# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_a36a_0m
_database_code_depnum_ccdc_archive 'CCDC 1810831'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-11
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) 
;
_shelxl_version_number           2014-3


_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C14 H27 Fe N O3 P2'
_chemical_formula_sum            'C14 H27 Fe N O3 P2'
_chemical_formula_weight         375.15
_chemical_melting_point          ?
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'

_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. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6009(8)
_cell_length_b                   10.8786(7)
_cell_length_c                   14.5310(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.1955(16)
_cell_angle_gamma                90
_cell_volume                     1881.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.270
_cell_measurement_theta_min      2.389
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.462
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  0.9139
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.933
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.128
_exptl_crystal_id                a36a_0m


_exptl_crystal_preparation       
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the 0 -1 2 scattering 
planes roughly normal to the spindle axis. 
;
_exptl_special_details           
; 
One distinct cell was identified using APEX2 (Bruker, 2013).  11 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2013) then corrected for absorption by 
integration using SADABS v2012/1 (Bruker, 2012). 
No decay correction was applied. 
 
;

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.359
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  a36a_0m
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4267
_reflns_number_total             4688
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2013.10-0 (Bruker, 2013)'

_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2013/3, SADABS V2012/1, TWINABS V2012/1 
(Bruker, 2012 & 2013) 
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELX-2013-4 (Sheldrick, 2013)'

_computing_structure_solution    'SHELX-2013-4 (Sheldrick, 2013)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0189
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+1.0065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          
; 
Structure was phased by intrinsic phasing (Sheldrick, 
2008).  Systematic conditions suggested the un??ambiguous space group. 
The space group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  The highest peaks in 
the final difference Fourier map were in the vicinity of atoms C13; 
final map had no other significant features.  A final analysis of 
variance between observed and calculated structure factors showed no 
dependence on amplitude or resolution. 
;

_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B), C4(H4A,H4B), C13(H13A,H13B), C11(H11A,H11B), C5(H5A,H5B), C7(H7A, 
 H7B) 
2.b Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C6(H6A,H6B,H6C), C10(H10A,H10B, 
 H10C), C8(H8A,H8B,H8C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.21231(2) 0.16648(2) 0.30010(2) 0.01161(4) Uani 1 1 d . . . . .
P2 P 0.19077(2) 0.21104(2) 0.14611(2) 0.01229(6) Uani 1 1 d . . . . .
O3 O 0.43230(7) 0.23450(9) 0.43648(7) 0.0294(2) Uani 1 1 d . . . . .
O2 O 0.04242(7) 0.04793(8) 0.36739(6) 0.02369(17) Uani 1 1 d . . . . .
C3 C 0.34677(9) 0.20587(10) 0.38077(8) 0.0179(2) Uani 1 1 d . . . . .
C2 C 0.10826(9) 0.09292(10) 0.33811(8) 0.0164(2) Uani 1 1 d . . . . .
P1 P 0.27575(2) -0.01769(2) 0.27798(2) 0.01300(6) Uani 1 1 d . . . . .
N1 N 0.30442(8) 0.01389(8) 0.09969(7) 0.01690(18) Uani 1 1 d . . . . .
C9 C 0.16762(9) -0.13375(10) 0.22436(8) 0.0188(2) Uani 1 1 d . . . . .
H9A H 0.1221 -0.1423 0.2664 0.023 Uiso 1 1 calc R . . . .
H9B H 0.1190 -0.1027 0.1622 0.023 Uiso 1 1 calc R . . . .
C4 C 0.36431(9) -0.02393(10) 0.19980(8) 0.0171(2) Uani 1 1 d . . . . .
H4A H 0.4289 0.0292 0.2269 0.021 Uiso 1 1 calc R . . . .
H4B H 0.3917 -0.1072 0.1995 0.021 Uiso 1 1 calc R . . . .
C13 C 0.05955(9) 0.16762(10) 0.05081(8) 0.0177(2) Uani 1 1 d . . . . .
H13A H 0.0568 0.2079 -0.0095 0.021 Uiso 1 1 calc R . . . .
H13B H 0.0602 0.0796 0.0403 0.021 Uiso 1 1 calc R . . . .
C11 C 0.20405(9) 0.37470(10) 0.12001(8) 0.0179(2) Uani 1 1 d . . . . .
H11A H 0.1988 0.3833 0.0522 0.021 Uiso 1 1 calc R . . . .
H11B H 0.1416 0.4193 0.1292 0.021 Uiso 1 1 calc R . . . .
C14 C -0.04655(9) 0.20047(13) 0.07395(9) 0.0251(2) Uani 1 1 d . . . . .
H14A H -0.1112 0.1708 0.0228 0.038 Uiso 1 1 calc GR . . . .
H14B H -0.0515 0.2881 0.0790 0.038 Uiso 1 1 calc GR . . . .
H14C H -0.0438 0.1631 0.1346 0.038 Uiso 1 1 calc GR . . . .
C5 C 0.29271(9) 0.14797(10) 0.09224(8) 0.0167(2) Uani 1 1 d . . . . .
H5A H 0.2697 0.1710 0.0240 0.020 Uiso 1 1 calc R . . . .
H5B H 0.3655 0.1850 0.1244 0.020 Uiso 1 1 calc R . . . .
C12 C 0.31399(10) 0.43311(11) 0.18393(9) 0.0239(2) Uani 1 1 d . . . . .
H12A H 0.3149 0.5185 0.1675 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.3763 0.3920 0.1731 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.3198 0.4255 0.2512 0.036 Uiso 1 1 calc GR . . . .
O1 O 0.11973(7) 0.40641(8) 0.32339(6) 0.02419(17) Uani 1 1 d . . . . .
C7 C 0.37123(9) -0.09057(10) 0.38802(8) 0.0177(2) Uani 1 1 d . . . . .
H7A H 0.3940 -0.1701 0.3708 0.021 Uiso 1 1 calc R . . . .
H7B H 0.4382 -0.0404 0.4131 0.021 Uiso 1 1 calc R . . . .
C6 C 0.36474(11) -0.02874(12) 0.03491(9) 0.0281(3) Uani 1 1 d . . . . .
H6A H 0.4377 0.0087 0.0537 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.3232 -0.0064 -0.0310 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.3728 -0.1165 0.0396 0.042 Uiso 1 1 calc GR . . . .
C10 C 0.20774(11) -0.26154(11) 0.20754(11) 0.0301(3) Uani 1 1 d . . . . .
H10A H 0.2488 -0.2560 0.1626 0.045 Uiso 1 1 calc GR . . . .
H10B H 0.1440 -0.3145 0.1812 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.2556 -0.2944 0.2683 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.31883(10) -0.10795(13) 0.46775(9) 0.0286(3) Uani 1 1 d . . . . .
H8A H 0.2563 -0.1634 0.4454 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.2933 -0.0300 0.4834 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.3738 -0.1414 0.5248 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.15529(9) 0.31197(10) 0.31292(7) 0.0161(2) Uani 1 1 d . . . . .


_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 P2 2.2172(3) . ?
Fe1 C3 1.7670(11) . ?
Fe1 C2 1.7723(11) . ?
Fe1 P1 2.2193(3) . ?
Fe1 C1 1.7732(11) . ?
P2 C13 1.8355(11) . ?
P2 C11 1.8394(11) . ?
P2 C5 1.8425(11) . ?
O3 C3 1.1576(14) . ?
O2 C2 1.1580(13) . ?
P1 C9 1.8329(11) . ?
P1 C4 1.8368(11) . ?
P1 C7 1.8352(11) . ?
N1 C4 1.4605(14) . ?
N1 C5 1.4665(14) . ?
N1 C6 1.4661(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5261(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5244(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5296(15) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 C1 1.1508(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5222(15) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
P2 Fe1 P1 88.948(11) . . ?
C3 Fe1 P2 112.90(4) . . ?
C3 Fe1 C2 123.30(5) . . ?
C3 Fe1 P1 90.15(4) . . ?
C3 Fe1 C1 92.70(5) . . ?
C2 Fe1 P2 123.75(3) . . ?
C2 Fe1 P1 88.64(3) . . ?
C2 Fe1 C1 90.19(5) . . ?
C1 Fe1 P2 89.51(3) . . ?
C1 Fe1 P1 177.12(4) . . ?
C13 P2 Fe1 119.09(4) . . ?
C13 P2 C11 102.36(5) . . ?
C13 P2 C5 99.48(5) . . ?
C11 P2 Fe1 115.50(4) . . ?
C11 P2 C5 98.59(5) . . ?
C5 P2 Fe1 118.44(4) . . ?
O3 C3 Fe1 176.65(10) . . ?
O2 C2 Fe1 176.55(10) . . ?
C9 P1 Fe1 115.50(4) . . ?
C9 P1 C4 103.27(5) . . ?
C9 P1 C7 104.80(5) . . ?
C4 P1 Fe1 116.36(4) . . ?
C7 P1 Fe1 115.34(4) . . ?
C7 P1 C4 99.52(5) . . ?
C4 N1 C5 111.11(8) . . ?
C4 N1 C6 110.07(9) . . ?
C6 N1 C5 109.14(9) . . ?
P1 C9 H9A 108.0 . . ?
P1 C9 H9B 108.0 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 P1 117.16(8) . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
P1 C4 H4A 109.1 . . ?
P1 C4 H4B 109.1 . . ?
N1 C4 P1 112.67(7) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
P2 C13 H13A 108.7 . . ?
P2 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 P2 114.27(8) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
P2 C11 H11A 108.8 . . ?
P2 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 P2 113.74(8) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P2 C5 H5A 108.8 . . ?
P2 C5 H5B 108.8 . . ?
N1 C5 P2 113.97(7) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 C7 H7A 109.0 . . ?
P1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 P1 113.12(7) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C1 Fe1 178.48(10) . . ?

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
Fe1 P2 C13 C14 46.74(10) . . . . ?
Fe1 P2 C11 C12 54.38(9) . . . . ?
Fe1 P2 C5 N1 54.95(9) . . . . ?
Fe1 P1 C9 C10 179.75(8) . . . . ?
Fe1 P1 C4 N1 -63.11(8) . . . . ?
Fe1 P1 C7 C8 58.59(10) . . . . ?
C9 P1 C4 N1 64.52(8) . . . . ?
C9 P1 C7 C8 -69.57(10) . . . . ?
C4 P1 C9 C10 51.58(10) . . . . ?
C4 P1 C7 C8 -176.14(9) . . . . ?
C4 N1 C5 P2 -72.21(10) . . . . ?
C13 P2 C11 C12 -174.63(8) . . . . ?
C13 P2 C5 N1 -75.65(8) . . . . ?
C11 P2 C13 C14 -82.02(9) . . . . ?
C11 P2 C5 N1 -179.81(8) . . . . ?
C5 P2 C13 C14 176.93(9) . . . . ?
C5 P2 C11 C12 -72.89(9) . . . . ?
C5 N1 C4 P1 76.79(10) . . . . ?
C7 P1 C9 C10 -52.19(10) . . . . ?
C7 P1 C4 N1 172.33(8) . . . . ?
C6 N1 C4 P1 -162.19(8) . . . . ?
C6 N1 C5 P2 166.22(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive
