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#$Date: 2021-11-29 11:41:28 +0200 (Mon, 29 Nov 2021) $
#$Revision: 270908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/54/1565418.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_1565418
loop_
_publ_author_name
'Cheng, Wenqian'
'Shi, Xiaoling'
'Zhang, Yu'
'Jian, Yajun'
'Zhang, Guofang'
_publ_section_title
;
 Novel ferrocene-based 1,2,3-triazolyl compounds: Synthesis,
 anti-migration properties and catalytic effects on oxidizers during
 combustion
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119374
_journal_paper_doi               10.1016/j.ica.2019.119374
_journal_volume                  502
_journal_year                    2020
_chemical_formula_sum            'C20 H19 Fe N3 O'
_chemical_formula_weight         373.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.583(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7232(11)
_cell_length_b                   23.191(5)
_cell_length_c                   13.045(3)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.37
_cell_volume                     1689.8(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.601
_diffrn_measured_fraction_theta_max 0.623
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.601
_diffrn_reflns_Laue_measured_fraction_max 0.623
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11933
_diffrn_reflns_point_group_measured_fraction_full 0.601
_diffrn_reflns_point_group_measured_fraction_max 0.623
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.376
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6642
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0304
_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)+(0.0273P)²+0.9057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1814
_reflns_number_total             2061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1565418
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.07388(6) 0.32247(2) 0.42191(3) 0.01540(11) Uani 1 1 d . . . . .
C2 C 0.4074(4) 0.32281(10) 0.51891(19) 0.0219(5) Uani 1 1 d . . . . .
H2 H 0.5631 0.3262 0.4965 0.026 Uiso 1 1 calc R U . . .
C1 C 0.2655(4) 0.36949(10) 0.54244(17) 0.0183(4) Uani 1 1 d . . . . .
N3 N 0.8180(4) 0.47876(8) 0.72293(18) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.2879(5) 0.27114(10) 0.53237(19) 0.0256(5) Uani 1 1 d . . . . .
H3 H 0.3437 0.2314 0.5200 0.031 Uiso 1 1 calc R U . . .
O1 O 0.5237(3) 0.56570(8) 0.88151(14) 0.0305(4) Uani 1 1 d . . . . .
C7 C 0.1162(5) 0.32494(13) 0.2701(2) 0.0326(6) Uani 1 1 d . . . . .
H7 H 0.2718 0.3240 0.2471 0.039 Uiso 1 1 calc R U . . .
N2 N 0.7147(4) 0.45425(9) 0.63310(17) 0.0262(5) Uani 1 1 d . . . . .
C14 C 0.7083(4) 0.52492(10) 0.87695(19) 0.0219(5) Uani 1 1 d . . . . .
H14A H 0.7185 0.4957 0.9331 0.026 Uiso 1 1 calc R U . . .
H14B H 0.8650 0.5446 0.8863 0.026 Uiso 1 1 calc R U . . .
C10 C -0.2193(5) 0.35758(10) 0.32160(18) 0.0238(5) Uani 1 1 d . . . . .
H10 H -0.3409 0.3836 0.3421 0.029 Uiso 1 1 calc R U . . .
C9 C -0.2301(5) 0.29659(10) 0.31672(19) 0.0236(5) Uani 1 1 d . . . . .
H9 H -0.3608 0.2721 0.3334 0.028 Uiso 1 1 calc R U . . .
N1 N 0.4776(4) 0.45704(8) 0.62488(17) 0.0218(4) Uani 1 1 d . . . . .
C13 C 0.6437(4) 0.49695(9) 0.77115(19) 0.0190(5) Uani 1 1 d . . . . .
C8 C -0.0240(5) 0.27624(11) 0.2855(2) 0.0296(6) Uani 1 1 d . . . . .
H8 H 0.0160 0.2350 0.2754 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3331(5) 0.65573(10) 1.0738(2) 0.0275(5) Uani 1 1 d . . . . .
H19 H 0.1960 0.6776 1.0790 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0590(4) 0.34599(10) 0.57088(17) 0.0204(5) Uani 1 1 d . . . . .
H5 H -0.0725 0.3684 0.5918 0.024 Uiso 1 1 calc R U . . .
C6 C -0.0055(5) 0.37527(11) 0.29334(19) 0.0265(5) Uani 1 1 d . . . . .
H6 H 0.0499 0.4160 0.2897 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5389(5) 0.59403(10) 0.97529(19) 0.0224(5) Uani 1 1 d . . . . .
C12 C 0.4252(4) 0.48332(9) 0.7092(2) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.2714 0.4907 0.7226 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0726(5) 0.28495(10) 0.56403(17) 0.0238(5) Uani 1 1 d . . . . .
H4 H -0.0483 0.2568 0.5787 0.029 Uiso 1 1 calc R U . . .
C20 C 0.3372(5) 0.62673(10) 0.9816(2) 0.0259(5) Uani 1 1 d . . . . .
H20 H 0.2049 0.6290 0.9234 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3143(5) 0.43259(10) 0.5315(2) 0.0282(6) Uani 1 1 d . . . . .
H11A H 0.3851 0.4383 0.4694 0.034 Uiso 1 1 calc R U . . .
H11B H 0.1607 0.4539 0.5189 0.034 Uiso 1 1 calc R U . . .
C16 C 0.7341(5) 0.59149(10) 1.05959(19) 0.0244(5) Uani 1 1 d . . . . .
H16 H 0.8713 0.5694 1.0549 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5277(5) 0.65324(10) 1.1591(2) 0.0270(5) Uani 1 1 d . . . . .
H18 H 0.5229 0.6732 1.2221 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7268(5) 0.62168(10) 1.1515(2) 0.0274(5) Uani 1 1 d . . . . .
H17 H 0.8605 0.6204 1.2092 0.033 Uiso 1 1 calc R U . . .
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
C1 Fe1 C5 40.95(10) . .
C1 Fe1 C6 107.44(9) . .
C5 Fe1 C6 124.99(10) . .
C1 Fe1 C2 40.96(9) . .
C5 Fe1 C2 68.70(10) . .
C6 Fe1 C2 120.99(10) . .
C1 Fe1 C7 125.22(11) . .
C5 Fe1 C7 162.37(11) . .
C6 Fe1 C7 40.75(11) . .
C2 Fe1 C7 107.86(11) . .
C1 Fe1 C8 162.62(11) . .
C5 Fe1 C8 155.26(11) . .
C6 Fe1 C8 68.36(11) . .
C2 Fe1 C8 125.49(11) . .
C7 Fe1 C8 40.71(11) . .
C1 Fe1 C4 68.59(9) . .
C5 Fe1 C4 40.71(10) . .
C6 Fe1 C4 162.11(11) . .
C2 Fe1 C4 68.24(10) . .
C7 Fe1 C4 155.68(11) . .
C8 Fe1 C4 120.63(11) . .
C1 Fe1 C3 68.21(10) . .
C5 Fe1 C3 68.22(10) . .
C6 Fe1 C3 155.95(12) . .
C2 Fe1 C3 40.18(10) . .
C7 Fe1 C3 121.07(11) . .
C8 Fe1 C3 108.32(10) . .
C4 Fe1 C3 40.45(11) . .
C1 Fe1 C9 155.54(10) . .
C5 Fe1 C9 120.62(10) . .
C6 Fe1 C9 67.87(10) . .
C2 Fe1 C9 162.30(9) . .
C7 Fe1 C9 67.92(11) . .
C8 Fe1 C9 40.19(11) . .
C4 Fe1 C9 108.08(10) . .
C3 Fe1 C9 125.95(10) . .
C1 Fe1 C10 120.57(9) . .
C5 Fe1 C10 107.63(10) . .
C6 Fe1 C10 40.29(10) . .
C2 Fe1 C10 155.88(10) . .
C7 Fe1 C10 68.02(11) . .
C8 Fe1 C10 67.90(10) . .
C4 Fe1 C10 125.46(11) . .
C3 Fe1 C10 162.54(11) . .
C9 Fe1 C10 40.28(10) . .
C3 C2 C1 107.7(2) . .
C3 C2 Fe1 70.21(14) . .
C1 C2 Fe1 68.79(13) . .
C3 C2 H2 126.1 . .
C1 C2 H2 126.1 . .
Fe1 C2 H2 126.1 . .
C5 C1 C2 108.0(2) . .
C5 C1 C11 125.5(2) . .
C2 C1 C11 126.3(2) . .
C5 C1 Fe1 69.90(13) . .
C2 C1 Fe1 70.25(13) . .
C11 C1 Fe1 122.02(16) . .
N2 N3 C13 108.2(2) . .
C2 C3 C4 108.7(2) . .
C2 C3 Fe1 69.60(14) . .
C4 C3 Fe1 69.54(14) . .
C2 C3 H3 125.7 . .
C4 C3 H3 125.7 . .
Fe1 C3 H3 125.7 . .
C15 O1 C14 116.70(18) . .
C8 C7 C6 107.6(2) . .
C8 C7 Fe1 69.68(14) . .
C6 C7 Fe1 69.58(14) . .
C8 C7 H7 126.2 . .
C6 C7 H7 126.2 . .
Fe1 C7 H7 126.2 . .
N3 N2 N1 107.5(2) . .
O1 C14 C13 106.81(19) . .
O1 C14 H14A 110.4 . .
C13 C14 H14A 110.4 . .
O1 C14 H14B 110.4 . .
C13 C14 H14B 110.4 . .
H14A C14 H14B 108.6 . .
C6 C10 C9 108.1(2) . .
C6 C10 Fe1 69.42(14) . .
C9 C10 Fe1 69.83(13) . .
C6 C10 H10 126.0 . .
C9 C10 H10 126.0 . .
Fe1 C10 H10 126.0 . .
C8 C9 C10 108.4(2) . .
C8 C9 Fe1 69.59(14) . .
C10 C9 Fe1 69.89(13) . .
C8 C9 H9 125.8 . .
C10 C9 H9 125.8 . .
Fe1 C9 H9 125.8 . .
N2 N1 C12 111.0(2) . .
N2 N1 C11 119.7(2) . .
C12 N1 C11 129.3(2) . .
N3 C13 C12 108.9(2) . .
N3 C13 C14 120.2(2) . .
C12 C13 C14 130.9(2) . .
C9 C8 C7 107.9(2) . .
C9 C8 Fe1 70.22(14) . .
C7 C8 Fe1 69.61(14) . .
C9 C8 H8 126.0 . .
C7 C8 H8 126.0 . .
Fe1 C8 H8 126.0 . .
C20 C19 C18 120.8(2) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C4 C5 C1 107.8(2) . .
C4 C5 Fe1 70.08(13) . .
C1 C5 Fe1 69.15(13) . .
C4 C5 H5 126.1 . .
C1 C5 H5 126.1 . .
Fe1 C5 H5 126.1 . .
C10 C6 C7 108.0(2) . .
C10 C6 Fe1 70.29(13) . .
C7 C6 Fe1 69.67(14) . .
C10 C6 H6 126.0 . .
C7 C6 H6 126.0 . .
Fe1 C6 H6 126.0 . .
O1 C15 C16 124.7(2) . .
O1 C15 C20 114.7(2) . .
C16 C15 C20 120.6(2) . .
N1 C12 C13 104.4(2) . .
N1 C12 H12 127.8 . .
C13 C12 H12 127.8 . .
C3 C4 C5 107.8(2) . .
C3 C4 Fe1 70.01(14) . .
C5 C4 Fe1 69.21(13) . .
C3 C4 H4 126.1 . .
C5 C4 H4 126.1 . .
Fe1 C4 H4 126.1 . .
C19 C20 C15 119.0(2) . .
C19 C20 H20 120.5 . .
C15 C20 H20 120.5 . .
N1 C11 C1 113.12(19) . .
N1 C11 H11A 109.0 . .
C1 C11 H11A 109.0 . .
N1 C11 H11B 109.0 . .
C1 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C15 C16 C17 119.3(2) . .
C15 C16 H16 120.3 . .
C17 C16 H16 120.3 . .
C17 C18 C19 119.7(2) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
C18 C17 C16 120.6(2) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C1 2.028(2) .
Fe1 C5 2.038(2) .
Fe1 C6 2.046(2) .
Fe1 C2 2.047(2) .
Fe1 C7 2.047(3) .
Fe1 C8 2.048(2) .
Fe1 C4 2.049(2) .
Fe1 C3 2.055(2) .
Fe1 C9 2.057(3) .
Fe1 C10 2.058(2) .
C2 C3 1.409(4) .
C2 C1 1.426(3) .
C2 H2 1.0000 .
C1 C5 1.422(3) .
C1 C11 1.502(3) .
N3 N2 1.321(3) .
N3 C13 1.357(3) .
C3 C4 1.419(4) .
C3 H3 1.0000 .
O1 C15 1.374(3) .
O1 C14 1.429(3) .
C7 C8 1.425(4) .
C7 C6 1.425(4) .
C7 H7 1.0000 .
N2 N1 1.339(3) .
C14 C13 1.497(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C10 C6 1.413(4) .
C10 C9 1.417(3) .
C10 H10 1.0000 .
C9 C8 1.411(4) .
C9 H9 1.0000 .
N1 C12 1.347(3) .
N1 C11 1.478(3) .
C13 C12 1.370(3) .
C8 H8 1.0000 .
C19 C20 1.383(4) .
C19 C18 1.393(4) .
C19 H19 0.9500 .
C5 C4 1.422(3) .
C5 H5 1.0000 .
C6 H6 1.0000 .
C15 C16 1.388(3) .
C15 C20 1.399(3) .
C12 H12 0.9500 .
C4 H4 1.0000 .
C20 H20 0.9500 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C16 C17 1.397(3) .
C16 H16 0.9500 .
C18 C17 1.376(4) .
C18 H18 0.9500 .
C17 H17 0.9500 .
