data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. I. R. Butler
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H15 Fe N O'
_chemical_formula_sum
 'C18 H15 Fe N O'
_chemical_formula_weight          317.16
 
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                    5.92370(10)
_cell_length_b                    10.5721(2)
_cell_length_c                    22.1342(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  95.0630(10)
_cell_angle_gamma                 90.00
_cell_volume                      1380.77(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3016
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Red
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.36
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.526
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              656
_exptl_absorpt_coefficient_mu     1.089
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6577
_exptl_absorpt_correction_T_max   0.8804
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12328
_diffrn_reflns_av_R_equivalents   0.0423
_diffrn_reflns_av_sigmaI/netI     0.0371
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          3.38
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3151
_reflns_number_gt                 2722
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0425P)²+0.5060P] 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_number_reflns          3151
_refine_ls_number_parameters      250
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0382
_refine_ls_R_factor_gt            0.0306
_refine_ls_wR_factor_ref          0.0796
_refine_ls_wR_factor_gt           0.0761
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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
Fe1 Fe 0.84268(4) 0.08488(2) 0.829944(10) 0.01282(9) Uani 1 1 d . . .
O1 O 0.2097(2) 0.05262(12) 0.62217(6) 0.0212(3) Uani 1 1 d . . .
N1 N 0.6251(2) -0.14049(14) 0.56225(6) 0.0181(3) Uani 1 1 d . . .
C1 C 0.7691(3) 0.16176(15) 0.74540(7) 0.0142(3) Uani 1 1 d . . .
C2 C 0.9968(3) 0.11427(17) 0.75212(8) 0.0167(3) Uani 1 1 d . . .
C3 C 1.1157(3) 0.17989(17) 0.80120(8) 0.0187(3) Uani 1 1 d . . .
C4 C 0.9649(3) 0.26686(16) 0.82582(8) 0.0172(3) Uani 1 1 d . . .
C5 C 0.7503(3) 0.25625(15) 0.79186(8) 0.0156(3) Uani 1 1 d . . .
C6 C 0.6079(3) -0.05308(17) 0.84172(8) 0.0212(4) Uani 1 1 d . . .
C7 C 0.8268(3) -0.10766(18) 0.84046(9) 0.0258(4) Uani 1 1 d . . .
C8 C 0.9697(3) -0.05267(18) 0.88847(10) 0.0268(4) Uani 1 1 d . . .
C9 C 0.8397(3) 0.03489(18) 0.91961(8) 0.0231(4) Uani 1 1 d . . .
C10 C 0.6160(3) 0.03483(17) 0.89076(8) 0.0197(4) Uani 1 1 d . . .
C11 C 0.5842(3) 0.12083(16) 0.70264(7) 0.0146(3) Uani 1 1 d . . .
C12 C 0.6002(3) 0.04008(16) 0.65632(8) 0.0164(3) Uani 1 1 d . . .
C13 C 0.3971(3) 0.00715(15) 0.61631(7) 0.0150(3) Uani 1 1 d . . .
C14 C 0.4217(3) -0.08650(14) 0.56584(8) 0.0144(3) Uani 1 1 d . . .
C15 C 0.2342(3) -0.11077(17) 0.52490(8) 0.0178(3) Uani 1 1 d . . .
C16 C 0.2600(3) -0.19001(17) 0.47604(8) 0.0210(4) Uani 1 1 d . . .
C17 C 0.4690(3) -0.24589(17) 0.47128(8) 0.0223(4) Uani 1 1 d . . .
C18 C 0.6435(3) -0.21976(17) 0.51569(8) 0.0209(4) Uani 1 1 d . . .
H2 H 1.059(3) 0.0516(19) 0.7278(9) 0.017(5) Uiso 1 1 d . . .
H3 H 1.263(4) 0.1675(19) 0.8167(9) 0.025(5) Uiso 1 1 d . . .
H4 H 1.000(3) 0.3182(18) 0.8594(9) 0.016(5) Uiso 1 1 d . . .
H5 H 0.621(3) 0.3001(19) 0.7995(9) 0.020(5) Uiso 1 1 d . . .
H6 H 0.479(4) -0.068(2) 0.8160(11) 0.035(6) Uiso 1 1 d . . .
H7 H 0.868(4) -0.167(2) 0.8126(11) 0.035(6) Uiso 1 1 d . . .
H8 H 1.132(4) -0.070(2) 0.8990(11) 0.033(6) Uiso 1 1 d . . .
H9 H 0.899(4) 0.087(2) 0.9532(11) 0.030(6) Uiso 1 1 d . . .
H10 H 0.497(4) 0.087(2) 0.9008(11) 0.028(6) Uiso 1 1 d . . .
H11 H 0.439(3) 0.1559(19) 0.7083(9) 0.020(5) Uiso 1 1 d . . .
H12 H 0.741(4) 0.0042(19) 0.6481(9) 0.022(5) Uiso 1 1 d . . .
H15 H 0.105(4) -0.0702(19) 0.5299(9) 0.019(5) Uiso 1 1 d . . .
H16 H 0.140(3) -0.203(2) 0.4479(10) 0.025(5) Uiso 1 1 d . . .
H17 H 0.493(3) -0.301(2) 0.4387(10) 0.027(6) Uiso 1 1 d . . .
H18 H 0.789(4) -0.258(2) 0.5140(10) 0.031(6) 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
Fe1 C2 2.0432(17) . ?
Fe1 C8 2.0461(18) . ?
Fe1 C6 2.0476(18) . ?
Fe1 C7 2.0519(19) . ?
Fe1 C10 2.0529(17) . ?
Fe1 C1 2.0516(16) . ?
Fe1 C5 2.0522(17) . ?
Fe1 C3 2.0519(17) . ?
Fe1 C9 2.0554(18) . ?
Fe1 C4 2.0604(17) . ?
O1 C13 1.227(2) . ?
N1 C18 1.340(2) . ?
N1 C14 1.342(2) . ?
C1 C2 1.435(2) . ?
C1 C5 1.445(2) . ?
C1 C11 1.449(2) . ?
C2 C3 1.422(2) . ?
C2 H2 0.95(2) . ?
C3 C4 1.423(3) . ?
C3 H3 0.92(2) . ?
C4 C5 1.423(2) . ?
C4 H4 0.93(2) . ?
C5 H5 0.92(2) . ?
C6 C7 1.421(3) . ?
C6 C10 1.427(3) . ?
C6 H6 0.93(2) . ?
C7 C8 1.423(3) . ?
C7 H7 0.93(2) . ?
C8 C9 1.421(3) . ?
C8 H8 0.98(2) . ?
C9 C10 1.419(3) . ?
C9 H9 0.96(2) . ?
C10 H10 0.94(2) . ?
C11 C12 1.344(2) . ?
C11 H11 0.95(2) . ?
C12 C13 1.471(2) . ?
C12 H12 0.95(2) . ?
C13 C14 1.509(2) . ?
C14 C15 1.394(2) . ?
C15 C16 1.387(3) . ?
C15 H15 0.89(2) . ?
C16 C17 1.384(3) . ?
C16 H16 0.91(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.95(2) . ?
C18 H18 0.96(2) . ?
 
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 Fe1 C8 118.37(8) . . ?
C2 Fe1 C6 125.08(7) . . ?
C8 Fe1 C6 68.23(8) . . ?
C2 Fe1 C7 105.96(8) . . ?
C8 Fe1 C7 40.64(8) . . ?
C6 Fe1 C7 40.57(8) . . ?
C2 Fe1 C10 163.50(7) . . ?
C8 Fe1 C10 68.09(8) . . ?
C6 Fe1 C10 40.72(7) . . ?
C7 Fe1 C10 68.32(8) . . ?
C2 Fe1 C1 41.02(6) . . ?
C8 Fe1 C1 153.61(8) . . ?
C6 Fe1 C1 107.83(7) . . ?
C7 Fe1 C1 119.23(7) . . ?
C10 Fe1 C1 126.99(7) . . ?
C2 Fe1 C5 69.04(7) . . ?
C8 Fe1 C5 163.21(8) . . ?
C6 Fe1 C5 121.44(7) . . ?
C7 Fe1 C5 155.39(8) . . ?
C10 Fe1 C5 109.31(7) . . ?
C1 Fe1 C5 41.23(6) . . ?
C2 Fe1 C3 40.64(7) . . ?
C8 Fe1 C3 106.76(7) . . ?
C6 Fe1 C3 161.95(8) . . ?
C7 Fe1 C3 124.49(8) . . ?
C10 Fe1 C3 155.29(7) . . ?
C1 Fe1 C3 68.48(7) . . ?
C5 Fe1 C3 68.25(7) . . ?
C2 Fe1 C9 153.59(7) . . ?
C8 Fe1 C9 40.53(8) . . ?
C6 Fe1 C9 68.30(7) . . ?
C7 Fe1 C9 68.35(8) . . ?
C10 Fe1 C9 40.43(7) . . ?
C1 Fe1 C9 164.46(7) . . ?
C5 Fe1 C9 126.80(7) . . ?
C3 Fe1 C9 119.95(7) . . ?
C2 Fe1 C4 68.64(7) . . ?
C8 Fe1 C4 125.50(8) . . ?
C6 Fe1 C4 156.34(7) . . ?
C7 Fe1 C4 162.02(8) . . ?
C10 Fe1 C4 121.49(7) . . ?
C1 Fe1 C4 68.71(7) . . ?
C5 Fe1 C4 40.49(7) . . ?
C3 Fe1 C4 40.50(7) . . ?
C9 Fe1 C4 108.41(7) . . ?
C18 N1 C14 116.50(15) . . ?
C2 C1 C5 107.38(14) . . ?
C2 C1 C11 127.80(15) . . ?
C5 C1 C11 124.75(15) . . ?
C2 C1 Fe1 69.17(9) . . ?
C5 C1 Fe1 69.40(9) . . ?
C11 C1 Fe1 124.40(11) . . ?
C3 C2 C1 107.83(15) . . ?
C3 C2 Fe1 70.01(10) . . ?
C1 C2 Fe1 69.80(9) . . ?
C3 C2 H2 125.8(12) . . ?
C1 C2 H2 126.3(12) . . ?
Fe1 C2 H2 126.7(12) . . ?
C2 C3 C4 108.81(15) . . ?
C2 C3 Fe1 69.35(9) . . ?
C4 C3 Fe1 70.07(9) . . ?
C2 C3 H3 127.3(13) . . ?
C4 C3 H3 123.8(13) . . ?
Fe1 C3 H3 124.3(13) . . ?
C5 C4 C3 107.96(15) . . ?
C5 C4 Fe1 69.44(9) . . ?
C3 C4 Fe1 69.43(10) . . ?
C5 C4 H4 126.5(11) . . ?
C3 C4 H4 125.5(12) . . ?
Fe1 C4 H4 124.4(12) . . ?
C4 C5 C1 108.01(14) . . ?
C4 C5 Fe1 70.07(9) . . ?
C1 C5 Fe1 69.36(9) . . ?
C4 C5 H5 125.5(13) . . ?
C1 C5 H5 126.5(13) . . ?
Fe1 C5 H5 124.3(13) . . ?
C7 C6 C10 108.06(16) . . ?
C7 C6 Fe1 69.88(10) . . ?
C10 C6 Fe1 69.84(10) . . ?
C7 C6 H6 128.6(15) . . ?
C10 C6 H6 123.3(15) . . ?
Fe1 C6 H6 125.3(15) . . ?
C6 C7 C8 107.64(17) . . ?
C6 C7 Fe1 69.55(10) . . ?
C8 C7 Fe1 69.46(11) . . ?
C6 C7 H7 125.6(14) . . ?
C8 C7 H7 126.7(14) . . ?
Fe1 C7 H7 125.5(15) . . ?
C9 C8 C7 108.45(17) . . ?
C9 C8 Fe1 70.09(11) . . ?
C7 C8 Fe1 69.90(11) . . ?
C9 C8 H8 124.3(14) . . ?
C7 C8 H8 127.3(14) . . ?
Fe1 C8 H8 125.1(14) . . ?
C10 C9 C8 107.81(17) . . ?
C10 C9 Fe1 69.69(10) . . ?
C8 C9 Fe1 69.39(11) . . ?
C10 C9 H9 127.4(14) . . ?
C8 C9 H9 124.7(14) . . ?
Fe1 C9 H9 124.3(14) . . ?
C9 C10 C6 108.05(16) . . ?
C9 C10 Fe1 69.88(10) . . ?
C6 C10 Fe1 69.44(10) . . ?
C9 C10 H10 125.6(14) . . ?
C6 C10 H10 126.2(14) . . ?
Fe1 C10 H10 123.5(14) . . ?
C12 C11 C1 126.00(15) . . ?
C12 C11 H11 118.1(12) . . ?
C1 C11 H11 115.9(12) . . ?
C11 C12 C13 120.03(15) . . ?
C11 C12 H12 121.5(13) . . ?
C13 C12 H12 118.5(12) . . ?
O1 C13 C12 122.88(15) . . ?
O1 C13 C14 118.85(15) . . ?
C12 C13 C14 118.27(14) . . ?
N1 C14 C15 123.45(16) . . ?
N1 C14 C13 117.95(15) . . ?
C15 C14 C13 118.59(15) . . ?
C16 C15 C14 118.78(16) . . ?
C16 C15 H15 122.8(13) . . ?
C14 C15 H15 118.3(13) . . ?
C17 C16 C15 118.57(17) . . ?
C17 C16 H16 122.0(13) . . ?
C15 C16 H16 119.5(13) . . ?
C16 C17 C18 118.41(16) . . ?
C16 C17 H17 121.0(13) . . ?
C18 C17 H17 120.6(13) . . ?
N1 C18 C17 124.20(16) . . ?
N1 C18 H18 115.5(13) . . ?
C17 C18 H18 120.3(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.355
_refine_diff_density_min   -0.660
_refine_diff_density_rms    0.070
