 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C26 H20 Fe N2 O2'
_chemical_formula_sum
 'C26 H20 Fe N2 O2'
_chemical_formula_weight          448.29
 
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'   0.3463   0.8444
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    13.0933(5)
_cell_length_b                    10.3440(4)
_cell_length_c                    15.4112(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.319(2)
_cell_angle_gamma                 90.00
_cell_volume                      1944.42(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     29674
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             'dark brown'
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.531
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              928
_exptl_absorpt_coefficient_mu     0.803
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6895
_exptl_absorpt_correction_T_max   0.9097
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             16057
_diffrn_reflns_av_R_equivalents   0.0534
_diffrn_reflns_av_sigmaI/netI     0.0461
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.34
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4424
_reflns_number_gt                 3520
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0452P)²+0.5584P] 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          4424
_refine_ls_number_parameters      280
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0511
_refine_ls_R_factor_gt            0.0357
_refine_ls_wR_factor_ref          0.0920
_refine_ls_wR_factor_gt           0.0844
_refine_ls_goodness_of_fit_ref    1.027
_refine_ls_restrained_S_all       1.027
_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 0.52176(14) 0.72470(17) 0.30959(12) 0.0184(4) Uani 1 1 d . . .
C2 C 0.44026(14) 0.63537(17) 0.31624(12) 0.0202(4) Uani 1 1 d . . .
H2 H 0.4425 0.5439 0.3120 0.024 Uiso 1 1 calc R . .
C3 C 0.35633(15) 0.70898(19) 0.33019(12) 0.0231(4) Uani 1 1 d . . .
H3 H 0.2929 0.6748 0.3380 0.028 Uiso 1 1 calc R . .
C4 C 0.38243(15) 0.84232(18) 0.33058(12) 0.0227(4) Uani 1 1 d . . .
H4 H 0.3395 0.9124 0.3382 0.027 Uiso 1 1 calc R . .
C5 C 0.48355(14) 0.85219(17) 0.31759(11) 0.0193(4) Uani 1 1 d . . .
H5 H 0.5201 0.9304 0.3146 0.023 Uiso 1 1 calc R . .
C6 C 0.62075(13) 0.68785(17) 0.29470(11) 0.0176(4) Uani 1 1 d . . .
H6 H 0.6274 0.5997 0.2803 0.021 Uiso 1 1 calc R . .
C7 C 0.70382(14) 0.76622(16) 0.29927(12) 0.0192(4) Uani 1 1 d . . .
H7 H 0.6988 0.8562 0.3094 0.023 Uiso 1 1 calc R . .
C8 C 0.80246(15) 0.71369(17) 0.28863(12) 0.0192(4) Uani 1 1 d . . .
C9 C 0.90185(14) 0.79816(16) 0.31154(12) 0.0184(4) Uani 1 1 d . . .
C10 C 0.99922(16) 0.97393(18) 0.38750(13) 0.0246(4) Uani 1 1 d . . .
H10 H 1.0050 1.0479 0.4255 0.030 Uiso 1 1 calc R . .
C11 C 1.08649(15) 0.94574(17) 0.36007(12) 0.0243(4) Uani 1 1 d . . .
H11 H 1.1503 0.9983 0.3793 0.029 Uiso 1 1 calc R . .
C12 C 1.07802(15) 0.83919(18) 0.30403(13) 0.0248(4) Uani 1 1 d . . .
H12 H 1.1350 0.8189 0.2819 0.030 Uiso 1 1 calc R . .
C13 C 0.98532(15) 0.76208(16) 0.28040(13) 0.0205(4) Uani 1 1 d . . .
H13 H 0.9788 0.6864 0.2438 0.025 Uiso 1 1 calc R . .
C14 C 0.37998(15) 0.73711(16) 0.07545(12) 0.0195(4) Uani 1 1 d . . .
C15 C 0.29913(15) 0.65098(18) 0.08646(12) 0.0221(4) Uani 1 1 d . . .
H15 H 0.2990 0.5594 0.0816 0.027 Uiso 1 1 calc R . .
C16 C 0.21973(15) 0.72684(18) 0.10588(13) 0.0239(4) Uani 1 1 d . . .
H16 H 0.1572 0.6947 0.1163 0.029 Uiso 1 1 calc R . .
C17 C 0.24960(15) 0.85932(18) 0.10703(12) 0.0233(4) Uani 1 1 d . . .
H17 H 0.2103 0.9308 0.1179 0.028 Uiso 1 1 calc R . .
C18 C 0.34804(15) 0.86573(17) 0.08911(11) 0.0211(4) Uani 1 1 d . . .
H18 H 0.3866 0.9426 0.0866 0.025 Uiso 1 1 calc R . .
C19 C 0.47815(14) 0.69512(17) 0.06100(11) 0.0193(4) Uani 1 1 d . . .
H19 H 0.4842 0.6054 0.0506 0.023 Uiso 1 1 calc R . .
C20 C 0.56137(15) 0.77082(17) 0.06097(12) 0.0202(4) Uani 1 1 d . . .
H20 H 0.5582 0.8613 0.0702 0.024 Uiso 1 1 calc R . .
C21 C 0.65686(15) 0.71537(18) 0.04685(12) 0.0203(4) Uani 1 1 d . . .
C22 C 0.75337(15) 0.80250(17) 0.05790(12) 0.0192(4) Uani 1 1 d . . .
C23 C 0.84613(16) 0.98977(18) 0.11327(13) 0.0268(4) Uani 1 1 d . . .
H23 H 0.8508 1.0706 0.1437 0.032 Uiso 1 1 calc R . .
C24 C 0.93123(16) 0.95494(18) 0.08493(13) 0.0261(4) Uani 1 1 d . . .
H24 H 0.9929 1.0099 0.0966 0.031 Uiso 1 1 calc R . .
C25 C 0.92438(16) 0.83866(18) 0.03938(12) 0.0249(4) Uani 1 1 d . . .
H25 H 0.9806 0.8128 0.0178 0.030 Uiso 1 1 calc R . .
C26 C 0.83405(16) 0.76010(17) 0.02560(13) 0.0223(4) Uani 1 1 d . . .
H26 H 0.8274 0.6792 -0.0052 0.027 Uiso 1 1 calc R . .
N1 N 0.90726(12) 0.90346(14) 0.36379(10) 0.0221(3) Uani 1 1 d . . .
N2 N 0.75740(13) 0.91622(14) 0.10036(11) 0.0231(3) Uani 1 1 d . . .
O1 O 0.80776(11) 0.60166(12) 0.26353(9) 0.0258(3) Uani 1 1 d . . .
O2 O 0.66227(11) 0.60134(12) 0.02684(9) 0.0254(3) Uani 1 1 d . . .
Fe1 Fe 0.37105(2) 0.75816(2) 0.206129(17) 0.01663(9) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C5 1.432(2) . ?
C1 C2 1.443(2) . ?
C1 C6 1.447(2) . ?
C1 Fe1 2.0659(17) . ?
C2 C3 1.416(3) . ?
C2 Fe1 2.0484(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(3) . ?
C3 Fe1 2.0542(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(3) . ?
C4 Fe1 2.0618(17) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.0559(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.338(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.464(3) . ?
C7 H7 0.9500 . ?
C8 O1 1.232(2) . ?
C8 C9 1.499(3) . ?
C9 N1 1.341(2) . ?
C9 C13 1.395(2) . ?
C10 N1 1.340(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C18 1.433(2) . ?
C14 C15 1.440(3) . ?
C14 C19 1.449(3) . ?
C14 Fe1 2.0708(18) . ?
C15 C16 1.418(3) . ?
C15 Fe1 2.0626(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.423(3) . ?
C16 Fe1 2.0473(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(3) . ?
C17 Fe1 2.0471(18) . ?
C17 H17 0.9500 . ?
C18 Fe1 2.0460(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.342(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.462(3) . ?
C20 H20 0.9500 . ?
C21 O2 1.228(2) . ?
C21 C22 1.511(3) . ?
C22 N2 1.338(2) . ?
C22 C26 1.392(3) . ?
C23 N2 1.342(2) . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C5 C1 C2 107.05(16) . . ?
C5 C1 C6 128.13(16) . . ?
C2 C1 C6 124.79(16) . . ?
C5 C1 Fe1 69.30(10) . . ?
C2 C1 Fe1 68.81(10) . . ?
C6 C1 Fe1 125.52(12) . . ?
C3 C2 C1 107.52(16) . . ?
C3 C2 Fe1 70.03(10) . . ?
C1 C2 Fe1 70.12(10) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 125.2 . . ?
C2 C3 C4 108.90(16) . . ?
C2 C3 Fe1 69.59(10) . . ?
C4 C3 Fe1 70.10(10) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
Fe1 C3 H3 126.3 . . ?
C5 C4 C3 107.82(16) . . ?
C5 C4 Fe1 69.71(10) . . ?
C3 C4 Fe1 69.52(10) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
Fe1 C4 H4 126.2 . . ?
C4 C5 C1 108.69(15) . . ?
C4 C5 Fe1 70.16(10) . . ?
C1 C5 Fe1 70.06(10) . . ?
C4 C5 H5 125.7 . . ?
C1 C5 H5 125.7 . . ?
Fe1 C5 H5 125.7 . . ?
C7 C6 C1 126.15(16) . . ?
C7 C6 H6 116.9 . . ?
C1 C6 H6 116.9 . . ?
C6 C7 C8 120.17(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C8 C7 122.49(16) . . ?
O1 C8 C9 118.63(16) . . ?
C7 C8 C9 118.87(15) . . ?
N1 C9 C13 123.17(16) . . ?
N1 C9 C8 117.81(16) . . ?
C13 C9 C8 118.99(16) . . ?
N1 C10 C11 124.14(17) . . ?
N1 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C12 C11 C10 118.14(17) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 119.18(17) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C9 118.46(17) . . ?
C12 C13 H13 120.8 . . ?
C9 C13 H13 120.8 . . ?
C18 C14 C15 106.91(16) . . ?
C18 C14 C19 128.58(16) . . ?
C15 C14 C19 124.33(16) . . ?
C18 C14 Fe1 68.70(10) . . ?
C15 C14 Fe1 69.30(10) . . ?
C19 C14 Fe1 123.23(12) . . ?
C16 C15 C14 108.00(16) . . ?
C16 C15 Fe1 69.23(10) . . ?
C14 C15 Fe1 69.92(10) . . ?
C16 C15 H15 126.0 . . ?
C14 C15 H15 126.0 . . ?
Fe1 C15 H15 126.4 . . ?
C15 C16 C17 108.43(16) . . ?
C15 C16 Fe1 70.39(10) . . ?
C17 C16 Fe1 69.65(10) . . ?
C15 C16 H16 125.8 . . ?
C17 C16 H16 125.8 . . ?
Fe1 C16 H16 125.8 . . ?
C18 C17 C16 107.96(16) . . ?
C18 C17 Fe1 69.74(10) . . ?
C16 C17 Fe1 69.67(10) . . ?
C18 C17 H17 126.0 . . ?
C16 C17 H17 126.0 . . ?
Fe1 C17 H17 126.1 . . ?
C17 C18 C14 108.69(16) . . ?
C17 C18 Fe1 69.82(10) . . ?
C14 C18 Fe1 70.56(10) . . ?
C17 C18 H18 125.7 . . ?
C14 C18 H18 125.7 . . ?
Fe1 C18 H18 125.5 . . ?
C20 C19 C14 126.23(17) . . ?
C20 C19 H19 116.9 . . ?
C14 C19 H19 116.9 . . ?
C19 C20 C21 120.63(17) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O2 C21 C20 123.02(17) . . ?
O2 C21 C22 118.63(17) . . ?
C20 C21 C22 118.35(16) . . ?
N2 C22 C26 123.49(17) . . ?
N2 C22 C21 117.54(16) . . ?
C26 C22 C21 118.96(16) . . ?
N2 C23 C24 123.96(17) . . ?
N2 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C25 C24 C23 118.48(18) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 118.90(18) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C22 118.46(17) . . ?
C25 C26 H26 120.8 . . ?
C22 C26 H26 120.8 . . ?
C10 N1 C9 116.86(16) . . ?
C23 N2 C22 116.69(16) . . ?
C18 Fe1 C17 40.44(7) . . ?
C18 Fe1 C16 68.22(7) . . ?
C17 Fe1 C16 40.69(7) . . ?
C18 Fe1 C2 161.16(7) . . ?
C17 Fe1 C2 157.63(8) . . ?
C16 Fe1 C2 122.84(8) . . ?
C18 Fe1 C3 157.15(8) . . ?
C17 Fe1 C3 120.71(8) . . ?
C16 Fe1 C3 105.70(8) . . ?
C2 Fe1 C3 40.39(7) . . ?
C18 Fe1 C5 108.08(7) . . ?
C17 Fe1 C5 120.52(7) . . ?
C16 Fe1 C5 155.26(7) . . ?
C2 Fe1 C5 68.56(7) . . ?
C3 Fe1 C5 67.71(7) . . ?
C18 Fe1 C4 121.87(7) . . ?
C17 Fe1 C4 104.60(7) . . ?
C16 Fe1 C4 119.45(8) . . ?
C2 Fe1 C4 68.32(7) . . ?
C3 Fe1 C4 40.37(7) . . ?
C5 Fe1 C4 40.14(7) . . ?
C18 Fe1 C15 68.36(7) . . ?
C17 Fe1 C15 68.25(7) . . ?
C16 Fe1 C15 40.38(7) . . ?
C2 Fe1 C15 109.15(7) . . ?
C3 Fe1 C15 122.16(8) . . ?
C5 Fe1 C15 163.12(7) . . ?
C4 Fe1 C15 156.04(8) . . ?
C18 Fe1 C1 124.38(7) . . ?
C17 Fe1 C1 157.88(7) . . ?
C16 Fe1 C1 161.20(8) . . ?
C2 Fe1 C1 41.06(7) . . ?
C3 Fe1 C1 68.08(7) . . ?
C5 Fe1 C1 40.64(7) . . ?
C4 Fe1 C1 68.10(7) . . ?
C15 Fe1 C1 126.69(7) . . ?
C18 Fe1 C14 40.73(7) . . ?
C17 Fe1 C14 68.37(7) . . ?
C16 Fe1 C14 68.33(7) . . ?
C2 Fe1 C14 125.18(7) . . ?
C3 Fe1 C14 159.52(7) . . ?
C5 Fe1 C14 125.85(7) . . ?
C4 Fe1 C14 159.82(7) . . ?
C15 Fe1 C14 40.78(7) . . ?
C1 Fe1 C14 110.93(7) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.462
_refine_diff_density_min   -0.555
_refine_diff_density_rms    0.066
