# Electronic Supplementary Material (ESI) for Dalton Transactions.
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#                                CCDC 
# 
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#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_darkwa126
_audit_creation_date             2014-01-15
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H28 Cl2 Fe N3 O'
_chemical_formula_sum            'C20 H28 Cl2 Fe N3 O'
_chemical_formula_weight         453.20
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.7909(3)
_cell_length_b                   14.1052(5)
_cell_length_c                   19.9130(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2188.28(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    7.882
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.087
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33253
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         71.747
_diffrn_reflns_theta_min         3.840
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3894
_reflns_number_total             4183
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.008(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0424P)²+0.3851P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H4A,H4B} of C4, H10 of C10, H8 of C8, H6 of C6, {H5A,H5B} of C5, H2 of N2,
  H1 of C1, H2A of C2
 At 1.5 times of:
  {H20A,H20B,H20C} of C20, {H19A,H19B,H19C} of C19, {H18A,H18B,H18C} of C18,
  {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H14A,H14B,H14C} of C14
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C6(H6), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.13588(6) 0.56389(3) 0.28588(2) 0.01602(13) Uani 1 1 d . . . . .
Cl1 Cl -0.25966(10) 0.69446(5) 0.33715(4) 0.02326(18) Uani 1 1 d . . . . .
Cl2 Cl -0.00350(10) 0.63903(6) 0.19893(4) 0.02517(19) Uani 1 1 d . . . . .
O1 O 0.0082(3) 0.54461(15) 0.35915(11) 0.0213(5) Uani 1 1 d . . . . .
N1 N -0.3766(3) 0.51600(18) 0.25368(13) 0.0186(6) Uani 1 1 d . . . . .
N2 N -0.6424(4) 0.5299(2) 0.21980(14) 0.0239(6) Uani 1 1 d . . . . .
H2 H -0.7460 0.5533 0.2141 0.029 Uiso 1 1 calc R U . . .
N3 N -0.0419(3) 0.43098(19) 0.25088(13) 0.0173(6) Uani 1 1 d . . . . .
C1 C -0.5180(4) 0.5695(2) 0.25531(17) 0.0219(7) Uani 1 1 d . . . . .
H1 H -0.5280 0.6279 0.2787 0.026 Uiso 1 1 calc R U . . .
C2 C -0.5827(4) 0.4464(3) 0.19344(17) 0.0243(7) Uani 1 1 d . . . . .
H2A H -0.6444 0.4032 0.1659 0.029 Uiso 1 1 calc R U . . .
C3 C -0.4187(4) 0.4377(2) 0.21437(16) 0.0204(6) Uani 1 1 d . . . . .
C4 C -0.2966(4) 0.3581(2) 0.19983(18) 0.0252(7) Uani 1 1 d . . . . .
H4A H -0.3366 0.3235 0.1595 0.030 Uiso 1 1 calc R U . . .
H4B H -0.2977 0.3131 0.2380 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1135(4) 0.3920(2) 0.18818(17) 0.0229(7) Uani 1 1 d . . . . .
H5A H -0.0418 0.3384 0.1726 0.027 Uiso 1 1 calc R U . . .
H5B H -0.1125 0.4414 0.1529 0.027 Uiso 1 1 calc R U . . .
C6 C 0.0783(4) 0.3819(2) 0.27868(17) 0.0183(7) Uani 1 1 d . . . . .
H6 H 0.1085 0.3241 0.2572 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1716(4) 0.4057(2) 0.33894(16) 0.0181(6) Uani 1 1 d . . . . .
C8 C 0.3093(4) 0.3465(2) 0.35702(16) 0.0202(7) Uani 1 1 d . . . . .
H8 H 0.3312 0.2909 0.3315 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4130(4) 0.3673(2) 0.41083(17) 0.0207(7) Uani 1 1 d . . . . .
C10 C 0.3729(4) 0.4487(2) 0.44745(16) 0.0216(7) Uani 1 1 d . . . . .
H10 H 0.4434 0.4635 0.4849 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2386(4) 0.5096(2) 0.43338(16) 0.0202(7) Uani 1 1 d . . . . .
C12 C 0.1353(4) 0.4875(2) 0.37671(16) 0.0182(6) Uani 1 1 d . . . . .
C13 C 0.5733(4) 0.3090(3) 0.42936(18) 0.0252(8) Uani 1 1 d . . . . .
C14 C 0.5744(6) 0.2139(3) 0.3961(3) 0.0531(13) Uani 1 1 d . . . . .
H14A H 0.6789 0.1796 0.4088 0.080 Uiso 1 1 calc R U . . .
H14B H 0.5715 0.2221 0.3472 0.080 Uiso 1 1 calc R U . . .
H14C H 0.4736 0.1777 0.4105 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7308(5) 0.3664(3) 0.4052(2) 0.0435(11) Uani 1 1 d . . . . .
H15A H 0.7327 0.4280 0.4279 0.065 Uiso 1 1 calc R U . . .
H15B H 0.7234 0.3760 0.3566 0.065 Uiso 1 1 calc R U . . .
H15C H 0.8360 0.3315 0.4159 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5878(5) 0.2967(3) 0.5053(2) 0.0393(10) Uani 1 1 d . . . . .
H16A H 0.6052 0.3588 0.5264 0.059 Uiso 1 1 calc R U . . .
H16B H 0.6855 0.2554 0.5157 0.059 Uiso 1 1 calc R U . . .
H16C H 0.4821 0.2681 0.5226 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2045(5) 0.5988(2) 0.47563(17) 0.0237(8) Uani 1 1 d . . . . .
C18 C 0.3343(5) 0.6076(3) 0.53381(18) 0.0307(9) Uani 1 1 d . . . . .
H18A H 0.3076 0.6641 0.5604 0.046 Uiso 1 1 calc R U . . .
H18B H 0.4506 0.6131 0.5155 0.046 Uiso 1 1 calc R U . . .
H18C H 0.3270 0.5512 0.5624 0.046 Uiso 1 1 calc R U . . .
C19 C 0.2243(5) 0.6875(3) 0.43172(19) 0.0312(8) Uani 1 1 d . . . . .
H19A H 0.2029 0.7442 0.4589 0.047 Uiso 1 1 calc R U . . .
H19B H 0.1416 0.6850 0.3947 0.047 Uiso 1 1 calc R U . . .
H19C H 0.3411 0.6899 0.4135 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0229(5) 0.5951(3) 0.50592(18) 0.0302(8) Uani 1 1 d . . . . .
H20A H 0.0128 0.5395 0.5351 0.045 Uiso 1 1 calc R U . . .
H20B H -0.0619 0.5909 0.4697 0.045 Uiso 1 1 calc R U . . .
H20C H 0.0022 0.6527 0.5322 0.045 Uiso 1 1 calc 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 Cl1 2.3161(9) . ?
Fe1 Cl2 2.2770(9) . ?
Fe1 O1 1.861(2) . ?
Fe1 N1 2.094(3) . ?
Fe1 N3 2.130(3) . ?
O1 C12 1.324(4) . ?
N1 C1 1.336(4) . ?
N1 C3 1.393(4) . ?
N2 H2 0.8800 . ?
N2 C1 1.322(4) . ?
N2 C2 1.371(5) . ?
N3 C5 1.474(4) . ?
N3 C6 1.289(4) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.349(5) . ?
C3 C4 1.499(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.523(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.443(4) . ?
C7 C8 1.407(4) . ?
C7 C12 1.406(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(5) . ?
C9 C10 1.396(5) . ?
C9 C13 1.540(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(5) . ?
C11 C12 1.421(5) . ?
C11 C17 1.536(5) . ?
C13 C14 1.497(6) . ?
C13 C15 1.546(5) . ?
C13 C16 1.527(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.543(5) . ?
C17 C19 1.534(5) . ?
C17 C20 1.539(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
Cl2 Fe1 Cl1 98.84(3) . . ?
O1 Fe1 Cl1 91.25(7) . . ?
O1 Fe1 Cl2 113.02(8) . . ?
O1 Fe1 N1 137.16(11) . . ?
O1 Fe1 N3 85.44(10) . . ?
N1 Fe1 Cl1 91.07(8) . . ?
N1 Fe1 Cl2 108.85(8) . . ?
N1 Fe1 N3 85.63(10) . . ?
N3 Fe1 Cl1 170.86(8) . . ?
N3 Fe1 Cl2 90.30(7) . . ?
C12 O1 Fe1 138.4(2) . . ?
C1 N1 Fe1 123.3(2) . . ?
C1 N1 C3 105.5(3) . . ?
C3 N1 Fe1 129.7(2) . . ?
C1 N2 H2 125.7 . . ?
C1 N2 C2 108.6(3) . . ?
C2 N2 H2 125.7 . . ?
C5 N3 Fe1 118.4(2) . . ?
C6 N3 Fe1 125.6(2) . . ?
C6 N3 C5 116.0(3) . . ?
N1 C1 H1 124.7 . . ?
N2 C1 N1 110.7(3) . . ?
N2 C1 H1 124.7 . . ?
N2 C2 H2A 126.8 . . ?
C3 C2 N2 106.3(3) . . ?
C3 C2 H2A 126.8 . . ?
N1 C3 C4 123.6(3) . . ?
C2 C3 N1 108.9(3) . . ?
C2 C3 C4 127.5(3) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.8(3) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
N3 C5 C4 110.0(3) . . ?
N3 C5 H5A 109.7 . . ?
N3 C5 H5B 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N3 C6 H6 116.6 . . ?
N3 C6 C7 126.8(3) . . ?
C7 C6 H6 116.6 . . ?
C8 C7 C6 117.4(3) . . ?
C12 C7 C6 122.3(3) . . ?
C12 C7 C8 120.3(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 116.9(3) . . ?
C8 C9 C13 123.4(3) . . ?
C10 C9 C13 119.7(3) . . ?
C9 C10 H10 117.5 . . ?
C11 C10 C9 125.1(3) . . ?
C11 C10 H10 117.5 . . ?
C10 C11 C12 116.9(3) . . ?
C10 C11 C17 121.9(3) . . ?
C12 C11 C17 121.2(3) . . ?
O1 C12 C7 120.6(3) . . ?
O1 C12 C11 120.0(3) . . ?
C7 C12 C11 119.4(3) . . ?
C9 C13 C15 106.9(3) . . ?
C14 C13 C9 112.2(3) . . ?
C14 C13 C15 109.1(4) . . ?
C14 C13 C16 109.6(3) . . ?
C16 C13 C9 111.0(3) . . ?
C16 C13 C15 108.0(3) . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 C18 111.4(3) . . ?
C11 C17 C20 110.3(3) . . ?
C19 C17 C11 109.8(3) . . ?
C19 C17 C18 107.2(3) . . ?
C19 C17 C20 110.1(3) . . ?
C20 C17 C18 108.1(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 H2 Cl2 0.88 2.36 3.234(3) 171.2 1_455

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 O1 C12 C7 -12.5(5) . . . . ?
Fe1 O1 C12 C11 166.2(2) . . . . ?
Fe1 N1 C1 N2 167.0(2) . . . . ?
Fe1 N1 C3 C2 -165.9(2) . . . . ?
Fe1 N1 C3 C4 14.6(5) . . . . ?
Fe1 N3 C5 C4 -71.8(3) . . . . ?
Fe1 N3 C6 C7 0.9(5) . . . . ?
Cl1 Fe1 O1 C12 -176.3(3) . . . . ?
Cl2 Fe1 O1 C12 -76.1(3) . . . . ?
N1 Fe1 O1 C12 90.8(3) . . . . ?
N1 C3 C4 C5 -38.7(5) . . . . ?
N2 C2 C3 N1 -0.1(4) . . . . ?
N2 C2 C3 C4 179.4(3) . . . . ?
N3 Fe1 O1 C12 12.3(3) . . . . ?
N3 C6 C7 C8 -174.0(3) . . . . ?
N3 C6 C7 C12 2.2(5) . . . . ?
C1 N1 C3 C2 0.2(4) . . . . ?
C1 N1 C3 C4 -179.3(3) . . . . ?
C1 N2 C2 C3 -0.1(4) . . . . ?
C2 N2 C1 N1 0.3(4) . . . . ?
C2 C3 C4 C5 141.9(3) . . . . ?
C3 N1 C1 N2 -0.3(4) . . . . ?
C3 C4 C5 N3 67.2(4) . . . . ?
C5 N3 C6 C7 178.3(3) . . . . ?
C6 N3 C5 C4 110.5(3) . . . . ?
C6 C7 C8 C9 175.3(3) . . . . ?
C6 C7 C12 O1 2.4(5) . . . . ?
C6 C7 C12 C11 -176.4(3) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C7 C8 C9 C13 -175.2(3) . . . . ?
C8 C7 C12 O1 178.5(3) . . . . ?
C8 C7 C12 C11 -0.2(5) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C13 C14 -16.7(5) . . . . ?
C8 C9 C13 C15 102.7(4) . . . . ?
C8 C9 C13 C16 -139.8(4) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C9 C10 C11 C17 -179.1(3) . . . . ?
C10 C9 C13 C14 166.9(4) . . . . ?
C10 C9 C13 C15 -73.6(4) . . . . ?
C10 C9 C13 C16 43.9(5) . . . . ?
C10 C11 C12 O1 -177.7(3) . . . . ?
C10 C11 C12 C7 1.0(5) . . . . ?
C10 C11 C17 C18 -1.2(5) . . . . ?
C10 C11 C17 C19 117.4(4) . . . . ?
C10 C11 C17 C20 -121.2(3) . . . . ?
C12 C7 C8 C9 -1.0(5) . . . . ?
C12 C11 C17 C18 -179.5(3) . . . . ?
C12 C11 C17 C19 -60.9(4) . . . . ?
C12 C11 C17 C20 60.5(4) . . . . ?
C13 C9 C10 C11 176.2(3) . . . . ?
C17 C11 C12 O1 0.7(5) . . . . ?
C17 C11 C12 C7 179.4(3) . . . . ?

_shelx_estimated_absorpt_T_max   0.547
_shelx_estimated_absorpt_T_min   0.290
_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.
;
_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 998101'
#######################################################################
#
#                 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_darkwa140

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 Br2 Fe N3 O'
_chemical_formula_sum            'C20 H28 Br2 Fe N3 O'
_chemical_formula_weight         542.12

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'
Br Br -0.2901 2.4595 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21  '
_symmetry_space_group_name_Hall  'P 2ac 2ab   '
_symmetry_int_tables_number      19

_chemical_absolute_configuration ad
# Options are 'rm', 'ad', 'rmad', 'syn', 'unk' or '.'
#                      
# rm   : absolute configuration established by the structure determination
#        of a compound containing a chiral reference molecule of known
#        absolute configuration.
# ad   : absolute configuration established by anomalous dispersion effects
#        in diffraction measurements on the crystal.
# rmad : absolute configuration established by the structure determination
#        of a compound containing a chiral reference molecule of known
#        absolute configuration and confirmed by anomalous dispersion
#        effects in diffraction measurements on the crystal.
# syn  : absolute configuration has not been established by anomalous
#        dispersion effects in diffraction measurements on the crystal.
#        The enantiomer has been assigned by reference to an unchanging
#        chiral centre in the synthetic procedure.
# unk  : absolute configuration is unknown, there being no firm chemical
#        evidence for its assignment to hand and it having not been 
#        established by anomalous dispersion effects in diffraction 
#        measurements on the crystal. An arbitrary choice of enantiomer
#        has been made.
# .    : inapplicable.
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.931(2)
_cell_length_b                   14.457(4)
_cell_length_c                   20.040(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2297.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      2.4731
_cell_measurement_theta_max      26.3385

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    4.148
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min  0.4359
_exptl_absorpt_correction_T_max  0.5750

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5° φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48840
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         26.44
_reflns_number_total             4685
_reflns_number_gt                4413
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 Ver. 2010.11-3 (Bruker-AXS, 2010)'
_computing_cell_refinement       'SAINT Ver. 7.68A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.68A'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0310P)²+1.2605P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_number_reflns         4685
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Br1 Br 0.00100(5) 0.86433(2) 0.305161(18) 0.05837(10) Uani 1 1 d . . .
Br2 Br 0.26663(4) 0.81076(2) 0.15718(2) 0.05672(10) Uani 1 1 d . . .
Fe1 Fe 0.13726(5) 0.94464(3) 0.214293(19) 0.03404(9) Uani 1 1 d . . .
O1 O -0.0063(3) 0.96224(13) 0.14259(10) 0.0445(5) Uani 1 1 d . . .
N1 N 0.0439(3) 1.07368(16) 0.24931(11) 0.0359(5) Uani 1 1 d . . .
N2 N 0.3725(3) 0.99110(17) 0.24804(13) 0.0414(5) Uani 1 1 d . . .
N3 N 0.6329(3) 0.9802(2) 0.28205(15) 0.0545(7) Uani 1 1 d . . .
H3 H 0.7329 0.9587 0.2879 0.065 Uiso 1 1 calc R . .
C1 C -0.1317(4) 1.01708(18) 0.12522(13) 0.0343(5) Uani 1 1 d . . .
C2 C -0.2347(4) 0.9946(2) 0.06905(14) 0.0398(6) Uani 1 1 d . . .
C3 C -0.3656(4) 1.0539(2) 0.05488(14) 0.0437(6) Uani 1 1 d . . .
H3A H -0.4342 1.0392 0.0187 0.052 Uiso 1 1 calc R . .
C4 C -0.4041(4) 1.1347(2) 0.09060(15) 0.0406(6) Uani 1 1 d . . .
C5 C -0.3027(4) 1.1548(2) 0.14446(15) 0.0396(6) Uani 1 1 d . . .
H5 H -0.3238 1.2076 0.1696 0.048 Uiso 1 1 calc R . .
C6 C -0.1681(3) 1.09690(19) 0.16207(14) 0.0349(6) Uani 1 1 d . . .
C7 C -0.0755(4) 1.12015(18) 0.22162(15) 0.0361(6) Uani 1 1 d . . .
H7 H -0.1055 1.1752 0.2425 0.043 Uiso 1 1 calc R . .
C8 C -0.2011(5) 0.9073(2) 0.02769(16) 0.0511(8) Uani 1 1 d . . .
C9 C -0.0242(6) 0.9121(3) -0.00280(19) 0.0722(11) Uani 1 1 d . . .
H9A H -0.0157 0.9659 -0.0307 0.108 Uiso 1 1 calc R . .
H9B H -0.0040 0.8577 -0.0290 0.108 Uiso 1 1 calc R . .
H9C H 0.0581 0.9159 0.0322 0.108 Uiso 1 1 calc R . .
C10 C -0.2196(6) 0.8214(3) 0.0712(2) 0.0711(11) Uani 1 1 d . . .
H10A H -0.1448 0.8260 0.1087 0.107 Uiso 1 1 calc R . .
H10B H -0.1918 0.7675 0.0455 0.107 Uiso 1 1 calc R . .
H10C H -0.3337 0.8168 0.0867 0.107 Uiso 1 1 calc R . .
C11 C -0.3294(6) 0.8982(3) -0.0301(2) 0.0760(13) Uani 1 1 d . . .
H11A H -0.4404 0.8892 -0.0121 0.114 Uiso 1 1 calc R . .
H11B H -0.2997 0.8462 -0.0575 0.114 Uiso 1 1 calc R . .
H11C H -0.3278 0.9536 -0.0565 0.114 Uiso 1 1 calc R . .
C12 C -0.5600(4) 1.1920(3) 0.07215(17) 0.0511(8) Uani 1 1 d . . .
C13 C -0.5708(5) 1.2054(4) -0.0025(2) 0.0782(14) Uani 1 1 d . . .
H13A H -0.4679 1.2326 -0.0185 0.117 Uiso 1 1 calc R . .
H13B H -0.6637 1.2455 -0.0128 0.117 Uiso 1 1 calc R . .
H13C H -0.5875 1.1466 -0.0238 0.117 Uiso 1 1 calc R . .
C14 C -0.7154(5) 1.1383(4) 0.0953(2) 0.0827(14) Uani 1 1 d . . .
H14A H -0.7099 1.0761 0.0786 0.124 Uiso 1 1 calc R . .
H14B H -0.8153 1.1679 0.0787 0.124 Uiso 1 1 calc R . .
H14C H -0.7186 1.1371 0.1432 0.124 Uiso 1 1 calc R . .
C15 C -0.5589(7) 1.2850(3) 0.1051(3) 0.1009(19) Uani 1 1 d . . .
H15A H -0.5647 1.2773 0.1527 0.151 Uiso 1 1 calc R . .
H15B H -0.6543 1.3202 0.0902 0.151 Uiso 1 1 calc R . .
H15C H -0.4569 1.3171 0.0937 0.151 Uiso 1 1 calc R . .
C16 C 0.1133(4) 1.1124(2) 0.31116(16) 0.0492(8) Uani 1 1 d . . .
H16A H 0.1118 1.0656 0.3459 0.059 Uiso 1 1 calc R . .
H16B H 0.0440 1.1639 0.3258 0.059 Uiso 1 1 calc R . .
C17 C 0.2913(5) 1.1450(3) 0.30014(18) 0.0553(8) Uani 1 1 d . . .
H17A H 0.2926 1.1878 0.2629 0.066 Uiso 1 1 calc R . .
H17B H 0.3286 1.1784 0.3394 0.066 Uiso 1 1 calc R . .
C18 C 0.4127(4) 1.0685(2) 0.28636(15) 0.0442(7) Uani 1 1 d . . .
C19 C 0.5725(4) 1.0602(3) 0.30753(18) 0.0553(8) Uani 1 1 d . . .
H19 H 0.6307 1.1016 0.3346 0.066 Uiso 1 1 calc R . .
C20 C 0.5123(4) 0.9406(2) 0.24670(17) 0.0502(7) Uani 1 1 d . . .
H20 H 0.5237 0.8849 0.2240 0.060 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
Br1 Fe1 2.4150(7) . yes
Br2 Fe1 2.4717(7) . yes
Fe1 O1 1.851(2) . yes
Fe1 N2 2.095(3) . yes
Fe1 N1 2.126(2) . yes
O1 C1 1.319(3) . ?
N1 C7 1.286(4) . ?
N1 C16 1.467(4) . ?
N2 C20 1.328(4) . ?
N2 C18 1.394(4) . ?
N3 C20 1.321(4) . ?
N3 C19 1.352(5) . ?
N3 H3 0.8600 . ?
C1 C6 1.400(4) . ?
C1 C2 1.428(4) . ?
C2 C3 1.376(4) . ?
C2 C8 1.533(4) . ?
C3 C4 1.404(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C12 1.533(4) . ?
C5 C6 1.402(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(4) . ?
C7 H7 0.9300 . ?
C8 C10 1.524(5) . ?
C8 C9 1.532(6) . ?
C8 C11 1.547(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.498(6) . ?
C12 C13 1.512(5) . ?
C12 C14 1.529(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.505(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.492(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.342(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 N2 138.96(10) . . yes
O1 Fe1 N1 85.49(9) . . yes
N2 Fe1 N1 85.54(9) . . yes
O1 Fe1 Br1 112.10(8) . . yes
N2 Fe1 Br1 108.01(7) . . yes
N1 Fe1 Br1 90.98(7) . . yes
O1 Fe1 Br2 90.20(6) . . yes
N2 Fe1 Br2 91.78(7) . . yes
N1 Fe1 Br2 169.90(7) . . yes
Br1 Fe1 Br2 99.11(3) . . yes
C1 O1 Fe1 138.72(17) . . ?
C7 N1 C16 116.2(2) . . ?
C7 N1 Fe1 124.90(19) . . ?
C16 N1 Fe1 118.87(18) . . ?
C20 N2 C18 105.1(3) . . ?
C20 N2 Fe1 124.1(2) . . ?
C18 N2 Fe1 129.7(2) . . ?
C20 N3 C19 108.5(3) . . ?
C20 N3 H3 125.8 . . ?
C19 N3 H3 125.8 . . ?
O1 C1 C6 120.8(2) . . ?
O1 C1 C2 120.2(2) . . ?
C6 C1 C2 119.1(3) . . ?
C3 C2 C1 116.9(3) . . ?
C3 C2 C8 122.1(3) . . ?
C1 C2 C8 120.9(3) . . ?
C2 C3 C4 125.2(3) . . ?
C2 C3 H3A 117.4 . . ?
C4 C3 H3A 117.4 . . ?
C5 C4 C3 116.6(3) . . ?
C5 C4 C12 123.1(3) . . ?
C3 C4 C12 120.1(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 C7 121.6(2) . . ?
C5 C6 C7 117.2(3) . . ?
N1 C7 C6 127.6(3) . . ?
N1 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C10 C8 C9 110.7(3) . . ?
C10 C8 C2 110.2(3) . . ?
C9 C8 C2 109.7(3) . . ?
C10 C8 C11 107.2(3) . . ?
C9 C8 C11 107.9(3) . . ?
C2 C8 C11 111.1(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C13 108.8(4) . . ?
C15 C12 C14 109.1(4) . . ?
C13 C12 C14 108.7(4) . . ?
C15 C12 C4 112.0(3) . . ?
C13 C12 C4 110.7(3) . . ?
C14 C12 C4 107.6(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 110.3(3) . . ?
N1 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 113.6(3) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 N2 108.6(3) . . ?
C19 C18 C17 128.1(3) . . ?
N2 C18 C17 123.3(3) . . ?
C18 C19 N3 107.0(3) . . ?
C18 C19 H19 126.5 . . ?
N3 C19 H19 126.5 . . ?
N3 C20 N2 110.8(3) . . ?
N3 C20 H20 124.6 . . ?
N2 C20 H20 124.6 . . ?

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 O1 C1 -89.7(3) . . . . ?
N1 Fe1 O1 C1 -11.7(3) . . . . ?
Br1 Fe1 O1 C1 77.5(3) . . . . ?
Br2 Fe1 O1 C1 177.4(3) . . . . ?
O1 Fe1 N1 C7 5.3(2) . . . . ?
N2 Fe1 N1 C7 145.2(2) . . . . ?
Br1 Fe1 N1 C7 -106.8(2) . . . . ?
Br2 Fe1 N1 C7 70.3(5) . . . . ?
O1 Fe1 N1 C16 -177.5(2) . . . . ?
N2 Fe1 N1 C16 -37.6(2) . . . . ?
Br1 Fe1 N1 C16 70.4(2) . . . . ?
Br2 Fe1 N1 C16 -112.5(4) . . . . ?
O1 Fe1 N2 C20 -106.1(3) . . . . ?
N1 Fe1 N2 C20 176.0(3) . . . . ?
Br1 Fe1 N2 C20 86.4(3) . . . . ?
Br2 Fe1 N2 C20 -13.7(2) . . . . ?
O1 Fe1 N2 C18 87.3(3) . . . . ?
N1 Fe1 N2 C18 9.4(3) . . . . ?
Br1 Fe1 N2 C18 -80.2(3) . . . . ?
Br2 Fe1 N2 C18 179.6(3) . . . . ?
Fe1 O1 C1 C6 12.2(5) . . . . ?
Fe1 O1 C1 C2 -166.5(2) . . . . ?
O1 C1 C2 C3 178.5(3) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
O1 C1 C2 C8 -0.5(4) . . . . ?
C6 C1 C2 C8 -179.3(3) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C8 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C2 C3 C4 C12 -176.5(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C12 C4 C5 C6 175.7(3) . . . . ?
O1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
O1 C1 C6 C7 -2.7(4) . . . . ?
C2 C1 C6 C7 176.1(3) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -176.1(3) . . . . ?
C16 N1 C7 C6 -178.3(3) . . . . ?
Fe1 N1 C7 C6 -1.0(4) . . . . ?
C1 C6 C7 N1 -1.7(4) . . . . ?
C5 C6 C7 N1 174.8(3) . . . . ?
C3 C2 C8 C10 -117.7(4) . . . . ?
C1 C2 C8 C10 61.2(4) . . . . ?
C3 C2 C8 C9 120.2(3) . . . . ?
C1 C2 C8 C9 -60.9(4) . . . . ?
C3 C2 C8 C11 0.9(5) . . . . ?
C1 C2 C8 C11 179.8(3) . . . . ?
C5 C4 C12 C15 17.1(5) . . . . ?
C3 C4 C12 C15 -167.4(4) . . . . ?
C5 C4 C12 C13 138.7(4) . . . . ?
C3 C4 C12 C13 -45.8(4) . . . . ?
C5 C4 C12 C14 -102.7(4) . . . . ?
C3 C4 C12 C14 72.8(4) . . . . ?
C7 N1 C16 C17 -111.6(3) . . . . ?
Fe1 N1 C16 C17 70.9(3) . . . . ?
N1 C16 C17 C18 -67.0(4) . . . . ?
C20 N2 C18 C19 -1.4(4) . . . . ?
Fe1 N2 C18 C19 167.2(2) . . . . ?
C20 N2 C18 C17 179.1(3) . . . . ?
Fe1 N2 C18 C17 -12.3(5) . . . . ?
C16 C17 C18 C19 -141.6(4) . . . . ?
C16 C17 C18 N2 37.8(5) . . . . ?
N2 C18 C19 N3 1.2(4) . . . . ?
C17 C18 C19 N3 -179.4(3) . . . . ?
C20 N3 C19 C18 -0.5(4) . . . . ?
C19 N3 C20 N2 -0.5(4) . . . . ?
C18 N2 C20 N3 1.1(4) . . . . ?
Fe1 N2 C20 N3 -168.2(2) . . . . ?

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
N3 H3 Br1 0.86 2.55 3.397(3) 168.8 1_655

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.052
_iucr_refine_instruction_details 
;
TITL DARKWA140 IN P2(1)2(1)2(1)
CELL 0.71073 7.9309 14.4575 20.0398 90 90 90
ZERR 4 0.0024 0.0042 0.0069 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br Fe N O
UNIT 80 112 8 4 12 4
EQIV $1 1+X,+Y,+Z
L.S. 12
PLAN  5
SIZE 0.24 0.19 0.15
TEMP 23
HTAB  N3 Br1_$1
LIST 4
BOND $H
CONF
HTAB
WPDB -2
fmap 2
acta 50
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT 0 15 6
OMIT 0 6 12
OMIT 3 0 3
OMIT 0 7 7
OMIT 6 3 9
OMIT 3 3 3
OMIT -6 3 9
OMIT -3 9 15
OMIT 3 9 0
OMIT 6 0 6
OMIT -3 6 9
OMIT 0 3 7
OMIT 6 9 6
OMIT 2 4 6
OMIT -3 3 3
OMIT 1 1 0
OMIT 6 3 3
OMIT -6 3 3
OMIT 0 0 6
OMIT -6 9 6
WGHT    0.031000    1.260500
BASF   0.00038
FVAR       0.11773
BR1   3    0.000999    0.864332    0.305161    11.00000    0.05767    0.04920 =
         0.06824    0.01825    0.01671    0.00963
BR2   3    0.266627    0.810756    0.157181    11.00000    0.05151    0.04231 =
         0.07633   -0.01799   -0.00056    0.01024
FE1   4    0.137265    0.944645    0.214293    11.00000    0.03347    0.02825 =
         0.04040   -0.00113   -0.00289    0.00320
O1    6   -0.006259    0.962243    0.142592    11.00000    0.05135    0.03706 =
         0.04503   -0.00885   -0.01024    0.01280
N1    5    0.043873    1.073676    0.249314    11.00000    0.03885    0.03275 =
         0.03623   -0.00462   -0.00183    0.00077
N2    5    0.372456    0.991100    0.248040    11.00000    0.03771    0.04078 =
         0.04562   -0.00043   -0.00259    0.00342
N3    5    0.632903    0.980183    0.282051    11.00000    0.03367    0.06514 =
         0.06480    0.00707   -0.00545   -0.00152
AFIX  43
H3    2    0.732948    0.958705    0.287875    11.00000   -1.20000
AFIX   0
C1    1   -0.131727    1.017077    0.125222    11.00000    0.03777    0.02941 =
         0.03565    0.00362    0.00038    0.00091
C2    1   -0.234653    0.994608    0.069046    11.00000    0.04646    0.03796 =
         0.03499   -0.00316   -0.00051    0.00278
C3    1   -0.365632    1.053865    0.054876    11.00000    0.04497    0.05126 =
         0.03481   -0.00043   -0.00694   -0.00111
AFIX  43
H3A   2   -0.434151    1.039197    0.018732    11.00000   -1.20000
AFIX   0
C4    1   -0.404134    1.134691    0.090603    11.00000    0.03823    0.04387 =
         0.03968    0.01013    0.00316    0.00591
C5    1   -0.302654    1.154789    0.144461    11.00000    0.04324    0.03339 =
         0.04222    0.00146    0.00460    0.00641
AFIX  43
H5    2   -0.323789    1.207641    0.169558    11.00000   -1.20000
AFIX   0
C6    1   -0.168066    1.096900    0.162065    11.00000    0.03466    0.03133 =
         0.03862    0.00228    0.00100   -0.00019
C7    1   -0.075452    1.120153    0.221622    11.00000    0.04090    0.02723 =
         0.04007   -0.00519    0.00182    0.00064
AFIX  43
H7    2   -0.105463    1.175208    0.242479    11.00000   -1.20000
AFIX   0
C8    1   -0.201074    0.907343    0.027692    11.00000    0.06271    0.05143 =
         0.03927   -0.01023   -0.00896    0.00685
C9    1   -0.024172    0.912150   -0.002797    11.00000    0.07768    0.08574 =
         0.05326   -0.02329    0.00227    0.01671
AFIX 137
H9A   2   -0.015711    0.965892   -0.030732    11.00000   -1.50000
H9B   2   -0.004038    0.857675   -0.029004    11.00000   -1.50000
H9C   2    0.058096    0.915895    0.032239    11.00000   -1.50000
AFIX   0
C10   1   -0.219558    0.821448    0.071191    11.00000    0.09354    0.04308 =
         0.07671   -0.01359   -0.01427   -0.00006
AFIX 137
H10A  2   -0.144802    0.825961    0.108727    11.00000   -1.50000
H10B  2   -0.191765    0.767500    0.045518    11.00000   -1.50000
H10C  2   -0.333749    0.816787    0.086723    11.00000   -1.50000
AFIX   0
C11   1   -0.329435    0.898208   -0.030080    11.00000    0.08575    0.08279 =
         0.05938   -0.03061   -0.02529    0.01560
AFIX 137
H11A  2   -0.440384    0.889178   -0.012068    11.00000   -1.50000
H11B  2   -0.299749    0.846226   -0.057474    11.00000   -1.50000
H11C  2   -0.327811    0.953554   -0.056541    11.00000   -1.50000
AFIX   0
C12   1   -0.559985    1.192005    0.072147    11.00000    0.04231    0.05837 =
         0.05272    0.01421    0.00403    0.01079
C13   1   -0.570760    1.205380   -0.002538    11.00000    0.05790    0.11084 =
         0.06600    0.03611    0.00639    0.02674
AFIX 137
H13A  2   -0.467940    1.232605   -0.018451    11.00000   -1.50000
H13B  2   -0.663697    1.245462   -0.012829    11.00000   -1.50000
H13C  2   -0.587489    1.146567   -0.023769    11.00000   -1.50000
AFIX   0
C14   1   -0.715392    1.138276    0.095305    11.00000    0.04480    0.11023 =
         0.09297    0.04319    0.01587    0.01147
AFIX 137
H14A  2   -0.709912    1.076111    0.078607    11.00000   -1.50000
H14B  2   -0.815269    1.167858    0.078661    11.00000   -1.50000
H14C  2   -0.718569    1.137123    0.143185    11.00000   -1.50000
AFIX   0
C15   1   -0.558891    1.284979    0.105132    11.00000    0.09082    0.07386 =
         0.13801   -0.01330   -0.03714    0.04789
AFIX 137
H15A  2   -0.564701    1.277271    0.152658    11.00000   -1.50000
H15B  2   -0.654329    1.320175    0.090181    11.00000   -1.50000
H15C  2   -0.456943    1.317078    0.093699    11.00000   -1.50000
AFIX   0
C16   1    0.113283    1.112395    0.311161    11.00000    0.05088    0.05333 =
         0.04329   -0.01623   -0.00749    0.00959
AFIX  23
H16A  2    0.111762    1.065639    0.345871    11.00000   -1.20000
H16B  2    0.044038    1.163858    0.325772    11.00000   -1.20000
AFIX   0
C17   1    0.291307    1.145001    0.300140    11.00000    0.06153    0.05165 =
         0.05272   -0.01550   -0.01040   -0.00314
AFIX  23
H17A  2    0.292642    1.187778    0.262855    11.00000   -1.20000
H17B  2    0.328589    1.178442    0.339423    11.00000   -1.20000
AFIX   0
C18   1    0.412711    1.068480    0.286357    11.00000    0.04445    0.04703 =
         0.04110   -0.00442   -0.00384   -0.00585
C19   1    0.572508    1.060189    0.307532    11.00000    0.04317    0.06872 =
         0.05407   -0.00644   -0.00399   -0.00945
AFIX  43
H19   2    0.630651    1.101594    0.334585    11.00000   -1.20000
AFIX   0
C20   1    0.512284    0.940585    0.246700    11.00000    0.03863    0.04846 =
         0.06346    0.00122   -0.00377    0.00091
AFIX  43
H20   2    0.523724    0.884870    0.223951    11.00000   -1.20000
HKLF 4
END  
;

# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
_database_code_depnum_ccdc_archive 'CCDC 998102'
#######################################################################
#
#                 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_darkwa140
_audit_creation_date             2014-01-15
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H28 Br2 Fe N3 O'
_chemical_formula_sum            'C20 H28 Br2 Fe N3 O'
_chemical_formula_weight         542.12
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.931(2)
_cell_length_b                   14.457(4)
_cell_length_c                   20.040(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2297.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    4.148
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            48840
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         1.737
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4413
_reflns_number_total             4685
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.000(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.050
_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)+(0.0310P)²+1.2590P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0630
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H16A,H16B} of C16, {H17A,H17B} of C17, H3 of N3, H20 of C20, H19 of C19,
  H3A of C3, H5 of C5, H7 of C7
 At 1.5 times of:
  {H15A,H15B,H15C} of C15, {H14A,H14B,H14C} of C14, {H13A,H13B,H13C} of C13,
  {H9A,H9B,H9C} of C9, {H10A,H10B,H10C} of C10, {H11A,H11B,H11C} of C11
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C7(H7), C19(H19), C20(H20), N3(H3)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.00100(7) 0.86433(3) 0.30516(2) 0.05837(14) Uani 1 1 d . . . . .
Br2 Br 0.26663(6) 0.81076(3) 0.15718(3) 0.05672(14) Uani 1 1 d . . . . .
C1 C -0.1317(5) 1.0171(2) 0.12522(18) 0.0343(7) Uani 1 1 d . . . . .
C2 C -0.2347(6) 0.9946(3) 0.06905(19) 0.0398(8) Uani 1 1 d . . . . .
C3 C -0.3656(5) 1.0539(3) 0.05488(19) 0.0437(9) Uani 1 1 d . . . . .
H3A H -0.4342 1.0392 0.0187 0.052 Uiso 1 1 calc R U . . .
C4 C -0.4041(5) 1.1347(3) 0.0906(2) 0.0406(9) Uani 1 1 d . . . . .
C5 C -0.3027(5) 1.1548(3) 0.1445(2) 0.0396(9) Uani 1 1 d . . . . .
H5 H -0.3238 1.2076 0.1696 0.048 Uiso 1 1 calc R U . . .
C6 C -0.1681(5) 1.0969(3) 0.16207(19) 0.0349(8) Uani 1 1 d . . . . .
C7 C -0.0755(5) 1.1202(2) 0.2216(2) 0.0361(8) Uani 1 1 d . . . . .
H7 H -0.1055 1.1752 0.2425 0.043 Uiso 1 1 calc R U . . .
C8 C -0.2011(6) 0.9073(3) 0.0277(2) 0.0511(11) Uani 1 1 d . . . . .
C9 C -0.0242(8) 0.9121(4) -0.0028(3) 0.0722(15) Uani 1 1 d . . . . .
H9A H -0.0157 0.9659 -0.0307 0.108 Uiso 1 1 calc R U . . .
H9B H -0.0040 0.8577 -0.0290 0.108 Uiso 1 1 calc R U . . .
H9C H 0.0581 0.9159 0.0322 0.108 Uiso 1 1 calc R U . . .
C10 C -0.2196(8) 0.8214(3) 0.0712(3) 0.0711(15) Uani 1 1 d . . . . .
H10A H -0.1448 0.8260 0.1087 0.107 Uiso 1 1 calc R U . . .
H10B H -0.1918 0.7675 0.0455 0.107 Uiso 1 1 calc R U . . .
H10C H -0.3337 0.8168 0.0867 0.107 Uiso 1 1 calc R U . . .
C11 C -0.3294(8) 0.8982(4) -0.0301(3) 0.0760(17) Uani 1 1 d . . . . .
H11A H -0.4404 0.8892 -0.0121 0.114 Uiso 1 1 calc R U . . .
H11B H -0.2997 0.8462 -0.0575 0.114 Uiso 1 1 calc R U . . .
H11C H -0.3278 0.9536 -0.0565 0.114 Uiso 1 1 calc R U . . .
C12 C -0.5600(5) 1.1920(4) 0.0721(2) 0.0511(11) Uani 1 1 d . . . . .
C13 C -0.5708(7) 1.2054(5) -0.0025(3) 0.0782(18) Uani 1 1 d . . . . .
H13A H -0.4679 1.2326 -0.0185 0.117 Uiso 1 1 calc R U . . .
H13B H -0.6637 1.2455 -0.0128 0.117 Uiso 1 1 calc R U . . .
H13C H -0.5875 1.1466 -0.0238 0.117 Uiso 1 1 calc R U . . .
C14 C -0.7154(7) 1.1383(5) 0.0953(3) 0.0827(19) Uani 1 1 d . . . . .
H14A H -0.7099 1.0761 0.0786 0.124 Uiso 1 1 calc R U . . .
H14B H -0.8153 1.1679 0.0787 0.124 Uiso 1 1 calc R U . . .
H14C H -0.7186 1.1371 0.1432 0.124 Uiso 1 1 calc R U . . .
C15 C -0.5589(9) 1.2850(4) 0.1051(4) 0.101(3) Uani 1 1 d . . . . .
H15A H -0.5647 1.2773 0.1527 0.151 Uiso 1 1 calc R U . . .
H15B H -0.6543 1.3202 0.0902 0.151 Uiso 1 1 calc R U . . .
H15C H -0.4569 1.3171 0.0937 0.151 Uiso 1 1 calc R U . . .
C16 C 0.1133(6) 1.1124(3) 0.3112(2) 0.0492(10) Uani 1 1 d . . . . .
H16A H 0.1118 1.0656 0.3459 0.059 Uiso 1 1 calc R U . . .
H16B H 0.0440 1.1639 0.3258 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2913(6) 1.1450(3) 0.3001(2) 0.0553(11) Uani 1 1 d . . . . .
H17A H 0.2926 1.1878 0.2629 0.066 Uiso 1 1 calc R U . . .
H17B H 0.3286 1.1784 0.3394 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4127(5) 1.0685(3) 0.2864(2) 0.0442(9) Uani 1 1 d . . . . .
C19 C 0.5725(6) 1.0602(4) 0.3075(2) 0.0553(11) Uani 1 1 d . . . . .
H19 H 0.6307 1.1016 0.3346 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5123(6) 0.9406(3) 0.2467(2) 0.0502(9) Uani 1 1 d . . . . .
H20 H 0.5237 0.8849 0.2240 0.060 Uiso 1 1 calc R U . . .
Fe1 Fe 0.13726(7) 0.94464(3) 0.21429(3) 0.03404(12) Uani 1 1 d . . . . .
N1 N 0.0439(4) 1.0737(2) 0.24931(16) 0.0359(7) Uani 1 1 d . . . . .
N2 N 0.3725(4) 0.9911(2) 0.24804(17) 0.0414(7) Uani 1 1 d . . . . .
N3 N 0.6329(5) 0.9802(3) 0.2821(2) 0.0545(9) Uani 1 1 d . . . . .
H3 H 0.7329 0.9587 0.2879 0.065 Uiso 1 1 calc R U . . .
O1 O -0.0063(4) 0.96224(18) 0.14259(13) 0.0445(6) 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
Br1 Fe1 2.4150(9) . ?
Br2 Fe1 2.4717(8) . ?
C1 C2 1.428(5) . ?
C1 C6 1.400(5) . ?
C1 O1 1.319(5) . ?
C2 C3 1.376(6) . ?
C2 C8 1.533(6) . ?
C3 H3A 0.9300 . ?
C3 C4 1.404(6) . ?
C4 C5 1.377(6) . ?
C4 C12 1.533(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(5) . ?
C6 C7 1.441(5) . ?
C7 H7 0.9300 . ?
C7 N1 1.286(5) . ?
C8 C9 1.532(8) . ?
C8 C10 1.524(7) . ?
C8 C11 1.547(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.512(7) . ?
C12 C14 1.529(7) . ?
C12 C15 1.498(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.505(7) . ?
C16 N1 1.467(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.492(6) . ?
C18 C19 1.342(6) . ?
C18 N2 1.394(5) . ?
C19 H19 0.9300 . ?
C19 N3 1.352(7) . ?
C20 H20 0.9300 . ?
C20 N2 1.328(6) . ?
C20 N3 1.321(6) . ?
Fe1 N1 2.126(3) . ?
Fe1 N2 2.095(4) . ?
Fe1 O1 1.851(3) . ?
N3 H3 0.8600 . ?

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
C6 C1 C2 119.1(3) . . ?
O1 C1 C2 120.2(3) . . ?
O1 C1 C6 120.8(3) . . ?
C1 C2 C8 120.9(4) . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 C8 122.1(4) . . ?
C2 C3 H3A 117.4 . . ?
C2 C3 C4 125.2(4) . . ?
C4 C3 H3A 117.4 . . ?
C3 C4 C12 120.1(4) . . ?
C5 C4 C3 116.6(4) . . ?
C5 C4 C12 123.1(4) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 C7 121.6(3) . . ?
C5 C6 C7 117.2(3) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.6(3) . . ?
N1 C7 H7 116.2 . . ?
C2 C8 C11 111.1(4) . . ?
C9 C8 C2 109.7(4) . . ?
C9 C8 C11 107.9(4) . . ?
C10 C8 C2 110.2(4) . . ?
C10 C8 C9 110.7(5) . . ?
C10 C8 C11 107.2(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C4 110.7(4) . . ?
C13 C12 C14 108.7(5) . . ?
C14 C12 C4 107.6(4) . . ?
C15 C12 C4 112.0(4) . . ?
C15 C12 C13 108.8(5) . . ?
C15 C12 C14 109.1(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
N1 C16 C17 110.3(4) . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.6(4) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C19 C18 C17 128.1(4) . . ?
C19 C18 N2 108.6(4) . . ?
N2 C18 C17 123.3(4) . . ?
C18 C19 H19 126.5 . . ?
C18 C19 N3 107.0(4) . . ?
N3 C19 H19 126.5 . . ?
N2 C20 H20 124.6 . . ?
N3 C20 H20 124.6 . . ?
N3 C20 N2 110.8(4) . . ?
Br1 Fe1 Br2 99.11(3) . . ?
N1 Fe1 Br1 90.98(9) . . ?
N1 Fe1 Br2 169.90(9) . . ?
N2 Fe1 Br1 108.01(10) . . ?
N2 Fe1 Br2 91.78(9) . . ?
N2 Fe1 N1 85.54(12) . . ?
O1 Fe1 Br1 112.10(11) . . ?
O1 Fe1 Br2 90.20(8) . . ?
O1 Fe1 N1 85.49(12) . . ?
O1 Fe1 N2 138.96(14) . . ?
C7 N1 C16 116.2(3) . . ?
C7 N1 Fe1 124.9(3) . . ?
C16 N1 Fe1 118.9(3) . . ?
C18 N2 Fe1 129.7(3) . . ?
C20 N2 C18 105.1(4) . . ?
C20 N2 Fe1 124.1(3) . . ?
C19 N3 H3 125.8 . . ?
C20 N3 C19 108.5(4) . . ?
C20 N3 H3 125.8 . . ?
C1 O1 Fe1 138.7(2) . . ?

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
C7 H7 Br1 0.93 3.01 3.619(4) 124.3 3
C7 H7 Br2 0.93 3.09 3.974(4) 160.5 3
C19 H19 Br2 0.93 3.14 3.905(5) 141.3 3_655
C20 H20 Br2 0.93 2.66 3.246(5) 121.3 .
N3 H3 Br1 0.86 2.55 3.397(4) 168.8 1_655

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
Br1 Fe1 O1 C1 77.5(4) . . . . ?
Br2 Fe1 O1 C1 177.4(4) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C8 C9 -60.9(5) . . . . ?
C1 C2 C8 C10 61.2(6) . . . . ?
C1 C2 C8 C11 179.8(4) . . . . ?
C1 C6 C7 N1 -1.7(6) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 C7 176.1(4) . . . . ?
C2 C1 O1 Fe1 -166.5(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C2 C3 C4 C12 -176.5(4) . . . . ?
C3 C2 C8 C9 120.2(5) . . . . ?
C3 C2 C8 C10 -117.7(5) . . . . ?
C3 C2 C8 C11 0.9(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C12 C13 -45.8(6) . . . . ?
C3 C4 C12 C14 72.8(6) . . . . ?
C3 C4 C12 C15 -167.4(5) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C4 C5 C6 C7 -176.1(4) . . . . ?
C5 C4 C12 C13 138.7(5) . . . . ?
C5 C4 C12 C14 -102.7(5) . . . . ?
C5 C4 C12 C15 17.1(7) . . . . ?
C5 C6 C7 N1 174.8(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C2 C8 -179.3(4) . . . . ?
C6 C1 O1 Fe1 12.2(6) . . . . ?
C6 C7 N1 C16 -178.3(4) . . . . ?
C6 C7 N1 Fe1 -1.0(6) . . . . ?
C8 C2 C3 C4 179.8(4) . . . . ?
C12 C4 C5 C6 175.7(4) . . . . ?
C16 C17 C18 C19 -141.6(5) . . . . ?
C16 C17 C18 N2 37.8(6) . . . . ?
C17 C16 N1 C7 -111.6(4) . . . . ?
C17 C16 N1 Fe1 70.9(4) . . . . ?
C17 C18 C19 N3 -179.4(4) . . . . ?
C17 C18 N2 C20 179.1(4) . . . . ?
C17 C18 N2 Fe1 -12.3(6) . . . . ?
C18 C19 N3 C20 -0.5(5) . . . . ?
C19 C18 N2 C20 -1.4(5) . . . . ?
C19 C18 N2 Fe1 167.2(3) . . . . ?
N1 C16 C17 C18 -67.0(5) . . . . ?
N1 Fe1 O1 C1 -11.7(4) . . . . ?
N2 C18 C19 N3 1.2(5) . . . . ?
N2 C20 N3 C19 -0.5(5) . . . . ?
N2 Fe1 O1 C1 -89.7(4) . . . . ?
N3 C20 N2 C18 1.1(5) . . . . ?
N3 C20 N2 Fe1 -168.2(3) . . . . ?
O1 C1 C2 C3 178.5(4) . . . . ?
O1 C1 C2 C8 -0.5(6) . . . . ?
O1 C1 C6 C5 -179.1(4) . . . . ?
O1 C1 C6 C7 -2.7(6) . . . . ?

_shelx_estimated_absorpt_T_max   0.575
_shelx_estimated_absorpt_T_min   0.436
_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.
;
_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 998103'
