#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106645.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_8106645
loop_
_publ_author_name
'Škoch, Karel'
'Císařová, Ivana'
'Štěpnička, Petr'
_publ_section_title
;
 The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene,
 C13H12FeN2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              693
_journal_page_last               695
_journal_paper_doi               10.1515/ncrs-2017-0015
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C13 H12 Fe N2 O'
_chemical_formula_sum            'C13 H12 Fe N2 O'
_chemical_formula_weight         268.10
_chemical_name_systematic
; 
(5-Methyl-1,2,4-oxadiazol-3-yl)ferrocene 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0762(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9035(2)
_cell_length_b                   20.7111(6)
_cell_length_c                   9.1403(3)
_cell_measurement_reflns_used    3935
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.97
_cell_volume                     1117.57(6)
_computing_cell_refinement       'SAINT V8.34A [4]'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3 [3]'
_computing_data_reduction        'SAINT V8.34A [4]'
_computing_molecular_graphics    'PLATON [5]'
_computing_publication_material  'SHELXL-97 [1] and PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [1]'
_computing_structure_solution    'SHELXS-97 [1]'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans to fill the Evald sphere'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8213
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.331
_exptl_absorpt_correction_T_max  0.8545
_exptl_absorpt_correction_T_min  0.4665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.) [2]'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w = 1/[σ²(Fₒ²)+(0.0249P)²+0.7617P],
 where P = (Fₒ²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                2190
_reflns_number_total             2542
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0015_suppl.cif
_cod_data_source_block           ks327
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106645
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
Fe Fe 0.98415(4) 0.160763(11) 0.13905(3) 0.01745(9) Uani 1 1 d . . .
C1 C 1.0151(3) 0.17589(8) 0.35737(18) 0.0180(3) Uani 1 1 d . . .
C2 C 1.2316(3) 0.18226(9) 0.28822(19) 0.0208(4) Uani 1 1 d . . .
H2 H 1.3632 0.1575 0.3091 0.025 Uiso 1 1 calc R . .
C3 C 1.2134(3) 0.23242(9) 0.1825(2) 0.0243(4) Uani 1 1 d . . .
H3 H 1.3312 0.2468 0.1198 0.029 Uiso 1 1 calc R . .
C4 C 0.9891(3) 0.25736(9) 0.1866(2) 0.0237(4) Uani 1 1 d . . .
H4 H 0.9316 0.2914 0.1275 0.028 Uiso 1 1 calc R . .
C5 C 0.8658(3) 0.22260(8) 0.29448(19) 0.0204(4) Uani 1 1 d . . .
H5 H 0.7117 0.2292 0.3201 0.025 Uiso 1 1 calc R . .
C6 C 0.8829(4) 0.06782(9) 0.1095(2) 0.0329(5) Uani 1 1 d . . .
H6 H 0.8669 0.0363 0.1842 0.039 Uiso 1 1 calc R . .
C7 C 1.0767(4) 0.07920(11) 0.0292(3) 0.0417(6) Uani 1 1 d . . .
H7 H 1.2160 0.0567 0.0396 0.050 Uiso 1 1 calc R . .
C8 C 1.0356(6) 0.12834(13) -0.0680(3) 0.0570(8) Uani 1 1 d . . .
H8 H 1.1414 0.1457 -0.1357 0.068 Uiso 1 1 calc R . .
C9 C 0.8129(6) 0.14828(11) -0.0505(3) 0.0623(10) Uani 1 1 d . . .
H9 H 0.7391 0.1814 -0.1043 0.075 Uiso 1 1 calc R . .
C10 C 0.7148(4) 0.11026(12) 0.0626(3) 0.0433(6) Uani 1 1 d . . .
H10 H 0.5644 0.1132 0.0989 0.052 Uiso 1 1 calc R . .
O11 O 0.9829(2) 0.05233(6) 0.62557(14) 0.0247(3) Uani 1 1 d . . .
N12 N 1.1115(3) 0.09436(8) 0.53576(17) 0.0254(4) Uani 1 1 d . . .
C13 C 0.9566(3) 0.12731(8) 0.46631(18) 0.0167(3) Uani 1 1 d . . .
N14 N 0.7366(2) 0.11164(7) 0.50355(16) 0.0195(3) Uani 1 1 d . . .
C15 C 0.7643(3) 0.06643(8) 0.59945(19) 0.0189(4) Uani 1 1 d . . .
C16 C 0.5931(3) 0.02923(10) 0.6823(2) 0.0269(4) Uani 1 1 d . . .
H16A H 0.4412 0.0445 0.6563 0.040 Uiso 1 1 calc R . .
H16B H 0.6182 0.0352 0.7874 0.040 Uiso 1 1 calc R . .
H16C H 0.6066 -0.0167 0.6579 0.040 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'
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'
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
C9 Fe C10 41.17(12) . .
C9 Fe C1 155.16(13) . .
C10 Fe C1 119.25(9) . .
C9 Fe C8 40.04(13) . .
C10 Fe C8 68.07(10) . .
C1 Fe C8 162.64(12) . .
C9 Fe C6 67.57(9) . .
C10 Fe C6 40.13(10) . .
C1 Fe C6 107.64(8) . .
C8 Fe C6 66.89(9) . .
C9 Fe C5 120.43(11) . .
C10 Fe C5 107.17(8) . .
C1 Fe C5 41.16(7) . .
C8 Fe C5 155.43(11) . .
C6 Fe C5 125.93(8) . .
C9 Fe C7 66.82(11) . .
C10 Fe C7 67.26(9) . .
C1 Fe C7 126.03(9) . .
C8 Fe C7 39.41(11) . .
C6 Fe C7 39.60(9) . .
C5 Fe C7 162.97(9) . .
C9 Fe C2 162.73(12) . .
C10 Fe C2 154.32(10) . .
C1 Fe C2 41.17(7) . .
C8 Fe C2 125.83(11) . .
C6 Fe C2 120.26(8) . .
C5 Fe C2 69.12(7) . .
C7 Fe C2 108.46(9) . .
C9 Fe C3 126.07(10) . .
C10 Fe C3 163.58(10) . .
C1 Fe C3 68.81(7) . .
C8 Fe C3 108.70(9) . .
C6 Fe C3 154.98(9) . .
C5 Fe C3 68.67(7) . .
C7 Fe C3 121.22(8) . .
C2 Fe C3 40.69(7) . .
C9 Fe C4 108.29(8) . .
C10 Fe C4 126.04(9) . .
C1 Fe C4 68.84(7) . .
C8 Fe C4 121.23(9) . .
C6 Fe C4 163.20(9) . .
C5 Fe C4 40.76(7) . .
C7 Fe C4 155.48(9) . .
C2 Fe C4 68.65(8) . .
C3 Fe C4 40.64(8) . .
C5 C1 C2 108.08(15) . .
C5 C1 C13 126.55(16) . .
C2 C1 C13 125.27(16) . .
C5 C1 Fe 69.76(10) . .
C2 C1 Fe 70.08(10) . .
C13 C1 Fe 122.99(12) . .
C3 C2 C1 107.49(16) . .
C3 C2 Fe 69.70(10) . .
C1 C2 Fe 68.75(10) . .
C3 C2 H2 126.3 . .
C1 C2 H2 126.3 . .
Fe C2 H2 126.8 . .
C4 C3 C2 108.47(16) . .
C4 C3 Fe 69.70(10) . .
C2 C3 Fe 69.61(10) . .
C4 C3 H3 125.8 . .
C2 C3 H3 125.8 . .
Fe C3 H3 126.5 . .
C3 C4 C5 108.17(16) . .
C3 C4 Fe 69.66(10) . .
C5 C4 Fe 69.22(10) . .
C3 C4 H4 125.9 . .
C5 C4 H4 125.9 . .
Fe C4 H4 126.8 . .
C4 C5 C1 107.79(16) . .
C4 C5 Fe 70.02(10) . .
C1 C5 Fe 69.08(10) . .
C4 C5 H5 126.1 . .
C1 C5 H5 126.1 . .
Fe C5 H5 126.4 . .
C7 C6 C10 108.6(2) . .
C7 C6 Fe 70.45(12) . .
C10 C6 Fe 69.68(12) . .
C7 C6 H6 125.7 . .
C10 C6 H6 125.7 . .
Fe C6 H6 125.8 . .
C8 C7 C6 109.0(2) . .
C8 C7 Fe 69.97(13) . .
C6 C7 Fe 69.95(12) . .
C8 C7 H7 125.5 . .
C6 C7 H7 125.5 . .
Fe C7 H7 126.1 . .
C7 C8 C9 108.2(2) . .
C7 C8 Fe 70.62(13) . .
C9 C8 Fe 69.57(13) . .
C7 C8 H8 125.9 . .
C9 C8 H8 125.9 . .
Fe C8 H8 125.5 . .
C8 C9 C10 107.8(2) . .
C8 C9 Fe 70.39(14) . .
C10 C9 Fe 69.64(12) . .
C8 C9 H9 126.1 . .
C10 C9 H9 126.1 . .
Fe C9 H9 125.5 . .
C6 C10 C9 106.4(2) . .
C6 C10 Fe 70.19(12) . .
C9 C10 Fe 69.19(13) . .
C6 C10 H10 126.8 . .
C9 C10 H10 126.8 . .
Fe C10 H10 125.4 . .
C15 O11 N12 106.16(13) . .
C13 N12 O11 103.14(13) . .
N12 C13 N14 114.56(15) . .
N12 C13 C1 121.78(15) . .
N14 C13 C1 123.66(15) . .
C15 N14 C13 102.65(14) . .
N14 C15 O11 113.48(15) . .
N14 C15 C16 129.65(16) . .
O11 C15 C16 116.87(15) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe C9 2.021(2) .
Fe C10 2.027(2) .
Fe C1 2.0280(17) .
Fe C8 2.032(2) .
Fe C6 2.0336(19) .
Fe C5 2.0370(17) .
Fe C7 2.040(2) .
Fe C2 2.0458(18) .
Fe C3 2.0471(18) .
Fe C4 2.0475(18) .
C1 C5 1.429(3) .
C1 C2 1.432(2) .
C1 C13 1.457(2) .
C2 C3 1.423(3) .
C2 H2 0.9500 .
C3 C4 1.422(3) .
C3 H3 0.9500 .
C4 C5 1.422(3) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 C7 1.380(3) .
C6 C10 1.393(3) .
C6 H6 0.9500 .
C7 C8 1.373(4) .
C7 H7 0.9500 .
C8 C9 1.388(4) .
C8 H8 0.9500 .
C9 C10 1.423(4) .
C9 H9 0.9500 .
C10 H10 0.9500 .
O11 C15 1.344(2) .
O11 N12 1.4176(19) .
N12 C13 1.305(2) .
C13 N14 1.382(2) .
N14 C15 1.293(2) .
C15 C16 1.480(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
