#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008936.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_2008936
loop_
_publ_author_name
'Argay, Gyula'
'Kálmán, Alajos'
'Leovac, Vukadin M.'
_publ_section_title
;
 [Fe(HL)Cl₂]^.^EtOH, where HL is the monoanion of
 benzoylacetone S-n-propylisothiosemicarbazone
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1440
_journal_page_last               1443
_journal_paper_doi               10.1107/S0108270199007647
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          '[Fe (C14 H18 N3 O S) Cl2], C2 H6 O'
_chemical_formula_moiety         '[C14 H18 Cl2 Fe1 N3 O1 S1].C2 H6 O1'
_chemical_formula_sum            'C16 H24 Cl2 Fe N3 O2 S'
_chemical_formula_weight         449.19
_chemical_name_common
; Benzoylacetone-(S-n-propylisothiosemicarbazonato)iron(III)
 dichloride ethanol solvate
;
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.460(10)
_cell_angle_beta                 71.690(10)
_cell_angle_gamma                68.870(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7390(10)
_cell_length_b                   11.680(2)
_cell_length_c                   11.858(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.87
_cell_measurement_theta_min      14.94
_cell_volume                     1032.5(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and  PX (Párkányi, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710730
_diffrn_reflns_av_R_equivalents  0.012
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6088
_diffrn_reflns_theta_full        29.42
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.101
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0420P)²+0.4248P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.097
_reflns_number_gt                3173
_reflns_number_total             5678
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1418.cif
_cod_data_source_block           le4f
_cod_original_formula_sum        'C16 H24 Cl2 Fe1 N3 O2 S1'
_cod_database_code               2008936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Fe1 0.12085(5) 0.20099(3) 0.41116(3) 0.04184(11) Uani d . 1 . . Fe
Cl1 0.15153(10) 0.10585(6) 0.26621(7) 0.0599(2) Uani d . 1 . . Cl
Cl2 -0.15155(9) 0.23964(6) 0.50599(7) 0.05565(18) Uani d . 1 . . Cl
S1 0.38051(11) -0.08383(6) 0.72498(8) 0.0646(2) Uani d . 1 . . S
O1 0.1233(3) 0.36492(16) 0.29597(16) 0.0568(5) Uani d . 1 . . O
N1 0.2223(3) 0.03395(19) 0.5298(2) 0.0511(6) Uani d D 1 . . N
H1 0.2102(3) -0.0374(8) 0.5357(2) 0.066 Uiso d RD 1 . . H
N2 0.3191(3) 0.15073(17) 0.59266(19) 0.0471(5) Uani d D 1 . . N
H2 0.3779(7) 0.1624(2) 0.6311(5) 0.061 Uiso d RD 1 . . H
N3 0.2493(3) 0.25130(18) 0.50132(18) 0.0411(5) Uani d . 1 . . N
C1 0.3368(4) -0.2198(2) 0.7186(3) 0.0523(7) Uani d . 1 . . C
H1A 0.2168 -0.2036 0.7293 0.068 Uiso calc R 1 . . H
H1B 0.3922 -0.2375 0.6392 0.068 Uiso calc R 1 . . H
C2 0.2981(3) 0.0381(2) 0.6051(2) 0.0446(6) Uani d . 1 . . C
C3 0.2589(3) 0.3658(2) 0.4893(2) 0.0429(6) Uani d . 1 . . C
C4 0.3377(4) 0.3856(3) 0.5745(3) 0.0565(7) Uani d . 1 . . C
H4A 0.3280 0.4745 0.5557 0.085 Uiso calc R 1 . . H
H4B 0.4542 0.3380 0.5639 0.085 Uiso calc R 1 . . H
H4C 0.2812 0.3568 0.6584 0.085 Uiso calc R 1 . . H
C5 0.1965(3) 0.4710(2) 0.3970(2) 0.0459(6) Uani d . 1 . . C
H5 0.1984 0.5499 0.3975 0.060 Uiso calc R 1 . . H
C6 0.1325(3) 0.4697(2) 0.3056(2) 0.0428(6) Uani d . 1 . . C
C7 0.0735(3) 0.5878(2) 0.2103(2) 0.0437(6) Uani d . 1 . . C
C8 0.0287(4) 0.5799(3) 0.1118(3) 0.0621(8) Uani d . 1 . . C
H8 0.0383 0.5004 0.1052 0.081 Uiso calc R 1 . . H
C9 -0.0300(5) 0.6882(3) 0.0232(3) 0.0762(10) Uani d . 1 . . C
H9 -0.0592 0.6810 -0.0425 0.099 Uiso calc R 1 . . H
C10 -0.0457(4) 0.8064(3) 0.0312(3) 0.0703(9) Uani d . 1 . . C
H10 -0.0843 0.8791 -0.0290 0.091 Uiso calc R 1 . . H
C11 -0.0037(4) 0.8161(3) 0.1292(3) 0.0665(9) Uani d . 1 . . C
H11 -0.0152 0.8959 0.1359 0.086 Uiso calc R 1 . . H
C12 0.0557(4) 0.7078(2) 0.2179(3) 0.0576(7) Uani d . 1 . . C
H12 0.0841 0.7156 0.2837 0.075 Uiso calc R 1 . . H
C21 0.4010(4) -0.3320(2) 0.8206(3) 0.0645(8) Uani d . 1 . . C
H21A 0.5192 -0.3433 0.8122 0.084 Uiso calc R 1 . . H
H21B 0.3411 -0.3146 0.8995 0.084 Uiso calc R 1 . . H
C22 0.3786(6) -0.4532(3) 0.8177(4) 0.0968(13) Uani d . 1 . . C
H22A 0.4206 -0.5222 0.8837 0.145 Uiso calc R 1 . . H
H22B 0.4396 -0.4715 0.7403 0.145 Uiso calc R 1 . . H
H22C 0.2615 -0.4428 0.8274 0.145 Uiso calc R 1 . . H
O13 0.5052(3) 0.1276(2) 0.7612(2) 0.0866(8) Uani d D 1 . . O
H13 0.5897(11) 0.0687(8) 0.7616(2) 0.113 Uiso d RD 1 . . H
C14 0.5318(7) 0.2007(4) 0.8178(4) 0.1277(18) Uani d . 1 . . C
H14A 0.4369 0.2766 0.8146 0.166 Uiso calc R 1 . . H
H14B 0.6294 0.2284 0.7659 0.166 Uiso calc R 1 . . H
C15 0.5553(7) 0.1579(4) 0.9367(4) 0.1241(18) Uani d . 1 . . C
H15A 0.4599 0.1313 0.9920 0.186 Uiso calc R 1 . . H
H15B 0.5679 0.2253 0.9585 0.186 Uiso calc R 1 . . H
H15C 0.6546 0.0871 0.9425 0.186 Uiso calc R 1 . . H
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'
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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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
N1 Fe1 Cl1 93.59(6) yes
N1 Fe1 N3 75.12(8) yes
O1 Fe1 N3 83.91(7) yes
O1 Fe1 Cl1 94.56(6) yes
N3 Fe1 Cl1 144.63(7) yes
O1 Fe1 N1 153.76(9) yes
Cl2 Fe1 Cl1 106.11(3) yes
N1 Fe1 Cl2 101.01(7) yes
N3 Fe1 Cl2 108.91(6) yes
O1 Fe1 Cl2 100.58(7) yes
C2 S1 C1 103.32(12) ?
C6 O1 Fe1 133.06(16) ?
C2 N1 Fe1 118.34(17) ?
C2 N2 N3 114.91(19) ?
C3 N3 N2 117.41(19) ?
C3 N3 Fe1 128.58(16) ?
N2 N3 Fe1 113.73(14) ?
C21 C1 S1 108.01(19) ?
N1 C2 N2 117.6(2) ?
N1 C2 S1 129.23(19) ?
N2 C2 S1 113.22(17) ?
N3 C3 C5 120.8(2) ?
N3 C3 C4 120.8(2) ?
C5 C3 C4 118.4(2) ?
C6 C5 C3 126.6(2) ?
O1 C6 C5 122.1(2) ?
O1 C6 C7 116.2(2) ?
C5 C6 C7 121.7(2) ?
C8 C7 C12 117.9(2) ?
C8 C7 C6 119.7(2) ?
C12 C7 C6 122.4(2) ?
C9 C8 C7 121.0(3) ?
C10 C9 C8 120.6(3) ?
C9 C10 C11 119.3(3) ?
C10 C11 C12 120.3(3) ?
C11 C12 C7 120.9(3) ?
C22 C21 C1 111.8(3) ?
O13 C14 C15 123.4(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 N1 . 2.045(2) yes
Fe1 N3 . 2.102(2) yes
Fe1 O1 . 1.926(2) yes
Fe1 Cl1 . 2.2580(10) yes
Fe1 Cl2 . 2.2440(10) yes
S1 C2 . 1.747(2) ?
S1 C1 . 1.793(2) ?
O1 C6 . 1.301(3) ?
N1 C2 . 1.289(3) ?
N2 C2 . 1.344(3) ?
N2 N3 . 1.389(3) ?
N3 C3 . 1.325(3) ?
C1 C21 . 1.509(4) ?
C3 C5 . 1.398(3) ?
C3 C4 . 1.505(3) ?
C5 C6 . 1.373(3) ?
C6 C7 . 1.485(3) ?
C7 C8 . 1.384(4) ?
C7 C12 . 1.386(3) ?
C8 C9 . 1.380(4) ?
C9 C10 . 1.371(4) ?
C10 C11 . 1.375(4) ?
C11 C12 . 1.383(4) ?
C21 C22 . 1.510(4) ?
O13 C14 . 1.371(4) ?
C14 C15 . 1.375(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Cl2 2_556 0.85 2.82 3.649(2) 165 yes
N2 H2 O13 1_555 0.86 2.02 2.838(3) 159 yes
O13 H13 Cl1 2_656 0.81 2.46 3.264(2) 172 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 Fe1 O1 C6 -62.1(3)
N3 Fe1 O1 C6 -25.3(2)
Cl2 Fe1 O1 C6 82.8(2)
Cl1 Fe1 O1 C6 -169.8(2)
O1 Fe1 N1 C2 43.5(3)
N3 Fe1 N1 C2 5.4(2)
Cl2 Fe1 N1 C2 -101.4(2)
Cl1 Fe1 N1 C2 151.4(2)
C2 N2 N3 C3 176.7(2)
C2 N2 N3 Fe1 2.2(3)
O1 Fe1 N3 C3 18.3(2)
N1 Fe1 N3 C3 -177.6(2)
Cl2 Fe1 N3 C3 -80.8(2)
Cl1 Fe1 N3 C3 107.6(2)
O1 Fe1 N3 N2 -167.97(18)
N1 Fe1 N3 N2 -3.87(16)
Cl2 Fe1 N3 N2 92.90(16)
Cl1 Fe1 N3 N2 -78.66(19)
C2 S1 C1 C21 -179.2(2)
Fe1 N1 C2 N2 -6.1(4)
Fe1 N1 C2 S1 173.85(16)
N3 N2 C2 N1 2.4(4)
N3 N2 C2 S1 -177.59(17)
C1 S1 C2 N1 0.6(3)
C1 S1 C2 N2 -179.5(2)
N2 N3 C3 C5 177.9(2)
Fe1 N3 C3 C5 -8.6(4)
N2 N3 C3 C4 -1.9(4)
Fe1 N3 C3 C4 171.6(2)
N3 C3 C5 C6 -5.2(4)
C4 C3 C5 C6 174.7(3)
Fe1 O1 C6 C5 21.5(4)
Fe1 O1 C6 C7 -159.87(18)
C3 C5 C6 O1 0.1(4)
C3 C5 C6 C7 -178.4(3)
O1 C6 C7 C8 -6.2(4)
C5 C6 C7 C8 172.4(3)
O1 C6 C7 C12 171.5(3)
C5 C6 C7 C12 -9.9(4)
C12 C7 C8 C9 0.8(5)
C6 C7 C8 C9 178.6(3)
C7 C8 C9 C10 -0.2(6)
C8 C9 C10 C11 -0.6(6)
C9 C10 C11 C12 0.8(6)
C10 C11 C12 C7 -0.2(5)
C8 C7 C12 C11 -0.6(5)
C6 C7 C12 C11 -178.3(3)
S1 C1 C21 C22 -176.7(3)
