# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1874963'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 Fe N O5 P'
_chemical_formula_sum            'C9 H16 Fe N O5 P'
_chemical_formula_weight         305.05

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.3354(4)
_cell_length_b                   18.3354(4)
_cell_length_c                   6.1492(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1790.32(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3216
_cell_measurement_theta_min      2.221
_cell_measurement_theta_max      27.537

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.406
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15697
_diffrn_reflns_av_unetI/netI     0.0994
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         28.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             2410
_reflns_number_gt                1929
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.507
_reflns_Friedel_fraction_max     0.607
_reflns_Friedel_fraction_full    0.638

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²+4.2752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2410
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.24230(6) 0.17041(6) 1.09783(19) 0.0140(3) Uani 1 1 d . . . . .
P1 P 0.24480(11) 0.22312(11) 0.6151(3) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.3413(5) 0.2989(5) 0.7514(13) 0.0164(15) Uani 1 1 d . . . . .
H1A H 0.3871 0.3269 0.6432 0.020 Uiso 1 1 calc R U . . .
H1B H 0.3328 0.3426 0.8222 0.020 Uiso 1 1 calc R U . . .
C2 C 0.4394(5) 0.3148(5) 1.0527(12) 0.0186(16) Uani 1 1 d . . . . .
H2 H 0.4201 0.3432 1.1583 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4681(6) 0.2619(6) 1.1835(15) 0.0278(19) Uani 1 1 d . . . . .
H3A H 0.4910 0.2366 1.0838 0.042 Uiso 1 1 calc R U . . .
H3B H 0.4200 0.2173 1.2620 0.042 Uiso 1 1 calc R U . . .
H3C H 0.5117 0.2982 1.2877 0.042 Uiso 1 1 calc R U . . .
C4 C 0.5115(5) 0.3824(5) 0.9224(13) 0.0200(16) Uani 1 1 d . . . . .
C5 C 0.5433(6) 0.3629(6) 0.7377(15) 0.029(2) Uani 1 1 d . . . . .
H5 H 0.5198 0.3056 0.6960 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6071(5) 0.4237(5) 0.6155(19) 0.0290(18) Uani 1 1 d . . . . .
H6 H 0.6260 0.4082 0.4890 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6448(6) 0.5084(6) 0.6751(16) 0.0273(19) Uani 1 1 d . . . . .
H7 H 0.6887 0.5510 0.5899 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6164(6) 0.5287(6) 0.8618(16) 0.028(2) Uani 1 1 d . . . . .
H8 H 0.6427 0.5858 0.9077 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5504(6) 0.4673(6) 0.9829(15) 0.0259(18) Uani 1 1 d . . . . .
H9 H 0.5313 0.4831 1.1084 0.031 Uiso 1 1 calc R U . . .
N1 N 0.3656(4) 0.2558(4) 0.9182(11) 0.0165(13) Uani 1 1 d . . . . .
H1C H 0.3818 0.2185 0.8387 0.020 Uiso 1 1 calc R U . . .
O1 O 0.2721(4) 0.1896(4) 0.4209(9) 0.0189(12) Uani 1 1 d . . . . .
O2 O 0.1982(3) 0.2686(3) 0.5468(8) 0.0168(11) Uani 1 1 d . . . . .
O3 O 0.1957(3) 0.1528(3) 0.7826(9) 0.0152(11) Uani 1 1 d . . . . .
O1W O 0.2260(3) 0.2833(3) 1.1151(11) 0.0169(10) Uani 1 1 d . . . . .
H1WA H 0.1850 0.2760 1.0382 0.025 Uiso 1 1 d R U . . .
H1WB H 0.2139 0.2806 1.2463 0.025 Uiso 1 1 d R U . . .
O2W O 0.1095(4) 0.0937(4) 1.1872(11) 0.0250(14) Uani 1 1 d . . . . .
H2WA H 0.0919 0.0483 1.2562 0.038 Uiso 1 1 d R U . . .
H2WB H 0.0871 0.1212 1.2345 0.038 Uiso 1 1 d R U . . .


_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 2.044(6) 1_556 ?
Fe1 O3 2.077(5) . ?
Fe1 O2 2.139(5) 5 ?
Fe1 O2W 2.188(6) . ?
Fe1 O1W 2.237(5) . ?
Fe1 N1 2.290(7) . ?
P1 O2 1.521(5) . ?
P1 O1 1.537(6) . ?
P1 O3 1.541(6) . ?
P1 C1 1.818(8) . ?
C1 N1 1.493(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.490(10) . ?
C2 C4 1.513(11) . ?
C2 C3 1.543(12) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C9 1.401(12) . ?
C4 C5 1.403(11) . ?
C5 C6 1.368(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N1 H1C 1.0000 . ?
O1 Fe1 2.044(6) 1_554 ?
O2 Fe1 2.139(5) 6_554 ?
O1W H1WA 0.8408 . ?
O1W H1WB 0.8317 . ?
O2W H2WA 0.8418 . ?
O2W H2WB 0.8438 . ?

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 O3 171.0(2) 1_556 . ?
O1 Fe1 O2 97.7(2) 1_556 5 ?
O3 Fe1 O2 88.9(2) . 5 ?
O1 Fe1 O2W 89.0(3) 1_556 . ?
O3 Fe1 O2W 84.0(2) . . ?
O2 Fe1 O2W 98.1(2) 5 . ?
O1 Fe1 O1W 86.7(2) 1_556 . ?
O3 Fe1 O1W 87.3(2) . . ?
O2 Fe1 O1W 172.6(2) 5 . ?
O2W Fe1 O1W 87.8(2) . . ?
O1 Fe1 N1 105.3(2) 1_556 . ?
O3 Fe1 N1 81.1(2) . . ?
O2 Fe1 N1 87.0(2) 5 . ?
O2W Fe1 N1 164.1(2) . . ?
O1W Fe1 N1 86.1(2) . . ?
O2 P1 O1 112.9(3) . . ?
O2 P1 O3 113.0(3) . . ?
O1 P1 O3 110.8(3) . . ?
O2 P1 C1 107.9(3) . . ?
O1 P1 C1 106.1(4) . . ?
O3 P1 C1 105.6(3) . . ?
N1 C1 P1 110.3(5) . . ?
N1 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C4 113.9(6) . . ?
N1 C2 C3 107.7(7) . . ?
C4 C2 C3 110.9(7) . . ?
N1 C2 H2 108.0 . . ?
C4 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 117.0(8) . . ?
C9 C4 C2 121.3(8) . . ?
C5 C4 C2 121.7(8) . . ?
C6 C5 C4 122.1(8) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.5(9) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 118.2(9) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C9 121.3(8) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 120.8(8) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C2 N1 C1 113.6(6) . . ?
C2 N1 Fe1 117.1(5) . . ?
C1 N1 Fe1 103.8(4) . . ?
C2 N1 H1C 107.3 . . ?
C1 N1 H1C 107.3 . . ?
Fe1 N1 H1C 107.3 . . ?
P1 O1 Fe1 135.4(3) . 1_554 ?
P1 O2 Fe1 132.7(3) . 6_554 ?
P1 O3 Fe1 118.1(3) . . ?
Fe1 O1W H1WA 110.4 . . ?
Fe1 O1W H1WB 98.4 . . ?
H1WA O1W H1WB 110.1 . . ?
Fe1 O2W H2WA 120.9 . . ?
Fe1 O2W H2WB 114.8 . . ?
H2WA O2W H2WB 110.9 . . ?

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
O2 P1 C1 N1 149.8(5) . . . . ?
O1 P1 C1 N1 -88.9(6) . . . . ?
O3 P1 C1 N1 28.8(6) . . . . ?
N1 C2 C4 C9 131.4(8) . . . . ?
C3 C2 C4 C9 -106.9(9) . . . . ?
N1 C2 C4 C5 -49.5(11) . . . . ?
C3 C2 C4 C5 72.2(10) . . . . ?
C9 C4 C5 C6 -2.6(14) . . . . ?
C2 C4 C5 C6 178.3(9) . . . . ?
C4 C5 C6 C7 1.8(16) . . . . ?
C5 C6 C7 C8 0.7(15) . . . . ?
C6 C7 C8 C9 -2.3(14) . . . . ?
C7 C8 C9 C4 1.5(15) . . . . ?
C5 C4 C9 C8 1.0(14) . . . . ?
C2 C4 C9 C8 -179.9(8) . . . . ?
C4 C2 N1 C1 -45.4(9) . . . . ?
C3 C2 N1 C1 -168.8(7) . . . . ?
C4 C2 N1 Fe1 -166.5(5) . . . . ?
C3 C2 N1 Fe1 70.1(7) . . . . ?
P1 C1 N1 C2 -174.2(5) . . . . ?
P1 C1 N1 Fe1 -45.9(6) . . . . ?
O2 P1 O1 Fe1 -14.7(6) . . . 1_554 ?
O3 P1 O1 Fe1 113.2(5) . . . 1_554 ?
C1 P1 O1 Fe1 -132.6(5) . . . 1_554 ?
O1 P1 O2 Fe1 115.6(4) . . . 6_554 ?
O3 P1 O2 Fe1 -11.2(5) . . . 6_554 ?
C1 P1 O2 Fe1 -127.5(4) . . . 6_554 ?
O2 P1 O3 Fe1 -110.8(4) . . . . ?
O1 P1 O3 Fe1 121.3(4) . . . . ?
C1 P1 O3 Fe1 6.9(4) . . . . ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1874964'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 Fe N O5 P'
_chemical_formula_sum            'C9 H16 Fe N O5 P'
_chemical_formula_weight         305.05

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.4179(4)
_cell_length_b                   18.4179(4)
_cell_length_c                   6.1607(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1809.84(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9202
_cell_measurement_theta_min      2.216
_cell_measurement_theta_max      28.185

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.391
_shelx_estimated_absorpt_T_min   0.337
_shelx_estimated_absorpt_T_max   0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12979
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.277
_diffrn_reflns_theta_max         28.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2953
_reflns_number_gt                2886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+0.3425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.036(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.75817(2) 0.83011(2) -0.09813(5) 0.01767(7) Uani 1 1 d . . . . .
P1 P 0.75595(3) 0.77738(3) 0.38394(9) 0.01703(9) Uani 1 1 d . . . . .
C1 C 0.65956(12) 0.70160(12) 0.2481(3) 0.0219(4) Uani 1 1 d . . . . .
H1A H 0.6680 0.6581 0.1771 0.026 Uiso 1 1 calc R U . . .
H1B H 0.6141 0.6737 0.3563 0.026 Uiso 1 1 calc R U . . .
C2 C 0.56158(13) 0.68574(13) -0.0504(3) 0.0267(4) Uani 1 1 d . . . . .
H2 H 0.5806 0.6570 -0.1547 0.032 Uiso 1 1 calc R U . . .
C3 C 0.53421(17) 0.73816(18) -0.1825(5) 0.0440(6) Uani 1 1 d . . . . .
H3A H 0.5127 0.7649 -0.0845 0.066 Uiso 1 1 calc R U . . .
H3B H 0.4901 0.7018 -0.2846 0.066 Uiso 1 1 calc R U . . .
H3C H 0.5823 0.7814 -0.2633 0.066 Uiso 1 1 calc R U . . .
C4 C 0.48908(12) 0.61825(14) 0.0803(4) 0.0276(4) Uani 1 1 d . . . . .
C5 C 0.45862(16) 0.63839(16) 0.2632(5) 0.0441(6) Uani 1 1 d . . . . .
H5 H 0.4827 0.6954 0.3061 0.053 Uiso 1 1 calc R U . . .
C6 C 0.39386(14) 0.57668(16) 0.3834(6) 0.0507(7) Uani 1 1 d . . . . .
H6 H 0.3743 0.5918 0.5087 0.061 Uiso 1 1 calc R U . . .
C7 C 0.35753(16) 0.49433(17) 0.3249(5) 0.0457(7) Uani 1 1 d . . . . .
H7 H 0.3134 0.4522 0.4093 0.055 Uiso 1 1 calc R U . . .
C8 C 0.38560(17) 0.47343(16) 0.1426(5) 0.0456(7) Uani 1 1 d . . . . .
H8 H 0.3598 0.4164 0.0987 0.055 Uiso 1 1 calc R U . . .
C9 C 0.45150(16) 0.53475(15) 0.0209(5) 0.0394(6) Uani 1 1 d . . . . .
H9 H 0.4708 0.5191 -0.1039 0.047 Uiso 1 1 calc R U . . .
N1 N 0.63529(10) 0.74423(10) 0.0832(3) 0.0210(3) Uani 1 1 d . . . . .
H1C H 0.6193 0.7814 0.1633 0.025 Uiso 1 1 calc R U . . .
O1 O 0.72930(10) 0.81044(10) 0.5789(2) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.80255(8) 0.73239(8) 0.4515(2) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.80413(9) 0.84639(8) 0.2168(2) 0.0214(3) Uani 1 1 d . . . . .
O1W O 0.77453(8) 0.71707(7) -0.1159(3) 0.0240(3) Uani 1 1 d . . . . .
H1WA H 0.8156 0.7244 -0.0390 0.036 Uiso 1 1 d R U . . .
H1WB H 0.7867 0.7198 -0.2470 0.036 Uiso 1 1 d R U . . .
O2W O 0.89076(10) 0.90733(10) -0.1890(3) 0.0381(4) Uani 1 1 d . . . . .
H2WA H 0.9083 0.9527 -0.2580 0.057 Uiso 1 1 d R U . . .
H2WB H 0.9131 0.8799 -0.2363 0.057 Uiso 1 1 d R U . . .


_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 2.0447(15) 1_554 ?
Fe1 O3 2.0777(14) . ?
Fe1 O2 2.1367(13) 5_564 ?
Fe1 O2W 2.1969(16) . ?
Fe1 O1W 2.2504(12) . ?
Fe1 N1 2.3004(17) . ?
P1 O2 1.5191(13) . ?
P1 O3 1.5283(15) . ?
P1 O1 1.5338(15) . ?
P1 C1 1.823(2) . ?
C1 N1 1.483(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.489(2) . ?
C2 C4 1.522(3) . ?
C2 C3 1.528(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C9 1.383(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.365(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N1 H1C 1.0000 . ?
O1 Fe1 2.0447(15) 1_556 ?
O2 Fe1 2.1368(13) 6_655 ?
O1W H1WA 0.8439 . ?
O1W H1WB 0.8334 . ?
O2W H2WA 0.8450 . ?
O2W H2WB 0.8474 . ?

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 O3 170.20(6) 1_554 . ?
O1 Fe1 O2 98.15(5) 1_554 5_564 ?
O3 Fe1 O2 89.53(5) . 5_564 ?
O1 Fe1 O2W 88.46(7) 1_554 . ?
O3 Fe1 O2W 84.47(7) . . ?
O2 Fe1 O2W 97.63(6) 5_564 . ?
O1 Fe1 O1W 86.10(6) 1_554 . ?
O3 Fe1 O1W 86.88(6) . . ?
O2 Fe1 O1W 172.92(6) 5_564 . ?
O2W Fe1 O1W 88.10(5) . . ?
O1 Fe1 N1 105.75(6) 1_554 . ?
O3 Fe1 N1 80.54(6) . . ?
O2 Fe1 N1 87.51(6) 5_564 . ?
O2W Fe1 N1 164.12(7) . . ?
O1W Fe1 N1 85.88(5) . . ?
O2 P1 O3 112.76(8) . . ?
O2 P1 O1 112.46(8) . . ?
O3 P1 O1 111.43(8) . . ?
O2 P1 C1 107.93(8) . . ?
O3 P1 C1 105.41(9) . . ?
O1 P1 C1 106.32(9) . . ?
N1 C1 P1 110.19(13) . . ?
N1 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C4 114.13(17) . . ?
N1 C2 C3 107.86(18) . . ?
C4 C2 C3 111.47(19) . . ?
N1 C2 H2 107.7 . . ?
C4 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 117.8(2) . . ?
C9 C4 C2 121.0(2) . . ?
C5 C4 C2 121.2(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 120.5(2) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C1 N1 C2 113.74(15) . . ?
C1 N1 Fe1 104.09(11) . . ?
C2 N1 Fe1 117.18(13) . . ?
C1 N1 H1C 107.1 . . ?
C2 N1 H1C 107.1 . . ?
Fe1 N1 H1C 107.1 . . ?
P1 O1 Fe1 136.54(9) . 1_556 ?
P1 O2 Fe1 133.09(8) . 6_655 ?
P1 O3 Fe1 118.94(8) . . ?
Fe1 O1W H1WA 110.4 . . ?
Fe1 O1W H1WB 98.5 . . ?
H1WA O1W H1WB 110.0 . . ?
Fe1 O2W H2WA 121.3 . . ?
Fe1 O2W H2WB 114.6 . . ?
H2WA O2W H2WB 111.0 . . ?

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
O2 P1 C1 N1 -149.87(13) . . . . ?
O3 P1 C1 N1 -29.15(15) . . . . ?
O1 P1 C1 N1 89.25(15) . . . . ?
N1 C2 C4 C9 -130.5(2) . . . . ?
C3 C2 C4 C9 107.0(3) . . . . ?
N1 C2 C4 C5 49.3(3) . . . . ?
C3 C2 C4 C5 -73.2(3) . . . . ?
C9 C4 C5 C6 1.1(4) . . . . ?
C2 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
C5 C4 C9 C8 -0.3(4) . . . . ?
C2 C4 C9 C8 179.5(2) . . . . ?
C7 C8 C9 C4 -0.9(4) . . . . ?
P1 C1 N1 C2 174.50(14) . . . . ?
P1 C1 N1 Fe1 45.84(14) . . . . ?
C4 C2 N1 C1 45.5(2) . . . . ?
C3 C2 N1 C1 169.92(19) . . . . ?
C4 C2 N1 Fe1 167.12(14) . . . . ?
C3 C2 N1 Fe1 -68.4(2) . . . . ?
O2 P1 O1 Fe1 14.58(17) . . . 1_556 ?
O3 P1 O1 Fe1 -113.15(14) . . . 1_556 ?
C1 P1 O1 Fe1 132.49(14) . . . 1_556 ?
O3 P1 O2 Fe1 11.75(14) . . . 6_655 ?
O1 P1 O2 Fe1 -115.28(11) . . . 6_655 ?
C1 P1 O2 Fe1 127.75(11) . . . 6_655 ?
O2 P1 O3 Fe1 111.11(9) . . . . ?
O1 P1 O3 Fe1 -121.32(9) . . . . ?
C1 P1 O3 Fe1 -6.40(11) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

