data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. Craig Matthews
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C11 H11 Fe N3 O7, N O3 '
_chemical_formula_sum
 'C11 H11 Fe N4 O10'
_chemical_formula_weight          415.09
 
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    C2/c
_symmetry_space_group_name_hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    12.463(5)
_cell_length_b                    10.797(1)
_cell_length_c                    22.201(5)
_cell_angle_alpha                 90.000
_cell_angle_beta                  91.765(2)
_cell_angle_gamma                 90.000
_cell_volume                      2986.0(14)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5382
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Shard
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.847
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1688
_exptl_absorpt_coefficient_mu     1.079
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8998
_exptl_absorpt_correction_T_max   0.9480
_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             18064
_diffrn_reflns_av_R_equivalents   0.1110
_diffrn_reflns_av_sigmaI/netI     0.0689
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_theta_min          3.07
_diffrn_reflns_theta_max          27.44
_reflns_number_total              3398
_reflns_number_gt                 2463
_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)+(0.0606P)²+6.6230P] 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          3398
_refine_ls_number_parameters      251
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0815
_refine_ls_R_factor_gt            0.0516
_refine_ls_wR_factor_ref          0.1389
_refine_ls_wR_factor_gt           0.1240
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.031
_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 0.1225(3) 0.2145(3) 0.02587(16) 0.0248(7) Uani 1 1 d . . .
H1 H 0.1158 0.2951 0.0426 0.030 Uiso 1 1 calc R . .
C2 C 0.1245(3) 0.2032(3) -0.03582(16) 0.0273(8) Uani 1 1 d . . .
H2 H 0.1190 0.2744 -0.0609 0.033 Uiso 1 1 calc R . .
C3 C 0.1348(3) 0.0869(3) -0.06062(16) 0.0304(8) Uani 1 1 d . . .
H3 H 0.1376 0.0767 -0.1031 0.037 Uiso 1 1 calc R . .
C4 C 0.1409(3) -0.0142(3) -0.02301(15) 0.0264(8) Uani 1 1 d . . .
H4 H 0.1469 -0.0952 -0.0393 0.032 Uiso 1 1 calc R . .
C5 C 0.1382(3) 0.0030(3) 0.03865(15) 0.0228(7) Uani 1 1 d . . .
C6 C 0.1417(3) -0.0992(3) 0.08244(15) 0.0240(7) Uani 1 1 d . . .
C7 C 0.1426(3) -0.2251(3) 0.06827(16) 0.0276(8) Uani 1 1 d . . .
H7 H 0.1436 -0.2517 0.0275 0.033 Uiso 1 1 calc R . .
C8 C 0.1418(3) -0.3100(3) 0.11448(17) 0.0318(9) Uani 1 1 d . . .
H8 H 0.1427 -0.3961 0.1056 0.038 Uiso 1 1 calc R . .
C9 C 0.1398(3) -0.2709(3) 0.17374(16) 0.0299(9) Uani 1 1 d . . .
H9 H 0.1398 -0.3288 0.2059 0.036 Uiso 1 1 calc R . .
C10 C 0.1378(3) -0.1446(3) 0.18472(16) 0.0243(7) Uani 1 1 d . . .
C11 C 0.1282(3) -0.0866(3) 0.24563(15) 0.0237(7) Uani 1 1 d . . .
N1 N 0.1294(2) 0.1174(2) 0.06367(12) 0.0223(6) Uani 1 1 d . . .
N2 N 0.1395(2) -0.0621(2) 0.13986(12) 0.0219(6) Uani 1 1 d . . .
O1 O 0.1225(2) 0.03261(19) 0.24396(10) 0.0243(5) Uani 1 1 d . . .
O2 O 0.1240(2) -0.1493(2) 0.29164(10) 0.0270(6) Uani 1 1 d . . .
O11 O -0.0279(2) 0.1326(2) 0.15840(11) 0.0245(5) Uani 1 1 d D . .
O12 O 0.2932(2) 0.1371(2) 0.16681(11) 0.0248(5) Uani 1 1 d D . .
Fe1 Fe 0.13276(4) 0.12795(4) 0.16360(2) 0.02161(17) Uani 1 1 d . . .
H11A H -0.067(3) 0.117(3) 0.1874(13) 0.053(15) Uiso 1 1 d D . .
H11B H -0.057(3) 0.190(2) 0.1382(13) 0.031(11) Uiso 1 1 d D . .
H12A H 0.341(2) 0.083(3) 0.1654(19) 0.057(15) Uiso 1 1 d D . .
H12B H 0.318(3) 0.197(2) 0.1867(17) 0.054(14) Uiso 1 1 d D . .
N21 N 0.1332(3) 0.3552(2) 0.19734(13) 0.0274(7) Uani 1 1 d . . .
O21 O 0.1341(2) 0.2640(2) 0.23385(11) 0.0276(6) Uani 1 1 d . . .
O22 O 0.1337(2) 0.3230(2) 0.14199(11) 0.0275(6) Uani 1 1 d . . .
O23 O 0.1315(2) 0.4614(2) 0.21373(12) 0.0364(7) Uani 1 1 d . . .
N31 N 0.3974(3) -0.0927(3) 0.09102(14) 0.0301(7) Uani 1 1 d . . .
O31 O 0.3843(3) -0.0152(2) 0.05055(13) 0.0454(8) Uani 1 1 d . . .
O32 O 0.4037(2) -0.0626(2) 0.14568(12) 0.0394(7) Uani 1 1 d . . .
O33 O 0.4035(2) -0.2065(2) 0.07763(12) 0.0345(6) 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 N1 1.345(4) . ?
C1 C2 1.376(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.360(4) . ?
C5 C6 1.470(5) . ?
C6 N2 1.337(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.337(4) . ?
C10 C11 1.499(5) . ?
C11 O2 1.228(4) . ?
C11 O1 1.289(4) . ?
N1 Fe1 2.221(3) . ?
N2 Fe1 2.121(3) . ?
O1 Fe1 2.067(2) . ?
O11 Fe1 2.003(3) . ?
O11 H11A 0.834(10) . ?
O11 H11B 0.836(10) . ?
O12 Fe1 2.001(3) . ?
O12 H12A 0.835(10) . ?
O12 H12B 0.834(10) . ?
Fe1 O21 2.142(2) . ?
Fe1 O22 2.160(2) . ?
N21 O23 1.204(3) . ?
N21 O21 1.275(3) . ?
N21 O22 1.277(4) . ?
N31 O31 1.235(4) . ?
N31 O32 1.256(4) . ?
N31 O33 1.268(4) . ?
 
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 C2 123.3(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 114.4(3) . . ?
C4 C5 C6 123.6(3) . . ?
N2 C6 C7 120.5(3) . . ?
N2 C6 C5 113.8(3) . . ?
C7 C6 C5 125.6(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 118.0(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
N2 C10 C9 121.6(3) . . ?
N2 C10 C11 113.4(3) . . ?
C9 C10 C11 124.9(3) . . ?
O2 C11 O1 124.8(3) . . ?
O2 C11 C10 121.8(3) . . ?
O1 C11 C10 113.4(3) . . ?
C1 N1 C5 117.3(3) . . ?
C1 N1 Fe1 125.6(2) . . ?
C5 N1 Fe1 117.1(2) . . ?
C10 N2 C6 120.8(3) . . ?
C10 N2 Fe1 117.3(2) . . ?
C6 N2 Fe1 121.9(2) . . ?
C11 O1 Fe1 121.1(2) . . ?
Fe1 O11 H11A 124(3) . . ?
Fe1 O11 H11B 117(2) . . ?
H11A O11 H11B 108.1(17) . . ?
Fe1 O12 H12A 133(3) . . ?
Fe1 O12 H12B 114(3) . . ?
H12A O12 H12B 108.1(17) . . ?
O12 Fe1 O11 175.54(9) . . ?
O12 Fe1 O1 94.70(10) . . ?
O11 Fe1 O1 88.52(10) . . ?
O12 Fe1 N2 90.55(10) . . ?
O11 Fe1 N2 93.27(10) . . ?
O1 Fe1 N2 74.73(10) . . ?
O12 Fe1 O21 87.39(10) . . ?
O11 Fe1 O21 90.59(10) . . ?
O1 Fe1 O21 73.29(9) . . ?
N2 Fe1 O21 147.66(10) . . ?
O12 Fe1 O22 86.98(10) . . ?
O11 Fe1 O22 88.57(9) . . ?
O1 Fe1 O22 132.69(9) . . ?
N2 Fe1 O22 152.57(10) . . ?
O21 Fe1 O22 59.54(9) . . ?
O12 Fe1 N1 91.49(10) . . ?
O11 Fe1 N1 87.47(11) . . ?
O1 Fe1 N1 146.82(9) . . ?
N2 Fe1 N1 72.64(10) . . ?
O21 Fe1 N1 139.65(9) . . ?
O22 Fe1 N1 80.12(9) . . ?
O23 N21 O21 122.9(3) . . ?
O23 N21 O22 123.4(3) . . ?
O21 N21 O22 113.7(2) . . ?
N21 O21 Fe1 93.84(18) . . ?
N21 O22 Fe1 92.93(17) . . ?
O31 N31 O32 122.1(3) . . ?
O31 N31 O33 119.6(3) . . ?
O32 N31 O33 118.4(3) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O11 H11A O1  0.834(10) 1.925(14) 2.723(3) 160(3) 2
O11 H11B O33  0.836(10) 1.808(13) 2.621(4) 164(3) 3_455
O12 H12A O32  0.835(10) 1.816(15) 2.609(4) 158(4) .
O12 H12B O2  0.834(10) 1.870(16) 2.679(3) 163(4) 4
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.44
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.538
_refine_diff_density_min   -0.706
_refine_diff_density_rms    0.095
