#------------------------------------------------------------------------------
#$Date: 2019-11-25 02:47:51 +0200 (Mon, 25 Nov 2019) $
#$Revision: 239982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/35/06/4350671.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_4350671
loop_
_publ_author_name
'Rieb, Julia'
'Raba, Andreas'
'Haslinger, Stefan'
'Kaspar, Manuel'
'Pöthig, Alexander'
'Cokoja, Mirza'
'Basset, Jean-Marie'
'Kühn, Fritz E'
_publ_section_title
;
 Synthesis, characterization, and reactivity of furan- and
 thiophene-functionalized bis(N-heterocyclic carbene) complexes of
 iron(II).
;
_journal_issue                   18
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9598
_journal_page_last               9606
_journal_paper_doi               10.1021/ic500959m
_journal_volume                  53
_journal_year                    2014
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C15 H14 N4 O2, 2(F6 P), C2 H3 N'
_chemical_formula_sum            'C17 H17 F12 N5 O2 P2'
_chemical_formula_weight         613.30
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.2220(9)
_cell_length_b                   14.0397(6)
_cell_length_c                   6.9906(3)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.3585
_cell_measurement_theta_min      2.2208
_cell_volume                     2377.29(17)
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'MONTEL optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            41103
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.47
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0314P)²+1.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                1935
_reflns_number_total             2292
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic500959m_si_002.cif
_cod_data_source_block           compound_1a
_cod_database_code               4350671
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,1/2-z
4 -x,1/2+y,-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,1/2+z
8 x,1/2-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.30630(4) 0.56332(8) 0.04902(16) 1.000 0.0239(3) d .
N1 N Uani 0.35278(5) 0.45015(9) 0.22784(17) 1.000 0.0152(4) d .
N2 N Uani 0.37634(5) 0.33548(9) 0.41447(17) 1.000 0.0155(4) d .
C1 C Uani 0.38478(6) 0.37388(11) 0.2430(2) 1.000 0.0156(4) d .
C2 C Uani 0.33731(6) 0.38904(11) 0.5107(2) 1.000 0.0193(5) d .
C3 C Uani 0.32264(6) 0.46087(11) 0.3948(2) 1.000 0.0183(4) d .
C4 C Uani 0.35311(6) 0.51259(11) 0.0710(2) 1.000 0.0168(4) d .
C5 C Uani 0.39071(7) 0.53172(13) -0.0632(2) 1.000 0.0268(5) d .
C6 C Uani 0.36500(7) 0.60111(13) -0.1837(2) 1.000 0.0279(5) d .
C7 C Uani 0.31525(7) 0.61777(12) -0.1112(2) 1.000 0.0277(5) d .
C8 C Uani 0.40421(9) 0.25000 0.4826(3) 1.000 0.0196(7) d S
P1 P Uani 0.26546(2) 0.25000 0.94830(7) 1.000 0.0153(2) d S
F1 F Uani 0.26641(4) 0.36374(7) 0.94859(13) 1.000 0.0280(3) d .
F2 F Uani 0.20187(5) 0.25000 1.00209(19) 1.000 0.0302(5) d S
F3 F Uani 0.28167(5) 0.25000 1.17161(16) 1.000 0.0219(4) d S
F4 F Uani 0.33060(5) 0.25000 0.89638(18) 1.000 0.0247(4) d S
F5 F Uani 0.25099(5) 0.25000 0.72578(17) 1.000 0.0248(4) d S
P2 P Uani 0.00000 0.00000 0.00000 1.000 0.0207(2) d S
F6 F Uani -0.02779(4) 0.08285(8) -0.12485(14) 1.000 0.0330(3) d .
F7 F Uani -0.00198(4) 0.06744(8) 0.18401(14) 1.000 0.0348(3) d .
F8 F Uani 0.05998(4) 0.03981(7) -0.05172(14) 1.000 0.0315(3) d .
N3 N Uani -0.02611(10) 0.25000 0.5065(3) 1.000 0.0402(8) d S
C9 C Uani 0.01399(11) 0.25000 0.5909(4) 1.000 0.0289(8) d S
C10 C Uani 0.06493(10) 0.25000 0.7006(4) 1.000 0.0332(8) d S
H1 H Uiso 0.40940 0.35070 0.14800 1.000 0.0190 c R
H2 H Uiso 0.32350 0.37720 0.63560 1.000 0.0230 c R
H3 H Uiso 0.29660 0.50960 0.42200 1.000 0.0220 c R
H5 H Uiso 0.42660 0.50520 -0.07580 1.000 0.0320 c R
H6 H Uiso 0.38050 0.62980 -0.29440 1.000 0.0340 c R
H7 H Uiso 0.28930 0.66150 -0.16320 1.000 0.0330 c R
H8A H Uiso 0.40480 0.25000 0.62420 1.000 0.0240 c SR
H8B H Uiso 0.44290 0.25000 0.43690 1.000 0.0240 c SR
H10A H Uiso 0.06190 0.29580 0.80590 0.500 0.0500 c RP
H10B H Uiso 0.09570 0.26810 0.61730 0.500 0.0500 c RP
H10C H Uiso 0.07150 0.18620 0.75250 0.500 0.0500 c RP
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'
F F 0.0171 0.0103 ' 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
F4 P1 F5 89.74(7) . . yes
F1 P1 F4 89.21(4) 8_555 . yes
F1 P1 F5 90.25(4) 8_555 . yes
F1 P1 F2 90.79(4) . . yes
F1 P1 F3 89.73(4) . . yes
F1 P1 F4 89.21(4) . . yes
F1 P1 F5 90.25(4) . . yes
F1 P1 F1 178.34(6) . 8_555 yes
F2 P1 F3 90.40(7) . . yes
F2 P1 F4 179.24(7) . . yes
F2 P1 F5 91.02(7) . . yes
F1 P1 F2 90.79(4) 8_555 . yes
F3 P1 F4 88.84(7) . . yes
F3 P1 F5 178.58(7) . . yes
F1 P1 F3 89.73(4) 8_555 . yes
F7 P2 F8 90.13(5) 5_555 5_555 yes
F6 P2 F8 90.27(5) 5_555 5_555 yes
F6 P2 F7 90.25(5) 5_555 . yes
F6 P2 F7 89.76(5) . . yes
F6 P2 F8 90.27(5) . . yes
F6 P2 F6 180.00 . 5_555 yes
F6 P2 F7 90.25(5) . 5_555 yes
F6 P2 F8 89.73(5) . 5_555 yes
F7 P2 F8 90.13(5) . . yes
F6 P2 F8 89.73(5) 5_555 . yes
F7 P2 F7 180.00 . 5_555 yes
F7 P2 F8 89.88(5) . 5_555 yes
F6 P2 F7 89.76(5) 5_555 5_555 yes
F7 P2 F8 89.88(5) 5_555 . yes
F8 P2 F8 180.00 . 5_555 yes
C4 O1 C7 104.74(12) . . yes
C1 N1 C4 124.29(12) . . yes
C1 N1 C3 109.18(12) . . yes
C3 N1 C4 126.40(13) . . yes
C1 N2 C8 123.86(14) . . yes
C1 N2 C2 108.85(12) . . yes
C2 N2 C8 127.28(13) . . yes
N1 C1 N2 108.03(12) . . yes
N2 C2 C3 107.22(12) . . yes
N1 C3 C2 106.72(13) . . yes
N1 C4 C5 132.72(14) . . yes
O1 C4 N1 114.47(12) . . yes
O1 C4 C5 112.80(14) . . yes
C4 C5 C6 104.71(14) . . no
C5 C6 C7 106.87(14) . . no
O1 C7 C6 110.88(14) . . yes
N2 C8 N2 110.91(16) . 8_555 yes
N1 C1 H1 126.00 . . no
N2 C1 H1 126.00 . . no
C3 C2 H2 126.00 . . no
N2 C2 H2 126.00 . . no
N1 C3 H3 127.00 . . no
C2 C3 H3 127.00 . . no
C6 C5 H5 128.00 . . no
C4 C5 H5 128.00 . . no
C5 C6 H6 127.00 . . no
C7 C6 H6 127.00 . . no
O1 C7 H7 125.00 . . no
C6 C7 H7 125.00 . . no
N2 C8 H8B 109.00 8_555 . no
N2 C8 H8A 109.00 . . no
N2 C8 H8B 109.00 . . no
H8A C8 H8B 108.00 . . no
N2 C8 H8A 109.00 8_555 . no
N3 C9 C10 179.4(3) . . yes
C9 C10 H10A 109.00 . . no
C9 C10 H10B 109.00 . . no
C9 C10 H10C 109.00 . . no
C9 C10 H10A 109.00 . 8_555 no
C9 C10 H10B 109.00 . 8_555 no
C9 C10 H10C 109.00 . 8_555 no
H10A C10 H10B 109.00 . . no
H10A C10 H10C 110.00 . . no
H10A C10 H10A 82.00 . 8_555 no
H10A C10 H10B 132.00 . 8_555 no
H10A C10 H10C 30.00 . 8_555 no
H10B C10 H10C 110.00 . . no
H10A C10 H10B 132.00 8_555 . no
H10B C10 H10B 30.00 . 8_555 no
H10B C10 H10C 82.00 . 8_555 no
H10A C10 H10C 30.00 8_555 . no
H10B C10 H10C 82.00 8_555 . no
H10C C10 H10C 132.00 . 8_555 no
H10A C10 H10B 109.00 8_555 8_555 no
H10A C10 H10C 110.00 8_555 8_555 no
H10B C10 H10C 110.00 8_555 8_555 no
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
P1 F3 1.6097(12) . yes
P1 F4 1.6190(13) . yes
P1 F5 1.5946(13) . yes
P1 F1 1.5970(10) 8_555 yes
P1 F1 1.5970(10) . yes
P1 F2 1.5855(13) . yes
P2 F6 1.6025(11) . yes
P2 F8 1.5981(10) 5_555 yes
P2 F7 1.5980(10) 5_555 yes
P2 F7 1.5980(10) . yes
P2 F8 1.5981(10) . yes
P2 F6 1.6025(11) 5_555 yes
O1 C4 1.3478(18) . yes
O1 C7 1.3733(19) . yes
N1 C3 1.3849(19) . yes
N1 C4 1.4038(19) . yes
N1 C1 1.326(2) . yes
N2 C1 1.3301(19) . yes
N2 C2 1.3827(19) . yes
N2 C8 1.4570(17) . yes
N3 C9 1.137(4) . yes
C2 C3 1.342(2) . no
C4 C5 1.335(2) . no
C5 C6 1.431(2) . no
C6 C7 1.328(2) . no
C1 H1 0.9500 . no
C2 H2 0.9500 . no
C3 H3 0.9500 . no
C5 H5 0.9500 . no
C6 H6 0.9500 . no
C7 H7 0.9500 . no
C8 H8B 0.9900 . no
C8 H8A 0.9900 . no
C9 C10 1.453(4) . no
C10 H10A 0.9800 . no
C10 H10B 0.9800 . no
C10 H10C 0.9800 . no
C10 H10A 0.9800 8_555 no
C10 H10B 0.9800 8_555 no
C10 H10C 0.9800 8_555 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N3 0.9500 2.3700 3.275(2) 160.00 3_555 yes
C3 H3 F1 0.9500 2.3500 3.2951(18) 173.00 2_564 yes
C7 H7 F3 0.9500 2.4200 3.3560(19) 170.00 2_563 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C4 N1 -179.29(12) . no
C7 O1 C4 C5 0.30(17) . no
C4 O1 C7 C6 0.07(18) . no
C3 N1 C1 N2 -0.24(17) . no
C4 N1 C1 N2 175.72(13) . no
C1 N1 C3 C2 -0.05(17) . no
C4 N1 C3 C2 -175.90(14) . no
C1 N1 C4 O1 157.38(14) . no
C1 N1 C4 C5 -22.1(3) . no
C3 N1 C4 O1 -27.4(2) . no
C3 N1 C4 C5 153.15(17) . no
C2 N2 C1 N1 0.42(17) . no
C8 N2 C1 N1 179.72(13) . no
C1 N2 C2 C3 -0.45(17) . no
C8 N2 C2 C3 -179.72(14) . no
C1 N2 C8 N2 -83.46(19) 8_555 no
C2 N2 C8 N2 95.71(18) 8_555 no
N2 C2 C3 N1 0.30(16) . no
O1 C4 C5 C6 -0.52(18) . no
N1 C4 C5 C6 178.98(16) . no
C4 C5 C6 C7 0.53(19) . no
C5 C6 C7 O1 -0.38(19) . no
