 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C24 H15 Cl Fe O2'
_chemical_formula_sum
 'C24 H15 Cl Fe O2'
_chemical_formula_weight          426.66
 
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'
 'O'  'O'   0.0106   0.0060
 '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'
 'Fe'  'Fe'   0.3463   0.8444
 '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
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    7.594(3)
_cell_length_b                    15.1770(12)
_cell_length_c                    31.134(16)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3588(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        lathe
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.70
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.580
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1744
_exptl_absorpt_coefficient_mu     1.007
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5390
_exptl_absorpt_correction_T_max   0.9514
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             10947
_diffrn_reflns_av_R_equivalents   0.1750
_diffrn_reflns_av_sigmaI/netI     1.1669
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -34
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          2.62
_diffrn_reflns_theta_max          25.05
_reflns_number_total              2747
_reflns_number_gt                 428
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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)+(0.0176P)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          2747
_refine_ls_number_parameters      253
_refine_ls_number_restraints      12
_refine_ls_R_factor_all           0.3233
_refine_ls_R_factor_gt            0.0375
_refine_ls_wR_factor_ref          0.1030
_refine_ls_wR_factor_gt           0.0572
_refine_ls_goodness_of_fit_ref    0.465
_refine_ls_restrained_S_all       0.465
_refine_ls_shift/su_max           0.007
_refine_ls_shift/su_mean          0.001
 
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 0.19508(19) 0.36871(10) 0.43336(6) 0.0723(6) Uani 1 1 d . . .
Cl1 Cl 0.2039(4) 0.1120(3) 0.07069(13) 0.1412(14) Uani 1 1 d . . .
O1 O 0.2721(10) 0.0647(5) 0.2830(3) 0.092(3) Uani 1 1 d . . .
O2 O 0.0476(10) 0.3399(5) 0.1891(3) 0.092(3) Uani 1 1 d . . .
C1 C 0.4515(14) 0.3959(11) 0.4292(9) 0.106(7) Uani 1 1 d . . .
H1 H 0.5398 0.3540 0.4258 0.127 Uiso 1 1 calc R . .
C2 C 0.359(3) 0.4362(14) 0.3953(7) 0.121(8) Uani 1 1 d . . .
H2 H 0.3786 0.4277 0.3661 0.145 Uiso 1 1 calc R . .
C3 C 0.228(3) 0.4939(13) 0.4147(9) 0.145(10) Uani 1 1 d . . .
H3 H 0.1390 0.5261 0.4013 0.173 Uiso 1 1 calc R . .
C4 C 0.267(3) 0.4887(13) 0.4571(9) 0.139(10) Uani 1 1 d . . .
H4 H 0.2133 0.5238 0.4778 0.166 Uiso 1 1 calc R . .
C5 C 0.395(3) 0.4262(14) 0.4669(5) 0.103(6) Uani 1 1 d . . .
H5 H 0.4324 0.4091 0.4941 0.124 Uiso 1 1 calc R . .
C6 C 0.1638(15) 0.2376(8) 0.4235(5) 0.075(5) Uani 1 1 d . . .
H6 H 0.2561 0.2001 0.4163 0.090 Uiso 1 1 calc R . .
C7 C 0.1060(16) 0.2584(8) 0.4663(5) 0.077(5) Uani 1 1 d . . .
H7 H 0.1472 0.2329 0.4915 0.093 Uiso 1 1 calc R . .
C8 C -0.0208(15) 0.3227(8) 0.4633(5) 0.072(4) Uani 1 1 d . . .
H8 H -0.0756 0.3502 0.4863 0.087 Uiso 1 1 calc R . .
C9 C -0.0545(13) 0.3402(7) 0.4194(4) 0.064(4) Uani 1 1 d . . .
H9 H -0.1346 0.3812 0.4088 0.077 Uiso 1 1 calc R . .
C10 C 0.0561(14) 0.2840(8) 0.3941(6) 0.072(5) Uani 1 1 d U . .
C11 C 0.0773(15) 0.2806(10) 0.3470(5) 0.057(4) Uani 1 1 d . . .
C12 C 0.0177(13) 0.3530(9) 0.3231(5) 0.069(5) Uani 1 1 d . . .
H12 H -0.0282 0.4022 0.3369 0.083 Uiso 1 1 calc R . .
C13 C 0.0279(13) 0.3501(9) 0.2795(5) 0.072(5) Uani 1 1 d . . .
H13 H -0.0055 0.3995 0.2637 0.087 Uiso 1 1 calc R . .
C14 C 0.0872(13) 0.2750(9) 0.2574(5) 0.053(4) Uani 1 1 d . . .
C15 C 0.1458(14) 0.2056(9) 0.2812(5) 0.059(5) Uani 1 1 d . . .
C16 C 0.1368(13) 0.2089(8) 0.3249(5) 0.058(4) Uani 1 1 d . . .
H16 H 0.1731 0.1599 0.3404 0.070 Uiso 1 1 calc R . .
C17 C 0.2211(13) 0.1268(9) 0.2603(4) 0.060(3) Uani 1 1 d . . .
C18 C 0.2127(16) 0.1265(12) 0.2120(5) 0.065(3) Uani 1 1 d . . .
C19 C 0.1487(12) 0.1969(8) 0.1880(5) 0.039(3) Uani 1 1 d U . .
C20 C 0.0905(13) 0.2794(10) 0.2116(4) 0.048(4) Uani 1 1 d . . .
C21 C 0.1514(15) 0.1891(10) 0.1446(5) 0.078(5) Uani 1 1 d . . .
H21 H 0.1096 0.2350 0.1277 0.094 Uiso 1 1 calc R . .
C22 C 0.214(2) 0.1158(14) 0.1258(4) 0.087(5) Uani 1 1 d . . .
C23 C 0.2791(16) 0.0489(9) 0.1516(6) 0.081(6) Uani 1 1 d . . .
H23 H 0.3277 0.0001 0.1380 0.097 Uiso 1 1 calc R . .
C24 C 0.2777(16) 0.0491(10) 0.1949(6) 0.085(5) Uani 1 1 d . . .
H24 H 0.3164 0.0021 0.2115 0.102 Uiso 1 1 calc R . .
 
 
_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
Fe1 C9 1.992(10) . ?
Fe1 C1 1.995(11) . ?
Fe1 C2 2.002(15) . ?
Fe1 C8 2.010(11) . ?
Fe1 C3 2.002(18) . ?
Fe1 C4 2.039(17) . ?
Fe1 C6 2.027(11) . ?
Fe1 C5 2.037(12) . ?
Fe1 C10 2.064(14) . ?
Fe1 C7 2.076(11) . ?
Cl1 C22 1.718(11) . ?
O1 C17 1.240(12) . ?
O2 C20 1.200(12) . ?
C1 C5 1.332(16) . ?
C1 C2 1.41(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.46(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.36(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(18) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C10 1.413(15) . ?
C6 C7 1.438(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.433(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.478(17) . ?
C11 C16 1.364(14) . ?
C11 C12 1.401(16) . ?
C12 C13 1.362(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(15) . ?
C14 C20 1.428(15) . ?
C15 C16 1.361(15) . ?
C15 C17 1.476(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.505(14) . ?
C18 C24 1.381(17) . ?
C18 C19 1.392(16) . ?
C19 C21 1.355(15) . ?
C19 C20 1.517(15) . ?
C21 C22 1.343(18) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(18) . ?
C23 C24 1.347(17) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
 
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
C9 Fe1 C1 163.7(9) . . ?
C9 Fe1 C2 125.1(8) . . ?
C1 Fe1 C2 41.2(6) . . ?
C9 Fe1 C8 41.4(4) . . ?
C1 Fe1 C8 153.9(9) . . ?
C2 Fe1 C8 163.7(9) . . ?
C9 Fe1 C3 105.0(7) . . ?
C1 Fe1 C3 70.4(8) . . ?
C2 Fe1 C3 42.7(7) . . ?
C8 Fe1 C3 124.4(9) . . ?
C9 Fe1 C4 121.8(7) . . ?
C1 Fe1 C4 65.0(7) . . ?
C2 Fe1 C4 65.8(9) . . ?
C8 Fe1 C4 111.2(8) . . ?
C3 Fe1 C4 39.2(6) . . ?
C9 Fe1 C6 69.0(4) . . ?
C1 Fe1 C6 107.9(6) . . ?
C2 Fe1 C6 119.0(8) . . ?
C8 Fe1 C6 68.5(5) . . ?
C3 Fe1 C6 154.3(9) . . ?
C4 Fe1 C6 164.3(9) . . ?
C9 Fe1 C5 155.9(8) . . ?
C1 Fe1 C5 38.6(4) . . ?
C2 Fe1 C5 67.7(7) . . ?
C8 Fe1 C5 121.2(7) . . ?
C3 Fe1 C5 69.6(7) . . ?
C4 Fe1 C5 39.9(5) . . ?
C6 Fe1 C5 125.9(8) . . ?
C9 Fe1 C10 41.3(4) . . ?
C1 Fe1 C10 126.2(7) . . ?
C2 Fe1 C10 106.7(8) . . ?
C8 Fe1 C10 68.9(6) . . ?
C3 Fe1 C10 118.8(9) . . ?
C4 Fe1 C10 155.2(8) . . ?
C6 Fe1 C10 40.4(4) . . ?
C5 Fe1 C10 162.0(8) . . ?
C9 Fe1 C7 67.8(5) . . ?
C1 Fe1 C7 121.1(8) . . ?
C2 Fe1 C7 155.2(8) . . ?
C8 Fe1 C7 39.3(4) . . ?
C3 Fe1 C7 161.6(10) . . ?
C4 Fe1 C7 128.9(9) . . ?
C6 Fe1 C7 41.0(5) . . ?
C5 Fe1 C7 109.6(6) . . ?
C10 Fe1 C7 67.9(6) . . ?
C5 C1 C2 110.4(17) . . ?
C5 C1 Fe1 72.4(8) . . ?
C2 C1 Fe1 69.7(8) . . ?
C5 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
Fe1 C1 H1 124.7 . . ?
C1 C2 C3 107(2) . . ?
C1 C2 Fe1 69.1(10) . . ?
C3 C2 Fe1 68.6(10) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
Fe1 C2 H2 127.3 . . ?
C4 C3 C2 102(3) . . ?
C4 C3 Fe1 71.9(14) . . ?
C2 C3 Fe1 68.6(11) . . ?
C4 C3 H3 128.8 . . ?
C2 C3 H3 128.8 . . ?
Fe1 C3 H3 122.7 . . ?
C3 C4 C5 114(3) . . ?
C3 C4 Fe1 68.9(12) . . ?
C5 C4 Fe1 70.0(10) . . ?
C3 C4 H4 123.0 . . ?
C5 C4 H4 123.0 . . ?
Fe1 C4 H4 130.2 . . ?
C1 C5 C4 105.6(18) . . ?
C1 C5 Fe1 69.0(8) . . ?
C4 C5 Fe1 70.2(9) . . ?
C1 C5 H5 127.2 . . ?
C4 C5 H5 127.2 . . ?
Fe1 C5 H5 125.2 . . ?
C10 C6 C7 108.3(13) . . ?
C10 C6 Fe1 71.2(8) . . ?
C7 C6 Fe1 71.3(7) . . ?
C10 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
Fe1 C6 H6 123.3 . . ?
C8 C7 C6 107.8(13) . . ?
C8 C7 Fe1 67.8(7) . . ?
C6 C7 Fe1 67.7(7) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 130.0 . . ?
C7 C8 C9 109.1(14) . . ?
C7 C8 Fe1 73.0(7) . . ?
C9 C8 Fe1 68.6(7) . . ?
C7 C8 H8 125.5 . . ?
C9 C8 H8 125.5 . . ?
Fe1 C8 H8 124.5 . . ?
C8 C9 C10 108.1(13) . . ?
C8 C9 Fe1 70.0(7) . . ?
C10 C9 Fe1 72.0(7) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 123.7 . . ?
C6 C10 C9 106.3(15) . . ?
C6 C10 C11 124.1(13) . . ?
C9 C10 C11 129.1(15) . . ?
C6 C10 Fe1 68.4(8) . . ?
C9 C10 Fe1 66.7(7) . . ?
C11 C10 Fe1 123.6(9) . . ?
C16 C11 C12 117.7(15) . . ?
C16 C11 C10 124.4(16) . . ?
C12 C11 C10 117.6(16) . . ?
C13 C12 C11 119.1(15) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 122.2(15) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 117.6(15) . . ?
C15 C14 C20 125.1(14) . . ?
C13 C14 C20 117.1(15) . . ?
C16 C15 C14 120.0(15) . . ?
C16 C15 C17 119.3(14) . . ?
C14 C15 C17 120.7(15) . . ?
C15 C16 C11 123.4(15) . . ?
C15 C16 H16 118.3 . . ?
C11 C16 H16 118.3 . . ?
O1 C17 C15 119.1(12) . . ?
O1 C17 C18 125.4(15) . . ?
C15 C17 C18 115.2(15) . . ?
C24 C18 C19 124.7(14) . . ?
C24 C18 C17 111.9(17) . . ?
C19 C18 C17 123.4(17) . . ?
C21 C19 C18 117.6(13) . . ?
C21 C19 C20 124.0(16) . . ?
C18 C19 C20 118.3(14) . . ?
O2 C20 C14 127.9(15) . . ?
O2 C20 C19 115.4(14) . . ?
C14 C20 C19 116.7(13) . . ?
C22 C21 C19 120.8(15) . . ?
C22 C21 H21 119.6 . . ?
C19 C21 H21 119.6 . . ?
C21 C22 C23 118.7(13) . . ?
C21 C22 Cl1 116.6(16) . . ?
C23 C22 Cl1 124.7(18) . . ?
C24 C23 C22 125.1(18) . . ?
C24 C23 H23 117.5 . . ?
C22 C23 H23 117.5 . . ?
C23 C24 C18 113.1(18) . . ?
C23 C24 H24 123.5 . . ?
C18 C24 H24 123.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.867
_diffrn_reflns_theta_full              25.05
_diffrn_measured_fraction_theta_full   0.867
_refine_diff_density_max    0.152
_refine_diff_density_min   -0.166
_refine_diff_density_rms    0.041
