#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/24/1512448.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_1512448
loop_
_publ_author_name
'Srinivasa Budagumpi'
'Rosenani A. Haque'
'Abbas Washeel Salman'
'Mohammed Z. Ghdhayeb'
_publ_section_title
;
 Mercury(II)- and silver(I)-N-heterocyclic carbene complexes of CNC
 pincer-type ligands: Synthesis, crystal structures and Hofmann-type
 elimination studies
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              61
_journal_page_last               72
_journal_paper_doi               10.1016/j.ica.2012.06.044
_journal_volume                  392
_journal_year                    2012
_chemical_formula_sum            'C15 H19 F12 N5 P2'
_chemical_formula_weight         559.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4018(2)
_cell_length_b                   18.2059(4)
_cell_length_c                   25.6928(6)
_cell_measurement_temperature    100(2)
_cell_volume                     4397.79(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32730
_diffrn_reflns_theta_full        30.14
_diffrn_reflns_theta_max         30.14
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.9194
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+2.9393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                4744
_reflns_number_total             6448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2012-392-61-72-1.cif
_cod_data_source_block           pyimme_0m
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1512448
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.35983(5) 0.09646(2) 0.390683(17) 0.01937(10) Uani 1 1 d .
P2 P 0.17023(5) 0.12631(2) 0.675547(18) 0.02305(11) Uani 1 1 d .
F1 F 0.45241(13) 0.07978(7) 0.34009(4) 0.0395(3) Uani 1 1 d .
F2 F 0.26748(13) 0.11389(7) 0.44143(4) 0.0403(3) Uani 1 1 d .
F3 F 0.47163(13) 0.05238(6) 0.42520(5) 0.0360(3) Uani 1 1 d .
F4 F 0.25033(12) 0.14256(6) 0.35608(4) 0.0328(3) Uani 1 1 d .
F5 F 0.44929(13) 0.17029(6) 0.40098(5) 0.0380(3) Uani 1 1 d .
F6 F 0.26950(12) 0.02364(6) 0.38049(4) 0.0319(3) Uani 1 1 d .
F7 F 0.32679(14) 0.14229(7) 0.69690(6) 0.0485(4) Uani 1 1 d .
F8 F 0.23137(13) 0.05768(6) 0.64294(5) 0.0383(3) Uani 1 1 d .
F9 F 0.10982(15) 0.19433(6) 0.70766(5) 0.0422(3) Uani 1 1 d .
F10 F 0.01454(12) 0.10830(6) 0.65370(4) 0.0324(3) Uani 1 1 d .
F11 F 0.19952(14) 0.17936(6) 0.62716(5) 0.0385(3) Uani 1 1 d .
F12 F 0.14005(13) 0.07261(6) 0.72367(4) 0.0300(3) Uani 1 1 d .
N1 N 0.04199(15) 0.08785(7) 0.28314(5) 0.0176(3) Uani 1 1 d .
N2 N -0.11453(15) 0.12905(7) 0.33733(5) 0.0177(3) Uani 1 1 d .
N3 N -0.06168(15) 0.17995(7) 0.44445(5) 0.0178(3) Uani 1 1 d .
N4 N 0.10613(16) 0.29465(7) 0.46313(5) 0.0204(3) Uani 1 1 d .
N5 N 0.12737(17) 0.34106(8) 0.38636(6) 0.0236(3) Uani 1 1 d .
C1 C 0.14642(19) 0.03903(9) 0.25880(6) 0.0224(3) Uani 1 1 d .
H1A H 0.1474 -0.0082 0.2772 0.034 Uiso 1 1 calc R
H1B H 0.2410 0.0615 0.2607 0.034 Uiso 1 1 calc R
H1C H 0.1207 0.0311 0.2223 0.034 Uiso 1 1 calc R
C2 C 0.0094(2) 0.15862(9) 0.26815(7) 0.0243(4) Uani 1 1 d .
H2A H 0.0485 0.1844 0.2394 0.029 Uiso 1 1 calc R
C3 C -0.0879(2) 0.18423(9) 0.30193(7) 0.0248(4) Uani 1 1 d .
H3A H -0.1305 0.2316 0.3015 0.030 Uiso 1 1 calc R
C4 C -0.03313(17) 0.07167(9) 0.32527(6) 0.0165(3) Uani 1 1 d .
H4A H -0.0295 0.0266 0.3438 0.020 Uiso 1 1 calc R
C5 C -0.22069(18) 0.13078(10) 0.37940(7) 0.0228(4) Uani 1 1 d .
H5A H -0.2878 0.0894 0.3748 0.027 Uiso 1 1 calc R
H5B H -0.2757 0.1770 0.3771 0.027 Uiso 1 1 calc R
C6 C -0.15289(18) 0.12556(9) 0.43251(6) 0.0196(3) Uani 1 1 d .
C7 C -0.1864(2) 0.06922(10) 0.46642(8) 0.0268(4) Uani 1 1 d .
H7A H -0.2509 0.0316 0.4565 0.032 Uiso 1 1 calc R
C8 C -0.1237(2) 0.06899(11) 0.51528(8) 0.0312(4) Uani 1 1 d .
H8A H -0.1455 0.0314 0.5396 0.037 Uiso 1 1 calc R
C9 C -0.0294(2) 0.12395(10) 0.52809(7) 0.0268(4) Uani 1 1 d .
H9A H 0.0153 0.1249 0.5612 0.032 Uiso 1 1 calc R
C10 C -0.00112(18) 0.17815(9) 0.49123(6) 0.0195(3) Uani 1 1 d .
C11 C 0.1054(2) 0.23846(9) 0.50353(7) 0.0238(4) Uani 1 1 d .
H11A H 0.0809 0.2612 0.5373 0.029 Uiso 1 1 calc R
H11B H 0.2017 0.2168 0.5066 0.029 Uiso 1 1 calc R
C12 C 0.17079(19) 0.28769(9) 0.41744(7) 0.0228(4) Uani 1 1 d .
H12A H 0.2373 0.2505 0.4085 0.027 Uiso 1 1 calc R
C13 C 0.01550(19) 0.35401(9) 0.46068(7) 0.0243(4) Uani 1 1 d .
H13A H -0.0452 0.3711 0.4876 0.029 Uiso 1 1 calc R
C14 C 0.0295(2) 0.38309(10) 0.41275(8) 0.0272(4) Uani 1 1 d .
H14A H -0.0192 0.4249 0.3996 0.033 Uiso 1 1 calc R
C15 C 0.1744(2) 0.35251(12) 0.33252(7) 0.0354(5) Uani 1 1 d .
H15A H 0.2452 0.3152 0.3233 0.053 Uiso 1 1 calc R
H15B H 0.2167 0.4015 0.3292 0.053 Uiso 1 1 calc R
H15C H 0.0926 0.3485 0.3090 0.053 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
F3 P1 F1 89.87(7)
F3 P1 F6 91.37(6)
F1 P1 F6 89.92(7)
F3 P1 F2 90.24(7)
F1 P1 F2 179.52(8)
F6 P1 F2 90.55(7)
F3 P1 F4 178.48(7)
F1 P1 F4 89.90(7)
F6 P1 F4 90.13(6)
F2 P1 F4 89.98(7)
F3 P1 F5 89.10(6)
F1 P1 F5 90.45(7)
F6 P1 F5 179.40(7)
F2 P1 F5 89.08(7)
F4 P1 F5 89.40(6)
F9 P2 F7 90.51(8)
F9 P2 F11 89.69(7)
F7 P2 F11 89.91(7)
F9 P2 F12 90.66(6)
F7 P2 F12 90.53(7)
F11 P2 F12 179.44(7)
F9 P2 F10 90.85(7)
F7 P2 F10 178.58(7)
F11 P2 F10 90.49(7)
F12 P2 F10 89.07(6)
F9 P2 F8 179.84(8)
F7 P2 F8 89.49(7)
F11 P2 F8 90.16(7)
F12 P2 F8 89.50(6)
F10 P2 F8 89.15(7)
C4 N1 C2 108.51(14)
C4 N1 C1 124.81(14)
C2 N1 C1 126.62(14)
C4 N2 C3 108.31(14)
C4 N2 C5 125.27(14)
C3 N2 C5 126.32(14)
C10 N3 C6 117.44(15)
C12 N4 C13 108.51(15)
C12 N4 C11 124.39(15)
C13 N4 C11 125.48(15)
C12 N5 C14 108.51(15)
C12 N5 C15 125.52(17)
C14 N5 C15 125.97(16)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 N1 107.14(15)
C3 C2 H2A 126.4
N1 C2 H2A 126.4
C2 C3 N2 107.26(15)
C2 C3 H3A 126.4
N2 C3 H3A 126.4
N1 C4 N2 108.77(14)
N1 C4 H4A 125.6
N2 C4 H4A 125.6
N2 C5 C6 112.11(14)
N2 C5 H5A 109.2
C6 C5 H5A 109.2
N2 C5 H5B 109.2
C6 C5 H5B 109.2
H5A C5 H5B 107.9
N3 C6 C7 123.22(16)
N3 C6 C5 115.41(15)
C7 C6 C5 121.35(16)
C6 C7 C8 118.39(17)
C6 C7 H7A 120.8
C8 C7 H7A 120.8
C9 C8 C7 119.22(17)
C9 C8 H8A 120.4
C7 C8 H8A 120.4
C8 C9 C10 118.37(17)
C8 C9 H9A 120.8
C10 C9 H9A 120.8
N3 C10 C9 123.36(16)
N3 C10 C11 116.89(15)
C9 C10 C11 119.74(15)
N4 C11 C10 111.23(14)
N4 C11 H11A 109.4
C10 C11 H11A 109.4
N4 C11 H11B 109.4
C10 C11 H11B 109.4
H11A C11 H11B 108.0
N5 C12 N4 108.82(16)
N5 C12 H12A 125.6
N4 C12 H12A 125.6
C14 C13 N4 106.84(16)
C14 C13 H13A 126.6
N4 C13 H13A 126.6
C13 C14 N5 107.30(16)
C13 C14 H14A 126.4
N5 C14 H14A 126.4
N5 C15 H15A 109.5
N5 C15 H15B 109.5
H15A C15 H15B 109.5
N5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 F3 1.5924(12)
P1 F1 1.5935(12)
P1 F6 1.5962(11)
P1 F2 1.5983(11)
P1 F4 1.5983(11)
P1 F5 1.6074(12)
P2 F9 1.5928(12)
P2 F7 1.5976(13)
P2 F11 1.5981(12)
P2 F12 1.6015(11)
P2 F10 1.6017(12)
P2 F8 1.6105(12)
N1 C4 1.326(2)
N1 C2 1.379(2)
N1 C1 1.465(2)
N2 C4 1.332(2)
N2 C3 1.378(2)
N2 C5 1.472(2)
N3 C10 1.330(2)
N3 C6 1.345(2)
N4 C12 1.328(2)
N4 C13 1.378(2)
N4 C11 1.457(2)
N5 C12 1.322(2)
N5 C14 1.376(2)
N5 C15 1.467(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.345(3)
C2 H2A 0.9500
C3 H3A 0.9500
C4 H4A 0.9500
C5 C6 1.509(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.382(2)
C7 C8 1.387(3)
C7 H7A 0.9500
C8 C9 1.376(3)
C8 H8A 0.9500
C9 C10 1.393(2)
C9 H9A 0.9500
C10 C11 1.520(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9500
C13 C14 1.347(3)
C13 H13A 0.9500
C14 H14A 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
C4 N1 C2 C3 -0.6(2)
C1 N1 C2 C3 -177.89(16)
N1 C2 C3 N2 -0.1(2)
C4 N2 C3 C2 0.7(2)
C5 N2 C3 C2 -175.79(15)
C2 N1 C4 N2 1.06(18)
C1 N1 C4 N2 178.41(14)
C3 N2 C4 N1 -1.10(18)
C5 N2 C4 N1 175.45(14)
C4 N2 C5 C6 66.7(2)
C3 N2 C5 C6 -117.36(18)
C10 N3 C6 C7 0.5(2)
C10 N3 C6 C5 178.98(14)
N2 C5 C6 N3 60.62(19)
N2 C5 C6 C7 -120.88(17)
N3 C6 C7 C8 0.4(3)
C5 C6 C7 C8 -177.96(16)
C6 C7 C8 C9 -0.8(3)
C7 C8 C9 C10 0.3(3)
C6 N3 C10 C9 -1.1(2)
C6 N3 C10 C11 177.99(14)
C8 C9 C10 N3 0.7(3)
C8 C9 C10 C11 -178.34(16)
C12 N4 C11 C10 -78.3(2)
C13 N4 C11 C10 85.42(19)
N3 C10 C11 N4 8.4(2)
C9 C10 C11 N4 -172.54(15)
C14 N5 C12 N4 -1.0(2)
C15 N5 C12 N4 179.88(16)
C13 N4 C12 N5 1.31(19)
C11 N4 C12 N5 167.41(15)
C12 N4 C13 C14 -1.1(2)
C11 N4 C13 C14 -166.99(16)
N4 C13 C14 N5 0.4(2)
C12 N5 C14 C13 0.4(2)
C15 N5 C14 C13 179.44(17)
