(3) 0.005(3) 0.002(3)
C28 0.031(4) 0.028(4) 0.051(5) 0.010(3) 0.000(3) -0.001(3)
C29 0.021(3) 0.013(3) 0.018(3) 0.006(2) 0.005(2) 0.004(2)
C30 0.022(3) 0.021(3) 0.020(3) 0.008(2) 0.007(3) 0.011(2)
C31 0.031(4) 0.021(3) 0.014(3) 0.002(2) 0.005(3) 0.010(3)
C32 0.027(4) 0.031(4) 0.022(3) 0.005(3) 0.007(3) 0.011(3)
C33A 0.015(3) 0.016(3) 0.017(4) 0.003(3) 0.006(3) 0.007(3)
C34A 0.015(3) 0.016(3) 0.018(4) 0.002(3) 0.006(3) 0.006(3)
C33B 0.018(8) 0.018(8) 0.018(8) 0.004(5) 0.004(5) 0.004(5)
C34B 0.018(8) 0.016(8) 0.014(8) 0.005(5) 0.001(5) 0.006(5)
C35A 0.011(5) 0.010(5) 0.005(5) -0.001(4) 0.000(4) 0.004(4)
C36A 0.009(5) 0.013(5) 0.009(6) 0.001(4) 0.002(4) 0.006(4)
C35B 0.022(4) 0.015(4) 0.022(4) 0.007(3) 0.004(3) 0.008(3)
C36B 0.019(4) 0.019(4) 0.024(5) 0.006(3) 0.002(3) 0.005(3)
I1 0.0175(2) 0.0193(2) 0.0419(3) 0.00767(18) 0.00562(18) 0.00717(16)
I2 0.0284(2) 0.0376(2) 0.0223(2) 0.00348(18) 0.01140(18) 0.00789(19)
I3 0.0261(2) 0.0248(2) 0.0269(2) 0.00851(17) -0.00045(17) 0.01040(17)
I4 0.0202(2) 0.0226(2) 0.0202(2) 0.00514(16) 0.00645(16) 0.00782(16)
I5 0.0212(2) 0.0216(2) 0.0173(2) 0.00486(15) 0.00230(15) 0.00898(16)
I6 0.0220(2) 0.0212(2) 0.0418(3) -0.00299(18) 0.01572(19) 0.00476(17)
I7 0.0357(2) 0.0253(2) 0.0186(2) 0.00872(17) 0.00497(18) 0.00807(18)
I8 0.0176(2) 0.01459(19) 0.0464(3) 0.00629(18) 0.00969(18) 0.00604(15)
N1 0.015(2) 0.021(3) 0.021(3) 0.006(2) 0.003(2) 0.007(2)
N2 0.019(3) 0.014(2) 0.018(3) 0.006(2) 0.006(2) 0.0067(19)
_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 C2 1.512(8) . ?
C1 N1 1.513(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.522(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.510(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.515(7) . ?
C5 C6 1.517(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.521(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.504(9) . ?
C9 N1 1.520(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.552(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.486(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.506(7) . ?
C13 C14 1.523(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.503(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.504(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.510(7) . ?
C17 N2 1.526(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.528(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.515(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N2 1.520(7) . ?
C21 C22 1.520(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.530(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.503(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.519(8) . ?
C25 N2 1.523(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.518(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.506(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.514(8) . ?
C29 N2 1.516(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.511(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.535(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33A C34A 1.335(13) . ?
C33A I4 2.114(7) . ?
C33A I1 2.115(7) . ?
C34A I2 2.113(8) . ?
C34A I3 2.124(8) . ?
C33B C34B 1.27(5) . ?
C33B I2 2.09(3) . ?
C33B I1 2.25(3) . ?
C34B I3 2.10(3) . ?
C34B I4 2.16(3) . ?
C35A C36A 1.37(2) . ?
C35A I6 2.096(14) . ?
C35A I5 2.117(14) . ?
C36A I7 2.094(15) . ?
C36A I8 2.190(17) . ?
C35B C36B 1.286(18) . ?
C35B I7 2.104(10) . ?
C35B I6 2.178(12) . ?
C36B I8 2.137(11) . ?
C36B I5 2.140(11) . ?
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 C1 N1 116.7(5) . . ?
C2 C1 H1A 108.1 . . ?
N1 C1 H1A 108.1 . . ?
C2 C1 H1B 108.1 . . ?
N1 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
C1 C2 C3 110.2(5) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 113.3(5) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 116.9(5) . . ?
N1 C5 H5A 108.1 . . ?
C6 C5 H5A 108.1 . . ?
N1 C5 H5B 108.1 . . ?
C6 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C5 C6 C7 109.1(5) . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C6 112.9(5) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 116.7(5) . . ?
C10 C9 H9A 108.1 . . ?
N1 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
N1 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 108.5(6) . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 C10 111.1(8) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 115.3(5) . . ?
N1 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N1 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 109.4(5) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C16 115.6(6) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N2 117.1(4) . . ?
C18 C17 H17A 108.0 . . ?
N2 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
N2 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 C19 109.1(5) . . ?
C17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 C18 113.2(5) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 115.8(5) . . ?
N2 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
N2 C21 H21B 108.3 . . ?
C22 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 C23 110.6(5) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 113.7(5) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N2 116.1(4) . . ?
C26 C25 H25A 108.3 . . ?
N2 C25 H25A 108.3 . . ?
C26 C25 H25B 108.3 . . ?
N2 C25 H25B 108.3 . . ?
H25A C25 H25B 107.4 . . ?
C27 C26 C25 109.2(5) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C28 C27 C26 113.3(5) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N2 116.2(4) . . ?
C30 C29 H29A 108.2 . . ?
N2 C29 H29A 108.2 . . ?
C30 C29 H29B 108.2 . . ?
N2 C29 H29B 108.2 . . ?
H29A C29 H29B 107.4 . . ?
C31 C30 C29 110.6(5) . . ?
C31 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C30 C31 C32 112.0(5) . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34A C33A I4 122.1(6) . . ?
C34A C33A I1 123.4(6) . . ?
I4 C33A I1 114.5(4) . . ?
C33A C34A I2 123.1(6) . . ?
C33A C34A I3 123.5(6) . . ?
I2 C34A I3 113.3(4) . . ?
C34B C33B I2 126(3) . . ?
C34B C33B I1 119(2) . . ?
I2 C33B I1 114.9(15) . . ?
C33B C34B I3 120(2) . . ?
C33B C34B I4 123(2) . . ?
I3 C34B I4 117.3(15) . . ?
C36A C35A I6 118.7(11) . . ?
C36A C35A I5 120.3(11) . . ?
I6 C35A I5 120.8(7) . . ?
C35A C36A I7 124.0(12) . . ?
C35A C36A I8 122.9(11) . . ?
I7 C36A I8 113.1(8) . . ?
C36B C35B I7 124.2(9) . . ?
C36B C35B I6 123.7(8) . . ?
I7 C35B I6 112.0(5) . . ?
C35B C36B I8 121.1(9) . . ?
C35B C36B I5 123.0(9) . . ?
I8 C36B I5 115.8(5) . . ?
C33A I1 C33B 25.5(8) . . ?
C33B I2 C34A 23.0(8) . . ?
C34B I3 C34A 24.8(8) . . ?
C33A I4 C34B 26.6(8) . . ?
C35A I5 C36B 27.8(4) . . ?
C35A I6 C35B 26.2(4) . . ?
C36A I7 C35B 22.9(4) . . ?
C36B I8 C36A 24.8(4) . . ?
C13 N1 C1 111.0(4) . . ?
C13 N1 C5 106.5(4) . . ?
C1 N1 C5 111.4(4) . . ?
C13 N1 C9 111.6(4) . . ?
C1 N1 C9 105.7(4) . . ?
C5 N1 C9 110.8(4) . . ?
C29 N2 C21 109.4(4) . . ?
C29 N2 C25 112.2(4) . . ?
C21 N2 C25 108.8(4) . . ?
C29 N2 C17 108.7(4) . . ?
C21 N2 C17 110.5(4) . . ?
C25 N2 C17 107.3(4) . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         2.074
_refine_diff_density_min         -1.831
_refine_diff_density_rms         0.161