# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#
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#  from this site to visualise CIF-encoded structures and 
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data_global

#============================================================================
data_i1103
#TrackingRef '16250_web_deposit_cif_file_0_Dr.ClemensBruhn_1355749992.i1103.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H72 Cl3 Li3 N12 O3'
_chemical_formula_sum            'C33 H72 Cl3 Li3 N12 O3'
_chemical_formula_weight         812.20

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'
Li Li -0.0003 0.0001 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

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                   23.776(3)
_cell_length_b                   13.2356(13)
_cell_length_c                   18.2673(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.025(6)
_cell_angle_gamma                90.00
_cell_volume                     4707.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8663
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      25.53

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1752
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 162 frames, detector distance = 135 mm
;

_diffrn_standards_decay_%        0
_diffrn_reflns_number            13441
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4142
_reflns_number_gt                2676
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0415P)^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         4142
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_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
C1 C 0.44230(9) -0.23554(12) 0.68031(13) 0.0376(4) Uani 1 1 d . . .
C2 C 0.5000 -0.18277(16) 0.7500 0.0341(6) Uani 1 2 d S . .
C3 C 0.43288(11) -0.35517(16) 0.77712(15) 0.0573(6) Uani 1 1 d . . .
H3A H 0.4464 -0.2955 0.8155 0.069 Uiso 1 1 calc R . .
H3B H 0.4695 -0.4059 0.8068 0.069 Uiso 1 1 calc R . .
H3C H 0.3905 -0.3835 0.7659 0.069 Uiso 1 1 calc R . .
C4 C 0.38642(12) -0.40316(15) 0.62306(17) 0.0672(7) Uani 1 1 d . . .
H4A H 0.3899 -0.3857 0.5737 0.081 Uiso 1 1 calc R . .
H4B H 0.3379 -0.4062 0.6011 0.081 Uiso 1 1 calc R . .
H4C H 0.4079 -0.4691 0.6476 0.081 Uiso 1 1 calc R . .
C5 C 0.43136(11) -0.12607(15) 0.56471(15) 0.0563(5) Uani 1 1 d . . .
H5C H 0.4117 -0.1401 0.5017 0.068 Uiso 1 1 calc R . .
H5B H 0.4813 -0.1349 0.6002 0.068 Uiso 1 1 calc R . .
H5A H 0.4206 -0.0565 0.5709 0.068 Uiso 1 1 calc R . .
C6 C 0.32757(10) -0.19900(18) 0.54417(16) 0.0667(6) Uani 1 1 d . . .
H6A H 0.3132 -0.2218 0.5821 0.080 Uiso 1 1 calc R . .
H6B H 0.3102 -0.2460 0.4941 0.080 Uiso 1 1 calc R . .
H6C H 0.3090 -0.1314 0.5210 0.080 Uiso 1 1 calc R . .
C7 C 0.31523(9) 0.16045(11) 0.69354(13) 0.0360(4) Uani 1 1 d . . .
C8 C 0.40875(9) 0.24633(13) 0.82865(14) 0.0406(4) Uani 1 1 d . . .
C9 C 0.38639(8) 0.17800(12) 0.75857(13) 0.0364(4) Uani 1 1 d . . .
C10 C 0.19615(9) 0.19219(15) 0.64882(15) 0.0519(5) Uani 1 1 d . . .
H10A H 0.1663 0.1328 0.6307 0.062 Uiso 1 1 calc R . .
H10B H 0.1911 0.2220 0.5962 0.062 Uiso 1 1 calc R . .
H10C H 0.1831 0.2420 0.6763 0.062 Uiso 1 1 calc R . .
C11 C 0.28479(11) 0.13630(16) 0.80113(15) 0.0527(5) Uani 1 1 d . . .
H11A H 0.2895 0.1983 0.8335 0.063 Uiso 1 1 calc R . .
H11B H 0.3282 0.0988 0.8345 0.063 Uiso 1 1 calc R . .
H11C H 0.2482 0.0944 0.7947 0.063 Uiso 1 1 calc R . .
C12 C 0.23923(12) 0.05907(17) 0.55740(16) 0.0656(6) Uani 1 1 d . . .
H12C H 0.2558 0.0109 0.5331 0.079 Uiso 1 1 calc R . .
H12B H 0.1967 0.0905 0.5082 0.079 Uiso 1 1 calc R . .
H12A H 0.2304 0.0235 0.5969 0.079 Uiso 1 1 calc R . .
C13 C 0.32720(12) 0.17092(18) 0.56914(16) 0.0622(6) Uani 1 1 d . . .
H13A H 0.3572 0.1167 0.5738 0.075 Uiso 1 1 calc R . .
H13B H 0.3549 0.2306 0.6015 0.075 Uiso 1 1 calc R . .
H13C H 0.2936 0.1882 0.5061 0.075 Uiso 1 1 calc R . .
C14 C 0.32685(12) 0.38348(14) 0.73725(18) 0.0645(7) Uani 1 1 d . . .
H14A H 0.2787 0.3715 0.7144 0.077 Uiso 1 1 calc R . .
H14B H 0.3352 0.3593 0.6936 0.077 Uiso 1 1 calc R . .
H14C H 0.3367 0.4560 0.7472 0.077 Uiso 1 1 calc R . .
C15 C 0.37198(14) 0.36991(17) 0.8957(2) 0.0775(7) Uani 1 1 d . . .
H15A H 0.3949 0.4358 0.9130 0.093 Uiso 1 1 calc R . .
H15B H 0.3969 0.3233 0.9464 0.093 Uiso 1 1 calc R . .
H15C H 0.3247 0.3777 0.8781 0.093 Uiso 1 1 calc R . .
C16 C 0.50376(12) 0.1374(2) 0.93985(17) 0.0766(7) Uani 1 1 d . . .
H16A H 0.5328 0.1245 0.9187 0.092 Uiso 1 1 calc R . .
H16B H 0.4682 0.0852 0.9166 0.092 Uiso 1 1 calc R . .
H16C H 0.5320 0.1361 1.0053 0.092 Uiso 1 1 calc R . .
C17 C 0.51627(13) 0.3232(2) 0.9536(2) 0.0934(9) Uani 1 1 d . . .
H17A H 0.4933 0.3847 0.9193 0.112 Uiso 1 1 calc R . .
H18B H 0.5591 0.3135 0.9582 0.112 Uiso 1 1 calc R . .
H18C H 0.5266 0.3296 1.0136 0.112 Uiso 1 1 calc R . .
Li1 Li 0.43131(15) -0.0125(2) 0.7500(2) 0.0440(7) Uani 1 1 d . . .
Li2 Li 0.5000 0.1984(3) 0.7500 0.0455(11) Uani 1 2 d S . .
N1 N 0.42142(8) -0.32648(11) 0.69286(11) 0.0474(4) Uani 1 1 d . . .
N2 N 0.40228(8) -0.19569(11) 0.59651(11) 0.0466(4) Uani 1 1 d . . .
N3 N 0.26767(7) 0.16195(11) 0.71341(11) 0.0411(4) Uani 1 1 d . . .
N4 N 0.29112(8) 0.13702(12) 0.60803(11) 0.0463(4) Uani 1 1 d . . .
N5 N 0.37105(8) 0.32978(11) 0.82078(12) 0.0518(4) Uani 1 1 d . . .
N6 N 0.47131(8) 0.23650(13) 0.90835(12) 0.0580(5) Uani 1 1 d . . .
O1 O 0.5000 -0.08021(11) 0.7500 0.0373(4) Uani 1 2 d S . .
O2 O 0.43266(6) 0.12785(8) 0.75066(9) 0.0410(3) Uani 1 1 d . . .
Cl1 Cl 0.35358(3) -0.09909(4) 0.76144(5) 0.0791(2) Uani 1 1 d . . .
Cl2 Cl 0.5000 0.37013(6) 0.7500 0.0920(4) Uani 1 2 d S . .

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 0.0349(10) 0.0334(8) 0.0489(13) -0.0013(8) 0.0267(10) -0.0003(7)
C2 0.0331(13) 0.0295(11) 0.0430(17) 0.000 0.0238(13) 0.000
C3 0.0628(13) 0.0511(11) 0.0705(16) -0.0014(11) 0.0455(13) -0.0145(10)
C4 0.0764(16) 0.0479(11) 0.0759(18) -0.0170(12) 0.0428(15) -0.0219(11)
C5 0.0605(14) 0.0549(11) 0.0474(14) 0.0068(10) 0.0274(12) -0.0010(10)
C6 0.0389(12) 0.0744(15) 0.0645(17) -0.0036(12) 0.0166(11) 0.0017(10)
C7 0.0364(10) 0.0303(8) 0.0471(13) -0.0010(8) 0.0274(9) 0.0005(7)
C8 0.0306(10) 0.0422(9) 0.0529(13) -0.0040(9) 0.0262(10) -0.0022(7)
C9 0.0342(10) 0.0309(8) 0.0505(13) 0.0017(8) 0.0280(9) 0.0018(7)
C10 0.0359(11) 0.0602(12) 0.0608(15) -0.0010(10) 0.0284(11) 0.0019(9)
C11 0.0472(12) 0.0646(11) 0.0573(15) -0.0006(11) 0.0365(11) -0.0070(10)
C12 0.0599(14) 0.0647(13) 0.0629(17) -0.0234(12) 0.0298(13) -0.0054(11)
C13 0.0604(14) 0.0812(14) 0.0587(15) 0.0131(12) 0.0422(13) 0.0166(11)
C14 0.0586(14) 0.0340(10) 0.098(2) 0.0007(11) 0.0427(14) 0.0054(9)
C15 0.0934(19) 0.0601(13) 0.105(2) -0.0260(14) 0.0721(18) -0.0045(12)
C16 0.0526(14) 0.117(2) 0.0614(17) 0.0242(15) 0.0332(13) 0.0363(14)
C17 0.0534(15) 0.138(2) 0.076(2) -0.0459(18) 0.0294(14) -0.0332(16)
Li1 0.0415(17) 0.0348(14) 0.062(2) 0.0028(14) 0.0335(17) 0.0027(12)
Li2 0.040(2) 0.037(2) 0.066(3) 0.000 0.035(2) 0.000
N1 0.0512(10) 0.0393(8) 0.0523(11) -0.0068(7) 0.0300(9) -0.0148(7)
N2 0.0356(9) 0.0480(9) 0.0450(11) 0.0019(8) 0.0167(8) -0.0027(7)
N3 0.0308(8) 0.0501(8) 0.0448(10) -0.0012(7) 0.0231(8) -0.0011(6)
N4 0.0402(9) 0.0552(9) 0.0471(11) -0.0053(8) 0.0272(8) -0.0009(7)
N5 0.0514(10) 0.0386(8) 0.0702(13) -0.0102(8) 0.0376(10) 0.0011(7)
N6 0.0375(10) 0.0769(12) 0.0527(12) -0.0105(9) 0.0218(9) -0.0003(9)
O1 0.0364(9) 0.0277(8) 0.0499(12) 0.000 0.0260(9) 0.000
O2 0.0356(7) 0.0349(6) 0.0622(9) -0.0005(6) 0.0338(7) 0.0034(5)
Cl1 0.0823(4) 0.0506(3) 0.1436(7) 0.0163(3) 0.0878(5) 0.0039(3)
Cl2 0.1328(9) 0.0360(4) 0.1662(11) 0.000 0.1203(9) 0.000

_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 N2 1.362(2) . ?
C1 N1 1.370(2) . ?
C1 C2 1.409(2) . ?
C2 O1 1.357(3) . ?
C2 C1 1.409(2) 2_656 ?
C2 Li1 2.783(3) 2_656 ?
C2 Li1 2.783(3) . ?
C3 N1 1.451(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.460(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.458(2) . ?
C5 H5C 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5A 0.9800 . ?
C6 N2 1.457(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N4 1.355(2) . ?
C7 N3 1.372(2) . ?
C7 C9 1.421(2) . ?
C8 N6 1.365(2) . ?
C8 N5 1.377(2) . ?
C8 C9 1.399(3) . ?
C9 O2 1.3617(18) . ?
C9 Li1 2.777(3) . ?
C10 N3 1.463(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N3 1.449(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N4 1.460(3) . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12A 0.9800 . ?
C13 N4 1.463(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N5 1.448(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N5 1.456(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N6 1.462(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N6 1.459(3) . ?
C17 H17A 0.9800 . ?
C17 H18B 0.9800 . ?
C17 H18C 0.9800 . ?
Li1 O2 1.857(3) . ?
Li1 O1 1.863(3) . ?
Li1 Cl1 2.284(3) . ?
Li1 Li2 3.234(4) . ?
Li1 Li1 3.266(5) 2_656 ?
Li2 O2 1.859(2) . ?
Li2 O2 1.859(2) 2_656 ?
Li2 Cl2 2.273(4) . ?
Li2 Li1 3.234(4) 2_656 ?
O1 Li1 1.863(3) 2_656 ?

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
N2 C1 N1 116.21(16) . . ?
N2 C1 C2 120.88(15) . . ?
N1 C1 C2 122.85(17) . . ?
O1 C2 C1 119.71(10) . 2_656 ?
O1 C2 C1 119.71(10) . . ?
C1 C2 C1 120.6(2) 2_656 . ?
O1 C2 Li1 35.92(6) . 2_656 ?
C1 C2 Li1 97.72(10) 2_656 2_656 ?
C1 C2 Li1 131.94(12) . 2_656 ?
O1 C2 Li1 35.93(6) . . ?
C1 C2 Li1 131.94(12) 2_656 . ?
C1 C2 Li1 97.72(10) . . ?
Li1 C2 Li1 71.85(13) 2_656 . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5C 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
N2 C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 N3 116.14(15) . . ?
N4 C7 C9 120.92(14) . . ?
N3 C7 C9 122.89(17) . . ?
N6 C8 N5 115.68(17) . . ?
N6 C8 C9 121.56(15) . . ?
N5 C8 C9 122.69(17) . . ?
O2 C9 C8 120.42(15) . . ?
O2 C9 C7 118.57(15) . . ?
C8 C9 C7 121.00(14) . . ?
O2 C9 Li1 36.03(9) . . ?
C8 C9 Li1 132.98(14) . . ?
C7 C9 Li1 96.68(12) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12C 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
N4 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C16 H16A 109.5 . . ?
N6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H18B 109.5 . . ?
H17A C17 H18B 109.5 . . ?
N6 C17 H18C 109.5 . . ?
H17A C17 H18C 109.5 . . ?
H18B C17 H18C 109.5 . . ?
O2 Li1 O1 117.99(15) . . ?
O2 Li1 Cl1 120.88(14) . . ?
O1 Li1 Cl1 120.92(14) . . ?
O2 Li1 C9 25.54(6) . . ?
O1 Li1 C9 143.35(14) . . ?
Cl1 Li1 C9 95.33(10) . . ?
O2 Li1 C2 143.30(14) . . ?
O1 Li1 C2 25.31(6) . . ?
Cl1 Li1 C2 95.69(10) . . ?
C9 Li1 C2 168.44(12) . . ?
O2 Li1 Li2 29.56(7) . . ?
O1 Li1 Li2 88.43(11) . . ?
Cl1 Li1 Li2 150.27(12) . . ?
C9 Li1 Li2 55.04(7) . . ?
C2 Li1 Li2 113.74(10) . . ?
O2 Li1 Li1 89.22(9) . 2_656 ?
O1 Li1 Li1 28.76(9) . 2_656 ?
Cl1 Li1 Li1 149.50(7) . 2_656 ?
C9 Li1 Li1 114.64(6) . 2_656 ?
C2 Li1 Li1 54.07(6) . 2_656 ?
Li2 Li1 Li1 59.67(6) . 2_656 ?
O2 Li2 O2 119.7(2) . 2_656 ?
O2 Li2 Cl2 120.15(11) . . ?
O2 Li2 Cl2 120.15(11) 2_656 . ?
O2 Li2 Li1 90.18(15) . 2_656 ?
O2 Li2 Li1 29.52(9) 2_656 2_656 ?
Cl2 Li2 Li1 149.67(6) . 2_656 ?
O2 Li2 Li1 29.52(9) . . ?
O2 Li2 Li1 90.19(15) 2_656 . ?
Cl2 Li2 Li1 149.67(6) . . ?
Li1 Li2 Li1 60.66(12) 2_656 . ?
C1 N1 C3 122.80(16) . . ?
C1 N1 C4 122.97(17) . . ?
C3 N1 C4 114.23(16) . . ?
C1 N2 C6 121.89(16) . . ?
C1 N2 C5 120.50(15) . . ?
C6 N2 C5 115.84(17) . . ?
C7 N3 C11 122.55(15) . . ?
C7 N3 C10 122.92(16) . . ?
C11 N3 C10 114.50(14) . . ?
C7 N4 C12 122.45(16) . . ?
C7 N4 C13 120.75(16) . . ?
C12 N4 C13 115.25(18) . . ?
C8 N5 C14 122.61(17) . . ?
C8 N5 C15 122.5(2) . . ?
C14 N5 C15 114.93(18) . . ?
C8 N6 C17 121.7(2) . . ?
C8 N6 C16 120.74(18) . . ?
C17 N6 C16 115.7(2) . . ?
C2 O1 Li1 118.77(9) . 2_656 ?
C2 O1 Li1 118.77(9) . . ?
Li1 O1 Li1 122.47(19) 2_656 . ?
C9 O2 Li1 118.43(13) . . ?
C9 O2 Li2 120.46(14) . . ?
Li1 O2 Li2 120.92(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.030


_database_code_depnum_ccdc_archive 'CCDC 916147'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global

data_i1086
#TrackingRef 'web_deposit_cif_file_0_Dr.ClemensBruhn_1366187287.i1086.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H49 N4 O, 0.5(C6 H6), Cl H, Cl '
_chemical_formula_sum            'C42 H53 Cl2 N4 O'
_chemical_formula_weight         700.78

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'
Cl Cl 0.1484 0.1585 '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   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   11.9689(10)
_cell_length_b                   18.788(2)
_cell_length_c                   18.0000(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.455(7)
_cell_angle_gamma                90.00
_cell_volume                     3967.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8633
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      25.52

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1500
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 140 frames, detector distance = 135 mm
;

_diffrn_standards_decay_%        0
_diffrn_reflns_number            19717
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.1019
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.28
_reflns_number_total             7083
_reflns_number_gt                3753
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0000P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7083
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.350
_refine_ls_restrained_S_all      1.350
_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 0.8130(2) 0.81089(14) 0.56090(17) 0.0287(7) Uani 1 1 d . . .
C2 C 0.9116(3) 0.84868(14) 0.59542(19) 0.0353(8) Uani 1 1 d . . .
C3 C 1.0226(2) 0.82444(13) 0.62625(16) 0.0275(7) Uani 1 1 d . . .
C4 C 0.6892(3) 0.86809(14) 0.63574(17) 0.0376(8) Uani 1 1 d . . .
H4A H 0.7667 0.8735 0.6685 0.045 Uiso 1 1 calc R . .
C5 C 0.6221(3) 0.81867(17) 0.67897(18) 0.0530(9) Uani 1 1 d . . .
H5A H 0.5412 0.8196 0.6547 0.064 Uiso 1 1 calc R . .
H5B H 0.6311 0.8349 0.7316 0.064 Uiso 1 1 calc R . .
H5C H 0.6513 0.7700 0.6782 0.064 Uiso 1 1 calc R . .
C6 C 0.6362(3) 0.94273(16) 0.6280(2) 0.0585(10) Uani 1 1 d . . .
H6C H 0.6846 0.9749 0.6053 0.070 Uiso 1 1 calc R . .
H6B H 0.6299 0.9605 0.6781 0.070 Uiso 1 1 calc R . .
H6A H 0.5602 0.9405 0.5954 0.070 Uiso 1 1 calc R . .
C7 C 0.6156(2) 0.83316(16) 0.49483(19) 0.0393(8) Uani 1 1 d . . .
H7A H 0.6422 0.7991 0.4593 0.047 Uiso 1 1 calc R . .
C8 C 0.4999(3) 0.80479(17) 0.5052(2) 0.0598(10) Uani 1 1 d . . .
H8A H 0.4486 0.8009 0.4556 0.072 Uiso 1 1 calc R . .
H8B H 0.4670 0.8375 0.5374 0.072 Uiso 1 1 calc R . .
H8C H 0.5099 0.7578 0.5292 0.072 Uiso 1 1 calc R . .
C9 C 0.6011(3) 0.90526(16) 0.4526(2) 0.0643(11) Uani 1 1 d . . .
H9C H 0.6756 0.9284 0.4575 0.077 Uiso 1 1 calc R . .
H9B H 0.5500 0.9359 0.4747 0.077 Uiso 1 1 calc R . .
H9A H 0.5685 0.8972 0.3989 0.077 Uiso 1 1 calc R . .
C10 C 0.7357(3) 0.69453(15) 0.5094(2) 0.0431(9) Uani 1 1 d . . .
C11 C 0.6830(3) 0.66885(16) 0.4398(2) 0.0592(11) Uani 1 1 d . . .
H11A H 0.7063 0.6856 0.3954 0.071 Uiso 1 1 calc R . .
C12 C 0.5951(3) 0.61814(19) 0.4330(3) 0.0768(14) Uani 1 1 d . . .
H12A H 0.5565 0.6016 0.3848 0.092 Uiso 1 1 calc R . .
C13 C 0.5668(4) 0.59277(19) 0.5014(3) 0.0833(16) Uani 1 1 d . . .
H13A H 0.5084 0.5581 0.4989 0.100 Uiso 1 1 calc R . .
C14 C 0.6213(3) 0.61709(19) 0.5702(3) 0.0747(14) Uani 1 1 d . . .
H14A H 0.6004 0.5991 0.6148 0.090 Uiso 1 1 calc R . .
C15 C 0.7076(3) 0.66810(15) 0.5763(2) 0.0519(10) Uani 1 1 d . . .
H15A H 0.7462 0.6845 0.6245 0.062 Uiso 1 1 calc R . .
C16 C 0.8974(3) 0.74949(15) 0.46269(18) 0.0404(8) Uani 1 1 d . . .
C17 C 0.9474(3) 0.68630(15) 0.4469(2) 0.0494(10) Uani 1 1 d . . .
H17A H 0.9323 0.6433 0.4710 0.059 Uiso 1 1 calc R . .
C18 C 1.0203(3) 0.68650(18) 0.3953(2) 0.0638(12) Uani 1 1 d . . .
H18A H 1.0537 0.6431 0.3835 0.077 Uiso 1 1 calc R . .
C19 C 1.0445(3) 0.7489(2) 0.3611(2) 0.0601(10) Uani 1 1 d . . .
H19A H 1.0966 0.7486 0.3275 0.072 Uiso 1 1 calc R . .
C20 C 0.9928(3) 0.81167(18) 0.37587(19) 0.0515(10) Uani 1 1 d . . .
H20A H 1.0090 0.8546 0.3523 0.062 Uiso 1 1 calc R . .
C21 C 0.9173(3) 0.81199(15) 0.42511(18) 0.0423(8) Uani 1 1 d . . .
H21A H 0.8790 0.8547 0.4334 0.051 Uiso 1 1 calc R . .
C22 C 1.1231(3) 0.91609(14) 0.56904(18) 0.0383(8) Uani 1 1 d . . .
H22A H 1.0493 0.9106 0.5321 0.046 Uiso 1 1 calc R . .
C23 C 1.2166(3) 0.89705(16) 0.5246(2) 0.0573(11) Uani 1 1 d . . .
H23A H 1.2890 0.9185 0.5495 0.069 Uiso 1 1 calc R . .
H23B H 1.1952 0.9154 0.4727 0.069 Uiso 1 1 calc R . .
H23C H 1.2250 0.8452 0.5231 0.069 Uiso 1 1 calc R . .
C24 C 1.1308(3) 0.99481(14) 0.59032(19) 0.0490(9) Uani 1 1 d . . .
H24C H 1.0694 1.0069 0.6169 0.059 Uiso 1 1 calc R . .
H24B H 1.1234 1.0237 0.5443 0.059 Uiso 1 1 calc R . .
H24A H 1.2046 1.0044 0.6235 0.059 Uiso 1 1 calc R . .
C25 C 1.2067(3) 0.86370(15) 0.70333(19) 0.0393(8) Uani 1 1 d . . .
H25A H 1.1886 0.8211 0.7321 0.047 Uiso 1 1 calc R . .
C26 C 1.2003(3) 0.92795(16) 0.7549(2) 0.0629(11) Uani 1 1 d . . .
H26A H 1.2339 0.9696 0.7351 0.076 Uiso 1 1 calc R . .
H26B H 1.2423 0.9174 0.8062 0.076 Uiso 1 1 calc R . .
H26C H 1.1204 0.9378 0.7565 0.076 Uiso 1 1 calc R . .
C27 C 1.3269(3) 0.85271(18) 0.6916(2) 0.0667(12) Uani 1 1 d . . .
H27A H 1.3778 0.8449 0.7407 0.080 Uiso 1 1 calc R . .
H27B H 1.3517 0.8950 0.6673 0.080 Uiso 1 1 calc R . .
H27C H 1.3292 0.8111 0.6591 0.080 Uiso 1 1 calc R . .
C28 C 1.1393(3) 0.71434(15) 0.6494(2) 0.0481(10) Uani 1 1 d . . .
C29 C 1.1739(3) 0.71231(15) 0.5797(2) 0.0454(9) Uani 1 1 d . . .
H29A H 1.1318 0.7372 0.5373 0.054 Uiso 1 1 calc R . .
C30 C 1.2701(3) 0.67375(18) 0.5729(3) 0.0672(12) Uani 1 1 d . . .
H30A H 1.2943 0.6728 0.5257 0.081 Uiso 1 1 calc R . .
C31 C 1.3319(3) 0.6363(2) 0.6347(3) 0.0733(13) Uani 1 1 d . . .
H31A H 1.3978 0.6100 0.6298 0.088 Uiso 1 1 calc R . .
C32 C 1.2957(3) 0.63801(18) 0.7028(3) 0.0724(13) Uani 1 1 d . . .
H32A H 1.3362 0.6118 0.7447 0.087 Uiso 1 1 calc R . .
C33 C 1.2010(3) 0.67749(16) 0.7110(2) 0.0526(10) Uani 1 1 d . . .
H33A H 1.1783 0.6793 0.7586 0.063 Uiso 1 1 calc R . .
C34 C 0.9670(3) 0.72757(14) 0.70543(19) 0.0406(8) Uani 1 1 d . . .
C35 C 0.9396(3) 0.65504(15) 0.7015(2) 0.0500(9) Uani 1 1 d . . .
H35A H 0.9664 0.6251 0.6663 0.060 Uiso 1 1 calc R . .
C36 C 0.8728(3) 0.62699(19) 0.7496(2) 0.0688(12) Uani 1 1 d . . .
H36A H 0.8541 0.5778 0.7471 0.083 Uiso 1 1 calc R . .
C37 C 0.8333(3) 0.6708(2) 0.8012(2) 0.0701(12) Uani 1 1 d . . .
H37A H 0.7868 0.6516 0.8334 0.084 Uiso 1 1 calc R . .
C38 C 0.8618(3) 0.74308(19) 0.8057(2) 0.0612(11) Uani 1 1 d . . .
H38A H 0.8353 0.7730 0.8411 0.073 Uiso 1 1 calc R . .
C39 C 0.9293(3) 0.77085(16) 0.75805(19) 0.0508(10) Uani 1 1 d . . .
H39A H 0.9497 0.8198 0.7615 0.061 Uiso 1 1 calc R . .
C40 C 0.9525(6) 0.5063(2) 0.5625(4) 0.097(2) Uani 1 1 d . . .
H40A H 0.9189 0.5118 0.6058 0.116 Uiso 1 1 calc R . .
C41 C 0.8849(5) 0.4906(2) 0.4948(5) 0.110(2) Uani 1 1 d . . .
H41A H 0.8056 0.4830 0.4918 0.133 Uiso 1 1 calc R . .
C42 C 0.9303(6) 0.4853(2) 0.4298(3) 0.0890(15) Uani 1 1 d . . .
H42A H 0.8830 0.4763 0.3817 0.107 Uiso 1 1 calc R . .
Cl1 Cl 0.78264(11) 0.93141(6) 0.84890(7) 0.0932(4) Uani 1 1 d . . .
H2 H 0.873(3) 0.9690(17) 0.816(2) 0.112 Uiso 1 1 d . . .
Cl2 Cl 0.91551(10) 1.01320(5) 0.73732(7) 0.0851(4) Uani 1 1 d . . .
N1 N 0.7070(2) 0.83458(12) 0.56314(15) 0.0375(7) Uani 1 1 d . . .
N2 N 0.8216(2) 0.75053(12) 0.51650(14) 0.0377(7) Uani 1 1 d . . .
N3 N 1.1166(2) 0.86598(11) 0.63164(14) 0.0349(6) Uani 1 1 d . . .
N4 N 1.0376(2) 0.75472(12) 0.65526(14) 0.0367(6) Uani 1 1 d . . .
O1 O 0.89354(19) 0.92286(9) 0.59190(12) 0.0392(6) Uani 1 1 d . . .
H1 H 0.9123 0.9403 0.6356 0.047 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 0.0302(16) 0.0305(15) 0.0262(18) 0.0101(15) 0.0077(14) 0.0010(14)
C2 0.0442(19) 0.0237(15) 0.045(2) 0.0065(15) 0.0248(17) 0.0042(14)
C3 0.0306(16) 0.0286(16) 0.0238(18) -0.0001(14) 0.0063(14) 0.0006(14)
C4 0.0312(17) 0.0501(19) 0.031(2) 0.0004(16) 0.0049(15) 0.0040(15)
C5 0.049(2) 0.079(2) 0.034(2) 0.004(2) 0.0140(18) 0.002(2)
C6 0.059(2) 0.055(2) 0.063(3) -0.005(2) 0.017(2) 0.016(2)
C7 0.0351(18) 0.0393(17) 0.040(2) 0.0049(16) -0.0013(17) 0.0011(15)
C8 0.050(2) 0.052(2) 0.081(3) 0.007(2) 0.019(2) -0.0038(18)
C9 0.068(3) 0.053(2) 0.074(3) 0.023(2) 0.019(2) 0.008(2)
C10 0.045(2) 0.0263(16) 0.060(3) -0.0020(18) 0.016(2) -0.0022(15)
C11 0.065(2) 0.0386(19) 0.078(3) -0.011(2) 0.024(2) -0.0151(19)
C12 0.070(3) 0.050(2) 0.111(4) -0.026(3) 0.019(3) -0.018(2)
C13 0.071(3) 0.036(2) 0.145(5) 0.010(3) 0.026(4) -0.013(2)
C14 0.063(3) 0.051(2) 0.117(4) 0.021(3) 0.034(3) -0.007(2)
C15 0.051(2) 0.0388(19) 0.069(3) 0.0158(19) 0.020(2) 0.0029(17)
C16 0.0456(19) 0.0328(16) 0.048(2) -0.0057(17) 0.0216(18) -0.0036(16)
C17 0.061(2) 0.0300(17) 0.064(3) -0.0057(18) 0.028(2) 0.0031(17)
C18 0.076(3) 0.046(2) 0.078(3) -0.019(2) 0.037(2) 0.007(2)
C19 0.062(2) 0.077(2) 0.047(3) -0.021(2) 0.026(2) -0.012(2)
C20 0.068(2) 0.054(2) 0.037(2) -0.0075(19) 0.021(2) -0.012(2)
C21 0.053(2) 0.0340(17) 0.041(2) 0.0003(16) 0.0111(18) 0.0005(16)
C22 0.0428(19) 0.0341(16) 0.039(2) 0.0040(16) 0.0095(17) -0.0014(15)
C23 0.060(2) 0.051(2) 0.068(3) 0.008(2) 0.031(2) 0.0008(19)
C24 0.063(2) 0.0375(18) 0.047(2) 0.0063(18) 0.0122(19) -0.0074(17)
C25 0.0397(19) 0.0358(17) 0.036(2) 0.0028(16) -0.0076(16) -0.0036(15)
C26 0.086(3) 0.052(2) 0.050(3) -0.003(2) 0.011(2) -0.005(2)
C27 0.043(2) 0.068(2) 0.087(3) 0.002(2) 0.008(2) -0.002(2)
C28 0.045(2) 0.0273(16) 0.077(3) 0.0008(18) 0.023(2) 0.0047(16)
C29 0.044(2) 0.0376(18) 0.054(3) -0.0063(17) 0.0084(19) 0.0007(16)
C30 0.060(2) 0.056(2) 0.094(4) -0.016(2) 0.037(3) 0.003(2)
C31 0.043(2) 0.061(3) 0.110(4) -0.016(3) 0.000(3) 0.015(2)
C32 0.054(2) 0.042(2) 0.115(4) 0.010(2) 0.003(3) 0.0127(19)
C33 0.050(2) 0.0409(19) 0.058(3) 0.0034(19) -0.0093(19) 0.0092(18)
C34 0.0427(19) 0.0304(17) 0.050(2) 0.0098(16) 0.0132(18) -0.0009(15)
C35 0.058(2) 0.0348(18) 0.055(3) 0.0077(18) 0.005(2) -0.0040(17)
C36 0.076(3) 0.047(2) 0.083(3) 0.023(2) 0.017(3) -0.016(2)
C37 0.067(3) 0.076(3) 0.071(3) 0.040(3) 0.024(2) -0.003(2)
C38 0.067(2) 0.072(2) 0.049(3) 0.020(2) 0.022(2) 0.012(2)
C39 0.063(2) 0.0390(18) 0.058(3) 0.0137(18) 0.029(2) 0.0059(17)
C40 0.159(6) 0.033(2) 0.114(5) -0.026(3) 0.064(5) -0.025(3)
C41 0.118(5) 0.029(2) 0.204(7) -0.020(4) 0.080(6) -0.010(3)
C42 0.120(5) 0.045(2) 0.096(5) -0.003(3) 0.006(4) -0.008(3)
Cl1 0.1111(9) 0.0788(7) 0.0922(10) -0.0114(7) 0.0263(8) -0.0048(7)
Cl2 0.0872(8) 0.0847(7) 0.0948(9) -0.0436(7) 0.0459(7) -0.0177(7)
N1 0.0379(15) 0.0332(14) 0.0449(19) 0.0032(13) 0.0167(14) 0.0024(12)
N2 0.0445(15) 0.0292(12) 0.0439(18) -0.0034(13) 0.0196(14) -0.0058(13)
N3 0.0363(15) 0.0308(13) 0.0377(18) 0.0035(13) 0.0073(13) -0.0015(12)
N4 0.0397(15) 0.0278(13) 0.0447(18) 0.0065(13) 0.0137(14) 0.0039(12)
O1 0.0490(14) 0.0257(10) 0.0459(15) -0.0012(10) 0.0164(13) 0.0020(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
C1 N1 1.353(3) . ?
C1 N2 1.403(3) . ?
C1 C2 1.411(4) . ?
C2 O1 1.410(3) . ?
C2 C3 1.409(4) . ?
C3 N3 1.357(3) . ?
C3 N4 1.408(3) . ?
C4 N1 1.503(3) . ?
C4 C6 1.534(4) . ?
C4 C5 1.537(4) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6C 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6A 0.9800 . ?
C7 N1 1.475(4) . ?
C7 C8 1.529(4) . ?
C7 C9 1.546(4) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9C 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9A 0.9800 . ?
C10 C11 1.373(5) . ?
C10 C15 1.405(4) . ?
C10 N2 1.459(3) . ?
C11 C12 1.406(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.424(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.359(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.397(5) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C21 1.399(4) . ?
C16 C17 1.384(4) . ?
C16 N2 1.452(3) . ?
C17 C18 1.396(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.383(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.386(4) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 N3 1.482(3) . ?
C22 C24 1.526(4) . ?
C22 C23 1.542(4) . ?
C22 H22A 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24A 0.9800 . ?
C25 N3 1.509(4) . ?
C25 C27 1.509(4) . ?
C25 C26 1.535(4) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.388(5) . ?
C28 C29 1.397(4) . ?
C28 N4 1.456(3) . ?
C29 C30 1.387(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.397(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.380(5) . ?
C31 H31A 0.9500 . ?
C32 C33 1.387(4) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 C39 1.390(4) . ?
C34 C35 1.400(4) . ?
C34 N4 1.447(3) . ?
C35 C36 1.392(4) . ?
C35 H35A 0.9500 . ?
C36 C37 1.393(5) . ?
C36 H36A 0.9500 . ?
C37 C38 1.398(5) . ?
C37 H37A 0.9500 . ?
C38 C39 1.391(4) . ?
C38 H38A 0.9500 . ?
C39 H39A 0.9500 . ?
C40 C41 1.354(8) . ?
C40 C42 1.391(6) 3_766 ?
C40 H40A 0.9500 . ?
C41 C42 1.389(6) . ?
C41 H41A 0.9500 . ?
C42 C40 1.391(6) 3_766 ?
C42 H42A 0.9500 . ?
Cl1 H2 1.51(4) . ?
Cl2 H2 1.81(4) . ?
O1 H1 0.8400 . ?

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
N1 C1 N2 117.3(3) . . ?
N1 C1 C2 121.9(3) . . ?
N2 C1 C2 120.5(2) . . ?
O1 C2 C3 117.5(3) . . ?
O1 C2 C1 111.7(3) . . ?
C3 C2 C1 130.6(2) . . ?
N3 C3 C2 123.1(2) . . ?
N3 C3 N4 117.7(2) . . ?
C2 C3 N4 119.2(2) . . ?
N1 C4 C6 115.5(3) . . ?
N1 C4 C5 111.4(2) . . ?
C6 C4 C5 110.5(2) . . ?
N1 C4 H4A 106.2 . . ?
C6 C4 H4A 106.2 . . ?
C5 C4 H4A 106.2 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6C 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
C4 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
N1 C7 C8 116.4(3) . . ?
N1 C7 C9 112.7(3) . . ?
C8 C7 C9 110.5(3) . . ?
N1 C7 H7A 105.4 . . ?
C8 C7 H7A 105.4 . . ?
C9 C7 H7A 105.4 . . ?
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 . . ?
C7 C9 H9C 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
C7 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
C11 C10 C15 120.9(3) . . ?
C11 C10 N2 121.5(3) . . ?
C15 C10 N2 117.7(3) . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 117.0(4) . . ?
C13 C12 H12A 121.5 . . ?
C11 C12 H12A 121.5 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 121.1(4) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C14 C15 C10 118.3(4) . . ?
C14 C15 H15A 120.9 . . ?
C10 C15 H15A 120.9 . . ?
C21 C16 C17 119.9(3) . . ?
C21 C16 N2 120.0(3) . . ?
C17 C16 N2 120.1(3) . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C16 C21 C20 120.1(3) . . ?
C16 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
N3 C22 C24 115.8(3) . . ?
N3 C22 C23 113.6(2) . . ?
C24 C22 C23 110.0(2) . . ?
N3 C22 H22A 105.5 . . ?
C24 C22 H22A 105.5 . . ?
C23 C22 H22A 105.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24C 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24C C24 H24B 109.5 . . ?
C22 C24 H24A 109.5 . . ?
H24C C24 H24A 109.5 . . ?
H24B C24 H24A 109.5 . . ?
N3 C25 C27 115.1(3) . . ?
N3 C25 C26 112.4(3) . . ?
C27 C25 C26 110.9(3) . . ?
N3 C25 H25A 105.9 . . ?
C27 C25 H25A 105.9 . . ?
C26 C25 H25A 105.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 119.9(3) . . ?
C33 C28 N4 121.5(3) . . ?
C29 C28 N4 118.7(3) . . ?
C28 C29 C30 119.5(4) . . ?
C28 C29 H29A 120.2 . . ?
C30 C29 H29A 120.2 . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C32 C31 C30 119.1(4) . . ?
C32 C31 H31A 120.5 . . ?
C30 C31 H31A 120.5 . . ?
C31 C32 C33 121.0(4) . . ?
C31 C32 H32A 119.5 . . ?
C33 C32 H32A 119.5 . . ?
C28 C33 C32 119.9(4) . . ?
C28 C33 H33A 120.1 . . ?
C32 C33 H33A 120.1 . . ?
C39 C34 C35 119.9(3) . . ?
C39 C34 N4 121.9(2) . . ?
C35 C34 N4 118.2(3) . . ?
C36 C35 C34 119.7(3) . . ?
C36 C35 H35A 120.2 . . ?
C34 C35 H35A 120.2 . . ?
C37 C36 C35 120.2(3) . . ?
C37 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C36 C37 C38 120.1(3) . . ?
C36 C37 H37A 120.0 . . ?
C38 C37 H37A 120.0 . . ?
C37 C38 C39 119.6(3) . . ?
C37 C38 H38A 120.2 . . ?
C39 C38 H38A 120.2 . . ?
C34 C39 C38 120.5(3) . . ?
C34 C39 H39A 119.7 . . ?
C38 C39 H39A 119.7 . . ?
C41 C40 C42 121.7(5) . 3_766 ?
C41 C40 H40A 119.1 . . ?
C42 C40 H40A 119.1 3_766 . ?
C40 C41 C42 120.7(5) . . ?
C40 C41 H41A 119.7 . . ?
C42 C41 H41A 119.7 . . ?
C40 C42 C41 117.6(5) 3_766 . ?
C40 C42 H42A 121.2 3_766 . ?
C41 C42 H42A 121.2 . . ?
C1 N1 C7 120.9(2) . . ?
C1 N1 C4 117.3(3) . . ?
C7 N1 C4 121.5(2) . . ?
C1 N2 C16 121.1(2) . . ?
C1 N2 C10 120.2(2) . . ?
C16 N2 C10 117.0(2) . . ?
C3 N3 C22 118.6(3) . . ?
C3 N3 C25 119.1(2) . . ?
C22 N3 C25 122.1(2) . . ?
C3 N4 C34 120.8(2) . . ?
C3 N4 C28 120.3(2) . . ?
C34 N4 C28 117.5(2) . . ?
C2 O1 H1 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.28
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.047


_database_code_depnum_ccdc_archive 'CCDC 934512'