# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_dttp

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H14 N), Cl6 Fe2 O'
_chemical_formula_sum            'C30 H28 Cl6 Fe2 N2 O'
_chemical_formula_weight         756.94

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'
Fe Fe 0.3480 0.8500 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.588(2)
_cell_length_b                   11.729(2)
_cell_length_c                   26.020(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.42(3)
_cell_angle_gamma                90
_cell_volume                     3230.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30010
_cell_measurement_theta_min      1.566
_cell_measurement_theta_max      27.918

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.422
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7108
_diffrn_radiation_type           synchrotron
_diffrn_source                   
;
MX1 Beamline Australian Synchrotron                       
;
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30010
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         27.918
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             7370
_reflns_number_gt                6290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0480P)²+3.5956P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7370
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.28460(3) 0.70169(3) 0.44052(2) 0.01727(9) Uani 1 1 d . . . . .
Cl1 Cl 0.32430(6) 0.88063(5) 0.46718(2) 0.02562(13) Uani 1 1 d . . . . .
O1 O 0.22856(18) 0.69812(17) 0.37600(6) 0.0277(4) Uani 1 1 d . . . . .
N1 N 0.86768(19) 0.61295(17) 0.20503(7) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.9351(2) 0.5945(2) 0.24670(9) 0.0199(4) Uani 1 1 d . . . . .
H1 H 1.0245 0.5926 0.2447 0.024 Uiso 1 1 calc R U . . .
Fe2 Fe 0.25858(3) 0.72964(3) 0.31099(2) 0.01899(9) Uani 1 1 d . . . . .
Cl2 Cl 0.14026(6) 0.62242(5) 0.49020(2) 0.02217(12) Uani 1 1 d . . . . .
N2 N 0.70896(19) 0.76334(17) 0.50167(7) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.8785(2) 0.5770(2) 0.29576(8) 0.0203(5) Uani 1 1 d . . . . .
Cl3 Cl 0.46145(6) 0.60256(5) 0.44775(2) 0.02515(13) Uani 1 1 d . . . . .
C3 C 0.9525(3) 0.5316(2) 0.33644(9) 0.0238(5) Uani 1 1 d . . . . .
H3 H 1.0404 0.5191 0.3327 0.029 Uiso 1 1 calc R U . . .
Cl4 Cl 0.09636(6) 0.82791(5) 0.27697(2) 0.02207(12) Uani 1 1 d . . . . .
C4 C 0.8948(3) 0.5054(2) 0.38202(9) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.9426 0.4730 0.4097 0.031 Uiso 1 1 calc R U . . .
Cl5 Cl 0.27976(6) 0.57274(6) 0.26302(2) 0.02799(14) Uani 1 1 d . . . . .
C5 C 0.7666(3) 0.5267(2) 0.38725(9) 0.0271(5) Uani 1 1 d . . . . .
H5 H 0.7275 0.5073 0.4185 0.033 Uiso 1 1 calc R U . . .
Cl6 Cl 0.43144(6) 0.83482(6) 0.30747(2) 0.03032(14) Uani 1 1 d . . . . .
C6 C 0.6943(3) 0.5758(2) 0.34780(9) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.6074 0.5921 0.3525 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7507(2) 0.6009(2) 0.30124(9) 0.0229(5) Uani 1 1 d . . . . .
C8 C 0.6812(3) 0.6560(3) 0.25669(9) 0.0291(6) Uani 1 1 d . . . . .
H8A H 0.6948 0.7395 0.2577 0.035 Uiso 1 1 calc R U . . .
H8B H 0.5895 0.6414 0.2592 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7281(2) 0.6085(2) 0.20652(9) 0.0230(5) Uani 1 1 d . . . . .
H9A H 0.6997 0.5285 0.2026 0.028 Uiso 1 1 calc R U . . .
H9B H 0.6916 0.6531 0.1775 0.028 Uiso 1 1 calc R U . . .
C10 C 0.9266(2) 0.6225(2) 0.15550(8) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.8735(2) 0.5624(2) 0.11422(9) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.7994 0.5179 0.1182 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9319(2) 0.5694(2) 0.06682(9) 0.0222(5) Uani 1 1 d . . . . .
H12 H 0.8976 0.5289 0.0381 0.027 Uiso 1 1 calc R U . . .
C13 C 1.0398(2) 0.6352(2) 0.06138(9) 0.0231(5) Uani 1 1 d . . . . .
H13 H 1.0793 0.6391 0.0290 0.028 Uiso 1 1 calc R U . . .
C14 C 1.0903(3) 0.6952(2) 0.10303(9) 0.0246(5) Uani 1 1 d . . . . .
H14 H 1.1637 0.7406 0.0990 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0339(2) 0.6892(2) 0.15058(9) 0.0224(5) Uani 1 1 d . . . . .
H15 H 1.0682 0.7300 0.1792 0.027 Uiso 1 1 calc R U . . .
C16 C 0.6277(2) 0.8195(2) 0.52809(9) 0.0201(5) Uani 1 1 d . . . . .
H16 H 0.5996 0.8917 0.5158 0.024 Uiso 1 1 calc R U . . .
C17 C 0.5781(2) 0.7766(2) 0.57557(9) 0.0211(5) Uani 1 1 d . . . . .
C18 C 0.4741(3) 0.8301(2) 0.59728(9) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.4365 0.8946 0.5810 0.032 Uiso 1 1 calc R U . . .
C19 C 0.4262(3) 0.7883(3) 0.64279(10) 0.0305(6) Uani 1 1 d . . . . .
H19 H 0.3557 0.8241 0.6579 0.037 Uiso 1 1 calc R U . . .
C20 C 0.4824(3) 0.6937(3) 0.66600(10) 0.0314(6) Uani 1 1 d . . . . .
H20 H 0.4480 0.6637 0.6966 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5877(3) 0.6422(2) 0.64533(9) 0.0292(6) Uani 1 1 d . . . . .
H21 H 0.6258 0.5785 0.6621 0.035 Uiso 1 1 calc R U . . .
C22 C 0.6377(3) 0.6838(2) 0.59993(9) 0.0227(5) Uani 1 1 d . . . . .
C23 C 0.7572(3) 0.6402(2) 0.57710(9) 0.0243(5) Uani 1 1 d . . . . .
H23A H 0.7709 0.5599 0.5876 0.029 Uiso 1 1 calc R U . . .
H23B H 0.8298 0.6857 0.5902 0.029 Uiso 1 1 calc R U . . .
C24 C 0.7498(2) 0.6476(2) 0.51900(9) 0.0220(5) Uani 1 1 d . . . . .
H24A H 0.8336 0.6302 0.5049 0.026 Uiso 1 1 calc R U . . .
H24B H 0.6890 0.5901 0.5055 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7507(2) 0.8049(2) 0.45254(8) 0.0191(4) Uani 1 1 d . . . . .
C26 C 0.8754(2) 0.7881(2) 0.43917(9) 0.0223(5) Uani 1 1 d . . . . .
H26 H 0.9327 0.7503 0.4620 0.027 Uiso 1 1 calc R U . . .
C27 C 0.9154(2) 0.8275(2) 0.39175(9) 0.0238(5) Uani 1 1 d . . . . .
H27 H 1.0001 0.8152 0.3819 0.029 Uiso 1 1 calc R U . . .
C28 C 0.8321(3) 0.8845(2) 0.35898(9) 0.0249(5) Uani 1 1 d . . . . .
H28 H 0.8601 0.9126 0.3270 0.030 Uiso 1 1 calc R U . . .
C29 C 0.7082(2) 0.9006(2) 0.37273(9) 0.0235(5) Uani 1 1 d . . . . .
H29 H 0.6515 0.9398 0.3500 0.028 Uiso 1 1 calc R U . . .
C30 C 0.6654(2) 0.8601(2) 0.41947(9) 0.0206(5) Uani 1 1 d . . . . .
H30 H 0.5798 0.8699 0.4286 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.7673(17) . ?
Fe1 Cl3 2.2082(8) . ?
Fe1 Cl2 2.2290(8) . ?
Fe1 Cl1 2.2468(8) . ?
O1 Fe2 1.7680(17) . ?
N1 C1 1.302(3) . ?
N1 C10 1.450(3) . ?
N1 C9 1.480(3) . ?
C1 C2 1.438(3) . ?
Fe2 Cl6 2.2109(8) . ?
Fe2 Cl4 2.2332(8) . ?
Fe2 Cl5 2.2380(8) . ?
N2 C16 1.295(3) . ?
N2 C25 1.448(3) . ?
N2 C24 1.491(3) . ?
C2 C7 1.393(4) . ?
C2 C3 1.406(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.390(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.395(3) . ?
C7 C8 1.503(3) . ?
C8 C9 1.515(3) . ?
C10 C15 1.388(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.389(4) . ?
C13 C14 1.388(3) . ?
C14 C15 1.389(3) . ?
C16 C17 1.445(3) . ?
C17 C18 1.398(4) . ?
C17 C22 1.403(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.395(3) . ?
C22 C23 1.500(4) . ?
C23 C24 1.514(3) . ?
C25 C26 1.388(4) . ?
C25 C30 1.391(3) . ?
C26 C27 1.393(3) . ?
C27 C28 1.384(4) . ?
C28 C29 1.381(4) . ?
C29 C30 1.392(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
O1 Fe1 Cl3 109.42(7) . . ?
O1 Fe1 Cl2 108.79(7) . . ?
Cl3 Fe1 Cl2 108.85(3) . . ?
O1 Fe1 Cl1 111.79(7) . . ?
Cl3 Fe1 Cl1 108.29(3) . . ?
Cl2 Fe1 Cl1 109.66(3) . . ?
Fe1 O1 Fe2 147.13(12) . . ?
C1 N1 C10 120.9(2) . . ?
C1 N1 C9 120.0(2) . . ?
C10 N1 C9 118.55(19) . . ?
N1 C1 C2 122.1(2) . . ?
O1 Fe2 Cl6 108.96(7) . . ?
O1 Fe2 Cl4 109.42(7) . . ?
Cl6 Fe2 Cl4 108.96(3) . . ?
O1 Fe2 Cl5 112.61(7) . . ?
Cl6 Fe2 Cl5 109.95(3) . . ?
Cl4 Fe2 Cl5 106.86(3) . . ?
C16 N2 C25 121.2(2) . . ?
C16 N2 C24 119.6(2) . . ?
C25 N2 C24 118.79(19) . . ?
C7 C2 C3 121.6(2) . . ?
C7 C2 C1 119.3(2) . . ?
C3 C2 C1 119.0(2) . . ?
C4 C3 C2 118.7(2) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 C6 121.6(2) . . ?
C5 C6 C7 119.2(3) . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 C8 117.8(2) . . ?
C6 C7 C8 123.3(2) . . ?
C7 C8 C9 110.0(2) . . ?
N1 C9 C8 111.0(2) . . ?
C15 C10 C11 122.0(2) . . ?
C15 C10 N1 119.8(2) . . ?
C11 C10 N1 118.2(2) . . ?
C10 C11 C12 118.3(2) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 120.3(2) . . ?
C10 C15 C14 118.8(2) . . ?
N2 C16 C17 122.5(2) . . ?
C18 C17 C22 121.1(2) . . ?
C18 C17 C16 119.7(2) . . ?
C22 C17 C16 119.2(2) . . ?
C19 C18 C17 119.6(3) . . ?
C18 C19 C20 119.4(3) . . ?
C21 C20 C19 121.2(2) . . ?
C20 C21 C22 120.1(3) . . ?
C21 C22 C17 118.6(2) . . ?
C21 C22 C23 123.9(2) . . ?
C17 C22 C23 117.4(2) . . ?
C22 C23 C24 110.6(2) . . ?
N2 C24 C23 111.23(19) . . ?
C26 C25 C30 121.2(2) . . ?
C26 C25 N2 119.1(2) . . ?
C30 C25 N2 119.7(2) . . ?
C25 C26 C27 119.1(2) . . ?
C28 C27 C26 120.2(2) . . ?
C29 C28 C27 120.1(2) . . ?
C28 C29 C30 120.7(2) . . ?
C25 C30 C29 118.6(2) . . ?

_refine_diff_density_max         0.621
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-2


# start Validation Reply Form
_vrf_PLAT029_dttp                
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.958 Note  
RESPONSE: Limited by single axis on diffractometer
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 1027557'
