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

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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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_szg204
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Fe2 N O9 P2'
_chemical_formula_weight         464.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   15.5562(15)
_cell_length_b                   9.6049(9)
_cell_length_c                   10.2192(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.109(2)
_cell_angle_gamma                90.00
_cell_volume                     1507.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.43

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    2.185
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8986
_exptl_absorpt_correction_T_max  0.9785
_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            8344
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3113
_reflns_number_gt                2472
_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^)+(0.0444P)^2^+4.1134P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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 0.42820(4) 0.60061(6) 1.06503(5) 0.01351(16) Uani 1 1 d . . .
P2 P 0.35792(7) 0.43104(11) 0.80627(10) 0.0141(2) Uani 1 1 d . . .
O4 O 0.44165(17) 0.4808(3) 0.8941(3) 0.0166(6) Uani 1 1 d . . .
N1 N 0.2947(2) 0.6450(4) 0.9445(3) 0.0165(7) Uani 1 1 d . . .
C2 C 0.2836(3) 0.5741(4) 0.8119(4) 0.0164(9) Uani 1 1 d . . .
H2A H 0.2251 0.5398 0.7916 0.020 Uiso 1 1 d R . .
H2B H 0.2920 0.6410 0.7453 0.020 Uiso 1 1 d R . .
C3 C 0.2270(3) 0.5950(5) 1.0241(4) 0.0206(9) Uani 1 1 d . . .
H3B H 0.2333 0.6805 1.0732 0.025 Uiso 1 1 d R . .
H3A H 0.2425 0.5435 1.1049 0.025 Uiso 1 1 d R . .
C4 C 0.1331(3) 0.6332(5) 0.9713(4) 0.0237(10) Uani 1 1 d . . .
C5 C 0.0808(3) 0.5465(6) 0.8859(5) 0.0352(12) Uani 1 1 d . . .
H5A H 0.1032 0.4595 0.8596 0.042 Uiso 1 1 d R . .
C6 C -0.0065(3) 0.5865(7) 0.8362(5) 0.0429(15) Uani 1 1 d . . .
H6A H -0.0430 0.5299 0.7728 0.051 Uiso 1 1 d R . .
C7 C -0.0379(4) 0.7081(6) 0.8809(5) 0.0405(13) Uani 1 1 d . . .
C9 C 0.0977(3) 0.7555(6) 1.0126(6) 0.0429(14) Uani 1 1 d . . .
H9A H 0.1339 0.8163 1.0724 0.051 Uiso 1 1 d R . .
C8 C 0.0126(4) 0.7905(7) 0.9697(6) 0.0499(16) Uani 1 1 d . . .
H8A H -0.0114 0.8733 1.0021 0.060 Uiso 1 1 d R . .
O5 O 0.3681(2) 0.4184(3) 0.6635(3) 0.0275(7) Uani 1 1 d . . .
O6 O 0.32597(19) 0.2980(3) 0.8666(3) 0.0217(7) Uani 1 1 d . . .
C1 C 0.2948(3) 0.7995(4) 0.9260(4) 0.0159(8) Uani 1 1 d . . .
H1A H 0.2871 0.8436 1.0076 0.019 Uiso 1 1 d R . .
H1B H 0.2465 0.8251 0.8599 0.019 Uiso 1 1 d R . .
P1 P 0.39548(7) 0.86224(11) 0.87594(9) 0.0128(2) Uani 1 1 d . . .
O1 O 0.40165(19) 0.8178(3) 0.7343(3) 0.0176(6) Uani 1 1 d . . .
O2 O 0.39330(19) 1.0190(3) 0.8873(3) 0.0201(6) Uani 1 1 d . . .
O3 O 0.46660(17) 0.7885(3) 0.9742(3) 0.0162(6) Uani 1 1 d . . .
C10 C -0.1314(4) 0.7528(7) 0.8323(6) 0.0485(15) Uani 1 1 d . . .
O8 O -0.1607(3) 0.8600(6) 0.8723(5) 0.0804(17) Uani 1 1 d . . .
O7 O -0.1743(3) 0.6744(6) 0.7438(5) 0.0726(15) Uani 1 1 d . . .
H7B H -0.2083 0.6147 0.7697 0.087 Uiso 1 1 d R . .
O9 O 0.4149(2) 0.3789(3) 1.1513(3) 0.0218(7) Uani 1 1 d . . .
H9B H 0.3717 0.3808 1.1930 0.026 Uiso 1 1 d R . .
H9C H 0.4600 0.3647 1.2085 0.026 Uiso 1 1 d R . .
Fe2 Fe 0.39734(4) 0.18750(6) 1.01530(5) 0.01531(16) 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 0.0156(3) 0.0136(3) 0.0113(3) -0.0003(2) 0.0021(2) 0.0008(2)
P2 0.0170(5) 0.0120(5) 0.0124(5) -0.0008(4) -0.0003(4) 0.0017(4)
O4 0.0163(14) 0.0165(16) 0.0166(13) -0.0008(12) 0.0012(11) 0.0013(12)
N1 0.0179(18) 0.0171(18) 0.0144(16) 0.0012(14) 0.0027(13) -0.0003(14)
C2 0.017(2) 0.016(2) 0.0148(18) -0.0011(16) -0.0012(15) 0.0015(16)
C3 0.014(2) 0.029(3) 0.0174(19) 0.0049(18) 0.0004(16) -0.0029(18)
C4 0.016(2) 0.031(3) 0.025(2) 0.006(2) 0.0061(17) -0.0021(18)
C5 0.026(3) 0.046(3) 0.036(3) -0.009(2) 0.010(2) -0.008(2)
C6 0.030(3) 0.066(4) 0.031(3) -0.005(3) 0.000(2) -0.017(3)
C7 0.036(3) 0.042(3) 0.043(3) 0.014(3) 0.005(2) 0.010(3)
C9 0.026(3) 0.039(3) 0.063(4) -0.011(3) 0.006(3) -0.002(2)
C8 0.032(3) 0.045(4) 0.072(4) -0.005(3) 0.005(3) 0.005(3)
O5 0.042(2) 0.0253(18) 0.0157(14) -0.0029(13) 0.0070(13) 0.0073(15)
O6 0.0244(16) 0.0164(16) 0.0216(14) 0.0052(12) -0.0047(12) -0.0022(12)
C1 0.016(2) 0.016(2) 0.0162(18) -0.0005(17) 0.0036(15) 0.0011(16)
P1 0.0168(5) 0.0105(5) 0.0110(4) -0.0001(4) 0.0022(4) -0.0005(4)
O1 0.0246(16) 0.0161(16) 0.0125(13) -0.0010(11) 0.0043(11) -0.0028(12)
O2 0.0326(17) 0.0125(15) 0.0159(13) -0.0014(12) 0.0061(12) -0.0002(13)
O3 0.0167(14) 0.0141(15) 0.0173(13) 0.0021(12) 0.0013(11) -0.0015(12)
C10 0.037(3) 0.052(4) 0.056(4) 0.006(3) 0.006(3) 0.008(3)
O8 0.054(3) 0.079(4) 0.099(4) -0.013(3) -0.016(3) 0.032(3)
O7 0.039(3) 0.098(4) 0.073(3) -0.003(3) -0.014(2) 0.002(3)
O9 0.0284(17) 0.0206(16) 0.0184(14) -0.0003(13) 0.0094(12) -0.0032(13)
Fe2 0.0203(3) 0.0132(3) 0.0120(3) 0.0011(2) 0.0015(2) -0.0006(2)

_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 2.001(3) 4_576 ?
Fe1 O4 2.129(3) . ?
Fe1 O4 2.149(3) 3_667 ?
Fe1 O3 2.157(3) . ?
Fe1 N1 2.281(3) . ?
Fe1 O9 2.327(3) . ?
P2 O5 1.497(3) . ?
P2 O4 1.536(3) . ?
P2 O6 1.536(3) . ?
P2 C2 1.802(4) . ?
O4 Fe1 2.149(3) 3_667 ?
N1 C1 1.495(5) . ?
N1 C2 1.501(5) . ?
N1 C3 1.507(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9601 . ?
C3 C4 1.520(6) . ?
C3 H3B 0.9600 . ?
C3 H3A 0.9601 . ?
C4 C5 1.376(7) . ?
C4 C9 1.391(7) . ?
C5 C6 1.425(7) . ?
C5 H5A 0.9601 . ?
C6 C7 1.371(8) . ?
C6 H6A 0.9600 . ?
C7 C8 1.358(8) . ?
C7 C10 1.522(8) . ?
C9 C8 1.369(7) . ?
C9 H9A 0.9600 . ?
C8 H8A 0.9599 . ?
O5 Fe2 1.938(3) 4_565 ?
O6 Fe2 2.033(3) . ?
C1 P1 1.825(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9601 . ?
P1 O2 1.511(3) . ?
P1 O1 1.527(3) . ?
P1 O3 1.543(3) . ?
O1 Fe1 2.001(3) 4_575 ?
O2 Fe2 2.075(3) 1_565 ?
O3 Fe2 2.115(3) 3_667 ?
C10 O8 1.222(8) . ?
C10 O7 1.280(8) . ?
O7 H7B 0.8501 . ?
O9 Fe2 2.294(3) . ?
O9 H9B 0.8499 . ?
O9 H9C 0.8500 . ?
Fe2 O5 1.938(3) 4_566 ?
Fe2 O2 2.075(3) 1_545 ?
Fe2 O3 2.115(3) 3_667 ?

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 O4 168.91(12) 4_576 . ?
O1 Fe1 O4 106.96(11) 4_576 3_667 ?
O4 Fe1 O4 75.56(11) . 3_667 ?
O1 Fe1 O3 98.84(11) 4_576 . ?
O4 Fe1 O3 91.68(11) . . ?
O4 Fe1 O3 94.08(11) 3_667 . ?
O1 Fe1 N1 95.67(12) 4_576 . ?
O4 Fe1 N1 81.81(11) . . ?
O4 Fe1 N1 157.27(11) 3_667 . ?
O3 Fe1 N1 84.35(11) . . ?
O1 Fe1 O9 89.33(11) 4_576 . ?
O4 Fe1 O9 80.91(10) . . ?
O4 Fe1 O9 74.42(11) 3_667 . ?
O3 Fe1 O9 167.52(11) . . ?
N1 Fe1 O9 104.34(12) . . ?
O5 P2 O4 112.60(17) . . ?
O5 P2 O6 114.50(18) . . ?
O4 P2 O6 108.80(15) . . ?
O5 P2 C2 105.08(18) . . ?
O4 P2 C2 103.46(17) . . ?
O6 P2 C2 111.83(19) . . ?
P2 O4 Fe1 117.58(15) . . ?
P2 O4 Fe1 133.32(17) . 3_667 ?
Fe1 O4 Fe1 104.44(11) . 3_667 ?
C1 N1 C2 109.8(3) . . ?
C1 N1 C3 113.5(3) . . ?
C2 N1 C3 110.6(3) . . ?
C1 N1 Fe1 103.6(2) . . ?
C2 N1 Fe1 111.5(2) . . ?
C3 N1 Fe1 107.6(2) . . ?
N1 C2 P2 113.1(3) . . ?
N1 C2 H2A 108.7 . . ?
P2 C2 H2A 108.8 . . ?
N1 C2 H2B 109.1 . . ?
P2 C2 H2B 109.2 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 116.5(3) . . ?
N1 C3 H3B 89.3 . . ?
C4 C3 H3B 89.5 . . ?
N1 C3 H3A 121.8 . . ?
C4 C3 H3A 121.7 . . ?
H3B C3 H3A 90.0 . . ?
C5 C4 C9 118.7(5) . . ?
C5 C4 C3 121.2(4) . . ?
C9 C4 C3 120.1(4) . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.2 . . ?
C7 C6 C5 118.7(5) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 121.1 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 C10 118.4(6) . . ?
C6 C7 C10 120.3(5) . . ?
C8 C9 C4 121.3(5) . . ?
C8 C9 H9A 119.6 . . ?
C4 C9 H9A 119.1 . . ?
C7 C8 C9 119.9(6) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 120.2 . . ?
P2 O5 Fe2 151.5(2) . 4_565 ?
P2 O6 Fe2 124.15(17) . . ?
N1 C1 P1 112.4(3) . . ?
N1 C1 H1A 109.0 . . ?
P1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.1 . . ?
P1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O2 P1 O1 110.95(16) . . ?
O2 P1 O3 115.46(16) . . ?
O1 P1 O3 109.99(16) . . ?
O2 P1 C1 106.07(18) . . ?
O1 P1 C1 111.04(17) . . ?
O3 P1 C1 102.98(17) . . ?
P1 O1 Fe1 139.69(18) . 4_575 ?
P1 O2 Fe2 145.77(17) . 1_565 ?
P1 O3 Fe2 126.27(16) . 3_667 ?
P1 O3 Fe1 116.44(15) . . ?
Fe2 O3 Fe1 114.37(12) 3_667 . ?
O8 C10 O7 123.4(6) . . ?
O8 C10 C7 121.1(6) . . ?
O7 C10 C7 115.4(6) . . ?
C10 O7 H7B 117.2 . . ?
Fe2 O9 Fe1 120.87(12) . . ?
Fe2 O9 H9B 107.1 . . ?
Fe1 O9 H9B 107.1 . . ?
Fe2 O9 H9C 107.1 . . ?
Fe1 O9 H9C 107.1 . . ?
H9B O9 H9C 106.8 . . ?
O5 Fe2 O6 133.64(14) 4_566 . ?
O5 Fe2 O2 95.50(12) 4_566 1_545 ?
O6 Fe2 O2 88.71(12) . 1_545 ?
O5 Fe2 O3 112.00(12) 4_566 3_667 ?
O6 Fe2 O3 113.88(12) . 3_667 ?
O2 Fe2 O3 92.72(11) 1_545 3_667 ?
O5 Fe2 O9 88.12(12) 4_566 . ?
O6 Fe2 O9 91.89(11) . . ?
O2 Fe2 O9 174.39(12) 1_545 . ?
O3 Fe2 O9 81.94(11) 3_667 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 948670'