#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/85/2218545.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218545
loop_
_publ_author_name
'Xia, Dong-Sheng'
'Chen, Wu'
'Jiang, Li-Li'
'Zeng, Qing-Fu'
_publ_section_title
;
 Bis[2-(butyliminomethyl)-4-chlorophenolato]iron(II)
;
_journal_coeditor_code           SJ2502
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m837
_journal_paper_doi               10.1107/S1600536808015080
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Fe (C11 H13 Cl1 N1 O1)2]'
_chemical_formula_moiety         'C22 H26 Cl2 Fe N2 O2'
_chemical_formula_sum            'C22 H26 Cl2 Fe N2 O2'
_chemical_formula_weight         477.20
_chemical_name_systematic
;
Bis[2-(butyliminomethyl)-4-chlorophenolato]iron(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.093(3)
_cell_angle_beta                 90.800(2)
_cell_angle_gamma                105.755(3)
_cell_formula_units_Z            2
_cell_length_a                   10.059(2)
_cell_length_b                   10.100(2)
_cell_length_c                   11.569(3)
_cell_measurement_reflns_used    2122
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1121.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4427
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.7805
_exptl_absorpt_correction_T_min  0.7549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.798
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1206P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.2009
_reflns_number_gt                3009
_reflns_number_total             4174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2502.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218545
_cod_database_fobs_code          2218545
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Fe Fe1 0.88207(6) 0.05266(6) 0.59267(5) 0.0378(3) Uani d . 1
Cl Cl1 1.28816(16) 0.67927(15) 0.38259(15) 0.0708(5) Uani d . 1
Cl Cl2 0.43021(19) -0.54688(18) 0.80626(17) 0.0875(6) Uani d . 1
N N1 1.0140(4) 0.2108(5) 0.6944(3) 0.0510(10) Uani d . 1
N N2 0.7290(4) -0.0862(4) 0.4948(4) 0.0505(10) Uani d . 1
O O1 0.9611(4) 0.1217(4) 0.4557(3) 0.0585(9) Uani d . 1
O O2 0.8151(5) -0.0192(4) 0.7305(3) 0.0742(12) Uani d . 1
C C1 1.0932(5) 0.3499(5) 0.5383(4) 0.0489(12) Uani d . 1
C C2 1.0296(5) 0.2505(5) 0.4429(4) 0.0474(11) Uani d . 1
C C3 1.0436(6) 0.2901(6) 0.3317(5) 0.0546(13) Uani d . 1
H H3 0.9990 0.2270 0.2683 0.065 Uiso calc R 1
C C4 1.1218(6) 0.4204(6) 0.3124(5) 0.0554(13) Uani d . 1
H H4 1.1309 0.4439 0.2371 0.067 Uiso calc R 1
C C5 1.1865(5) 0.5153(5) 0.4071(5) 0.0542(13) Uani d . 1
C C6 1.1748(5) 0.4835(5) 0.5187(5) 0.0508(12) Uani d . 1
H H6 1.2195 0.5484 0.5810 0.061 Uiso calc R 1
C C7 1.0854(5) 0.3227(5) 0.6570(4) 0.0500(12) Uani d . 1
H H7 1.1369 0.3927 0.7128 0.060 Uiso calc R 1
C C8 1.0251(6) 0.2141(6) 0.8225(4) 0.0620(14) Uani d . 1
H H8A 1.1163 0.2703 0.8520 0.074 Uiso calc R 1
H H8B 1.0137 0.1207 0.8410 0.074 Uiso calc R 1
C C9 0.9166(7) 0.2733(6) 0.8810(5) 0.0685(16) Uani d . 1
H H9A 0.9317 0.3682 0.8652 0.082 Uiso calc R 1
H H9B 0.8263 0.2205 0.8469 0.082 Uiso calc R 1
C C10 0.9164(8) 0.2719(8) 1.0105(5) 0.089(2) Uani d . 1
H H10A 1.0081 0.3198 1.0446 0.107 Uiso calc R 1
H H10B 0.8947 0.1766 1.0268 0.107 Uiso calc R 1
C C11 0.8128(9) 0.3404(8) 1.0668(6) 0.103(3) Uani d . 1
H H11A 0.8260 0.4303 1.0423 0.154 Uiso calc R 1
H H11B 0.8259 0.3502 1.1501 0.154 Uiso calc R 1
H H11C 0.7207 0.2842 1.0436 0.154 Uiso calc R 1
C C12 0.6426(5) -0.2250(5) 0.6502(5) 0.0516(12) Uani d . 1
C C13 0.7240(6) -0.1362(6) 0.7427(5) 0.0597(14) Uani d . 1
C C14 0.7078(7) -0.1759(7) 0.8555(6) 0.0753(18) Uani d . 1
H H14 0.7590 -0.1169 0.9183 0.090 Uiso calc R 1
C C15 0.6177(7) -0.3004(6) 0.8748(5) 0.0718(17) Uani d . 1
H H15 0.6090 -0.3253 0.9497 0.086 Uiso calc R 1
C C16 0.5405(6) -0.3874(6) 0.7816(6) 0.0632(15) Uani d . 1
C C17 0.5499(5) -0.3530(6) 0.6707(5) 0.0571(13) Uani d . 1
H H17 0.4963 -0.4126 0.6093 0.069 Uiso calc R 1
C C18 0.6473(5) -0.1940(5) 0.5322(5) 0.0528(13) Uani d . 1
H H18 0.5860 -0.2570 0.4773 0.063 Uiso calc R 1
C C19 0.7085(6) -0.0779(6) 0.3698(4) 0.0551(13) Uani d . 1
H H19A 0.6551 -0.1679 0.3313 0.066 Uiso calc R 1
H H19B 0.7976 -0.0547 0.3350 0.066 Uiso calc R 1
C C20 0.6344(7) 0.0292(6) 0.3507(5) 0.0688(16) Uani d . 1
H H20A 0.6864 0.1186 0.3913 0.083 Uiso calc R 1
H H20B 0.5442 0.0044 0.3835 0.083 Uiso calc R 1
C C21 0.6166(8) 0.0414(8) 0.2213(6) 0.084(2) Uani d . 1
H H21A 0.5821 0.1212 0.2149 0.100 Uiso calc R 1
H H21B 0.7070 0.0598 0.1885 0.100 Uiso calc R 1
C C22 0.5237(12) -0.0799(10) 0.1499(7) 0.132(4) Uani d . 1
H H22A 0.5594 -0.1588 0.1514 0.198 Uiso calc R 1
H H22B 0.5178 -0.0608 0.0711 0.198 Uiso calc R 1
H H22C 0.4334 -0.0993 0.1808 0.198 Uiso calc R 1
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 Fe1 O1 176.03(18) y
O2 Fe1 N2 91.69(17) y
O1 Fe1 N2 90.18(16) y
O2 Fe1 N1 87.76(17) y
O1 Fe1 N1 90.95(16) y
N2 Fe1 N1 170.71(16) y
C7 N1 C8 114.2(4) ?
C7 N1 Fe1 123.9(4) ?
C8 N1 Fe1 121.6(3) ?
C18 N2 C19 114.8(5) ?
C18 N2 Fe1 124.0(4) ?
C19 N2 Fe1 121.1(3) ?
C2 O1 Fe1 128.2(3) ?
C13 O2 Fe1 129.4(4) ?
C2 C1 C6 120.0(5) ?
C2 C1 C7 123.5(5) ?
C6 C1 C7 116.5(5) ?
O1 C2 C3 119.6(4) ?
O1 C2 C1 122.4(5) ?
C3 C2 C1 118.0(5) ?
C4 C3 C2 122.1(5) ?
C4 C3 H3 119.0 ?
C2 C3 H3 119.0 ?
C3 C4 C5 119.0(5) ?
C3 C4 H4 120.5 ?
C5 C4 H4 120.5 ?
C6 C5 C4 121.7(5) ?
C6 C5 Cl1 119.2(4) ?
C4 C5 Cl1 119.0(4) ?
C5 C6 C1 119.1(5) ?
C5 C6 H6 120.4 ?
C1 C6 H6 120.4 ?
N1 C7 C1 126.6(5) ?
N1 C7 H7 116.7 ?
C1 C7 H7 116.7 ?
N1 C8 C9 111.1(5) ?
N1 C8 H8A 109.4 ?
C9 C8 H8A 109.4 ?
N1 C8 H8B 109.4 ?
C9 C8 H8B 109.4 ?
H8A C8 H8B 108.0 ?
C10 C9 C8 113.9(6) ?
C10 C9 H9A 108.8 ?
C8 C9 H9A 108.8 ?
C10 C9 H9B 108.8 ?
C8 C9 H9B 108.8 ?
H9A C9 H9B 107.7 ?
C9 C10 C11 112.3(7) ?
C9 C10 H10A 109.2 ?
C11 C10 H10A 109.2 ?
C9 C10 H10B 109.2 ?
C11 C10 H10B 109.2 ?
H10A C10 H10B 107.9 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C13 C12 C17 120.1(5) ?
C13 C12 C18 123.1(5) ?
C17 C12 C18 116.8(5) ?
O2 C13 C12 123.9(5) ?
O2 C13 C14 118.1(5) ?
C12 C13 C14 118.0(5) ?
C15 C14 C13 121.6(6) ?
C15 C14 H14 119.2 ?
C13 C14 H14 119.2 ?
C14 C15 C16 119.2(6) ?
C14 C15 H15 120.4 ?
C16 C15 H15 120.4 ?
C17 C16 C15 121.7(5) ?
C17 C16 Cl2 119.4(5) ?
C15 C16 Cl2 118.9(5) ?
C16 C17 C12 119.3(5) ?
C16 C17 H17 120.4 ?
C12 C17 H17 120.4 ?
N2 C18 C12 126.2(5) ?
N2 C18 H18 116.9 ?
C12 C18 H18 116.9 ?
N2 C19 C20 111.7(4) ?
N2 C19 H19A 109.3 ?
C20 C19 H19A 109.3 ?
N2 C19 H19B 109.3 ?
C20 C19 H19B 109.3 ?
H19A C19 H19B 107.9 ?
C19 C20 C21 112.0(5) ?
C19 C20 H20A 109.2 ?
C21 C20 H20A 109.2 ?
C19 C20 H20B 109.2 ?
C21 C20 H20B 109.2 ?
H20A C20 H20B 107.9 ?
C22 C21 C20 116.1(6) ?
C22 C21 H21A 108.3 ?
C20 C21 H21A 108.3 ?
C22 C21 H21B 108.3 ?
C20 C21 H21B 108.3 ?
H21A C21 H21B 107.4 ?
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_publ_flag
Fe1 O2 1.890(4) y
Fe1 O1 1.907(4) y
Fe1 N2 2.001(4) y
Fe1 N1 2.010(4) y
Cl1 C5 1.753(5) ?
Cl2 C16 1.749(6) ?
N1 C7 1.291(7) ?
N1 C8 1.480(6) ?
N2 C18 1.299(7) ?
N2 C19 1.474(6) ?
O1 C2 1.324(6) ?
O2 C13 1.309(6) ?
C1 C2 1.412(7) ?
C1 C6 1.423(7) ?
C1 C7 1.432(7) ?
C2 C3 1.392(7) ?
C3 C4 1.384(7) ?
C3 H3 0.9300 ?
C4 C5 1.388(8) ?
C4 H4 0.9300 ?
C5 C6 1.368(7) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.510(8) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.500(8) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.513(10) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 C13 1.399(7) ?
C12 C17 1.422(7) ?
C12 C18 1.438(7) ?
C13 C14 1.410(8) ?
C14 C15 1.381(8) ?
C14 H14 0.9300 ?
C15 C16 1.383(9) ?
C15 H15 0.9300 ?
C16 C17 1.368(8) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 C20 1.506(7) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C21 1.529(8) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 C22 1.470(10) ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
