 
data_platon
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H17 Fe N O'
_chemical_formula_weight          343.20
 
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'
 'Fe'  'Fe'   0.3463   0.8444
 '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    Pbca
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    17.4825(5)
_cell_length_b                    7.3420(2)
_cell_length_c                    23.1152(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2966.99(15)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     21471
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.537
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1424
_exptl_absorpt_coefficient_mu     1.020
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7774
_exptl_absorpt_correction_T_max   0.9899
_exptl_absorpt_process_details      'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             22133
_diffrn_reflns_av_R_equivalents   0.1137
_diffrn_reflns_av_sigmaI/netI     0.0806
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3408
_reflns_number_gt                 2262
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0000P)²+24.7555P] 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          3408
_refine_ls_number_parameters      209
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1399
_refine_ls_R_factor_gt            0.0871
_refine_ls_wR_factor_ref          0.1661
_refine_ls_wR_factor_gt           0.1426
_refine_ls_goodness_of_fit_ref    1.153
_refine_ls_restrained_S_all       1.153
_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 0.3233(3) 0.1128(9) 0.6511(2) 0.0210(13) Uani 1 1 d . . .
H1A H 0.3783 0.1013 0.6585 0.032 Uiso 1 1 calc R . .
H1B H 0.2985 -0.0053 0.6572 0.032 Uiso 1 1 calc R . .
H1C H 0.3014 0.2029 0.6776 0.032 Uiso 1 1 calc R . .
C2 C 0.2392(3) 0.1926(7) 0.5668(2) 0.0137(11) Uani 1 1 d . . .
C3 C 0.1682(3) 0.1579(8) 0.5905(2) 0.0186(12) Uani 1 1 d . . .
H3 H 0.1636 0.1063 0.6280 0.022 Uiso 1 1 calc R . .
C4 C 0.1035(3) 0.2004(8) 0.5579(2) 0.0195(13) Uani 1 1 d . . .
H4 H 0.0542 0.1749 0.5731 0.023 Uiso 1 1 calc R . .
C5 C 0.1102(3) 0.2797(8) 0.5035(2) 0.0211(13) Uani 1 1 d . . .
H5 H 0.0655 0.3118 0.4825 0.025 Uiso 1 1 calc R . .
C6 C 0.1827(3) 0.3122(8) 0.4797(3) 0.0179(12) Uani 1 1 d . . .
H6 H 0.1872 0.3669 0.4426 0.021 Uiso 1 1 calc R . .
C7 C 0.2475(3) 0.2646(8) 0.5103(2) 0.0146(11) Uani 1 1 d . . .
C8 C 0.3303(3) 0.2864(7) 0.5005(2) 0.0136(11) Uani 1 1 d . . .
C9 C 0.3682(3) 0.2336(8) 0.5561(2) 0.0161(11) Uani 1 1 d . . .
C10 C 0.3741(3) 0.3423(7) 0.4565(2) 0.0159(12) Uani 1 1 d . . .
H10 H 0.4270 0.3556 0.4650 0.019 Uiso 1 1 calc R . .
C11 C 0.3520(3) 0.3852(7) 0.3976(2) 0.0133(11) Uani 1 1 d . . .
C12 C 0.2918(3) 0.3096(8) 0.3639(2) 0.0148(11) Uani 1 1 d . . .
H12 H 0.2560 0.2211 0.3768 0.018 Uiso 1 1 calc R . .
C13 C 0.2941(3) 0.3890(8) 0.3076(2) 0.0177(12) Uani 1 1 d . . .
H13 H 0.2598 0.3631 0.2768 0.021 Uiso 1 1 calc R . .
C14 C 0.3561(3) 0.5125(8) 0.3053(3) 0.0204(13) Uani 1 1 d . . .
H14 H 0.3703 0.5849 0.2730 0.024 Uiso 1 1 calc R . .
C15 C 0.3933(3) 0.5094(7) 0.3597(2) 0.0178(12) Uani 1 1 d . . .
H15 H 0.4377 0.5769 0.3698 0.021 Uiso 1 1 calc R . .
C16 C 0.4047(3) -0.0214(7) 0.3216(3) 0.0173(12) Uani 1 1 d . . .
H16 H 0.3702 -0.1071 0.3378 0.021 Uiso 1 1 calc R . .
C17 C 0.4012(3) 0.0513(8) 0.2648(2) 0.0187(12) Uani 1 1 d . . .
H17 H 0.3641 0.0219 0.2363 0.022 Uiso 1 1 calc R . .
C18 C 0.4630(3) 0.1759(8) 0.2579(2) 0.0180(12) Uani 1 1 d . . .
H18 H 0.4741 0.2444 0.2241 0.022 Uiso 1 1 calc R . .
C19 C 0.5050(3) 0.1794(8) 0.3105(2) 0.0180(12) Uani 1 1 d . . .
H19 H 0.5491 0.2511 0.3180 0.022 Uiso 1 1 calc R . .
C20 C 0.4695(3) 0.0570(8) 0.3501(3) 0.0182(12) Uani 1 1 d . . .
H20 H 0.4859 0.0320 0.3885 0.022 Uiso 1 1 calc R . .
Fe1 Fe 0.39369(4) 0.25555(11) 0.32464(3) 0.01278(19) Uani 1 1 d . . .
N1 N 0.3113(3) 0.1711(7) 0.59216(19) 0.0160(10) Uani 1 1 d . . .
O9 O 0.4362(2) 0.2381(6) 0.56874(17) 0.0204(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 N1 1.443(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.380(8) . ?
C2 N1 1.399(7) . ?
C2 C7 1.416(7) . ?
C3 C4 1.395(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.474(7) . ?
C8 C10 1.337(8) . ?
C8 C9 1.499(7) . ?
C9 O9 1.224(6) . ?
C9 N1 1.376(7) . ?
C10 C11 1.450(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.423(8) . ?
C11 C15 1.456(7) . ?
C11 Fe1 2.069(5) . ?
C12 C13 1.426(8) . ?
C12 Fe1 2.039(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(8) . ?
C13 Fe1 2.036(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(8) . ?
C14 Fe1 2.047(6) . ?
C14 H14 0.9500 . ?
C15 Fe1 2.033(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.418(8) . ?
C16 C20 1.432(8) . ?
C16 Fe1 2.044(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.424(8) . ?
C17 Fe1 2.045(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.421(8) . ?
C18 Fe1 2.048(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.425(8) . ?
C19 Fe1 2.051(5) . ?
C19 H19 0.9500 . ?
C20 Fe1 2.056(6) . ?
C20 H20 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 128.5(5) . . ?
C3 C2 C7 121.8(5) . . ?
N1 C2 C7 109.7(5) . . ?
C2 C3 C4 118.3(5) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 118.9(5) . . ?
C6 C7 C8 134.3(5) . . ?
C2 C7 C8 106.5(5) . . ?
C10 C8 C7 135.6(5) . . ?
C10 C8 C9 118.6(5) . . ?
C7 C8 C9 105.9(4) . . ?
O9 C9 N1 124.6(5) . . ?
O9 C9 C8 128.8(5) . . ?
N1 C9 C8 106.6(4) . . ?
C8 C10 C11 128.8(5) . . ?
C8 C10 H10 115.6 . . ?
C11 C10 H10 115.6 . . ?
C12 C11 C10 128.8(5) . . ?
C12 C11 C15 106.4(5) . . ?
C10 C11 C15 124.7(5) . . ?
C12 C11 Fe1 68.6(3) . . ?
C10 C11 Fe1 124.9(4) . . ?
C15 C11 Fe1 67.9(3) . . ?
C11 C12 C13 108.6(5) . . ?
C11 C12 Fe1 70.9(3) . . ?
C13 C12 Fe1 69.4(3) . . ?
C11 C12 H12 125.7 . . ?
C13 C12 H12 125.7 . . ?
Fe1 C12 H12 125.6 . . ?
C14 C13 C12 108.6(5) . . ?
C14 C13 Fe1 70.2(3) . . ?
C12 C13 Fe1 69.6(3) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
Fe1 C13 H13 126.1 . . ?
C13 C14 C15 107.9(5) . . ?
C13 C14 Fe1 69.3(3) . . ?
C15 C14 Fe1 69.1(3) . . ?
C13 C14 H14 126.0 . . ?
C15 C14 H14 126.0 . . ?
Fe1 C14 H14 127.1 . . ?
C14 C15 C11 108.5(5) . . ?
C14 C15 Fe1 70.2(3) . . ?
C11 C15 Fe1 70.6(3) . . ?
C14 C15 H15 125.8 . . ?
C11 C15 H15 125.8 . . ?
Fe1 C15 H15 125.0 . . ?
C17 C16 C20 108.0(5) . . ?
C17 C16 Fe1 69.7(3) . . ?
C20 C16 Fe1 70.0(3) . . ?
C17 C16 H16 126.0 . . ?
C20 C16 H16 126.0 . . ?
Fe1 C16 H16 125.8 . . ?
C16 C17 C18 108.2(5) . . ?
C16 C17 Fe1 69.7(3) . . ?
C18 C17 Fe1 69.7(3) . . ?
C16 C17 H17 125.9 . . ?
C18 C17 H17 125.9 . . ?
Fe1 C17 H17 126.3 . . ?
C19 C18 C17 107.9(5) . . ?
C19 C18 Fe1 69.8(3) . . ?
C17 C18 Fe1 69.5(3) . . ?
C19 C18 H18 126.0 . . ?
C17 C18 H18 126.0 . . ?
Fe1 C18 H18 126.2 . . ?
C18 C19 C20 108.3(5) . . ?
C18 C19 Fe1 69.6(3) . . ?
C20 C19 Fe1 69.9(3) . . ?
C18 C19 H19 125.9 . . ?
C20 C19 H19 125.9 . . ?
Fe1 C19 H19 126.2 . . ?
C19 C20 C16 107.6(5) . . ?
C19 C20 Fe1 69.5(3) . . ?
C16 C20 Fe1 69.1(3) . . ?
C19 C20 H20 126.2 . . ?
C16 C20 H20 126.2 . . ?
Fe1 C20 H20 126.8 . . ?
C15 Fe1 C13 68.5(2) . . ?
C15 Fe1 C12 68.9(2) . . ?
C13 Fe1 C12 41.0(2) . . ?
C15 Fe1 C16 157.9(2) . . ?
C13 Fe1 C16 123.6(2) . . ?
C12 Fe1 C16 107.0(2) . . ?
C15 Fe1 C17 160.5(2) . . ?
C13 Fe1 C17 106.1(2) . . ?
C12 Fe1 C17 120.0(2) . . ?
C16 Fe1 C17 40.6(2) . . ?
C15 Fe1 C14 40.6(2) . . ?
C13 Fe1 C14 40.5(2) . . ?
C12 Fe1 C14 68.7(2) . . ?
C16 Fe1 C14 160.0(2) . . ?
C17 Fe1 C14 123.3(2) . . ?
C15 Fe1 C18 124.4(2) . . ?
C13 Fe1 C18 119.9(2) . . ?
C12 Fe1 C18 155.3(2) . . ?
C16 Fe1 C18 68.5(2) . . ?
C17 Fe1 C18 40.7(2) . . ?
C14 Fe1 C18 106.8(2) . . ?
C15 Fe1 C19 108.5(2) . . ?
C13 Fe1 C19 155.7(2) . . ?
C12 Fe1 C19 162.4(2) . . ?
C16 Fe1 C19 68.5(2) . . ?
C17 Fe1 C19 68.3(2) . . ?
C14 Fe1 C19 121.4(2) . . ?
C18 Fe1 C19 40.6(2) . . ?
C15 Fe1 C20 122.5(2) . . ?
C13 Fe1 C20 161.4(2) . . ?
C12 Fe1 C20 125.0(2) . . ?
C16 Fe1 C20 40.9(2) . . ?
C17 Fe1 C20 68.4(2) . . ?
C14 Fe1 C20 157.3(2) . . ?
C18 Fe1 C20 68.4(2) . . ?
C19 Fe1 C20 40.6(2) . . ?
C15 Fe1 C11 41.6(2) . . ?
C13 Fe1 C11 68.6(2) . . ?
C12 Fe1 C11 40.5(2) . . ?
C16 Fe1 C11 121.3(2) . . ?
C17 Fe1 C11 155.7(2) . . ?
C14 Fe1 C11 69.0(2) . . ?
C18 Fe1 C11 162.6(2) . . ?
C19 Fe1 C11 126.1(2) . . ?
C20 Fe1 C11 108.6(2) . . ?
C9 N1 C2 111.1(4) . . ?
C9 N1 C1 124.3(5) . . ?
C2 N1 C1 124.1(5) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.599
_refine_diff_density_min   -0.596
_refine_diff_density_rms    0.133
