 
data_2007src0831
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
   Dr P. J. Taylor 
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H20 Cl Fe N O3'
_chemical_formula_weight          377.64
 
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    'P 2(1)/n'

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    7.8204(2)
_cell_length_b                    19.1689(6)
_cell_length_c                    11.3839(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  100.727(2)
_cell_angle_gamma                 90.00
_cell_volume                      1676.72(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12304
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.496
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              784
_exptl_absorpt_coefficient_mu     1.072
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.6151
_exptl_absorpt_correction_T_max   0.7456
_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   'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean  '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             21767
_diffrn_reflns_av_R_equivalents   0.0629
_diffrn_reflns_av_sigmaI/netI     0.0528
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3834
_reflns_number_gt                 2972
_reflns_threshold_expression      >2sigma(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    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., 
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 
2004)
;
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON/PLUTON (Spek, A. L., 1998)'
_computing_publication_material   'WinGX (Farrugia, 1999)'

_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)+(0.0507P)²+1.2823P] 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          3834
_refine_ls_number_parameters      211
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0630
_refine_ls_R_factor_gt            0.0437
_refine_ls_wR_factor_ref          0.1133
_refine_ls_wR_factor_gt           0.1034
_refine_ls_goodness_of_fit_ref    1.061
_refine_ls_restrained_S_all       1.061
_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 0.2802(3) 0.27496(13) 0.4028(2) 0.0182(5) Uani 1 1 d . . .
C2 C 0.2640(3) 0.23568(13) 0.2938(2) 0.0207(5) Uani 1 1 d . . .
H2 H 0.3206 0.2461 0.2289 0.025 Uiso 1 1 calc R . .
C3 C 0.1501(4) 0.17906(14) 0.2990(2) 0.0254(6) Uani 1 1 d . . .
H3 H 0.1167 0.1454 0.2377 0.030 Uiso 1 1 calc R . .
C4 C 0.0936(3) 0.18040(14) 0.4105(2) 0.0245(6) Uani 1 1 d . . .
H4 H 0.0169 0.1479 0.4366 0.029 Uiso 1 1 calc R . .
C5 C 0.1727(3) 0.23951(13) 0.4768(2) 0.0201(5) Uani 1 1 d . . .
C6 C 0.6194(3) 0.17582(15) 0.5186(2) 0.0262(6) Uani 1 1 d . . .
H6 H 0.6929 0.2154 0.5351 0.031 Uiso 1 1 calc R . .
C7 C 0.5932(4) 0.13564(15) 0.4119(2) 0.0274(6) Uani 1 1 d . . .
H7 H 0.6456 0.1439 0.3443 0.033 Uiso 1 1 calc R . .
C8 C 0.4756(4) 0.08114(15) 0.4238(3) 0.0288(6) Uani 1 1 d . . .
H8 H 0.4361 0.0462 0.3659 0.035 Uiso 1 1 calc R . .
C9 C 0.4268(4) 0.08781(14) 0.5378(2) 0.0262(6) Uani 1 1 d . . .
H9 H 0.3484 0.0583 0.5691 0.031 Uiso 1 1 calc R . .
C10 C 0.5156(3) 0.14615(15) 0.5963(2) 0.0253(6) Uani 1 1 d . . .
H10 H 0.5075 0.1626 0.6738 0.030 Uiso 1 1 calc R . .
C11 C 0.3807(3) 0.33993(13) 0.4302(2) 0.0193(5) Uani 1 1 d . . .
C12 C 0.5713(3) 0.42810(13) 0.3655(2) 0.0216(5) Uani 1 1 d . . .
H12 H 0.5897 0.4408 0.4522 0.026 Uiso 1 1 calc R . .
C13 C 0.4606(4) 0.48557(15) 0.2968(3) 0.0307(6) Uani 1 1 d . . .
H13A H 0.5159 0.5313 0.3196 0.037 Uiso 1 1 calc R . .
H13B H 0.3447 0.4857 0.3198 0.037 Uiso 1 1 calc R . .
C14 C 0.7509(4) 0.41859(14) 0.3336(3) 0.0270(6) Uani 1 1 d . . .
H14 H 0.7354 0.4000 0.2502 0.032 Uiso 1 1 calc R . .
C15 C 0.8483(4) 0.48830(16) 0.3383(3) 0.0355(7) Uani 1 1 d . . .
H15A H 0.7882 0.5192 0.2752 0.053 Uiso 1 1 calc R . .
H15B H 0.9675 0.4800 0.3261 0.053 Uiso 1 1 calc R . .
H15C H 0.8515 0.5102 0.4164 0.053 Uiso 1 1 calc R . .
C16 C 0.8567(4) 0.36587(19) 0.4175(3) 0.0441(8) Uani 1 1 d . . .
H16A H 0.8596 0.3800 0.5005 0.066 Uiso 1 1 calc R . .
H16B H 0.9756 0.3640 0.4018 0.066 Uiso 1 1 calc R . .
H16C H 0.8028 0.3197 0.4040 0.066 Uiso 1 1 calc R . .
C17 C 0.1441(4) 0.25280(14) 0.6001(3) 0.0257(6) Uani 1 1 d . . .
N1 N 0.4750(3) 0.36182(11) 0.35142(19) 0.0217(5) Uani 1 1 d . . .
H1 H 0.4800 0.3357 0.2886 0.026 Uiso 1 1 calc R . .
O1 O 0.3738(3) 0.37506(10) 0.52228(16) 0.0284(4) Uani 1 1 d . . .
O2 O 0.2133(3) 0.30836(11) 0.65707(17) 0.0334(5) Uani 1 1 d . . .
H2A H 0.2689 0.3308 0.6131 0.050 Uiso 1 1 calc R . .
O3 O 0.0544(3) 0.21245(11) 0.64614(18) 0.0334(5) Uani 1 1 d . . .
Fe1 Fe 0.36077(4) 0.175629(18) 0.43889(3) 0.01713(12) Uani 1 1 d . . .
Cl1 Cl 0.43366(11) 0.47532(4) 0.13817(7) 0.0439(2) 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 C2 1.437(3) . ?
C1 C5 1.464(3) . ?
C1 C11 1.474(3) . ?
C1 Fe1 2.023(2) . ?
C2 C3 1.412(4) . ?
C2 Fe1 2.040(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.419(4) . ?
C3 Fe1 2.068(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.436(4) . ?
C4 Fe1 2.056(3) . ?
C4 H4 0.9500 . ?
C5 C17 1.483(4) . ?
C5 Fe1 2.021(3) . ?
C6 C7 1.420(4) . ?
C6 C10 1.426(4) . ?
C6 Fe1 2.056(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(4) . ?
C7 Fe1 2.048(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(4) . ?
C8 Fe1 2.043(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(4) . ?
C9 Fe1 2.038(3) . ?
C9 H9 0.9500 . ?
C10 Fe1 2.047(3) . ?
C10 H10 0.9500 . ?
C11 O1 1.255(3) . ?
C11 N1 1.331(3) . ?
C12 N1 1.470(3) . ?
C12 C13 1.524(4) . ?
C12 C14 1.526(4) . ?
C12 H12 1.0000 . ?
C13 Cl1 1.789(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.524(4) . ?
C14 C15 1.534(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O3 1.226(3) . ?
C17 O2 1.310(4) . ?
N1 H1 0.8800 . ?
O2 H2A 0.8400 . ?
 
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
C2 C1 C5 106.6(2) . . ?
C2 C1 C11 125.7(2) . . ?
C5 C1 C11 127.7(2) . . ?
C2 C1 Fe1 69.90(14) . . ?
C5 C1 Fe1 68.70(14) . . ?
C11 C1 Fe1 128.20(18) . . ?
C3 C2 C1 108.7(2) . . ?
C3 C2 Fe1 70.96(15) . . ?
C1 C2 Fe1 68.68(14) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
Fe1 C2 H2 126.3 . . ?
C2 C3 C4 109.1(2) . . ?
C2 C3 Fe1 68.82(15) . . ?
C4 C3 Fe1 69.42(15) . . ?
C2 C3 H3 125.4 . . ?
C4 C3 H3 125.4 . . ?
Fe1 C3 H3 127.9 . . ?
C3 C4 C5 108.0(2) . . ?
C3 C4 Fe1 70.32(15) . . ?
C5 C4 Fe1 68.08(14) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
Fe1 C4 H4 127.2 . . ?
C4 C5 C1 107.5(2) . . ?
C4 C5 C17 120.5(2) . . ?
C1 C5 C17 131.9(2) . . ?
C4 C5 Fe1 70.68(15) . . ?
C1 C5 Fe1 68.87(14) . . ?
C17 C5 Fe1 123.36(18) . . ?
C7 C6 C10 107.8(2) . . ?
C7 C6 Fe1 69.43(15) . . ?
C10 C6 Fe1 69.30(15) . . ?
C7 C6 H6 126.1 . . ?
C10 C6 H6 126.1 . . ?
Fe1 C6 H6 126.8 . . ?
C8 C7 C6 108.1(2) . . ?
C8 C7 Fe1 69.57(15) . . ?
C6 C7 Fe1 70.08(15) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 126.0 . . ?
C7 C8 C9 108.1(2) . . ?
C7 C8 Fe1 69.95(15) . . ?
C9 C8 Fe1 69.35(15) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
Fe1 C8 H8 126.3 . . ?
C10 C9 C8 107.9(2) . . ?
C10 C9 Fe1 70.07(15) . . ?
C8 C9 Fe1 69.76(15) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
Fe1 C9 H9 125.7 . . ?
C9 C10 C6 108.0(2) . . ?
C9 C10 Fe1 69.37(15) . . ?
C6 C10 Fe1 70.03(15) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
Fe1 C10 H10 126.2 . . ?
O1 C11 N1 120.6(2) . . ?
O1 C11 C1 121.7(2) . . ?
N1 C11 C1 117.6(2) . . ?
N1 C12 C13 109.7(2) . . ?
N1 C12 C14 110.2(2) . . ?
C13 C12 C14 115.1(2) . . ?
N1 C12 H12 107.1 . . ?
C13 C12 H12 107.1 . . ?
C14 C12 H12 107.1 . . ?
C12 C13 Cl1 112.83(19) . . ?
C12 C13 H13A 109.0 . . ?
Cl1 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
Cl1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C16 C14 C12 110.2(2) . . ?
C16 C14 C15 110.3(3) . . ?
C12 C14 C15 111.2(2) . . ?
C16 C14 H14 108.3 . . ?
C12 C14 H14 108.3 . . ?
C15 C14 H14 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 121.2(3) . . ?
O3 C17 C5 119.7(3) . . ?
O2 C17 C5 119.1(2) . . ?
C11 N1 C12 122.4(2) . . ?
C11 N1 H1 118.8 . . ?
C12 N1 H1 118.8 . . ?
C17 O2 H2A 109.5 . . ?
C5 Fe1 C1 42.43(10) . . ?
C5 Fe1 C9 120.13(11) . . ?
C1 Fe1 C9 157.93(11) . . ?
C5 Fe1 C2 69.89(10) . . ?
C1 Fe1 C2 41.42(10) . . ?
C9 Fe1 C2 158.66(11) . . ?
C5 Fe1 C8 154.65(11) . . ?
C1 Fe1 C8 160.44(11) . . ?
C9 Fe1 C8 40.89(11) . . ?
C2 Fe1 C8 122.33(11) . . ?
C5 Fe1 C10 108.40(11) . . ?
C1 Fe1 C10 123.26(11) . . ?
C9 Fe1 C10 40.56(11) . . ?
C2 Fe1 C10 159.17(11) . . ?
C8 Fe1 C10 68.36(11) . . ?
C5 Fe1 C7 163.80(11) . . ?
C1 Fe1 C7 124.97(11) . . ?
C9 Fe1 C7 68.48(11) . . ?
C2 Fe1 C7 107.18(11) . . ?
C8 Fe1 C7 40.47(12) . . ?
C10 Fe1 C7 68.36(11) . . ?
C5 Fe1 C4 41.24(10) . . ?
C1 Fe1 C4 69.96(10) . . ?
C9 Fe1 C4 105.62(11) . . ?
C2 Fe1 C4 68.57(11) . . ?
C8 Fe1 C4 118.42(11) . . ?
C10 Fe1 C4 124.63(11) . . ?
C7 Fe1 C4 153.83(12) . . ?
C5 Fe1 C6 126.84(11) . . ?
C1 Fe1 C6 109.34(11) . . ?
C9 Fe1 C6 68.32(11) . . ?
C2 Fe1 C6 122.83(11) . . ?
C8 Fe1 C6 68.11(12) . . ?
C10 Fe1 C6 40.67(11) . . ?
C7 Fe1 C6 40.49(11) . . ?
C4 Fe1 C6 163.03(11) . . ?
C5 Fe1 C3 68.79(11) . . ?
C1 Fe1 C3 68.94(10) . . ?
C9 Fe1 C3 122.37(11) . . ?
C2 Fe1 C3 40.21(10) . . ?
C8 Fe1 C3 105.25(11) . . ?
C10 Fe1 C3 159.97(11) . . ?
C7 Fe1 C3 119.90(11) . . ?
C4 Fe1 C3 40.26(11) . . ?
C6 Fe1 C3 156.41(12) . . ?
 
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 H1 O3  0.88 2.04 2.900(3) 164.7 4_665
O2 H2A O1  0.84 1.67 2.507(3) 178.2 .
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.524
_refine_diff_density_min   -0.560
_refine_diff_density_rms    0.139
