# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Anthony Chesman'
_publ_contact_author_email       anthony.chesman@monash.edu
_publ_author_name                A.-V.Mudring

data_AC2P782.CIF
_database_code_depnum_ccdc_archive 'CCDC 790887'
#TrackingRef 'AC2P782.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Tri(tetrabutylammonium) hexakis(dicyanonitrosomethanido)cerium(III)
;
_chemical_name_common            (N4444)3[Ce(dcnm)6]
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 Ce N18 O6, 3(C16 H36 N)'
_chemical_formula_sum            'C66 H108 Ce N21 O6'
_chemical_formula_weight         1431.85

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'
Ce Ce -0.2486 2.6331 '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           trigonal
_symmetry_space_group_name_H-M   R32

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.4269(5)
_cell_length_b                   17.4269(5)
_cell_length_c                   22.3789(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5885.9(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    19769
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      29.00

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2271
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8315
_exptl_absorpt_correction_T_max  0.8829
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            19769
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3269
_reflns_number_gt                3263
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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^)+(0.2000P)^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     SHELXL
_refine_ls_extinction_coef       none
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_number_reflns         3269
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0158
_refine_ls_R_factor_gt           0.0158
_refine_ls_wR_factor_ref         0.0413
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   0.720
_refine_ls_restrained_S_all      0.720
_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
N4 N 0.61680(8) 1.0000 1.0000 0.0179(3) Uani 1 2 d S . .
C11 C 0.60188(8) 1.06792(8) 0.96776(5) 0.0204(2) Uani 1 1 d . . .
H11A H 0.5574 1.0372 0.9359 0.024 Uiso 1 1 calc R . .
H11B H 0.6580 1.1111 0.9481 0.024 Uiso 1 1 calc R . .
C12 C 0.57093(10) 1.11874(9) 1.00645(5) 0.0244(3) Uani 1 1 d . . .
H12A H 0.6149 1.1504 1.0384 0.029 Uiso 1 1 calc R . .
H12B H 0.5139 1.0768 1.0256 0.029 Uiso 1 1 calc R . .
C13 C 0.55938(10) 1.18537(9) 0.96888(7) 0.0294(3) Uani 1 1 d . . .
H13A H 0.6149 1.2228 0.9465 0.035 Uiso 1 1 calc R . .
H13B H 0.5496 1.2246 0.9959 0.035 Uiso 1 1 calc R . .
C14 C 0.48273(12) 1.14279(12) 0.92459(7) 0.0402(4) Uani 1 1 d . . .
H14A H 0.4295 1.0976 0.9451 0.060 Uiso 1 1 calc R . .
H14B H 0.4981 1.1152 0.8921 0.060 Uiso 1 1 calc R . .
H14C H 0.4713 1.1883 0.9081 0.060 Uiso 1 1 calc R . .
C31 C 0.64516(8) 0.95729(8) 0.95194(5) 0.0195(2) Uani 1 1 d . . .
H31A H 0.6014 0.9376 0.9190 0.023 Uiso 1 1 calc R . .
H31B H 0.7028 1.0032 0.9355 0.023 Uiso 1 1 calc R . .
C32 C 0.65444(8) 0.87899(9) 0.97151(6) 0.0215(2) Uani 1 1 d . . .
H32A H 0.5962 0.8293 0.9840 0.026 Uiso 1 1 calc R . .
H32B H 0.6957 0.8959 1.0058 0.026 Uiso 1 1 calc R . .
C33 C 0.69025(8) 0.85120(14) 0.91854(5) 0.0250(3) Uani 1 1 d . . .
H33A H 0.6562 0.8480 0.8823 0.030 Uiso 1 1 calc R . .
H33B H 0.7529 0.8969 0.9117 0.030 Uiso 1 1 calc R . .
C34 C 0.68464(10) 0.76249(9) 0.92802(7) 0.0325(3) Uani 1 1 d . . .
H34A H 0.6236 0.7179 0.9382 0.049 Uiso 1 1 calc R . .
H34B H 0.7242 0.7673 0.9607 0.049 Uiso 1 1 calc R . .
H34C H 0.7024 0.7449 0.8913 0.049 Uiso 1 1 calc R . .
Ce1 Ce 1.0000 1.0000 1.0000 0.01355(4) Uani 1 6 d S . .
O1 O 0.93225(8) 0.84704(5) 0.95614(3) 0.0216(2) Uani 1 1 d . . .
N1 N 0.91525(7) 0.88657(6) 0.91395(4) 0.0174(2) Uani 1 1 d . . .
N2 N 0.87166(9) 0.69221(8) 0.84354(6) 0.0357(3) Uani 1 1 d . . .
N3 N 0.85768(7) 0.92780(14) 0.77865(4) 0.0328(2) Uani 1 1 d . . .
C1 C 0.88862(8) 0.84574(8) 0.86205(5) 0.0182(2) Uani 1 1 d . . .
C2 C 0.87921(14) 0.76021(7) 0.85160(5) 0.0233(2) Uani 1 1 d . . .
C3 C 0.87153(8) 0.89101(8) 0.81528(6) 0.0220(3) 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
N4 0.0189(5) 0.0215(7) 0.0141(8) -0.0034(5) -0.0017(3) 0.0107(3)
C11 0.0235(6) 0.0229(6) 0.0162(6) -0.0013(5) -0.0033(5) 0.0127(5)
C12 0.0288(9) 0.0285(5) 0.0209(5) -0.0079(4) -0.0069(5) 0.0180(5)
C13 0.0357(7) 0.0273(6) 0.0303(8) -0.0033(6) -0.0018(6) 0.0196(6)
C14 0.0549(10) 0.0514(10) 0.0324(9) -0.0057(7) -0.0124(7) 0.0400(9)
C31 0.0231(6) 0.0250(6) 0.0119(6) -0.0032(4) 0.0005(4) 0.0132(5)
C32 0.0231(6) 0.0272(6) 0.0174(6) -0.0023(5) -0.0016(5) 0.0151(5)
C33 0.0238(5) 0.0288(9) 0.0243(5) -0.0009(7) 0.0044(4) 0.0145(7)
C34 0.0335(7) 0.0319(7) 0.0382(9) -0.0021(6) 0.0027(6) 0.0208(6)
Ce1 0.01581(5) 0.01581(5) 0.00903(7) 0.000 0.000 0.00791(2)
O1 0.0287(6) 0.0193(3) 0.0154(4) 0.0000(3) -0.0042(4) 0.0109(4)
N1 0.0170(4) 0.0179(4) 0.0151(5) 0.0007(4) 0.0008(4) 0.0071(4)
N2 0.0488(7) 0.0302(6) 0.0300(7) -0.0083(5) -0.0022(5) 0.0212(5)
N3 0.0368(5) 0.0321(9) 0.0256(5) 0.0010(9) -0.0097(4) 0.0143(9)
C1 0.0177(5) 0.0189(5) 0.0160(6) -0.0017(4) -0.0007(4) 0.0077(4)
C2 0.0254(9) 0.0246(5) 0.0160(5) -0.0041(4) 0.0000(9) 0.0096(9)
C3 0.0201(6) 0.0237(6) 0.0187(6) -0.0044(5) -0.0039(5) 0.0083(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
N4 C11 1.5156(14) 4_677 ?
N4 C11 1.5156(14) . ?
N4 C31 1.5241(14) . ?
N4 C31 1.5241(14) 4_677 ?
C11 C12 1.5174(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5262(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C31 C32 1.5167(18) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.5270(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.514(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
Ce1 O1 2.5132(8) . ?
Ce1 O1 2.5132(8) 6_557 ?
Ce1 O1 2.5132(8) 4_677 ?
Ce1 O1 2.5132(8) 3_675 ?
Ce1 O1 2.5132(8) 5_767 ?
Ce1 O1 2.5132(8) 2_765 ?
Ce1 N1 2.6225(10) . ?
Ce1 N1 2.6224(10) 3_675 ?
Ce1 N1 2.6224(10) 4_677 ?
Ce1 N1 2.6224(10) 2_765 ?
Ce1 N1 2.6224(10) 6_557 ?
Ce1 N1 2.6224(10) 5_767 ?
O1 N1 1.2876(14) . ?
N1 C1 1.3193(15) . ?
N2 C2 1.139(2) . ?
N3 C3 1.138(2) . ?
C1 C3 1.4288(18) . ?
C1 C2 1.4347(18) . ?

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
C11 N4 C11 111.61(13) 4_677 . ?
C11 N4 C31 111.68(7) 4_677 . ?
C11 N4 C31 105.64(7) . . ?
C11 N4 C31 105.64(7) 4_677 4_677 ?
C11 N4 C31 111.68(7) . 4_677 ?
C31 N4 C31 110.71(13) . 4_677 ?
N4 C11 C12 115.72(10) . . ?
N4 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N4 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 110.50(10) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 113.86(12) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C32 C31 N4 116.24(9) . . ?
C32 C31 H31A 108.2 . . ?
N4 C31 H31A 108.2 . . ?
C32 C31 H31B 108.2 . . ?
N4 C31 H31B 108.2 . . ?
H31A C31 H31B 107.4 . . ?
C31 C32 C33 107.79(12) . . ?
C31 C32 H32A 110.1 . . ?
C33 C32 H32A 110.1 . . ?
C31 C32 H32B 110.1 . . ?
C33 C32 H32B 110.1 . . ?
H32A C32 H32B 108.5 . . ?
C34 C33 C32 112.77(12) . . ?
C34 C33 H33A 109.0 . . ?
C32 C33 H33A 109.0 . . ?
C34 C33 H33B 109.0 . . ?
C32 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O1 Ce1 O1 80.14(6) . 6_557 ?
O1 Ce1 O1 173.06(7) . 4_677 ?
O1 Ce1 O1 105.734(19) 6_557 4_677 ?
O1 Ce1 O1 105.734(19) . 3_675 ?
O1 Ce1 O1 68.66(6) 6_557 3_675 ?
O1 Ce1 O1 80.14(6) 4_677 3_675 ?
O1 Ce1 O1 68.66(6) . 5_767 ?
O1 Ce1 O1 105.734(19) 6_557 5_767 ?
O1 Ce1 O1 105.734(19) 4_677 5_767 ?
O1 Ce1 O1 173.06(7) 3_675 5_767 ?
O1 Ce1 O1 105.734(19) . 2_765 ?
O1 Ce1 O1 173.06(6) 6_557 2_765 ?
O1 Ce1 O1 68.66(6) 4_677 2_765 ?
O1 Ce1 O1 105.734(19) 3_675 2_765 ?
O1 Ce1 O1 80.14(6) 5_767 2_765 ?
O1 Ce1 N1 28.94(3) . . ?
O1 Ce1 N1 82.38(3) 6_557 . ?
O1 Ce1 N1 153.86(3) 4_677 . ?
O1 Ce1 N1 79.92(3) 3_675 . ?
O1 Ce1 N1 95.47(3) 5_767 . ?
O1 Ce1 N1 100.94(3) 2_765 . ?
O1 Ce1 N1 100.94(3) . 3_675 ?
O1 Ce1 N1 95.47(3) 6_557 3_675 ?
O1 Ce1 N1 82.38(3) 4_677 3_675 ?
O1 Ce1 N1 28.94(3) 3_675 3_675 ?
O1 Ce1 N1 153.86(3) 5_767 3_675 ?
O1 Ce1 N1 79.92(3) 2_765 3_675 ?
N1 Ce1 N1 72.01(3) . 3_675 ?
O1 Ce1 N1 153.86(3) . 4_677 ?
O1 Ce1 N1 79.92(3) 6_557 4_677 ?
O1 Ce1 N1 28.94(3) 4_677 4_677 ?
O1 Ce1 N1 82.38(3) 3_675 4_677 ?
O1 Ce1 N1 100.94(3) 5_767 4_677 ?
O1 Ce1 N1 95.47(3) 2_765 4_677 ?
N1 Ce1 N1 158.52(5) . 4_677 ?
N1 Ce1 N1 97.63(4) 3_675 4_677 ?
O1 Ce1 N1 79.92(3) . 2_765 ?
O1 Ce1 N1 153.86(3) 6_557 2_765 ?
O1 Ce1 N1 95.47(3) 4_677 2_765 ?
O1 Ce1 N1 100.94(3) 3_675 2_765 ?
O1 Ce1 N1 82.38(3) 5_767 2_765 ?
O1 Ce1 N1 28.94(3) 2_765 2_765 ?
N1 Ce1 N1 72.01(3) . 2_765 ?
N1 Ce1 N1 72.01(3) 3_675 2_765 ?
N1 Ce1 N1 123.65(5) 4_677 2_765 ?
O1 Ce1 N1 82.38(3) . 6_557 ?
O1 Ce1 N1 28.94(3) 6_557 6_557 ?
O1 Ce1 N1 100.94(3) 4_677 6_557 ?
O1 Ce1 N1 95.47(3) 3_675 6_557 ?
O1 Ce1 N1 79.92(3) 5_767 6_557 ?
O1 Ce1 N1 153.86(3) 2_765 6_557 ?
N1 Ce1 N1 97.63(4) . 6_557 ?
N1 Ce1 N1 123.65(4) 3_675 6_557 ?
N1 Ce1 N1 72.01(3) 4_677 6_557 ?
N1 Ce1 N1 158.52(5) 2_765 6_557 ?
O1 Ce1 N1 95.47(3) . 5_767 ?
O1 Ce1 N1 100.94(3) 6_557 5_767 ?
O1 Ce1 N1 79.92(3) 4_677 5_767 ?
O1 Ce1 N1 153.86(3) 3_675 5_767 ?
O1 Ce1 N1 28.94(3) 5_767 5_767 ?
O1 Ce1 N1 82.38(3) 2_765 5_767 ?
N1 Ce1 N1 123.65(4) . 5_767 ?
N1 Ce1 N1 158.52(5) 3_675 5_767 ?
N1 Ce1 N1 72.01(3) 4_677 5_767 ?
N1 Ce1 N1 97.63(4) 2_765 5_767 ?
N1 Ce1 N1 72.01(3) 6_557 5_767 ?
N1 O1 Ce1 80.24(6) . . ?
O1 N1 C1 118.03(10) . . ?
O1 N1 Ce1 70.82(5) . . ?
C1 N1 Ce1 165.17(8) . . ?
N1 C1 C3 117.47(11) . . ?
N1 C1 C2 122.04(11) . . ?
C3 C1 C2 120.47(11) . . ?
N2 C2 C1 179.73(18) . . ?
N3 C3 C1 178.96(16) . . ?

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
C11 N4 C11 C12 57.23(9) 4_677 . . . ?
C31 N4 C11 C12 178.80(11) . . . . ?
C31 N4 C11 C12 -60.77(14) 4_677 . . . ?
N4 C11 C12 C13 179.41(11) . . . . ?
C11 C12 C13 C14 68.35(16) . . . . ?
C11 N4 C31 C32 -51.84(14) 4_677 . . . ?
C11 N4 C31 C32 -173.36(10) . . . . ?
C31 N4 C31 C32 65.58(9) 4_677 . . . ?
N4 C31 C32 C33 -175.49(10) . . . . ?
C31 C32 C33 C34 -168.09(11) . . . . ?
O1 Ce1 O1 N1 92.06(8) 6_557 . . . ?
O1 Ce1 O1 N1 -119.70(7) 4_677 . . . ?
O1 Ce1 O1 N1 27.70(7) 3_675 . . . ?
O1 Ce1 O1 N1 -156.63(10) 5_767 . . . ?
O1 Ce1 O1 N1 -84.15(6) 2_765 . . . ?
N1 Ce1 O1 N1 -1.66(8) 3_675 . . . ?
N1 Ce1 O1 N1 132.84(10) 4_677 . . . ?
N1 Ce1 O1 N1 -70.94(8) 2_765 . . . ?
N1 Ce1 O1 N1 121.27(7) 6_557 . . . ?
N1 Ce1 O1 N1 -167.75(6) 5_767 . . . ?
Ce1 O1 N1 C1 166.98(10) . . . . ?
O1 Ce1 N1 O1 -83.40(10) 6_557 . . . ?
O1 Ce1 N1 O1 166.22(13) 4_677 . . . ?
O1 Ce1 N1 O1 -152.97(6) 3_675 . . . ?
O1 Ce1 N1 O1 21.79(10) 5_767 . . . ?
O1 Ce1 N1 O1 102.78(5) 2_765 . . . ?
N1 Ce1 N1 O1 178.29(8) 3_675 . . . ?
N1 Ce1 N1 O1 -118.05(7) 4_677 . . . ?
N1 Ce1 N1 O1 101.93(9) 2_765 . . . ?
N1 Ce1 N1 O1 -58.74(7) 6_557 . . . ?
N1 Ce1 N1 O1 14.70(7) 5_767 . . . ?
O1 Ce1 N1 C1 -129.0(4) . . . . ?
O1 Ce1 N1 C1 147.6(3) 6_557 . . . ?
O1 Ce1 N1 C1 37.2(4) 4_677 . . . ?
O1 Ce1 N1 C1 78.0(3) 3_675 . . . ?
O1 Ce1 N1 C1 -107.2(3) 5_767 . . . ?
O1 Ce1 N1 C1 -26.2(3) 2_765 . . . ?
N1 Ce1 N1 C1 49.3(3) 3_675 . . . ?
N1 Ce1 N1 C1 112.9(3) 4_677 . . . ?
N1 Ce1 N1 C1 -27.1(3) 2_765 . . . ?
N1 Ce1 N1 C1 172.2(3) 6_557 . . . ?
N1 Ce1 N1 C1 -114.3(3) 5_767 . . . ?
O1 N1 C1 C3 -178.88(11) . . . . ?
Ce1 N1 C1 C3 -55.1(4) . . . . ?
O1 N1 C1 C2 -0.6(2) . . . . ?
Ce1 N1 C1 C2 123.1(3) . . . . ?
N1 C1 C2 N2 29(54) . . . . ?
C3 C1 C2 N2 -152(100) . . . . ?
N1 C1 C3 N3 -25(9) . . . . ?
C2 C1 C3 N3 157(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.036


data_abscor
_database_code_depnum_ccdc_archive 'CCDC 813884'
#TrackingRef '4333_web_deposit_cif_file_0_Anja-VerenaMudring_1298029270.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H108 N21 O6 Sm'
_chemical_formula_weight         1442.08

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'
Sm Sm -0.1638 3.4418 '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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.5311(11)
_cell_length_b                   17.5311(11)
_cell_length_c                   22.2630(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5925.6(7)
_cell_formula_units_Z            3
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2283
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7950
_exptl_absorpt_correction_T_max  0.8561
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18914
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.07
_reflns_number_total             3180
_reflns_number_gt                3129
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0427P)^2^+0.2834P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(11)
_refine_ls_number_reflns         3180
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_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
N4 N -0.61686(16) 0.0000 0.0000 0.0262(6) Uani 1 2 d S . .
C11 C -0.60185(16) -0.06714(16) 0.03267(11) 0.0294(5) Uani 1 1 d . . .
H11A H -0.6576 -0.1099 0.0526 0.035 Uiso 1 1 calc R . .
H11B H -0.5576 -0.0363 0.0646 0.035 Uiso 1 1 calc R . .
C12 C -0.5712(2) -0.11785(17) -0.00572(11) 0.0356(8) Uani 1 1 d . . .
H12A H -0.5144 -0.0762 -0.0250 0.043 Uiso 1 1 calc R . .
H12B H -0.6148 -0.1494 -0.0379 0.043 Uiso 1 1 calc R . .
C13 C -0.5597(2) -0.1840(2) 0.03207(15) 0.0442(6) Uani 1 1 d . . .
H13A H -0.5494 -0.2227 0.0049 0.053 Uiso 1 1 calc R . .
H13B H -0.6150 -0.2215 0.0543 0.053 Uiso 1 1 calc R . .
C14 C -0.4840(3) -0.1414(3) 0.07687(17) 0.0607(10) Uani 1 1 d . . .
H14A H -0.4307 -0.0973 0.0562 0.091 Uiso 1 1 calc R . .
H14B H -0.4735 -0.1866 0.0943 0.091 Uiso 1 1 calc R . .
H14C H -0.4992 -0.1129 0.1088 0.091 Uiso 1 1 calc R . .
C31 C -0.64442(16) -0.95680(16) -0.95191(10) 0.0281(5) Uani 1 1 d . . .
H31A H -0.7010 -1.0024 -0.9345 0.034 Uiso 1 1 calc R . .
H31B H -0.6000 -0.9359 -0.9194 0.034 Uiso 1 1 calc R . .
C32 C -0.65517(17) -0.88021(17) -0.97214(11) 0.0313(5) Uani 1 1 d . . .
H32A H -0.6970 -0.8983 -1.0062 0.038 Uiso 1 1 calc R . .
H32B H -0.5978 -0.8307 -0.9855 0.038 Uiso 1 1 calc R . .
C33 C -0.69008(16) -0.8518(3) -0.91906(11) 0.0355(6) Uani 1 1 d . . .
H33A H -0.7521 -0.8973 -0.9116 0.043 Uiso 1 1 calc R . .
H33B H -0.6556 -0.8477 -0.8828 0.043 Uiso 1 1 calc R . .
C34 C -0.6851(2) -0.7643(2) -0.92937(16) 0.0481(7) Uani 1 1 d . . .
H34A H -0.6241 -0.7193 -0.9381 0.072 Uiso 1 1 calc R . .
H34B H -0.7052 -0.7476 -0.8933 0.072 Uiso 1 1 calc R . .
H34C H -0.7227 -0.7692 -0.9634 0.072 Uiso 1 1 calc R . .
CE1 Sm 0.0000 0.0000 0.0000 0.02238(8) Uani 1 6 d S . .
O1 O -0.9332(2) -0.85140(10) -0.95777(7) 0.0318(4) Uani 1 1 d . . .
N1 N -0.91600(13) -0.88941(13) -0.91506(9) 0.0271(4) Uani 1 1 d . . .
N2 N -0.8727(2) -0.69536(17) -0.84548(12) 0.0505(7) Uani 1 1 d . . .
N3 N -0.85777(14) -0.9275(3) -0.77817(9) 0.0469(5) Uani 1 1 d . . .
C1 C -0.88948(15) -0.84806(15) -0.86307(10) 0.0261(4) Uani 1 1 d . . .
C2 C -0.8798(3) -0.76270(13) -0.85321(9) 0.0335(4) Uani 1 1 d . . .
C3 C -0.87184(16) -0.89159(16) -0.81549(11) 0.0322(5) 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
N4 0.0281(10) 0.0309(14) 0.0204(13) -0.0032(10) -0.0016(5) 0.0155(7)
C11 0.0321(11) 0.0337(11) 0.0246(11) -0.0032(9) -0.0057(9) 0.0180(10)
C12 0.041(2) 0.0397(11) 0.0314(11) -0.0109(9) -0.0108(10) 0.0241(11)
C13 0.0544(15) 0.0407(14) 0.0465(16) -0.0048(13) -0.0025(13) 0.0306(13)
C14 0.083(3) 0.082(3) 0.0461(19) -0.0081(17) -0.0171(17) 0.063(2)
C31 0.0310(11) 0.0347(12) 0.0196(11) -0.0036(9) -0.0008(8) 0.0172(10)
C32 0.0319(12) 0.0401(13) 0.0259(12) -0.0041(10) -0.0028(9) 0.0211(11)
C33 0.0338(10) 0.040(2) 0.0353(11) -0.0026(14) 0.0064(8) 0.0206(14)
C34 0.0472(16) 0.0473(16) 0.059(2) -0.0037(14) 0.0036(14) 0.0306(14)
CE1 0.02552(9) 0.02552(9) 0.01608(11) 0.000 0.000 0.01276(4)
O1 0.0420(14) 0.0303(6) 0.0232(6) 0.0001(5) -0.0052(9) 0.0181(10)
N1 0.0239(8) 0.0274(9) 0.0285(10) 0.0035(8) 0.0038(7) 0.0118(7)
N2 0.0680(17) 0.0409(13) 0.0453(14) -0.0098(11) -0.0031(12) 0.0291(12)
N3 0.0522(11) 0.047(2) 0.0391(10) 0.002(2) -0.0148(9) 0.023(2)
C1 0.0250(10) 0.0271(10) 0.0230(11) -0.0034(9) -0.0029(8) 0.0106(9)
C2 0.037(2) 0.0347(10) 0.0266(9) -0.0056(7) 0.000(2) 0.0167(19)
C3 0.0296(11) 0.0335(12) 0.0284(12) -0.0046(10) -0.0054(9) 0.0118(10)

_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
N4 C11 1.514(3) 4 ?
N4 C11 1.514(3) . ?
N4 C31 1.523(3) 1_566 ?
N4 C31 1.523(3) 4_444 ?
C11 C12 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C31 C32 1.515(4) . ?
C31 N4 1.523(3) 1_544 ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.524(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.510(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
CE1 O1 2.4476(15) 4_544 ?
CE1 O1 2.4476(15) 1_666 ?
CE1 O1 2.4476(15) 2_456 ?
CE1 O1 2.4476(15) 6_664 ?
CE1 O1 2.4476(15) 3_546 ?
CE1 O1 2.4476(15) 5_454 ?
CE1 N1 2.578(2) 1_666 ?
CE1 N1 2.578(2) 4_544 ?
CE1 N1 2.578(2) 5_454 ?
CE1 N1 2.578(2) 6_664 ?
CE1 N1 2.578(2) 2_456 ?
CE1 N1 2.578(2) 3_546 ?
O1 N1 1.280(3) . ?
O1 CE1 2.4476(15) 1_444 ?
N1 C1 1.321(3) . ?
N1 CE1 2.578(2) 1_444 ?
N2 C2 1.137(4) . ?
N3 C3 1.141(5) . ?
C1 C3 1.427(4) . ?
C1 C2 1.436(4) . ?

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
C11 N4 C11 111.6(3) 4 . ?
C11 N4 C31 111.47(13) 4 1_566 ?
C11 N4 C31 105.70(13) . 1_566 ?
C11 N4 C31 105.70(13) 4 4_444 ?
C11 N4 C31 111.47(13) . 4_444 ?
C31 N4 C31 111.1(2) 1_566 4_444 ?
N4 C11 C12 115.87(19) . . ?
N4 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
N4 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 110.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 113.7(3) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C32 C31 N4 116.28(18) . 1_544 ?
C32 C31 H31A 108.2 . . ?
N4 C31 H31A 108.2 1_544 . ?
C32 C31 H31B 108.2 . . ?
N4 C31 H31B 108.2 1_544 . ?
H31A C31 H31B 107.4 . . ?
C31 C32 C33 107.9(2) . . ?
C31 C32 H32A 110.1 . . ?
C33 C32 H32A 110.1 . . ?
C31 C32 H32B 110.1 . . ?
C33 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
C34 C33 C32 112.7(3) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O1 CE1 O1 173.88(16) 4_544 1_666 ?
O1 CE1 O1 68.83(13) 4_544 2_456 ?
O1 CE1 O1 106.18(4) 1_666 2_456 ?
O1 CE1 O1 106.18(4) 4_544 6_664 ?
O1 CE1 O1 79.01(14) 1_666 6_664 ?
O1 CE1 O1 173.88(16) 2_456 6_664 ?
O1 CE1 O1 79.01(14) 4_544 3_546 ?
O1 CE1 O1 106.18(4) 1_666 3_546 ?
O1 CE1 O1 106.18(4) 2_456 3_546 ?
O1 CE1 O1 68.83(13) 6_664 3_546 ?
O1 CE1 O1 106.18(4) 4_544 5_454 ?
O1 CE1 O1 68.83(13) 1_666 5_454 ?
O1 CE1 O1 79.01(14) 2_456 5_454 ?
O1 CE1 O1 106.18(4) 6_664 5_454 ?
O1 CE1 O1 173.88(16) 3_546 5_454 ?
O1 CE1 N1 153.17(6) 4_544 1_666 ?
O1 CE1 N1 29.37(7) 1_666 1_666 ?
O1 CE1 N1 101.49(6) 2_456 1_666 ?
O1 CE1 N1 81.41(7) 6_664 1_666 ?
O1 CE1 N1 80.06(7) 3_546 1_666 ?
O1 CE1 N1 95.86(7) 5_454 1_666 ?
O1 CE1 N1 29.37(7) 4_544 4_544 ?
O1 CE1 N1 153.17(6) 1_666 4_544 ?
O1 CE1 N1 95.86(7) 2_456 4_544 ?
O1 CE1 N1 80.06(7) 6_664 4_544 ?
O1 CE1 N1 81.41(7) 3_546 4_544 ?
O1 CE1 N1 101.49(6) 5_454 4_544 ?
N1 CE1 N1 157.49(9) 1_666 4_544 ?
O1 CE1 N1 80.06(7) 4_544 5_454 ?
O1 CE1 N1 95.86(7) 1_666 5_454 ?
O1 CE1 N1 81.41(7) 2_456 5_454 ?
O1 CE1 N1 101.49(6) 6_664 5_454 ?
O1 CE1 N1 153.17(6) 3_546 5_454 ?
O1 CE1 N1 29.37(7) 5_454 5_454 ?
N1 CE1 N1 124.40(9) 1_666 5_454 ?
N1 CE1 N1 72.13(7) 4_544 5_454 ?
O1 CE1 N1 101.49(6) 4_544 6_664 ?
O1 CE1 N1 81.41(7) 1_666 6_664 ?
O1 CE1 N1 153.17(6) 2_456 6_664 ?
O1 CE1 N1 29.37(7) 6_664 6_664 ?
O1 CE1 N1 95.86(7) 3_546 6_664 ?
O1 CE1 N1 80.06(7) 5_454 6_664 ?
N1 CE1 N1 97.17(9) 1_666 6_664 ?
N1 CE1 N1 72.13(7) 4_544 6_664 ?
N1 CE1 N1 72.13(7) 5_454 6_664 ?
O1 CE1 N1 95.86(7) 4_544 2_456 ?
O1 CE1 N1 80.06(7) 1_666 2_456 ?
O1 CE1 N1 29.37(7) 2_456 2_456 ?
O1 CE1 N1 153.17(6) 6_664 2_456 ?
O1 CE1 N1 101.49(6) 3_546 2_456 ?
O1 CE1 N1 81.41(7) 5_454 2_456 ?
N1 CE1 N1 72.13(7) 1_666 2_456 ?
N1 CE1 N1 124.40(9) 4_544 2_456 ?
N1 CE1 N1 97.17(9) 5_454 2_456 ?
N1 CE1 N1 157.49(9) 6_664 2_456 ?
O1 CE1 N1 81.41(7) 4_544 3_546 ?
O1 CE1 N1 101.49(6) 1_666 3_546 ?
O1 CE1 N1 80.06(7) 2_456 3_546 ?
O1 CE1 N1 95.86(7) 6_664 3_546 ?
O1 CE1 N1 29.37(7) 3_546 3_546 ?
O1 CE1 N1 153.17(6) 5_454 3_546 ?
N1 CE1 N1 72.13(7) 1_666 3_546 ?
N1 CE1 N1 97.17(9) 4_544 3_546 ?
N1 CE1 N1 157.49(9) 5_454 3_546 ?
N1 CE1 N1 124.40(9) 6_664 3_546 ?
N1 CE1 N1 72.13(7) 2_456 3_546 ?
N1 O1 CE1 80.99(12) . 1_444 ?
O1 N1 C1 118.4(2) . . ?
O1 N1 CE1 69.64(11) . 1_444 ?
C1 N1 CE1 165.33(17) . 1_444 ?
N1 C1 C3 117.9(2) . . ?
N1 C1 C2 122.1(2) . . ?
C3 C1 C2 120.0(2) . . ?
N2 C2 C1 179.6(5) . . ?
N3 C3 C1 178.8(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
C11 N4 C11 C12 -57.11(18) 4 . . . ?
C31 N4 C11 C12 -178.4(2) 1_566 . . . ?
C31 N4 C11 C12 60.8(3) 4_444 . . . ?
N4 C11 C12 C13 -179.2(2) . . . . ?
C11 C12 C13 C14 -67.9(4) . . . . ?
N4 C31 C32 C33 175.3(2) 1_544 . . . ?
C31 C32 C33 C34 167.7(2) . . . . ?
CE1 O1 N1 C1 -166.5(2) 1_444 . . . ?
O1 N1 C1 C3 179.1(2) . . . . ?
CE1 N1 C1 C3 59.0(7) 1_444 . . . ?
O1 N1 C1 C2 0.3(4) . . . . ?
CE1 N1 C1 C2 -119.8(6) 1_444 . . . ?
N1 C1 C2 N2 60(52) . . . . ?
C3 C1 C2 N2 -119(52) . . . . ?
N1 C1 C3 N3 14(14) . . . . ?
C2 C1 C3 N3 -168(100) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.057