# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 Cl3 Fe N5 O'
_chemical_formula_sum            'C12 H13 Cl3 Fe N5 O'
_chemical_formula_weight         405.47

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           'orthorhombic '
_symmetry_space_group_name_H-M   'P ca21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   16.268(3)
_cell_length_b                   12.616(3)
_cell_length_c                   15.815(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3245.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    11061
_cell_measurement_theta_min      3.0380
_cell_measurement_theta_max      27.4894

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5350
_exptl_absorpt_correction_T_max  0.5986
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22301
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5222
_reflns_number_gt                4762
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
SIMU+- instruction was used to make the geometrical configurations and displacement parameters reasonable
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+7.7307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.69(3)
_refine_ls_number_reflns         5222
_refine_ls_number_parameters     399
_refine_ls_number_restraints     865
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.31843(6) 0.54044(8) 0.17125(7) 0.0267(3) Uani 1 1 d . . .
Fe2 Fe 0.43133(6) -0.04067(8) 0.35367(7) 0.0266(3) Uani 1 1 d . . .
Cl1 Cl 0.37161(13) 0.54524(14) 0.31426(13) 0.0401(5) Uani 1 1 d . . .
Cl2 Cl 0.26176(13) 0.50723(13) 0.03760(15) 0.0272(4) Uani 1 1 d . . .
Cl3 Cl 0.23723(14) 0.68170(17) 0.19551(15) 0.0515(6) Uani 1 1 d . . .
Cl4 Cl 0.48659(17) -0.01904(17) 0.49072(17) 0.0461(6) Uani 1 1 d . . .
Cl5 Cl 0.37896(13) -0.04189(15) 0.21048(13) 0.0394(5) Uani 1 1 d . . .
Cl6 Cl 0.51179(14) -0.18203(17) 0.32662(16) 0.0523(6) Uani 1 1 d . . .
O1 O 0.1798(4) 0.9664(5) 0.2316(4) 0.0466(16) Uani 1 1 d . . .
H1C H 0.2279 0.9453 0.2444 0.056 Uiso 1 1 d R . .
O2 O 0.0708(4) 0.4617(5) 0.2934(4) 0.0515(16) Uani 1 1 d . . .
H2C H 0.0186 0.4596 0.2907 0.062 Uiso 1 1 d R . .
N1 N 0.4379(4) 0.7342(5) 0.1201(5) 0.0340(14) Uani 1 1 d U . .
H1B H 0.4048 0.7848 0.1354 0.041 Uiso 1 1 calc R . .
N2 N 0.4206(4) 0.6311(5) 0.1286(4) 0.0319(12) Uani 1 1 d U . .
N3 N 0.4133(4) 0.4288(5) 0.1348(4) 0.0265(10) Uani 1 1 d U . .
N4 N 0.2710(4) 0.3861(5) 0.1996(4) 0.0306(11) Uani 1 1 d U . .
N5 N 0.1997(4) 0.3432(5) 0.2279(4) 0.0331(12) Uani 1 1 d U . .
H5B H 0.1590 0.3800 0.2482 0.040 Uiso 1 1 calc R . .
N6 N 0.5535(4) 0.1520(5) 0.2995(4) 0.0340(13) Uani 1 1 d U . .
H6B H 0.5948 0.1132 0.2834 0.041 Uiso 1 1 calc R . .
N7 N 0.4814(3) 0.1138(4) 0.3259(4) 0.0264(11) Uani 1 1 d U . .
N8 N 0.3377(4) 0.0738(5) 0.3891(4) 0.0260(10) Uani 1 1 d U . .
N9 N 0.3261(4) -0.1270(5) 0.3947(4) 0.0282(12) Uani 1 1 d U . .
N10 N 0.3088(4) -0.2337(5) 0.4020(5) 0.0358(14) Uani 1 1 d U . .
H10B H 0.3413 -0.2855 0.3878 0.043 Uiso 1 1 calc R . .
C1 C 0.5109(5) 0.7507(7) 0.0860(6) 0.0418(16) Uani 1 1 d U . .
H1A H 0.5346 0.8169 0.0741 0.050 Uiso 1 1 calc R . .
C2 C 0.5450(5) 0.6554(6) 0.0716(6) 0.0359(14) Uani 1 1 d U . .
H2A H 0.5967 0.6423 0.0473 0.043 Uiso 1 1 calc R . .
C3 C 0.4877(5) 0.5783(6) 0.1000(5) 0.0283(13) Uani 1 1 d U . .
C4 C 0.4847(5) 0.4622(6) 0.1025(5) 0.0283(12) Uani 1 1 d U . .
C5 C 0.5416(5) 0.3937(6) 0.0695(6) 0.0350(14) Uani 1 1 d U . .
H5A H 0.5901 0.4190 0.0443 0.042 Uiso 1 1 calc R . .
C6 C 0.5259(5) 0.2890(6) 0.0742(5) 0.0366(14) Uani 1 1 d U . .
H6A H 0.5648 0.2404 0.0537 0.044 Uiso 1 1 calc R . .
C7 C 0.4540(5) 0.2527(6) 0.1084(5) 0.0310(13) Uani 1 1 d U . .
H7 H 0.4428 0.1796 0.1101 0.037 Uiso 1 1 calc R . .
C8 C 0.3980(4) 0.3246(6) 0.1403(5) 0.0277(11) Uani 1 1 d U . .
C9 C 0.3174(4) 0.3010(5) 0.1760(5) 0.0270(11) Uani 1 1 d U . .
C10 C 0.2729(5) 0.2085(6) 0.1887(5) 0.0336(12) Uani 1 1 d U . .
H10A H 0.2902 0.1389 0.1772 0.040 Uiso 1 1 calc R . .
C11 C 0.1994(5) 0.2388(6) 0.2209(5) 0.0379(14) Uani 1 1 d U . .
H11A H 0.1558 0.1935 0.2356 0.046 Uiso 1 1 calc R . .
C12 C 0.5537(5) 0.2592(6) 0.3011(5) 0.0353(13) Uani 1 1 d U . .
H12A H 0.5967 0.3038 0.2833 0.042 Uiso 1 1 calc R . .
C13 C 0.4801(4) 0.2906(6) 0.3333(5) 0.0313(12) Uani 1 1 d U . .
H13A H 0.4623 0.3603 0.3431 0.038 Uiso 1 1 calc R . .
C14 C 0.4368(4) 0.1975(5) 0.3486(5) 0.0279(11) Uani 1 1 d U . .
C15 C 0.3549(4) 0.1776(6) 0.3842(5) 0.0286(11) Uani 1 1 d U . .
C16 C 0.3009(5) 0.2543(6) 0.4109(5) 0.0305(12) Uani 1 1 d U . .
H16A H 0.3145 0.3266 0.4071 0.037 Uiso 1 1 calc R . .
C17 C 0.2243(5) 0.2216(6) 0.4442(5) 0.0327(14) Uani 1 1 d U . .
H17A H 0.1856 0.2724 0.4617 0.039 Uiso 1 1 calc R . .
C18 C 0.2062(5) 0.1122(6) 0.4511(5) 0.0305(13) Uani 1 1 d U . .
H18A H 0.1555 0.0889 0.4727 0.037 Uiso 1 1 calc R . .
C19 C 0.2660(5) 0.0397(6) 0.4246(5) 0.0292(12) Uani 1 1 d U . .
C20 C 0.2605(5) -0.0745(6) 0.4257(5) 0.0300(13) Uani 1 1 d U . .
C21 C 0.1991(5) -0.1440(6) 0.4505(5) 0.0345(14) Uani 1 1 d U . .
H21A H 0.1471 -0.1273 0.4727 0.041 Uiso 1 1 calc R . .
C22 C 0.2315(5) -0.2436(6) 0.4355(6) 0.0373(16) Uani 1 1 d U . .
H22A H 0.2047 -0.3081 0.4465 0.045 Uiso 1 1 calc R . .
C23 C 0.1606(9) 0.9654(9) 0.1444(8) 0.077(4) Uani 1 1 d . . .
H23A H 0.2063 0.9943 0.1125 0.092 Uiso 1 1 calc R . .
H23C H 0.1119 1.0081 0.1345 0.092 Uiso 1 1 calc R . .
H23B H 0.1502 0.8931 0.1263 0.092 Uiso 1 1 calc R . .
C24 C 0.0912(7) 0.4667(9) 0.3791(7) 0.068(3) Uani 1 1 d U . .
H24A H 0.1504 0.4624 0.3854 0.101 Uiso 1 1 calc R . .
H24B H 0.0656 0.4081 0.4088 0.101 Uiso 1 1 calc R . .
H24C H 0.0717 0.5331 0.4026 0.101 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N2 2.127(6) . ?
Fe1 N4 2.141(6) . ?
Fe1 N3 2.167(6) . ?
Fe1 Cl3 2.251(2) . ?
Fe1 Cl2 2.344(3) . ?
Fe1 Cl1 2.422(2) . ?
Fe2 N9 2.131(6) . ?
Fe2 N7 2.157(6) . ?
Fe2 N8 2.172(6) . ?
Fe2 Cl6 2.253(2) . ?
Fe2 Cl4 2.362(3) . ?
Fe2 Cl5 2.420(2) . ?
O1 C23 1.414(14) . ?
O1 H1C 0.8501 . ?
O2 C24 1.398(13) . ?
O2 H2C 0.8500 . ?
N1 C1 1.319(11) . ?
N1 N2 1.337(9) . ?
N1 H1B 0.8700 . ?
N2 C3 1.357(9) . ?
N3 C4 1.337(10) . ?
N3 C8 1.342(9) . ?
N4 N5 1.357(8) . ?
N4 C9 1.364(9) . ?
N5 C11 1.322(10) . ?
N5 H5B 0.8700 . ?
N6 N7 1.335(8) . ?
N6 C12 1.353(9) . ?
N6 H6B 0.8700 . ?
N7 C14 1.330(9) . ?
N8 C15 1.342(9) . ?
N8 C19 1.364(10) . ?
N9 C20 1.348(10) . ?
N9 N10 1.379(9) . ?
N10 C22 1.370(10) . ?
N10 H10B 0.8700 . ?
C1 C2 1.343(11) . ?
C1 H1A 0.9400 . ?
C2 C3 1.420(10) . ?
C2 H2A 0.9400 . ?
C3 C4 1.467(10) . ?
C4 C5 1.370(11) . ?
C5 C6 1.347(11) . ?
C5 H5A 0.9400 . ?
C6 C7 1.368(11) . ?
C6 H6A 0.9400 . ?
C7 C8 1.380(11) . ?
C7 H7 0.9400 . ?
C8 C9 1.459(10) . ?
C9 C10 1.389(10) . ?
C10 C11 1.354(11) . ?
C10 H10A 0.9400 . ?
C11 H11A 0.9400 . ?
C12 C13 1.360(10) . ?
C12 H12A 0.9400 . ?
C13 C14 1.391(9) . ?
C13 H13A 0.9400 . ?
C14 C15 1.468(10) . ?
C15 C16 1.373(10) . ?
C16 C17 1.415(11) . ?
C16 H16A 0.9400 . ?
C17 C18 1.416(10) . ?
C17 H17A 0.9400 . ?
C18 C19 1.399(10) . ?
C18 H18A 0.9400 . ?
C19 C20 1.444(10) . ?
C20 C21 1.386(11) . ?
C21 C22 1.382(11) . ?
C21 H21A 0.9400 . ?
C22 H22A 0.9400 . ?
C23 H23A 0.9700 . ?
C23 H23C 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N4 146.8(2) . . ?
N2 Fe1 N3 73.1(2) . . ?
N4 Fe1 N3 73.8(2) . . ?
N2 Fe1 Cl3 94.97(19) . . ?
N4 Fe1 Cl3 118.22(18) . . ?
N3 Fe1 Cl3 167.82(18) . . ?
N2 Fe1 Cl2 96.8(2) . . ?
N4 Fe1 Cl2 83.39(17) . . ?
N3 Fe1 Cl2 85.63(18) . . ?
Cl3 Fe1 Cl2 93.69(9) . . ?
N2 Fe1 Cl1 90.2(2) . . ?
N4 Fe1 Cl1 87.46(17) . . ?
N3 Fe1 Cl1 90.61(18) . . ?
Cl3 Fe1 Cl1 91.75(9) . . ?
Cl2 Fe1 Cl1 170.76(8) . . ?
N9 Fe2 N7 145.8(2) . . ?
N9 Fe2 N8 72.4(2) . . ?
N7 Fe2 N8 73.6(2) . . ?
N9 Fe2 Cl6 96.90(19) . . ?
N7 Fe2 Cl6 117.18(17) . . ?
N8 Fe2 Cl6 169.24(18) . . ?
N9 Fe2 Cl4 94.89(19) . . ?
N7 Fe2 Cl4 86.48(17) . . ?
N8 Fe2 Cl4 87.30(18) . . ?
Cl6 Fe2 Cl4 92.55(9) . . ?
N9 Fe2 Cl5 89.95(19) . . ?
N7 Fe2 Cl5 87.04(17) . . ?
N8 Fe2 Cl5 89.96(17) . . ?
Cl6 Fe2 Cl5 91.25(9) . . ?
Cl4 Fe2 Cl5 173.45(9) . . ?
C23 O1 H1C 115.6 . . ?
C24 O2 H2C 106.7 . . ?
C1 N1 N2 112.6(7) . . ?
C1 N1 H1B 123.7 . . ?
N2 N1 H1B 123.7 . . ?
N1 N2 C3 105.9(6) . . ?
N1 N2 Fe1 136.1(5) . . ?
C3 N2 Fe1 118.1(5) . . ?
C4 N3 C8 119.6(6) . . ?
C4 N3 Fe1 121.1(5) . . ?
C8 N3 Fe1 119.2(5) . . ?
N5 N4 C9 104.4(6) . . ?
N5 N4 Fe1 137.7(5) . . ?
C9 N4 Fe1 117.3(4) . . ?
C11 N5 N4 111.9(7) . . ?
C11 N5 H5B 124.1 . . ?
N4 N5 H5B 124.1 . . ?
N7 N6 C12 111.0(6) . . ?
N7 N6 H6B 124.5 . . ?
C12 N6 H6B 124.5 . . ?
C14 N7 N6 106.1(6) . . ?
C14 N7 Fe2 117.1(4) . . ?
N6 N7 Fe2 136.2(5) . . ?
C15 N8 C19 120.6(6) . . ?
C15 N8 Fe2 119.2(5) . . ?
C19 N8 Fe2 119.8(5) . . ?
C20 N9 N10 106.7(6) . . ?
C20 N9 Fe2 119.7(5) . . ?
N10 N9 Fe2 133.4(5) . . ?
N9 N10 C22 107.9(7) . . ?
N9 N10 H10B 126.0 . . ?
C22 N10 H10B 126.0 . . ?
N1 C1 C2 107.4(7) . . ?
N1 C1 H1A 126.3 . . ?
C2 C1 H1A 126.3 . . ?
C1 C2 C3 106.7(7) . . ?
C1 C2 H2A 126.6 . . ?
C3 C2 H2A 126.6 . . ?
N2 C3 C2 107.3(7) . . ?
N2 C3 C4 117.0(6) . . ?
C2 C3 C4 135.6(7) . . ?
N3 C4 C5 122.3(7) . . ?
N3 C4 C3 110.7(6) . . ?
C5 C4 C3 126.7(7) . . ?
C6 C5 C4 118.0(8) . . ?
C6 C5 H5A 121.0 . . ?
C4 C5 H5A 121.0 . . ?
C5 C6 C7 120.8(8) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C6 C7 C8 119.2(8) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N3 C8 C7 119.9(7) . . ?
N3 C8 C9 113.0(6) . . ?
C7 C8 C9 126.9(7) . . ?
N4 C9 C10 109.5(6) . . ?
N4 C9 C8 116.3(6) . . ?
C10 C9 C8 134.1(7) . . ?
C11 C10 C9 106.1(7) . . ?
C11 C10 H10A 126.9 . . ?
C9 C10 H10A 126.9 . . ?
N5 C11 C10 108.1(7) . . ?
N5 C11 H11A 126.0 . . ?
C10 C11 H11A 126.0 . . ?
N6 C12 C13 107.2(7) . . ?
N6 C12 H12A 126.4 . . ?
C13 C12 H12A 126.4 . . ?
C12 C13 C14 105.4(7) . . ?
C12 C13 H13A 127.3 . . ?
C14 C13 H13A 127.3 . . ?
N7 C14 C13 110.3(6) . . ?
N7 C14 C15 117.6(6) . . ?
C13 C14 C15 132.1(6) . . ?
N8 C15 C16 122.5(7) . . ?
N8 C15 C14 112.2(6) . . ?
C16 C15 C14 125.4(7) . . ?
C15 C16 C17 118.2(7) . . ?
C15 C16 H16A 120.9 . . ?
C17 C16 H16A 120.9 . . ?
C18 C17 C16 119.7(7) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C19 C18 C17 118.0(7) . . ?
C19 C18 H18A 121.0 . . ?
C17 C18 H18A 121.0 . . ?
N8 C19 C18 120.8(7) . . ?
N8 C19 C20 111.9(6) . . ?
C18 C19 C20 127.3(7) . . ?
N9 C20 C21 111.2(6) . . ?
N9 C20 C19 115.9(6) . . ?
C21 C20 C19 132.9(7) . . ?
C22 C21 C20 104.6(7) . . ?
C22 C21 H21A 127.7 . . ?
C20 C21 H21A 127.7 . . ?
C21 C22 N10 109.5(7) . . ?
C21 C22 H22A 125.3 . . ?
N10 C22 H22A 125.3 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10B Cl1 0.87 2.48 3.279(7) 152.7 1_545
N6 H6B O1 0.87 1.90 2.758(9) 171.3 4_565
N5 H5B O2 0.87 1.91 2.775(9) 179.3 .
N1 H1B Cl5 0.87 2.52 3.309(7) 150.4 1_565
O2 H2C Cl1 0.85 2.42 3.258(7) 168.3 4_465
O1 H1C Cl5 0.85 2.52 3.258(6) 145.7 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.543
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 983047'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 Cl2 Fe N5 '
_chemical_formula_sum            'C11 H7 Cl2 Fe N5 '
_chemical_formula_weight         335.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc '


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                   10.221(2)
_cell_length_b                   17.195(3)
_cell_length_c                   7.9908(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.40(3)
_cell_angle_gamma                90.00
_cell_volume                     1360.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3259
_cell_measurement_theta_min      3.1420
_cell_measurement_theta_max      27.4584

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.9000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.1000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.64
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    1.492
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_process_details   
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku MercuryCCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3746
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1530
_reflns_number_gt                1276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_cell_refinement       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_data_reduction        
'CrystalStructure, Ver. 3.60 (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0131(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1530
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_restrained_S_all      0.897
_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 0.0000 0.12261(2) 0.2500 0.03134(19) Uani 1 2 d S . .
Cl1 Cl 0.18592(5) 0.05864(3) 0.19499(8) 0.0406(2) Uani 1 1 d . . .
N1 N -0.09075(17) 0.15710(11) -0.0169(2) 0.0317(4) Uani 1 1 d . . .
C1 C 0.0000 0.4054(2) 0.2500 0.0414(8) Uani 1 2 d S . .
H1 H 0.0000 0.4595 0.2500 0.050 Uiso 1 2 calc SR . .
N2 N -0.1385(2) 0.12302(11) -0.1716(2) 0.0354(4) Uani 1 1 d . . .
C2 C -0.0531(2) 0.36564(13) 0.0972(3) 0.0376(5) Uani 1 1 d . . .
H2 H -0.0890 0.3923 -0.0052 0.045 Uiso 1 1 calc R . .
C3 C -0.05109(19) 0.28504(12) 0.1016(3) 0.0293(4) Uani 1 1 d . . .
N3 N 0.0000 0.24625(14) 0.2500 0.0290(5) Uani 1 2 d S . .
C4 C -0.1012(2) 0.23384(12) -0.0466(3) 0.0287(4) Uani 1 1 d . . .
C5 C -0.1569(2) 0.24850(13) -0.2219(3) 0.0347(5) Uani 1 1 d . . .
H6 H -0.1750 0.2966 -0.2760 0.042 Uiso 1 1 calc R . .
C6 C -0.1791(2) 0.17668(14) -0.2963(3) 0.0384(5) Uani 1 1 d . . .
H7 H -0.2158 0.1666 -0.4129 0.046 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N3 2.126(2) . ?
Fe1 N1 2.1855(18) 2 ?
Fe1 N1 2.1855(18) . ?
Fe1 Cl1 2.3302(7) 2 ?
Fe1 Cl1 2.3302(7) . ?
N1 C4 1.340(3) . ?
N1 N2 1.345(2) . ?
C1 C2 1.387(3) . ?
C1 C2 1.387(3) 2 ?
C1 H1 0.9300 . ?
N2 C6 1.346(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 N3 1.347(2) . ?
C3 C4 1.462(3) . ?
N3 C3 1.347(2) 2 ?
C4 C5 1.398(3) . ?
C5 C6 1.365(3) . ?
C5 H6 0.9300 . ?
C6 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Fe1 N1 74.26(5) . 2 ?
N3 Fe1 N1 74.26(5) . . ?
N1 Fe1 N1 148.51(10) 2 . ?
N3 Fe1 Cl1 118.167(17) . 2 ?
N1 Fe1 Cl1 96.44(5) 2 2 ?
N1 Fe1 Cl1 98.28(5) . 2 ?
N3 Fe1 Cl1 118.167(17) . . ?
N1 Fe1 Cl1 98.28(5) 2 . ?
N1 Fe1 Cl1 96.44(5) . . ?
Cl1 Fe1 Cl1 123.67(3) 2 . ?
C4 N1 N2 105.76(17) . . ?
C4 N1 Fe1 115.82(14) . . ?
N2 N1 Fe1 138.37(15) . . ?
C2 C1 C2 120.9(3) . 2 ?
C2 C1 H1 119.6 . . ?
C2 C1 H1 119.6 2 . ?
N1 N2 C6 110.88(19) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
N3 C3 C2 121.1(2) . . ?
N3 C3 C4 113.30(19) . . ?
C2 C3 C4 125.6(2) . . ?
C3 N3 C3 120.7(3) 2 . ?
C3 N3 Fe1 119.67(13) 2 . ?
C3 N3 Fe1 119.67(13) . . ?
N1 C4 C5 110.46(19) . . ?
N1 C4 C3 116.94(18) . . ?
C5 C4 C3 132.6(2) . . ?
C6 C5 C4 104.8(2) . . ?
C6 C5 H6 127.6 . . ?
C4 C5 H6 127.6 . . ?
N2 C6 C5 108.1(2) . . ?
N2 C6 H7 125.9 . . ?
C5 C6 H7 125.9 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.152



#===END


_database_code_depnum_ccdc_archive 'CCDC 983048'
