# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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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_dm13109

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Cl2 Fe N2'
_chemical_formula_weight         421.18

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'
Cl Cl 0.1484 0.1585 '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)/n

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

_cell_length_a                   9.0055(13)
_cell_length_b                   15.940(2)
_cell_length_c                   14.422(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.178(3)
_cell_angle_gamma                90.00
_cell_volume                     2070.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4062
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      32.81

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8417
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23426
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         33.11
_reflns_number_total             7729
_reflns_number_gt                4939
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0375P)²+0.0000P] where P=(Fo²+2Fc²)/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         7729
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.010
_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 0.93286(3) 0.394769(17) 0.18860(2) 0.01788(8) Uani 1 1 d . . .
Cl1 Cl 0.96312(6) 0.50910(3) 0.27585(5) 0.03092(14) Uani 1 1 d . . .
Cl2 Cl 1.06292(6) 0.37760(4) 0.05874(4) 0.03283(14) Uani 1 1 d . . .
N1 N 0.91060(18) 0.28300(10) 0.26584(12) 0.0179(3) Uani 1 1 d . . .
N2 N 0.70075(18) 0.37416(10) 0.18670(13) 0.0184(3) Uani 1 1 d . . .
C1 C 1.0349(2) 0.23208(12) 0.29773(15) 0.0199(4) Uani 1 1 d . . .
C2 C 1.1070(2) 0.25481(13) 0.38125(16) 0.0220(4) Uani 1 1 d . . .
C3 C 1.2257(2) 0.20404(14) 0.40965(17) 0.0268(5) Uani 1 1 d . . .
H3 H 1.2766 0.2170 0.4656 0.032 Uiso 1 1 calc R . .
C4 C 1.2703(2) 0.13585(13) 0.35845(18) 0.0273(5) Uani 1 1 d . . .
H4 H 1.3494 0.1015 0.3801 0.033 Uiso 1 1 calc R . .
C5 C 1.2001(2) 0.11721(13) 0.27534(18) 0.0274(5) Uani 1 1 d . . .
H5 H 1.2342 0.0712 0.2394 0.033 Uiso 1 1 calc R . .
C6 C 1.0799(2) 0.16491(12) 0.24334(16) 0.0224(4) Uani 1 1 d . . .
C7 C 1.0063(2) 0.14068(13) 0.15129(16) 0.0246(5) Uani 1 1 d . . .
H7 H 0.9262 0.1825 0.1380 0.029 Uiso 1 1 calc R . .
C8 C 1.1164(3) 0.14302(16) 0.07109(19) 0.0366(6) Uani 1 1 d . . .
H8A H 1.1953 0.1018 0.0821 0.055 Uiso 1 1 calc R . .
H8B H 1.1600 0.1992 0.0666 0.055 Uiso 1 1 calc R . .
H8C H 1.0647 0.1295 0.0131 0.055 Uiso 1 1 calc R . .
C9 C 0.9343(3) 0.05384(15) 0.1579(2) 0.0389(6) Uani 1 1 d . . .
H9A H 0.8839 0.0408 0.0993 0.058 Uiso 1 1 calc R . .
H9B H 0.8618 0.0536 0.2085 0.058 Uiso 1 1 calc R . .
H9C H 1.0110 0.0116 0.1702 0.058 Uiso 1 1 calc R . .
C10 C 1.0639(3) 0.33065(14) 0.43852(17) 0.0278(5) Uani 1 1 d . . .
H10 H 0.9749 0.3570 0.4088 0.033 Uiso 1 1 calc R . .
C11 C 1.0213(3) 0.30455(18) 0.5359(2) 0.0479(7) Uani 1 1 d . . .
H11A H 0.9421 0.2625 0.5330 0.072 Uiso 1 1 calc R . .
H11B H 0.9864 0.3537 0.5704 0.072 Uiso 1 1 calc R . .
H11C H 1.1081 0.2806 0.5674 0.072 Uiso 1 1 calc R . .
C12 C 1.1876(3) 0.39607(15) 0.4414(2) 0.0399(6) Uani 1 1 d . . .
H12A H 1.1531 0.4458 0.4750 0.060 Uiso 1 1 calc R . .
H12B H 1.2146 0.4119 0.3780 0.060 Uiso 1 1 calc R . .
H12C H 1.2746 0.3725 0.4730 0.060 Uiso 1 1 calc R . .
C13 C 0.7359(3) 0.19326(14) 0.35199(18) 0.0309(5) Uani 1 1 d . . .
H13A H 0.8261 0.1686 0.3787 0.046 Uiso 1 1 calc R . .
H13B H 0.6810 0.1502 0.3176 0.046 Uiso 1 1 calc R . .
H13C H 0.6734 0.2154 0.4018 0.046 Uiso 1 1 calc R . .
C14 C 0.7772(2) 0.26251(12) 0.28807(15) 0.0191(4) Uani 1 1 d . . .
C15 C 0.6560(2) 0.31279(12) 0.24485(15) 0.0199(4) Uani 1 1 d . . .
C16 C 0.5080(2) 0.29630(14) 0.26024(17) 0.0277(5) Uani 1 1 d . . .
H16 H 0.4786 0.2541 0.3029 0.033 Uiso 1 1 calc R . .
C17 C 0.4024(2) 0.34294(15) 0.21187(18) 0.0307(5) Uani 1 1 d . . .
H17 H 0.2996 0.3322 0.2201 0.037 Uiso 1 1 calc R . .
C18 C 0.4483(2) 0.40450(14) 0.15227(18) 0.0292(5) Uani 1 1 d . . .
H18 H 0.3773 0.4365 0.1187 0.035 Uiso 1 1 calc R . .
C19 C 0.5991(2) 0.41993(13) 0.14112(16) 0.0221(4) Uani 1 1 d . . .
C20 C 0.6565(3) 0.48628(14) 0.07667(17) 0.0286(5) Uani 1 1 d . . .
H20A H 0.7484 0.5101 0.1020 0.043 Uiso 1 1 calc R . .
H20B H 0.5820 0.5307 0.0700 0.043 Uiso 1 1 calc R . .
H20C H 0.6765 0.4614 0.0159 0.043 Uiso 1 1 calc R . .


_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 N1 2.1111(16) . ?
Fe1 N2 2.1160(17) . ?
Fe1 Cl2 2.2289(7) . ?
Fe1 Cl1 2.2309(7) . ?
N1 C14 1.286(2) . ?
N1 C1 1.456(3) . ?
N2 C19 1.341(3) . ?
N2 C15 1.351(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.414(3) . ?
C2 C3 1.401(3) . ?
C2 C10 1.515(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.532(3) . ?
C7 C8 1.526(3) . ?
C7 C9 1.532(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.516(4) . ?
C10 C12 1.527(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.486(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.489(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.369(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.501(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
N1 Fe1 N2 77.32(6) . . ?
N1 Fe1 Cl2 113.00(5) . . ?
N2 Fe1 Cl2 119.45(5) . . ?
N1 Fe1 Cl1 113.79(5) . . ?
N2 Fe1 Cl1 104.66(5) . . ?
Cl2 Fe1 Cl1 120.71(3) . . ?
C14 N1 C1 119.81(17) . . ?
C14 N1 Fe1 115.85(13) . . ?
C1 N1 Fe1 124.27(12) . . ?
C19 N2 C15 119.58(17) . . ?
C19 N2 Fe1 126.49(14) . . ?
C15 N2 Fe1 113.63(13) . . ?
C6 C1 C2 122.98(19) . . ?
C6 C1 N1 118.51(19) . . ?
C2 C1 N1 118.49(18) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 C10 119.9(2) . . ?
C1 C2 C10 123.42(18) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.4(2) . . ?
C1 C6 C7 123.89(19) . . ?
C5 C6 C7 118.74(19) . . ?
C8 C7 C9 110.2(2) . . ?
C8 C7 C6 111.73(19) . . ?
C9 C7 C6 110.86(19) . . ?
C8 C7 H7 108.0 . . ?
C9 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 110.63(19) . . ?
C11 C10 C12 110.4(2) . . ?
C2 C10 C12 111.80(19) . . ?
C11 C10 H10 107.9 . . ?
C2 C10 H10 107.9 . . ?
C12 C10 H10 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C13 125.37(19) . . ?
N1 C14 C15 116.29(18) . . ?
C13 C14 C15 118.34(18) . . ?
N2 C15 C16 121.9(2) . . ?
N2 C15 C14 115.46(17) . . ?
C16 C15 C14 122.6(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
N2 C19 C18 120.9(2) . . ?
N2 C19 C20 116.80(18) . . ?
C18 C19 C20 122.3(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
N2 Fe1 N1 C14 -10.37(15) . . . . ?
Cl2 Fe1 N1 C14 -127.25(15) . . . . ?
Cl1 Fe1 N1 C14 90.24(16) . . . . ?
N2 Fe1 N1 C1 172.58(17) . . . . ?
Cl2 Fe1 N1 C1 55.71(17) . . . . ?
Cl1 Fe1 N1 C1 -86.80(16) . . . . ?
N1 Fe1 N2 C19 -176.07(19) . . . . ?
Cl2 Fe1 N2 C19 -66.62(18) . . . . ?
Cl1 Fe1 N2 C19 72.31(18) . . . . ?
N1 Fe1 N2 C15 10.17(14) . . . . ?
Cl2 Fe1 N2 C15 119.61(14) . . . . ?
Cl1 Fe1 N2 C15 -101.46(14) . . . . ?
C14 N1 C1 C6 88.7(2) . . . . ?
Fe1 N1 C1 C6 -94.4(2) . . . . ?
C14 N1 C1 C2 -93.2(2) . . . . ?
Fe1 N1 C1 C2 83.7(2) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
N1 C1 C2 C3 179.79(18) . . . . ?
C6 C1 C2 C10 176.7(2) . . . . ?
N1 C1 C2 C10 -1.3(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C10 C2 C3 C4 -178.5(2) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
N1 C1 C6 C5 179.69(18) . . . . ?
C2 C1 C6 C7 -178.17(19) . . . . ?
N1 C1 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.5(2) . . . . ?
C1 C6 C7 C8 120.8(2) . . . . ?
C5 C6 C7 C8 -59.1(3) . . . . ?
C1 C6 C7 C9 -115.9(2) . . . . ?
C5 C6 C7 C9 64.3(3) . . . . ?
C3 C2 C10 C11 -59.6(3) . . . . ?
C1 C2 C10 C11 121.5(2) . . . . ?
C3 C2 C10 C12 63.9(3) . . . . ?
C1 C2 C10 C12 -115.0(2) . . . . ?
C1 N1 C14 C13 5.5(3) . . . . ?
Fe1 N1 C14 C13 -171.67(17) . . . . ?
C1 N1 C14 C15 -174.03(18) . . . . ?
Fe1 N1 C14 C15 8.8(2) . . . . ?
C19 N2 C15 C16 -1.1(3) . . . . ?
Fe1 N2 C15 C16 173.18(17) . . . . ?
C19 N2 C15 C14 176.74(18) . . . . ?
Fe1 N2 C15 C14 -9.0(2) . . . . ?
N1 C14 C15 N2 0.3(3) . . . . ?
C13 C14 C15 N2 -179.30(19) . . . . ?
N1 C14 C15 C16 178.1(2) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
N2 C15 C16 C17 2.0(3) . . . . ?
C14 C15 C16 C17 -175.6(2) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C15 N2 C19 C18 -0.6(3) . . . . ?
Fe1 N2 C19 C18 -174.05(16) . . . . ?
C15 N2 C19 C20 -179.19(19) . . . . ?
Fe1 N2 C19 C20 7.4(3) . . . . ?
C17 C18 C19 N2 1.3(3) . . . . ?
C17 C18 C19 C20 179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        33.11
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 1013290'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_dm13175_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H35 Cl2 Fe N2 P'
_chemical_formula_weight         605.34

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   12.5511(10)
_cell_length_b                   14.2462(12)
_cell_length_c                   17.4859(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.210(2)
_cell_angle_gamma                90.00
_cell_volume                     3094.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    8627
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.28

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8319
_exptl_absorpt_correction_T_max  0.9436
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31842
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         31.31
_reflns_number_total             10097
_reflns_number_gt                7713
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0449P)²+0.0000P] where P=(Fo²+2Fc²)/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         10097
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.256294(16) 0.235190(14) 0.058645(11) 0.01810(5) Uani 1 1 d . . .
Cl1 Cl 0.37610(3) 0.28885(3) -0.01344(2) 0.03116(9) Uani 1 1 d . . .
Cl2 Cl 0.08988(3) 0.19723(3) 0.00227(2) 0.03509(10) Uani 1 1 d . . .
N1 N 0.22118(9) 0.30757(8) 0.15731(6) 0.0175(2) Uani 1 1 d . . .
N2 N 0.32332(9) 0.14716(7) 0.14952(6) 0.0144(2) Uani 1 1 d . . .
P1 P 0.21200(3) 0.00887(2) 0.275793(19) 0.01705(7) Uani 1 1 d . . .
C1 C 0.14993(16) 0.44238(11) 0.08163(10) 0.0352(4) Uani 1 1 d . . .
H1A H 0.2147 0.4414 0.0562 0.053 Uiso 1 1 calc R . .
H1B H 0.1304 0.5075 0.0910 0.053 Uiso 1 1 calc R . .
H1C H 0.0906 0.4118 0.0483 0.053 Uiso 1 1 calc R . .
C2 C 0.17161(12) 0.39121(10) 0.15681(8) 0.0218(3) Uani 1 1 d . . .
C3 C 0.13970(12) 0.42686(10) 0.22450(9) 0.0243(3) Uani 1 1 d . . .
H3 H 0.1053 0.4863 0.2239 0.029 Uiso 1 1 calc R . .
C4 C 0.15813(12) 0.37596(10) 0.29193(8) 0.0237(3) Uani 1 1 d . . .
H4 H 0.1357 0.3997 0.3378 0.028 Uiso 1 1 calc R . .
C5 C 0.20996(11) 0.28923(10) 0.29245(8) 0.0197(3) Uani 1 1 d . . .
H5 H 0.2242 0.2532 0.3385 0.024 Uiso 1 1 calc R . .
C6 C 0.24008(11) 0.25709(9) 0.22369(7) 0.0154(2) Uani 1 1 d . . .
C7 C 0.29720(10) 0.16626(9) 0.21687(7) 0.0142(2) Uani 1 1 d . . .
C8 C 0.31864(11) 0.10249(9) 0.28522(7) 0.0168(2) Uani 1 1 d . . .
H8A H 0.3170 0.1386 0.3334 0.020 Uiso 1 1 calc R . .
H8B H 0.3907 0.0735 0.2873 0.020 Uiso 1 1 calc R . .
C9 C 0.39461(11) 0.06890(9) 0.14132(7) 0.0161(2) Uani 1 1 d . . .
C10 C 0.35431(12) -0.01221(9) 0.10144(8) 0.0198(3) Uani 1 1 d . . .
C11 C 0.42751(14) -0.08439(11) 0.09329(10) 0.0305(3) Uani 1 1 d . . .
H11 H 0.4027 -0.1400 0.0665 0.037 Uiso 1 1 calc R . .
C12 C 0.53486(14) -0.07648(12) 0.12330(11) 0.0364(4) Uani 1 1 d . . .
H12 H 0.5828 -0.1270 0.1182 0.044 Uiso 1 1 calc R . .
C13 C 0.57273(13) 0.00474(12) 0.16079(10) 0.0305(3) Uani 1 1 d . . .
H13 H 0.6470 0.0096 0.1807 0.037 Uiso 1 1 calc R . .
C14 C 0.50438(11) 0.07995(10) 0.17006(8) 0.0207(3) Uani 1 1 d . . .
C15 C 0.55126(12) 0.17047(11) 0.20641(9) 0.0272(3) Uani 1 1 d . . .
H15 H 0.4899 0.2132 0.2127 0.033 Uiso 1 1 calc R . .
C16 C 0.61707(16) 0.15601(16) 0.28635(10) 0.0462(5) Uani 1 1 d . . .
H16A H 0.5716 0.1270 0.3209 0.069 Uiso 1 1 calc R . .
H16B H 0.6432 0.2168 0.3075 0.069 Uiso 1 1 calc R . .
H16C H 0.6785 0.1150 0.2818 0.069 Uiso 1 1 calc R . .
C17 C 0.62030(17) 0.21913(14) 0.15271(11) 0.0418(4) Uani 1 1 d . . .
H17A H 0.6822 0.1794 0.1465 0.063 Uiso 1 1 calc R . .
H17B H 0.6458 0.2795 0.1751 0.063 Uiso 1 1 calc R . .
H17C H 0.5771 0.2296 0.1022 0.063 Uiso 1 1 calc R . .
C18 C 0.23803(12) -0.02154(10) 0.06491(8) 0.0218(3) Uani 1 1 d . . .
H18 H 0.1966 0.0313 0.0842 0.026 Uiso 1 1 calc R . .
C19 C 0.18616(15) -0.11384(11) 0.08554(10) 0.0337(4) Uani 1 1 d . . .
H19A H 0.2197 -0.1664 0.0618 0.050 Uiso 1 1 calc R . .
H19B H 0.1089 -0.1124 0.0662 0.050 Uiso 1 1 calc R . .
H19C H 0.1967 -0.1217 0.1418 0.050 Uiso 1 1 calc R . .
C20 C 0.22906(16) -0.01254(13) -0.02323(9) 0.0362(4) Uani 1 1 d . . .
H20A H 0.2606 0.0472 -0.0363 0.054 Uiso 1 1 calc R . .
H20B H 0.1531 -0.0146 -0.0460 0.054 Uiso 1 1 calc R . .
H20C H 0.2677 -0.0645 -0.0436 0.054 Uiso 1 1 calc R . .
C21 C 0.09128(11) 0.08117(9) 0.27591(7) 0.0172(2) Uani 1 1 d . . .
C22 C 0.03390(12) 0.10259(10) 0.20310(8) 0.0211(3) Uani 1 1 d . . .
H22 H 0.0552 0.0755 0.1580 0.025 Uiso 1 1 calc R . .
C23 C -0.05371(12) 0.16304(11) 0.19646(9) 0.0266(3) Uani 1 1 d . . .
H23 H -0.0912 0.1782 0.1469 0.032 Uiso 1 1 calc R . .
C24 C -0.08643(12) 0.20131(11) 0.26230(9) 0.0275(3) Uani 1 1 d . . .
H24 H -0.1463 0.2427 0.2578 0.033 Uiso 1 1 calc R . .
C25 C -0.03165(12) 0.17915(10) 0.33467(9) 0.0252(3) Uani 1 1 d . . .
H25 H -0.0549 0.2047 0.3797 0.030 Uiso 1 1 calc R . .
C26 C 0.05692(12) 0.11983(10) 0.34163(8) 0.0208(3) Uani 1 1 d . . .
H26 H 0.0944 0.1054 0.3914 0.025 Uiso 1 1 calc R . .
C27 C 0.23390(11) -0.04282(9) 0.37229(7) 0.0183(3) Uani 1 1 d . . .
C28 C 0.15345(12) -0.10271(10) 0.39230(8) 0.0233(3) Uani 1 1 d . . .
H28 H 0.0873 -0.1084 0.3587 0.028 Uiso 1 1 calc R . .
C29 C 0.16943(14) -0.15362(10) 0.46049(9) 0.0283(3) Uani 1 1 d . . .
H29 H 0.1141 -0.1933 0.4738 0.034 Uiso 1 1 calc R . .
C30 C 0.26619(15) -0.14646(10) 0.50924(9) 0.0297(3) Uani 1 1 d . . .
H30 H 0.2773 -0.1815 0.5559 0.036 Uiso 1 1 calc R . .
C31 C 0.34649(14) -0.08860(11) 0.49012(9) 0.0300(3) Uani 1 1 d . . .
H31 H 0.4131 -0.0843 0.5234 0.036 Uiso 1 1 calc R . .
C32 C 0.32989(12) -0.03651(10) 0.42206(8) 0.0245(3) Uani 1 1 d . . .
H32 H 0.3851 0.0039 0.4096 0.029 Uiso 1 1 calc R . .


_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 N2 2.1032(11) . ?
Fe1 N1 2.1098(11) . ?
Fe1 Cl1 2.2306(4) . ?
Fe1 Cl2 2.2447(5) . ?
N1 C2 1.3436(17) . ?
N1 C6 1.3572(17) . ?
N2 C7 1.2957(16) . ?
N2 C9 1.4495(16) . ?
P1 C27 1.8254(13) . ?
P1 C21 1.8324(14) . ?
P1 C8 1.8800(14) . ?
C1 C2 1.494(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.398(2) . ?
C3 C4 1.375(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3886(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4922(17) . ?
C7 C8 1.4948(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.4059(19) . ?
C9 C14 1.4064(19) . ?
C10 C11 1.400(2) . ?
C10 C18 1.513(2) . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.519(2) . ?
C15 C17 1.532(2) . ?
C15 C16 1.533(2) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.533(2) . ?
C18 C20 1.535(2) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.3970(18) . ?
C21 C22 1.4039(19) . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.385(2) . ?
C27 C28 1.4040(19) . ?
C28 C29 1.386(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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
N2 Fe1 N1 77.37(4) . . ?
N2 Fe1 Cl1 113.71(3) . . ?
N1 Fe1 Cl1 122.07(3) . . ?
N2 Fe1 Cl2 115.77(3) . . ?
N1 Fe1 Cl2 100.77(4) . . ?
Cl1 Fe1 Cl2 119.636(18) . . ?
C2 N1 C6 119.98(11) . . ?
C2 N1 Fe1 125.36(9) . . ?
C6 N1 Fe1 114.14(8) . . ?
C7 N2 C9 119.43(11) . . ?
C7 N2 Fe1 115.83(9) . . ?
C9 N2 Fe1 124.74(8) . . ?
C27 P1 C21 103.95(6) . . ?
C27 P1 C8 101.17(6) . . ?
C21 P1 C8 100.35(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.33(13) . . ?
N1 C2 C1 117.68(12) . . ?
C3 C2 C1 121.97(13) . . ?
C4 C3 C2 120.05(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.57(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.07(13) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 121.99(12) . . ?
N1 C6 C7 114.74(11) . . ?
C5 C6 C7 123.26(12) . . ?
N2 C7 C6 116.20(11) . . ?
N2 C7 C8 123.99(11) . . ?
C6 C7 C8 119.79(11) . . ?
C7 C8 P1 108.45(9) . . ?
C7 C8 H8A 110.0 . . ?
P1 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
P1 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C14 122.28(12) . . ?
C10 C9 N2 119.85(12) . . ?
C14 C9 N2 117.75(11) . . ?
C11 C10 C9 117.35(14) . . ?
C11 C10 C18 120.01(13) . . ?
C9 C10 C18 122.59(12) . . ?
C12 C11 C10 121.40(15) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.05(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 121.51(15) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 117.34(13) . . ?
C13 C14 C15 119.50(13) . . ?
C9 C14 C15 123.08(12) . . ?
C14 C15 C17 110.31(13) . . ?
C14 C15 C16 113.19(14) . . ?
C17 C15 C16 109.98(14) . . ?
C14 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 C19 113.11(13) . . ?
C10 C18 C20 110.16(12) . . ?
C19 C18 C20 109.59(13) . . ?
C10 C18 H18 107.9 . . ?
C19 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.80(13) . . ?
C26 C21 P1 125.10(11) . . ?
C22 C21 P1 116.00(10) . . ?
C23 C22 C21 120.55(13) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.93(14) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.03(14) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.32(14) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.36(13) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C32 C27 C28 118.36(12) . . ?
C32 C27 P1 123.88(11) . . ?
C28 C27 P1 117.18(11) . . ?
C29 C28 C27 120.78(14) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 119.86(14) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.12(14) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.01(15) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 120.87(14) . . ?
C27 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?

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
N2 Fe1 N1 C2 177.59(12) . . . . ?
Cl1 Fe1 N1 C2 67.36(12) . . . . ?
Cl2 Fe1 N1 C2 -68.14(12) . . . . ?
N2 Fe1 N1 C6 -10.75(9) . . . . ?
Cl1 Fe1 N1 C6 -120.98(9) . . . . ?
Cl2 Fe1 N1 C6 103.52(9) . . . . ?
N1 Fe1 N2 C7 11.66(9) . . . . ?
Cl1 Fe1 N2 C7 131.39(9) . . . . ?
Cl2 Fe1 N2 C7 -84.34(9) . . . . ?
N1 Fe1 N2 C9 -168.39(11) . . . . ?
Cl1 Fe1 N2 C9 -48.66(10) . . . . ?
Cl2 Fe1 N2 C9 95.61(10) . . . . ?
C6 N1 C2 C3 0.3(2) . . . . ?
Fe1 N1 C2 C3 171.48(11) . . . . ?
C6 N1 C2 C1 -178.20(14) . . . . ?
Fe1 N1 C2 C1 -7.0(2) . . . . ?
N1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C4 177.84(15) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C2 N1 C6 C5 -0.2(2) . . . . ?
Fe1 N1 C6 C5 -172.37(10) . . . . ?
C2 N1 C6 C7 -179.05(12) . . . . ?
Fe1 N1 C6 C7 8.80(14) . . . . ?
C4 C5 C6 N1 0.4(2) . . . . ?
C4 C5 C6 C7 179.17(13) . . . . ?
C9 N2 C7 C6 169.48(11) . . . . ?
Fe1 N2 C7 C6 -10.57(14) . . . . ?
C9 N2 C7 C8 -12.01(19) . . . . ?
Fe1 N2 C7 C8 167.94(10) . . . . ?
N1 C6 C7 N2 1.08(17) . . . . ?
C5 C6 C7 N2 -177.74(12) . . . . ?
N1 C6 C7 C8 -177.50(11) . . . . ?
C5 C6 C7 C8 3.68(19) . . . . ?
N2 C7 C8 P1 -80.02(14) . . . . ?
C6 C7 C8 P1 98.44(12) . . . . ?
C27 P1 C8 C7 -167.63(9) . . . . ?
C21 P1 C8 C7 -61.02(9) . . . . ?
C7 N2 C9 C10 110.06(14) . . . . ?
Fe1 N2 C9 C10 -69.88(14) . . . . ?
C7 N2 C9 C14 -73.80(15) . . . . ?
Fe1 N2 C9 C14 106.26(12) . . . . ?
C14 C9 C10 C11 2.1(2) . . . . ?
N2 C9 C10 C11 178.10(12) . . . . ?
C14 C9 C10 C18 -175.08(12) . . . . ?
N2 C9 C10 C18 0.88(19) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C18 C10 C11 C12 177.45(15) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 1.5(2) . . . . ?
C12 C13 C14 C15 -175.48(15) . . . . ?
C10 C9 C14 C13 -3.0(2) . . . . ?
N2 C9 C14 C13 -179.00(12) . . . . ?
C10 C9 C14 C15 173.94(13) . . . . ?
N2 C9 C14 C15 -2.10(19) . . . . ?
C13 C14 C15 C17 68.02(18) . . . . ?
C9 C14 C15 C17 -108.81(16) . . . . ?
C13 C14 C15 C16 -55.67(19) . . . . ?
C9 C14 C15 C16 127.50(15) . . . . ?
C11 C10 C18 C19 51.53(18) . . . . ?
C9 C10 C18 C19 -131.32(14) . . . . ?
C11 C10 C18 C20 -71.48(17) . . . . ?
C9 C10 C18 C20 105.66(15) . . . . ?
C27 P1 C21 C26 25.53(13) . . . . ?
C8 P1 C21 C26 -78.85(12) . . . . ?
C27 P1 C21 C22 -158.27(10) . . . . ?
C8 P1 C21 C22 97.35(11) . . . . ?
C26 C21 C22 C23 1.6(2) . . . . ?
P1 C21 C22 C23 -174.82(11) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C23 C24 C25 0.0(2) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C24 C25 C26 C21 -0.6(2) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
P1 C21 C26 C25 175.38(11) . . . . ?
C21 P1 C27 C32 -126.02(12) . . . . ?
C8 P1 C27 C32 -22.27(13) . . . . ?
C21 P1 C27 C28 62.92(12) . . . . ?
C8 P1 C27 C28 166.67(11) . . . . ?
C32 C27 C28 C29 0.5(2) . . . . ?
P1 C27 C28 C29 172.12(11) . . . . ?
C27 C28 C29 C30 -0.8(2) . . . . ?
C28 C29 C30 C31 0.2(2) . . . . ?
C29 C30 C31 C32 0.7(2) . . . . ?
C28 C27 C32 C31 0.3(2) . . . . ?
P1 C27 C32 C31 -170.67(12) . . . . ?
C30 C31 C32 C27 -0.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.31
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1013291'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dm13751

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 Cl2 Fe N2 P'
_chemical_formula_weight         563.26

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   17.631(5)
_cell_length_b                   10.038(3)
_cell_length_c                   16.442(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.334(5)
_cell_angle_gamma                90.00
_cell_volume                     2710.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1149
_cell_measurement_theta_min      4.756
_cell_measurement_theta_max      41.160

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17978
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_av_sigmaI/netI    0.1142
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5022
_reflns_number_gt                3108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0592P)²+9.0196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5022
_refine_ls_number_parameters     336
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.09476(5) 0.58508(9) 0.03050(6) 0.0214(3) Uani 1 1 d . . .
Cl1 Cl 0.16404(11) 0.55728(19) -0.06016(12) 0.0387(5) Uani 1 1 d . . .
Cl2 Cl 0.04560(10) 0.35397(16) 0.02876(12) 0.0322(4) Uani 1 1 d . . .
P1 P 0.33923(11) 0.69864(19) 0.33602(12) 0.0297(4) Uani 1 1 d . . .
N1 N 0.1263(3) 0.7918(5) 0.0600(3) 0.0270(13) Uani 1 1 d . . .
N2 N 0.1588(3) 0.5921(5) 0.1678(3) 0.0222(12) Uani 1 1 d . . .
C1 C 0.1088(5) 0.8903(7) 0.0022(5) 0.0422(19) Uani 1 1 d . . .
H1 H 0.0819 0.8687 -0.0577 0.051 Uiso 1 1 calc R . .
C2 C 0.1271(5) 1.0217(7) 0.0240(5) 0.0398(19) Uani 1 1 d . . .
H2 H 0.1127 1.0895 -0.0193 0.048 Uiso 1 1 calc R . .
C3 C 0.1673(4) 1.0516(7) 0.1110(5) 0.0330(17) Uani 1 1 d . . .
H3 H 0.1805 1.1414 0.1288 0.040 Uiso 1 1 calc R . .
C4 C 0.1881(4) 0.9514(6) 0.1718(5) 0.0296(16) Uani 1 1 d . . .
H4 H 0.2174 0.9709 0.2316 0.035 Uiso 1 1 calc R . .
C5 C 0.1664(4) 0.8225(6) 0.1455(4) 0.0215(14) Uani 1 1 d . . .
C6 C 0.1832(4) 0.7062(6) 0.2043(4) 0.0212(14) Uani 1 1 d . . .
C7 C 0.2277(4) 0.7236(6) 0.3012(4) 0.0256(15) Uani 1 1 d . . .
H7A H 0.2057 0.6593 0.3326 0.031 Uiso 1 1 calc R . .
H7B H 0.2172 0.8144 0.3181 0.031 Uiso 1 1 calc R . .
C8 C 0.1748(4) 0.4733(6) 0.2213(4) 0.0270(15) Uani 1 1 d . . .
C9 C 0.1176(4) 0.4380(6) 0.2595(4) 0.0232(14) Uani 1 1 d . . .
C10 C 0.1340(4) 0.3213(7) 0.3094(4) 0.0331(17) Uani 1 1 d . . .
H10 H 0.0973 0.2932 0.3364 0.040 Uiso 1 1 calc R . .
C11 C 0.2025(5) 0.2465(7) 0.3201(5) 0.0388(19) Uani 1 1 d . . .
H11 H 0.2131 0.1688 0.3555 0.047 Uiso 1 1 calc R . .
C12 C 0.2557(5) 0.2830(7) 0.2799(4) 0.0347(17) Uani 1 1 d . . .
H12 H 0.3024 0.2298 0.2878 0.042 Uiso 1 1 calc R . .
C13 C 0.2420(4) 0.3964(6) 0.2283(4) 0.0273(15) Uani 1 1 d . A .
C14 C 0.2956(5) 0.4298(8) 0.1782(5) 0.0397(19) Uani 1 1 d D . .
C15 C 0.3000(7) 0.3327(11) 0.1106(8) 0.047(3) Uani 0.70 1 d PDU A 1
H15A H 0.3223 0.2480 0.1389 0.070 Uiso 0.70 1 calc PR A 1
H15B H 0.3352 0.3687 0.0816 0.070 Uiso 0.70 1 calc PR A 1
H15C H 0.2452 0.3180 0.0673 0.070 Uiso 0.70 1 calc PR A 1
C15' C 0.3547(16) 0.320(2) 0.181(2) 0.053(5) Uani 0.30 1 d PDU A 2
H15D H 0.3995 0.3210 0.2380 0.080 Uiso 0.30 1 calc PR A 2
H15E H 0.3765 0.3342 0.1348 0.080 Uiso 0.30 1 calc PR A 2
H15F H 0.3267 0.2341 0.1726 0.080 Uiso 0.30 1 calc PR A 2
C16 C 0.0442(4) 0.5232(7) 0.2448(5) 0.0328(17) Uani 1 1 d . . .
H16A H 0.0178 0.5399 0.1813 0.039 Uiso 1 1 calc R . .
H16B H 0.0625 0.6103 0.2735 0.039 Uiso 1 1 calc R . .
C17 C -0.0185(4) 0.4661(8) 0.2778(5) 0.0394(19) Uani 1 1 d . . .
H17A H -0.0404 0.3833 0.2465 0.059 Uiso 1 1 calc R . .
H17B H -0.0628 0.5304 0.2678 0.059 Uiso 1 1 calc R . .
H17C H 0.0069 0.4477 0.3404 0.059 Uiso 1 1 calc R . .
C18 C 0.3581(4) 0.6324(7) 0.4453(5) 0.0369(18) Uani 1 1 d . . .
C19 C 0.3938(7) 0.5069(9) 0.4635(6) 0.077(3) Uani 1 1 d . . .
H19 H 0.4063 0.4605 0.4195 0.093 Uiso 1 1 calc R . .
C20 C 0.4114(9) 0.4487(11) 0.5446(7) 0.106(5) Uani 1 1 d . . .
H20 H 0.4373 0.3641 0.5564 0.127 Uiso 1 1 calc R . .
C21 C 0.3921(6) 0.5114(10) 0.6076(6) 0.067(3) Uani 1 1 d . . .
H21 H 0.4043 0.4711 0.6631 0.081 Uiso 1 1 calc R . .
C22 C 0.3548(5) 0.6331(10) 0.5903(6) 0.053(2) Uani 1 1 d . . .
H22 H 0.3408 0.6779 0.6338 0.064 Uiso 1 1 calc R . .
C23 C 0.3377(5) 0.6909(9) 0.5087(5) 0.048(2) Uani 1 1 d . . .
H23 H 0.3106 0.7745 0.4970 0.058 Uiso 1 1 calc R . .
C24 C 0.3834(4) 0.8670(7) 0.3602(4) 0.0299(16) Uani 1 1 d . . .
C25 C 0.3579(4) 0.9667(7) 0.4030(5) 0.0331(17) Uani 1 1 d . . .
H25 H 0.3120 0.9514 0.4190 0.040 Uiso 1 1 calc R . .
C26 C 0.3979(4) 1.0880(7) 0.4229(5) 0.0407(18) Uani 1 1 d . . .
H26 H 0.3795 1.1553 0.4519 0.049 Uiso 1 1 calc R . .
C27 C 0.4641(5) 1.1097(8) 0.4003(5) 0.046(2) Uani 1 1 d . . .
H27 H 0.4924 1.1922 0.4142 0.055 Uiso 1 1 calc R . .
C28 C 0.4902(5) 1.0126(9) 0.3573(6) 0.053(2) Uani 1 1 d . . .
H28 H 0.5358 1.0288 0.3410 0.063 Uiso 1 1 calc R . .
C29 C 0.4502(4) 0.8917(8) 0.3380(5) 0.0398(19) Uani 1 1 d . . .
H29 H 0.4690 0.8249 0.3090 0.048 Uiso 1 1 calc R . .
H14A H 0.291(6) 0.518(4) 0.157(6) 0.10(4) Uiso 1 1 d D . .
H14B H 0.351(2) 0.431(10) 0.214(5) 0.08(3) Uiso 1 1 d 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 N2 2.127(5) . ?
Fe1 N1 2.157(5) . ?
Fe1 Cl1 2.262(2) . ?
Fe1 Cl2 2.386(2) 3_565 ?
Fe1 Cl2 2.4730(19) . ?
Cl2 Fe1 2.386(2) 3_565 ?
P1 C18 1.830(8) . ?
P1 C24 1.842(7) . ?
P1 C7 1.854(7) . ?
N1 C1 1.327(8) . ?
N1 C5 1.359(8) . ?
N2 C6 1.292(8) . ?
N2 C8 1.447(8) . ?
C1 C2 1.375(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.476(8) . ?
C6 C7 1.508(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.383(9) . ?
C8 C9 1.414(9) . ?
C9 C10 1.399(9) . ?
C9 C16 1.495(9) . ?
C10 C11 1.378(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.499(10) . ?
C14 C15' 1.504(17) . ?
C14 C15 1.500(11) . ?
C14 H14A 0.95(2) . ?
C14 H14B 0.94(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C15' H14B 1.25(10) . ?
C16 C17 1.512(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.354(11) . ?
C18 C19 1.392(11) . ?
C19 C20 1.385(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.356(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(13) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(11) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.377(9) . ?
C24 C25 1.390(10) . ?
C25 C26 1.386(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.366(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(12) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(11) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

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
N2 Fe1 N1 74.66(19) . . ?
N2 Fe1 Cl1 119.90(15) . . ?
N1 Fe1 Cl1 96.30(16) . . ?
N2 Fe1 Cl2 119.74(14) . 3_565 ?
N1 Fe1 Cl2 89.40(15) . 3_565 ?
Cl1 Fe1 Cl2 119.41(8) . 3_565 ?
N2 Fe1 Cl2 95.28(14) . . ?
N1 Fe1 Cl2 164.91(16) . . ?
Cl1 Fe1 Cl2 98.49(7) . . ?
Cl2 Fe1 Cl2 85.91(6) 3_565 . ?
Fe1 Cl2 Fe1 94.09(6) 3_565 . ?
C18 P1 C24 102.1(3) . . ?
C18 P1 C7 98.4(3) . . ?
C24 P1 C7 105.1(3) . . ?
C1 N1 C5 118.0(6) . . ?
C1 N1 Fe1 125.6(5) . . ?
C5 N1 Fe1 116.4(4) . . ?
C6 N2 C8 119.3(5) . . ?
C6 N2 Fe1 118.8(4) . . ?
C8 N2 Fe1 121.9(4) . . ?
N1 C1 C2 123.8(7) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.6(7) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C6 113.8(5) . . ?
C4 C5 C6 124.9(6) . . ?
N2 C6 C5 116.3(5) . . ?
N2 C6 C7 123.4(6) . . ?
C5 C6 C7 120.3(5) . . ?
C6 C7 P1 113.4(4) . . ?
C6 C7 H7A 108.9 . . ?
P1 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
P1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C13 C8 C9 123.4(6) . . ?
C13 C8 N2 118.9(6) . . ?
C9 C8 N2 117.6(6) . . ?
C10 C9 C8 116.3(6) . . ?
C10 C9 C16 123.8(6) . . ?
C8 C9 C16 120.0(6) . . ?
C11 C10 C9 121.0(7) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.9(7) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 117.5(6) . . ?
C8 C13 C14 121.4(6) . . ?
C12 C13 C14 121.0(6) . . ?
C15' C14 C15 47.7(13) . . ?
C15' C14 C13 112.7(13) . . ?
C15 C14 C13 118.3(8) . . ?
C15' C14 H14A 132(7) . . ?
C15 C14 H14A 111(7) . . ?
C13 C14 H14A 115(7) . . ?
C15' C14 H14B 56(6) . . ?
C15 C14 H14B 99(6) . . ?
C13 C14 H14B 112(6) . . ?
H14A C14 H14B 98(8) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15' H15D 109.5 . . ?
C14 C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C14 C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C14 C15' H14B 38.7(11) . . ?
H15D C15' H14B 74.3 . . ?
H15E C15' H14B 107.6 . . ?
H15F C15' H14B 138.4 . . ?
C9 C16 C17 115.4(6) . . ?
C9 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C9 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 117.0(8) . . ?
C23 C18 P1 126.5(6) . . ?
C19 C18 P1 116.5(7) . . ?
C20 C19 C18 120.9(10) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.6(10) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.4(9) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 119.5(9) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 122.4(8) . . ?
C18 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C29 C24 C25 118.1(7) . . ?
C29 C24 P1 116.3(6) . . ?
C25 C24 P1 125.5(5) . . ?
C26 C25 C24 121.4(7) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C27 C26 C25 119.2(8) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C28 120.3(8) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 120.2(8) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 120.8(8) . . ?
C24 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?

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
N2 Fe1 Cl2 Fe1 119.53(15) . . . 3_565 ?
N1 Fe1 Cl2 Fe1 72.2(6) . . . 3_565 ?
Cl1 Fe1 Cl2 Fe1 -119.15(8) . . . 3_565 ?
Cl2 Fe1 Cl2 Fe1 0.0 3_565 . . 3_565 ?
N2 Fe1 N1 C1 179.5(6) . . . . ?
Cl1 Fe1 N1 C1 60.1(6) . . . . ?
Cl2 Fe1 N1 C1 -59.4(6) 3_565 . . . ?
Cl2 Fe1 N1 C1 -131.2(6) . . . . ?
N2 Fe1 N1 C5 -1.7(4) . . . . ?
Cl1 Fe1 N1 C5 -121.0(4) . . . . ?
Cl2 Fe1 N1 C5 119.5(4) 3_565 . . . ?
Cl2 Fe1 N1 C5 47.7(9) . . . . ?
N1 Fe1 N2 C6 2.0(5) . . . . ?
Cl1 Fe1 N2 C6 90.5(5) . . . . ?
Cl2 Fe1 N2 C6 -78.2(5) 3_565 . . . ?
Cl2 Fe1 N2 C6 -166.5(4) . . . . ?
N1 Fe1 N2 C8 -178.7(5) . . . . ?
Cl1 Fe1 N2 C8 -90.2(5) . . . . ?
Cl2 Fe1 N2 C8 101.1(5) 3_565 . . . ?
Cl2 Fe1 N2 C8 12.8(5) . . . . ?
C5 N1 C1 C2 -1.5(11) . . . . ?
Fe1 N1 C1 C2 177.3(6) . . . . ?
N1 C1 C2 C3 1.1(12) . . . . ?
C1 C2 C3 C4 0.8(11) . . . . ?
C2 C3 C4 C5 -2.0(10) . . . . ?
C1 N1 C5 C4 0.1(10) . . . . ?
Fe1 N1 C5 C4 -178.8(5) . . . . ?
C1 N1 C5 C6 -179.9(6) . . . . ?
Fe1 N1 C5 C6 1.2(7) . . . . ?
C3 C4 C5 N1 1.6(10) . . . . ?
C3 C4 C5 C6 -178.4(6) . . . . ?
C8 N2 C6 C5 178.6(5) . . . . ?
Fe1 N2 C6 C5 -2.1(7) . . . . ?
C8 N2 C6 C7 -0.5(9) . . . . ?
Fe1 N2 C6 C7 178.8(4) . . . . ?
N1 C5 C6 N2 0.5(8) . . . . ?
C4 C5 C6 N2 -179.5(6) . . . . ?
N1 C5 C6 C7 179.7(6) . . . . ?
C4 C5 C6 C7 -0.3(9) . . . . ?
N2 C6 C7 P1 85.7(7) . . . . ?
C5 C6 C7 P1 -93.4(6) . . . . ?
C18 P1 C7 C6 -148.8(5) . . . . ?
C24 P1 C7 C6 106.2(5) . . . . ?
C6 N2 C8 C13 -96.7(7) . . . . ?
Fe1 N2 C8 C13 84.0(6) . . . . ?
C6 N2 C8 C9 87.0(7) . . . . ?
Fe1 N2 C8 C9 -92.3(6) . . . . ?
C13 C8 C9 C10 2.8(9) . . . . ?
N2 C8 C9 C10 178.8(5) . . . . ?
C13 C8 C9 C16 -176.7(6) . . . . ?
N2 C8 C9 C16 -0.7(9) . . . . ?
C8 C9 C10 C11 0.1(10) . . . . ?
C16 C9 C10 C11 179.5(6) . . . . ?
C9 C10 C11 C12 -1.6(11) . . . . ?
C10 C11 C12 C13 0.4(11) . . . . ?
C9 C8 C13 C12 -3.9(10) . . . . ?
N2 C8 C13 C12 -179.9(6) . . . . ?
C9 C8 C13 C14 172.9(6) . . . . ?
N2 C8 C13 C14 -3.2(10) . . . . ?
C11 C12 C13 C8 2.3(10) . . . . ?
C11 C12 C13 C14 -174.5(7) . . . . ?
C8 C13 C14 C15' -168.8(15) . . . . ?
C12 C13 C14 C15' 7.9(17) . . . . ?
C8 C13 C14 C15 -115.8(9) . . . . ?
C12 C13 C14 C15 60.8(11) . . . . ?
C10 C9 C16 C17 -7.7(10) . . . . ?
C8 C9 C16 C17 171.7(6) . . . . ?
C24 P1 C18 C23 52.5(8) . . . . ?
C7 P1 C18 C23 -55.0(7) . . . . ?
C24 P1 C18 C19 -130.4(7) . . . . ?
C7 P1 C18 C19 122.1(7) . . . . ?
C23 C18 C19 C20 -3.4(15) . . . . ?
P1 C18 C19 C20 179.2(10) . . . . ?
C18 C19 C20 C21 1.9(19) . . . . ?
C19 C20 C21 C22 0.0(18) . . . . ?
C20 C21 C22 C23 -0.2(15) . . . . ?
C19 C18 C23 C22 3.3(13) . . . . ?
P1 C18 C23 C22 -179.7(6) . . . . ?
C21 C22 C23 C18 -1.5(13) . . . . ?
C18 P1 C24 C29 114.7(6) . . . . ?
C7 P1 C24 C29 -143.0(5) . . . . ?
C18 P1 C24 C25 -61.4(7) . . . . ?
C7 P1 C24 C25 40.8(7) . . . . ?
C29 C24 C25 C26 0.1(10) . . . . ?
P1 C24 C25 C26 176.2(5) . . . . ?
C24 C25 C26 C27 -0.3(11) . . . . ?
C25 C26 C27 C28 0.7(11) . . . . ?
C26 C27 C28 C29 -0.9(12) . . . . ?
C25 C24 C29 C28 -0.4(11) . . . . ?
P1 C24 C29 C28 -176.8(6) . . . . ?
C27 C28 C29 C24 0.8(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.115
_database_code_depnum_ccdc_archive 'CCDC 1013292'
