# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_sarb02
_database_code_depnum_ccdc_archive 'CCDC 965895'
_audit_update_record             
;
2013-10-10 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 B F4 Fe N3'
_chemical_formula_weight         515.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5466(6)
_cell_length_b                   9.9789(6)
_cell_length_c                   14.7438(10)
_cell_angle_alpha                104.047(3)
_cell_angle_beta                 91.109(4)
_cell_angle_gamma                101.147(3)
_cell_volume                     1193.91(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5300
_cell_measurement_theta_min      1.43
_cell_measurement_theta_max      28.69

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 Kappa Apex II duo'
_diffrn_measurement_method       'omega phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40810
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         28.69
_reflns_number_total             6005
_reflns_number_gt                5300
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Kappa Apex II suite, 2008'
_computing_cell_refinement       'Bruker Kappa Apex II suite, 2008'
_computing_data_reduction        'Bruker Kappa Apex II suite, 2008'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0705P)²+1.4797P] 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         6005
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.70504(3) 0.80845(3) 0.935566(19) 0.01336(10) Uani 1 1 d . . .
F3 F -0.00288(18) 0.57258(19) 0.76487(12) 0.0389(4) Uani 1 1 d . . .
F1 F 0.1886(2) 0.5247(2) 0.85406(15) 0.0520(5) Uani 1 1 d . . .
F2 F 0.2605(2) 0.6151(2) 0.73096(12) 0.0443(4) Uani 1 1 d . . .
F4 F 0.1794(2) 0.7496(2) 0.85958(18) 0.0633(7) Uani 1 1 d . . .
N3 N 0.7099(2) 0.37064(18) 0.83261(12) 0.0143(3) Uani 1 1 d . . .
N2 N 0.6596(2) 0.27453(19) 0.75284(12) 0.0168(3) Uani 1 1 d . . .
N1 N 0.5496(2) 0.32704(18) 0.71564(12) 0.0151(3) Uani 1 1 d . . .
C13 C 0.4814(3) 0.2561(2) 0.62137(14) 0.0174(4) Uani 1 1 d . . .
C18 C 0.3295(3) 0.1689(2) 0.61008(15) 0.0188(4) Uani 1 1 d . . .
C2 C 0.6354(2) 0.4824(2) 0.84655(13) 0.0130(4) Uani 1 1 d . . .
C5 C 0.7838(3) 0.7726(2) 1.05843(14) 0.0173(4) Uani 1 1 d . . .
H5 H 0.8601 0.8330 1.1034 0.021 Uiso 1 1 calc R . .
C22 C 0.2365(3) 0.1433(2) 0.69327(15) 0.0203(4) Uani 1 1 d . . .
H22 H 0.2825 0.2195 0.7481 0.024 Uiso 1 1 calc R . .
C17 C 0.2726(3) 0.1006(2) 0.51794(16) 0.0234(4) Uani 1 1 d . . .
H17 H 0.1725 0.0408 0.5065 0.028 Uiso 1 1 calc R . .
C19 C 0.7350(3) 0.3834(2) 0.56609(16) 0.0235(5) Uani 1 1 d . . .
H19 H 0.7716 0.3970 0.6317 0.028 Uiso 1 1 calc R . .
C3 C 0.6645(2) 0.5991(2) 0.92991(13) 0.0136(4) Uani 1 1 d . . .
C1 C 0.5296(2) 0.4523(2) 0.76931(14) 0.0161(4) Uani 1 1 d . . .
H1 H 0.4591 0.5068 0.7567 0.019 Uiso 1 1 calc R . .
C25 C 0.8355(2) 0.3461(2) 0.89209(15) 0.0178(4) Uani 1 1 d . . .
H25C H 0.8323 0.2466 0.8802 0.027 Uiso 1 1 calc R . .
H25A H 0.8184 0.3828 0.9568 0.027 Uiso 1 1 calc R . .
H25B H 0.9380 0.3929 0.8783 0.027 Uiso 1 1 calc R . .
C7 C 0.5414(2) 0.6618(2) 0.97733(14) 0.0159(4) Uani 1 1 d . . .
H7 H 0.4327 0.6371 0.9594 0.019 Uiso 1 1 calc R . .
C14 C 0.5752(3) 0.2806(2) 0.54815(15) 0.0194(4) Uani 1 1 d . . .
C15 C 0.5106(3) 0.2094(3) 0.45748(16) 0.0246(5) Uani 1 1 d . . .
H15 H 0.5682 0.2222 0.4063 0.030 Uiso 1 1 calc R . .
C16 C 0.3617(3) 0.1199(3) 0.44309(16) 0.0263(5) Uani 1 1 d . . .
H16 H 0.3212 0.0723 0.3824 0.032 Uiso 1 1 calc R . .
C11 C 0.8291(3) 1.0023(2) 0.92870(18) 0.0264(5) Uani 1 1 d . . .
H11 H 0.9069 1.0626 0.9727 0.032 Uiso 1 1 calc R . .
C21 C 0.8627(3) 0.3288(3) 0.50565(19) 0.0286(5) Uani 1 1 d . . .
H21A H 0.9610 0.3977 0.5197 0.043 Uiso 1 1 calc R . .
H21B H 0.8288 0.3119 0.4407 0.043 Uiso 1 1 calc R . .
H21C H 0.8789 0.2424 0.5184 0.043 Uiso 1 1 calc R . .
C20 C 0.7145(3) 0.5266(3) 0.5533(2) 0.0345(6) Uani 1 1 d . . .
H20A H 0.8161 0.5910 0.5649 0.052 Uiso 1 1 calc R . .
H20B H 0.6414 0.5631 0.5967 0.052 Uiso 1 1 calc R . .
H20C H 0.6730 0.5158 0.4904 0.052 Uiso 1 1 calc R . .
C9 C 0.5867(3) 0.8962(3) 0.8508(2) 0.0379(7) Uani 1 1 d . . .
H9 H 0.4775 0.8734 0.8341 0.046 Uiso 1 1 calc R . .
C23 C 0.2599(4) 0.0048(3) 0.71280(19) 0.0391(7) Uani 1 1 d . . .
H23A H 0.2013 -0.0113 0.7654 0.059 Uiso 1 1 calc R . .
H23B H 0.3714 0.0100 0.7266 0.059 Uiso 1 1 calc R . .
H23C H 0.2216 -0.0714 0.6587 0.059 Uiso 1 1 calc R . .
C24 C 0.0606(3) 0.1470(5) 0.6801(2) 0.0521(10) Uani 1 1 d . . .
H24A H 0.0071 0.1304 0.7342 0.078 Uiso 1 1 calc R . .
H24B H 0.0128 0.0752 0.6255 0.078 Uiso 1 1 calc R . .
H24C H 0.0507 0.2378 0.6722 0.078 Uiso 1 1 calc R . .
C8 C 0.7062(5) 0.8311(3) 0.80243(18) 0.0456(9) Uani 1 1 d . . .
H8 H 0.6888 0.7580 0.7481 0.055 Uiso 1 1 calc R . .
B1 B 0.1555(3) 0.6150(3) 0.8009(2) 0.0254(5) Uani 1 1 d . . .
C6 C 0.6162(3) 0.7686(2) 1.05682(14) 0.0167(4) Uani 1 1 d . . .
H6 H 0.5646 0.8260 1.1003 0.020 Uiso 1 1 calc R . .
C4 C 0.8152(2) 0.6690(2) 0.97984(14) 0.0156(4) Uani 1 1 d . . .
H4 H 0.9149 0.6501 0.9638 0.019 Uiso 1 1 calc R . .
C10 C 0.6653(3) 1.0014(3) 0.92845(19) 0.0282(5) Uani 1 1 d . . .
H10 H 0.6164 1.0607 0.9724 0.034 Uiso 1 1 calc R . .
C12 C 0.8572(3) 0.8977(3) 0.8520(2) 0.0350(6) Uani 1 1 d . . .
H12 H 0.9558 0.8758 0.8363 0.042 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 2.030(2) . ?
Fe1 C3 2.0313(19) . ?
Fe1 C12 2.037(2) . ?
Fe1 C7 2.039(2) . ?
Fe1 C4 2.043(2) . ?
Fe1 C9 2.044(2) . ?
Fe1 C11 2.045(2) . ?
Fe1 C10 2.046(2) . ?
Fe1 C6 2.052(2) . ?
Fe1 C5 2.055(2) . ?
F3 B1 1.391(3) . ?
F1 B1 1.392(3) . ?
F2 B1 1.381(3) . ?
F4 B1 1.384(3) . ?
N3 N2 1.327(2) . ?
N3 C2 1.363(3) . ?
N3 C25 1.466(3) . ?
N2 N1 1.330(2) . ?
N1 C1 1.351(3) . ?
N1 C13 1.451(3) . ?
C13 C18 1.398(3) . ?
C13 C14 1.398(3) . ?
C18 C17 1.394(3) . ?
C18 C22 1.521(3) . ?
C2 C1 1.376(3) . ?
C2 C3 1.453(3) . ?
C5 C4 1.422(3) . ?
C5 C6 1.425(3) . ?
C22 C24 1.521(4) . ?
C22 C23 1.527(4) . ?
C17 C16 1.384(3) . ?
C19 C14 1.517(3) . ?
C19 C21 1.521(3) . ?
C19 C20 1.528(4) . ?
C3 C4 1.433(3) . ?
C3 C7 1.434(3) . ?
C7 C6 1.421(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.385(3) . ?
C11 C10 1.399(4) . ?
C11 C12 1.400(4) . ?
C9 C10 1.407(4) . ?
C9 C8 1.426(5) . ?
C8 C12 1.428(5) . ?

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
C8 Fe1 C3 108.32(10) . . ?
C8 Fe1 C12 41.12(14) . . ?
C3 Fe1 C12 122.72(10) . . ?
C8 Fe1 C7 123.32(11) . . ?
C3 Fe1 C7 41.27(8) . . ?
C12 Fe1 C7 159.58(11) . . ?
C8 Fe1 C4 123.49(12) . . ?
C3 Fe1 C4 41.19(8) . . ?
C12 Fe1 C4 106.50(10) . . ?
C7 Fe1 C4 69.50(8) . . ?
C8 Fe1 C9 40.97(14) . . ?
C3 Fe1 C9 124.47(10) . . ?
C12 Fe1 C9 68.93(12) . . ?
C7 Fe1 C9 107.93(10) . . ?
C4 Fe1 C9 160.82(12) . . ?
C8 Fe1 C11 67.88(11) . . ?
C3 Fe1 C11 158.05(9) . . ?
C12 Fe1 C11 40.10(11) . . ?
C7 Fe1 C11 159.06(10) . . ?
C4 Fe1 C11 121.42(9) . . ?
C9 Fe1 C11 67.83(10) . . ?
C8 Fe1 C10 67.95(11) . . ?
C3 Fe1 C10 160.65(10) . . ?
C12 Fe1 C10 67.87(10) . . ?
C7 Fe1 C10 123.59(9) . . ?
C4 Fe1 C10 156.93(10) . . ?
C9 Fe1 C10 40.25(12) . . ?
C11 Fe1 C10 39.99(10) . . ?
C8 Fe1 C6 159.02(13) . . ?
C3 Fe1 C6 68.60(8) . . ?
C12 Fe1 C6 158.21(12) . . ?
C7 Fe1 C6 40.64(8) . . ?
C4 Fe1 C6 68.78(8) . . ?
C9 Fe1 C6 122.41(11) . . ?
C11 Fe1 C6 122.87(10) . . ?
C10 Fe1 C6 107.68(9) . . ?
C8 Fe1 C5 159.36(13) . . ?
C3 Fe1 C5 68.43(8) . . ?
C12 Fe1 C5 122.15(11) . . ?
C7 Fe1 C5 68.60(8) . . ?
C4 Fe1 C5 40.61(8) . . ?
C9 Fe1 C5 157.64(12) . . ?
C11 Fe1 C5 107.08(9) . . ?
C10 Fe1 C5 121.94(10) . . ?
C6 Fe1 C5 40.60(8) . . ?
N2 N3 C2 113.07(16) . . ?
N2 N3 C25 118.01(17) . . ?
C2 N3 C25 128.92(17) . . ?
N3 N2 N1 103.50(16) . . ?
N2 N1 C1 113.06(17) . . ?
N2 N1 C13 118.49(17) . . ?
C1 N1 C13 127.99(18) . . ?
C18 C13 C14 124.99(19) . . ?
C18 C13 N1 118.55(18) . . ?
C14 C13 N1 116.46(18) . . ?
C17 C18 C13 115.8(2) . . ?
C17 C18 C22 122.1(2) . . ?
C13 C18 C22 122.08(18) . . ?
N3 C2 C1 104.75(17) . . ?
N3 C2 C3 123.96(18) . . ?
C1 C2 C3 131.21(19) . . ?
C4 C5 C6 108.67(18) . . ?
C4 C5 Fe1 69.24(11) . . ?
C6 C5 Fe1 69.60(11) . . ?
C18 C22 C24 112.6(2) . . ?
C18 C22 C23 109.47(19) . . ?
C24 C22 C23 112.0(3) . . ?
C16 C17 C18 121.5(2) . . ?
C14 C19 C21 112.89(19) . . ?
C14 C19 C20 110.1(2) . . ?
C21 C19 C20 111.1(2) . . ?
C4 C3 C7 108.45(17) . . ?
C4 C3 C2 127.34(18) . . ?
C7 C3 C2 124.20(18) . . ?
C4 C3 Fe1 69.84(11) . . ?
C7 C3 Fe1 69.64(11) . . ?
C2 C3 Fe1 127.30(14) . . ?
N1 C1 C2 105.62(18) . . ?
C6 C7 C3 107.41(18) . . ?
C6 C7 Fe1 70.20(11) . . ?
C3 C7 Fe1 69.09(11) . . ?
C13 C14 C15 116.3(2) . . ?
C13 C14 C19 121.72(19) . . ?
C15 C14 C19 122.0(2) . . ?
C16 C15 C14 120.7(2) . . ?
C17 C16 C15 120.8(2) . . ?
C10 C11 C12 109.1(2) . . ?
C10 C11 Fe1 70.02(13) . . ?
C12 C11 Fe1 69.64(14) . . ?
C10 C9 C8 107.0(2) . . ?
C10 C9 Fe1 69.93(14) . . ?
C8 C9 Fe1 68.97(15) . . ?
C9 C8 C12 108.0(2) . . ?
C9 C8 Fe1 70.05(15) . . ?
C12 C8 Fe1 69.71(15) . . ?
F2 B1 F4 108.8(2) . . ?
F2 B1 F3 111.9(2) . . ?
F4 B1 F3 109.7(2) . . ?
F2 B1 F1 109.2(2) . . ?
F4 B1 F1 107.7(2) . . ?
F3 B1 F1 109.4(2) . . ?
C7 C6 C5 108.30(18) . . ?
C7 C6 Fe1 69.16(11) . . ?
C5 C6 Fe1 69.79(11) . . ?
C5 C4 C3 107.16(18) . . ?
C5 C4 Fe1 70.15(12) . . ?
C3 C4 Fe1 68.96(11) . . ?
C11 C10 C9 108.8(2) . . ?
C11 C10 Fe1 69.99(13) . . ?
C9 C10 Fe1 69.81(14) . . ?
C11 C12 C8 107.1(2) . . ?
C11 C12 Fe1 70.26(14) . . ?
C8 C12 Fe1 69.16(15) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         1.472
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.085
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sarb05
_database_code_depnum_ccdc_archive 'CCDC 965899'
_audit_update_record             
;
2013-10-10 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Fe N3'
_chemical_formula_weight         413.34

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.0171(8)
_cell_length_b                   49.949(3)
_cell_length_c                   7.7045(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8088.0(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3692
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      28.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3488
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6852
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(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 Kappa APEXII duo'
_diffrn_measurement_method       'omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18835
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -66
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4457
_reflns_number_gt                3692
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEXII software suite, 2008'
_computing_cell_refinement       'Bruker APEXII software suite, 2008'
_computing_data_reduction        'Bruker APEXII software suite, 2008'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0229P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(13)
_refine_ls_number_reflns         4457
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.033474(16) 0.050973(7) 0.13549(4) 0.01183(8) Uani 1 1 d . . .
N5 N 0.00701(8) 0.14987(4) 0.1589(3) 0.0105(4) Uani 1 1 d . . .
C5 C -0.01676(11) 0.08038(5) 0.2611(3) 0.0105(5) Uani 1 1 d . . .
C9 C 0.02694(10) 0.06775(5) 0.3775(3) 0.0132(5) Uani 1 1 d . . .
H9 H 0.0602 0.0764 0.4394 0.016 Uiso 1 1 calc R . .
N3 N -0.05178(9) 0.14532(4) 0.0918(2) 0.0155(5) Uani 1 1 d . . .
N1 N -0.06610(9) 0.12035(4) 0.1263(3) 0.0142(4) Uani 1 1 d . . .
C8 C 0.01199(11) 0.04025(5) 0.3843(4) 0.0158(5) Uani 1 1 d . . .
H8 H 0.0337 0.0271 0.4513 0.019 Uiso 1 1 calc R . .
C7 C -0.04080(12) 0.03548(5) 0.2743(3) 0.0168(6) Uani 1 1 d . . .
H7 H -0.0608 0.0187 0.2552 0.020 Uiso 1 1 calc R . .
C6 C -0.05864(11) 0.06011(5) 0.1976(3) 0.0115(5) Uani 1 1 d . . .
H6 H -0.0925 0.0627 0.1177 0.014 Uiso 1 1 calc R . .
C11 C 0.06831(12) 0.06780(5) -0.0871(3) 0.0223(6) Uani 1 1 d . . .
H11 H 0.0572 0.0848 -0.1327 0.027 Uiso 1 1 calc R . .
C12 C 0.11827(13) 0.06248(6) 0.0300(3) 0.0249(7) Uani 1 1 d . . .
H12 H 0.1467 0.0753 0.0775 0.030 Uiso 1 1 calc R . .
C13 C 0.11868(13) 0.03454(6) 0.0645(3) 0.0217(7) Uani 1 1 d . . .
H13 H 0.1475 0.0255 0.1391 0.026 Uiso 1 1 calc R . .
C14 C 0.06885(12) 0.02259(5) -0.0309(3) 0.0174(6) Uani 1 1 d . . .
H14 H 0.0582 0.0041 -0.0319 0.021 Uiso 1 1 calc R . .
C10 C 0.03754(11) 0.04316(6) -0.1250(4) 0.0199(6) Uani 1 1 d . . .
H10 H 0.0022 0.0408 -0.2002 0.024 Uiso 1 1 calc R . .
C3 C -0.01613(11) 0.10865(5) 0.2124(3) 0.0106(5) Uani 1 1 d . . .
C1 C 0.03047(11) 0.12742(5) 0.2332(3) 0.0105(5) Uani 1 1 d . . .
H1 H 0.0706 0.1252 0.2880 0.013 Uiso 1 1 calc R . .
C15 C 0.04183(10) 0.17345(5) 0.1074(3) 0.0115(5) Uani 1 1 d . . .
C16 C 0.03404(11) 0.19724(5) 0.1995(3) 0.0120(5) Uani 1 1 d . . .
C17 C 0.06756(11) 0.21960(5) 0.1403(4) 0.0162(5) Uani 1 1 d . . .
H17 H 0.0633 0.2362 0.1989 0.019 Uiso 1 1 calc R . .
C18 C 0.10711(12) 0.21770(5) -0.0036(3) 0.0172(6) Uani 1 1 d . . .
H18 H 0.1294 0.2331 -0.0429 0.021 Uiso 1 1 calc R . .
C19 C 0.11444(11) 0.19379(5) -0.0901(3) 0.0174(6) Uani 1 1 d . . .
H19 H 0.1423 0.1928 -0.1869 0.021 Uiso 1 1 calc R . .
C20 C 0.08156(11) 0.17097(5) -0.0374(3) 0.0135(6) Uani 1 1 d . . .
C21 C -0.01084(11) 0.19949(5) 0.3538(3) 0.0158(6) Uani 1 1 d . . .
H21 H -0.0191 0.1810 0.3982 0.019 Uiso 1 1 calc R . .
C23 C 0.01682(12) 0.21586(6) 0.5023(3) 0.0223(6) Uani 1 1 d . . .
H23C H 0.0596 0.2093 0.5300 0.033 Uiso 1 1 calc R . .
H23A H -0.0105 0.2141 0.6047 0.033 Uiso 1 1 calc R . .
H23B H 0.0193 0.2347 0.4679 0.033 Uiso 1 1 calc R . .
C22 C -0.07480(12) 0.21141(6) 0.2951(3) 0.0239(7) Uani 1 1 d . . .
H22B H -0.0685 0.2301 0.2594 0.036 Uiso 1 1 calc R . .
H22A H -0.1052 0.2107 0.3914 0.036 Uiso 1 1 calc R . .
H22C H -0.0914 0.2011 0.1969 0.036 Uiso 1 1 calc R . .
C24 C 0.08822(11) 0.14485(5) -0.1366(3) 0.0170(6) Uani 1 1 d . . .
H24 H 0.0595 0.1315 -0.0801 0.020 Uiso 1 1 calc R . .
C26 C 0.15639(11) 0.13408(5) -0.1234(4) 0.0219(6) Uani 1 1 d . . .
H26B H 0.1861 0.1473 -0.1715 0.033 Uiso 1 1 calc R . .
H26C H 0.1598 0.1173 -0.1889 0.033 Uiso 1 1 calc R . .
H26A H 0.1669 0.1308 -0.0014 0.033 Uiso 1 1 calc R . .
C25 C 0.06696(12) 0.14772(5) -0.3244(3) 0.0227(6) Uani 1 1 d . . .
H25A H 0.0236 0.1549 -0.3279 0.034 Uiso 1 1 calc R . .
H25B H 0.0678 0.1302 -0.3810 0.034 Uiso 1 1 calc R . .
H25C H 0.0958 0.1599 -0.3854 0.034 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 2.041(3) . ?
Fe1 C12 2.041(3) . ?
Fe1 C13 2.044(3) . ?
Fe1 C7 2.044(2) . ?
Fe1 C11 2.046(3) . ?
Fe1 C6 2.046(2) . ?
Fe1 C10 2.046(3) . ?
Fe1 C9 2.049(3) . ?
Fe1 C14 2.051(2) . ?
Fe1 C5 2.052(2) . ?
N5 C1 1.352(3) . ?
N5 N3 1.359(2) . ?
N5 C15 1.442(3) . ?
C5 C6 1.428(3) . ?
C5 C9 1.430(3) . ?
C5 C3 1.461(3) . ?
C9 C8 1.410(3) . ?
C9 H9 0.9500 . ?
N3 N1 1.310(3) . ?
N1 C3 1.372(3) . ?
C8 C7 1.417(3) . ?
C8 H8 0.9500 . ?
C7 C6 1.415(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C11 C12 1.410(4) . ?
C11 C10 1.421(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.421(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.412(4) . ?
C13 H13 0.9500 . ?
C14 C10 1.419(4) . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C3 C1 1.365(3) . ?
C1 H1 0.9500 . ?
C15 C16 1.393(3) . ?
C15 C20 1.399(3) . ?
C16 C17 1.397(3) . ?
C16 C21 1.522(3) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(3) . ?
C19 H19 0.9500 . ?
C20 C24 1.518(3) . ?
C21 C23 1.522(3) . ?
C21 C22 1.538(3) . ?
C21 H21 1.0000 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22C 0.9800 . ?
C24 C25 1.521(3) . ?
C24 C26 1.534(3) . ?
C24 H24 1.0000 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 H26A 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C8 Fe1 C12 129.87(11) . . ?
C8 Fe1 C13 109.85(10) . . ?
C12 Fe1 C13 40.69(11) . . ?
C8 Fe1 C7 40.58(9) . . ?
C12 Fe1 C7 168.97(12) . . ?
C13 Fe1 C7 131.05(11) . . ?
C8 Fe1 C11 167.05(11) . . ?
C12 Fe1 C11 40.35(11) . . ?
C13 Fe1 C11 68.11(11) . . ?
C7 Fe1 C11 150.16(10) . . ?
C8 Fe1 C6 68.26(9) . . ?
C12 Fe1 C6 148.92(11) . . ?
C13 Fe1 C6 168.83(11) . . ?
C7 Fe1 C6 40.50(10) . . ?
C11 Fe1 C6 116.30(10) . . ?
C8 Fe1 C10 151.68(10) . . ?
C12 Fe1 C10 68.07(10) . . ?
C13 Fe1 C10 67.95(10) . . ?
C7 Fe1 C10 118.20(10) . . ?
C11 Fe1 C10 40.63(10) . . ?
C6 Fe1 C10 108.14(10) . . ?
C8 Fe1 C9 40.34(10) . . ?
C12 Fe1 C9 107.81(10) . . ?
C13 Fe1 C9 117.79(10) . . ?
C7 Fe1 C9 68.15(10) . . ?
C11 Fe1 C9 128.24(10) . . ?
C6 Fe1 C9 68.44(9) . . ?
C10 Fe1 C9 166.74(10) . . ?
C8 Fe1 C14 119.06(10) . . ?
C12 Fe1 C14 68.23(11) . . ?
C13 Fe1 C14 40.34(10) . . ?
C7 Fe1 C14 110.00(11) . . ?
C11 Fe1 C14 68.30(11) . . ?
C6 Fe1 C14 130.05(10) . . ?
C10 Fe1 C14 40.53(10) . . ?
C9 Fe1 C14 151.15(10) . . ?
C8 Fe1 C5 68.34(10) . . ?
C12 Fe1 C5 115.83(11) . . ?
C13 Fe1 C5 149.81(10) . . ?
C7 Fe1 C5 68.37(10) . . ?
C11 Fe1 C5 106.60(10) . . ?
C6 Fe1 C5 40.80(9) . . ?
C10 Fe1 C5 128.38(10) . . ?
C9 Fe1 C5 40.82(9) . . ?
C14 Fe1 C5 167.53(9) . . ?
C1 N5 N3 110.75(19) . . ?
C1 N5 C15 127.50(19) . . ?
N3 N5 C15 119.55(19) . . ?
C6 C5 C9 107.3(2) . . ?
C6 C5 C3 127.0(2) . . ?
C9 C5 C3 125.6(2) . . ?
C6 C5 Fe1 69.37(13) . . ?
C9 C5 Fe1 69.49(14) . . ?
C3 C5 Fe1 124.46(16) . . ?
C8 C9 C5 108.0(2) . . ?
C8 C9 Fe1 69.52(15) . . ?
C5 C9 Fe1 69.69(14) . . ?
C8 C9 H9 126.0 . . ?
C5 C9 H9 126.0 . . ?
Fe1 C9 H9 126.4 . . ?
N1 N3 N5 106.91(18) . . ?
N3 N1 C3 109.11(18) . . ?
C9 C8 C7 108.4(2) . . ?
C9 C8 Fe1 70.14(15) . . ?
C7 C8 Fe1 69.84(15) . . ?
C9 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
Fe1 C8 H8 125.8 . . ?
C6 C7 C8 108.1(2) . . ?
C6 C7 Fe1 69.81(14) . . ?
C8 C7 Fe1 69.58(15) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
Fe1 C7 H7 126.2 . . ?
C7 C6 C5 108.1(2) . . ?
C7 C6 Fe1 69.70(14) . . ?
C5 C6 Fe1 69.83(13) . . ?
C7 C6 H6 126.0 . . ?
C5 C6 H6 126.0 . . ?
Fe1 C6 H6 126.1 . . ?
C12 C11 C10 107.9(3) . . ?
C12 C11 Fe1 69.66(15) . . ?
C10 C11 Fe1 69.70(16) . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
Fe1 C11 H11 126.1 . . ?
C11 C12 C13 108.1(2) . . ?
C11 C12 Fe1 69.99(15) . . ?
C13 C12 Fe1 69.76(15) . . ?
C11 C12 H12 126.0 . . ?
C13 C12 H12 126.0 . . ?
Fe1 C12 H12 125.9 . . ?
C14 C13 C12 108.2(2) . . ?
C14 C13 Fe1 70.08(14) . . ?
C12 C13 Fe1 69.54(15) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
Fe1 C13 H13 126.1 . . ?
C13 C14 C10 107.7(2) . . ?
C13 C14 Fe1 69.59(14) . . ?
C10 C14 Fe1 69.56(15) . . ?
C13 C14 H14 126.2 . . ?
C10 C14 H14 126.2 . . ?
Fe1 C14 H14 126.3 . . ?
C14 C10 C11 108.1(2) . . ?
C14 C10 Fe1 69.90(15) . . ?
C11 C10 Fe1 69.67(16) . . ?
C14 C10 H10 125.9 . . ?
C11 C10 H10 125.9 . . ?
Fe1 C10 H10 126.1 . . ?
C1 C3 N1 108.3(2) . . ?
C1 C3 C5 129.8(2) . . ?
N1 C3 C5 121.9(2) . . ?
N5 C1 C3 104.9(2) . . ?
N5 C1 H1 127.5 . . ?
C3 C1 H1 127.5 . . ?
C16 C15 C20 123.5(2) . . ?
C16 C15 N5 119.8(2) . . ?
C20 C15 N5 116.7(2) . . ?
C15 C16 C17 117.1(2) . . ?
C15 C16 C21 122.3(2) . . ?
C17 C16 C21 120.6(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 117.1(2) . . ?
C19 C20 C24 120.7(2) . . ?
C15 C20 C24 122.2(2) . . ?
C16 C21 C23 113.0(2) . . ?
C16 C21 C22 109.9(2) . . ?
C23 C21 C22 110.3(2) . . ?
C16 C21 H21 107.8 . . ?
C23 C21 H21 107.8 . . ?
C22 C21 H21 107.8 . . ?
C21 C23 H23C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
C20 C24 C25 111.8(2) . . ?
C20 C24 C26 110.7(2) . . ?
C25 C24 C26 111.7(2) . . ?
C20 C24 H24 107.5 . . ?
C25 C24 H24 107.5 . . ?
C26 C24 H24 107.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
H26B C26 H26A 109.5 . . ?
H26C C26 H26A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C8 Fe1 C5 C6 -81.39(15) . . . . ?
C12 Fe1 C5 C6 153.57(15) . . . . ?
C13 Fe1 C5 C6 -173.90(19) . . . . ?
C7 Fe1 C5 C6 -37.58(14) . . . . ?
C11 Fe1 C5 C6 111.24(15) . . . . ?
C10 Fe1 C5 C6 71.96(18) . . . . ?
C9 Fe1 C5 C6 -118.8(2) . . . . ?
C14 Fe1 C5 C6 47.3(5) . . . . ?
C8 Fe1 C5 C9 37.37(14) . . . . ?
C12 Fe1 C5 C9 -87.67(16) . . . . ?
C13 Fe1 C5 C9 -55.2(3) . . . . ?
C7 Fe1 C5 C9 81.18(15) . . . . ?
C11 Fe1 C5 C9 -130.01(14) . . . . ?
C6 Fe1 C5 C9 118.8(2) . . . . ?
C10 Fe1 C5 C9 -169.29(14) . . . . ?
C14 Fe1 C5 C9 166.0(4) . . . . ?
C8 Fe1 C5 C3 157.1(2) . . . . ?
C12 Fe1 C5 C3 32.1(2) . . . . ?
C13 Fe1 C5 C3 64.6(3) . . . . ?
C7 Fe1 C5 C3 -159.1(2) . . . . ?
C11 Fe1 C5 C3 -10.3(2) . . . . ?
C6 Fe1 C5 C3 -121.5(3) . . . . ?
C10 Fe1 C5 C3 -49.5(2) . . . . ?
C9 Fe1 C5 C3 119.8(3) . . . . ?
C14 Fe1 C5 C3 -74.2(5) . . . . ?
C6 C5 C9 C8 0.1(3) . . . . ?
C3 C5 C9 C8 -177.5(2) . . . . ?
Fe1 C5 C9 C8 -59.14(17) . . . . ?
C6 C5 C9 Fe1 59.28(15) . . . . ?
C3 C5 C9 Fe1 -118.4(2) . . . . ?
C12 Fe1 C9 C8 -131.45(15) . . . . ?
C13 Fe1 C9 C8 -88.41(16) . . . . ?
C7 Fe1 C9 C8 37.64(14) . . . . ?
C11 Fe1 C9 C8 -171.46(15) . . . . ?
C6 Fe1 C9 C8 81.37(14) . . . . ?
C10 Fe1 C9 C8 158.8(4) . . . . ?
C14 Fe1 C9 C8 -54.4(2) . . . . ?
C5 Fe1 C9 C8 119.39(19) . . . . ?
C8 Fe1 C9 C5 -119.39(19) . . . . ?
C12 Fe1 C9 C5 109.16(16) . . . . ?
C13 Fe1 C9 C5 152.19(15) . . . . ?
C7 Fe1 C9 C5 -81.76(15) . . . . ?
C11 Fe1 C9 C5 69.15(17) . . . . ?
C6 Fe1 C9 C5 -38.02(14) . . . . ?
C10 Fe1 C9 C5 39.5(4) . . . . ?
C14 Fe1 C9 C5 -173.80(19) . . . . ?
C1 N5 N3 N1 1.3(3) . . . . ?
C15 N5 N3 N1 165.62(19) . . . . ?
N5 N3 N1 C3 -1.2(3) . . . . ?
C5 C9 C8 C7 -0.3(3) . . . . ?
Fe1 C9 C8 C7 -59.56(18) . . . . ?
C5 C9 C8 Fe1 59.25(17) . . . . ?
C12 Fe1 C8 C9 68.41(18) . . . . ?
C13 Fe1 C8 C9 109.92(14) . . . . ?
C7 Fe1 C8 C9 -119.4(2) . . . . ?
C11 Fe1 C8 C9 31.4(5) . . . . ?
C6 Fe1 C8 C9 -81.86(14) . . . . ?
C10 Fe1 C8 C9 -169.96(18) . . . . ?
C14 Fe1 C8 C9 153.33(13) . . . . ?
C5 Fe1 C8 C9 -37.80(13) . . . . ?
C12 Fe1 C8 C7 -172.20(16) . . . . ?
C13 Fe1 C8 C7 -130.69(15) . . . . ?
C11 Fe1 C8 C7 150.8(4) . . . . ?
C6 Fe1 C8 C7 37.53(15) . . . . ?
C10 Fe1 C8 C7 -50.6(3) . . . . ?
C9 Fe1 C8 C7 119.4(2) . . . . ?
C14 Fe1 C8 C7 -87.28(17) . . . . ?
C5 Fe1 C8 C7 81.60(16) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
Fe1 C8 C7 C6 -59.37(16) . . . . ?
C9 C8 C7 Fe1 59.74(18) . . . . ?
C8 Fe1 C7 C6 119.4(2) . . . . ?
C12 Fe1 C7 C6 152.4(5) . . . . ?
C13 Fe1 C7 C6 -169.57(14) . . . . ?
C11 Fe1 C7 C6 -47.9(3) . . . . ?
C10 Fe1 C7 C6 -85.19(17) . . . . ?
C9 Fe1 C7 C6 81.96(15) . . . . ?
C14 Fe1 C7 C6 -128.92(15) . . . . ?
C5 Fe1 C7 C6 37.85(14) . . . . ?
C12 Fe1 C7 C8 33.0(6) . . . . ?
C13 Fe1 C7 C8 71.05(18) . . . . ?
C11 Fe1 C7 C8 -167.30(19) . . . . ?
C6 Fe1 C7 C8 -119.4(2) . . . . ?
C10 Fe1 C7 C8 155.43(13) . . . . ?
C9 Fe1 C7 C8 -37.43(14) . . . . ?
C14 Fe1 C7 C8 111.70(15) . . . . ?
C5 Fe1 C7 C8 -81.53(15) . . . . ?
C8 C7 C6 C5 -0.3(3) . . . . ?
Fe1 C7 C6 C5 -59.52(16) . . . . ?
C8 C7 C6 Fe1 59.23(17) . . . . ?
C9 C5 C6 C7 0.1(3) . . . . ?
C3 C5 C6 C7 177.7(2) . . . . ?
Fe1 C5 C6 C7 59.44(16) . . . . ?
C9 C5 C6 Fe1 -59.35(16) . . . . ?
C3 C5 C6 Fe1 118.3(2) . . . . ?
C8 Fe1 C6 C7 -37.60(14) . . . . ?
C12 Fe1 C6 C7 -170.1(2) . . . . ?
C13 Fe1 C6 C7 44.8(6) . . . . ?
C11 Fe1 C6 C7 155.67(15) . . . . ?
C10 Fe1 C6 C7 112.46(16) . . . . ?
C9 Fe1 C6 C7 -81.16(15) . . . . ?
C14 Fe1 C6 C7 72.76(18) . . . . ?
C5 Fe1 C6 C7 -119.2(2) . . . . ?
C8 Fe1 C6 C5 81.60(15) . . . . ?
C12 Fe1 C6 C5 -50.9(2) . . . . ?
C13 Fe1 C6 C5 164.0(5) . . . . ?
C7 Fe1 C6 C5 119.2(2) . . . . ?
C11 Fe1 C6 C5 -85.13(16) . . . . ?
C10 Fe1 C6 C5 -128.34(15) . . . . ?
C9 Fe1 C6 C5 38.04(14) . . . . ?
C14 Fe1 C6 C5 -168.04(14) . . . . ?
C8 Fe1 C11 C12 45.5(5) . . . . ?
C13 Fe1 C11 C12 -37.89(16) . . . . ?
C7 Fe1 C11 C12 -174.1(2) . . . . ?
C6 Fe1 C11 C12 153.36(15) . . . . ?
C10 Fe1 C11 C12 -119.1(2) . . . . ?
C9 Fe1 C11 C12 70.96(19) . . . . ?
C14 Fe1 C11 C12 -81.49(17) . . . . ?
C5 Fe1 C11 C12 110.57(17) . . . . ?
C8 Fe1 C11 C10 164.6(4) . . . . ?
C12 Fe1 C11 C10 119.1(2) . . . . ?
C13 Fe1 C11 C10 81.19(17) . . . . ?
C7 Fe1 C11 C10 -55.0(3) . . . . ?
C6 Fe1 C11 C10 -87.56(17) . . . . ?
C9 Fe1 C11 C10 -169.96(14) . . . . ?
C14 Fe1 C11 C10 37.60(15) . . . . ?
C5 Fe1 C11 C10 -130.35(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
Fe1 C11 C12 C13 59.61(17) . . . . ?
C10 C11 C12 Fe1 -59.45(18) . . . . ?
C8 Fe1 C12 C11 -167.97(15) . . . . ?
C13 Fe1 C12 C11 119.1(2) . . . . ?
C7 Fe1 C12 C11 164.5(5) . . . . ?
C6 Fe1 C12 C11 -51.2(3) . . . . ?
C10 Fe1 C12 C11 37.84(16) . . . . ?
C9 Fe1 C12 C11 -128.76(15) . . . . ?
C14 Fe1 C12 C11 81.66(17) . . . . ?
C5 Fe1 C12 C11 -85.44(17) . . . . ?
C8 Fe1 C12 C13 72.97(19) . . . . ?
C7 Fe1 C12 C13 45.5(6) . . . . ?
C11 Fe1 C12 C13 -119.1(2) . . . . ?
C6 Fe1 C12 C13 -170.21(17) . . . . ?
C10 Fe1 C12 C13 -81.22(17) . . . . ?
C9 Fe1 C12 C13 112.18(16) . . . . ?
C14 Fe1 C12 C13 -37.39(14) . . . . ?
C5 Fe1 C12 C13 155.50(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
Fe1 C12 C13 C14 59.60(16) . . . . ?
C11 C12 C13 Fe1 -59.75(18) . . . . ?
C8 Fe1 C13 C14 111.89(16) . . . . ?
C12 Fe1 C13 C14 -119.4(2) . . . . ?
C7 Fe1 C13 C14 71.04(18) . . . . ?
C11 Fe1 C13 C14 -81.80(16) . . . . ?
C6 Fe1 C13 C14 33.7(6) . . . . ?
C10 Fe1 C13 C14 -37.83(15) . . . . ?
C9 Fe1 C13 C14 155.36(14) . . . . ?
C5 Fe1 C13 C14 -167.31(19) . . . . ?
C8 Fe1 C13 C12 -128.73(16) . . . . ?
C7 Fe1 C13 C12 -169.58(16) . . . . ?
C11 Fe1 C13 C12 37.59(15) . . . . ?
C6 Fe1 C13 C12 153.1(5) . . . . ?
C10 Fe1 C13 C12 81.56(17) . . . . ?
C9 Fe1 C13 C12 -85.25(17) . . . . ?
C14 Fe1 C13 C12 119.4(2) . . . . ?
C5 Fe1 C13 C12 -47.9(3) . . . . ?
C12 C13 C14 C10 0.1(3) . . . . ?
Fe1 C13 C14 C10 59.35(17) . . . . ?
C12 C13 C14 Fe1 -59.27(17) . . . . ?
C8 Fe1 C14 C13 -86.88(17) . . . . ?
C12 Fe1 C14 C13 37.72(16) . . . . ?
C7 Fe1 C14 C13 -130.63(15) . . . . ?
C11 Fe1 C14 C13 81.31(17) . . . . ?
C6 Fe1 C14 C13 -171.93(15) . . . . ?
C10 Fe1 C14 C13 119.0(2) . . . . ?
C9 Fe1 C14 C13 -49.8(3) . . . . ?
C5 Fe1 C14 C13 149.2(4) . . . . ?
C8 Fe1 C14 C10 154.12(15) . . . . ?
C12 Fe1 C14 C10 -81.28(17) . . . . ?
C13 Fe1 C14 C10 -119.0(2) . . . . ?
C7 Fe1 C14 C10 110.38(15) . . . . ?
C11 Fe1 C14 C10 -37.68(14) . . . . ?
C6 Fe1 C14 C10 69.08(19) . . . . ?
C9 Fe1 C14 C10 -168.84(18) . . . . ?
C5 Fe1 C14 C10 30.2(5) . . . . ?
C13 C14 C10 C11 0.0(3) . . . . ?
Fe1 C14 C10 C11 59.39(18) . . . . ?
C13 C14 C10 Fe1 -59.37(16) . . . . ?
C12 C11 C10 C14 -0.1(3) . . . . ?
Fe1 C11 C10 C14 -59.54(18) . . . . ?
C12 C11 C10 Fe1 59.42(18) . . . . ?
C8 Fe1 C10 C14 -53.5(3) . . . . ?
C12 Fe1 C10 C14 81.69(17) . . . . ?
C13 Fe1 C10 C14 37.65(15) . . . . ?
C7 Fe1 C10 C14 -88.28(17) . . . . ?
C11 Fe1 C10 C14 119.3(2) . . . . ?
C6 Fe1 C10 C14 -131.20(15) . . . . ?
C9 Fe1 C10 C14 156.0(4) . . . . ?
C5 Fe1 C10 C14 -172.03(14) . . . . ?
C8 Fe1 C10 C11 -172.81(19) . . . . ?
C12 Fe1 C10 C11 -37.59(16) . . . . ?
C13 Fe1 C10 C11 -81.63(17) . . . . ?
C7 Fe1 C10 C11 152.43(15) . . . . ?
C6 Fe1 C10 C11 109.52(16) . . . . ?
C9 Fe1 C10 C11 36.7(5) . . . . ?
C14 Fe1 C10 C11 -119.3(2) . . . . ?
C5 Fe1 C10 C11 68.69(18) . . . . ?
N3 N1 C3 C1 0.8(3) . . . . ?
N3 N1 C3 C5 -177.1(2) . . . . ?
C6 C5 C3 C1 -162.1(2) . . . . ?
C9 C5 C3 C1 15.1(4) . . . . ?
Fe1 C5 C3 C1 -73.1(3) . . . . ?
C6 C5 C3 N1 15.2(4) . . . . ?
C9 C5 C3 N1 -167.6(2) . . . . ?
Fe1 C5 C3 N1 104.2(2) . . . . ?
N3 N5 C1 C3 -0.8(3) . . . . ?
C15 N5 C1 C3 -163.6(2) . . . . ?
N1 C3 C1 N5 0.0(3) . . . . ?
C5 C3 C1 N5 177.6(2) . . . . ?
C1 N5 C15 C16 -109.7(3) . . . . ?
N3 N5 C15 C16 88.8(3) . . . . ?
C1 N5 C15 C20 71.3(3) . . . . ?
N3 N5 C15 C20 -90.2(3) . . . . ?
C20 C15 C16 C17 0.8(4) . . . . ?
N5 C15 C16 C17 -178.1(2) . . . . ?
C20 C15 C16 C21 178.4(2) . . . . ?
N5 C15 C16 C21 -0.5(3) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C21 C16 C17 C18 -178.1(2) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C18 C19 C20 C15 -0.8(3) . . . . ?
C18 C19 C20 C24 178.1(2) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
N5 C15 C20 C19 178.8(2) . . . . ?
C16 C15 C20 C24 -179.1(2) . . . . ?
N5 C15 C20 C24 -0.1(3) . . . . ?
C15 C16 C21 C23 139.0(2) . . . . ?
C17 C16 C21 C23 -43.5(3) . . . . ?
C15 C16 C21 C22 -97.3(3) . . . . ?
C17 C16 C21 C22 80.2(3) . . . . ?
C19 C20 C24 C25 -60.1(3) . . . . ?
C15 C20 C24 C25 118.7(3) . . . . ?
C19 C20 C24 C26 65.1(3) . . . . ?
C15 C20 C24 C26 -116.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sar306m
_database_code_depnum_ccdc_archive 'CCDC 965900'
_audit_update_record             
;
2013-10-10 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Fe N3'
_chemical_formula_weight         371.26

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'
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                   7.2798(15)
_cell_length_b                   16.749(4)
_cell_length_c                   14.796(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.923(4)
_cell_angle_gamma                90.00
_cell_volume                     1751.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3395
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      27.54

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 Smart AXS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22956
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4039
_reflns_number_gt                3395
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0487P)²+2.6957P] 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         4039
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.01014(4) 0.346187(17) 0.07220(2) 0.01462(10) Uani 1 1 d . . .
N1 N 0.2835(3) 0.19550(12) 0.24051(14) 0.0257(4) Uani 1 1 d . . .
N3 N 0.3562(3) 0.12347(12) 0.25034(14) 0.0264(4) Uani 1 1 d . . .
N5 N 0.4360(3) 0.11081(11) 0.17841(12) 0.0170(4) Uani 1 1 d . . .
C15 C 0.5317(3) 0.03734(12) 0.16942(14) 0.0158(4) Uani 1 1 d . . .
C20 C 0.4296(3) -0.02353(13) 0.11602(14) 0.0168(4) Uani 1 1 d . . .
C16 C 0.7223(3) 0.02959(13) 0.21504(15) 0.0197(4) Uani 1 1 d . . .
C18 C 0.7161(3) -0.10386(13) 0.15077(15) 0.0195(4) Uani 1 1 d . . .
C1 C 0.4152(3) 0.17550(13) 0.12259(15) 0.0168(4) Uani 1 1 d . . .
H1 H 0.4582 0.1820 0.0687 0.020 Uiso 1 1 calc R . .
C3 C 0.3171(3) 0.22952(12) 0.16223(14) 0.0161(4) Uani 1 1 d . . .
C23 C 0.2232(3) -0.01408(15) 0.06816(17) 0.0242(5) Uani 1 1 d . . .
H23A H 0.1807 0.0379 0.0815 0.036 Uiso 1 1 calc R . .
H23B H 0.1508 -0.0542 0.0904 0.036 Uiso 1 1 calc R . .
H23C H 0.2068 -0.0199 0.0021 0.036 Uiso 1 1 calc R . .
C11 C -0.2340(3) 0.30448(15) 0.11749(17) 0.0259(5) Uani 1 1 d . . .
H11 H -0.2384 0.2979 0.1794 0.031 Uiso 1 1 calc R . .
C21 C 0.8279(4) 0.09556(15) 0.27543(19) 0.0296(5) Uani 1 1 d . . .
H21A H 0.9565 0.0793 0.3007 0.044 Uiso 1 1 calc R . .
H21B H 0.7682 0.1064 0.3254 0.044 Uiso 1 1 calc R . .
H21C H 0.8261 0.1429 0.2386 0.044 Uiso 1 1 calc R . .
C22 C 0.8166(4) -0.18025(15) 0.13811(17) 0.0293(5) Uani 1 1 d . . .
H22A H 0.7290 -0.2161 0.0991 0.044 Uiso 1 1 calc R . .
H22B H 0.8660 -0.2047 0.1977 0.044 Uiso 1 1 calc R . .
H22C H 0.9187 -0.1687 0.1094 0.044 Uiso 1 1 calc R . .
C17 C 0.8120(3) -0.04192(14) 0.20441(15) 0.0213(5) Uani 1 1 d . . .
H17 H 0.9392 -0.0484 0.2339 0.026 Uiso 1 1 calc R . .
C19 C 0.5251(3) -0.09401(13) 0.10813(15) 0.0185(4) Uani 1 1 d . . .
H19 H 0.4595 -0.1358 0.0734 0.022 Uiso 1 1 calc R . .
C8 C 0.1504(3) 0.43982(13) 0.13577(16) 0.0201(4) Uani 1 1 d . . .
H8 H 0.1061 0.4873 0.1553 0.024 Uiso 1 1 calc R . .
C12 C -0.2870(3) 0.37413(15) 0.06312(19) 0.0273(5) Uani 1 1 d . . .
H12 H -0.3326 0.4212 0.0829 0.033 Uiso 1 1 calc R . .
C14 C -0.1886(3) 0.28055(15) -0.02872(16) 0.0229(5) Uani 1 1 d . . .
H14 H -0.1583 0.2555 -0.0794 0.028 Uiso 1 1 calc R . .
C10 C -0.1730(3) 0.24637(14) 0.06093(16) 0.0223(5) Uani 1 1 d . . .
H10 H -0.1305 0.1952 0.0793 0.027 Uiso 1 1 calc R . .
C5 C 0.2582(3) 0.31039(12) 0.13362(15) 0.0159(4) Uani 1 1 d . . .
C7 C 0.1859(3) 0.42551(13) 0.04671(16) 0.0195(4) Uani 1 1 d . . .
H7 H 0.1686 0.4619 -0.0021 0.023 Uiso 1 1 calc R . .
C6 C 0.2526(3) 0.34579(12) 0.04531(15) 0.0170(4) Uani 1 1 d . . .
H6 H 0.2867 0.3211 -0.0045 0.020 Uiso 1 1 calc R . .
C9 C 0.1940(3) 0.36908(13) 0.18963(15) 0.0183(4) Uani 1 1 d . . .
H9 H 0.1830 0.3621 0.2505 0.022 Uiso 1 1 calc R . .
C13 C -0.2583(3) 0.35930(15) -0.02712(18) 0.0259(5) Uani 1 1 d . . .
H13 H -0.2813 0.3952 -0.0766 0.031 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 2.030(2) . ?
Fe1 C9 2.033(2) . ?
Fe1 C10 2.033(2) . ?
Fe1 C5 2.036(2) . ?
Fe1 C12 2.042(2) . ?
Fe1 C8 2.045(2) . ?
Fe1 C6 2.045(2) . ?
Fe1 C14 2.047(2) . ?
Fe1 C13 2.048(2) . ?
Fe1 C7 2.050(2) . ?
N1 N3 1.311(3) . ?
N1 C3 1.365(3) . ?
N3 N5 1.346(3) . ?
N5 C1 1.349(3) . ?
N5 C15 1.436(3) . ?
C15 C20 1.390(3) . ?
C15 C16 1.395(3) . ?
C20 C19 1.389(3) . ?
C20 C23 1.507(3) . ?
C16 C17 1.391(3) . ?
C16 C21 1.510(3) . ?
C18 C17 1.388(3) . ?
C18 C19 1.392(3) . ?
C18 C22 1.507(3) . ?
C1 C3 1.369(3) . ?
C3 C5 1.453(3) . ?
C11 C12 1.417(4) . ?
C11 C10 1.423(3) . ?
C8 C9 1.421(3) . ?
C8 C7 1.423(3) . ?
C12 C13 1.422(4) . ?
C14 C13 1.415(3) . ?
C14 C10 1.424(3) . ?
C5 C6 1.426(3) . ?
C5 C9 1.434(3) . ?
C7 C6 1.423(3) . ?

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
C11 Fe1 C9 105.24(10) . . ?
C11 Fe1 C10 41.00(10) . . ?
C9 Fe1 C10 121.15(9) . . ?
C11 Fe1 C5 120.77(10) . . ?
C9 Fe1 C5 41.28(8) . . ?
C10 Fe1 C5 105.80(9) . . ?
C11 Fe1 C12 40.72(11) . . ?
C9 Fe1 C12 121.34(10) . . ?
C10 Fe1 C12 68.66(10) . . ?
C5 Fe1 C12 157.30(10) . . ?
C11 Fe1 C8 121.84(10) . . ?
C9 Fe1 C8 40.78(9) . . ?
C10 Fe1 C8 157.80(10) . . ?
C5 Fe1 C8 68.90(8) . . ?
C12 Fe1 C8 107.47(9) . . ?
C11 Fe1 C6 157.83(10) . . ?
C9 Fe1 C6 68.97(9) . . ?
C10 Fe1 C6 122.39(9) . . ?
C5 Fe1 C6 40.91(8) . . ?
C12 Fe1 C6 160.48(10) . . ?
C8 Fe1 C6 68.55(9) . . ?
C11 Fe1 C14 68.72(10) . . ?
C9 Fe1 C14 158.39(10) . . ?
C10 Fe1 C14 40.85(9) . . ?
C5 Fe1 C14 122.64(9) . . ?
C12 Fe1 C14 68.42(10) . . ?
C8 Fe1 C14 159.95(10) . . ?
C6 Fe1 C14 108.38(9) . . ?
C11 Fe1 C13 68.54(10) . . ?
C9 Fe1 C13 158.51(10) . . ?
C10 Fe1 C13 68.47(10) . . ?
C5 Fe1 C13 159.66(10) . . ?
C12 Fe1 C13 40.70(10) . . ?
C8 Fe1 C13 123.75(10) . . ?
C6 Fe1 C13 124.44(10) . . ?
C14 Fe1 C13 40.44(10) . . ?
C11 Fe1 C7 159.02(10) . . ?
C9 Fe1 C7 68.70(9) . . ?
C10 Fe1 C7 159.36(9) . . ?
C5 Fe1 C7 68.74(9) . . ?
C12 Fe1 C7 124.01(10) . . ?
C8 Fe1 C7 40.67(9) . . ?
C6 Fe1 C7 40.65(8) . . ?
C14 Fe1 C7 124.15(9) . . ?
C13 Fe1 C7 109.35(10) . . ?
N3 N1 C3 109.18(18) . . ?
N1 N3 N5 107.25(18) . . ?
N3 N5 C1 110.56(18) . . ?
N3 N5 C15 121.29(17) . . ?
C1 N5 C15 128.13(18) . . ?
C20 C15 C16 122.7(2) . . ?
C20 C15 N5 118.43(18) . . ?
C16 C15 N5 118.89(19) . . ?
C19 C20 C15 117.45(19) . . ?
C19 C20 C23 120.8(2) . . ?
C15 C20 C23 121.7(2) . . ?
C17 C16 C15 117.7(2) . . ?
C17 C16 C21 120.7(2) . . ?
C15 C16 C21 121.6(2) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 C22 120.9(2) . . ?
C19 C18 C22 120.4(2) . . ?
N5 C1 C3 105.19(18) . . ?
N1 C3 C1 107.82(19) . . ?
N1 C3 C5 122.43(19) . . ?
C1 C3 C5 129.7(2) . . ?
C12 C11 C10 108.1(2) . . ?
C12 C11 Fe1 70.11(13) . . ?
C10 C11 Fe1 69.63(13) . . ?
C18 C17 C16 121.5(2) . . ?
C20 C19 C18 121.9(2) . . ?
C9 C8 C7 108.24(19) . . ?
C9 C8 Fe1 69.16(12) . . ?
C7 C8 Fe1 69.88(12) . . ?
C11 C12 C13 107.9(2) . . ?
C11 C12 Fe1 69.16(13) . . ?
C13 C12 Fe1 69.86(13) . . ?
C13 C14 C10 107.9(2) . . ?
C13 C14 Fe1 69.79(13) . . ?
C10 C14 Fe1 69.03(13) . . ?
C11 C10 C14 107.9(2) . . ?
C11 C10 Fe1 69.37(13) . . ?
C14 C10 Fe1 70.12(13) . . ?
C6 C5 C9 107.63(18) . . ?
C6 C5 C3 126.58(19) . . ?
C9 C5 C3 125.79(19) . . ?
C6 C5 Fe1 69.89(12) . . ?
C9 C5 Fe1 69.23(12) . . ?
C3 C5 Fe1 126.07(15) . . ?
C6 C7 C8 108.08(19) . . ?
C6 C7 Fe1 69.49(12) . . ?
C8 C7 Fe1 69.45(12) . . ?
C7 C6 C5 108.14(19) . . ?
C7 C6 Fe1 69.86(12) . . ?
C5 C6 Fe1 69.20(12) . . ?
C8 C9 C5 107.90(19) . . ?
C8 C9 Fe1 70.06(12) . . ?
C5 C9 Fe1 69.49(12) . . ?
C14 C13 C12 108.2(2) . . ?
C14 C13 Fe1 69.77(13) . . ?
C12 C13 Fe1 69.44(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.080
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sar388m
_database_code_depnum_ccdc_archive 'CCDC 1015508'
_audit_update_record             
;
2014-07-22 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 B F4 Fe N3'
_chemical_formula_weight         473.10

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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'
'-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                   9.213(5)
_cell_length_b                   9.618(5)
_cell_length_c                   47.215(5)
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_volume                     4184(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2201
_cell_measurement_theta_min      0.86
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart AXS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21218
_diffrn_reflns_av_R_equivalents  0.1311
_diffrn_reflns_av_sigmaI/netI    0.0864
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         0.86
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3659
_reflns_number_gt                2201
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0874P)²+11.4952P] 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         3659
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2027
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.97482(9) 0.18597(9) 0.045730(18) 0.0214(3) Uani 1 1 d . . .
F4 F 0.4881(5) 0.1573(5) 0.09175(9) 0.0526(12) Uani 1 1 d . . .
F3 F 0.4354(6) 0.1660(5) 0.13826(11) 0.0695(15) Uani 1 1 d . . .
N1 N 1.1167(6) 0.2753(5) 0.12095(11) 0.0247(13) Uani 1 1 d . . .
C5 C 1.0733(7) 0.1088(6) 0.08062(13) 0.0208(14) Uani 1 1 d . . .
C1 C 0.9851(7) 0.0968(6) 0.13204(12) 0.0226(14) Uani 1 1 d . . .
H1 H 0.9307 0.0154 0.1318 0.027 Uiso 1 1 calc R . .
F1 F 0.6311(6) 0.0496(5) 0.12295(11) 0.0725(16) Uani 1 1 d . . .
N3 N 1.0903(6) 0.2892(6) 0.14824(12) 0.0298(13) Uani 1 1 d . . .
C3 C 1.0560(7) 0.1572(6) 0.10956(13) 0.0226(15) Uani 1 1 d . . .
C7 C 1.0261(7) -0.0194(6) 0.04075(12) 0.0234(14) Uani 1 1 d . . .
H7 H 0.9832 -0.0815 0.0282 0.028 Uiso 1 1 calc R . .
C19 C 0.8569(8) 0.2214(8) 0.22645(15) 0.0385(19) Uani 1 1 d . . .
H19 H 0.7899 0.2763 0.2361 0.046 Uiso 1 1 calc R . .
N5 N 1.0101(6) 0.1790(5) 0.15447(10) 0.0262(12) Uani 1 1 d . . .
C6 C 0.9799(7) 0.0072(6) 0.06867(13) 0.0225(14) Uani 1 1 d . . .
H6 H 0.9016 -0.0346 0.0777 0.027 Uiso 1 1 calc R . .
F2 F 0.6276(6) 0.2843(5) 0.12071(11) 0.0749(17) Uani 1 1 d . . .
C17 C 1.0269(8) 0.0354(7) 0.22676(14) 0.0347(17) Uani 1 1 d . . .
H17 H 1.0759 -0.0338 0.2367 0.042 Uiso 1 1 calc R . .
C15 C 0.9755(7) 0.1558(7) 0.18411(14) 0.0277(15) Uani 1 1 d . . .
C18 C 0.9325(8) 0.1224(8) 0.24129(14) 0.0347(18) Uani 1 1 d . . .
B1 B 0.5467(10) 0.1632(8) 0.1186(2) 0.041(2) Uani 1 1 d . . .
C20 C 0.8768(8) 0.2428(7) 0.19756(13) 0.0300(16) Uani 1 1 d . . .
C10 C 0.7646(7) 0.2528(7) 0.04706(15) 0.0309(16) Uani 1 1 d . . .
H10 H 0.6884 0.2099 0.0566 0.037 Uiso 1 1 calc R . .
C16 C 1.0502(8) 0.0491(7) 0.19769(14) 0.0322(17) Uani 1 1 d . . .
C23 C 0.7970(9) 0.3541(9) 0.18192(16) 0.051(2) Uani 1 1 d . . .
H23C H 0.7342 0.4028 0.1948 0.076 Uiso 1 1 calc R . .
H23A H 0.7401 0.3129 0.1671 0.076 Uiso 1 1 calc R . .
H23B H 0.8654 0.4182 0.1738 0.076 Uiso 1 1 calc R . .
C21 C 1.1553(8) -0.0442(8) 0.18237(15) 0.0379(18) Uani 1 1 d . . .
H21C H 1.1579 -0.0195 0.1627 0.057 Uiso 1 1 calc R . .
H21B H 1.1248 -0.1392 0.1843 0.057 Uiso 1 1 calc R . .
H21A H 1.2504 -0.0335 0.1904 0.057 Uiso 1 1 calc R . .
C33 C 1.2017(8) 0.3816(7) 0.10679(14) 0.0298(16) Uani 1 1 d . . .
H34B H 1.2058 0.4633 0.1185 0.045 Uiso 1 1 calc R . .
H34C H 1.1573 0.4043 0.0890 0.045 Uiso 1 1 calc R . .
H33A H 1.2983 0.3477 0.1036 0.045 Uiso 1 1 calc R . .
C11 C 0.8065(7) 0.2267(7) 0.01897(14) 0.0308(17) Uani 1 1 d . . .
H11 H 0.7631 0.1638 0.0066 0.037 Uiso 1 1 calc R . .
C22 C 0.9196(9) 0.1096(9) 0.27313(15) 0.050(2) Uani 1 1 d . . .
H22B H 0.9805 0.0352 0.2796 0.075 Uiso 1 1 calc R . .
H22A H 0.8206 0.0903 0.2781 0.075 Uiso 1 1 calc R . .
H22C H 0.9495 0.1951 0.2818 0.075 Uiso 1 1 calc R . .
C12 C 0.9282(8) 0.3144(7) 0.01274(15) 0.0356(17) Uani 1 1 d . . .
H12 H 0.9786 0.3173 -0.0043 0.043 Uiso 1 1 calc R . .
C9 C 1.1789(7) 0.1445(7) 0.05967(13) 0.0241(15) Uani 1 1 d . . .
H9 H 1.2538 0.2085 0.0617 0.029 Uiso 1 1 calc R . .
C8 C 1.1488(7) 0.0643(6) 0.03514(13) 0.0236(15) Uani 1 1 d . . .
H8 H 1.2009 0.0665 0.0183 0.028 Uiso 1 1 calc R . .
C13 C 0.9583(8) 0.3948(7) 0.03674(14) 0.0319(17) Uani 1 1 d . . .
H13 H 1.0307 0.4618 0.0383 0.038 Uiso 1 1 calc R . .
C14 C 0.8582(8) 0.3558(7) 0.05850(15) 0.0314(17) Uani 1 1 d . . .
H14 H 0.8550 0.3915 0.0768 0.038 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 2.022(6) . ?
Fe1 C9 2.032(7) . ?
Fe1 C6 2.032(6) . ?
Fe1 C12 2.034(7) . ?
Fe1 C11 2.038(7) . ?
Fe1 C10 2.041(7) . ?
Fe1 C7 2.045(6) . ?
Fe1 C14 2.046(7) . ?
Fe1 C8 2.046(6) . ?
Fe1 C13 2.059(7) . ?
F4 B1 1.378(10) . ?
F3 B1 1.384(10) . ?
N1 N3 1.318(7) . ?
N1 C3 1.376(8) . ?
N1 C33 1.452(8) . ?
C5 C6 1.418(8) . ?
C5 C9 1.430(9) . ?
C5 C3 1.452(8) . ?
C1 N5 1.341(8) . ?
C1 C3 1.376(9) . ?
F1 B1 1.357(9) . ?
N3 N5 1.325(7) . ?
C7 C6 1.409(8) . ?
C7 C8 1.413(9) . ?
C19 C18 1.372(10) . ?
C19 C20 1.392(9) . ?
N5 C15 1.452(8) . ?
F2 B1 1.386(9) . ?
C17 C18 1.388(10) . ?
C17 C16 1.395(9) . ?
C15 C20 1.389(9) . ?
C15 C16 1.393(10) . ?
C18 C22 1.513(10) . ?
C20 C23 1.494(10) . ?
C10 C11 1.404(9) . ?
C10 C14 1.420(9) . ?
C16 C21 1.506(10) . ?
C11 C12 1.434(10) . ?
C12 C13 1.400(10) . ?
C9 C8 1.419(9) . ?
C13 C14 1.431(10) . ?

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
C5 Fe1 C9 41.3(2) . . ?
C5 Fe1 C6 41.0(2) . . ?
C9 Fe1 C6 68.9(3) . . ?
C5 Fe1 C12 160.4(3) . . ?
C9 Fe1 C12 124.2(3) . . ?
C6 Fe1 C12 157.9(3) . . ?
C5 Fe1 C11 156.5(3) . . ?
C9 Fe1 C11 160.5(3) . . ?
C6 Fe1 C11 120.7(3) . . ?
C12 Fe1 C11 41.2(3) . . ?
C5 Fe1 C10 121.1(3) . . ?
C9 Fe1 C10 158.4(3) . . ?
C6 Fe1 C10 105.8(3) . . ?
C12 Fe1 C10 68.4(3) . . ?
C11 Fe1 C10 40.3(3) . . ?
C5 Fe1 C7 68.6(2) . . ?
C9 Fe1 C7 68.5(3) . . ?
C6 Fe1 C7 40.4(2) . . ?
C12 Fe1 C7 123.2(3) . . ?
C11 Fe1 C7 106.8(3) . . ?
C10 Fe1 C7 121.8(3) . . ?
C5 Fe1 C14 106.8(3) . . ?
C9 Fe1 C14 123.2(3) . . ?
C6 Fe1 C14 122.0(3) . . ?
C12 Fe1 C14 68.3(3) . . ?
C11 Fe1 C14 68.3(3) . . ?
C10 Fe1 C14 40.7(3) . . ?
C7 Fe1 C14 157.9(3) . . ?
C5 Fe1 C8 68.8(2) . . ?
C9 Fe1 C8 40.7(2) . . ?
C6 Fe1 C8 68.2(2) . . ?
C12 Fe1 C8 109.0(3) . . ?
C11 Fe1 C8 123.7(3) . . ?
C10 Fe1 C8 158.5(3) . . ?
C7 Fe1 C8 40.4(3) . . ?
C14 Fe1 C8 160.0(3) . . ?
C5 Fe1 C13 124.0(3) . . ?
C9 Fe1 C13 109.1(3) . . ?
C6 Fe1 C13 159.5(3) . . ?
C12 Fe1 C13 40.0(3) . . ?
C11 Fe1 C13 68.2(3) . . ?
C10 Fe1 C13 68.2(3) . . ?
C7 Fe1 C13 159.4(3) . . ?
C14 Fe1 C13 40.8(3) . . ?
C8 Fe1 C13 124.4(3) . . ?
N3 N1 C3 113.0(5) . . ?
N3 N1 C33 118.6(5) . . ?
C3 N1 C33 128.4(5) . . ?
C6 C5 C9 107.6(5) . . ?
C6 C5 C3 121.9(5) . . ?
C9 C5 C3 130.4(6) . . ?
C6 C5 Fe1 69.9(3) . . ?
C9 C5 Fe1 69.7(4) . . ?
C3 C5 Fe1 126.9(4) . . ?
N5 C1 C3 106.2(5) . . ?
N1 N3 N5 103.8(5) . . ?
C1 C3 N1 103.9(5) . . ?
C1 C3 C5 130.0(6) . . ?
N1 C3 C5 126.1(6) . . ?
C6 C7 C8 108.2(5) . . ?
C6 C7 Fe1 69.3(3) . . ?
C8 C7 Fe1 69.9(4) . . ?
C18 C19 C20 122.4(7) . . ?
N3 N5 C1 113.1(5) . . ?
N3 N5 C15 117.3(5) . . ?
C1 N5 C15 129.2(5) . . ?
C7 C6 C5 108.3(5) . . ?
C7 C6 Fe1 70.3(3) . . ?
C5 C6 Fe1 69.1(3) . . ?
C18 C17 C16 121.7(7) . . ?
C20 C15 C16 123.8(6) . . ?
C20 C15 N5 119.5(6) . . ?
C16 C15 N5 116.6(6) . . ?
C19 C18 C17 118.9(6) . . ?
C19 C18 C22 121.6(7) . . ?
C17 C18 C22 119.4(7) . . ?
F1 B1 F4 109.3(7) . . ?
F1 B1 F3 109.7(7) . . ?
F4 B1 F3 109.1(7) . . ?
F1 B1 F2 110.9(8) . . ?
F4 B1 F2 108.2(7) . . ?
F3 B1 F2 109.5(7) . . ?
C15 C20 C19 116.5(7) . . ?
C15 C20 C23 121.8(6) . . ?
C19 C20 C23 121.7(7) . . ?
C11 C10 C14 108.5(6) . . ?
C11 C10 Fe1 69.8(4) . . ?
C14 C10 Fe1 69.9(4) . . ?
C15 C16 C17 116.5(6) . . ?
C15 C16 C21 122.4(6) . . ?
C17 C16 C21 121.0(6) . . ?
C10 C11 C12 107.7(6) . . ?
C10 C11 Fe1 70.0(4) . . ?
C12 C11 Fe1 69.2(4) . . ?
C13 C12 C11 108.3(6) . . ?
C13 C12 Fe1 71.0(4) . . ?
C11 C12 Fe1 69.6(4) . . ?
C8 C9 C5 107.5(6) . . ?
C8 C9 Fe1 70.2(4) . . ?
C5 C9 Fe1 69.0(4) . . ?
C7 C8 C9 108.3(5) . . ?
C7 C8 Fe1 69.7(4) . . ?
C9 C8 Fe1 69.1(4) . . ?
C12 C13 C14 108.0(6) . . ?
C12 C13 Fe1 69.0(4) . . ?
C14 C13 Fe1 69.1(4) . . ?
C10 C14 C13 107.5(6) . . ?
C10 C14 Fe1 69.5(4) . . ?
C13 C14 Fe1 70.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.176
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ortho_a
_database_code_depnum_ccdc_archive 'CCDC 1022581'
_audit_update_record             
;
2014-09-02 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 Au Cl Fe N3'
_chemical_formula_weight         659.78

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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.3929(14)
_cell_length_b                   9.2832(4)
_cell_length_c                   17.3954(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.428(2)
_cell_angle_gamma                90.00
_cell_volume                     4746.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4447
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.41

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2576
_exptl_absorpt_coefficient_mu    6.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2322
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 D8 Venture'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19765
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.41
_reflns_number_total             4866
_reflns_number_gt                4447
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0074P)²+6.7982P] 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         4866
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0170
_refine_ls_wR_factor_ref         0.0349
_refine_ls_wR_factor_gt          0.0339
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.003
_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
Au1 Au 0.648018(3) 0.904726(9) 0.569982(5) 0.01145(3) Uani 1 1 d . . .
Fe1 Fe 0.723971(12) 0.56441(4) 0.672991(19) 0.01126(8) Uani 1 1 d . . .
Cl1 Cl 0.65920(2) 1.12645(7) 0.62387(4) 0.02118(14) Uani 1 1 d . . .
N5 N 0.60344(7) 0.6651(2) 0.48340(11) 0.0115(4) Uani 1 1 d . . .
N3 N 0.60680(7) 0.5322(2) 0.45411(11) 0.0130(4) Uani 1 1 d . . .
N1 N 0.64793(7) 0.4910(2) 0.47699(11) 0.0121(4) Uani 1 1 d . . .
C3 C 0.66967(8) 0.5923(2) 0.52034(13) 0.0107(5) Uani 1 1 d . . .
C11 C 0.72720(9) 0.4943(3) 0.78471(13) 0.0154(5) Uani 1 1 d . . .
H11 H 0.7503 0.4358 0.8069 0.019 Uiso 1 1 calc R . .
C1 C 0.64050(8) 0.7108(3) 0.52386(13) 0.0110(5) Uani 1 1 d . . .
C5 C 0.71400(8) 0.5727(3) 0.55661(13) 0.0119(5) Uani 1 1 d . . .
C10 C 0.68645(9) 0.4442(3) 0.74860(14) 0.0169(6) Uani 1 1 d . . .
H10 H 0.6777 0.3463 0.7424 0.020 Uiso 1 1 calc R . .
C9 C 0.74244(8) 0.6892(3) 0.58207(13) 0.0132(5) Uani 1 1 d . . .
H9 H 0.7360 0.7889 0.5761 0.016 Uiso 1 1 calc R . .
C12 C 0.72705(9) 0.6469(3) 0.78158(14) 0.0166(6) Uani 1 1 d . . .
H12 H 0.7502 0.7087 0.8012 0.020 Uiso 1 1 calc R . .
C6 C 0.73633(9) 0.4406(3) 0.57815(14) 0.0147(5) Uani 1 1 d . . .
H6 H 0.7252 0.3459 0.5693 0.018 Uiso 1 1 calc R . .
C13 C 0.68627(9) 0.6914(3) 0.74398(14) 0.0167(6) Uani 1 1 d . . .
H13 H 0.6773 0.7880 0.7342 0.020 Uiso 1 1 calc R . .
C20 C 0.55128(9) 0.8097(2) 0.40518(14) 0.0130(5) Uani 1 1 d . . .
C15 C 0.55992(8) 0.7375(2) 0.47396(14) 0.0112(5) Uani 1 1 d . . .
C14 C 0.66138(9) 0.5657(3) 0.72363(14) 0.0170(6) Uani 1 1 d . . .
H14 H 0.6328 0.5636 0.6977 0.020 Uiso 1 1 calc R . .
C7 C 0.77811(9) 0.4774(3) 0.61501(14) 0.0164(6) Uani 1 1 d . . .
H7 H 0.7999 0.4112 0.6346 0.020 Uiso 1 1 calc R . .
C24 C 0.58639(9) 0.8227(3) 0.34222(14) 0.0169(6) Uani 1 1 d . . .
H24 H 0.6154 0.7801 0.3622 0.020 Uiso 1 1 calc R . .
C19 C 0.50790(9) 0.8682(3) 0.39618(15) 0.0159(6) Uani 1 1 d . . .
H19 H 0.5005 0.9187 0.3503 0.019 Uiso 1 1 calc R . .
C33 C 0.66368(10) 0.3489(3) 0.45098(15) 0.0186(6) Uani 1 1 d . . .
H33A H 0.6599 0.2786 0.4925 0.028 Uiso 1 1 calc R . .
H33B H 0.6959 0.3547 0.4371 0.028 Uiso 1 1 calc R . .
H33C H 0.6458 0.3187 0.4061 0.028 Uiso 1 1 calc R . .
C17 C 0.48572(9) 0.7841(3) 0.52069(14) 0.0169(6) Uani 1 1 d . . .
H17 H 0.4632 0.7770 0.5595 0.020 Uiso 1 1 calc R . .
C8 C 0.78168(9) 0.6299(3) 0.61760(14) 0.0152(5) Uani 1 1 d . . .
H8 H 0.8062 0.6830 0.6394 0.018 Uiso 1 1 calc R . .
C25 C 0.57213(10) 0.7360(3) 0.27117(15) 0.0254(6) Uani 1 1 d . . .
H25A H 0.5954 0.7457 0.2314 0.038 Uiso 1 1 calc R . .
H25B H 0.5430 0.7727 0.2515 0.038 Uiso 1 1 calc R . .
H25C H 0.5688 0.6343 0.2851 0.038 Uiso 1 1 calc R . .
C16 C 0.52859(8) 0.7237(3) 0.53313(14) 0.0126(5) Uani 1 1 d . . .
C18 C 0.47554(9) 0.8543(3) 0.45237(15) 0.0196(6) Uani 1 1 d . . .
H18 H 0.4460 0.8932 0.4443 0.024 Uiso 1 1 calc R . .
C22 C 0.50491(10) 0.5347(3) 0.63028(15) 0.0224(6) Uani 1 1 d . . .
H22A H 0.5138 0.4887 0.6788 0.034 Uiso 1 1 calc R . .
H22B H 0.5032 0.4618 0.5896 0.034 Uiso 1 1 calc R . .
H22C H 0.4751 0.5804 0.6361 0.034 Uiso 1 1 calc R . .
C23 C 0.54519(10) 0.7605(3) 0.67330(14) 0.0206(6) Uani 1 1 d . . .
H23A H 0.5527 0.7117 0.7217 0.031 Uiso 1 1 calc R . .
H23B H 0.5166 0.8134 0.6790 0.031 Uiso 1 1 calc R . .
H23C H 0.5696 0.8279 0.6603 0.031 Uiso 1 1 calc R . .
C21 C 0.54003(9) 0.6483(3) 0.60897(14) 0.0149(5) Uani 1 1 d . . .
H21 H 0.5700 0.5988 0.6029 0.018 Uiso 1 1 calc R . .
C26 C 0.59593(11) 0.9796(3) 0.32197(18) 0.0332(7) Uani 1 1 d . . .
H26A H 0.6188 0.9838 0.2813 0.050 Uiso 1 1 calc R . .
H26B H 0.6074 1.0302 0.3676 0.050 Uiso 1 1 calc R . .
H26C H 0.5678 1.0256 0.3040 0.050 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Au1 C1 1.982(2) . ?
Au1 Cl1 2.2844(6) . ?
Fe1 C9 2.037(2) . ?
Fe1 C12 2.040(2) . ?
Fe1 C13 2.040(3) . ?
Fe1 C5 2.045(2) . ?
Fe1 C6 2.045(2) . ?
Fe1 C14 2.046(3) . ?
Fe1 C8 2.049(3) . ?
Fe1 C11 2.051(2) . ?
Fe1 C10 2.053(3) . ?
Fe1 C7 2.055(3) . ?
N5 N3 1.338(3) . ?
N5 C1 1.360(3) . ?
N5 C15 1.453(3) . ?
N3 N1 1.327(3) . ?
N1 C3 1.362(3) . ?
N1 C33 1.470(3) . ?
C3 C1 1.397(3) . ?
C3 C5 1.455(3) . ?
C11 C12 1.418(4) . ?
C11 C10 1.426(4) . ?
C5 C9 1.434(3) . ?
C5 C6 1.440(3) . ?
C10 C14 1.414(4) . ?
C9 C8 1.416(3) . ?
C12 C13 1.423(3) . ?
C6 C7 1.423(3) . ?
C13 C14 1.421(4) . ?
C20 C15 1.393(3) . ?
C20 C19 1.393(3) . ?
C20 C24 1.515(4) . ?
C15 C16 1.392(3) . ?
C7 C8 1.420(4) . ?
C24 C26 1.525(4) . ?
C24 C25 1.530(3) . ?
C19 C18 1.375(4) . ?
C17 C18 1.387(4) . ?
C17 C16 1.395(3) . ?
C16 C21 1.528(3) . ?
C22 C21 1.524(4) . ?
C23 C21 1.535(3) . ?

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
C1 Au1 Cl1 178.08(7) . . ?
C9 Fe1 C12 119.69(10) . . ?
C9 Fe1 C13 106.89(10) . . ?
C12 Fe1 C13 40.81(10) . . ?
C9 Fe1 C5 41.14(9) . . ?
C12 Fe1 C5 155.19(10) . . ?
C13 Fe1 C5 120.19(10) . . ?
C9 Fe1 C6 69.10(10) . . ?
C12 Fe1 C6 161.99(10) . . ?
C13 Fe1 C6 155.97(10) . . ?
C5 Fe1 C6 41.22(9) . . ?
C9 Fe1 C14 125.22(10) . . ?
C12 Fe1 C14 68.46(10) . . ?
C13 Fe1 C14 40.69(10) . . ?
C5 Fe1 C14 107.66(10) . . ?
C6 Fe1 C14 121.08(10) . . ?
C9 Fe1 C8 40.54(10) . . ?
C12 Fe1 C8 107.04(10) . . ?
C13 Fe1 C8 124.65(11) . . ?
C5 Fe1 C8 68.67(10) . . ?
C6 Fe1 C8 68.58(10) . . ?
C14 Fe1 C8 161.98(10) . . ?
C9 Fe1 C11 154.87(10) . . ?
C12 Fe1 C11 40.55(10) . . ?
C13 Fe1 C11 68.36(10) . . ?
C5 Fe1 C11 162.81(10) . . ?
C6 Fe1 C11 125.36(10) . . ?
C14 Fe1 C11 68.23(10) . . ?
C8 Fe1 C11 120.47(10) . . ?
C9 Fe1 C10 162.57(10) . . ?
C12 Fe1 C10 68.35(10) . . ?
C13 Fe1 C10 68.25(11) . . ?
C5 Fe1 C10 125.53(10) . . ?
C6 Fe1 C10 108.10(10) . . ?
C14 Fe1 C10 40.36(10) . . ?
C8 Fe1 C10 155.94(10) . . ?
C11 Fe1 C10 40.68(10) . . ?
C9 Fe1 C7 68.32(10) . . ?
C12 Fe1 C7 124.94(10) . . ?
C13 Fe1 C7 161.78(10) . . ?
C5 Fe1 C7 68.58(10) . . ?
C6 Fe1 C7 40.60(10) . . ?
C14 Fe1 C7 156.28(10) . . ?
C8 Fe1 C7 40.47(10) . . ?
C11 Fe1 C7 108.05(10) . . ?
C10 Fe1 C7 121.49(11) . . ?
N3 N5 C1 115.1(2) . . ?
N3 N5 C15 116.80(18) . . ?
C1 N5 C15 127.9(2) . . ?
N1 N3 N5 102.80(18) . . ?
N3 N1 C3 112.92(19) . . ?
N3 N1 C33 117.06(19) . . ?
C3 N1 C33 130.0(2) . . ?
N1 C3 C1 106.4(2) . . ?
N1 C3 C5 124.7(2) . . ?
C1 C3 C5 128.9(2) . . ?
C12 C11 C10 107.9(2) . . ?
C12 C11 Fe1 69.30(14) . . ?
C10 C11 Fe1 69.73(14) . . ?
N5 C1 C3 102.8(2) . . ?
N5 C1 Au1 125.40(17) . . ?
C3 C1 Au1 131.79(18) . . ?
C9 C5 C6 107.3(2) . . ?
C9 C5 C3 123.9(2) . . ?
C6 C5 C3 128.6(2) . . ?
C9 C5 Fe1 69.14(13) . . ?
C6 C5 Fe1 69.42(13) . . ?
C3 C5 Fe1 123.74(18) . . ?
C14 C10 C11 108.0(2) . . ?
C14 C10 Fe1 69.55(15) . . ?
C11 C10 Fe1 69.59(14) . . ?
C8 C9 C5 108.2(2) . . ?
C8 C9 Fe1 70.19(14) . . ?
C5 C9 Fe1 69.72(14) . . ?
C11 C12 C13 108.1(2) . . ?
C11 C12 Fe1 70.15(14) . . ?
C13 C12 Fe1 69.62(14) . . ?
C7 C6 C5 107.6(2) . . ?
C7 C6 Fe1 70.08(14) . . ?
C5 C6 Fe1 69.37(14) . . ?
C14 C13 C12 107.9(2) . . ?
C14 C13 Fe1 69.86(14) . . ?
C12 C13 Fe1 69.57(14) . . ?
C15 C20 C19 116.4(2) . . ?
C15 C20 C24 122.6(2) . . ?
C19 C20 C24 121.0(2) . . ?
C16 C15 C20 124.2(2) . . ?
C16 C15 N5 117.4(2) . . ?
C20 C15 N5 118.3(2) . . ?
C10 C14 C13 108.2(2) . . ?
C10 C14 Fe1 70.09(15) . . ?
C13 C14 Fe1 69.45(15) . . ?
C8 C7 C6 108.5(2) . . ?
C8 C7 Fe1 69.53(15) . . ?
C6 C7 Fe1 69.32(15) . . ?
C20 C24 C26 111.7(2) . . ?
C20 C24 C25 111.0(2) . . ?
C26 C24 C25 111.4(2) . . ?
C18 C19 C20 121.4(2) . . ?
C18 C17 C16 120.7(2) . . ?
C9 C8 C7 108.3(2) . . ?
C9 C8 Fe1 69.27(14) . . ?
C7 C8 Fe1 70.00(15) . . ?
C15 C16 C17 116.8(2) . . ?
C15 C16 C21 122.5(2) . . ?
C17 C16 C21 120.7(2) . . ?
C19 C18 C17 120.5(2) . . ?
C22 C21 C16 112.4(2) . . ?
C22 C21 C23 110.8(2) . . ?
C16 C21 C23 109.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lh2_127
_database_code_depnum_ccdc_archive 'CCDC 1022582'
_audit_update_record             
;
2014-09-02 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Au Cl Fe N3'
_chemical_formula_weight         617.70

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'
Au Au -2.0133 8.8022 '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                   24.435(5)
_cell_length_b                   7.515(5)
_cell_length_c                   11.492(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.546(5)
_cell_angle_gamma                90
_cell_volume                     2106.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3163
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.38

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    7.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20214
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         26.38
_reflns_number_total             4298
_reflns_number_gt                3163
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0141P)²+3.7607P] 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         4298
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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
Au1 Au 0.245046(7) -0.74965(3) 0.557862(14) 0.01418(6) Uani 1 1 d . . .
Fe1 Fe 0.09802(3) -0.54722(9) 0.39184(6) 0.01415(15) Uani 1 1 d . . .
Cl1 Cl 0.23123(5) -1.02719(15) 0.63242(10) 0.0245(3) Uani 1 1 d . . .
C9 C 0.13252(18) -0.4666(6) 0.5496(4) 0.0161(10) Uani 1 1 d . . .
H9 H 0.1501 -0.5388 0.6060 0.019 Uiso 1 1 calc R . .
N1 N 0.24643(15) -0.2624(5) 0.3865(3) 0.0141(8) Uani 1 1 d . . .
C16 C 0.3873(2) -0.4486(8) 0.5786(4) 0.0273(12) Uani 1 1 d . . .
C17 C 0.4374(2) -0.5296(8) 0.6097(4) 0.0334(14) Uani 1 1 d . . .
H17 H 0.4582 -0.4870 0.6743 0.040 Uiso 1 1 calc R . .
N5 N 0.30389(15) -0.4476(5) 0.4529(3) 0.0163(9) Uani 1 1 d . . .
N3 N 0.29992(16) -0.2949(5) 0.3930(3) 0.0148(9) Uani 1 1 d . . .
C23 C 0.3440(2) -0.7249(8) 0.3096(6) 0.0490(18) Uani 1 1 d . . .
H23A H 0.3634 -0.8203 0.2749 0.073 Uiso 1 1 calc R . .
H23B H 0.3386 -0.6296 0.2544 0.073 Uiso 1 1 calc R . .
H23C H 0.3090 -0.7673 0.3315 0.073 Uiso 1 1 calc R . .
C5 C 0.15803(18) -0.3781(6) 0.4560(4) 0.0125(10) Uani 1 1 d . . .
C7 C 0.0655(2) -0.3106(6) 0.4422(4) 0.0180(11) Uani 1 1 d . . .
H7 H 0.0317 -0.2629 0.4168 0.022 Uiso 1 1 calc R . .
C13 C 0.0513(2) -0.7701(7) 0.3648(5) 0.0288(13) Uani 1 1 d . . .
H13 H 0.0236 -0.8094 0.4106 0.035 Uiso 1 1 calc R . .
C33 C 0.2276(2) -0.1059(6) 0.3210(4) 0.0184(11) Uani 1 1 d . . .
H33A H 0.2583 -0.0307 0.3075 0.028 Uiso 1 1 calc R . .
H33B H 0.2018 -0.0416 0.3648 0.028 Uiso 1 1 calc R . .
H33C H 0.2101 -0.1422 0.2477 0.028 Uiso 1 1 calc R . .
C8 C 0.07566(19) -0.4244(6) 0.5409(4) 0.0180(11) Uani 1 1 d . . .
H8 H 0.0496 -0.4639 0.5907 0.022 Uiso 1 1 calc R . .
C20 C 0.3767(2) -0.6584(7) 0.4162(5) 0.0270(12) Uani 1 1 d . . .
C3 C 0.21672(18) -0.3878(6) 0.4410(4) 0.0114(10) Uani 1 1 d . . .
C15 C 0.35745(18) -0.5196(6) 0.4823(4) 0.0177(11) Uani 1 1 d . . .
C22 C 0.5114(2) -0.7584(8) 0.5875(6) 0.060(2) Uani 1 1 d . . .
H22A H 0.5269 -0.6984 0.6556 0.091 Uiso 1 1 calc R . .
H22B H 0.5363 -0.7504 0.5263 0.091 Uiso 1 1 calc R . .
H22C H 0.5053 -0.8812 0.6056 0.091 Uiso 1 1 calc R . .
C1 C 0.25452(18) -0.5125(6) 0.4843(4) 0.0138(10) Uani 1 1 d . . .
C12 C 0.1077(2) -0.8166(6) 0.3807(5) 0.0227(12) Uani 1 1 d . . .
H12 H 0.1235 -0.8911 0.4380 0.027 Uiso 1 1 calc R . .
C18 C 0.4572(2) -0.6712(8) 0.5478(5) 0.0355(15) Uani 1 1 d . . .
C21 C 0.3663(2) -0.2934(9) 0.6447(5) 0.0484(19) Uani 1 1 d . . .
H21A H 0.3921 -0.2638 0.7080 0.073 Uiso 1 1 calc R . .
H21B H 0.3317 -0.3240 0.6749 0.073 Uiso 1 1 calc R . .
H21C H 0.3614 -0.1930 0.5935 0.073 Uiso 1 1 calc R . .
C11 C 0.1353(2) -0.7275(6) 0.2921(4) 0.0217(11) Uani 1 1 d . . .
H11 H 0.1727 -0.7331 0.2816 0.026 Uiso 1 1 calc R . .
C6 C 0.11603(19) -0.2830(6) 0.3896(4) 0.0175(11) Uani 1 1 d . . .
H6 H 0.1209 -0.2150 0.3234 0.021 Uiso 1 1 calc R . .
C10 C 0.0962(2) -0.6289(7) 0.2228(4) 0.0267(13) Uani 1 1 d . . .
H10 H 0.1034 -0.5592 0.1587 0.032 Uiso 1 1 calc R . .
C19 C 0.4265(2) -0.7322(7) 0.4510(6) 0.0384(15) Uani 1 1 d . . .
H19 H 0.4400 -0.8257 0.4081 0.046 Uiso 1 1 calc R . .
C14 C 0.0442(2) -0.6548(8) 0.2683(5) 0.0314(14) Uani 1 1 d . . .
H14 H 0.0113 -0.6046 0.2396 0.038 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Au1 C1 1.992(5) . ?
Au1 Cl1 2.2878(17) . ?
Fe1 C11 2.026(5) . ?
Fe1 C6 2.034(4) . ?
Fe1 C10 2.035(5) . ?
Fe1 C13 2.041(5) . ?
Fe1 C14 2.042(5) . ?
Fe1 C12 2.043(5) . ?
Fe1 C9 2.043(4) . ?
Fe1 C5 2.043(4) . ?
Fe1 C7 2.046(5) . ?
Fe1 C8 2.050(4) . ?
C9 C8 1.422(6) . ?
C9 C5 1.439(6) . ?
N1 N3 1.327(5) . ?
N1 C3 1.365(5) . ?
N1 C33 1.455(5) . ?
C16 C17 1.393(7) . ?
C16 C15 1.394(6) . ?
C16 C21 1.500(7) . ?
C17 C18 1.384(8) . ?
N5 N3 1.339(5) . ?
N5 C1 1.370(5) . ?
N5 C15 1.437(6) . ?
C23 C20 1.507(8) . ?
C5 C6 1.431(6) . ?
C5 C3 1.457(6) . ?
C7 C6 1.423(6) . ?
C7 C8 1.430(6) . ?
C13 C14 1.410(8) . ?
C13 C12 1.422(7) . ?
C20 C19 1.375(7) . ?
C20 C15 1.389(7) . ?
C3 C1 1.387(6) . ?
C22 C18 1.523(8) . ?
C12 C11 1.423(7) . ?
C18 C19 1.380(8) . ?
C11 C10 1.415(7) . ?
C10 C14 1.417(7) . ?

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
C1 Au1 Cl1 176.56(13) . . ?
C11 Fe1 C6 122.69(19) . . ?
C11 Fe1 C10 40.78(19) . . ?
C6 Fe1 C10 105.9(2) . . ?
C11 Fe1 C13 68.40(19) . . ?
C6 Fe1 C13 156.8(2) . . ?
C10 Fe1 C13 68.2(2) . . ?
C11 Fe1 C14 68.6(2) . . ?
C6 Fe1 C14 120.5(2) . . ?
C10 Fe1 C14 40.7(2) . . ?
C13 Fe1 C14 40.4(2) . . ?
C11 Fe1 C12 40.93(18) . . ?
C6 Fe1 C12 160.13(19) . . ?
C10 Fe1 C12 68.7(2) . . ?
C13 Fe1 C12 40.77(19) . . ?
C14 Fe1 C12 68.6(2) . . ?
C11 Fe1 C9 121.7(2) . . ?
C6 Fe1 C9 69.16(19) . . ?
C10 Fe1 C9 156.91(19) . . ?
C13 Fe1 C9 125.1(2) . . ?
C14 Fe1 C9 161.3(2) . . ?
C12 Fe1 C9 107.9(2) . . ?
C11 Fe1 C5 106.40(18) . . ?
C6 Fe1 C5 41.10(17) . . ?
C10 Fe1 C5 120.33(19) . . ?
C13 Fe1 C5 161.5(2) . . ?
C14 Fe1 C5 156.1(2) . . ?
C12 Fe1 C5 123.79(19) . . ?
C9 Fe1 C5 41.24(16) . . ?
C11 Fe1 C7 159.55(19) . . ?
C6 Fe1 C7 40.83(18) . . ?
C10 Fe1 C7 123.1(2) . . ?
C13 Fe1 C7 122.2(2) . . ?
C14 Fe1 C7 107.2(2) . . ?
C12 Fe1 C7 158.02(19) . . ?
C9 Fe1 C7 68.74(19) . . ?
C5 Fe1 C7 68.89(19) . . ?
C11 Fe1 C8 157.8(2) . . ?
C6 Fe1 C8 68.92(19) . . ?
C10 Fe1 C8 160.4(2) . . ?
C13 Fe1 C8 108.7(2) . . ?
C14 Fe1 C8 124.5(2) . . ?
C12 Fe1 C8 122.43(19) . . ?
C9 Fe1 C8 40.67(17) . . ?
C5 Fe1 C8 68.95(18) . . ?
C7 Fe1 C8 40.88(18) . . ?
C8 C9 C5 108.1(4) . . ?
C8 C9 Fe1 69.9(3) . . ?
C5 C9 Fe1 69.4(2) . . ?
N3 N1 C3 113.4(4) . . ?
N3 N1 C33 117.2(3) . . ?
C3 N1 C33 129.4(4) . . ?
C17 C16 C15 116.4(5) . . ?
C17 C16 C21 122.2(5) . . ?
C15 C16 C21 121.4(5) . . ?
C18 C17 C16 122.2(5) . . ?
N3 N5 C1 113.8(4) . . ?
N3 N5 C15 118.7(4) . . ?
C1 N5 C15 127.5(4) . . ?
N1 N3 N5 103.1(3) . . ?
C6 C5 C9 107.4(4) . . ?
C6 C5 C3 129.8(4) . . ?
C9 C5 C3 122.7(4) . . ?
C6 C5 Fe1 69.1(3) . . ?
C9 C5 Fe1 69.4(2) . . ?
C3 C5 Fe1 128.0(3) . . ?
C6 C7 C8 108.2(4) . . ?
C6 C7 Fe1 69.2(3) . . ?
C8 C7 Fe1 69.7(3) . . ?
C14 C13 C12 108.8(5) . . ?
C14 C13 Fe1 69.8(3) . . ?
C12 C13 Fe1 69.7(3) . . ?
C9 C8 C7 108.0(4) . . ?
C9 C8 Fe1 69.4(3) . . ?
C7 C8 Fe1 69.4(3) . . ?
C19 C20 C15 117.9(5) . . ?
C19 C20 C23 121.2(5) . . ?
C15 C20 C23 120.9(5) . . ?
N1 C3 C1 105.7(4) . . ?
N1 C3 C5 125.1(4) . . ?
C1 C3 C5 129.1(4) . . ?
C20 C15 C16 122.9(5) . . ?
C20 C15 N5 119.3(4) . . ?
C16 C15 N5 117.8(4) . . ?
N5 C1 C3 104.1(4) . . ?
N5 C1 Au1 123.9(3) . . ?
C3 C1 Au1 131.7(3) . . ?
C13 C12 C11 106.9(5) . . ?
C13 C12 Fe1 69.5(3) . . ?
C11 C12 Fe1 68.9(3) . . ?
C19 C18 C17 118.7(5) . . ?
C19 C18 C22 121.1(6) . . ?
C17 C18 C22 120.2(6) . . ?
C10 C11 C12 108.4(4) . . ?
C10 C11 Fe1 69.9(3) . . ?
C12 C11 Fe1 70.2(3) . . ?
C7 C6 C5 108.2(4) . . ?
C7 C6 Fe1 70.0(3) . . ?
C5 C6 Fe1 69.8(2) . . ?
C11 C10 C14 108.1(5) . . ?
C11 C10 Fe1 69.3(3) . . ?
C14 C10 Fe1 69.9(3) . . ?
C20 C19 C18 121.8(6) . . ?
C13 C14 C10 107.8(5) . . ?
C13 C14 Fe1 69.8(3) . . ?
C10 C14 Fe1 69.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.862
_refine_diff_density_min         -1.188
_refine_diff_density_rms         0.138
