 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H16 Fe N2 O4'
_chemical_formula_weight          428.22
 
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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Fe'  'Fe'   0.3463   0.8444
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/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                    7.526(2)
_cell_length_b                    14.2210(10)
_cell_length_c                    17.276(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.34(2)
_cell_angle_gamma                 90.00
_cell_volume                      1847.5(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.14
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.540
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              880
_exptl_absorpt_coefficient_mu     0.849
_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       120(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             2678
_diffrn_reflns_av_R_equivalents   0.5935
_diffrn_reflns_av_sigmaI/netI     0.1798
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          24.93
_reflns_number_total              2633
_reflns_number_gt                 1765
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_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 > 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)+(0.1388P)²+140.1552P] 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          2633
_refine_ls_number_parameters      262
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0991
_refine_ls_R_factor_gt            0.0528
_refine_ls_wR_factor_ref          0.1685
_refine_ls_wR_factor_gt           0.1299
_refine_ls_goodness_of_fit_ref    0.342
_refine_ls_restrained_S_all       0.342
_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 0.11043(12) 0.16928(6) 0.27710(5) 0.0243(3) Uani 1 1 d . . .
N1 N 0.5482(8) 0.1089(4) 0.6517(3) 0.0346(13) Uani 1 1 d . . .
N2 N -0.2877(8) 0.5092(4) 0.5321(3) 0.0393(14) Uani 1 1 d . . .
O1 O 0.6644(7) 0.1710(3) 0.6578(3) 0.0429(12) Uani 1 1 d . . .
O2 O 0.5300(7) 0.0466(4) 0.7007(3) 0.0454(13) Uani 1 1 d . . .
O3 O -0.3402(8) 0.5789(3) 0.4940(3) 0.0537(15) Uani 1 1 d . . .
O4 O -0.2877(10) 0.5061(4) 0.6031(3) 0.073(2) Uani 1 1 d . . .
C1 C 0.2378(10) 0.2973(4) 0.2672(4) 0.0383(17) Uani 1 1 d . . .
H1 H 0.2231 0.3506 0.2994 0.046 Uiso 1 1 calc R . .
C2 C 0.1350(10) 0.2759(5) 0.1975(4) 0.0397(17) Uani 1 1 d . . .
H2 H 0.0397 0.3122 0.1756 0.048 Uiso 1 1 calc R . .
C3 C 0.2034(9) 0.1889(5) 0.1669(4) 0.0341(16) Uani 1 1 d . . .
H3 H 0.1614 0.1577 0.1211 0.041 Uiso 1 1 calc R . .
C4 C 0.3452(8) 0.1587(4) 0.2181(4) 0.0313(15) Uani 1 1 d . . .
H4 H 0.4150 0.1036 0.2123 0.038 Uiso 1 1 calc R . .
C5 C 0.3646(9) 0.2249(5) 0.2792(4) 0.0370(16) Uani 1 1 d . . .
H5 H 0.4491 0.2212 0.3215 0.044 Uiso 1 1 calc R . .
C6 C 0.0564(8) 0.0385(4) 0.3258(4) 0.0261(14) Uani 1 1 d . . .
H6 H 0.1279 -0.0165 0.3246 0.031 Uiso 1 1 calc R . .
C7 C -0.0817(8) 0.0645(4) 0.2699(4) 0.0297(14) Uani 1 1 d . . .
H7 H -0.1171 0.0292 0.2252 0.036 Uiso 1 1 calc R . .
C8 C -0.1565(8) 0.1518(4) 0.2926(4) 0.0293(14) Uani 1 1 d . . .
H8 H -0.2491 0.1848 0.2652 0.035 Uiso 1 1 calc R . .
C9 C -0.0677(8) 0.1820(4) 0.3647(3) 0.0235(13) Uani 1 1 d . . .
C10 C 0.0668(8) 0.1118(4) 0.3848(3) 0.0222(13) Uani 1 1 d . . .
C11 C 0.1949(8) 0.1115(4) 0.4525(3) 0.0234(13) Uani 1 1 d . . .
C12 C 0.2912(8) 0.1923(4) 0.4746(3) 0.0254(14) Uani 1 1 d . . .
H12 H 0.2745 0.2486 0.4457 0.031 Uiso 1 1 calc R . .
C13 C 0.4109(8) 0.1912(4) 0.5382(3) 0.0261(14) Uani 1 1 d . . .
H13 H 0.4790 0.2455 0.5516 0.031 Uiso 1 1 calc R . .
C14 C 0.4289(8) 0.1096(4) 0.5816(3) 0.0251(13) Uani 1 1 d . . .
C15 C 0.3343(8) 0.0274(4) 0.5621(4) 0.0281(14) Uani 1 1 d . . .
H15 H 0.3464 -0.0277 0.5931 0.034 Uiso 1 1 calc R . .
C16 C 0.2229(8) 0.0288(4) 0.4965(4) 0.0263(14) Uani 1 1 d . . .
H16 H 0.1637 -0.0274 0.4805 0.032 Uiso 1 1 calc R . .
C17 C -0.1200(8) 0.2670(4) 0.4086(3) 0.0253(13) Uani 1 1 d . . .
C18 C -0.1208(8) 0.2678(4) 0.4902(4) 0.0285(14) Uani 1 1 d . . .
H18 H -0.0832 0.2133 0.5181 0.034 Uiso 1 1 calc R . .
C19 C -0.1751(8) 0.3461(5) 0.5308(4) 0.0315(15) Uani 1 1 d . . .
H19 H -0.1740 0.3458 0.5858 0.038 Uiso 1 1 calc R . .
C20 C -0.2314(9) 0.4254(4) 0.4891(4) 0.0322(15) Uani 1 1 d . . .
C21 C -0.2359(10) 0.4269(5) 0.4080(4) 0.0399(17) Uani 1 1 d . . .
H21 H -0.2763 0.4814 0.3808 0.048 Uiso 1 1 calc R . .
C22 C -0.1811(10) 0.3483(5) 0.3677(4) 0.0373(16) Uani 1 1 d . . .
H22 H -0.1844 0.3490 0.3126 0.045 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Fe1 C6 2.088(6) . ?
Fe1 C9 2.070(6) . ?
Fe1 C7 2.077(6) . ?
Fe1 C2 2.060(6) . ?
Fe1 C5 2.068(7) . ?
Fe1 C10 2.071(5) . ?
Fe1 C4 2.081(6) . ?
Fe1 C8 2.053(6) . ?
Fe1 C3 2.074(6) . ?
Fe1 C1 2.068(6) . ?
N1 O2 1.237(7) . ?
N1 O1 1.244(7) . ?
N1 C14 1.477(8) . ?
N2 O4 1.228(8) . ?
N2 O3 1.245(7) . ?
N2 C20 1.476(8) . ?
C1 C5 1.413(10) . ?
C1 C2 1.436(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.449(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(9) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C10 1.458(8) . ?
C6 C7 1.438(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.425(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.454(8) . ?
C8 H8 0.9500 . ?
C9 C17 1.488(8) . ?
C9 C10 1.454(8) . ?
C10 C11 1.485(8) . ?
C11 C16 1.411(8) . ?
C11 C12 1.403(8) . ?
C12 C13 1.392(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(9) . ?
C15 C16 1.384(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.422(9) . ?
C17 C18 1.410(8) . ?
C18 C19 1.386(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(10) . ?
C21 C22 1.389(10) . ?
C21 H21 0.9500 . ?
C22 H22 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
C6 Fe1 C9 68.9(2) . . ?
C6 Fe1 C7 40.4(2) . . ?
C9 Fe1 C7 68.7(2) . . ?
C6 Fe1 C2 161.6(3) . . ?
C9 Fe1 C2 120.1(2) . . ?
C7 Fe1 C2 124.7(3) . . ?
C6 Fe1 C5 121.9(3) . . ?
C9 Fe1 C5 125.4(2) . . ?
C7 Fe1 C5 156.4(3) . . ?
C2 Fe1 C5 67.8(3) . . ?
C6 Fe1 C10 41.0(2) . . ?
C9 Fe1 C10 41.1(2) . . ?
C7 Fe1 C10 68.6(2) . . ?
C2 Fe1 C10 155.8(3) . . ?
C5 Fe1 C10 108.4(3) . . ?
C6 Fe1 C4 108.4(2) . . ?
C9 Fe1 C4 162.3(2) . . ?
C7 Fe1 C4 121.4(3) . . ?
C2 Fe1 C4 68.0(3) . . ?
C5 Fe1 C4 40.0(3) . . ?
C10 Fe1 C4 125.5(2) . . ?
C6 Fe1 C8 68.4(2) . . ?
C9 Fe1 C8 41.3(2) . . ?
C7 Fe1 C8 40.4(2) . . ?
C2 Fe1 C8 106.9(3) . . ?
C5 Fe1 C8 162.4(3) . . ?
C10 Fe1 C8 69.1(2) . . ?
C4 Fe1 C8 155.5(3) . . ?
C6 Fe1 C3 124.6(3) . . ?
C9 Fe1 C3 155.8(3) . . ?
C7 Fe1 C3 107.6(3) . . ?
C2 Fe1 C3 41.0(3) . . ?
C5 Fe1 C3 67.6(3) . . ?
C10 Fe1 C3 161.8(2) . . ?
C4 Fe1 C3 40.1(3) . . ?
C8 Fe1 C3 120.3(3) . . ?
C6 Fe1 C1 156.4(3) . . ?
C9 Fe1 C1 107.4(2) . . ?
C7 Fe1 C1 162.0(3) . . ?
C2 Fe1 C1 40.7(3) . . ?
C5 Fe1 C1 40.0(3) . . ?
C10 Fe1 C1 120.8(3) . . ?
C4 Fe1 C1 67.5(3) . . ?
C8 Fe1 C1 125.2(3) . . ?
C3 Fe1 C1 68.3(3) . . ?
O2 N1 O1 123.2(5) . . ?
O2 N1 C14 119.0(6) . . ?
O1 N1 C14 117.8(5) . . ?
O4 N2 O3 122.9(6) . . ?
O4 N2 C20 119.1(6) . . ?
O3 N2 C20 117.9(6) . . ?
C5 C1 C2 107.9(6) . . ?
C5 C1 Fe1 70.1(4) . . ?
C2 C1 Fe1 69.4(4) . . ?
C5 C1 H1 126.1 . . ?
C2 C1 H1 126.1 . . ?
Fe1 C1 H1 126.1 . . ?
C3 C2 C1 107.4(6) . . ?
C3 C2 Fe1 70.0(4) . . ?
C1 C2 Fe1 69.9(4) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Fe1 C2 H2 125.4 . . ?
C2 C3 C4 107.4(6) . . ?
C2 C3 Fe1 69.0(3) . . ?
C4 C3 Fe1 70.2(4) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
Fe1 C3 H3 126.1 . . ?
C3 C4 C5 108.3(6) . . ?
C3 C4 Fe1 69.7(3) . . ?
C5 C4 Fe1 69.5(4) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.5 . . ?
C1 C5 C4 109.0(6) . . ?
C1 C5 Fe1 70.0(4) . . ?
C4 C5 Fe1 70.5(4) . . ?
C1 C5 H5 125.5 . . ?
C4 C5 H5 125.5 . . ?
Fe1 C5 H5 125.6 . . ?
C10 C6 C7 107.6(5) . . ?
C10 C6 Fe1 68.8(3) . . ?
C7 C6 Fe1 69.4(3) . . ?
C10 C6 H6 126.2 . . ?
C7 C6 H6 126.2 . . ?
Fe1 C6 H6 127.2 . . ?
C8 C7 C6 108.8(5) . . ?
C8 C7 Fe1 68.9(3) . . ?
C6 C7 Fe1 70.2(3) . . ?
C8 C7 H7 125.6 . . ?
C6 C7 H7 125.6 . . ?
Fe1 C7 H7 126.8 . . ?
C7 C8 C9 108.7(5) . . ?
C7 C8 Fe1 70.7(4) . . ?
C9 C8 Fe1 70.0(3) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 H8 125.7 . . ?
Fe1 C8 H8 125.2 . . ?
C17 C9 C10 129.1(5) . . ?
C17 C9 C8 123.7(5) . . ?
C10 C9 C8 107.1(5) . . ?
C17 C9 Fe1 129.5(4) . . ?
C10 C9 Fe1 69.5(3) . . ?
C8 C9 Fe1 68.7(3) . . ?
C6 C10 C11 124.3(5) . . ?
C6 C10 C9 107.8(5) . . ?
C11 C10 C9 127.9(5) . . ?
C6 C10 Fe1 70.1(3) . . ?
C11 C10 Fe1 126.0(4) . . ?
C9 C10 Fe1 69.4(3) . . ?
C16 C11 C12 118.2(5) . . ?
C16 C11 C10 120.3(5) . . ?
C12 C11 C10 121.5(5) . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 118.8(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.1(6) . . ?
C13 C14 N1 119.5(6) . . ?
C15 C14 N1 118.5(5) . . ?
C16 C15 C14 118.0(5) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C11 121.7(6) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C9 C17 C22 119.6(5) . . ?
C9 C17 C18 121.9(5) . . ?
C22 C17 C18 118.3(6) . . ?
C17 C18 C19 121.7(6) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 118.6(6) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 N2 118.7(6) . . ?
C19 C20 C21 121.6(6) . . ?
N2 C20 C21 119.7(6) . . ?
C22 C21 C20 119.6(6) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 120.1(6) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
 
_diffrn_measured_fraction_theta_max    0.816
_diffrn_reflns_theta_full              24.93
_diffrn_measured_fraction_theta_full   0.816
_refine_diff_density_max    0.358
_refine_diff_density_min   -0.442
_refine_diff_density_rms    0.094
