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#  This CIF contains data from an original supplementary publication
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#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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data_D623

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 F6 Fe N5 O2.50 P'
_chemical_formula_weight         510.17

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3610(14)
_cell_length_b                   8.1428(7)
_cell_length_c                   18.0294(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.916(3)
_cell_angle_gamma                90
_cell_volume                     2107.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4964
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.39

_exptl_crystal_description       Needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.868
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocusing Source'
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40849
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_av_R_equivalents  0.1701
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4849
_reflns_number_gt                2923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2013.6-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0429P)²+10.3187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4849
_refine_ls_number_parameters     293
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.058
_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 0.20225(5) 0.08252(9) 0.72481(4) 0.0163(2) Uani 1 1 d . . . . .
P1 P 0.40260(9) 0.74010(17) 0.92158(8) 0.0229(3) Uani 1 1 d . . . . .
F1 F 0.3539(3) 0.6206(4) 0.9778(2) 0.0514(11) Uani 1 1 d . . . . .
F2 F 0.4520(2) 0.8343(5) 0.9889(2) 0.0487(10) Uani 1 1 d . . . . .
F3 F 0.4508(2) 0.8613(5) 0.8654(2) 0.0504(10) Uani 1 1 d . . . . .
F4 F 0.3537(2) 0.6450(5) 0.8535(2) 0.0506(10) Uani 1 1 d . . . . .
F5 F 0.4900(2) 0.6189(4) 0.91775(19) 0.0401(9) Uani 1 1 d . . . . .
F6 F 0.3148(2) 0.8612(4) 0.92599(19) 0.0356(8) Uani 1 1 d . . . . .
O1 O 0.0172(2) 0.1506(4) 0.77385(19) 0.0219(8) Uani 1 1 d . . . . .
O2 O 0.1050(3) -0.0478(5) 0.5940(2) 0.0480(12) Uani 1 1 d . . . . .
N1 N 0.2344(3) 0.2880(5) 0.6745(2) 0.0154(9) Uani 1 1 d . . . . .
N2 N 0.0900(3) 0.3552(5) 0.7140(2) 0.0188(10) Uani 1 1 d . . . . .
H2N H 0.041(4) 0.416(8) 0.712(3) 0.040(18) Uiso 1 1 d . . . . .
N3 N 0.3262(3) -0.0266(5) 0.7070(2) 0.0230(10) Uani 1 1 d . . . . .
N4 N 0.2609(3) 0.1754(5) 0.8164(2) 0.0211(10) Uani 1 1 d . . . . .
N5 N 0.1668(3) -0.1029(6) 0.7844(2) 0.0243(10) Uani 1 1 d . . . . .
C1 C 0.3144(3) 0.3260(7) 0.6404(3) 0.0215(12) Uani 1 1 d . . . . .
H1 H 0.3623 0.2457 0.6385 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3284(4) 0.4750(6) 0.6089(3) 0.0221(12) Uani 1 1 d . . . . .
H2 H 0.3853 0.4983 0.5858 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2590(4) 0.5929(7) 0.6108(3) 0.0250(12) Uani 1 1 d . . . . .
H3 H 0.2675 0.6968 0.5880 0.030 Uiso 1 1 calc R U . . .
C4 C 0.1775(4) 0.5581(6) 0.6461(3) 0.0221(12) Uani 1 1 d . . . . .
H4 H 0.1294 0.6377 0.6490 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1678(3) 0.4027(6) 0.6773(3) 0.0163(10) Uani 1 1 d . . . . .
C6 C 0.0874(3) 0.1964(6) 0.7430(3) 0.0158(10) Uani 1 1 d . . . . .
C7 C 0.1456(4) 0.0021(7) 0.6446(3) 0.0261(13) Uani 1 1 d . . . . .
C8 C 0.3933(4) -0.0979(7) 0.7016(3) 0.0261(12) Uani 1 1 d . . . . .
C9 C 0.4786(4) -0.1929(9) 0.6931(4) 0.0508(11) Uani 1 1 d . . . . .
H9A H 0.4793 -0.2386 0.6429 0.076 Uiso 1 1 calc R U . . .
H9B H 0.4808 -0.2825 0.7294 0.076 Uiso 1 1 calc R U . . .
H9C H 0.5328 -0.1212 0.7014 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2989(4) 0.2082(7) 0.8705(3) 0.0230(12) Uani 1 1 d . . . . .
C11 C 0.3475(5) 0.2417(9) 0.9411(4) 0.0508(11) Uani 1 1 d . . . . .
H11A H 0.3031 0.2369 0.9812 0.076 Uiso 1 1 calc R U . . .
H11B H 0.3756 0.3512 0.9397 0.076 Uiso 1 1 calc R U . . .
H11C H 0.3964 0.1593 0.9499 0.076 Uiso 1 1 calc R U . . .
C12 C 0.1494(4) -0.2059(8) 0.8224(3) 0.0320(15) Uani 1 1 d . . . . .
C13 C 0.1299(5) -0.3412(9) 0.8736(4) 0.0508(11) Uani 1 1 d . . . . .
H13A H 0.1468 -0.4458 0.8509 0.076 Uiso 1 1 calc R U . . .
H13B H 0.0635 -0.3419 0.8842 0.076 Uiso 1 1 calc R U . . .
H13C H 0.1666 -0.3260 0.9200 0.076 Uiso 1 1 calc R U . . .
O1S O 0.9898(7) 0.9629(8) -0.0059(6) 0.032(2) Uani 0.5 1 d D U P A -1
C1S C 0.8954(10) 0.7333(15) 0.0235(8) 0.042(4) Uani 0.5 1 d D U P A -1
H1SA H 0.8454 0.6932 0.0545 0.063 Uiso 0.5 1 calc R U P A -1
H1SB H 0.9515 0.6670 0.0327 0.063 Uiso 0.5 1 calc R U P A -1
H1SC H 0.8758 0.7248 -0.0289 0.063 Uiso 0.5 1 calc R U P A -1
C2S C 0.9163(8) 0.9116(15) 0.0424(6) 0.032(3) Uani 0.5 1 d D U P A -1
H2SA H 0.8601 0.9802 0.0338 0.039 Uiso 0.5 1 calc R U P A -1
H2SB H 0.9370 0.9221 0.0952 0.039 Uiso 0.5 1 calc R U P A -1
C3S C 1.0106(9) 1.1357(10) 0.0082(7) 0.037(3) Uani 0.5 1 d D U P A -1
H3SA H 1.0251 1.1539 0.0616 0.045 Uiso 0.5 1 calc R U P A -1
H3SB H 0.9567 1.2050 -0.0069 0.045 Uiso 0.5 1 calc R U P A -1
C4S C 1.0938(9) 1.178(2) -0.0370(8) 0.041(4) Uani 0.5 1 d D U P A -1
H4SA H 1.1103 1.2935 -0.0292 0.062 Uiso 0.5 1 calc R U P A -1
H4SB H 1.0785 1.1593 -0.0897 0.062 Uiso 0.5 1 calc R U P A -1
H4SC H 1.1466 1.1083 -0.0215 0.062 Uiso 0.5 1 calc R U P A -1


_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 C7 1.761(6) . ?
Fe1 C6 1.930(5) . ?
Fe1 N5 1.931(5) . ?
Fe1 N1 1.966(4) . ?
Fe1 N4 1.979(5) . ?
Fe1 N3 2.025(4) . ?
P1 F2 1.583(3) . ?
P1 F1 1.585(4) . ?
P1 F3 1.590(4) . ?
P1 F4 1.594(4) . ?
P1 F5 1.600(3) . ?
P1 F6 1.604(3) . ?
O1 C6 1.225(6) . ?
O2 C7 1.141(6) . ?
N1 C5 1.339(6) . ?
N1 C1 1.358(6) . ?
N2 C5 1.373(6) . ?
N2 C6 1.396(6) . ?
N3 C8 1.131(6) . ?
N4 C10 1.133(6) . ?
N5 C12 1.117(7) . ?
C1 C2 1.357(7) . ?
C2 C3 1.384(7) . ?
C3 C4 1.380(7) . ?
C4 C5 1.394(7) . ?
C8 C9 1.461(8) . ?
C10 C11 1.457(8) . ?
C12 C13 1.471(8) . ?
O1S C2S 1.453(8) . ?
O1S C3S 1.458(9) . ?
C1S C2S 1.519(9) . ?
C3S C4S 1.507(9) . ?

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
C7 Fe1 C6 86.8(2) . . ?
C7 Fe1 N5 92.4(2) . . ?
C6 Fe1 N5 92.21(19) . . ?
C7 Fe1 N1 92.7(2) . . ?
C6 Fe1 N1 83.37(18) . . ?
N5 Fe1 N1 173.05(18) . . ?
C7 Fe1 N4 177.6(2) . . ?
C6 Fe1 N4 90.98(19) . . ?
N5 Fe1 N4 87.00(18) . . ?
N1 Fe1 N4 87.71(17) . . ?
C7 Fe1 N3 95.2(2) . . ?
C6 Fe1 N3 177.18(19) . . ?
N5 Fe1 N3 89.70(17) . . ?
N1 Fe1 N3 94.53(17) . . ?
N4 Fe1 N3 87.05(17) . . ?
F2 P1 F1 90.2(2) . . ?
F2 P1 F3 89.7(2) . . ?
F1 P1 F3 179.4(2) . . ?
F2 P1 F4 179.5(2) . . ?
F1 P1 F4 90.1(2) . . ?
F3 P1 F4 90.0(2) . . ?
F2 P1 F5 90.01(18) . . ?
F1 P1 F5 90.7(2) . . ?
F3 P1 F5 89.8(2) . . ?
F4 P1 F5 89.6(2) . . ?
F2 P1 F6 89.81(18) . . ?
F1 P1 F6 88.91(19) . . ?
F3 P1 F6 90.6(2) . . ?
F4 P1 F6 90.58(19) . . ?
F5 P1 F6 179.6(2) . . ?
C5 N1 C1 118.4(4) . . ?
C5 N1 Fe1 113.4(3) . . ?
C1 N1 Fe1 128.2(3) . . ?
C5 N2 C6 118.3(4) . . ?
C8 N3 Fe1 173.8(5) . . ?
C10 N4 Fe1 170.9(4) . . ?
C12 N5 Fe1 175.7(5) . . ?
C2 C1 N1 122.1(5) . . ?
C1 C2 C3 119.6(5) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C4 C5 118.1(5) . . ?
N1 C5 N2 114.6(4) . . ?
N1 C5 C4 122.5(4) . . ?
N2 C5 C4 123.0(5) . . ?
O1 C6 N2 119.0(4) . . ?
O1 C6 Fe1 130.7(4) . . ?
N2 C6 Fe1 110.4(3) . . ?
O2 C7 Fe1 176.9(5) . . ?
N3 C8 C9 178.4(6) . . ?
N4 C10 C11 177.1(6) . . ?
N5 C12 C13 177.9(6) . . ?
C2S O1S C3S 108.8(8) . . ?
O1S C2S C1S 106.4(8) . . ?
O1S C3S C4S 106.7(9) . . ?

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
N2 H2N O1 0.86(6) 2.10(6) 2.868(6) 148(5) 2_556

_refine_diff_density_max         1.064
_refine_diff_density_min         -1.497
_refine_diff_density_rms         0.121

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 983678'
