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#$Date: 2021-11-29 11:43:43 +0200 (Mon, 29 Nov 2021) $
#$Revision: 270909 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/54/1565419.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_1565419
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 H18 Fe N4 O3'
_chemical_formula_weight         418.23
_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                 94.015(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.858(4)
_cell_length_b                   7.8241(14)
_cell_length_c                   10.398(2)
_cell_measurement_reflns_used    12325
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.77
_cell_volume                     1773.9(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20177
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.766
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.5196
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0297P)²+1.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3186
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            9.cif
_cod_data_source_block           1
_cod_original_cell_volume        1773.8(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1565419
_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   0.887
_shelx_estimated_absorpt_t_max   0.917
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 0.11536(2) 0.50989(3) 0.14528(2) 0.01860(9) Uani 1 1 d . . . . .
O1 O 0.45662(6) 0.58290(19) 0.15901(12) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.26914(6) 0.57705(19) -0.01697(14) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.50824(8) 0.5937(2) 0.23923(18) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.05853(8) 0.6660(2) 0.03505(17) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.0127 0.6677 0.0335 0.030 Uiso 1 1 calc R U . . .
N3 N 0.35207(7) 0.7231(2) 0.00286(15) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.16036(8) 0.7251(2) 0.08782(17) 0.0234(4) Uani 1 1 d . . . . .
H2 H 0.1987 0.7744 0.1311 0.028 Uiso 1 1 calc R U . . .
N2 N 0.30192(7) 0.6989(2) -0.07265(14) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.72334(6) 0.5784(2) 0.40825(17) 0.0481(4) Uani 1 1 d . . . . .
C18 C 0.61813(8) 0.6075(2) 0.38315(19) 0.0276(4) Uani 1 1 d . . . . .
C13 C 0.35086(8) 0.6171(2) 0.10605(17) 0.0235(4) Uani 1 1 d . . . . .
N4 N 0.67631(7) 0.6115(2) 0.46133(19) 0.0352(4) Uani 1 1 d . . . . .
O2 O 0.67614(7) 0.6486(2) 0.57588(16) 0.0478(4) Uani 1 1 d . . . . .
C1 C 0.15743(7) 0.5997(2) -0.01173(16) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.09433(7) 0.5630(2) -0.04449(16) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.0780 0.4800 -0.1116 0.027 Uiso 1 1 calc R U . . .
C14 C 0.39959(8) 0.6166(3) 0.21252(18) 0.0338(4) Uani 1 1 d . . . . .
H14A H 0.4011 0.7287 0.2567 0.041 Uiso 1 1 calc R U . . .
H14B H 0.3910 0.5273 0.2764 0.041 Uiso 1 1 calc R U . . .
C12 C 0.29790(8) 0.5239(2) 0.09426(18) 0.0258(4) Uani 1 1 d . . . . .
H12 H 0.2844 0.4400 0.1520 0.031 Uiso 1 1 calc R U . . .
C16 C 0.50938(8) 0.6366(3) 0.36776(19) 0.0354(5) Uani 1 1 d . . . . .
H16 H 0.4723 0.6617 0.4064 0.043 Uiso 1 1 calc R U . . .
C11 C 0.20997(8) 0.5246(3) -0.07792(18) 0.0280(4) Uani 1 1 d . . . . .
H11A H 0.2070 0.3983 -0.0760 0.034 Uiso 1 1 calc R U . . .
H11B H 0.2072 0.5611 -0.1693 0.034 Uiso 1 1 calc R U . . .
C17 C 0.56490(9) 0.6429(3) 0.4403(2) 0.0400(5) Uani 1 1 d . . . . .
H17 H 0.5661 0.6716 0.5292 0.048 Uiso 1 1 calc R U . . .
C10 C 0.15750(10) 0.2891(3) 0.2051(2) 0.0425(5) Uani 1 1 d . . . . .
H10 H 0.1928 0.2341 0.1650 0.051 Uiso 1 1 calc R U . . .
C20 C 0.56243(9) 0.5561(4) 0.1833(2) 0.0472(6) Uani 1 1 d . . . . .
H20 H 0.5615 0.5243 0.0950 0.057 Uiso 1 1 calc R U . . .
C8 C 0.06082(9) 0.3610(3) 0.2501(2) 0.0388(5) Uani 1 1 d . . . . .
H8 H 0.0150 0.3661 0.2477 0.047 Uiso 1 1 calc R U . . .
C6 C 0.16194(10) 0.4107(3) 0.3049(2) 0.0461(6) Uani 1 1 d . . . . .
H6 H 0.2008 0.4569 0.3481 0.055 Uiso 1 1 calc R U . . .
C3 C 0.09926(8) 0.7653(2) 0.11715(18) 0.0262(4) Uani 1 1 d . . . . .
H3A H 0.0872 0.8485 0.1838 0.031 Uiso 1 1 calc R U . . .
C9 C 0.09537(11) 0.2581(3) 0.1714(2) 0.0376(5) Uani 1 1 d . . . . .
H9 H 0.0786 0.1772 0.1033 0.045 Uiso 1 1 calc R U . . .
C19 C 0.61759(9) 0.5647(3) 0.2556(2) 0.0452(6) Uani 1 1 d . . . . .
H19 H 0.6549 0.5411 0.2172 0.054 Uiso 1 1 calc R U . . .
C7 C 0.10188(12) 0.4561(3) 0.33330(19) 0.0443(5) Uani 1 1 d . . . . .
H7 H 0.0905 0.5397 0.4003 0.053 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
C10 Fe1 C4 157.88(9) . .
C10 Fe1 C8 67.67(8) . .
C4 Fe1 C8 106.71(8) . .
C10 Fe1 C5 122.41(9) . .
C4 Fe1 C5 41.01(7) . .
C8 Fe1 C5 122.30(8) . .
C10 Fe1 C6 40.39(10) . .
C4 Fe1 C6 159.45(10) . .
C8 Fe1 C6 67.92(9) . .
C5 Fe1 C6 158.76(9) . .
C10 Fe1 C9 40.19(9) . .
C4 Fe1 C9 121.74(8) . .
C8 Fe1 C9 40.33(9) . .
C5 Fe1 C9 106.85(8) . .
C6 Fe1 C9 67.89(9) . .
C10 Fe1 C7 67.95(9) . .
C4 Fe1 C7 122.64(9) . .
C8 Fe1 C7 40.56(10) . .
C5 Fe1 C7 158.72(9) . .
C6 Fe1 C7 40.46(10) . .
C9 Fe1 C7 68.08(9) . .
C10 Fe1 C3 160.46(9) . .
C4 Fe1 C3 40.72(7) . .
C8 Fe1 C3 122.27(8) . .
C5 Fe1 C3 68.75(7) . .
C6 Fe1 C3 123.99(9) . .
C9 Fe1 C3 157.76(8) . .
C7 Fe1 C3 107.66(8) . .
C10 Fe1 C1 108.38(8) . .
C4 Fe1 C1 68.71(7) . .
C8 Fe1 C1 158.89(8) . .
C5 Fe1 C1 40.82(6) . .
C6 Fe1 C1 123.48(8) . .
C9 Fe1 C1 123.25(8) . .
C7 Fe1 C1 159.21(9) . .
C3 Fe1 C1 68.55(7) . .
C10 Fe1 C2 124.59(8) . .
C4 Fe1 C2 68.37(7) . .
C8 Fe1 C2 158.77(9) . .
C5 Fe1 C2 68.42(7) . .
C6 Fe1 C2 109.02(8) . .
C9 Fe1 C2 159.91(8) . .
C7 Fe1 C2 123.39(9) . .
C3 Fe1 C2 40.63(7) . .
C1 Fe1 C2 40.53(7) . .
C15 O1 C14 117.43(14) . .
C12 N1 N2 110.99(14) . .
C12 N1 C11 129.35(15) . .
N2 N1 C11 119.63(15) . .
O1 C15 C16 124.69(16) . .
O1 C15 C20 115.26(17) . .
C16 C15 C20 120.05(17) . .
C3 C4 C5 108.11(14) . .
C3 C4 Fe1 69.99(10) . .
C5 C4 Fe1 69.50(9) . .
C3 C4 H4 125.9 . .
C5 C4 H4 125.9 . .
Fe1 C4 H4 125.9 . .
N2 N3 C13 108.76(14) . .
C1 C2 C3 108.20(15) . .
C1 C2 Fe1 69.48(10) . .
C3 C2 Fe1 69.18(10) . .
C1 C2 H2 125.9 . .
C3 C2 H2 125.9 . .
Fe1 C2 H2 125.9 . .
N3 N2 N1 106.94(14) . .
C19 C18 C17 121.33(17) . .
C19 C18 N4 119.55(17) . .
C17 C18 N4 119.10(18) . .
N3 C13 C12 108.57(16) . .
N3 C13 C14 122.64(16) . .
C12 C13 C14 128.73(17) . .
O2 N4 O3 123.09(17) . .
O2 N4 C18 118.95(17) . .
O3 N4 C18 117.95(18) . .
C2 C1 C5 107.79(15) . .
C2 C1 C11 127.35(15) . .
C5 C1 C11 124.77(15) . .
C2 C1 Fe1 69.99(10) . .
C5 C1 Fe1 69.00(9) . .
C11 C1 Fe1 129.12(13) . .
C1 C5 C4 107.96(15) . .
C1 C5 Fe1 70.18(9) . .
C4 C5 Fe1 69.49(9) . .
C1 C5 H5 126.0 . .
C4 C5 H5 126.0 . .
Fe1 C5 H5 126.0 . .
O1 C14 C13 108.15(15) . .
O1 C14 H14A 110.1 . .
C13 C14 H14A 110.1 . .
O1 C14 H14B 110.1 . .
C13 C14 H14B 110.1 . .
H14A C14 H14B 108.4 . .
N1 C12 C13 104.73(15) . .
N1 C12 H12 127.6 . .
C13 C12 H12 127.6 . .
C15 C16 C17 119.55(18) . .
C15 C16 H16 120.2 . .
C17 C16 H16 120.2 . .
N1 C11 C1 111.99(14) . .
N1 C11 H11A 109.2 . .
C1 C11 H11A 109.2 . .
N1 C11 H11B 109.2 . .
C1 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C18 C17 C16 119.66(19) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C9 C10 C6 108.52(19) . .
C9 C10 Fe1 70.11(11) . .
C6 C10 Fe1 69.97(12) . .
C9 C10 H10 125.7 . .
C6 C10 H10 125.7 . .
Fe1 C10 H10 125.7 . .
C19 C20 C15 120.1(2) . .
C19 C20 H20 119.9 . .
C15 C20 H20 119.9 . .
C9 C8 C7 108.29(19) . .
C9 C8 Fe1 69.94(11) . .
C7 C8 Fe1 69.88(12) . .
C9 C8 H8 125.9 . .
C7 C8 H8 125.9 . .
Fe1 C8 H8 125.9 . .
C10 C6 C7 107.90(19) . .
C10 C6 Fe1 69.64(12) . .
C7 C6 Fe1 69.86(11) . .
C10 C6 H6 126.0 . .
C7 C6 H6 126.0 . .
Fe1 C6 H6 126.0 . .
C4 C3 C2 107.95(16) . .
C4 C3 Fe1 69.29(10) . .
C2 C3 Fe1 70.19(10) . .
C4 C3 H3A 126.0 . .
C2 C3 H3A 126.0 . .
Fe1 C3 H3A 126.0 . .
C10 C9 C8 107.84(19) . .
C10 C9 Fe1 69.70(12) . .
C8 C9 Fe1 69.73(12) . .
C10 C9 H9 126.1 . .
C8 C9 H9 126.1 . .
Fe1 C9 H9 126.1 . .
C18 C19 C20 119.28(19) . .
C18 C19 H19 120.4 . .
C20 C19 H19 120.4 . .
C6 C7 C8 107.4(2) . .
C6 C7 Fe1 69.68(12) . .
C8 C7 Fe1 69.56(11) . .
C6 C7 H7 126.3 . .
C8 C7 H7 126.3 . .
Fe1 C7 H7 126.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C10 2.034(2) .
Fe1 C4 2.0371(17) .
Fe1 C8 2.0371(19) .
Fe1 C5 2.0372(17) .
Fe1 C6 2.0388(19) .
Fe1 C9 2.040(2) .
Fe1 C7 2.041(2) .
Fe1 C3 2.0462(18) .
Fe1 C1 2.0530(17) .
Fe1 C2 2.0596(17) .
O1 C15 1.358(2) .
O1 C14 1.425(2) .
N1 C12 1.343(2) .
N1 N2 1.347(2) .
N1 C11 1.459(2) .
C15 C16 1.377(3) .
C15 C20 1.387(3) .
C4 C3 1.421(3) .
C4 C5 1.427(3) .
C4 H4 1.0000 .
N3 N2 1.317(2) .
N3 C13 1.358(2) .
C2 C1 1.424(2) .
C2 C3 1.425(2) .
C2 H2 1.0000 .
O3 N4 1.228(2) .
C18 C19 1.367(3) .
C18 C17 1.371(3) .
C18 N4 1.461(2) .
C13 C12 1.367(2) .
C13 C14 1.482(2) .
N4 O2 1.226(2) .
C1 C5 1.427(2) .
C1 C11 1.499(2) .
C5 H5 1.0000 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C12 H12 0.9500 .
C16 C17 1.384(3) .
C16 H16 0.9500 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C17 H17 0.9500 .
C10 C9 1.400(3) .
C10 C6 1.406(4) .
C10 H10 1.0000 .
C20 C19 1.377(3) .
C20 H20 0.9500 .
C8 C9 1.405(3) .
C8 C7 1.414(3) .
C8 H8 1.0000 .
C6 C7 1.411(3) .
C6 H6 1.0000 .
C3 H3A 1.0000 .
C9 H9 1.0000 .
C19 H19 0.9500 .
C7 H7 1.0000 .
