#------------------------------------------------------------------------------
#$Date: 2020-07-06 06:06:31 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253896 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/46/7704657.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_7704657
loop_
_publ_author_name
'Navrátil, Michal'
'Faria, Erica N.'
'Panahy, Geve'
'Císařová, Ivana'
'Goicoechea, Jose M.'
'Štěpnička, Petr'
_publ_section_title
;
 Novel ferrocenyl functionalised phosphinecarboxamides: synthesis,
 characterisation and coordination.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8645
_journal_page_last               8651
_journal_paper_doi               10.1039/d0dt01908a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 Fe N O P'
_chemical_formula_sum            'C12 H14 Fe N O P'
_chemical_formula_weight         275.06
_chemical_name_systematic
;
 PH2C(O)NHCH2[Fe]
;
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6692(2)
_cell_length_b                   9.2447(2)
_cell_length_c                   25.8542(6)
_cell_measurement_reflns_used    4566
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      76.2310
_cell_measurement_theta_min      5.6840
_cell_volume                     2311.08(9)
_computing_cell_refinement
;
'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
;
_computing_data_collection
;
'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
;
_computing_data_reduction
;
'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
;
_computing_molecular_graphics    'WinGX (Farrugia, 2005)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4102
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11413
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.372
_diffrn_reflns_theta_min         5.714
_exptl_absorpt_coefficient_mu    11.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0278
_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)+(0.0335P)²+1.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2130
_reflns_number_total             2400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01908a2.cif
_cod_data_source_block           compound_2
_cod_depositor_comments
'Adding full bibliography for 7704652--7704657.cif.'
_cod_database_code               7704657
_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   0.259
_shelx_estimated_absorpt_t_max   0.655
_shelxl_version_number           2013-4
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 0.98474(3) 0.01471(3) 0.33483(2) 0.01715(10) Uani 1 1 d . . . . .
P1 P 0.60469(6) 0.01464(5) 0.57044(2) 0.02660(13) Uani 1 1 d . . . . .
H1 H 0.483(3) 0.068(4) 0.5626(13) 0.055(9) Uiso 1 1 d . . . . .
H2 H 0.580(3) -0.110(3) 0.5439(12) 0.051(8) Uiso 1 1 d . . . . .
C1 C 0.69111(19) 0.1164(2) 0.51709(7) 0.0200(4) Uani 1 1 d . . . . .
O1 O 0.67685(17) 0.24826(15) 0.51520(6) 0.0320(3) Uani 1 1 d . . . . .
N1 N 0.77041(17) 0.04015(17) 0.48489(6) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.778(3) -0.047(3) 0.4888(10) 0.028(6) Uiso 1 1 d . . . . .
C2 C 0.8468(2) 0.1065(2) 0.44169(7) 0.0236(4) Uani 1 1 d . . . . .
H2A H 0.934(3) 0.150(2) 0.4548(9) 0.022(5) Uiso 1 1 d . . . . .
H2B H 0.792(3) 0.188(3) 0.4280(10) 0.032(7) Uiso 1 1 d . . . . .
C3 C 0.87138(19) -0.00533(19) 0.40100(7) 0.0207(4) Uani 1 1 d . . . . .
C4 C 0.78689(19) -0.0332(2) 0.35663(8) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.7055 0.0181 0.3473 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8459(2) -0.1509(2) 0.32890(8) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.8113 -0.1912 0.2977 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9658(2) -0.1976(2) 0.35607(8) 0.0253(4) Uani 1 1 d . . . . .
H6 H 1.0252 -0.2747 0.3462 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9810(2) -0.1082(2) 0.40068(7) 0.0230(4) Uani 1 1 d . . . . .
H7 H 1.0521 -0.1160 0.4259 0.028 Uiso 1 1 calc R U . . .
C8 C 1.0228(2) 0.2289(2) 0.32138(8) 0.0241(4) Uani 1 1 d . . . . .
H8 H 0.9789 0.3082 0.3380 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9771(2) 0.1604(2) 0.27537(8) 0.0273(4) Uani 1 1 d . . . . .
H9 H 0.8975 0.1856 0.2559 0.033 Uiso 1 1 calc R U . . .
C10 C 1.0713(3) 0.0477(2) 0.26371(8) 0.0355(5) Uani 1 1 d . . . . .
H10 H 1.0660 -0.0158 0.2349 0.043 Uiso 1 1 calc R U . . .
C11 C 1.1757(2) 0.0461(2) 0.30289(10) 0.0370(5) Uani 1 1 d . . . . .
H11 H 1.2517 -0.0188 0.3049 0.044 Uiso 1 1 calc R U . . .
C12 C 1.1452(2) 0.1591(2) 0.33836(9) 0.0298(4) Uani 1 1 d . . . . .
H12 H 1.1975 0.1835 0.3682 0.036 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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
C3 Fe1 C5 69.00(7) . . ?
C3 Fe1 C4 41.05(8) . . ?
C5 Fe1 C4 40.76(8) . . ?
C3 Fe1 C10 171.20(10) . . ?
C5 Fe1 C10 108.27(9) . . ?
C4 Fe1 C10 131.62(10) . . ?
C3 Fe1 C11 146.85(10) . . ?
C5 Fe1 C11 132.08(9) . . ?
C4 Fe1 C11 171.28(10) . . ?
C10 Fe1 C11 40.97(11) . . ?
C3 Fe1 C8 109.12(8) . . ?
C5 Fe1 C8 146.30(8) . . ?
C4 Fe1 C8 115.18(8) . . ?
C10 Fe1 C8 68.18(8) . . ?
C11 Fe1 C8 68.33(8) . . ?
C3 Fe1 C9 132.13(8) . . ?
C5 Fe1 C9 114.42(8) . . ?
C4 Fe1 C9 108.44(8) . . ?
C10 Fe1 C9 40.53(9) . . ?
C11 Fe1 C9 68.61(9) . . ?
C8 Fe1 C9 40.59(8) . . ?
C3 Fe1 C6 68.89(8) . . ?
C5 Fe1 C6 40.72(8) . . ?
C4 Fe1 C6 68.55(8) . . ?
C10 Fe1 C6 114.92(8) . . ?
C11 Fe1 C6 109.00(9) . . ?
C8 Fe1 C6 172.33(8) . . ?
C9 Fe1 C6 146.10(8) . . ?
C3 Fe1 C7 40.79(7) . . ?
C5 Fe1 C7 68.57(8) . . ?
C4 Fe1 C7 68.52(8) . . ?
C10 Fe1 C7 146.98(9) . . ?
C11 Fe1 C7 115.52(9) . . ?
C8 Fe1 C7 133.05(8) . . ?
C9 Fe1 C7 171.91(8) . . ?
C6 Fe1 C7 40.78(8) . . ?
C3 Fe1 C12 115.39(8) . . ?
C5 Fe1 C12 171.78(8) . . ?
C4 Fe1 C12 146.94(9) . . ?
C10 Fe1 C12 68.44(9) . . ?
C11 Fe1 C12 40.64(9) . . ?
C8 Fe1 C12 40.53(8) . . ?
C9 Fe1 C12 68.39(8) . . ?
C6 Fe1 C12 132.91(8) . . ?
C7 Fe1 C12 109.76(8) . . ?
C1 P1 H1 95.6(15) . . ?
C1 P1 H2 97.6(13) . . ?
H1 P1 H2 95(2) . . ?
O1 C1 N1 124.38(17) . . ?
O1 C1 P1 118.65(15) . . ?
N1 C1 P1 116.88(13) . . ?
C1 N1 C2 122.78(16) . . ?
C1 N1 H3 119.9(19) . . ?
C2 N1 H3 117.3(19) . . ?
N1 C2 C3 108.98(15) . . ?
N1 C2 H2A 109.5(14) . . ?
C3 C2 H2A 112.5(14) . . ?
N1 C2 H2B 108.6(15) . . ?
C3 C2 H2B 111.1(16) . . ?
H2A C2 H2B 106.0(19) . . ?
C7 C3 C4 107.46(16) . . ?
C7 C3 C2 125.78(18) . . ?
C4 C3 C2 126.71(18) . . ?
C7 C3 Fe1 69.87(11) . . ?
C4 C3 Fe1 69.58(11) . . ?
C2 C3 Fe1 127.81(13) . . ?
C5 C4 C3 108.20(17) . . ?
C5 C4 Fe1 69.58(11) . . ?
C3 C4 Fe1 69.37(10) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Fe1 C4 H4 126.7 . . ?
C6 C5 C4 108.08(17) . . ?
C6 C5 Fe1 69.81(11) . . ?
C4 C5 Fe1 69.66(11) . . ?
C6 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.1 . . ?
C5 C6 C7 107.91(17) . . ?
C5 C6 Fe1 69.46(11) . . ?
C7 C6 Fe1 69.63(11) . . ?
C5 C6 H6 126.0 . . ?
C7 C6 H6 126.0 . . ?
Fe1 C6 H6 126.4 . . ?
C3 C7 C6 108.34(17) . . ?
C3 C7 Fe1 69.34(10) . . ?
C6 C7 Fe1 69.58(11) . . ?
C3 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
Fe1 C7 H7 126.8 . . ?
C12 C8 C9 108.43(19) . . ?
C12 C8 Fe1 69.90(11) . . ?
C9 C8 Fe1 69.74(11) . . ?
C12 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 126.2 . . ?
C10 C9 C8 107.9(2) . . ?
C10 C9 Fe1 69.68(12) . . ?
C8 C9 Fe1 69.67(11) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
Fe1 C9 H9 126.2 . . ?
C9 C10 C11 108.10(19) . . ?
C9 C10 Fe1 69.80(11) . . ?
C11 C10 Fe1 69.52(12) . . ?
C9 C10 H10 126.0 . . ?
C11 C10 H10 126.0 . . ?
Fe1 C10 H10 126.3 . . ?
C12 C11 C10 107.63(19) . . ?
C12 C11 Fe1 69.87(12) . . ?
C10 C11 Fe1 69.51(12) . . ?
C12 C11 H11 126.2 . . ?
C10 C11 H11 126.2 . . ?
Fe1 C11 H11 126.0 . . ?
C8 C12 C11 108.0(2) . . ?
C8 C12 Fe1 69.58(11) . . ?
C11 C12 Fe1 69.50(12) . . ?
C8 C12 H12 126.0 . . ?
C11 C12 H12 126.0 . . ?
Fe1 C12 H12 126.5 . . ?
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 C3 2.0400(18) . ?
Fe1 C5 2.0418(19) . ?
Fe1 C4 2.0429(19) . ?
Fe1 C10 2.043(2) . ?
Fe1 C11 2.043(2) . ?
Fe1 C8 2.0441(19) . ?
Fe1 C9 2.0450(19) . ?
Fe1 C6 2.0464(19) . ?
Fe1 C7 2.0472(18) . ?
Fe1 C12 2.048(2) . ?
P1 C1 1.8671(19) . ?
P1 H1 1.29(3) . ?
P1 H2 1.36(3) . ?
C1 O1 1.228(2) . ?
C1 N1 1.333(2) . ?
N1 C2 1.473(2) . ?
N1 H3 0.81(3) . ?
C2 C3 1.494(3) . ?
C2 H2A 0.99(2) . ?
C2 H2B 0.99(3) . ?
C3 C7 1.424(3) . ?
C3 C4 1.432(3) . ?
C4 C5 1.423(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.423(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.426(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C12 1.417(3) . ?
C8 C9 1.418(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.430(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.421(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
