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#$Date: 2021-10-06 19:06:00 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060925.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_7060925
loop_
_publ_author_name
'Kozáček, Pavel'
'Dostál, Libor'
'Hejda, Martin'
'Mikysek, Tomáš'
'R°užička, Aleš'
'Erben, Milan'
_publ_section_title
;
 Synthesis and properties of 1,2,3-diazapnictol-5-yl substituted
 ferrocenes
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18171
_journal_page_last               18182
_journal_paper_doi               10.1039/D1NJ02666F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_sum            'C14 H16 Fe N2 O'
_chemical_formula_weight         284.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3414(11)
_cell_length_b                   7.8369(5)
_cell_length_c                   19.8330(10)
_cell_measurement_reflns_used    23544
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2539.9(3)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1419
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.402
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0473
_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)+(0.0366P)²+2.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1879
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02666f2.cif
_cod_data_source_block           me181127Fe1
_cod_depositor_comments
'Adding full bibliography for 7060916--7060926.cif.'
_cod_original_formula_sum        'C14 H16 Fe1 N2 O1'
_cod_database_code               7060925
_shelx_shelxl_version_number     2017/1
_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.
;
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.703
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.39869(3) 0.38264(6) 0.34706(2) 0.01859(14) Uani 1 1 d . . . . .
N1 N 0.28722(15) 0.3103(3) 0.52622(11) 0.0175(6) Uani 1 1 d . . . . .
O1 O 0.16240(13) 0.3642(3) 0.61235(11) 0.0268(5) Uani 1 1 d . . . . .
C1 C 0.38200(18) 0.4134(4) 0.44830(13) 0.0176(7) Uani 1 1 d . . . . .
C2 C 0.46525(19) 0.4496(4) 0.42886(14) 0.0213(7) Uani 1 1 d . . . . .
H2 H 0.515439 0.390707 0.445895 0.026 Uiso 1 1 calc R U . . .
N2 N 0.26066(15) 0.1875(3) 0.57171(11) 0.0183(6) Uani 1 1 d . . . . .
H2A H 0.285183 0.087716 0.574347 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4629(2) 0.5867(4) 0.38205(14) 0.0248(8) Uani 1 1 d . . . . .
H3 H 0.511503 0.639406 0.359577 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3807(2) 0.6346(4) 0.37177(16) 0.0291(8) Uani 1 1 d . . . . .
H4 H 0.361050 0.726018 0.340539 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3302(2) 0.5278(4) 0.41280(15) 0.0250(8) Uani 1 1 d . . . . .
H5 H 0.269060 0.531287 0.415258 0.030 Uiso 1 1 calc R U . . .
C6 C 0.35583(19) 0.2806(4) 0.49636(14) 0.0185(7) Uani 1 1 d . . . . .
C8 C 0.16925(19) 0.0814(4) 0.65694(15) 0.0255(7) Uani 1 1 d . . . . .
H8A H 0.124177 0.120616 0.685616 0.038 Uiso 1 1 calc R U . . .
H8B H 0.215164 0.045095 0.685305 0.038 Uiso 1 1 calc R U . . .
H8C H 0.150729 -0.014886 0.629354 0.038 Uiso 1 1 calc R U . . .
C7 C 0.19638(19) 0.2247(4) 0.61174(14) 0.0199(7) Uani 1 1 d . . . . .
C9 C 0.4098(2) 0.1282(4) 0.50788(16) 0.0317(8) Uani 1 1 d . . . . .
H9A H 0.458730 0.137395 0.479532 0.048 Uiso 1 1 calc R U . . .
H9B H 0.379844 0.024004 0.496222 0.048 Uiso 1 1 calc R U . . .
H9C H 0.426073 0.123843 0.555414 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3750(3) 0.1333(5) 0.32499(18) 0.0403(10) Uani 1 1 d . . . . .
H10 H 0.355476 0.044473 0.357426 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4578(2) 0.1739(4) 0.31064(16) 0.0332(9) Uani 1 1 d . . . . .
H11 H 0.506976 0.118380 0.331156 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4587(2) 0.3062(4) 0.26206(14) 0.0284(8) Uani 1 1 d . . . . .
H12 H 0.508667 0.361001 0.242569 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3766(2) 0.3484(5) 0.24605(16) 0.0348(9) Uani 1 1 d . . . . .
H13 H 0.358203 0.437844 0.213430 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3251(2) 0.2406(5) 0.28533(17) 0.0424(10) Uani 1 1 d . . . . .
H14 H 0.263924 0.241754 0.285234 0.051 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'
Fe Fe 0.3463 0.8444 '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'
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
_geom_angle_publ_flag
C2 Fe1 C11 103.79(14) . . ?
C2 Fe1 C3 40.98(12) . . ?
C11 Fe1 C3 120.57(15) . . ?
C2 Fe1 C10 121.53(15) . . ?
C11 Fe1 C10 40.78(15) . . ?
C3 Fe1 C10 157.53(16) . . ?
C2 Fe1 C1 41.58(11) . . ?
C11 Fe1 C1 120.54(13) . . ?
C3 Fe1 C1 68.94(12) . . ?
C10 Fe1 C1 107.39(13) . . ?
C2 Fe1 C12 118.71(13) . . ?
C11 Fe1 C12 40.68(13) . . ?
C3 Fe1 C12 105.34(13) . . ?
C10 Fe1 C12 68.45(14) . . ?
C1 Fe1 C12 155.77(13) . . ?
C2 Fe1 C14 159.64(15) . . ?
C11 Fe1 C14 68.20(16) . . ?
C3 Fe1 C14 159.23(15) . . ?
C10 Fe1 C14 40.41(16) . . ?
C1 Fe1 C14 125.07(13) . . ?
C12 Fe1 C14 68.18(14) . . ?
C2 Fe1 C13 155.67(13) . . ?
C11 Fe1 C13 68.39(14) . . ?
C3 Fe1 C13 121.75(14) . . ?
C10 Fe1 C13 68.41(15) . . ?
C1 Fe1 C13 162.17(13) . . ?
C12 Fe1 C13 40.54(13) . . ?
C14 Fe1 C13 40.66(14) . . ?
C2 Fe1 C4 68.68(13) . . ?
C11 Fe1 C4 157.80(14) . . ?
C3 Fe1 C4 40.32(13) . . ?
C10 Fe1 C4 160.79(15) . . ?
C1 Fe1 C4 68.47(12) . . ?
C12 Fe1 C4 123.21(13) . . ?
C14 Fe1 C4 125.55(16) . . ?
C13 Fe1 C4 109.45(15) . . ?
C2 Fe1 C5 69.00(13) . . ?
C11 Fe1 C5 158.02(13) . . ?
C3 Fe1 C5 68.33(13) . . ?
C10 Fe1 C5 124.16(14) . . ?
C1 Fe1 C5 40.52(11) . . ?
C12 Fe1 C5 161.06(13) . . ?
C14 Fe1 C5 111.07(15) . . ?
C13 Fe1 C5 126.42(14) . . ?
C4 Fe1 C5 40.65(12) . . ?
C6 N1 N2 116.4(2) . . ?
C5 C1 C2 107.8(3) . . ?
C5 C1 C6 126.4(3) . . ?
C2 C1 C6 125.8(3) . . ?
C5 C1 Fe1 70.51(16) . . ?
C2 C1 Fe1 68.53(15) . . ?
C6 C1 Fe1 126.3(2) . . ?
C3 C2 C1 107.4(3) . . ?
C3 C2 Fe1 69.97(18) . . ?
C1 C2 Fe1 69.88(16) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Fe1 C2 H2 126.3 . . ?
C7 N2 N1 118.4(3) . . ?
C7 N2 H2A 120.8 . . ?
N1 N2 H2A 120.8 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 Fe1 70.6(2) . . ?
C2 C3 Fe1 69.05(18) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 125.6 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 Fe1 69.04(19) . . ?
C5 C4 Fe1 69.88(18) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 107.9(3) . . ?
C1 C5 Fe1 68.97(17) . . ?
C4 C5 Fe1 69.47(18) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
N1 C6 C1 115.0(3) . . ?
N1 C6 C9 125.7(3) . . ?
C1 C6 C9 119.3(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C7 N2 123.5(3) . . ?
O1 C7 C8 121.8(3) . . ?
N2 C7 C8 114.8(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C10 C11 107.8(3) . . ?
C14 C10 Fe1 70.0(2) . . ?
C11 C10 Fe1 69.3(2) . . ?
C14 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
Fe1 C10 H10 126.1 . . ?
C12 C11 C10 108.1(4) . . ?
C12 C11 Fe1 69.94(19) . . ?
C10 C11 Fe1 69.9(2) . . ?
C12 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
Fe1 C11 H11 126.0 . . ?
C11 C12 C13 108.3(3) . . ?
C11 C12 Fe1 69.38(18) . . ?
C13 C12 Fe1 70.23(18) . . ?
C11 C12 H12 125.9 . . ?
C13 C12 H12 125.9 . . ?
Fe1 C12 H12 125.9 . . ?
C12 C13 C14 107.3(3) . . ?
C12 C13 Fe1 69.23(17) . . ?
C14 C13 Fe1 69.36(18) . . ?
C12 C13 H13 126.3 . . ?
C14 C13 H13 126.3 . . ?
Fe1 C13 H13 126.3 . . ?
C10 C14 C13 108.5(3) . . ?
C10 C14 Fe1 69.6(2) . . ?
C13 C14 Fe1 69.97(19) . . ?
C10 C14 H14 125.7 . . ?
C13 C14 H14 125.7 . . ?
Fe1 C14 H14 125.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C2 2.022(3) . ?
Fe1 C11 2.033(3) . ?
Fe1 C3 2.035(3) . ?
Fe1 C10 2.040(4) . ?
Fe1 C1 2.041(3) . ?
Fe1 C12 2.040(3) . ?
Fe1 C14 2.045(3) . ?
Fe1 C13 2.053(3) . ?
Fe1 C4 2.056(3) . ?
Fe1 C5 2.061(3) . ?
N1 C6 1.289(4) . ?
N1 N2 1.389(3) . ?
O1 C7 1.226(4) . ?
C1 C5 1.421(4) . ?
C1 C2 1.442(4) . ?
C1 C6 1.474(4) . ?
C2 C3 1.420(4) . ?
C2 H2 1.0000 . ?
N2 C7 1.349(4) . ?
N2 H2A 0.8800 . ?
C3 C4 1.410(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.430(4) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 C9 1.502(4) . ?
C8 C7 1.504(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C14 1.411(5) . ?
C10 C11 1.419(5) . ?
C10 H10 1.0000 . ?
C11 C12 1.416(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.418(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.424(5) . ?
C13 H13 1.0000 . ?
C14 H14 1.0000 . ?
