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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
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#$URL: svn://www.crystallography.net/cod/cif/1/51/91/1519134.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519134
loop_
_publ_author_name
'Butler, Ian R.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C22H21FeIN2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1018
_journal_year                    1994
_chemical_formula_sum            'C22 H21 Fe I N2'
_chemical_formula_weight         496.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.928(6)
_cell_length_b                   9.691(3)
_cell_length_c                   19.208(9)
_cell_measurement_temperature    293(2)
_cell_volume                     2029.5(16)
_computing_cell_refinement       REFINE
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_data_reduction        'ABSURD (Karaulov, 1992)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0924
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10581
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            unk
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unk
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.939
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                2065
_reflns_number_total             4302
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1018.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Butler, Ian R. and Coles, Simon J. and Hursthouse, Michael B. (1994) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1018)

http://ecrystals.chem.soton.ac.uk/1018/
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1519134
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'
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 . .
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'
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
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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 .
