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

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#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  data retrieval see:
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data_szg205

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 Fe N2 O16 P4'
_chemical_formula_weight         732.17

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           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                   15.0205(16)
_cell_length_b                   8.6335(10)
_cell_length_c                   10.1078(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.430(2)
_cell_angle_gamma                90.00
_cell_volume                     1304.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3385
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.16

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7533
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   sadabs

_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  'Smart Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7103
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2697
_reflns_number_gt                2345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+2.7190P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Fe1 Fe 1.0000 0.0000 0.0000 0.01371(18) Uani 1 2 d S . .
P1 P 1.03590(5) 0.30709(9) 0.21282(7) 0.0147(2) Uani 1 1 d . . .
P2 P 0.79204(5) 0.12399(10) 0.06481(8) 0.0192(2) Uani 1 1 d . . .
N1 N 0.85924(17) 0.4158(3) 0.1826(3) 0.0176(5) Uani 1 1 d . . .
O1 O 1.03922(15) 0.1432(2) 0.1623(2) 0.0211(5) Uani 1 1 d . . .
O2 O 1.11993(15) 0.3983(3) 0.1723(2) 0.0254(5) Uani 1 1 d . . .
H2A H 1.1540 0.4198 0.2419 0.038 Uiso 1 1 d R . .
O4 O 0.86809(15) 0.1003(3) -0.0171(2) 0.0222(5) Uani 1 1 d . . .
O5 O 0.71264(16) 0.1979(3) -0.0261(2) 0.0256(5) Uani 1 1 d . . .
H5C H 0.6681 0.2100 0.0189 0.038 Uiso 1 1 d R . .
O6 O 0.75958(16) -0.0158(3) 0.1376(3) 0.0260(5) Uani 1 1 d . . .
H6C H 0.7957 -0.0344 0.2056 0.031 Uiso 1 1 d R . .
O7 O 0.44806(19) 0.6474(4) 0.4451(3) 0.0404(7) Uani 1 1 d . . .
O8 O 0.3963(2) 0.4990(5) 0.2745(4) 0.0646(12) Uani 1 1 d . . .
H8B H 0.3482 0.5050 0.3124 0.097 Uiso 1 1 d R . .
C2 C 0.8199(2) 0.2578(4) 0.2035(3) 0.0217(6) Uani 1 1 d . . .
H2C H 0.8791 0.2149 0.2156 0.026 Uiso 1 1 d R . .
H2B H 0.8096 0.2262 0.2918 0.026 Uiso 1 1 d R . .
C1 C 0.9451(2) 0.4105(4) 0.1162(3) 0.0179(6) Uani 1 1 d . . .
H1A H 0.9335 0.3613 0.0312 0.021 Uiso 1 1 d R . .
H1B H 0.9641 0.5147 0.1013 0.021 Uiso 1 1 d R . .
C5 C 0.7046(2) 0.6245(4) 0.2948(4) 0.0276(7) Uani 1 1 d . . .
H5B H 0.7578 0.6675 0.3406 0.033 Uiso 1 1 d R . .
C3 C 0.7951(2) 0.5312(4) 0.1091(3) 0.0225(7) Uani 1 1 d . . .
H3A H 0.7816 0.4965 0.0192 0.027 Uiso 1 1 d R . .
H3B H 0.8241 0.6301 0.1065 0.027 Uiso 1 1 d R . .
C10 C 0.4589(2) 0.5770(5) 0.3437(4) 0.0343(8) Uani 1 1 d . . .
C4 C 0.7091(2) 0.5502(4) 0.1723(3) 0.0240(7) Uani 1 1 d . . .
C6 C 0.6231(3) 0.6359(5) 0.3501(4) 0.0307(8) Uani 1 1 d . . .
H6B H 0.6201 0.6874 0.4337 0.037 Uiso 1 1 d R . .
C9 C 0.5464(2) 0.5728(4) 0.2838(4) 0.0302(8) Uani 1 1 d . . .
C8 C 0.6309(3) 0.4935(5) 0.1048(4) 0.0340(9) Uani 1 1 d . . .
H8A H 0.6327 0.4487 0.0182 0.041 Uiso 1 1 d R . .
C7 C 0.5501(3) 0.5022(5) 0.1618(4) 0.0383(10) Uani 1 1 d . . .
H7A H 0.4968 0.4587 0.1164 0.046 Uiso 1 1 d R . .
O3 O 1.02589(15) 0.3213(3) 0.3587(2) 0.0208(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0136(3) 0.0147(3) 0.0131(3) -0.0007(2) 0.0025(2) 0.0003(2)
P1 0.0130(4) 0.0158(4) 0.0156(4) -0.0016(3) 0.0022(3) 0.0007(3)
P2 0.0146(4) 0.0231(4) 0.0203(4) 0.0001(3) 0.0033(3) -0.0002(3)
N1 0.0135(12) 0.0205(13) 0.0189(12) 0.0003(10) 0.0027(10) 0.0023(10)
O1 0.0246(12) 0.0169(11) 0.0212(11) -0.0036(9) -0.0011(9) 0.0043(9)
O2 0.0168(11) 0.0352(14) 0.0243(12) 0.0009(10) 0.0027(9) -0.0053(10)
O4 0.0166(11) 0.0263(12) 0.0239(11) -0.0016(9) 0.0028(9) 0.0030(9)
O5 0.0178(12) 0.0346(13) 0.0246(12) 0.0026(10) 0.0028(9) 0.0032(10)
O6 0.0176(12) 0.0297(13) 0.0306(13) 0.0064(10) 0.0011(10) -0.0002(9)
O7 0.0271(14) 0.0500(18) 0.0459(17) -0.0063(14) 0.0137(12) 0.0020(13)
O8 0.0257(16) 0.098(3) 0.073(2) -0.039(2) 0.0211(16) -0.0181(17)
C2 0.0199(15) 0.0253(16) 0.0205(15) 0.0011(13) 0.0058(12) -0.0006(13)
C1 0.0152(14) 0.0197(15) 0.0194(14) 0.0012(12) 0.0051(11) 0.0002(12)
C5 0.0211(17) 0.0296(18) 0.0325(19) -0.0019(14) 0.0038(14) -0.0029(14)
C3 0.0163(16) 0.0254(17) 0.0260(17) 0.0054(13) 0.0027(13) 0.0032(12)
C10 0.0209(18) 0.040(2) 0.043(2) -0.0015(18) 0.0045(16) 0.0030(16)
C4 0.0167(16) 0.0246(17) 0.0310(18) 0.0042(14) 0.0043(13) 0.0041(13)
C6 0.0257(19) 0.035(2) 0.0328(19) -0.0040(15) 0.0084(15) 0.0005(15)
C9 0.0193(17) 0.035(2) 0.037(2) -0.0029(16) 0.0069(15) 0.0039(15)
C8 0.0211(18) 0.047(2) 0.034(2) -0.0091(16) 0.0019(15) 0.0038(16)
C7 0.0169(17) 0.052(3) 0.046(2) -0.0128(19) 0.0003(16) -0.0003(16)
O3 0.0245(12) 0.0223(12) 0.0162(10) -0.0017(9) 0.0044(9) 0.0026(9)

_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 2.094(2) . ?
Fe1 O1 2.094(2) 3_755 ?
Fe1 O4 2.154(2) . ?
Fe1 O4 2.154(2) 3_755 ?
Fe1 O3 2.162(2) 2_745 ?
Fe1 O3 2.162(2) 4_565 ?
P1 O3 1.501(2) . ?
P1 O1 1.507(2) . ?
P1 O2 1.574(2) . ?
P1 C1 1.833(3) . ?
P2 O4 1.487(2) . ?
P2 O6 1.518(2) . ?
P2 O5 1.571(2) . ?
P2 C2 1.834(3) . ?
N1 C1 1.509(4) . ?
N1 C2 1.510(4) . ?
N1 C3 1.529(4) . ?
O2 H2A 0.8501 . ?
O5 H5C 0.8500 . ?
O6 H6C 0.8500 . ?
O7 C10 1.216(5) . ?
O8 C10 1.305(5) . ?
O8 H8B 0.8500 . ?
C2 H2C 0.9601 . ?
C2 H2B 0.9600 . ?
C1 H1A 0.9601 . ?
C1 H1B 0.9599 . ?
C5 C6 1.396(5) . ?
C5 C4 1.401(5) . ?
C5 H5B 0.9601 . ?
C3 C4 1.503(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C10 C9 1.498(5) . ?
C4 C8 1.390(5) . ?
C6 C9 1.389(5) . ?
C6 H6B 0.9600 . ?
C9 C7 1.382(6) . ?
C8 C7 1.394(6) . ?
C8 H8A 0.9600 . ?
C7 H7A 0.9601 . ?
O3 Fe1 2.162(2) 2_755 ?

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 180.00(8) . 3_755 ?
O1 Fe1 O4 90.80(9) . . ?
O1 Fe1 O4 89.20(9) 3_755 . ?
O1 Fe1 O4 89.20(9) . 3_755 ?
O1 Fe1 O4 90.80(9) 3_755 3_755 ?
O4 Fe1 O4 180.00(12) . 3_755 ?
O1 Fe1 O3 87.63(9) . 2_745 ?
O1 Fe1 O3 92.37(9) 3_755 2_745 ?
O4 Fe1 O3 96.78(9) . 2_745 ?
O4 Fe1 O3 83.22(9) 3_755 2_745 ?
O1 Fe1 O3 92.37(9) . 4_565 ?
O1 Fe1 O3 87.63(9) 3_755 4_565 ?
O4 Fe1 O3 83.22(9) . 4_565 ?
O4 Fe1 O3 96.78(9) 3_755 4_565 ?
O3 Fe1 O3 180.00(12) 2_745 4_565 ?
O3 P1 O1 114.79(13) . . ?
O3 P1 O2 111.84(13) . . ?
O1 P1 O2 109.16(14) . . ?
O3 P1 C1 110.16(13) . . ?
O1 P1 C1 108.90(14) . . ?
O2 P1 C1 101.10(14) . . ?
O4 P2 O6 117.35(14) . . ?
O4 P2 O5 108.12(13) . . ?
O6 P2 O5 110.24(14) . . ?
O4 P2 C2 112.36(14) . . ?
O6 P2 C2 100.99(15) . . ?
O5 P2 C2 107.27(15) . . ?
C1 N1 C2 113.4(2) . . ?
C1 N1 C3 109.2(2) . . ?
C2 N1 C3 114.8(2) . . ?
P1 O1 Fe1 143.53(14) . . ?
P1 O2 H2A 109.2 . . ?
P2 O4 Fe1 139.47(14) . . ?
P2 O5 H5C 109.2 . . ?
P2 O6 H6C 109.4 . . ?
C10 O8 H8B 109.1 . . ?
N1 C2 P2 121.8(2) . . ?
N1 C2 H2C 89.8 . . ?
P2 C2 H2C 89.8 . . ?
N1 C2 H2B 119.1 . . ?
P2 C2 H2B 119.1 . . ?
H2C C2 H2B 90.0 . . ?
N1 C1 P1 113.7(2) . . ?
N1 C1 H1A 108.8 . . ?
P1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5B 120.1 . . ?
C4 C5 H5B 119.7 . . ?
C4 C3 N1 113.1(3) . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3A 108.8 . . ?
C4 C3 H3B 109.0 . . ?
N1 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O7 C10 O8 124.2(4) . . ?
O7 C10 C9 123.1(4) . . ?
O8 C10 C9 112.7(3) . . ?
C8 C4 C5 119.0(3) . . ?
C8 C4 C3 118.3(3) . . ?
C5 C4 C3 122.7(3) . . ?
C9 C6 C5 119.9(3) . . ?
C9 C6 H6B 120.0 . . ?
C5 C6 H6B 120.1 . . ?
C7 C9 C6 120.1(3) . . ?
C7 C9 C10 118.9(3) . . ?
C6 C9 C10 121.0(3) . . ?
C4 C8 C7 120.5(4) . . ?
C4 C8 H8A 119.6 . . ?
C7 C8 H8A 119.9 . . ?
C9 C7 C8 120.2(4) . . ?
C9 C7 H7A 119.8 . . ?
C8 C7 H7A 120.1 . . ?
P1 O3 Fe1 138.41(14) . 2_755 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 948671'