 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H30 Cl2 Fe N6 O8'
_chemical_formula_weight          609.25
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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                    19.0961(8)
_cell_length_b                    8.5356(5)
_cell_length_c                    16.7145(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  115.869(4)
_cell_angle_gamma                 90.00
_cell_volume                      2451.4(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     19160
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        unknown
_exptl_crystal_colour             unknown
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.651
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1264
_exptl_absorpt_coefficient_mu     0.893
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.8777
_exptl_absorpt_correction_T_max   0.9824
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             12542
_diffrn_reflns_av_R_equivalents   0.0620
_diffrn_reflns_av_sigmaI/netI     0.0427
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.22
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2106
_reflns_number_gt                 1762
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0524P)²+9.1890P] 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        0
_refine_ls_number_reflns          2106
_refine_ls_number_parameters      168
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0601
_refine_ls_R_factor_gt            0.0468
_refine_ls_wR_factor_ref          0.1170
_refine_ls_wR_factor_gt           0.1104
_refine_ls_goodness_of_fit_ref    1.048
_refine_ls_restrained_S_all       1.048
_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
O1 O 0.55090(16) 0.2946(4) 0.08807(19) 0.0535(9) Uani 1 1 d . . .
O2 O 0.66855(15) 0.2657(3) 0.21220(18) 0.0412(7) Uani 1 1 d . . .
O3 O 0.6479(2) 0.4831(5) 0.1219(4) 0.113(2) Uani 1 1 d . . .
O4 O 0.5789(2) 0.4547(4) 0.2103(2) 0.0711(11) Uani 1 1 d . . .
Cl1 Cl 0.61285(5) 0.37897(11) 0.15769(6) 0.0347(3) Uani 1 1 d . . .
C1 C 0.37720(18) -0.0253(4) 0.0651(2) 0.0195(7) Uani 1 1 d . . .
C2 C 0.32908(19) -0.0882(4) -0.0175(2) 0.0239(8) Uani 1 1 d . . .
H5 H 0.3246 -0.1986 -0.0253 0.029 Uiso 1 1 calc R . .
C3 C 0.28776(19) 0.0097(4) -0.0884(2) 0.0262(8) Uani 1 1 d . . .
H4 H 0.2545 -0.0335 -0.1447 0.031 Uiso 1 1 calc R . .
C4 C 0.2948(2) 0.1715(5) -0.0773(2) 0.0299(9) Uani 1 1 d . . .
H3 H 0.2666 0.2387 -0.1262 0.036 Uiso 1 1 calc R . .
C5 C 0.3426(2) 0.2343(4) 0.0044(3) 0.0287(8) Uani 1 1 d . . .
H2 H 0.3475 0.3447 0.0119 0.034 Uiso 1 1 calc R . .
C6 C 0.38360(19) 0.1359(4) 0.0758(2) 0.0228(8) Uani 1 1 d . . .
C7 C 0.37003(19) -0.2075(4) 0.1727(2) 0.0228(7) Uani 1 1 d . . .
H7A H 0.3961 -0.3027 0.2064 0.027 Uiso 1 1 calc R . .
H7B H 0.3219 -0.2401 0.1207 0.027 Uiso 1 1 calc R . .
C8 C 0.47431(19) -0.2333(4) 0.1234(2) 0.0229(8) Uani 1 1 d . . .
H8A H 0.4443 -0.2884 0.0664 0.027 Uiso 1 1 calc R . .
H8B H 0.4960 -0.3128 0.1712 0.027 Uiso 1 1 calc R . .
C9 C 0.53965(19) -0.1404(4) 0.1182(2) 0.0246(8) Uani 1 1 d . . .
H9A H 0.5787 -0.2135 0.1152 0.030 Uiso 1 1 calc R . .
H9B H 0.5186 -0.0769 0.0631 0.030 Uiso 1 1 calc R . .
C10 C 0.64996(18) -0.0997(4) 0.2691(2) 0.0246(8) Uani 1 1 d . . .
H77A H 0.6828 -0.0127 0.3054 0.030 Uiso 1 1 calc R . .
H77B H 0.6801 -0.1579 0.2433 0.030 Uiso 1 1 calc R . .
N1 N 0.43465(18) 0.1949(4) 0.1618(2) 0.0338(8) Uani 1 1 d . . .
H2A H 0.4054 0.2462 0.1853 0.041 Uiso 1 1 calc R . .
H2B H 0.4677 0.2670 0.1556 0.041 Uiso 1 1 calc R . .
N2 N 0.42258(15) -0.1247(3) 0.14215(18) 0.0189(6) Uani 1 1 d . . .
N3 N 0.57811(15) -0.0351(3) 0.19637(18) 0.0212(6) Uani 1 1 d . . .
H3A H 0.5916 0.0567 0.1766 0.025 Uiso 1 1 calc R . .
Fe1 Fe 0.5000 0.02508(8) 0.2500 0.0175(2) Uani 1 2 d S . .
 
 
_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
O1 Cl1 1.439(3) . ?
O2 Cl1 1.432(3) . ?
O3 Cl1 1.394(4) . ?
O4 Cl1 1.452(4) . ?
C1 C6 1.385(5) . ?
C1 C2 1.391(5) . ?
C1 N2 1.469(4) . ?
C2 C3 1.381(5) . ?
C2 H5 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H4 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H3 0.9500 . ?
C5 C6 1.388(5) . ?
C5 H2 0.9500 . ?
C6 N1 1.432(4) . ?
C7 N2 1.488(4) . ?
C7 C10 1.505(5) 2_655 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.485(4) . ?
C8 C9 1.513(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.489(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.486(4) . ?
C10 C7 1.505(5) 2_655 ?
C10 H77A 0.9900 . ?
C10 H77B 0.9900 . ?
N1 Fe1 2.055(3) . ?
N1 H2A 0.9200 . ?
N1 H2B 0.9200 . ?
N2 Fe1 2.178(3) . ?
N3 Fe1 2.112(3) . ?
N3 H3A 0.9300 . ?
Fe1 N1 2.055(3) 2_655 ?
Fe1 N3 2.112(3) 2_655 ?
Fe1 N2 2.178(3) 2_655 ?
 
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
O3 Cl1 O2 109.9(2) . . ?
O3 Cl1 O1 110.6(3) . . ?
O2 Cl1 O1 107.27(19) . . ?
O3 Cl1 O4 113.6(3) . . ?
O2 Cl1 O4 108.6(2) . . ?
O1 Cl1 O4 106.6(2) . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 N2 118.4(3) . . ?
C2 C1 N2 121.9(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H5 120.0 . . ?
C1 C2 H5 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H4 120.0 . . ?
C4 C3 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H2 120.1 . . ?
C6 C5 H2 120.1 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 N1 117.5(3) . . ?
C5 C6 N1 122.1(3) . . ?
N2 C7 C10 109.3(3) . 2_655 ?
N2 C7 H7A 109.8 . . ?
C10 C7 H7A 109.8 2_655 . ?
N2 C7 H7B 109.8 . . ?
C10 C7 H7B 109.8 2_655 . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 109.0(3) . . ?
N2 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C8 111.7(3) . . ?
N3 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C7 110.6(3) . 2_655 ?
N3 C10 H77A 109.5 . . ?
C7 C10 H77A 109.5 2_655 . ?
N3 C10 H77B 109.5 . . ?
C7 C10 H77B 109.5 2_655 . ?
H77A C10 H77B 108.1 . . ?
C6 N1 Fe1 114.0(2) . . ?
C6 N1 H2A 108.8 . . ?
Fe1 N1 H2A 108.8 . . ?
C6 N1 H2B 108.8 . . ?
Fe1 N1 H2B 108.8 . . ?
H2A N1 H2B 107.7 . . ?
C1 N2 C8 111.6(2) . . ?
C1 N2 C7 110.3(2) . . ?
C8 N2 C7 112.7(2) . . ?
C1 N2 Fe1 108.30(19) . . ?
C8 N2 Fe1 105.52(18) . . ?
C7 N2 Fe1 108.11(19) . . ?
C10 N3 C9 114.8(3) . . ?
C10 N3 Fe1 108.3(2) . . ?
C9 N3 Fe1 110.50(19) . . ?
C10 N3 H3A 107.7 . . ?
C9 N3 H3A 107.7 . . ?
Fe1 N3 H3A 107.7 . . ?
N1 Fe1 N1 90.32(17) 2_655 . ?
N1 Fe1 N3 100.81(11) 2_655 2_655 ?
N1 Fe1 N3 98.95(11) . 2_655 ?
N1 Fe1 N3 98.95(11) 2_655 . ?
N1 Fe1 N3 100.81(11) . . ?
N3 Fe1 N3 151.84(16) 2_655 . ?
N1 Fe1 N2 171.04(11) 2_655 . ?
N1 Fe1 N2 80.80(11) . . ?
N3 Fe1 N2 81.86(10) 2_655 . ?
N3 Fe1 N2 81.72(10) . . ?
N1 Fe1 N2 80.80(11) 2_655 2_655 ?
N1 Fe1 N2 171.04(11) . 2_655 ?
N3 Fe1 N2 81.72(10) 2_655 2_655 ?
N3 Fe1 N2 81.86(10) . 2_655 ?
N2 Fe1 N2 108.10(14) . 2_655 ?
 
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
N1 H2A O4  0.92 2.42 3.168(5) 138.6 2_655
N1 H2B O1  0.92 2.33 3.092(4) 140.4 .
N1 H2B O4  0.92 2.49 3.350(5) 154.9 .
N3 H3A O2  0.93 2.22 3.041(4) 146.6 .
N3 H3A O1  0.93 2.43 3.263(5) 148.8 .
N3 H3A Cl1  0.93 2.82 3.705(3) 159.7 .
 
_diffrn_measured_fraction_theta_max    0.970
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.970
_refine_diff_density_max    0.695
_refine_diff_density_min   -0.615
_refine_diff_density_rms    0.090
