#------------------------------------------------------------------------------
#$Date: 2021-10-06 19:06:00 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060920.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_7060920
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 H13 Fe N2 O P'
_chemical_formula_weight         312.08
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-04 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.718(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6640(8)
_cell_length_b                   7.3497(5)
_cell_length_c                   15.3627(10)
_cell_measurement_reflns_used    27273
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1316.40(15)
_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 0.997
_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  0.0408
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27273
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.225
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.258
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4410
_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    1.575
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.509
_exptl_crystal_size_min          0.376
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0357(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.5209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2763
_reflns_number_total             3028
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02666f2.cif
_cod_data_source_block           me180521Fe1
_cod_depositor_comments
'Adding full bibliography for 7060916--7060926.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060920
_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.
;
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.591
;
loop_
_space_group_symop_operation_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_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 0.76457(2) 0.45668(3) 0.54475(2) 0.01533(10) Uani 1 1 d . . . . .
P1 P 0.46938(4) 0.58168(7) 0.80045(3) 0.02754(14) Uani 1 1 d . . . . .
O1 O 0.30127(12) 0.8844(2) 0.78191(10) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.46578(12) 0.7670(2) 0.73277(9) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.72940(13) 0.6417(2) 0.63861(10) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.55416(11) 0.78559(19) 0.67685(9) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.6891(19) 0.806(3) 0.5260(14) 0.032(6) Uiso 1 1 d . . . . .
C2 C 0.74688(15) 0.7318(2) 0.55768(11) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.85922(16) 0.6896(2) 0.53089(12) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.8941(19) 0.731(3) 0.4781(14) 0.034(6) Uiso 1 1 d . . . . .
C4 C 0.91172(15) 0.5741(3) 0.59473(13) 0.0248(4) Uani 1 1 d . . . . .
H4 H 0.987(2) 0.522(3) 0.5931(16) 0.034(6) Uiso 1 1 d . . . . .
C5 C 0.83206(15) 0.5439(2) 0.66148(12) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.847(2) 0.477(3) 0.7103(17) 0.033(6) Uiso 1 1 d . . . . .
C6 C 0.62530(14) 0.6481(2) 0.68982(10) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.37840(15) 0.9006(2) 0.73171(12) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.59415(17) 0.5213(2) 0.75471(12) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.6376 0.4163 0.7704 0.030 Uiso 1 1 calc R U . . .
C9 C 0.38952(18) 1.0527(3) 0.66815(15) 0.0323(4) Uani 1 1 d . . . . .
H9A H 0.4006 1.0027 0.6099 0.048 Uiso 1 1 calc R U . . .
H9B H 0.4556 1.1284 0.6852 0.048 Uiso 1 1 calc R U . . .
H9C H 0.3197 1.1268 0.6676 0.048 Uiso 1 1 calc R U . . .
C10 C 0.61778(16) 0.3119(3) 0.52016(14) 0.0303(4) Uani 1 1 d . . . . .
H10 H 0.546(2) 0.333(4) 0.5420(16) 0.044(7) Uiso 1 1 d . . . . .
C11 C 0.66126(17) 0.3806(3) 0.44170(13) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.626(2) 0.462(4) 0.4032(18) 0.044(7) Uiso 1 1 d . . . . .
C12 C 0.77287(16) 0.3081(2) 0.43208(12) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.8233(19) 0.335(3) 0.3850(15) 0.036(6) Uiso 1 1 d . . . . .
C13 C 0.79886(17) 0.1964(2) 0.50507(13) 0.0275(4) Uani 1 1 d . . . . .
H13 H 0.8654(19) 0.133(3) 0.5151(14) 0.030(6) Uiso 1 1 d . . . . .
C14 C 0.70265(18) 0.1986(2) 0.55966(13) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.7002(19) 0.135(3) 0.6108(15) 0.033(6) Uiso 1 1 d . . . . .
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'
P P 0.1023 0.0942 '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
C1 Fe1 C11 127.38(7) . . ?
C1 Fe1 C5 41.15(6) . . ?
C11 Fe1 C5 166.47(8) . . ?
C1 Fe1 C10 107.09(7) . . ?
C11 Fe1 C10 40.57(8) . . ?
C5 Fe1 C10 128.74(8) . . ?
C1 Fe1 C2 41.04(6) . . ?
C11 Fe1 C2 106.73(7) . . ?
C5 Fe1 C2 68.96(7) . . ?
C10 Fe1 C2 116.57(8) . . ?
C1 Fe1 C14 117.48(7) . . ?
C11 Fe1 C14 68.29(8) . . ?
C5 Fe1 C14 108.74(8) . . ?
C10 Fe1 C14 40.55(8) . . ?
C2 Fe1 C14 150.48(8) . . ?
C1 Fe1 C4 68.73(7) . . ?
C11 Fe1 C4 151.06(8) . . ?
C5 Fe1 C4 40.69(7) . . ?
C10 Fe1 C4 167.69(8) . . ?
C2 Fe1 C4 68.45(7) . . ?
C14 Fe1 C4 130.03(8) . . ?
C1 Fe1 C13 151.66(7) . . ?
C11 Fe1 C13 68.24(8) . . ?
C5 Fe1 C13 118.74(7) . . ?
C10 Fe1 C13 68.21(8) . . ?
C2 Fe1 C13 166.75(7) . . ?
C14 Fe1 C13 40.61(8) . . ?
C4 Fe1 C13 109.60(8) . . ?
C1 Fe1 C12 166.00(7) . . ?
C11 Fe1 C12 40.58(8) . . ?
C5 Fe1 C12 151.92(7) . . ?
C10 Fe1 C12 68.10(8) . . ?
C2 Fe1 C12 128.05(7) . . ?
C14 Fe1 C12 68.08(8) . . ?
C4 Fe1 C12 118.69(7) . . ?
C13 Fe1 C12 40.37(8) . . ?
C1 Fe1 C3 68.66(7) . . ?
C11 Fe1 C3 117.11(8) . . ?
C5 Fe1 C3 68.56(7) . . ?
C10 Fe1 C3 150.07(8) . . ?
C2 Fe1 C3 40.57(7) . . ?
C14 Fe1 C3 168.12(8) . . ?
C4 Fe1 C3 40.57(8) . . ?
C13 Fe1 C3 129.58(8) . . ?
C12 Fe1 C3 108.50(7) . . ?
C7 P1 N1 87.85(8) . . ?
N2 N1 C8 118.62(14) . . ?
N2 N1 P1 117.09(11) . . ?
C8 N1 P1 124.29(12) . . ?
C2 C1 C5 107.83(14) . . ?
C2 C1 C6 126.43(15) . . ?
C5 C1 C6 125.74(15) . . ?
C2 C1 Fe1 69.85(9) . . ?
C5 C1 Fe1 69.70(9) . . ?
C6 C1 Fe1 126.13(11) . . ?
C6 N2 N1 108.11(13) . . ?
C3 C2 C1 107.95(15) . . ?
C3 C2 Fe1 70.05(10) . . ?
C1 C2 Fe1 69.10(9) . . ?
C3 C2 H2 127.1(13) . . ?
C1 C2 H2 124.9(13) . . ?
Fe1 C2 H2 124.7(13) . . ?
C2 C3 C4 108.22(16) . . ?
C2 C3 Fe1 69.38(9) . . ?
C4 C3 Fe1 69.64(10) . . ?
C2 C3 H3 126.2(13) . . ?
C4 C3 H3 125.6(14) . . ?
Fe1 C3 H3 126.1(14) . . ?
C5 C4 C3 108.27(15) . . ?
C5 C4 Fe1 69.29(10) . . ?
C3 C4 Fe1 69.79(10) . . ?
C5 C4 H4 125.0(15) . . ?
C3 C4 H4 126.7(15) . . ?
Fe1 C4 H4 125.3(15) . . ?
C4 C5 C1 107.73(15) . . ?
C4 C5 Fe1 70.02(10) . . ?
C1 C5 Fe1 69.15(9) . . ?
C4 C5 H5 124.6(15) . . ?
C1 C5 H5 127.6(15) . . ?
Fe1 C5 H5 127.8(15) . . ?
N2 C6 C7 115.85(15) . . ?
N2 C6 C1 118.06(14) . . ?
C7 C6 C1 126.07(15) . . ?
O1 C8 N1 118.29(18) . . ?
O1 C8 C9 124.92(18) . . ?
N1 C8 C9 116.79(15) . . ?
C6 C7 P1 111.11(13) . . ?
C6 C7 H7 124.4 . . ?
P1 C7 H7 124.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C14 108.12(17) . . ?
C11 C10 Fe1 69.61(10) . . ?
C14 C10 Fe1 69.84(11) . . ?
C11 C10 H10 127.1(16) . . ?
C14 C10 H10 124.8(16) . . ?
Fe1 C10 H10 127.7(16) . . ?
C10 C11 C12 107.96(17) . . ?
C10 C11 Fe1 69.82(11) . . ?
C12 C11 Fe1 70.18(10) . . ?
C10 C11 H11 127.3(18) . . ?
C12 C11 H11 124.7(18) . . ?
Fe1 C11 H11 124.1(17) . . ?
C13 C12 C11 108.10(17) . . ?
C13 C12 Fe1 69.80(10) . . ?
C11 C12 Fe1 69.24(10) . . ?
C13 C12 H12 126.2(14) . . ?
C11 C12 H12 125.6(14) . . ?
Fe1 C12 H12 124.7(14) . . ?
C12 C13 C14 107.86(17) . . ?
C12 C13 Fe1 69.84(10) . . ?
C14 C13 Fe1 69.47(10) . . ?
C12 C13 H13 126.1(14) . . ?
C14 C13 H13 126.1(14) . . ?
Fe1 C13 H13 126.6(15) . . ?
C10 C14 C13 107.95(17) . . ?
C10 C14 Fe1 69.60(10) . . ?
C13 C14 Fe1 69.93(10) . . ?
C10 C14 H14 129.0(15) . . ?
C13 C14 H14 123.1(15) . . ?
Fe1 C14 H14 126.2(15) . . ?
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 C1 2.0327(16) . ?
Fe1 C11 2.0388(18) . ?
Fe1 C5 2.0400(17) . ?
Fe1 C10 2.0415(18) . ?
Fe1 C2 2.0427(16) . ?
Fe1 C14 2.0447(18) . ?
Fe1 C4 2.0496(18) . ?
Fe1 C13 2.0508(17) . ?
Fe1 C12 2.0513(17) . ?
Fe1 C3 2.0515(17) . ?
P1 C7 1.694(2) . ?
P1 N1 1.7130(15) . ?
O1 C8 1.208(2) . ?
N1 N2 1.3684(18) . ?
N1 C8 1.415(2) . ?
C1 C2 1.429(2) . ?
C1 C5 1.431(2) . ?
C1 C6 1.467(2) . ?
N2 C6 1.319(2) . ?
C2 C3 1.419(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.422(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.422(3) . ?
C4 H4 0.95(3) . ?
C5 H5 0.91(3) . ?
C6 C7 1.420(2) . ?
C8 C9 1.492(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.415(3) . ?
C10 C14 1.416(3) . ?
C10 H10 0.92(3) . ?
C11 C12 1.418(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.415(3) . ?
C12 H12 0.97(2) . ?
C13 C14 1.421(3) . ?
C13 H13 0.91(2) . ?
C14 H14 0.92(2) . ?
