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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_liu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H19 N4 O2'
_chemical_formula_sum            'C29 H19 N4 O2'
_chemical_formula_weight         455.48

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P21212

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

_cell_length_a                   12.309(3)
_cell_length_b                   23.558(5)
_cell_length_c                   7.8737(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2283.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4509
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            14354
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.05
_reflns_number_total             4509
_reflns_number_gt                3483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0392P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(15)
_refine_ls_number_reflns         4509
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C1 C 1.2451(2) 0.53996(12) 0.1191(4) 0.0490(7) Uani 1 1 d . . .
H1 H 1.2341 0.5776 0.0883 0.059 Uiso 1 1 calc R . .
C2 C 1.3273(2) 0.50957(13) 0.0459(4) 0.0550(8) Uani 1 1 d . . .
H2 H 1.3728 0.5267 -0.0334 0.066 Uiso 1 1 calc R . .
C3 C 1.3427(2) 0.45384(14) 0.0896(4) 0.0543(8) Uani 1 1 d . . .
H3 H 1.3988 0.4332 0.0403 0.065 Uiso 1 1 calc R . .
C4 C 1.2752(2) 0.42834(11) 0.2066(3) 0.0441(7) Uani 1 1 d . . .
H4 H 1.2854 0.3903 0.2339 0.053 Uiso 1 1 calc R . .
C5 C 1.19285(18) 0.45838(9) 0.2837(3) 0.0320(6) Uani 1 1 d . . .
C6 C 1.1778(2) 0.51488(10) 0.2392(3) 0.0399(6) Uani 1 1 d . . .
H6 H 1.1227 0.5359 0.2898 0.048 Uiso 1 1 calc R . .
C11 C 0.68761(18) 0.33177(9) 0.8841(3) 0.0327(6) Uani 1 1 d . . .
H11 H 0.6896 0.3674 0.8334 0.039 Uiso 1 1 calc R . .
C12 C 0.76703(17) 0.29239(9) 0.8494(3) 0.0285(5) Uani 1 1 d . . .
C13 C 0.7638(2) 0.23908(10) 0.9212(4) 0.0424(7) Uani 1 1 d . . .
H13 H 0.8180 0.2127 0.8975 0.051 Uiso 1 1 calc R . .
C14 C 0.6798(2) 0.22528(11) 1.0281(4) 0.0484(7) Uani 1 1 d . . .
H14 H 0.6757 0.1890 1.0738 0.058 Uiso 1 1 calc R . .
C15 C 0.6016(2) 0.26495(11) 1.0679(4) 0.0460(7) Uani 1 1 d . . .
H15 H 0.5465 0.2559 1.1441 0.055 Uiso 1 1 calc R . .
C16 C 0.6052(2) 0.31801(11) 0.9947(3) 0.0419(7) Uani 1 1 d . . .
H16 H 0.5517 0.3446 1.0201 0.050 Uiso 1 1 calc R . .
C21 C 0.98141(18) 0.19117(9) 0.4130(3) 0.0314(5) Uani 1 1 d . . .
C22 C 1.0478(2) 0.15637(10) 0.5119(3) 0.0400(6) Uani 1 1 d . . .
H22 H 1.1065 0.1718 0.5701 0.048 Uiso 1 1 calc R . .
C23 C 1.0261(2) 0.09897(11) 0.5233(4) 0.0566(8) Uani 1 1 d . . .
H23 H 1.0704 0.0759 0.5894 0.068 Uiso 1 1 calc R . .
C24 C 0.9395(2) 0.07572(11) 0.4375(4) 0.0571(8) Uani 1 1 d . . .
H24 H 0.9254 0.0370 0.4455 0.069 Uiso 1 1 calc R . .
C25 C 0.8739(2) 0.10979(11) 0.3401(4) 0.0510(8) Uani 1 1 d . . .
H25 H 0.8157 0.0941 0.2812 0.061 Uiso 1 1 calc R . .
C26 C 0.8941(2) 0.16715(10) 0.3295(3) 0.0400(6) Uani 1 1 d . . .
H26 H 0.8483 0.1901 0.2653 0.048 Uiso 1 1 calc R . .
C27 C 1.01092(19) 0.25216(9) 0.3913(3) 0.0298(5) Uani 1 1 d . . .
C31 C 1.12416(18) 0.43037(8) 0.4163(3) 0.0292(5) Uani 1 1 d . . .
C32 C 1.06837(17) 0.38075(9) 0.3803(3) 0.0285(5) Uani 1 1 d . . .
H32 H 1.0719 0.3651 0.2720 0.034 Uiso 1 1 calc R . .
C33 C 1.00741(18) 0.35444(9) 0.5051(3) 0.0270(5) Uani 1 1 d . . .
C34 C 1.00244(18) 0.37507(9) 0.6709(3) 0.0246(5) Uani 1 1 d . . .
C35 C 1.06484(18) 0.42417(9) 0.7147(3) 0.0279(5) Uani 1 1 d . . .
C36 C 1.12046(17) 0.45222(8) 0.5812(3) 0.0287(5) Uani 1 1 d . . .
C37 C 1.17903(19) 0.50310(10) 0.6247(3) 0.0326(6) Uani 1 1 d . . .
N38 N 1.07136(18) 0.44334(9) 0.8754(3) 0.0401(5) Uani 1 1 d . . .
N39 N 1.22282(17) 0.54334(9) 0.6667(3) 0.0460(6) Uani 1 1 d . . .
C41 C 0.94777(18) 0.30132(9) 0.4659(3) 0.0267(5) Uani 1 1 d . . .
C42 C 0.85013(18) 0.28826(9) 0.5707(3) 0.0280(5) Uani 1 1 d . . .
C44 C 0.93497(18) 0.34643(8) 0.7991(3) 0.0274(5) Uani 1 1 d . . .
N43 N 0.85538(14) 0.30787(7) 0.7364(2) 0.0281(4) Uani 1 1 d . . .
N45 N 0.94572(17) 0.35721(8) 0.9576(3) 0.0341(5) Uani 1 1 d . . .
O46 O 0.93907(13) 0.28644(6) 0.2911(2) 0.0337(4) Uani 1 1 d . . .
O47 O 0.77369(12) 0.26078(7) 0.5193(2) 0.0391(4) Uani 1 1 d . . .
H45 H 0.8982(18) 0.3336(9) 1.021(3) 0.034(7) Uiso 1 1 d . . .
H38A H 1.023(3) 0.4218(13) 0.957(4) 0.094(11) Uiso 1 1 d . . .
H38B H 1.1074(18) 0.4746(9) 0.902(3) 0.037(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.368(4) . ?
C1 C6 1.389(3) . ?
C2 C3 1.370(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.377(3) . ?
C5 C6 1.389(3) . ?
C5 C31 1.497(3) . ?
C11 C12 1.375(3) . ?
C11 C16 1.376(3) . ?
C12 C13 1.378(3) . ?
C12 N43 1.451(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.378(4) . ?
C15 C16 1.377(3) . ?
C21 C26 1.381(3) . ?
C21 C22 1.395(3) . ?
C21 C27 1.492(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.376(4) . ?
C24 C25 1.372(4) . ?
C25 C26 1.376(3) . ?
C27 O46 1.434(3) . ?
C27 C41 1.513(3) . ?
C31 C32 1.385(3) . ?
C31 C36 1.397(3) . ?
C32 C33 1.383(3) . ?
C33 C34 1.394(3) . ?
C33 C41 1.483(3) . ?
C34 C35 1.431(3) . ?
C34 C44 1.471(3) . ?
C35 N38 1.346(3) . ?
C35 C36 1.418(3) . ?
C36 C37 1.440(3) . ?
C37 N39 1.140(3) . ?
C41 O46 1.425(3) . ?
C41 C42 1.490(3) . ?
C42 O47 1.211(2) . ?
C42 N43 1.386(3) . ?
C44 N45 1.281(3) . ?
C44 N43 1.424(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
C2 C1 C6 120.4(2) . . ?
C1 C2 C3 119.8(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 120.9(2) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 C31 119.8(2) . . ?
C6 C5 C31 121.5(2) . . ?
C5 C6 C1 120.0(3) . . ?
C12 C11 C16 119.4(2) . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 N43 119.02(19) . . ?
C13 C12 N43 120.1(2) . . ?
C14 C13 C12 119.3(2) . . ?
C13 C14 C15 120.4(2) . . ?
C16 C15 C14 119.9(2) . . ?
C11 C16 C15 120.1(2) . . ?
C26 C21 C22 118.7(2) . . ?
C26 C21 C27 122.0(2) . . ?
C22 C21 C27 119.2(2) . . ?
C23 C22 C21 119.9(3) . . ?
C24 C23 C22 120.5(3) . . ?
C25 C24 C23 119.8(2) . . ?
C24 C25 C26 120.1(3) . . ?
C25 C26 C21 120.9(3) . . ?
O46 C27 C21 117.07(18) . . ?
O46 C27 C41 57.72(13) . . ?
C21 C27 C41 124.6(2) . . ?
C32 C31 C36 119.0(2) . . ?
C32 C31 C5 120.6(2) . . ?
C36 C31 C5 120.28(19) . . ?
C33 C32 C31 120.1(2) . . ?
C32 C33 C34 122.2(2) . . ?
C32 C33 C41 119.9(2) . . ?
C34 C33 C41 117.9(2) . . ?
C33 C34 C35 118.9(2) . . ?
C33 C34 C44 120.5(2) . . ?
C35 C34 C44 120.6(2) . . ?
N38 C35 C36 120.8(2) . . ?
N38 C35 C34 122.0(2) . . ?
C36 C35 C34 117.2(2) . . ?
C31 C36 C35 122.19(19) . . ?
C31 C36 C37 120.7(2) . . ?
C35 C36 C37 117.0(2) . . ?
N39 C37 C36 176.6(3) . . ?
O46 C41 C33 116.49(18) . . ?
O46 C41 C42 115.06(18) . . ?
C33 C41 C42 117.27(19) . . ?
O46 C41 C27 58.36(13) . . ?
C33 C41 C27 118.17(19) . . ?
C42 C41 C27 118.10(17) . . ?
O47 C42 N43 121.9(2) . . ?
O47 C42 C41 123.5(2) . . ?
N43 C42 C41 114.51(19) . . ?
N45 C44 N43 122.3(2) . . ?
N45 C44 C34 121.3(2) . . ?
N43 C44 C34 116.32(19) . . ?
C42 N43 C44 124.80(19) . . ?
C42 N43 C12 117.27(17) . . ?
C44 N43 C12 117.62(18) . . ?
C41 O46 C27 63.92(14) . . ?

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
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 C31 -177.1(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C31 C5 C6 C1 178.1(2) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C16 C11 C12 N43 -178.2(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
N43 C12 C13 C14 179.8(2) . . . . ?
C12 C13 C14 C15 -2.3(4) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C26 C21 C22 C23 0.7(4) . . . . ?
C27 C21 C22 C23 -175.3(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C24 C25 C26 C21 1.4(4) . . . . ?
C22 C21 C26 C25 -1.4(4) . . . . ?
C27 C21 C26 C25 174.4(2) . . . . ?
C26 C21 C27 O46 5.3(3) . . . . ?
C22 C21 C27 O46 -178.9(2) . . . . ?
C26 C21 C27 C41 73.2(3) . . . . ?
C22 C21 C27 C41 -111.0(3) . . . . ?
C4 C5 C31 C32 -56.5(3) . . . . ?
C6 C5 C31 C32 125.4(2) . . . . ?
C4 C5 C31 C36 119.8(2) . . . . ?
C6 C5 C31 C36 -58.3(3) . . . . ?
C36 C31 C32 C33 2.0(3) . . . . ?
C5 C31 C32 C33 178.3(2) . . . . ?
C31 C32 C33 C34 -2.3(3) . . . . ?
C31 C32 C33 C41 179.97(19) . . . . ?
C32 C33 C34 C35 -1.8(3) . . . . ?
C41 C33 C34 C35 176.03(18) . . . . ?
C32 C33 C34 C44 178.8(2) . . . . ?
C41 C33 C34 C44 -3.3(3) . . . . ?
C33 C34 C35 N38 -174.0(2) . . . . ?
C44 C34 C35 N38 5.3(3) . . . . ?
C33 C34 C35 C36 5.8(3) . . . . ?
C44 C34 C35 C36 -174.77(19) . . . . ?
C32 C31 C36 C35 2.4(3) . . . . ?
C5 C31 C36 C35 -173.95(19) . . . . ?
C32 C31 C36 C37 178.8(2) . . . . ?
C5 C31 C36 C37 2.4(3) . . . . ?
N38 C35 C36 C31 173.6(2) . . . . ?
C34 C35 C36 C31 -6.3(3) . . . . ?
N38 C35 C36 C37 -2.9(3) . . . . ?
C34 C35 C36 C37 177.21(19) . . . . ?
C31 C36 C37 N39 171(4) . . . . ?
C35 C36 C37 N39 -12(4) . . . . ?
C32 C33 C41 O46 -12.3(3) . . . . ?
C34 C33 C41 O46 169.81(19) . . . . ?
C32 C33 C41 C42 -154.5(2) . . . . ?
C34 C33 C41 C42 27.7(3) . . . . ?
C32 C33 C41 C27 54.2(3) . . . . ?
C34 C33 C41 C27 -123.6(2) . . . . ?
C21 C27 C41 O46 -102.6(2) . . . . ?
O46 C27 C41 C33 -105.3(2) . . . . ?
C21 C27 C41 C33 152.1(2) . . . . ?
O46 C27 C41 C42 103.6(2) . . . . ?
C21 C27 C41 C42 1.0(3) . . . . ?
O46 C41 C42 O47 8.9(3) . . . . ?
C33 C41 C42 O47 151.6(2) . . . . ?
C27 C41 C42 O47 -57.1(3) . . . . ?
O46 C41 C42 N43 -174.03(17) . . . . ?
C33 C41 C42 N43 -31.4(3) . . . . ?
C27 C41 C42 N43 120.0(2) . . . . ?
C33 C34 C44 N45 165.7(2) . . . . ?
C35 C34 C44 N45 -13.7(3) . . . . ?
C33 C34 C44 N43 -16.3(3) . . . . ?
C35 C34 C44 N43 164.31(18) . . . . ?
O47 C42 N43 C44 -171.25(19) . . . . ?
C41 C42 N43 C44 11.6(3) . . . . ?
O47 C42 N43 C12 2.3(3) . . . . ?
C41 C42 N43 C12 -174.88(17) . . . . ?
N45 C44 N43 C42 -170.1(2) . . . . ?
C34 C44 N43 C42 12.0(3) . . . . ?
N45 C44 N43 C12 16.4(3) . . . . ?
C34 C44 N43 C12 -161.51(18) . . . . ?
C11 C12 N43 C42 -101.7(2) . . . . ?
C13 C12 N43 C42 78.8(3) . . . . ?
C11 C12 N43 C44 72.3(3) . . . . ?
C13 C12 N43 C44 -107.2(2) . . . . ?
C33 C41 O46 C27 108.2(2) . . . . ?
C42 C41 O46 C27 -108.8(2) . . . . ?
C21 C27 O46 C41 115.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 965575'
#######################################################################
#
#                 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_liu2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   14.1047(17)
_cell_length_b                   15.5305(18)
_cell_length_c                   7.6769(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.180(2)
_cell_angle_gamma                90.00
_cell_volume                     1664.5(3)
_cell_formula_units_Z            7
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             686
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10728
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         28.40
_reflns_number_total             4134
_reflns_number_gt                2981
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.1494P)²+0.3610P] 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       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4134
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2418
_refine_ls_wR_factor_gt          0.2200
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C2 C 0.97931(15) 0.11957(13) 0.2412(3) 0.0421(5) Uani 1 1 d . . .
C3 C 0.90394(14) 0.26046(13) 0.2206(3) 0.0384(5) Uani 1 1 d . . .
H3 H 0.9073 0.3193 0.2002 0.046 Uiso 1 1 calc R . .
C4 C 0.73597(14) 0.27938(12) 0.2717(3) 0.0372(4) Uani 1 1 d . . .
C5 C 0.81987(14) 0.22265(12) 0.2617(3) 0.0367(4) Uani 1 1 d . . .
C6 C 0.89688(16) 0.07844(13) 0.2797(3) 0.0429(5) Uani 1 1 d . . .
C7 C 0.81724(15) 0.13305(13) 0.2919(3) 0.0397(5) Uani 1 1 d . . .
C8 C 0.74988(15) 0.35791(13) 0.3580(3) 0.0407(5) Uani 1 1 d . . .
H8 H 0.8109 0.3730 0.4119 0.049 Uiso 1 1 calc R . .
C9 C 0.98192(14) 0.20748(12) 0.2113(3) 0.0389(5) Uani 1 1 d . . .
C10 C 0.64421(16) 0.25752(15) 0.1915(3) 0.0457(5) Uani 1 1 d . . .
H10 H 0.6337 0.2052 0.1330 0.055 Uiso 1 1 calc R . .
C11 C 0.67421(17) 0.41408(14) 0.3648(3) 0.0480(5) Uani 1 1 d . . .
H11 H 0.6845 0.4665 0.4230 0.058 Uiso 1 1 calc R . .
C12 C 1.13183(14) 0.15384(12) 0.1913(3) 0.0373(4) Uani 1 1 d . . .
C13 C 1.07977(15) 0.23053(13) 0.1747(3) 0.0417(5) Uani 1 1 d . . .
C15 C 1.07437(16) 0.08364(14) 0.2316(3) 0.0482(5) Uani 1 1 d . . .
C17 C 1.23097(15) 0.14641(14) 0.1788(3) 0.0464(5) Uani 1 1 d . . .
C19 C 0.58271(16) 0.39186(15) 0.2845(3) 0.0514(6) Uani 1 1 d . . .
H19 H 0.5316 0.4293 0.2885 0.062 Uiso 1 1 calc R . .
C21 C 0.56847(16) 0.31382(15) 0.1990(3) 0.0520(6) Uani 1 1 d . . .
H21 H 0.5074 0.2987 0.1457 0.062 Uiso 1 1 calc R . .
C22 C 1.26300(19) 0.15924(16) 0.0187(4) 0.0601(7) Uani 1 1 d . . .
H22 H 1.2200 0.1740 -0.0801 0.072 Uiso 1 1 calc R . .
C23 C 1.2947(2) 0.12460(17) 0.3265(4) 0.0633(7) Uani 1 1 d . . .
H23 H 1.2735 0.1174 0.4348 0.076 Uiso 1 1 calc R . .
C24 C 1.3599(2) 0.1499(2) 0.0064(5) 0.0817(10) Uani 1 1 d . . .
H24 H 1.3820 0.1593 -0.1004 0.098 Uiso 1 1 calc R . .
C25 C 1.4229(2) 0.12670(18) 0.1524(6) 0.0825(11) Uani 1 1 d . . .
H25 H 1.4875 0.1199 0.1434 0.099 Uiso 1 1 calc R . .
C26 C 1.3914(2) 0.11363(19) 0.3101(5) 0.0803(11) Uani 1 1 d . . .
H26 H 1.4345 0.0973 0.4075 0.096 Uiso 1 1 calc R . .
O1 O 1.10974(11) 0.29993(10) 0.1375(2) 0.0528(4) Uani 1 1 d . . .
C51 C 0.73240(17) 0.09065(14) 0.3341(3) 0.0484(5) Uani 1 1 d . . .
N51 N 0.66988(17) 0.04939(16) 0.3637(3) 0.0702(7) Uani 1 1 d . . .
O2 O 1.09935(17) 0.00465(12) 0.2561(4) 0.0831(7) Uani 1 1 d . . .
N1 N 0.89347(17) -0.00854(12) 0.2992(3) 0.0609(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.386(3) . ?
C2 C6 1.395(3) . ?
C2 C15 1.464(3) . ?
C3 C9 1.384(3) . ?
C3 C5 1.399(3) . ?
C4 C8 1.389(3) . ?
C4 C10 1.394(3) . ?
C4 C5 1.486(3) . ?
C5 C7 1.412(3) . ?
C6 N1 1.361(3) . ?
C6 C7 1.421(3) . ?
C7 C51 1.442(3) . ?
C8 C11 1.385(3) . ?
C9 C13 1.491(3) . ?
C10 C21 1.388(3) . ?
C11 C19 1.392(3) . ?
C12 C13 1.396(3) . ?
C12 C15 1.419(3) . ?
C12 C17 1.420(3) . ?
C13 O1 1.207(2) . ?
C15 O2 1.283(3) . ?
C17 C22 1.383(4) . ?
C17 C23 1.384(3) . ?
C19 C21 1.379(3) . ?
C22 C24 1.390(4) . ?
C23 C26 1.398(4) . ?
C24 C25 1.375(5) . ?
C25 C26 1.363(5) . ?
C51 N51 1.139(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
C9 C2 C6 121.93(19) . . ?
C9 C2 C15 108.73(18) . . ?
C6 C2 C15 129.30(19) . . ?
C9 C3 C5 117.88(18) . . ?
C8 C4 C10 118.94(19) . . ?
C8 C4 C5 119.06(18) . . ?
C10 C4 C5 121.95(18) . . ?
C3 C5 C7 119.57(18) . . ?
C3 C5 C4 118.00(17) . . ?
C7 C5 C4 122.43(18) . . ?
N1 C6 C2 121.4(2) . . ?
N1 C6 C7 123.0(2) . . ?
C2 C6 C7 115.55(18) . . ?
C5 C7 C6 122.53(18) . . ?
C5 C7 C51 121.91(19) . . ?
C6 C7 C51 115.54(19) . . ?
C11 C8 C4 120.9(2) . . ?
C3 C9 C2 122.51(19) . . ?
C3 C9 C13 129.12(18) . . ?
C2 C9 C13 108.35(17) . . ?
C21 C10 C4 120.0(2) . . ?
C8 C11 C19 119.9(2) . . ?
C13 C12 C15 111.49(18) . . ?
C13 C12 C17 125.01(19) . . ?
C15 C12 C17 123.43(18) . . ?
O1 C13 C12 125.9(2) . . ?
O1 C13 C9 128.60(19) . . ?
C12 C13 C9 105.49(17) . . ?
O2 C15 C12 127.8(2) . . ?
O2 C15 C2 126.3(2) . . ?
C12 C15 C2 105.90(17) . . ?
C22 C17 C23 120.4(2) . . ?
C22 C17 C12 119.8(2) . . ?
C23 C17 C12 119.7(2) . . ?
C21 C19 C11 119.4(2) . . ?
C19 C21 C10 120.8(2) . . ?
C17 C22 C24 119.6(3) . . ?
C17 C23 C26 119.0(3) . . ?
C25 C24 C22 120.0(3) . . ?
C26 C25 C24 120.6(3) . . ?
C25 C26 C23 120.5(3) . . ?
N51 C51 C7 172.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 977863'
#######################################################################
#
#                 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_8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22.50 H23 Cl Fe2 N O5 P Se2'
_chemical_formula_sum            'C22.50 H23 Cl Fe2 N O5 P Se2'
_chemical_formula_weight         723.46

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.6040(16)
_cell_length_b                   10.4610(17)
_cell_length_c                   13.6300(19)
_cell_angle_alpha                92.552(14)
_cell_angle_beta                 103.678(17)
_cell_angle_gamma                91.248(8)
_cell_volume                     1328.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4938
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      28.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             714
_exptl_absorpt_coefficient_mu    4.026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7942
_exptl_absorpt_correction_T_max  0.9238
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10004
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5074
_reflns_number_gt                4258
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.1295P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     327
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.059
_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
Se1 Se 0.10211(5) 0.06322(4) 0.14311(4) 0.02170(19) Uani 1 1 d . . .
Se2 Se 0.29664(5) 0.32347(4) 0.15260(4) 0.02216(19) Uani 1 1 d . . .
Fe1 Fe 0.27651(7) 0.17223(6) 0.27565(5) 0.0194(2) Uani 1 1 d . . .
Fe2 Fe 0.32680(7) 0.10679(7) 0.10187(5) 0.0226(2) Uani 1 1 d . . .
P1 P 0.15413(13) 0.27787(12) 0.37313(9) 0.0190(3) Uani 1 1 d . . .
O1 O 0.3141(5) -0.0653(4) 0.3831(3) 0.0392(10) Uani 1 1 d . . .
O2 O 0.5563(4) 0.2664(5) 0.3966(4) 0.0437(11) Uani 1 1 d . . .
O3 O 0.3663(4) -0.1703(4) 0.1091(3) 0.0393(10) Uani 1 1 d . . .
O4 O 0.2710(5) 0.1322(4) -0.1190(3) 0.0417(10) Uani 1 1 d . . .
O5 O 0.6378(5) 0.1598(5) 0.1661(4) 0.0497(12) Uani 1 1 d . . .
N1 N -0.0071(4) 0.2193(4) 0.3834(3) 0.0253(9) Uani 1 1 d . . .
C1 C 0.2980(6) 0.0276(5) 0.3400(4) 0.0263(11) Uani 1 1 d . . .
C2 C 0.4473(6) 0.2318(5) 0.3497(4) 0.0279(12) Uani 1 1 d . . .
C3 C 0.3507(5) -0.0614(5) 0.1058(4) 0.0284(12) Uani 1 1 d . . .
C4 C 0.2913(6) 0.1210(5) -0.0335(4) 0.0287(12) Uani 1 1 d . . .
C5 C 0.5179(6) 0.1403(5) 0.1397(4) 0.0307(12) Uani 1 1 d . . .
C6 C -0.0437(5) 0.1870(5) 0.0858(4) 0.0283(12) Uani 1 1 d . . .
H6A H -0.1305 0.1387 0.0469 0.034 Uiso 1 1 calc R . .
H6B H -0.0706 0.2354 0.1423 0.034 Uiso 1 1 calc R . .
C7 C 0.0011(6) 0.2807(5) 0.0184(4) 0.0289(12) Uani 1 1 d . . .
H7A H -0.0850 0.3235 -0.0189 0.035 Uiso 1 1 calc R . .
H7B H 0.0422 0.2333 -0.0320 0.035 Uiso 1 1 calc R . .
C8 C 0.1103(6) 0.3826(5) 0.0740(4) 0.0274(11) Uani 1 1 d . . .
H8A H 0.0656 0.4330 0.1209 0.033 Uiso 1 1 calc R . .
H8B H 0.1300 0.4415 0.0237 0.033 Uiso 1 1 calc R . .
C9 C 0.2589(5) 0.3001(5) 0.5056(4) 0.0225(10) Uani 1 1 d . . .
C10 C 0.2900(6) 0.1869(5) 0.5584(4) 0.0299(12) Uani 1 1 d . . .
H10 H 0.2595 0.1062 0.5247 0.036 Uiso 1 1 calc R . .
C11 C 0.3648(6) 0.1927(6) 0.6594(4) 0.0333(13) Uani 1 1 d . . .
H11 H 0.3849 0.1161 0.6942 0.040 Uiso 1 1 calc R . .
C12 C 0.4097(6) 0.3097(6) 0.7090(4) 0.0317(13) Uani 1 1 d . . .
H12 H 0.4605 0.3138 0.7780 0.038 Uiso 1 1 calc R . .
C13 C 0.3806(6) 0.4206(6) 0.6579(4) 0.0292(12) Uani 1 1 d . . .
H13 H 0.4127 0.5009 0.6920 0.035 Uiso 1 1 calc R . .
C14 C 0.3044(5) 0.4169(5) 0.5566(4) 0.0263(11) Uani 1 1 d . . .
H14 H 0.2838 0.4943 0.5228 0.032 Uiso 1 1 calc R . .
C15 C 0.1143(5) 0.4411(5) 0.3337(4) 0.0209(10) Uani 1 1 d . . .
C16 C -0.0264(6) 0.4822(5) 0.2981(4) 0.0281(12) Uani 1 1 d . . .
H16 H -0.1055 0.4265 0.2990 0.034 Uiso 1 1 calc R . .
C17 C -0.0503(6) 0.6049(6) 0.2614(4) 0.0335(13) Uani 1 1 d . . .
H17 H -0.1455 0.6318 0.2369 0.040 Uiso 1 1 calc R . .
C18 C 0.0661(7) 0.6877(5) 0.2608(4) 0.0333(13) Uani 1 1 d . . .
H18 H 0.0494 0.7709 0.2361 0.040 Uiso 1 1 calc R . .
C19 C 0.2061(6) 0.6486(5) 0.2962(4) 0.0286(12) Uani 1 1 d . . .
H19 H 0.2849 0.7047 0.2953 0.034 Uiso 1 1 calc R . .
C20 C 0.2298(6) 0.5268(5) 0.3329(4) 0.0246(11) Uani 1 1 d . . .
H20 H 0.3253 0.5009 0.3578 0.030 Uiso 1 1 calc R . .
C21 C -0.0663(6) 0.2746(6) 0.4648(4) 0.0304(12) Uani 1 1 d . . .
H21A H -0.1713 0.2678 0.4447 0.046 Uiso 1 1 calc R . .
H21B H -0.0354 0.3649 0.4779 0.046 Uiso 1 1 calc R . .
H21C H -0.0320 0.2280 0.5262 0.046 Uiso 1 1 calc R . .
C22 C -0.0530(6) 0.0853(6) 0.3582(4) 0.0314(13) Uani 1 1 d . . .
H22A H -0.0155 0.0341 0.4166 0.047 Uiso 1 1 calc R . .
H22B H -0.0163 0.0537 0.3007 0.047 Uiso 1 1 calc R . .
H22C H -0.1580 0.0781 0.3404 0.047 Uiso 1 1 calc R . .
Cl1 Cl 0.6594(5) 0.4673(5) 1.0836(3) 0.0532(11) Uani 0.50 1 d PD A -1
Cl2 Cl 0.3949(5) 0.5617(5) 0.9686(5) 0.0694(14) Uani 0.50 1 d PD A -1
C23 C 0.5177(10) 0.4435(10) 0.9774(8) 0.038(3) Uani 0.50 1 d PD A -1
H23A H 0.5560 0.4407 0.9160 0.046 Uiso 0.50 1 calc PR A -1
H23B H 0.4692 0.3598 0.9803 0.046 Uiso 0.50 1 calc PR A -1


_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
Se1 C6 1.975(5) . ?
Se1 Fe1 2.3815(10) . ?
Se1 Fe2 2.3946(9) . ?
Se2 C8 1.983(5) . ?
Se2 Fe2 2.3841(9) . ?
Se2 Fe1 2.3936(9) . ?
Fe1 C1 1.774(5) . ?
Fe1 C2 1.793(5) . ?
Fe1 P1 2.2432(15) . ?
Fe1 Fe2 2.5930(11) . ?
Fe2 C3 1.781(5) . ?
Fe2 C5 1.807(6) . ?
Fe2 C4 1.809(6) . ?
P1 N1 1.692(4) . ?
P1 C15 1.834(5) . ?
P1 C9 1.849(5) . ?
O1 C1 1.153(6) . ?
O2 C2 1.132(6) . ?
O3 C3 1.154(7) . ?
O4 C4 1.148(7) . ?
O5 C5 1.134(7) . ?
N1 C22 1.462(7) . ?
N1 C21 1.464(8) . ?
C6 C7 1.497(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.388(8) . ?
C9 C10 1.414(7) . ?
C10 C11 1.392(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.407(7) . ?
C15 C20 1.413(7) . ?
C16 C17 1.402(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.401(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C23 1.740(8) . ?
Cl2 C23 1.716(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Se1 Fe1 107.95(17) . . ?
C6 Se1 Fe2 112.11(16) . . ?
Fe1 Se1 Fe2 65.76(3) . . ?
C8 Se2 Fe2 109.53(16) . . ?
C8 Se2 Fe1 114.24(16) . . ?
Fe2 Se2 Fe1 65.74(3) . . ?
C1 Fe1 C2 90.2(2) . . ?
C1 Fe1 P1 98.20(18) . . ?
C2 Fe1 P1 93.47(19) . . ?
C1 Fe1 Se1 88.60(17) . . ?
C2 Fe1 Se1 160.15(19) . . ?
P1 Fe1 Se1 106.31(5) . . ?
C1 Fe1 Se2 158.78(18) . . ?
C2 Fe1 Se2 88.24(17) . . ?
P1 Fe1 Se2 103.01(4) . . ?
Se1 Fe1 Se2 85.73(3) . . ?
C1 Fe1 Fe2 103.07(18) . . ?
C2 Fe1 Fe2 103.77(19) . . ?
P1 Fe1 Fe2 152.37(5) . . ?
Se1 Fe1 Fe2 57.36(3) . . ?
Se2 Fe1 Fe2 56.95(3) . . ?
C3 Fe2 C5 92.0(2) . . ?
C3 Fe2 C4 98.8(3) . . ?
C5 Fe2 C4 101.7(2) . . ?
C3 Fe2 Se2 161.46(19) . . ?
C5 Fe2 Se2 87.30(18) . . ?
C4 Fe2 Se2 99.51(18) . . ?
C3 Fe2 Se1 86.00(17) . . ?
C5 Fe2 Se1 150.75(19) . . ?
C4 Fe2 Se1 107.50(17) . . ?
Se2 Fe2 Se1 85.65(3) . . ?
C3 Fe2 Fe1 104.42(18) . . ?
C5 Fe2 Fe1 95.78(19) . . ?
C4 Fe2 Fe1 150.37(17) . . ?
Se2 Fe2 Fe1 57.31(3) . . ?
Se1 Fe2 Fe1 56.88(3) . . ?
N1 P1 C15 102.8(2) . . ?
N1 P1 C9 103.9(2) . . ?
C15 P1 C9 104.2(2) . . ?
N1 P1 Fe1 120.16(17) . . ?
C15 P1 Fe1 112.48(17) . . ?
C9 P1 Fe1 111.75(17) . . ?
C22 N1 C21 112.1(4) . . ?
C22 N1 P1 122.5(4) . . ?
C21 N1 P1 117.6(4) . . ?
O1 C1 Fe1 178.7(5) . . ?
O2 C2 Fe1 178.3(5) . . ?
O3 C3 Fe2 179.5(5) . . ?
O4 C4 Fe2 178.5(5) . . ?
O5 C5 Fe2 178.0(5) . . ?
C7 C6 Se1 115.3(4) . . ?
C7 C6 H6A 108.4 . . ?
Se1 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
Se1 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 114.1(5) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 Se2 117.4(4) . . ?
C7 C8 H8A 108.0 . . ?
Se2 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
Se2 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
C14 C9 C10 118.6(5) . . ?
C14 C9 P1 125.6(4) . . ?
C10 C9 P1 115.8(4) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.1(6) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 119.9(5) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C20 118.5(4) . . ?
C16 C15 P1 122.8(4) . . ?
C20 C15 P1 118.6(4) . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.1(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 121.2(5) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl2 C23 Cl1 112.4(6) . . ?
Cl2 C23 H23A 109.1 . . ?
Cl1 C23 H23A 109.1 . . ?
Cl2 C23 H23B 109.1 . . ?
Cl1 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?

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
C6 Se1 Fe1 C1 146.7(2) . . . . ?
Fe2 Se1 Fe1 C1 -106.52(18) . . . . ?
C6 Se1 Fe1 C2 -126.4(5) . . . . ?
Fe2 Se1 Fe1 C2 -19.7(5) . . . . ?
C6 Se1 Fe1 P1 48.61(17) . . . . ?
Fe2 Se1 Fe1 P1 155.35(5) . . . . ?
C6 Se1 Fe1 Se2 -53.72(17) . . . . ?
Fe2 Se1 Fe1 Se2 53.02(3) . . . . ?
C6 Se1 Fe1 Fe2 -106.74(17) . . . . ?
C8 Se2 Fe1 C1 123.0(5) . . . . ?
Fe2 Se2 Fe1 C1 21.5(5) . . . . ?
C8 Se2 Fe1 C2 -150.8(3) . . . . ?
Fe2 Se2 Fe1 C2 107.70(19) . . . . ?
C8 Se2 Fe1 P1 -57.65(19) . . . . ?
Fe2 Se2 Fe1 P1 -159.14(5) . . . . ?
C8 Se2 Fe1 Se1 48.12(18) . . . . ?
Fe2 Se2 Fe1 Se1 -53.37(3) . . . . ?
C8 Se2 Fe1 Fe2 101.50(19) . . . . ?
C8 Se2 Fe2 C3 -119.0(6) . . . . ?
Fe1 Se2 Fe2 C3 -10.5(5) . . . . ?
C8 Se2 Fe2 C5 152.8(2) . . . . ?
Fe1 Se2 Fe2 C5 -98.63(18) . . . . ?
C8 Se2 Fe2 C4 51.5(2) . . . . ?
Fe1 Se2 Fe2 C4 160.00(18) . . . . ?
C8 Se2 Fe2 Se1 -55.57(17) . . . . ?
Fe1 Se2 Fe2 Se1 52.96(3) . . . . ?
C8 Se2 Fe2 Fe1 -108.53(17) . . . . ?
C6 Se1 Fe2 C3 -149.4(3) . . . . ?
Fe1 Se1 Fe2 C3 110.10(18) . . . . ?
C6 Se1 Fe2 C5 123.7(4) . . . . ?
Fe1 Se1 Fe2 C5 23.2(4) . . . . ?
C6 Se1 Fe2 C4 -51.5(3) . . . . ?
Fe1 Se1 Fe2 C4 -151.94(19) . . . . ?
C6 Se1 Fe2 Se2 47.15(19) . . . . ?
Fe1 Se1 Fe2 Se2 -53.33(3) . . . . ?
C6 Se1 Fe2 Fe1 100.48(19) . . . . ?
C1 Fe1 Fe2 C3 4.4(2) . . . . ?
C2 Fe1 Fe2 C3 97.9(2) . . . . ?
P1 Fe1 Fe2 C3 -135.00(19) . . . . ?
Se1 Fe1 Fe2 C3 -75.30(17) . . . . ?
Se2 Fe1 Fe2 C3 176.57(17) . . . . ?
C1 Fe1 Fe2 C5 -89.1(2) . . . . ?
C2 Fe1 Fe2 C5 4.4(2) . . . . ?
P1 Fe1 Fe2 C5 131.5(2) . . . . ?
Se1 Fe1 Fe2 C5 -168.83(18) . . . . ?
Se2 Fe1 Fe2 C5 83.04(18) . . . . ?
C1 Fe1 Fe2 C4 144.8(4) . . . . ?
C2 Fe1 Fe2 C4 -121.6(4) . . . . ?
P1 Fe1 Fe2 C4 5.4(4) . . . . ?
Se1 Fe1 Fe2 C4 65.1(4) . . . . ?
Se2 Fe1 Fe2 C4 -43.0(4) . . . . ?
C1 Fe1 Fe2 Se2 -172.16(17) . . . . ?
C2 Fe1 Fe2 Se2 -78.64(17) . . . . ?
P1 Fe1 Fe2 Se2 48.43(10) . . . . ?
Se1 Fe1 Fe2 Se2 108.13(3) . . . . ?
C1 Fe1 Fe2 Se1 79.72(17) . . . . ?
C2 Fe1 Fe2 Se1 173.24(17) . . . . ?
P1 Fe1 Fe2 Se1 -59.70(10) . . . . ?
Se2 Fe1 Fe2 Se1 -108.13(3) . . . . ?
C1 Fe1 P1 N1 -61.0(3) . . . . ?
C2 Fe1 P1 N1 -151.8(2) . . . . ?
Se1 Fe1 P1 N1 29.92(19) . . . . ?
Se2 Fe1 P1 N1 119.23(18) . . . . ?
Fe2 Fe1 P1 N1 79.2(2) . . . . ?
C1 Fe1 P1 C15 177.9(2) . . . . ?
C2 Fe1 P1 C15 87.1(2) . . . . ?
Se1 Fe1 P1 C15 -91.20(18) . . . . ?
Se2 Fe1 P1 C15 -1.89(18) . . . . ?
Fe2 Fe1 P1 C15 -41.9(2) . . . . ?
C1 Fe1 P1 C9 61.0(2) . . . . ?
C2 Fe1 P1 C9 -29.7(2) . . . . ?
Se1 Fe1 P1 C9 151.97(17) . . . . ?
Se2 Fe1 P1 C9 -118.72(18) . . . . ?
Fe2 Fe1 P1 C9 -158.78(18) . . . . ?
C15 P1 N1 C22 145.3(4) . . . . ?
C9 P1 N1 C22 -106.3(4) . . . . ?
Fe1 P1 N1 C22 19.5(5) . . . . ?
C15 P1 N1 C21 -68.1(4) . . . . ?
C9 P1 N1 C21 40.3(4) . . . . ?
Fe1 P1 N1 C21 166.1(3) . . . . ?
C2 Fe1 C1 O1 12(25) . . . . ?
P1 Fe1 C1 O1 -81(25) . . . . ?
Se1 Fe1 C1 O1 172(25) . . . . ?
Se2 Fe1 C1 O1 98(25) . . . . ?
Fe2 Fe1 C1 O1 116(25) . . . . ?
C1 Fe1 C2 O2 30(17) . . . . ?
P1 Fe1 C2 O2 128(17) . . . . ?
Se1 Fe1 C2 O2 -57(18) . . . . ?
Se2 Fe1 C2 O2 -129(17) . . . . ?
Fe2 Fe1 C2 O2 -74(17) . . . . ?
C5 Fe2 C3 O3 86(55) . . . . ?
C4 Fe2 C3 O3 -172(100) . . . . ?
Se2 Fe2 C3 O3 -1(55) . . . . ?
Se1 Fe2 C3 O3 -65(55) . . . . ?
Fe1 Fe2 C3 O3 -10(55) . . . . ?
C3 Fe2 C4 O4 -130(19) . . . . ?
C5 Fe2 C4 O4 -37(19) . . . . ?
Se2 Fe2 C4 O4 53(19) . . . . ?
Se1 Fe2 C4 O4 141(19) . . . . ?
Fe1 Fe2 C4 O4 88(19) . . . . ?
C3 Fe2 C5 O5 -65(16) . . . . ?
C4 Fe2 C5 O5 -164(16) . . . . ?
Se2 Fe2 C5 O5 97(16) . . . . ?
Se1 Fe2 C5 O5 21(16) . . . . ?
Fe1 Fe2 C5 O5 40(16) . . . . ?
Fe1 Se1 C6 C7 75.8(4) . . . . ?
Fe2 Se1 C6 C7 5.3(5) . . . . ?
Se1 C6 C7 C8 -72.0(6) . . . . ?
C6 C7 C8 Se2 60.1(6) . . . . ?
Fe2 Se2 C8 C7 15.9(4) . . . . ?
Fe1 Se2 C8 C7 -55.5(4) . . . . ?
N1 P1 C9 C14 -112.2(5) . . . . ?
C15 P1 C9 C14 -4.9(5) . . . . ?
Fe1 P1 C9 C14 116.8(4) . . . . ?
N1 P1 C9 C10 65.7(5) . . . . ?
C15 P1 C9 C10 173.0(4) . . . . ?
Fe1 P1 C9 C10 -65.3(4) . . . . ?
C14 C9 C10 C11 -0.1(8) . . . . ?
P1 C9 C10 C11 -178.2(4) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C10 C11 C12 C13 -0.2(8) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C10 C9 C14 C13 0.7(8) . . . . ?
P1 C9 C14 C13 178.6(4) . . . . ?
C12 C13 C14 C9 -1.1(8) . . . . ?
N1 P1 C15 C16 -14.1(5) . . . . ?
C9 P1 C15 C16 -122.2(5) . . . . ?
Fe1 P1 C15 C16 116.6(4) . . . . ?
N1 P1 C15 C20 170.2(4) . . . . ?
C9 P1 C15 C20 62.0(5) . . . . ?
Fe1 P1 C15 C20 -59.2(4) . . . . ?
C20 C15 C16 C17 0.9(8) . . . . ?
P1 C15 C16 C17 -174.8(4) . . . . ?
C15 C16 C17 C18 -0.6(9) . . . . ?
C16 C17 C18 C19 0.3(9) . . . . ?
C17 C18 C19 C20 -0.5(9) . . . . ?
C18 C19 C20 C15 0.9(8) . . . . ?
C16 C15 C20 C19 -1.1(8) . . . . ?
P1 C15 C20 C19 174.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.986
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.226
_database_code_depnum_ccdc_archive 'CCDC 971864'
