data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. I. R. Butler
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H23 Fe N O2'
_chemical_formula_weight          389.26
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.6203(11)
_cell_length_b                    10.5084(13)
_cell_length_c                    11.3286(15)
_cell_angle_alpha                 80.528(5)
_cell_angle_beta                  73.494(5)
_cell_angle_gamma                 71.177(5)
_cell_volume                      928.3(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3859
_cell_measurement_theta_min       0.998
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Shard
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              408
_exptl_absorpt_coefficient_mu     0.828
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9072
_exptl_absorpt_correction_T_max   0.9918
_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             15966
_diffrn_reflns_av_R_equivalents   0.1930
_diffrn_reflns_av_sigmaI/netI     0.2115
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.55
_diffrn_reflns_theta_max          27.46
_reflns_number_total              4147
_reflns_number_gt                 2232
_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)+(0.1000P)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          4147
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1878
_refine_ls_R_factor_gt            0.0952
_refine_ls_wR_factor_ref          0.2270
_refine_ls_wR_factor_gt           0.1855
_refine_ls_goodness_of_fit_ref    0.985
_refine_ls_restrained_S_all       0.985
_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 0.5356(7) 0.0759(6) 0.2370(5) 0.0247(14) Uani 1 1 d . . .
C2 C 0.5228(8) 0.1241(6) 0.3516(6) 0.0290(15) Uani 1 1 d . . .
H2 H 0.4664 0.0937 0.4309 0.035 Uiso 1 1 calc R . .
C3 C 0.6069(8) 0.2229(6) 0.3281(6) 0.0323(15) Uani 1 1 d . . .
H3 H 0.6171 0.2710 0.3882 0.039 Uiso 1 1 calc R . .
C4 C 0.6738(8) 0.2385(6) 0.1995(6) 0.0340(16) Uani 1 1 d . . .
H4 H 0.7384 0.2981 0.1580 0.041 Uiso 1 1 calc R . .
C5 C 0.6282(8) 0.1498(6) 0.1430(6) 0.0283(14) Uani 1 1 d . . .
H5 H 0.6550 0.1411 0.0568 0.034 Uiso 1 1 calc R . .
C6 C 0.9727(8) -0.0925(7) 0.1635(6) 0.0338(16) Uani 1 1 d . . .
H6 H 0.9893 -0.1118 0.0810 0.041 Uiso 1 1 calc R . .
C7 C 0.8885(8) -0.1578(7) 0.2723(6) 0.0353(16) Uani 1 1 d . . .
H7 H 0.8376 -0.2263 0.2748 0.042 Uiso 1 1 calc R . .
C8 C 0.8947(8) -0.1018(7) 0.3754(6) 0.0346(16) Uani 1 1 d . . .
H8 H 0.8514 -0.1274 0.4598 0.042 Uiso 1 1 calc R . .
C9 C 0.9781(8) 0.0003(7) 0.3299(6) 0.0343(16) Uani 1 1 d . . .
H9 H 0.9978 0.0561 0.3787 0.041 Uiso 1 1 calc R . .
C10 C 1.0263(8) 0.0041(7) 0.1989(6) 0.0376(17) Uani 1 1 d . . .
H10 H 1.0849 0.0622 0.1449 0.045 Uiso 1 1 calc R . .
C11 C 0.4587(7) -0.0283(6) 0.2186(5) 0.0283(14) Uani 1 1 d . . .
H11 H 0.3489 0.0211 0.1968 0.034 Uiso 1 1 calc R . .
C12 C 0.5716(7) -0.1118(6) 0.1129(5) 0.0272(14) Uani 1 1 d . . .
H12 H 0.6258 -0.0674 0.0407 0.033 Uiso 1 1 calc R . .
C13 C 0.5991(8) -0.2437(6) 0.1155(5) 0.0293(15) Uani 1 1 d . . .
C14 C 0.3805(7) -0.2389(6) 0.3001(5) 0.0251(14) Uani 1 1 d . . .
H14 H 0.2800 -0.2046 0.2640 0.030 Uiso 1 1 calc R . .
C15 C 0.4221(8) -0.1236(6) 0.3344(5) 0.0282(14) Uani 1 1 d . . .
H15A H 0.5223 -0.1586 0.3694 0.034 Uiso 1 1 calc R . .
H15B H 0.3259 -0.0741 0.3977 0.034 Uiso 1 1 calc R . .
C16 C 0.7095(8) -0.3291(6) 0.0140(5) 0.0289(15) Uani 1 1 d . . .
C17 C 0.6953(8) -0.4549(6) 0.0083(6) 0.0329(15) Uani 1 1 d . . .
H17 H 0.6127 -0.4878 0.0691 0.039 Uiso 1 1 calc R . .
C18 C 0.8023(9) -0.5330(7) -0.0868(6) 0.0397(18) Uani 1 1 d . . .
H18 H 0.7967 -0.6208 -0.0916 0.048 Uiso 1 1 calc R . .
C19 C 0.9175(9) -0.4788(7) -0.1746(6) 0.0431(18) Uani 1 1 d . . .
H19 H 0.9922 -0.5287 -0.2417 0.052 Uiso 1 1 calc R . .
C20 C 0.9227(9) -0.3518(7) -0.1636(6) 0.0410(18) Uani 1 1 d . . .
H20 H 1.0029 -0.3164 -0.2245 0.049 Uiso 1 1 calc R . .
C21 C 0.2861(9) -0.4294(7) 0.3885(6) 0.0366(16) Uani 1 1 d . . .
H21A H 0.3754 -0.4930 0.3318 0.044 Uiso 1 1 calc R . .
H21B H 0.1880 -0.3899 0.3515 0.044 Uiso 1 1 calc R . .
C22 C 0.2341(10) -0.5022(7) 0.5116(6) 0.049(2) Uani 1 1 d . . .
H22A H 0.3329 -0.5443 0.5459 0.074 Uiso 1 1 calc R . .
H22B H 0.1871 -0.5720 0.5016 0.074 Uiso 1 1 calc R . .
H22C H 0.1484 -0.4380 0.5679 0.074 Uiso 1 1 calc R . .
N1 N 0.8208(7) -0.2747(6) -0.0716(5) 0.0382(14) Uani 1 1 d . . .
O1 O 0.5246(5) -0.3196(4) 0.2142(4) 0.0331(11) Uani 1 1 d . . .
O2 O 0.3482(5) -0.3253(4) 0.4065(4) 0.0334(11) Uani 1 1 d . . .
Fe1 Fe 0.77057(11) 0.04513(9) 0.26215(8) 0.0262(3) 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
C1 C5 1.420(8) . ?
C1 C2 1.433(8) . ?
C1 C11 1.518(9) . ?
C1 Fe1 2.040(6) . ?
C2 C3 1.400(9) . ?
C2 Fe1 2.044(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(9) . ?
C3 Fe1 2.049(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(9) . ?
C4 Fe1 2.024(6) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.029(6) . ?
C5 H5 0.9500 . ?
C6 C10 1.395(10) . ?
C6 C7 1.433(9) . ?
C6 Fe1 2.044(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(9) . ?
C7 Fe1 2.044(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.427(10) . ?
C8 Fe1 2.059(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(9) . ?
C9 Fe1 2.031(7) . ?
C9 H9 0.9500 . ?
C10 Fe1 2.037(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.512(8) . ?
C11 C15 1.536(9) . ?
C11 H11 1.0000 . ?
C12 C13 1.325(8) . ?
C12 H12 0.9500 . ?
C13 O1 1.389(7) . ?
C13 C16 1.483(8) . ?
C14 O2 1.402(7) . ?
C14 O1 1.454(7) . ?
C14 C15 1.504(8) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N1 1.353(8) . ?
C16 C17 1.379(9) . ?
C17 C18 1.387(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(10) . ?
C19 H19 0.9500 . ?
C20 N1 1.346(8) . ?
C20 H20 0.9500 . ?
C21 O2 1.428(8) . ?
C21 C22 1.499(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
 
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 106.3(5) . . ?
C5 C1 C11 126.6(5) . . ?
C2 C1 C11 127.0(5) . . ?
C5 C1 Fe1 69.2(3) . . ?
C2 C1 Fe1 69.6(3) . . ?
C11 C1 Fe1 128.0(4) . . ?
C3 C2 C1 109.1(6) . . ?
C3 C2 Fe1 70.2(4) . . ?
C1 C2 Fe1 69.3(3) . . ?
C3 C2 H2 125.5 . . ?
C1 C2 H2 125.5 . . ?
Fe1 C2 H2 126.6 . . ?
C2 C3 C4 108.0(6) . . ?
C2 C3 Fe1 69.8(4) . . ?
C4 C3 Fe1 68.8(4) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 126.9 . . ?
C3 C4 C5 108.1(6) . . ?
C3 C4 Fe1 70.7(4) . . ?
C5 C4 Fe1 69.7(4) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.2 . . ?
C1 C5 C4 108.5(5) . . ?
C1 C5 Fe1 70.0(3) . . ?
C4 C5 Fe1 69.3(4) . . ?
C1 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
Fe1 C5 H5 126.5 . . ?
C10 C6 C7 108.6(6) . . ?
C10 C6 Fe1 69.8(4) . . ?
C7 C6 Fe1 69.5(3) . . ?
C10 C6 H6 125.7 . . ?
C7 C6 H6 125.7 . . ?
Fe1 C6 H6 126.6 . . ?
C8 C7 C6 107.6(6) . . ?
C8 C7 Fe1 70.4(4) . . ?
C6 C7 Fe1 69.5(4) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
Fe1 C7 H7 125.5 . . ?
C7 C8 C9 107.6(6) . . ?
C7 C8 Fe1 69.3(4) . . ?
C9 C8 Fe1 68.6(4) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
Fe1 C8 H8 127.5 . . ?
C10 C9 C8 108.1(6) . . ?
C10 C9 Fe1 69.8(4) . . ?
C8 C9 Fe1 70.6(4) . . ?
C10 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
Fe1 C9 H9 125.3 . . ?
C6 C10 C9 108.0(6) . . ?
C6 C10 Fe1 70.3(4) . . ?
C9 C10 Fe1 69.4(4) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
C12 C11 C1 111.0(5) . . ?
C12 C11 C15 108.7(5) . . ?
C1 C11 C15 113.5(5) . . ?
C12 C11 H11 107.8 . . ?
C1 C11 H11 107.8 . . ?
C15 C11 H11 107.8 . . ?
C13 C12 C11 123.6(6) . . ?
C13 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C12 C13 O1 123.8(5) . . ?
C12 C13 C16 125.1(6) . . ?
O1 C13 C16 111.1(5) . . ?
O2 C14 O1 105.9(4) . . ?
O2 C14 C15 108.6(5) . . ?
O1 C14 C15 110.9(5) . . ?
O2 C14 H14 110.4 . . ?
O1 C14 H14 110.4 . . ?
C15 C14 H14 110.4 . . ?
C14 C15 C11 109.3(5) . . ?
C14 C15 H15A 109.8 . . ?
C11 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C11 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N1 C16 C17 123.2(5) . . ?
N1 C16 C13 115.7(6) . . ?
C17 C16 C13 121.1(6) . . ?
C18 C17 C16 119.6(6) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 117.8(6) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 119.3(6) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N1 C20 C19 123.9(6) . . ?
N1 C20 H20 118.1 . . ?
C19 C20 H20 118.1 . . ?
O2 C21 C22 108.2(5) . . ?
O2 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O2 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 N1 C16 116.3(6) . . ?
C13 O1 C14 113.7(4) . . ?
C14 O2 C21 113.5(4) . . ?
C4 Fe1 C5 41.0(3) . . ?
C4 Fe1 C9 117.9(3) . . ?
C5 Fe1 C9 151.9(3) . . ?
C4 Fe1 C10 105.6(3) . . ?
C5 Fe1 C10 117.2(3) . . ?
C9 Fe1 C10 40.9(3) . . ?
C4 Fe1 C7 163.5(3) . . ?
C5 Fe1 C7 126.7(3) . . ?
C9 Fe1 C7 68.4(3) . . ?
C10 Fe1 C7 68.5(3) . . ?
C4 Fe1 C1 69.0(3) . . ?
C5 Fe1 C1 40.8(2) . . ?
C9 Fe1 C1 166.0(2) . . ?
C10 Fe1 C1 152.1(3) . . ?
C7 Fe1 C1 108.5(3) . . ?
C4 Fe1 C6 124.8(3) . . ?
C5 Fe1 C6 106.7(2) . . ?
C9 Fe1 C6 68.0(3) . . ?
C10 Fe1 C6 40.0(3) . . ?
C7 Fe1 C6 41.0(3) . . ?
C1 Fe1 C6 119.3(2) . . ?
C4 Fe1 C2 67.9(3) . . ?
C5 Fe1 C2 68.2(2) . . ?
C9 Fe1 C2 127.9(2) . . ?
C10 Fe1 C2 164.1(3) . . ?
C7 Fe1 C2 121.7(3) . . ?
C1 Fe1 C2 41.1(2) . . ?
C6 Fe1 C2 155.6(3) . . ?
C4 Fe1 C3 40.5(3) . . ?
C5 Fe1 C3 68.3(3) . . ?
C9 Fe1 C3 108.0(3) . . ?
C10 Fe1 C3 125.8(3) . . ?
C7 Fe1 C3 155.3(3) . . ?
C1 Fe1 C3 68.7(2) . . ?
C6 Fe1 C3 162.3(3) . . ?
C2 Fe1 C3 40.0(3) . . ?
C4 Fe1 C8 153.6(3) . . ?
C5 Fe1 C8 165.0(3) . . ?
C9 Fe1 C8 40.8(3) . . ?
C10 Fe1 C8 68.5(3) . . ?
C7 Fe1 C8 40.3(3) . . ?
C1 Fe1 C8 128.2(3) . . ?
C6 Fe1 C8 68.1(2) . . ?
C2 Fe1 C8 110.4(3) . . ?
C3 Fe1 C8 121.0(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.976
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.976
_refine_diff_density_max    0.397
_refine_diff_density_min   -0.412
_refine_diff_density_rms    0.099
