# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_121119b_0m


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H46 Cl Fe N6 O6'
_chemical_formula_weight         762.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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                   12.311(4)
_cell_length_b                   13.132(4)
_cell_length_c                   14.299(5)
_cell_angle_alpha                99.409(4)
_cell_angle_beta                 108.611(4)
_cell_angle_gamma                98.761(5)
_cell_volume                     2109.2(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5258
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.58

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.200
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             802
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9460
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14069
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.1380
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             7284
_reflns_number_gt                4151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1329P)²+0.0000P] where P=(Fo²+2Fc²)/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         7284
_refine_ls_number_parameters     483
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2299
_refine_ls_wR_factor_gt          0.2001
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

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
Fe1 Fe 0.38831(7) 0.09715(5) 0.29973(6) 0.0421(3) Uani 1 1 d . . .
C1 C 0.3483(5) 0.3202(4) 0.5369(4) 0.0450(13) Uani 1 1 d . . .
C2 C 0.3162(6) 0.3152(5) 0.6188(6) 0.0720(19) Uani 1 1 d . . .
H2 H 0.3058 0.2499 0.6389 0.086 Uiso 1 1 calc R . .
C3 C 0.2985(6) 0.4053(6) 0.6738(6) 0.081(2) Uani 1 1 d . . .
H3 H 0.2781 0.4018 0.7321 0.097 Uiso 1 1 calc R . .
C4 C 0.3103(7) 0.4968(6) 0.6441(7) 0.090(3) Uani 1 1 d . . .
H4A H 0.2990 0.5583 0.6818 0.107 Uiso 1 1 calc R . .
C5 C 0.3388(8) 0.5020(5) 0.5597(7) 0.089(2) Uani 1 1 d . . .
H5 H 0.3440 0.5663 0.5376 0.106 Uiso 1 1 calc R . .
C6 C 0.3598(6) 0.4150(5) 0.5070(5) 0.0658(17) Uani 1 1 d . . .
H6 H 0.3823 0.4197 0.4499 0.079 Uiso 1 1 calc R . .
C7 C 0.3647(4) 0.2260(4) 0.4729(4) 0.0401(12) Uani 1 1 d . . .
C8 C 0.3507(4) -0.0439(4) 0.4444(4) 0.0390(12) Uani 1 1 d . . .
H8 H 0.3409 -0.0509 0.5065 0.047 Uiso 1 1 calc R . .
C9 C 0.3531(4) -0.1357(4) 0.3789(4) 0.0380(11) Uani 1 1 d . . .
C10 C 0.3418(5) -0.2338(4) 0.4075(4) 0.0488(13) Uani 1 1 d . . .
H10 H 0.3323 -0.2358 0.4706 0.059 Uiso 1 1 calc R . .
C11 C 0.3439(5) -0.3249(4) 0.3491(4) 0.0512(14) Uani 1 1 d . . .
H11 H 0.3385 -0.3883 0.3727 0.061 Uiso 1 1 calc R . .
C12 C 0.3540(5) -0.3267(4) 0.2530(5) 0.0516(14) Uani 1 1 d . . .
C13 C 0.3639(5) -0.2309(4) 0.2225(4) 0.0469(13) Uani 1 1 d . . .
H13 H 0.3702 -0.2302 0.1581 0.056 Uiso 1 1 calc R . .
C14 C 0.3648(4) -0.1368(4) 0.2837(4) 0.0432(13) Uani 1 1 d . . .
C15 C 0.3648(7) -0.5178(5) 0.2309(6) 0.081(2) Uani 1 1 d . . .
H15A H 0.4073 -0.5594 0.1964 0.097 Uiso 1 1 calc R . .
H15B H 0.4104 -0.4995 0.3045 0.097 Uiso 1 1 calc R . .
C16 C 0.2485(8) -0.5815(6) 0.2119(7) 0.104(3) Uani 1 1 d . . .
H16A H 0.2068 -0.5406 0.2468 0.156 Uiso 1 1 calc R . .
H16B H 0.2567 -0.6459 0.2372 0.156 Uiso 1 1 calc R . .
H16C H 0.2038 -0.6006 0.1389 0.156 Uiso 1 1 calc R . .
C17 C 0.3511(8) -0.4247(5) 0.0889(6) 0.102(3) Uani 1 1 d D . .
H17A H 0.3027 -0.3767 0.0585 0.122 Uiso 1 1 calc R . .
H17B H 0.3140 -0.4977 0.0483 0.122 Uiso 1 1 calc R . .
C18 C 0.4703(9) -0.3946(11) 0.0865(11) 0.165(5) Uani 1 1 d D . .
H18A H 0.4969 -0.3174 0.1064 0.247 Uiso 1 1 calc R . .
H18B H 0.4693 -0.4199 0.0178 0.247 Uiso 1 1 calc R . .
H18C H 0.5241 -0.4265 0.1337 0.247 Uiso 1 1 calc R . .
C19 C 0.0491(5) 0.1194(4) 0.1000(4) 0.0457(13) Uani 1 1 d . . .
C20 C -0.0305(6) 0.0748(5) 0.1411(5) 0.0646(17) Uani 1 1 d . . .
H20 H -0.0045 0.0466 0.1995 0.078 Uiso 1 1 calc R . .
C21 C -0.1492(6) 0.0728(6) 0.0941(6) 0.079(2) Uani 1 1 d . . .
H21 H -0.2044 0.0469 0.1230 0.094 Uiso 1 1 calc R . .
C22 C -0.1867(6) 0.1075(6) 0.0076(6) 0.076(2) Uani 1 1 d . . .
H22 H -0.2684 0.1018 -0.0254 0.091 Uiso 1 1 calc R . .
C23 C -0.1093(6) 0.1503(6) -0.0329(6) 0.076(2) Uani 1 1 d . . .
H23 H -0.1372 0.1745 -0.0934 0.091 Uiso 1 1 calc R . .
C24 C 0.0097(5) 0.1587(5) 0.0141(5) 0.0604(16) Uani 1 1 d . . .
H24 H 0.0641 0.1911 -0.0125 0.072 Uiso 1 1 calc R . .
C25 C 0.4522(5) 0.2090(4) 0.1460(4) 0.0423(12) Uani 1 1 d . . .
H25 H 0.4287 0.2352 0.0862 0.051 Uiso 1 1 calc R . .
C26 C 0.5738(4) 0.2228(4) 0.1986(4) 0.0396(12) Uani 1 1 d . . .
C27 C 0.6226(4) 0.1886(4) 0.2893(4) 0.0391(12) Uani 1 1 d . . .
C28 C 0.7436(5) 0.2098(4) 0.3370(4) 0.0475(13) Uani 1 1 d . . .
H28 H 0.7748 0.1839 0.3961 0.057 Uiso 1 1 calc R . .
C29 C 0.8222(5) 0.2679(4) 0.3018(5) 0.0493(14) Uani 1 1 d . . .
C30 C 0.7734(5) 0.2986(5) 0.2103(5) 0.0555(15) Uani 1 1 d . . .
H30 H 0.8238 0.3349 0.1823 0.067 Uiso 1 1 calc R . .
C31 C 0.6546(5) 0.2767(4) 0.1613(4) 0.0500(14) Uani 1 1 d . . .
H31 H 0.6246 0.2985 0.0996 0.060 Uiso 1 1 calc R . .
C32 C 0.9940(6) 0.2654(6) 0.4493(5) 0.0716(19) Uani 1 1 d . . .
H32A H 0.9395 0.2657 0.4873 0.086 Uiso 1 1 calc R . .
H32B H 1.0664 0.3197 0.4898 0.086 Uiso 1 1 calc R . .
C33 C 1.0245(7) 0.1568(8) 0.4346(7) 0.102(3) Uani 1 1 d . . .
H33A H 0.9532 0.1031 0.3937 0.153 Uiso 1 1 calc R . .
H33B H 1.0585 0.1403 0.5008 0.153 Uiso 1 1 calc R . .
H33C H 1.0816 0.1574 0.4000 0.153 Uiso 1 1 calc R . .
C34 C 1.0223(6) 0.3590(6) 0.3204(6) 0.080(2) Uani 1 1 d . . .
H34A H 0.9937 0.3437 0.2455 0.096 Uiso 1 1 calc R . .
H34B H 1.1004 0.3412 0.3442 0.096 Uiso 1 1 calc R . .
C35 C 1.0344(7) 0.4749(6) 0.3608(7) 0.102(3) Uani 1 1 d . . .
H35A H 0.9609 0.4956 0.3277 0.153 Uiso 1 1 calc R . .
H35B H 1.0985 0.5159 0.3469 0.153 Uiso 1 1 calc R . .
H35C H 1.0516 0.4886 0.4341 0.153 Uiso 1 1 calc R . .
C49 C 0.1758(5) 0.1230(4) 0.1533(4) 0.0439(13) Uani 1 1 d . . .
Cl1 Cl 0.24635(17) 0.26523(16) 0.92912(14) 0.0806(6) Uani 1 1 d . . .
N1 N 0.3499(4) 0.1324(3) 0.4945(3) 0.0411(10) Uani 1 1 d . . .
H1 H 0.3340 0.1225 0.5486 0.049 Uiso 1 1 calc R . .
N2 N 0.3612(3) 0.0495(3) 0.4250(3) 0.0381(10) Uani 1 1 d . . .
N3 N 0.3553(6) -0.4186(4) 0.1932(4) 0.0722(16) Uani 1 1 d . . .
N4 N 0.2563(4) 0.1614(3) 0.1160(3) 0.0414(10) Uani 1 1 d . . .
H4 H 0.2378 0.1837 0.0594 0.050 Uiso 1 1 calc R . .
N5 N 0.3703(4) 0.1630(3) 0.1736(3) 0.0392(10) Uani 1 1 d . . .
N6 N 0.9402(4) 0.2919(4) 0.3533(4) 0.0677(15) Uani 1 1 d . . .
O1 O 0.3912(3) 0.2358(3) 0.3951(3) 0.0483(9) Uani 1 1 d . . .
O2 O 0.3752(3) -0.0493(3) 0.2488(3) 0.0522(10) Uani 1 1 d . . .
O3 O 0.2092(3) 0.0890(3) 0.2336(3) 0.0490(9) Uani 1 1 d . . .
O4 O 0.5562(3) 0.1376(3) 0.3290(3) 0.0492(9) Uani 1 1 d . . .
O1W O 0.2576(5) 0.0591(4) 0.6343(4) 0.1007(18) Uani 1 1 d . . .
H1W H 0.3100 0.0683 0.6894 0.121 Uiso 1 1 d R . .
H2W H 0.1966 0.0757 0.6360 0.121 Uiso 1 1 d R . .
C1S C 0.443(3) 0.067(2) 0.895(3) 0.126(8) Uani 0.30 1 d P . .
H1S1 H 0.3996 0.0370 0.9348 0.189 Uiso 0.30 1 d PR . .
H1S2 H 0.5077 0.1253 0.9399 0.189 Uiso 0.30 1 d PR . .
H1S3 H 0.4752 0.0117 0.8647 0.189 Uiso 0.30 1 d PR . .
O1S O 0.3701(16) 0.0964(14) 0.818(2) 0.126(8) Uani 0.30 1 d P . .
H1S H 0.3360 0.1361 0.8428 0.152 Uiso 0.30 1 d PR . .
C2S C -0.0292(11) 0.1342(13) 0.6814(10) 0.040(2) Uani 0.35 1 d P . .
H2S1 H -0.0643 0.1312 0.6089 0.060 Uiso 0.35 1 d PR . .
H2S2 H -0.0357 0.2003 0.7204 0.060 Uiso 0.35 1 d PR . .
H2S3 H -0.0707 0.0740 0.6982 0.060 Uiso 0.35 1 d PR . .
O2S O 0.0866(7) 0.1308(8) 0.7056(7) 0.040(2) Uani 0.35 1 d P . .
H2S H 0.1276 0.1648 0.7628 0.048 Uiso 0.35 1 d PR . .
C3S C 0.011(3) 0.421(3) 0.876(3) 0.151(7) Uani 0.35 1 d P . .
H3S1 H -0.0500 0.3640 0.8258 0.226 Uiso 0.35 1 d PR . .
H3S2 H -0.0188 0.4862 0.8818 0.226 Uiso 0.35 1 d PR . .
H3S3 H 0.0343 0.4022 0.9421 0.226 Uiso 0.35 1 d PR . .
O3S O 0.107(2) 0.432(2) 0.8434(15) 0.151(7) Uani 0.35 1 d P . .
H3S H 0.1423 0.3870 0.8640 0.181 Uiso 0.35 1 d PR . .


_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
Fe1 O2 1.904(3) . ?
Fe1 O4 1.942(4) . ?
Fe1 O1 2.077(4) . ?
Fe1 O3 2.082(4) . ?
Fe1 N5 2.088(4) . ?
Fe1 N2 2.098(4) . ?
C1 C2 1.359(8) . ?
C1 C6 1.383(8) . ?
C1 C7 1.494(7) . ?
C2 C3 1.396(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.341(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(11) . ?
C4 H4A 0.9500 . ?
C5 C6 1.369(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.274(6) . ?
C7 N1 1.316(6) . ?
C8 N2 1.297(6) . ?
C8 C9 1.411(7) . ?
C8 H8 0.9500 . ?
C9 C14 1.412(7) . ?
C9 C10 1.414(7) . ?
C10 C11 1.351(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(8) . ?
C11 H11 0.9500 . ?
C12 N3 1.365(7) . ?
C12 C13 1.398(7) . ?
C13 C14 1.390(7) . ?
C13 H13 0.9500 . ?
C14 O2 1.330(6) . ?
C15 C16 1.462(10) . ?
C15 N3 1.495(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.465(9) . ?
C17 C18 1.474(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.384(8) . ?
C19 C20 1.398(8) . ?
C19 C49 1.491(7) . ?
C20 C21 1.394(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.354(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.362(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 N5 1.298(6) . ?
C25 C26 1.413(7) . ?
C25 H25 0.9500 . ?
C26 C31 1.422(7) . ?
C26 C27 1.421(7) . ?
C27 O4 1.301(6) . ?
C27 C28 1.387(7) . ?
C28 C29 1.408(7) . ?
C28 H28 0.9500 . ?
C29 N6 1.362(7) . ?
C29 C30 1.407(8) . ?
C30 C31 1.366(8) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 N6 1.445(8) . ?
C32 C33 1.528(11) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 N6 1.478(8) . ?
C34 C35 1.503(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C49 O3 1.269(6) . ?
C49 N4 1.338(7) . ?
N1 N2 1.405(5) . ?
N1 H1 0.8800 . ?
N4 N5 1.377(6) . ?
N4 H4 0.8800 . ?
O1W H1W 0.8200 . ?
O1W H2W 0.8200 . ?
C1S O1S 1.34(4) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1S H1S 0.8199 . ?
C2S O2S 1.366(15) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O2S H2S 0.8199 . ?
C3S O3S 1.40(3) . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?
O3S H3S 0.8201 . ?

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
O2 Fe1 O4 95.36(16) . . ?
O2 Fe1 O1 160.18(15) . . ?
O4 Fe1 O1 91.59(15) . . ?
O2 Fe1 O3 93.88(16) . . ?
O4 Fe1 O3 159.71(15) . . ?
O1 Fe1 O3 85.69(15) . . ?
O2 Fe1 N5 104.05(16) . . ?
O4 Fe1 N5 85.63(15) . . ?
O1 Fe1 N5 94.96(15) . . ?
O3 Fe1 N5 74.60(15) . . ?
O2 Fe1 N2 85.08(16) . . ?
O4 Fe1 N2 108.60(15) . . ?
O1 Fe1 N2 75.11(15) . . ?
O3 Fe1 N2 90.16(15) . . ?
N5 Fe1 N2 162.56(16) . . ?
C2 C1 C6 119.1(5) . . ?
C2 C1 C7 123.0(5) . . ?
C6 C1 C7 117.8(5) . . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.2(6) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.9(7) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N1 119.4(4) . . ?
O1 C7 C1 119.7(4) . . ?
N1 C7 C1 120.9(5) . . ?
N2 C8 C9 123.9(5) . . ?
N2 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C8 C9 C14 123.8(4) . . ?
C8 C9 C10 119.5(5) . . ?
C14 C9 C10 116.7(5) . . ?
C11 C10 C9 122.9(5) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 C12 120.7(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N3 C12 C13 121.6(5) . . ?
N3 C12 C11 121.0(5) . . ?
C13 C12 C11 117.4(5) . . ?
C14 C13 C12 121.9(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
O2 C14 C13 117.8(5) . . ?
O2 C14 C9 121.8(4) . . ?
C13 C14 C9 120.4(5) . . ?
C16 C15 N3 110.9(7) . . ?
C16 C15 H15A 109.5 . . ?
N3 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
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 . . ?
N3 C17 C18 110.6(8) . . ?
N3 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 120.3(5) . . ?
C24 C19 C49 122.6(5) . . ?
C20 C19 C49 117.1(5) . . ?
C19 C20 C21 118.1(7) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.1(7) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 120.1(7) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 119.5(6) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
N5 C25 C26 124.6(5) . . ?
N5 C25 H25 117.7 . . ?
C26 C25 H25 117.7 . . ?
C25 C26 C31 118.9(5) . . ?
C25 C26 C27 124.3(4) . . ?
C31 C26 C27 116.7(5) . . ?
O4 C27 C28 118.9(5) . . ?
O4 C27 C26 121.5(5) . . ?
C28 C27 C26 119.6(5) . . ?
C27 C28 C29 122.9(5) . . ?
C27 C28 H28 118.5 . . ?
C29 C28 H28 118.5 . . ?
N6 C29 C28 121.5(6) . . ?
N6 C29 C30 121.5(5) . . ?
C28 C29 C30 117.0(5) . . ?
C31 C30 C29 120.8(5) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C26 122.8(5) . . ?
C30 C31 H31 118.6 . . ?
C26 C31 H31 118.6 . . ?
N6 C32 C33 111.5(6) . . ?
N6 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N6 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N6 C34 C35 112.1(6) . . ?
N6 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
N6 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O3 C49 N4 118.9(5) . . ?
O3 C49 C19 120.9(5) . . ?
N4 C49 C19 120.2(5) . . ?
C7 N1 N2 115.2(4) . . ?
C7 N1 H1 122.4 . . ?
N2 N1 H1 122.4 . . ?
C8 N2 N1 117.6(4) . . ?
C8 N2 Fe1 129.3(3) . . ?
N1 N2 Fe1 113.1(3) . . ?
C12 N3 C17 121.6(5) . . ?
C12 N3 C15 122.3(5) . . ?
C17 N3 C15 116.0(5) . . ?
C49 N4 N5 114.5(4) . . ?
C49 N4 H4 122.7 . . ?
N5 N4 H4 122.7 . . ?
C25 N5 N4 116.7(4) . . ?
C25 N5 Fe1 128.5(4) . . ?
N4 N5 Fe1 114.8(3) . . ?
C29 N6 C32 123.5(5) . . ?
C29 N6 C34 121.6(6) . . ?
C32 N6 C34 114.5(5) . . ?
C7 O1 Fe1 116.7(3) . . ?
C14 O2 Fe1 135.8(3) . . ?
C49 O3 Fe1 117.1(3) . . ?
C27 O4 Fe1 135.4(3) . . ?
H1W O1W H2W 115.6 . . ?
O1S C1S H1S1 109.8 . . ?
O1S C1S H1S2 112.3 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 106.2 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S O1S H1S 106.8 . . ?
O2S C2S H2S1 109.8 . . ?
O2S C2S H2S2 109.1 . . ?
H2S1 C2S H2S2 109.5 . . ?
O2S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C2S O2S H2S 113.2 . . ?
O3S C3S H3S1 106.3 . . ?
O3S C3S H3S2 112.6 . . ?
H3S1 C3S H3S2 109.5 . . ?
O3S C3S H3S3 109.4 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
C3S O3S H3S 104.9 . . ?

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
C6 C1 C2 C3 -1.8(10) . . . . ?
C7 C1 C2 C3 -177.9(6) . . . . ?
C1 C2 C3 C4 1.6(11) . . . . ?
C2 C3 C4 C5 0.5(12) . . . . ?
C3 C4 C5 C6 -2.5(13) . . . . ?
C4 C5 C6 C1 2.3(12) . . . . ?
C2 C1 C6 C5 -0.1(10) . . . . ?
C7 C1 C6 C5 176.2(6) . . . . ?
C2 C1 C7 O1 177.8(6) . . . . ?
C6 C1 C7 O1 1.6(8) . . . . ?
C2 C1 C7 N1 -0.9(8) . . . . ?
C6 C1 C7 N1 -177.0(5) . . . . ?
N2 C8 C9 C14 -1.2(8) . . . . ?
N2 C8 C9 C10 179.5(5) . . . . ?
C8 C9 C10 C11 -179.6(5) . . . . ?
C14 C9 C10 C11 1.1(8) . . . . ?
C9 C10 C11 C12 -2.0(9) . . . . ?
C10 C11 C12 N3 -179.5(6) . . . . ?
C10 C11 C12 C13 1.2(9) . . . . ?
N3 C12 C13 C14 -178.8(5) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
C12 C13 C14 O2 179.7(5) . . . . ?
C12 C13 C14 C9 -1.4(8) . . . . ?
C8 C9 C14 O2 0.3(8) . . . . ?
C10 C9 C14 O2 179.5(5) . . . . ?
C8 C9 C14 C13 -178.7(5) . . . . ?
C10 C9 C14 C13 0.6(7) . . . . ?
C24 C19 C20 C21 -1.0(9) . . . . ?
C49 C19 C20 C21 178.5(5) . . . . ?
C19 C20 C21 C22 3.9(10) . . . . ?
C20 C21 C22 C23 -3.5(11) . . . . ?
C21 C22 C23 C24 0.2(11) . . . . ?
C22 C23 C24 C19 2.6(10) . . . . ?
C20 C19 C24 C23 -2.1(9) . . . . ?
C49 C19 C24 C23 178.4(5) . . . . ?
N5 C25 C26 C31 -178.6(5) . . . . ?
N5 C25 C26 C27 -0.4(8) . . . . ?
C25 C26 C27 O4 2.5(7) . . . . ?
C31 C26 C27 O4 -179.3(4) . . . . ?
C25 C26 C27 C28 -177.5(5) . . . . ?
C31 C26 C27 C28 0.7(7) . . . . ?
O4 C27 C28 C29 -177.5(5) . . . . ?
C26 C27 C28 C29 2.5(8) . . . . ?
C27 C28 C29 N6 176.6(5) . . . . ?
C27 C28 C29 C30 -4.3(8) . . . . ?
N6 C29 C30 C31 -177.9(5) . . . . ?
C28 C29 C30 C31 3.0(8) . . . . ?
C29 C30 C31 C26 0.1(9) . . . . ?
C25 C26 C31 C30 176.3(5) . . . . ?
C27 C26 C31 C30 -2.0(8) . . . . ?
C24 C19 C49 O3 178.0(5) . . . . ?
C20 C19 C49 O3 -1.5(7) . . . . ?
C24 C19 C49 N4 -2.8(8) . . . . ?
C20 C19 C49 N4 177.7(5) . . . . ?
O1 C7 N1 N2 -2.2(7) . . . . ?
C1 C7 N1 N2 176.4(4) . . . . ?
C9 C8 N2 N1 176.1(4) . . . . ?
C9 C8 N2 Fe1 -1.8(7) . . . . ?
C7 N1 N2 C8 178.0(4) . . . . ?
C7 N1 N2 Fe1 -3.7(5) . . . . ?
O2 Fe1 N2 C8 4.0(4) . . . . ?
O4 Fe1 N2 C8 -90.1(4) . . . . ?
O1 Fe1 N2 C8 -176.7(4) . . . . ?
O3 Fe1 N2 C8 97.8(4) . . . . ?
N5 Fe1 N2 C8 126.6(5) . . . . ?
O2 Fe1 N2 N1 -174.0(3) . . . . ?
O4 Fe1 N2 N1 92.0(3) . . . . ?
O1 Fe1 N2 N1 5.3(3) . . . . ?
O3 Fe1 N2 N1 -80.1(3) . . . . ?
N5 Fe1 N2 N1 -51.4(6) . . . . ?
C13 C12 N3 C17 -8.4(10) . . . . ?
C11 C12 N3 C17 172.3(7) . . . . ?
C13 C12 N3 C15 169.7(6) . . . . ?
C11 C12 N3 C15 -9.6(10) . . . . ?
C18 C17 N3 C12 87.3(9) . . . . ?
C18 C17 N3 C15 -90.9(9) . . . . ?
C16 C15 N3 C12 90.6(8) . . . . ?
C16 C15 N3 C17 -91.2(8) . . . . ?
O3 C49 N4 N5 -2.4(6) . . . . ?
C19 C49 N4 N5 178.3(4) . . . . ?
C26 C25 N5 N4 176.8(4) . . . . ?
C26 C25 N5 Fe1 0.4(7) . . . . ?
C49 N4 N5 C25 -173.4(4) . . . . ?
C49 N4 N5 Fe1 3.5(5) . . . . ?
O2 Fe1 N5 C25 -95.8(4) . . . . ?
O4 Fe1 N5 C25 -1.4(4) . . . . ?
O1 Fe1 N5 C25 89.8(4) . . . . ?
O3 Fe1 N5 C25 174.0(4) . . . . ?
N2 Fe1 N5 C25 144.1(5) . . . . ?
O2 Fe1 N5 N4 87.7(3) . . . . ?
O4 Fe1 N5 N4 -177.9(3) . . . . ?
O1 Fe1 N5 N4 -86.6(3) . . . . ?
O3 Fe1 N5 N4 -2.5(3) . . . . ?
N2 Fe1 N5 N4 -32.4(7) . . . . ?
C28 C29 N6 C32 -3.3(9) . . . . ?
C30 C29 N6 C32 177.7(6) . . . . ?
C28 C29 N6 C34 -175.8(6) . . . . ?
C30 C29 N6 C34 5.2(9) . . . . ?
C33 C32 N6 C29 90.3(8) . . . . ?
C33 C32 N6 C34 -96.7(7) . . . . ?
C35 C34 N6 C29 85.0(8) . . . . ?
C35 C34 N6 C32 -88.2(8) . . . . ?
N1 C7 O1 Fe1 7.3(6) . . . . ?
C1 C7 O1 Fe1 -171.4(3) . . . . ?
O2 Fe1 O1 C7 -5.0(7) . . . . ?
O4 Fe1 O1 C7 -115.6(4) . . . . ?
O3 Fe1 O1 C7 84.5(4) . . . . ?
N5 Fe1 O1 C7 158.6(4) . . . . ?
N2 Fe1 O1 C7 -6.8(3) . . . . ?
C13 C14 O2 Fe1 -176.6(4) . . . . ?
C9 C14 O2 Fe1 4.5(8) . . . . ?
O4 Fe1 O2 C14 102.8(5) . . . . ?
O1 Fe1 O2 C14 -7.2(8) . . . . ?
O3 Fe1 O2 C14 -95.3(5) . . . . ?
N5 Fe1 O2 C14 -170.4(5) . . . . ?
N2 Fe1 O2 C14 -5.5(5) . . . . ?
N4 C49 O3 Fe1 0.2(6) . . . . ?
C19 C49 O3 Fe1 179.4(3) . . . . ?
O2 Fe1 O3 C49 -102.2(4) . . . . ?
O4 Fe1 O3 C49 14.8(7) . . . . ?
O1 Fe1 O3 C49 97.7(4) . . . . ?
N5 Fe1 O3 C49 1.3(3) . . . . ?
N2 Fe1 O3 C49 172.7(4) . . . . ?
C28 C27 O4 Fe1 175.1(4) . . . . ?
C26 C27 O4 Fe1 -4.9(7) . . . . ?
O2 Fe1 O4 C27 107.5(5) . . . . ?
O1 Fe1 O4 C27 -91.0(5) . . . . ?
O3 Fe1 O4 C27 -9.2(8) . . . . ?
N5 Fe1 O4 C27 3.8(5) . . . . ?
N2 Fe1 O4 C27 -165.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 Cl1 0.88 2.32 3.171(5) 163.5 1_554
O3S H3S Cl1 0.82 2.33 3.146(17) 177.5 .
O2S H2S Cl1 0.82 2.39 3.207(9) 179.5 .
O1S H1S Cl1 0.82 2.52 3.342(17) 175.5 .
O1W H2W O2S 0.82 2.07 2.832(9) 155.3 .
O1W H1W O1S 0.82 1.71 2.48(3) 155.9 .
N1 H1 O1W 0.88 1.98 2.820(6) 160.0 .

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.125
_database_code_depnum_ccdc_archive 'CCDC 918855'
#######################################################################
#
#                 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_e:\120630a\work\mo_120630a_0m


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 N3 O3'
_chemical_formula_weight         355.43

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.3190(15)
_cell_length_b                   15.155(2)
_cell_length_c                   13.3440(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.348(2)
_cell_angle_gamma                90.00
_cell_volume                     1969.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5326
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      30.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.199
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13258
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3864
_reflns_number_gt                3049
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0855P)²+0.4939P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0076(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3864
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 1.4220(3) 0.12904(16) 0.4189(2) 0.0894(8) Uani 1 1 d . . .
H1A H 1.3768 0.1242 0.3436 0.134 Uiso 1 1 calc R . .
H1B H 1.4529 0.0718 0.4479 0.134 Uiso 1 1 calc R . .
H1C H 1.4994 0.1680 0.4328 0.134 Uiso 1 1 calc R . .
C2 C 1.27469(16) 0.24566(11) 0.43684(13) 0.0490(4) Uani 1 1 d . . .
C3 C 1.29644(17) 0.29580(11) 0.35744(14) 0.0519(4) Uani 1 1 d . . .
H3 H 1.3506 0.2742 0.3194 0.062 Uiso 1 1 calc R . .
C4 C 1.23701(18) 0.37834(11) 0.33514(13) 0.0510(4) Uani 1 1 d . . .
H4 H 1.2499 0.4116 0.2806 0.061 Uiso 1 1 calc R . .
C5 C 1.15854(16) 0.41256(11) 0.39241(12) 0.0459(4) Uani 1 1 d . . .
C6 C 1.13784(18) 0.36106(12) 0.47188(14) 0.0533(4) Uani 1 1 d . . .
H6 H 1.0855 0.3830 0.5112 0.064 Uiso 1 1 calc R . .
C7 C 1.19398(19) 0.27791(12) 0.49308(14) 0.0561(4) Uani 1 1 d . . .
H7 H 1.1776 0.2434 0.5453 0.067 Uiso 1 1 calc R . .
C8 C 1.10608(17) 0.50505(11) 0.38000(13) 0.0488(4) Uani 1 1 d . . .
C9 C 0.9957(2) 0.62866(11) 0.26547(16) 0.0653(5) Uani 1 1 d . . .
H9A H 0.8982 0.6327 0.2499 0.098 Uiso 1 1 calc R . .
H9B H 1.0198 0.6530 0.2076 0.098 Uiso 1 1 calc R . .
H9C H 1.0416 0.6611 0.3292 0.098 Uiso 1 1 calc R . .
C10 C 0.91007(17) 0.50142(11) 0.10777(13) 0.0493(4) Uani 1 1 d . . .
H10 H 0.8891 0.5611 0.0968 0.059 Uiso 1 1 calc R . .
C11 C 0.85278(17) 0.43984(11) 0.02163(12) 0.0474(4) Uani 1 1 d . . .
C12 C 0.88619(17) 0.34949(11) 0.02843(12) 0.0474(4) Uani 1 1 d . . .
C13 C 0.82616(19) 0.29232(12) -0.05464(14) 0.0571(5) Uani 1 1 d . . .
H13 H 0.8503 0.2330 -0.0475 0.069 Uiso 1 1 calc R . .
C14 C 0.7295(2) 0.32217(14) -0.14940(14) 0.0621(5) Uani 1 1 d . . .
C15 C 0.6970(2) 0.41283(14) -0.15694(15) 0.0642(5) Uani 1 1 d . . .
H15 H 0.6341 0.4350 -0.2191 0.077 Uiso 1 1 calc R . .
C16 C 0.75725(19) 0.46877(13) -0.07363(14) 0.0578(5) Uani 1 1 d . . .
H16 H 0.7335 0.5282 -0.0809 0.069 Uiso 1 1 calc R . .
C17 C 0.7231(3) 0.1766(2) -0.2383(2) 0.1084(10) Uani 1 1 d . . .
H17A H 0.7211 0.1660 -0.3105 0.130 Uiso 1 1 calc R . .
H17B H 0.8179 0.1737 -0.1919 0.130 Uiso 1 1 calc R . .
C18 C 0.6423(5) 0.1083(3) -0.2074(3) 0.1530(15) Uani 1 1 d . . .
H18A H 0.6406 0.1204 -0.1372 0.229 Uiso 1 1 calc R . .
H18B H 0.6834 0.0516 -0.2081 0.229 Uiso 1 1 calc R . .
H18C H 0.5501 0.1082 -0.2566 0.229 Uiso 1 1 calc R . .
C19 C 0.5569(2) 0.2951(2) -0.32578(17) 0.0893(8) Uani 1 1 d . . .
H19A H 0.4991 0.3365 -0.3045 0.107 Uiso 1 1 calc R . .
H19B H 0.5006 0.2448 -0.3584 0.107 Uiso 1 1 calc R . .
C20 C 0.6083(3) 0.3386(3) -0.4066(2) 0.1244(13) Uani 1 1 d . . .
H20A H 0.6619 0.3895 -0.3755 0.187 Uiso 1 1 calc R . .
H20B H 0.5316 0.3563 -0.4667 0.187 Uiso 1 1 calc R . .
H20C H 0.6642 0.2977 -0.4291 0.187 Uiso 1 1 calc R . .
N1 N 1.03783(15) 0.53615(8) 0.28039(11) 0.0511(4) Uani 1 1 d . . .
N2 N 0.98915(14) 0.47543(8) 0.19889(10) 0.0464(3) Uani 1 1 d . . .
N3 N 0.6668(2) 0.26538(15) -0.23131(15) 0.0897(6) Uani 1 1 d . . .
O1 O 1.32862(14) 0.16334(8) 0.46698(12) 0.0671(4) Uani 1 1 d . . .
O2 O 1.12583(15) 0.55265(9) 0.45772(10) 0.0669(4) Uani 1 1 d . . .
O3 O 0.97866(14) 0.31510(8) 0.11729(9) 0.0606(4) Uani 1 1 d . . .
H3A H 0.9990 0.3524 0.1645 0.091 Uiso 1 1 calc R . .


_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 O1 1.421(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.371(2) . ?
C2 C3 1.381(2) . ?
C2 C7 1.382(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 C8 1.492(2) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.2237(19) . ?
C8 N1 1.366(2) . ?
C9 N1 1.462(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.281(2) . ?
C10 C11 1.446(2) . ?
C10 H10 0.9300 . ?
C11 C16 1.396(2) . ?
C11 C12 1.408(2) . ?
C12 O3 1.3558(19) . ?
C12 C13 1.381(2) . ?
C13 C14 1.401(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.373(2) . ?
C14 C15 1.410(3) . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.472(5) . ?
C17 N3 1.480(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N3 1.460(3) . ?
C19 C20 1.502(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.3856(17) . ?
O3 H3A 0.8200 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.91(16) . . ?
O1 C2 C7 114.94(15) . . ?
C3 C2 C7 120.15(15) . . ?
C2 C3 C4 119.35(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.27(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.47(15) . . ?
C4 C5 C8 123.19(15) . . ?
C6 C5 C8 118.08(14) . . ?
C7 C6 C5 120.71(16) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.03(16) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O2 C8 N1 120.59(15) . . ?
O2 C8 C5 120.49(15) . . ?
N1 C8 C5 118.91(13) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 121.33(15) . . ?
N2 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C16 C11 C12 116.62(15) . . ?
C16 C11 C10 120.02(16) . . ?
C12 C11 C10 123.34(15) . . ?
O3 C12 C13 117.34(15) . . ?
O3 C12 C11 121.11(14) . . ?
C13 C12 C11 121.55(16) . . ?
C12 C13 C14 121.18(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
N3 C14 C13 121.5(2) . . ?
N3 C14 C15 121.06(19) . . ?
C13 C14 C15 117.41(17) . . ?
C16 C15 C14 120.74(17) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 122.49(18) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C18 C17 N3 110.6(3) . . ?
C18 C17 H17A 109.5 . . ?
N3 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 113.4(2) . . ?
N3 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N3 C19 H19B 108.9 . . ?
C20 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 . . ?
C8 N1 N2 118.08(13) . . ?
C8 N1 C9 119.86(14) . . ?
N2 N1 C9 121.07(14) . . ?
C10 N2 N1 119.46(13) . . ?
C14 N3 C19 121.4(2) . . ?
C14 N3 C17 121.9(2) . . ?
C19 N3 C17 115.8(2) . . ?
C2 O1 C1 118.07(16) . . ?
C12 O3 H3A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.48(15) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C3 C4 C5 C8 172.60(15) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C8 C5 C6 C7 -174.43(16) . . . . ?
C5 C6 C7 C2 1.6(3) . . . . ?
O1 C2 C7 C6 178.02(16) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C4 C5 C8 O2 -128.30(19) . . . . ?
C6 C5 C8 O2 45.8(2) . . . . ?
C4 C5 C8 N1 50.6(2) . . . . ?
C6 C5 C8 N1 -135.34(17) . . . . ?
N2 C10 C11 C16 174.20(16) . . . . ?
N2 C10 C11 C12 -4.6(3) . . . . ?
C16 C11 C12 O3 179.47(16) . . . . ?
C10 C11 C12 O3 -1.7(3) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
C10 C11 C12 C13 178.11(16) . . . . ?
O3 C12 C13 C14 179.97(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 N3 -178.34(19) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
N3 C14 C15 C16 178.16(19) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C10 C11 C16 C15 -178.33(17) . . . . ?
O2 C8 N1 N2 -164.66(16) . . . . ?
C5 C8 N1 N2 16.5(2) . . . . ?
O2 C8 N1 C9 4.0(3) . . . . ?
C5 C8 N1 C9 -174.84(16) . . . . ?
C11 C10 N2 N1 -177.67(14) . . . . ?
C8 N1 N2 C10 171.21(15) . . . . ?
C9 N1 N2 C10 2.7(2) . . . . ?
C13 C14 N3 C19 174.1(2) . . . . ?
C15 C14 N3 C19 -4.8(3) . . . . ?
C13 C14 N3 C17 -17.6(4) . . . . ?
C15 C14 N3 C17 163.5(2) . . . . ?
C20 C19 N3 C14 83.0(3) . . . . ?
C20 C19 N3 C17 -86.0(3) . . . . ?
C18 C17 N3 C14 104.1(3) . . . . ?
C18 C17 N3 C19 -87.0(3) . . . . ?
C3 C2 O1 C1 4.9(3) . . . . ?
C7 C2 O1 C1 -174.75(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A N2 0.82 1.93 2.6501(17) 145.9 .
O3 H3A N2 0.82 1.93 2.6501(17) 145.9 .
C6 H6 O2 0.93 2.55 3.419(2) 156.6 3_766
C9 H9C O3 0.96 2.47 3.198(2) 132.5 2_755

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 910500'
