# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Peter Scott'
'Laura E N Allan'
'James Barker'
'Nikola P Chmel'
'Guy J. Clarkson'
'Suzanne E Howson'
'Scott Turner'

_publ_contact_author_name        'Peter Scott'
_publ_contact_author_email       PETER.SCOTT@WARWICK.AC.UK

_publ_section_title              
;
Organic-soluble optically pure anionic metal complexes;
PPh4[M(S,S-EDDS)]*2H2O (M = Fe, Co, Cr)
;

# Attachment 'compound_3.cif'

data_nc2
_database_code_depnum_ccdc_archive 'CCDC 755825'
#TrackingRef 'compound_3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H36 Co N2 O10 P'
_chemical_formula_weight         722.55

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   16.9107(6)
_cell_length_b                   12.8825(4)
_cell_length_c                   7.3322(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1597.34(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25075
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      32.65

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'

_exptl_special_details           
;
The data collection nominally covered over a hemisphere of
Reciprocal space, by a combination of 14 sets of exposures with
different \f angles for the crystal; each exposure covered
0.3\% in \w.
The crystal-to-detector distance was 5.5 cm.
Crystal decay was found to be negligible by by repeating the initial
frames at the end of data collection and analyzing the duplicate
reflections.

Hydrogen atoms were added at calculated positions and refined using
a riding model except the hydrogens on the nitrogen which we located
in a dffrence map. Anisotropic displacement parameters were used for all
non-H atoms; H-atoms were given isotropic displacement parameter equal
to 1.2 (or 1.5 for methyl or NH H-atoms) times the equivalent isotropic
displacement parameter of the atom to which they are attached.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            50153
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         32.83
_reflns_number_total             5741
_reflns_number_gt                5017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (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^)+(0.0500P)^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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 2459 Friedel pairs'
_refine_ls_abs_structure_Flack   0.009(9)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5741
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
P1 P 0.0000 0.0000 0.93549(6) 0.02679(8) Uani 1 2 d S . .
C6 C 0.02934(7) 0.10390(10) 0.78963(19) 0.0306(2) Uani 1 1 d . . .
C7 C -0.02526(9) 0.14517(15) 0.6678(3) 0.0517(4) Uani 1 1 d . . .
H7A H -0.0771 0.1212 0.6681 0.062 Uiso 1 1 calc R . .
C8 C -0.00288(15) 0.22119(15) 0.5469(2) 0.0586(4) Uani 1 1 d . . .
H8A H -0.0399 0.2500 0.4681 0.070 Uiso 1 1 calc R . .
C9 C 0.07388(13) 0.25443(13) 0.5425(2) 0.0513(4) Uani 1 1 d . . .
H9A H 0.0890 0.3056 0.4601 0.062 Uiso 1 1 calc R . .
C10 C 0.12806(10) 0.21319(14) 0.6577(3) 0.0535(4) Uani 1 1 d . . .
H10A H 0.1804 0.2351 0.6515 0.064 Uiso 1 1 calc R . .
C11 C 0.10637(8) 0.13840(12) 0.7853(2) 0.0410(3) Uani 1 1 d . . .
H11A H 0.1435 0.1121 0.8667 0.049 Uiso 1 1 calc R . .
C12 C 0.07891(7) -0.03816(10) 1.08316(18) 0.0285(2) Uani 1 1 d . . .
C13 C 0.10672(10) -0.13851(12) 1.0881(3) 0.0462(4) Uani 1 1 d . . .
H13A H 0.0875 -0.1879 1.0070 0.055 Uiso 1 1 calc R . .
C14 C 0.16395(11) -0.16502(13) 1.2159(3) 0.0592(5) Uani 1 1 d . . .
H14A H 0.1831 -0.2326 1.2205 0.071 Uiso 1 1 calc R . .
C15 C 0.19233(8) -0.09219(15) 1.3352(2) 0.0476(4) Uani 1 1 d . . .
H15A H 0.2306 -0.1107 1.4203 0.057 Uiso 1 1 calc R . .
C16 C 0.16486(8) 0.00753(15) 1.3300(2) 0.0454(3) Uani 1 1 d . . .
H16A H 0.1848 0.0568 1.4106 0.055 Uiso 1 1 calc R . .
C17 C 0.10760(9) 0.03506(12) 1.2054(2) 0.0415(3) Uani 1 1 d . . .
H17A H 0.0882 0.1026 1.2032 0.050 Uiso 1 1 calc R . .
Co1 Co 0.0000 0.5000 0.14410(3) 0.02324(6) Uani 1 2 d S . .
O1 O 0.07132(5) 0.54168(8) 0.33311(12) 0.0349(2) Uani 1 1 d . . .
O2 O 0.18339(6) 0.59468(11) 0.45239(17) 0.0519(3) Uani 1 1 d . . .
O3 O 0.04179(5) 0.36291(7) 0.13821(14) 0.03288(19) Uani 1 1 d . . .
O4 O 0.15985(7) 0.28814(9) 0.11814(18) 0.0502(3) Uani 1 1 d . . .
N1 N 0.07674(6) 0.52392(8) -0.04283(14) 0.0273(2) Uani 1 1 d . . .
H1A H 0.0916 0.5833 -0.0489 0.033 Uiso 1 1 d R . .
C1 C 0.14613(7) 0.55514(11) 0.32727(18) 0.0326(3) Uani 1 1 d . . .
C2 C 0.19243(7) 0.52259(11) 0.1583(2) 0.0374(3) Uani 1 1 d . . .
H2A H 0.2140 0.5845 0.1017 0.045 Uiso 1 1 calc R . .
H2B H 0.2367 0.4801 0.1970 0.045 Uiso 1 1 calc R . .
C3 C 0.14628(7) 0.46308(11) 0.01569(18) 0.0324(3) Uani 1 1 d . . .
H3A H 0.1802 0.4487 -0.0896 0.039 Uiso 1 1 calc R . .
C4 C 0.11548(8) 0.36155(11) 0.09496(18) 0.0333(3) Uani 1 1 d . . .
C5 C 0.04331(8) 0.48672(12) -0.21890(17) 0.0359(3) Uani 1 1 d . . .
H5A H 0.0505 0.4123 -0.2304 0.043 Uiso 1 1 calc R . .
H5B H 0.0697 0.5204 -0.3204 0.043 Uiso 1 1 calc R . .
O5 O 0.31750(7) 0.19195(11) 0.2020(2) 0.0596(3) Uani 1 1 d . . .
H5D H 0.2751 0.2265 0.1872 0.089 Uiso 1 1 d R . .
H5C H 0.3095 0.1650 0.3071 0.089 Uiso 1 1 d 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
P1 0.02499(16) 0.02482(17) 0.03056(18) 0.000 0.000 -0.00052(19)
C6 0.0314(5) 0.0285(5) 0.0319(6) 0.0027(5) 0.0017(5) -0.0014(4)
C7 0.0429(7) 0.0586(10) 0.0538(10) 0.0192(9) -0.0108(7) -0.0082(7)
C8 0.0752(11) 0.0581(9) 0.0424(8) 0.0174(7) -0.0134(11) 0.0065(11)
C9 0.0831(13) 0.0389(8) 0.0318(7) 0.0039(7) 0.0117(8) -0.0100(8)
C10 0.0487(8) 0.0524(9) 0.0594(10) 0.0135(9) 0.0103(8) -0.0145(7)
C11 0.0320(6) 0.0411(7) 0.0498(8) 0.0087(7) 0.0021(6) -0.0024(5)
C12 0.0268(5) 0.0272(5) 0.0314(6) 0.0015(5) -0.0009(4) 0.0004(4)
C13 0.0513(8) 0.0295(6) 0.0577(9) -0.0067(6) -0.0166(7) 0.0064(6)
C14 0.0611(10) 0.0399(8) 0.0766(13) 0.0001(9) -0.0239(10) 0.0172(7)
C15 0.0359(6) 0.0628(10) 0.0442(8) 0.0052(8) -0.0064(6) 0.0097(6)
C16 0.0411(6) 0.0550(9) 0.0403(7) -0.0110(9) -0.0079(5) 0.0009(7)
C17 0.0456(7) 0.0338(6) 0.0450(7) -0.0072(6) -0.0088(6) 0.0046(6)
Co1 0.02424(9) 0.02942(10) 0.01606(8) 0.000 0.000 -0.00128(9)
O1 0.0269(4) 0.0569(6) 0.0208(4) -0.0059(4) -0.0015(3) -0.0040(4)
O2 0.0371(5) 0.0760(9) 0.0426(6) -0.0127(6) -0.0123(5) -0.0093(5)
O3 0.0353(4) 0.0299(4) 0.0334(4) 0.0066(4) 0.0015(4) -0.0002(3)
O4 0.0515(6) 0.0423(6) 0.0568(7) 0.0042(5) 0.0035(6) 0.0168(5)
N1 0.0324(4) 0.0276(5) 0.0220(4) 0.0007(4) 0.0046(4) -0.0030(4)
C1 0.0301(5) 0.0384(7) 0.0292(6) 0.0016(5) -0.0064(5) -0.0023(5)
C2 0.0251(5) 0.0466(8) 0.0405(7) 0.0007(6) 0.0025(5) -0.0036(4)
C3 0.0306(5) 0.0388(6) 0.0278(6) -0.0007(5) 0.0081(5) 0.0016(5)
C4 0.0389(6) 0.0331(6) 0.0281(6) -0.0017(5) 0.0004(5) 0.0037(5)
C5 0.0486(7) 0.0403(8) 0.0188(5) -0.0012(6) 0.0050(4) -0.0021(6)
O5 0.0607(7) 0.0651(8) 0.0530(7) 0.0121(7) 0.0107(6) 0.0099(7)

_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
P1 C6 1.7836(13) 2 ?
P1 C6 1.7836(13) . ?
P1 C12 1.7874(13) . ?
P1 C12 1.7874(13) 2 ?
C6 C11 1.3768(18) . ?
C6 C7 1.391(2) . ?
C7 C8 1.374(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.367(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.355(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.392(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.376(2) . ?
C12 C17 1.389(2) . ?
C13 C14 1.390(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.367(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
Co1 O3 1.9027(9) . ?
Co1 O3 1.9027(9) 2_565 ?
Co1 N1 1.9125(10) . ?
Co1 N1 1.9125(10) 2_565 ?
Co1 O1 1.9140(8) . ?
Co1 O1 1.9140(8) 2_565 ?
O1 C1 1.2777(15) . ?
O2 C1 1.2240(16) . ?
O3 C4 1.2859(16) . ?
O4 C4 1.2191(17) . ?
N1 C3 1.4769(17) . ?
N1 C5 1.4886(17) . ?
N1 H1A 0.8062 . ?
C1 C2 1.5243(19) . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9800 . ?
C5 C5 1.504(3) 2_565 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O5 H5D 0.8509 . ?
O5 H5C 0.8560 . ?

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
C6 P1 C6 106.32(9) 2 . ?
C6 P1 C12 111.38(6) 2 . ?
C6 P1 C12 111.22(6) . . ?
C6 P1 C12 111.22(6) 2 2 ?
C6 P1 C12 111.38(6) . 2 ?
C12 P1 C12 105.43(8) . 2 ?
C11 C6 C7 119.35(13) . . ?
C11 C6 P1 121.28(11) . . ?
C7 C6 P1 119.17(10) . . ?
C8 C7 C6 120.27(16) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.99(17) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C10 C9 C8 120.31(15) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.81(15) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C6 C11 C10 119.21(15) . . ?
C6 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C13 C12 C17 120.12(13) . . ?
C13 C12 P1 121.97(10) . . ?
C17 C12 P1 117.71(10) . . ?
C12 C13 C14 119.11(15) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 120.42(15) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 C14 120.48(14) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 119.96(15) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C12 119.91(14) . . ?
C16 C17 H17A 120.0 . . ?
C12 C17 H17A 120.0 . . ?
O3 Co1 O3 177.40(6) . 2_565 ?
O3 Co1 N1 83.18(4) . . ?
O3 Co1 N1 94.95(4) 2_565 . ?
O3 Co1 N1 94.95(4) . 2_565 ?
O3 Co1 N1 83.18(4) 2_565 2_565 ?
N1 Co1 N1 88.44(6) . 2_565 ?
O3 Co1 O1 92.45(4) . . ?
O3 Co1 O1 89.43(4) 2_565 . ?
N1 Co1 O1 92.65(4) . . ?
N1 Co1 O1 172.60(4) 2_565 . ?
O3 Co1 O1 89.43(4) . 2_565 ?
O3 Co1 O1 92.45(4) 2_565 2_565 ?
N1 Co1 O1 172.60(4) . 2_565 ?
N1 Co1 O1 92.65(4) 2_565 2_565 ?
O1 Co1 O1 87.21(5) . 2_565 ?
C1 O1 Co1 129.62(9) . . ?
C4 O3 Co1 112.22(8) . . ?
C3 N1 C5 112.55(10) . . ?
C3 N1 Co1 104.27(7) . . ?
C5 N1 Co1 108.18(8) . . ?
C3 N1 H1A 105.8 . . ?
C5 N1 H1A 112.1 . . ?
Co1 N1 H1A 113.8 . . ?
O2 C1 O1 122.76(13) . . ?
O2 C1 C2 117.33(11) . . ?
O1 C1 C2 119.90(11) . . ?
C3 C2 C1 115.85(10) . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
N1 C3 C2 110.04(11) . . ?
N1 C3 C4 107.12(10) . . ?
C2 C3 C4 110.34(11) . . ?
N1 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O4 C4 O3 124.94(14) . . ?
O4 C4 C3 120.59(12) . . ?
O3 C4 C3 114.44(11) . . ?
N1 C5 C5 107.25(9) . 2_565 ?
N1 C5 H5A 110.3 . . ?
C5 C5 H5A 110.3 2_565 . ?
N1 C5 H5B 110.3 . . ?
C5 C5 H5B 110.3 2_565 . ?
H5A C5 H5B 108.5 . . ?
H5D O5 H5C 101.3 . . ?

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
N1 H1A O5 0.81 2.36 3.0409(17) 142.2 4
O5 H5D O4 0.85 2.16 3.0035(16) 168.7 .
O5 H5C O2 0.86 1.99 2.8269(18) 167.2 4_546
C2 H2A O5 0.97 2.68 3.431(2) 135.0 4
C13 H13A O5 0.93 2.71 3.307(2) 123.1 4_546
C5 H5B O1 0.97 2.56 3.3934(15) 144.6 1_554
C5 H5B O2 0.97 2.72 3.6545(19) 162.4 1_554

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        32.83
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051

# Attachment 'compound_4.cif'

data_sh1
_database_code_depnum_ccdc_archive 'CCDC 755826'
#TrackingRef 'compound_4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 Fe N3 O8'
_chemical_formula_weight         362.11

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P6(1)22

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'
'-y, -x, -z+5/6'
'x-y, -y, -z'
'x, x-y, -z+1/6'
'y, x, -z+1/3'
'-x+y, y, -z+1/2'
'-x, -x+y, -z+2/3'

_cell_length_a                   9.504(4)
_cell_length_b                   9.504(4)
_cell_length_c                   27.012(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2113.0(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7728
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1122
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  0.7305
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
The temperature of the crystal was controlled using the Oxford
Cryosystem Cryostream Cooler (Cosier & Glazer, 1986).
The data collection nominally covered over a hemisphere of
Reciprocal space, by a combination of three sets of exposures with
different \f angles for the crystal; each 10 s exposure covered
0.3\% in \w.
The crystal-to-detector distance was 5.0 cm. Coverage of the unique
Set is over 97% complete to at least 26\% in \q.
Crystal decay was found to be negligible by by repeating the initial
frames at the end of data collection and analyzing the duplicate
reflections.

Hydrogen atoms were added at calculated positions and refined using
a riding model. Anisotropic displacement parameters were used for all
non-H atoms; H-atoms were given isotropic displacement parameter equal
to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic
displacement parameter of the atom to which they are attached.
;

_diffrn_ambient_temperature      298(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  'Siemens SMART diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            20245
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         29.09
_reflns_number_total             1835
_reflns_number_gt                1467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1994)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (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^)+(0.0563P)^2^+0.2500P] 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), 647 Friedel pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration rmad
_reflns_Friedel_coverage         647
_refine_ls_number_reflns         1835
_refine_ls_number_parameters     107
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.091
_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
Fe1 Fe 1.28932(4) 0.57864(7) 0.2500 0.03748(17) Uani 1 2 d S . .
O1 O 1.2013(3) 0.7162(3) 0.22994(8) 0.0502(5) Uani 1 1 d . . .
N01 N 0.7222(5) 0.7222(5) 0.1667 0.0666(11) Uani 1 2 d SDU . .
H01 H 0.821(2) 0.741(3) 0.1797(13) 0.100 Uiso 1 1 d D . .
H02 H 0.650(3) 0.696(3) 0.1911(8) 0.100 Uiso 1 1 d D . .
O2 O 1.0267(3) 0.7813(3) 0.20078(10) 0.0651(7) Uani 1 1 d . . .
C2 C 1.0848(4) 0.6918(4) 0.20048(11) 0.0456(7) Uani 1 1 d . . .
C3 C 1.0182(4) 0.5510(4) 0.16363(11) 0.0494(8) Uani 1 1 d . . .
H3A H 0.9010 0.4906 0.1671 0.059 Uiso 1 1 calc R . .
H3B H 1.0418 0.5969 0.1305 0.059 Uiso 1 1 calc R . .
C4 C 1.0793(4) 0.4309(4) 0.16715(10) 0.0454(7) Uani 1 1 d . . .
H4A H 1.0085 0.3353 0.1471 0.054 Uiso 1 1 calc R . .
N5 N 1.0740(3) 0.3789(3) 0.21864(8) 0.0424(6) Uani 1 1 d . . .
H5 H 0.9923 0.3778 0.2315 0.051 Uiso 1 1 d R . .
C6 C 1.0804(4) 0.2268(4) 0.22440(11) 0.0506(8) Uani 1 1 d . . .
H6A H 1.1505 0.2213 0.1993 0.061 Uiso 1 1 calc R . .
H6B H 0.9726 0.1332 0.2206 0.061 Uiso 1 1 calc R . .
O7 O 1.3661(3) 0.5689(3) 0.18166(7) 0.0509(6) Uani 1 1 d . . .
C7 C 1.2535(4) 0.5025(4) 0.14847(11) 0.0465(7) Uani 1 1 d . . .
O8 O 1.2800(3) 0.4934(3) 0.10433(7) 0.0612(7) 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
Fe1 0.0341(2) 0.0421(3) 0.0389(3) 0.000 -0.0012(2) 0.02104(17)
O1 0.0497(13) 0.0526(13) 0.0601(12) -0.0059(10) -0.0162(10) 0.0343(11)
N01 0.0446(16) 0.0446(16) 0.115(3) 0.0076(11) -0.0076(11) 0.0252(19)
O2 0.0525(15) 0.0708(17) 0.0883(17) -0.0122(14) -0.0196(13) 0.0430(14)
C2 0.0345(15) 0.056(2) 0.0496(15) 0.0025(13) 0.0011(12) 0.0254(14)
C3 0.0436(17) 0.064(2) 0.0435(14) -0.0042(15) -0.0074(13) 0.0287(17)
C4 0.0462(17) 0.0500(17) 0.0373(13) -0.0061(14) -0.0066(14) 0.0220(14)
N5 0.0427(14) 0.0454(15) 0.0359(11) -0.0024(10) 0.0031(9) 0.0197(11)
C6 0.055(2) 0.0488(18) 0.0441(14) -0.0033(13) 0.0002(14) 0.0225(15)
O7 0.0441(13) 0.0682(15) 0.0443(11) 0.0062(9) 0.0082(9) 0.0310(12)
C7 0.064(2) 0.0472(16) 0.0403(14) 0.0042(12) 0.0047(13) 0.0370(17)
O8 0.094(2) 0.0752(16) 0.0377(10) 0.0072(10) 0.0142(11) 0.0601(16)

_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 O1 1.948(2) 11_755 ?
Fe1 O1 1.948(2) . ?
Fe1 O7 2.004(2) . ?
Fe1 O7 2.004(2) 11_755 ?
Fe1 N5 2.151(3) . ?
Fe1 N5 2.151(3) 11_755 ?
O1 C2 1.287(4) . ?
N01 H01 0.932(14) . ?
N01 H02 0.890(13) . ?
O2 C2 1.224(4) . ?
C2 C3 1.528(4) . ?
C3 C4 1.520(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N5 1.468(4) . ?
C4 C7 1.528(5) . ?
C4 H4A 0.9800 . ?
N5 C6 1.486(4) . ?
N5 H5 0.8462 . ?
C6 C6 1.518(6) 11_755 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C7 1.293(4) . ?
C7 O8 1.231(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
O1 Fe1 O1 108.95(14) 11_755 . ?
O1 Fe1 O7 89.03(10) 11_755 . ?
O1 Fe1 O7 93.64(9) . . ?
O1 Fe1 O7 93.64(10) 11_755 11_755 ?
O1 Fe1 O7 89.03(10) . 11_755 ?
O7 Fe1 O7 175.39(14) . 11_755 ?
O1 Fe1 N5 160.75(10) 11_755 . ?
O1 Fe1 N5 86.80(10) . . ?
O7 Fe1 N5 78.71(9) . . ?
O7 Fe1 N5 97.72(10) 11_755 . ?
O1 Fe1 N5 86.80(10) 11_755 11_755 ?
O1 Fe1 N5 160.75(10) . 11_755 ?
O7 Fe1 N5 97.72(9) . 11_755 ?
O7 Fe1 N5 78.71(9) 11_755 11_755 ?
N5 Fe1 N5 80.29(14) . 11_755 ?
C2 O1 Fe1 132.1(2) . . ?
H01 N01 H02 109.3(13) . . ?
O2 C2 O1 121.2(3) . . ?
O2 C2 C3 118.6(3) . . ?
O1 C2 C3 120.2(3) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3A 107.8 . . ?
C2 C3 H3A 107.8 . . ?
C4 C3 H3B 107.8 . . ?
C2 C3 H3B 107.8 . . ?
H3A C3 H3B 107.1 . . ?
N5 C4 C3 110.5(2) . . ?
N5 C4 C7 108.0(2) . . ?
C3 C4 C7 112.4(3) . . ?
N5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C7 C4 H4A 108.6 . . ?
C4 N5 C6 114.6(2) . . ?
C4 N5 Fe1 102.64(17) . . ?
C6 N5 Fe1 109.5(2) . . ?
C4 N5 H5 105.7 . . ?
C6 N5 H5 115.4 . . ?
Fe1 N5 H5 108.1 . . ?
N5 C6 C6 108.25(19) . 11_755 ?
N5 C6 H6A 110.0 . . ?
C6 C6 H6A 110.0 11_755 . ?
N5 C6 H6B 110.0 . . ?
C6 C6 H6B 110.0 11_755 . ?
H6A C6 H6B 108.4 . . ?
C7 O7 Fe1 115.4(2) . . ?
O8 C7 O7 123.9(3) . . ?
O8 C7 C4 120.2(3) . . ?
O7 C7 C4 115.9(2) . . ?

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
N01 H01 O2 0.932(14) 1.883(14) 2.813(4) 175(3) .
N01 H02 O7 0.890(13) 2.36(3) 2.968(4) 126(2) 1_455
N5 H5 O8 0.85 2.00 2.788(3) 154.4 2_545
N01 H02 O1 0.890(13) 2.549(10) 3.402(3) 161(2) 11_655

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.052

# Attachment 'compound_5.cif'

data_nc4
_database_code_depnum_ccdc_archive 'CCDC 755827'
#TrackingRef 'compound_5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H36 Fe N2 O10 P'
_chemical_formula_weight         719.47

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'
P P 0.1023 0.0942 '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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   12.8761(3)
_cell_length_b                   17.2456(4)
_cell_length_c                   7.4186(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1647.35(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4616
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             750
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'

_exptl_special_details           
;
A crystal was mounted on a glass fibre using Araldite and the
data recorded at room temperature.
The data collection nominally covered over a hemisphere of
Reciprocal space, by a combination of eight sets of exposures with
different \f angles for the crystal; each 10 s exposure covered
0.3\% in \w.
The crystal-to-detector distance was 5.5 cm.
Crystal decay was found to be negligible by by repeating the initial
frames at the end of data collection and analyzing the duplicate
reflections.

Hydrogen atoms were added at calculated positions and refined using
a riding model except the N and OHs which were located in a difference
map. Anisotropic displacement parameters were used for all
non-H atoms; H-atoms were given isotropic displacement parameter equal
to 1.2 (or 1.5 for N and OH H-atoms) times the equivalent
isotropic displacement parameter of the atom to which they are attached.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            9632
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         29.21
_reflns_number_total             3843
_reflns_number_gt                2853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (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^)+(0.0341P)^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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 1500 Friedel pairs'
_refine_ls_abs_structure_Flack   0.011(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.925
_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
Fe1 Fe 0.5000 0.5000 0.16973(5) 0.03401(11) Uani 1 2 d S . .
O1 O 0.54619(12) 0.41857(8) 0.3323(2) 0.0501(4) Uani 1 1 d . . .
C1 C 0.55393(16) 0.34437(13) 0.3183(3) 0.0426(5) Uani 1 1 d . . .
O2 O 0.59159(16) 0.30448(10) 0.4356(2) 0.0695(5) Uani 1 1 d . . .
C2 C 0.51827(18) 0.30490(11) 0.1462(3) 0.0474(6) Uani 1 1 d . . .
H2A H 0.4756 0.2609 0.1800 0.057 Uiso 1 1 calc R . .
H2B H 0.5793 0.2845 0.0860 0.057 Uiso 1 1 calc R . .
C3 C 0.45761(16) 0.35273(12) 0.0096(3) 0.0408(5) Uani 1 1 d . . .
H3A H 0.4407 0.3204 -0.0950 0.049 Uiso 1 1 calc R . .
C4 C 0.35696(18) 0.38236(14) 0.0964(3) 0.0437(5) Uani 1 1 d U . .
O3 O 0.35770(11) 0.45426(9) 0.1435(2) 0.0448(4) Uani 1 1 d U . .
O4 O 0.28517(13) 0.33699(10) 0.1217(2) 0.0612(5) Uani 1 1 d . . .
N1 N 0.51953(14) 0.41998(10) -0.0493(2) 0.0365(4) Uani 1 1 d . . .
H1 H 0.5797(19) 0.4048(14) -0.069(3) 0.055 Uiso 1 1 d . . .
C5 C 0.48225(18) 0.45852(12) -0.2157(3) 0.0444(6) Uani 1 1 d . . .
H5A H 0.4070 0.4564 -0.2209 0.053 Uiso 1 1 calc R . .
H5B H 0.5096 0.4320 -0.3207 0.053 Uiso 1 1 calc R . .
P1 P 0.5000 0.0000 0.06510(9) 0.03144(16) Uani 1 2 d S . .
C6 C 0.39651(15) -0.03057(12) 0.2102(3) 0.0354(5) Uani 1 1 d . . .
C7 C 0.35697(19) 0.02121(14) 0.3359(4) 0.0592(7) Uani 1 1 d . . .
H7A H 0.3807 0.0721 0.3380 0.071 Uiso 1 1 calc R . .
C8 C 0.28286(19) -0.0025(2) 0.4574(3) 0.0641(7) Uani 1 1 d . . .
H8A H 0.2554 0.0325 0.5400 0.077 Uiso 1 1 calc R . .
C9 C 0.24970(18) -0.07772(19) 0.4562(3) 0.0584(7) Uani 1 1 d . . .
H9A H 0.2001 -0.0940 0.5392 0.070 Uiso 1 1 calc R . .
C10 C 0.28823(18) -0.12860(15) 0.3356(4) 0.0585(7) Uani 1 1 d . . .
H10A H 0.2650 -0.1796 0.3366 0.070 Uiso 1 1 calc R . .
C11 C 0.36181(16) -0.10604(13) 0.2104(3) 0.0440(6) Uani 1 1 d . . .
H11A H 0.3876 -0.1415 0.1271 0.053 Uiso 1 1 calc R . .
C12 C 0.45997(14) 0.07726(11) -0.0810(3) 0.0319(5) Uani 1 1 d . . .
C13 C 0.53048(16) 0.10407(13) -0.2060(3) 0.0475(6) Uani 1 1 d . . .
H13A H 0.5977 0.0844 -0.2075 0.057 Uiso 1 1 calc R . .
C14 C 0.5014(2) 0.16011(12) -0.3291(3) 0.0525(5) Uani 1 1 d . . .
H14A H 0.5494 0.1784 -0.4125 0.063 Uiso 1 1 calc R . .
C15 C 0.4037(2) 0.18835(13) -0.3285(4) 0.0552(6) Uani 1 1 d . . .
H15A H 0.3841 0.2257 -0.4124 0.066 Uiso 1 1 calc R . .
C16 C 0.33291(19) 0.16180(16) -0.2035(4) 0.0667(8) Uani 1 1 d . . .
H16A H 0.2659 0.1820 -0.2026 0.080 Uiso 1 1 calc R . .
C17 C 0.36000(18) 0.10589(14) -0.0801(4) 0.0535(6) Uani 1 1 d . . .
H17A H 0.3116 0.0876 0.0027 0.064 Uiso 1 1 calc R . .
O5 O 0.19232(18) 0.18358(13) 0.2184(3) 0.0769(6) Uani 1 1 d . . .
H5C H 0.168(3) 0.186(2) 0.323(6) 0.115 Uiso 1 1 d . . .
H5D H 0.229(3) 0.221(2) 0.217(6) 0.115 Uiso 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
Fe1 0.0478(2) 0.0317(2) 0.02254(19) 0.000 0.000 0.0027(2)
O1 0.0849(11) 0.0316(8) 0.0337(8) 0.0028(7) -0.0102(8) 0.0044(7)
C1 0.0494(12) 0.0407(12) 0.0377(13) 0.0091(11) 0.0005(11) 0.0005(10)
O2 0.1062(15) 0.0474(11) 0.0550(12) 0.0167(9) -0.0181(10) 0.0101(10)
C2 0.0562(15) 0.0304(10) 0.0557(14) -0.0016(10) 0.0016(12) 0.0048(10)
C3 0.0482(12) 0.0403(12) 0.0338(12) -0.0096(10) 0.0000(9) -0.0024(10)
C4 0.0480(13) 0.0495(10) 0.0336(12) 0.0004(10) -0.0013(10) -0.0032(12)
O3 0.0430(8) 0.0455(8) 0.0459(10) -0.0005(8) 0.0120(7) 0.0028(7)
O4 0.0519(9) 0.0638(12) 0.0681(13) -0.0007(10) 0.0066(8) -0.0199(9)
N1 0.0362(10) 0.0452(10) 0.0280(9) -0.0054(7) 0.0002(8) 0.0026(9)
C5 0.0497(15) 0.0600(12) 0.0235(10) -0.0040(9) -0.0031(10) 0.0017(12)
P1 0.0308(3) 0.0307(3) 0.0329(4) 0.000 0.000 -0.0006(4)
C6 0.0340(10) 0.0405(12) 0.0317(12) 0.0032(9) 0.0005(9) 0.0001(9)
C7 0.0663(15) 0.0533(16) 0.0581(16) -0.0154(13) 0.0204(14) -0.0135(12)
C8 0.0629(14) 0.0828(18) 0.0467(14) -0.0207(19) 0.0153(11) -0.002(2)
C9 0.0420(14) 0.094(2) 0.0394(15) 0.0189(15) 0.0057(11) -0.0068(14)
C10 0.0545(15) 0.0523(15) 0.0687(18) 0.0124(15) 0.0112(14) -0.0103(12)
C11 0.0427(12) 0.0392(12) 0.0501(14) 0.0034(11) 0.0089(11) 0.0013(10)
C12 0.0332(10) 0.0301(10) 0.0326(11) -0.0021(9) -0.0018(9) 0.0009(9)
C13 0.0406(13) 0.0536(14) 0.0482(14) 0.0093(12) 0.0101(10) 0.0108(10)
C14 0.0647(14) 0.0493(12) 0.0436(12) 0.0084(10) 0.0161(16) 0.0040(14)
C15 0.0743(17) 0.0401(13) 0.0511(16) 0.0064(12) -0.0103(14) 0.0104(13)
C16 0.0451(14) 0.0686(18) 0.086(2) 0.0242(16) -0.0030(14) 0.0198(13)
C17 0.0362(12) 0.0551(15) 0.0692(17) 0.0161(14) 0.0064(12) 0.0069(11)
O5 0.0862(15) 0.0726(14) 0.0719(15) -0.0156(12) 0.0138(11) -0.0130(11)

_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 O1 1.9442(14) 2_665 ?
Fe1 O1 1.9442(14) . ?
Fe1 O3 2.0043(14) . ?
Fe1 O3 2.0043(14) 2_665 ?
Fe1 N1 2.1467(17) . ?
Fe1 N1 2.1467(17) 2_665 ?
O1 C1 1.288(3) . ?
C1 O2 1.211(2) . ?
C1 C2 1.518(3) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.474(3) . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9800 . ?
C4 O4 1.226(3) . ?
C4 O3 1.289(3) . ?
N1 C5 1.482(3) . ?
N1 H1 0.83(2) . ?
C5 C5 1.502(4) 2_665 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
P1 C6 1.792(2) 2_655 ?
P1 C6 1.792(2) . ?
P1 C12 1.793(2) . ?
P1 C12 1.793(2) 2_655 ?
C6 C11 1.376(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.375(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.348(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(3) . ?
C12 C17 1.379(3) . ?
C13 C14 1.381(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.349(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
O5 H5C 0.84(4) . ?
O5 H5D 0.80(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
O1 Fe1 O1 103.33(9) 2_665 . ?
O1 Fe1 O3 93.71(6) 2_665 . ?
O1 Fe1 O3 93.18(6) . . ?
O1 Fe1 O3 93.18(6) 2_665 2_665 ?
O1 Fe1 O3 93.71(6) . 2_665 ?
O3 Fe1 O3 168.87(9) . 2_665 ?
O1 Fe1 N1 165.85(7) 2_665 . ?
O1 Fe1 N1 88.25(6) . . ?
O3 Fe1 N1 77.33(6) . . ?
O3 Fe1 N1 94.16(6) 2_665 . ?
O1 Fe1 N1 88.25(6) 2_665 2_665 ?
O1 Fe1 N1 165.85(7) . 2_665 ?
O3 Fe1 N1 94.16(6) . 2_665 ?
O3 Fe1 N1 77.33(6) 2_665 2_665 ?
N1 Fe1 N1 81.60(9) . 2_665 ?
C1 O1 Fe1 133.74(16) . . ?
O2 C1 O1 122.5(2) . . ?
O2 C1 C2 118.11(19) . . ?
O1 C1 C2 119.36(19) . . ?
C1 C2 C3 118.17(17) . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2A 107.8 . . ?
C1 C2 H2B 107.8 . . ?
C3 C2 H2B 107.8 . . ?
H2A C2 H2B 107.1 . . ?
N1 C3 C2 110.26(17) . . ?
N1 C3 C4 108.62(17) . . ?
C2 C3 C4 109.55(19) . . ?
N1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
O4 C4 O3 125.3(2) . . ?
O4 C4 C3 119.3(2) . . ?
O3 C4 C3 115.3(2) . . ?
C4 O3 Fe1 114.32(14) . . ?
C3 N1 C5 115.14(17) . . ?
C3 N1 Fe1 102.59(12) . . ?
C5 N1 Fe1 107.72(13) . . ?
C3 N1 H1 107.9(18) . . ?
C5 N1 H1 107.3(18) . . ?
Fe1 N1 H1 116.4(17) . . ?
N1 C5 C5 109.19(15) . 2_665 ?
N1 C5 H5A 109.8 . . ?
C5 C5 H5A 109.8 2_665 . ?
N1 C5 H5B 109.8 . . ?
C5 C5 H5B 109.8 2_665 . ?
H5A C5 H5B 108.3 . . ?
C6 P1 C6 106.17(14) 2_655 . ?
C6 P1 C12 110.99(9) 2_655 . ?
C6 P1 C12 111.58(9) . . ?
C6 P1 C12 111.58(9) 2_655 2_655 ?
C6 P1 C12 110.99(9) . 2_655 ?
C12 P1 C12 105.63(13) . 2_655 ?
C11 C6 C7 119.3(2) . . ?
C11 C6 P1 121.34(16) . . ?
C7 C6 P1 119.15(16) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C6 C11 C10 119.3(2) . . ?
C6 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C13 C12 C17 119.88(19) . . ?
C13 C12 P1 117.82(15) . . ?
C17 C12 P1 122.12(16) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C12 119.0(2) . . ?
C16 C17 H17A 120.5 . . ?
C12 C17 H17A 120.5 . . ?
H5C O5 H5D 101(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
O5 H5D O4 0.80(4) 2.24(4) 2.991(3) 156(4) .
N1 H1 O5 0.83(2) 2.38(2) 3.117(3) 149(2) 3
O5 H5C O2 0.84(4) 2.05(4) 2.883(3) 173(4) 3_456
C9 H9A O3 0.93 2.60 3.322(3) 134.3 4_546
C14 H14A O2 0.93 2.51 3.255(3) 137.5 1_554
C5 H5B O1 0.97 2.63 3.521(3) 153.3 1_554

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039

# Attachment 'compound_7.cif'

data_nc13
_database_code_depnum_ccdc_archive 'CCDC 755828'
#TrackingRef 'compound_7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H36 Cr N2 O10 P'
_chemical_formula_weight         715.62

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   12.7168(3)
_cell_length_b                   16.9853(5)
_cell_length_c                   7.3700(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1591.91(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4459
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.29

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             746
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'

_exptl_special_details           
;
The temperature of the crystal was controlled using the Oxford
Cryosystem Cryostream Cobra.
The data collection nominally covered over a hemisphere of
Reciprocal space, by a combination of four sets of exposures with
different \f angles for the crystal; each 10 s exposure covered
0.3\% in \w.
The crystal-to-detector distance was 5.5 cm.
Crystal decay was found to be negligible by by repeating the initial
frames at the end of data collection and analyzing the duplicate
reflections.

Hydrogen atoms were added at calculated positions and refined using
a riding model except the NH and OHs which were located in a difference
map. Anisotropic displacement parameters were used for all
non-H atoms; H-atoms were given isotropic displacement parameter equal
to 1.2 (or 1.5 for methyl, NH or OH H-atoms) times the equivalent
isotropic displacement parameter of the atom to which they are attached.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         "Enhance (Mo) X-ray Source'"
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            6946
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         29.36
_reflns_number_total             3713
_reflns_number_gt                3292
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (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^)+(0.0361P)^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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 1482 Friedel pairs'
_refine_ls_abs_structure_Flack   0.020(17)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     227
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.992
_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
Cr1 Cr 0.5000 0.5000 0.64953(5) 0.00986(10) Uani 1 2 d S . .
O1 O 0.45593(10) 0.57834(7) 0.82958(16) 0.0147(3) Uani 1 1 d . . .
O2 O 0.40348(11) 0.69347(8) 0.93849(18) 0.0206(3) Uani 1 1 d . . .
C1 C 0.44347(13) 0.65384(12) 0.8177(3) 0.0143(4) Uani 1 1 d . . .
C2 C 0.47783(13) 0.69650(11) 0.6441(2) 0.0144(4) Uani 1 1 d . . .
H2A H 0.4140 0.7174 0.5842 0.017 Uiso 1 1 calc R . .
H2B H 0.5213 0.7423 0.6799 0.017 Uiso 1 1 calc R . .
C3 C 0.53939(13) 0.64925(11) 0.5038(2) 0.0125(4) Uani 1 1 d . . .
H3A H 0.5554 0.6831 0.3963 0.015 Uiso 1 1 calc R . .
O3 O 0.71507(9) 0.66589(8) 0.61442(18) 0.0184(3) Uani 1 1 d . . .
C4 C 0.64220(15) 0.61965(12) 0.5890(2) 0.0138(4) Uani 1 1 d . . .
O4 O 0.64246(9) 0.54619(7) 0.63481(18) 0.0138(3) Uani 1 1 d . . .
N1 N 0.47725(11) 0.57994(10) 0.44622(19) 0.0114(3) Uani 1 1 d D . .
H1 H 0.4143(13) 0.5943(12) 0.423(3) 0.017 Uiso 1 1 d D . .
C5 C 0.51613(14) 0.54281(11) 0.2751(2) 0.0135(4) Uani 1 1 d . . .
H5A H 0.5937 0.5471 0.2680 0.016 Uiso 1 1 calc R . .
H5B H 0.4855 0.5700 0.1686 0.016 Uiso 1 1 calc R . .
P1 P 0.0000 0.5000 0.43012(8) 0.01093(13) Uani 1 2 d S . .
C6 C -0.10579(14) 0.52893(11) 0.2836(2) 0.0129(4) Uani 1 1 d . . .
C7 C -0.14478(15) 0.47443(12) 0.1588(3) 0.0201(4) Uani 1 1 d . . .
H7A H -0.1194 0.4218 0.1590 0.024 Uiso 1 1 calc R . .
C8 C -0.22041(14) 0.49731(16) 0.0351(2) 0.0219(4) Uani 1 1 d . . .
H8A H -0.2480 0.4601 -0.0487 0.026 Uiso 1 1 calc R . .
C9 C -0.25596(14) 0.57423(13) 0.0328(3) 0.0189(5) Uani 1 1 d . . .
H9A H -0.3070 0.5901 -0.0539 0.023 Uiso 1 1 calc R . .
C10 C -0.21737(14) 0.62808(11) 0.1565(3) 0.0182(4) Uani 1 1 d . . .
C11 C -0.14276(14) 0.60567(12) 0.2831(3) 0.0148(4) Uani 1 1 d . . .
H11A H -0.1171 0.6426 0.3691 0.018 Uiso 1 1 calc R . .
C12 C 0.03707(13) 0.57889(11) 0.5781(2) 0.0120(4) Uani 1 1 d . . .
C13 C -0.03684(14) 0.60512(12) 0.7027(2) 0.0156(4) Uani 1 1 d . . .
H13A H -0.1062 0.5844 0.7005 0.019 Uiso 1 1 calc R . .
C14 C -0.00980(15) 0.66142(11) 0.8300(2) 0.0172(4) Uani 1 1 d . . .
H14A H -0.0605 0.6796 0.9150 0.021 Uiso 1 1 calc R . .
C15 C 0.09178(15) 0.69113(11) 0.8329(3) 0.0175(4) Uani 1 1 d . . .
H15A H 0.1109 0.7293 0.9212 0.021 Uiso 1 1 calc R . .
C16 C 0.16545(14) 0.66560(12) 0.7081(3) 0.0205(4) Uani 1 1 d . . .
H16A H 0.2346 0.6868 0.7105 0.025 Uiso 1 1 calc R . .
H10A H -0.2427 0.6807 0.1544 0.025 Uiso 1 1 d R . .
C17 C 0.13918(15) 0.60917(12) 0.5791(3) 0.0174(4) Uani 1 1 d . . .
H17A H 0.1897 0.5915 0.4934 0.021 Uiso 1 1 calc R . .
O5 O 0.80686(11) 0.81990(9) 0.7163(2) 0.0215(3) Uani 1 1 d D . .
H5C H 0.8320(17) 0.8133(14) 0.822(2) 0.032 Uiso 1 1 d D . .
H5D H 0.7790(17) 0.7778(11) 0.693(3) 0.032 Uiso 1 1 d 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
Cr1 0.01332(18) 0.0084(2) 0.00786(17) 0.000 0.000 0.00024(18)
O1 0.0226(6) 0.0100(7) 0.0113(6) -0.0011(5) 0.0009(5) 0.0020(5)
O2 0.0291(7) 0.0152(8) 0.0176(7) -0.0045(6) 0.0041(6) 0.0034(6)
C1 0.0143(8) 0.0134(10) 0.0153(9) -0.0039(8) -0.0035(8) 0.0009(7)
C2 0.0174(9) 0.0071(9) 0.0187(8) 0.0020(8) -0.0019(8) 0.0011(7)
C3 0.0155(8) 0.0101(10) 0.0120(8) 0.0018(8) 0.0005(7) -0.0015(7)
O3 0.0170(6) 0.0164(8) 0.0217(7) -0.0004(6) -0.0010(6) -0.0050(6)
C4 0.0159(8) 0.0160(11) 0.0095(8) -0.0011(7) 0.0027(8) -0.0002(8)
O4 0.0146(6) 0.0112(7) 0.0156(6) 0.0003(6) -0.0015(6) 0.0000(5)
N1 0.0116(8) 0.0122(8) 0.0106(7) 0.0005(6) -0.0006(6) 0.0006(6)
C5 0.0154(9) 0.0167(10) 0.0083(7) -0.0008(7) 0.0014(8) -0.0006(8)
P1 0.0110(3) 0.0100(3) 0.0118(3) 0.000 0.000 0.0009(3)
C6 0.0115(8) 0.0150(10) 0.0122(8) 0.0014(7) 0.0001(8) 0.0014(7)
C7 0.0219(9) 0.0173(10) 0.0212(10) -0.0042(8) -0.0012(9) 0.0034(8)
C8 0.0223(9) 0.0272(12) 0.0163(9) -0.0082(11) -0.0038(8) -0.0015(11)
C9 0.0136(9) 0.0275(13) 0.0157(10) 0.0061(9) 0.0003(8) 0.0028(8)
C10 0.0183(9) 0.0147(10) 0.0215(10) 0.0042(9) -0.0020(9) 0.0036(8)
C11 0.0133(8) 0.0136(10) 0.0176(9) -0.0003(8) 0.0011(8) -0.0012(7)
C12 0.0128(8) 0.0112(10) 0.0120(8) 0.0013(8) -0.0023(7) -0.0007(7)
C13 0.0130(8) 0.0169(11) 0.0170(9) 0.0001(8) 0.0016(8) -0.0025(7)
C14 0.0206(9) 0.0150(10) 0.0160(8) 0.0001(7) 0.0051(10) 0.0003(8)
C15 0.0251(10) 0.0112(10) 0.0162(9) -0.0010(8) -0.0045(9) -0.0024(8)
C16 0.0135(9) 0.0197(11) 0.0282(11) -0.0034(9) -0.0016(9) -0.0046(8)
C17 0.0128(8) 0.0171(11) 0.0223(10) -0.0021(8) 0.0032(8) -0.0001(8)
O5 0.0264(7) 0.0183(8) 0.0200(7) 0.0025(7) -0.0054(6) -0.0049(6)

_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
Cr1 O1 1.9610(12) 2_665 ?
Cr1 O1 1.9610(12) . ?
Cr1 O4 1.9771(12) . ?
Cr1 O4 1.9771(12) 2_665 ?
Cr1 N1 2.0426(15) 2_665 ?
Cr1 N1 2.0426(15) . ?
O1 C1 1.295(2) . ?
O2 C1 1.227(2) . ?
C1 C2 1.534(3) . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.480(2) . ?
C3 C4 1.535(3) . ?
C3 H3A 1.0000 . ?
O3 C4 1.229(2) . ?
C4 O4 1.293(2) . ?
N1 C5 1.495(2) . ?
N1 H1 0.855(15) . ?
C5 C5 1.511(4) 2_665 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
P1 C12 1.7907(19) . ?
P1 C12 1.7907(19) 2_565 ?
P1 C6 1.7938(18) 2_565 ?
P1 C6 1.7938(18) . ?
C6 C11 1.386(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.381(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9501 . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(3) . ?
C12 C17 1.397(3) . ?
C13 C14 1.383(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
O5 H5C 0.846(16) . ?
O5 H5D 0.816(16) . ?

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 Cr1 O1 94.83(7) 2_665 . ?
O1 Cr1 O4 92.55(5) 2_665 . ?
O1 Cr1 O4 91.71(5) . . ?
O1 Cr1 O4 91.71(5) 2_665 2_665 ?
O1 Cr1 O4 92.55(5) . 2_665 ?
O4 Cr1 O4 173.71(8) . 2_665 ?
O1 Cr1 N1 90.28(5) 2_665 2_665 ?
O1 Cr1 N1 171.08(5) . 2_665 ?
O4 Cr1 N1 95.38(6) . 2_665 ?
O4 Cr1 N1 79.97(6) 2_665 2_665 ?
O1 Cr1 N1 171.08(5) 2_665 . ?
O1 Cr1 N1 90.28(5) . . ?
O4 Cr1 N1 79.97(6) . . ?
O4 Cr1 N1 95.38(6) 2_665 . ?
N1 Cr1 N1 85.63(9) 2_665 . ?
C1 O1 Cr1 131.37(12) . . ?
O2 C1 O1 123.02(17) . . ?
O2 C1 C2 117.66(17) . . ?
O1 C1 C2 119.31(16) . . ?
C3 C2 C1 117.58(15) . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
N1 C3 C2 109.81(14) . . ?
N1 C3 C4 108.15(15) . . ?
C2 C3 C4 109.41(15) . . ?
N1 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O3 C4 O4 125.10(17) . . ?
O3 C4 C3 119.69(17) . . ?
O4 C4 C3 115.16(16) . . ?
C4 O4 Cr1 113.27(11) . . ?
C3 N1 C5 113.64(14) . . ?
C3 N1 Cr1 104.06(10) . . ?
C5 N1 Cr1 106.96(11) . . ?
C3 N1 H1 109.4(14) . . ?
C5 N1 H1 104.9(14) . . ?
Cr1 N1 H1 118.2(14) . . ?
N1 C5 C5 108.44(12) . 2_665 ?
N1 C5 H5A 110.0 . . ?
C5 C5 H5A 110.0 2_665 . ?
N1 C5 H5B 110.0 . . ?
C5 C5 H5B 110.0 2_665 . ?
H5A C5 H5B 108.4 . . ?
C12 P1 C12 104.98(12) . 2_565 ?
C12 P1 C6 111.97(8) . 2_565 ?
C12 P1 C6 111.04(8) 2_565 2_565 ?
C12 P1 C6 111.04(8) . . ?
C12 P1 C6 111.97(8) 2_565 . ?
C6 P1 C6 105.97(12) 2_565 . ?
C11 C6 C7 120.12(17) . . ?
C11 C6 P1 120.91(14) . . ?
C7 C6 P1 118.77(14) . . ?
C8 C7 C6 119.71(19) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C9 120.09(19) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 120.12(18) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.41(18) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 120.1 . . ?
C10 C11 C6 119.52(18) . . ?
C10 C11 H11A 120.2 . . ?
C6 C11 H11A 120.2 . . ?
C13 C12 C17 120.51(17) . . ?
C13 C12 P1 117.71(13) . . ?
C17 C12 P1 121.58(14) . . ?
C14 C13 C12 120.18(17) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 119.56(17) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C16 C15 C14 120.45(18) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 120.54(17) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C12 118.75(17) . . ?
C16 C17 H17A 120.6 . . ?
C12 C17 H17A 120.6 . . ?
H5C O5 H5D 104(2) . . ?

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
N1 H1 O5 0.855(15) 2.245(17) 3.004(2) 148.1(19) 3_466
O5 H5C O2 0.846(16) 1.992(16) 2.834(2) 174(2) 3_567
O5 H5D O3 0.816(16) 2.147(16) 2.961(2) 175(2) .

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.053