 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H21 Fe I N2'
_chemical_formula_weight          496.16
 
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'
 'Fe'  'Fe'   0.3463   0.8444
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_Group_name_hall   '-P 2yn'
 
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                    10.928(6)
_cell_length_b                    9.691(3)
_cell_length_c                    19.208(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.89(3)
_cell_angle_gamma                 90.00
_cell_volume                      2029.5(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.36
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.11
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.624
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              984
_exptl_absorpt_coefficient_mu     2.272
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_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             10581
_diffrn_reflns_av_R_equivalents   0.0451
_diffrn_reflns_av_sigmaI/netI     0.0924
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.59
_diffrn_reflns_theta_max          28.37
_reflns_number_total              4302
_reflns_number_gt                 2065
_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)+(0.0471P)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          4302
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0900
_refine_ls_R_factor_gt            0.0406
_refine_ls_wR_factor_ref          0.0989
_refine_ls_wR_factor_gt           0.0899
_refine_ls_goodness_of_fit_ref    0.787
_refine_ls_restrained_S_all       0.787
_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
I1 I 0.32051(3) 0.18979(3) 0.150978(18) 0.09007(17) Uani 1 1 d . . .
Fe1 Fe 0.91816(6) 0.81222(6) 0.10480(3) 0.06275(19) Uani 1 1 d . . .
N1 N 0.6797(3) 0.5258(4) 0.15050(18) 0.0743(10) Uani 1 1 d . . .
N2 N 0.5759(4) 0.2225(4) -0.1830(2) 0.0748(11) Uani 1 1 d . . .
C1 C 1.0641(5) 0.6980(6) 0.1417(3) 0.1029(18) Uani 1 1 d . . .
H1 H 1.0681 0.6447 0.1821 0.123 Uiso 1 1 calc R . .
C2 C 1.0992(5) 0.8374(5) 0.1370(3) 0.0939(16) Uani 1 1 d . . .
H2 H 1.1293 0.8929 0.1738 0.113 Uiso 1 1 calc R . .
C3 C 1.0809(5) 0.8770(6) 0.0677(3) 0.0942(16) Uani 1 1 d . . .
H3 H 1.0973 0.9638 0.0498 0.113 Uiso 1 1 calc R . .
C4 C 1.0333(5) 0.7633(7) 0.0290(3) 0.0929(16) Uani 1 1 d . . .
H4 H 1.0130 0.7615 -0.0188 0.112 Uiso 1 1 calc R . .
C5 C 1.0222(5) 0.6542(6) 0.0753(4) 0.0984(17) Uani 1 1 d . . .
H5 H 0.9919 0.5668 0.0639 0.118 Uiso 1 1 calc R . .
C6 C 0.7499(4) 0.8505(4) 0.0568(2) 0.0691(12) Uani 1 1 d . . .
H6 H 0.7305 0.8464 0.0089 0.083 Uiso 1 1 calc R . .
C7 C 0.7920(4) 0.9682(5) 0.0952(3) 0.0806(14) Uani 1 1 d . . .
H7 H 0.8040 1.0552 0.0764 0.097 Uiso 1 1 calc R . .
C8 C 0.8127(5) 0.9334(5) 0.1655(2) 0.0931(16) Uani 1 1 d . . .
H8 H 0.8419 0.9925 0.2010 0.112 Uiso 1 1 calc R . .
C9 C 0.2179(5) 0.2062(5) -0.1735(2) 0.0840(15) Uani 1 1 d . . .
H9 H 0.2136 0.2547 -0.2154 0.101 Uiso 1 1 calc R . .
C10 C 0.7429(4) 0.7381(4) 0.1060(2) 0.0651(12) Uani 1 1 d . . .
C11 C 0.7034(4) 0.5970(4) 0.0926(2) 0.0583(10) Uani 1 1 d . . .
C12 C 0.6870(3) 0.5418(4) 0.0259(2) 0.0559(10) Uani 1 1 d . . .
H12 H 0.7053 0.5945 -0.0125 0.067 Uiso 1 1 calc R . .
C13 C 0.6430(3) 0.4071(4) 0.0162(2) 0.0568(10) Uani 1 1 d . . .
C14 C 0.6171(5) 0.3339(4) 0.0751(3) 0.0783(14) Uani 1 1 d . . .
H14 H 0.5875 0.2440 0.0716 0.094 Uiso 1 1 calc R . .
C15 C 0.6366(5) 0.3990(6) 0.1406(3) 0.0922(16) Uani 1 1 d . . .
H15 H 0.6177 0.3491 0.1798 0.111 Uiso 1 1 calc R . .
C16 C 0.6213(3) 0.3443(4) -0.0541(2) 0.0562(10) Uani 1 1 d . . .
C17 C 0.6447(4) 0.4098(4) -0.1144(2) 0.0772(13) Uani 1 1 d . . .
H17 H 0.6759 0.4991 -0.1122 0.093 Uiso 1 1 calc R . .
C18 C 0.6240(5) 0.3496(5) -0.1772(3) 0.0873(15) Uani 1 1 d . . .
H18 H 0.6433 0.3968 -0.2171 0.105 Uiso 1 1 calc R . .
C19 C 0.5487(5) 0.1572(5) -0.1267(3) 0.0898(16) Uani 1 1 d . . .
H19 H 0.5136 0.0699 -0.1308 0.108 Uiso 1 1 calc R . .
C20 C 0.5703(5) 0.2138(5) -0.0621(3) 0.0879(15) Uani 1 1 d . . .
H20 H 0.5506 0.1643 -0.0229 0.105 Uiso 1 1 calc R . .
C21 C 0.5554(6) 0.1525(5) -0.2523(3) 0.1062(19) Uani 1 1 d . . .
H21A H 0.6323 0.1487 -0.2746 0.127 Uiso 1 1 calc R . .
H21B H 0.5285 0.0585 -0.2451 0.127 Uiso 1 1 calc R . .
C22 C 0.4646(6) 0.2231(7) -0.2978(4) 0.142(3) Uani 1 1 d . . .
H22A H 0.4376 0.1631 -0.3356 0.213 Uiso 1 1 calc R . .
H22B H 0.5003 0.3048 -0.3162 0.213 Uiso 1 1 calc R . .
H22C H 0.3959 0.2481 -0.2719 0.213 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 C5 2.012(5) . ?
Fe1 C1 2.029(5) . ?
Fe1 C6 2.034(5) . ?
Fe1 C4 2.044(5) . ?
Fe1 C7 2.045(5) . ?
Fe1 C10 2.047(4) . ?
Fe1 C2 2.047(5) . ?
Fe1 C3 2.058(5) . ?
Fe1 C8 2.061(5) . ?
Fe1 C9 2.062(5) 3_665 ?
N1 C15 1.326(6) . ?
N1 C11 1.348(5) . ?
N2 C19 1.304(6) . ?
N2 C18 1.341(5) . ?
N2 C21 1.497(6) . ?
C1 C5 1.392(7) . ?
C1 C2 1.409(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.418(6) . ?
C6 C10 1.448(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(6) 3_665 ?
C8 H8 0.9300 . ?
C9 C8 1.405(6) 3_665 ?
C9 C10 1.443(6) 3_665 ?
C9 Fe1 2.062(5) 3_665 ?
C9 H9 0.9300 . ?
C10 C9 1.443(6) 3_665 ?
C10 C11 1.451(6) . ?
C11 C12 1.390(5) . ?
C12 C13 1.399(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(5) . ?
C13 C16 1.485(5) . ?
C14 C15 1.411(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.361(5) . ?
C16 C20 1.386(5) . ?
C17 C18 1.344(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.363(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.449(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
 
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
C5 Fe1 C1 40.3(2) . . ?
C5 Fe1 C6 121.5(2) . . ?
C1 Fe1 C6 157.3(2) . . ?
C5 Fe1 C4 40.2(2) . . ?
C1 Fe1 C4 67.4(2) . . ?
C6 Fe1 C4 107.5(2) . . ?
C5 Fe1 C7 158.1(2) . . ?
C1 Fe1 C7 160.6(2) . . ?
C6 Fe1 C7 40.67(16) . . ?
C4 Fe1 C7 123.4(2) . . ?
C5 Fe1 C10 106.43(19) . . ?
C1 Fe1 C10 121.2(2) . . ?
C6 Fe1 C10 41.55(16) . . ?
C4 Fe1 C10 123.2(2) . . ?
C7 Fe1 C10 68.59(17) . . ?
C5 Fe1 C2 67.8(2) . . ?
C1 Fe1 C2 40.44(19) . . ?
C6 Fe1 C2 160.1(2) . . ?
C4 Fe1 C2 67.3(2) . . ?
C7 Fe1 C2 124.8(2) . . ?
C10 Fe1 C2 157.6(2) . . ?
C5 Fe1 C3 67.5(2) . . ?
C1 Fe1 C3 67.1(2) . . ?
C6 Fe1 C3 124.2(2) . . ?
C4 Fe1 C3 40.2(2) . . ?
C7 Fe1 C3 109.7(2) . . ?
C10 Fe1 C3 160.4(2) . . ?
C2 Fe1 C3 39.5(2) . . ?
C5 Fe1 C8 160.3(2) . . ?
C1 Fe1 C8 124.7(2) . . ?
C6 Fe1 C8 68.28(19) . . ?
C4 Fe1 C8 158.4(2) . . ?
C7 Fe1 C8 39.71(18) . . ?
C10 Fe1 C8 68.56(18) . . ?
C2 Fe1 C8 109.1(2) . . ?
C3 Fe1 C8 123.5(2) . . ?
C5 Fe1 C9 124.1(2) . 3_665 ?
C1 Fe1 C9 108.2(2) . 3_665 ?
C6 Fe1 C9 68.74(19) . 3_665 ?
C4 Fe1 C9 160.3(2) . 3_665 ?
C7 Fe1 C9 67.1(2) . 3_665 ?
C10 Fe1 C9 41.12(16) . 3_665 ?
C2 Fe1 C9 122.7(2) . 3_665 ?
C3 Fe1 C9 157.8(2) . 3_665 ?
C8 Fe1 C9 39.84(16) . 3_665 ?
C15 N1 C11 116.3(4) . . ?
C19 N2 C18 119.1(4) . . ?
C19 N2 C21 119.2(4) . . ?
C18 N2 C21 121.7(4) . . ?
C5 C1 C2 107.9(5) . . ?
C5 C1 Fe1 69.2(3) . . ?
C2 C1 Fe1 70.5(3) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 125.9 . . ?
C3 C2 C1 107.7(5) . . ?
C3 C2 Fe1 70.7(3) . . ?
C1 C2 Fe1 69.1(3) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 125.7 . . ?
C2 C3 C4 108.4(5) . . ?
C2 C3 Fe1 69.8(3) . . ?
C4 C3 Fe1 69.4(3) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
Fe1 C3 H3 126.6 . . ?
C5 C4 C3 107.5(5) . . ?
C5 C4 Fe1 68.7(3) . . ?
C3 C4 Fe1 70.5(3) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Fe1 C4 H4 126.2 . . ?
C1 C5 C4 108.5(5) . . ?
C1 C5 Fe1 70.5(3) . . ?
C4 C5 Fe1 71.2(3) . . ?
C1 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
Fe1 C5 H5 124.1 . . ?
C7 C6 C10 107.1(4) . . ?
C7 C6 Fe1 70.1(3) . . ?
C10 C6 Fe1 69.7(3) . . ?
C7 C6 H6 126.4 . . ?
C10 C6 H6 126.4 . . ?
Fe1 C6 H6 125.4 . . ?
C8 C7 C6 109.6(4) . . ?
C8 C7 Fe1 70.7(3) . . ?
C6 C7 Fe1 69.2(3) . . ?
C8 C7 H7 125.2 . . ?
C6 C7 H7 125.2 . . ?
Fe1 C7 H7 126.4 . . ?
C7 C8 C9 108.3(4) . 3_665 ?
C7 C8 Fe1 69.5(3) . . ?
C9 C8 Fe1 70.1(3) 3_665 . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 3_665 . ?
Fe1 C8 H8 126.1 . . ?
C8 C9 C10 108.7(4) 3_665 3_665 ?
C8 C9 Fe1 70.0(3) 3_665 3_665 ?
C10 C9 Fe1 68.9(2) 3_665 3_665 ?
C8 C9 H9 125.7 3_665 . ?
C10 C9 H9 125.7 3_665 . ?
Fe1 C9 H9 127.0 3_665 . ?
C9 C10 C6 106.3(4) 3_665 . ?
C9 C10 C11 125.3(4) 3_665 . ?
C6 C10 C11 128.5(4) . . ?
C9 C10 Fe1 70.0(3) 3_665 . ?
C6 C10 Fe1 68.8(2) . . ?
C11 C10 Fe1 126.6(3) . . ?
N1 C11 C12 122.9(4) . . ?
N1 C11 C10 114.1(4) . . ?
C12 C11 C10 123.0(4) . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 117.3(4) . . ?
C14 C13 C16 120.3(4) . . ?
C12 C13 C16 122.4(3) . . ?
C13 C14 C15 118.3(4) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
N1 C15 C14 125.0(4) . . ?
N1 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
C17 C16 C20 115.3(4) . . ?
C17 C16 C13 123.7(4) . . ?
C20 C16 C13 120.9(4) . . ?
C18 C17 C16 122.1(4) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
N2 C18 C17 121.0(4) . . ?
N2 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
N2 C19 C20 121.6(4) . . ?
N2 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C16 120.8(5) . . ?
C19 C20 H20 119.6 . . ?
C16 C20 H20 119.6 . . ?
C22 C21 N2 112.2(5) . . ?
C22 C21 H21A 109.2 . . ?
N2 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
N2 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.846
_diffrn_reflns_theta_full              28.37
_diffrn_measured_fraction_theta_full   0.846
_refine_diff_density_max    0.939
_refine_diff_density_min   -0.362
_refine_diff_density_rms    0.080
