#------------------------------------------------------------------------------
#$Date: 2016-04-05 20:18:43 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181713 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/55/7035588.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_7035588
loop_
_publ_author_name
'Bispinghoff, Mark'
'Tondreau, Aaron M.'
'Grützmacher, Hansjörg'
'Faradji, Charly A.'
'Pringle, Paul G.'
_publ_section_title
;
 Carbene insertion into a P-H bond: parent phosphinidene-carbene adducts
 from PH3 and bis(phosphinidene)mercury complexes.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5999
_journal_page_last               6003
_journal_paper_doi               10.1039/c5dt01741f
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C54 H72 Hg N4 P2'
_chemical_formula_sum            'C54 H68 Hg N4 P2'
_chemical_formula_weight         1035.65
_chemical_name_systematic
bis((1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)phosphanyl)mercury
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                103.202(2)
_cell_angle_beta                 112.596(2)
_cell_angle_gamma                95.847(2)
_cell_formula_units_Z            1
_cell_length_a                   10.4911(8)
_cell_length_b                   11.1172(8)
_cell_length_c                   12.5446(9)
_cell_measurement_reflns_used    9672
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.84
_cell_volume                     1285.49(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.1
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         2.241
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0215
_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)+(0.0292P)²+0.3845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6902
_reflns_number_total             6911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01741f2.cif
_cod_data_source_block           Hg(DippNHC=P)2
_cod_depositor_comments
'Adding full bibliography for 7035586--7035589.cif.'
_cod_original_cell_volume        1285.49(16)
_cod_database_code               7035588
_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_max   0.913
_shelx_estimated_absorpt_t_min   0.457
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C13(H13), C10(H10), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C2(H2), C3(H3), C18(H18), C8(H8), C6(H6), C7(H7), C19(H19)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C11(H11A,H11B,H11C), C15(H15A,
 H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C4 C 0.11081(18) 0.78382(16) 0.54393(15) 0.0134(3) Uani 1 1 d . . .
C21 C 0.5358(2) 0.72166(18) 0.95180(17) 0.0190(4) Uani 1 1 d . . .
C5 C 0.1748(2) 0.74389(17) 0.46602(17) 0.0168(3) Uani 1 1 d . . .
C20 C 0.6067(2) 0.6672(2) 1.04113(19) 0.0260(4) Uani 1 1 d . . .
H20 H 0.6931 0.6440 1.0464 0.031 Uiso 1 1 calc R . .
C2 C 0.26101(19) 0.93506(17) 0.74430(17) 0.0168(3) Uani 1 1 d . . .
H2 H 0.2506 1.0101 0.7207 0.020 Uiso 1 1 calc R . .
C3 C 0.3431(2) 0.92775(17) 0.85377(17) 0.0177(4) Uani 1 1 d . . .
H3 H 0.4018 0.9969 0.9222 0.021 Uiso 1 1 calc R . .
C22 C 0.5979(2) 0.7450(2) 0.8650(2) 0.0239(4) Uani 1 1 d . . .
H22 H 0.5401 0.7956 0.8163 0.029 Uiso 1 1 calc R . .
C14 C -0.2003(3) 0.9294(2) 0.5487(3) 0.0397(6) Uani 1 1 d . . .
H14A H -0.1583 0.9973 0.5268 0.060 Uiso 1 1 calc GR . .
H14B H -0.2268 0.9662 0.6140 0.060 Uiso 1 1 calc GR . .
H14C H -0.2846 0.8770 0.4783 0.060 Uiso 1 1 calc GR . .
C17 C 0.3505(2) 0.73065(19) 1.02553(17) 0.0213(4) Uani 1 1 d . . .
C23 C 0.7508(2) 0.8211(2) 0.9336(2) 0.0361(5) Uani 1 1 d . . .
H23A H 0.7536 0.9010 0.9883 0.054 Uiso 1 1 calc GR . .
H23B H 0.7864 0.8387 0.8759 0.054 Uiso 1 1 calc GR . .
H23C H 0.8099 0.7722 0.9805 0.054 Uiso 1 1 calc GR . .
C12 C 0.3512(3) 0.6200(2) 0.4289(2) 0.0352(5) Uani 1 1 d . . .
H12A H 0.2811 0.5429 0.4068 0.053 Uiso 1 1 calc GR . .
H12B H 0.4462 0.6052 0.4690 0.053 Uiso 1 1 calc GR . .
H12C H 0.3422 0.6434 0.3560 0.053 Uiso 1 1 calc GR . .
C24 C 0.5913(3) 0.6208(2) 0.7783(2) 0.0321(5) Uani 1 1 d . . .
H24A H 0.6498 0.5708 0.8240 0.048 Uiso 1 1 calc GR . .
H24B H 0.6266 0.6387 0.7205 0.048 Uiso 1 1 calc GR . .
H24C H 0.4933 0.5733 0.7347 0.048 Uiso 1 1 calc GR . .
C18 C 0.4287(2) 0.6791(2) 1.11518(18) 0.0271(4) Uani 1 1 d . . .
H18 H 0.3946 0.6664 1.1727 0.033 Uiso 1 1 calc R . .
C26 C 0.2307(3) 0.8630(3) 1.1317(3) 0.0451(7) Uani 1 1 d . . .
H26A H 0.2671 0.8306 1.2016 0.068 Uiso 1 1 calc GR . .
H26B H 0.1399 0.8855 1.1226 0.068 Uiso 1 1 calc GR . .
H26C H 0.2981 0.9381 1.1437 0.068 Uiso 1 1 calc GR . .
C8 C -0.1017(2) 0.7836(2) 0.37957(18) 0.0240(4) Uani 1 1 d . . .
H8 H -0.1956 0.7966 0.3487 0.029 Uiso 1 1 calc R . .
C1 C 0.23183(18) 0.72596(17) 0.73582(15) 0.0135(3) Uani 1 1 d . . .
C27 C 0.1059(3) 0.6420(3) 0.9961(3) 0.0431(6) Uani 1 1 d . . .
H27A H 0.0944 0.5785 0.9227 0.065 Uiso 1 1 calc GR . .
H27B H 0.0144 0.6629 0.9867 0.065 Uiso 1 1 calc GR . .
H27C H 0.1422 0.6082 1.0652 0.065 Uiso 1 1 calc GR . .
C9 C -0.0274(2) 0.80457(18) 0.50347(17) 0.0181(4) Uani 1 1 d . . .
C6 C 0.0948(2) 0.7238(2) 0.34340(18) 0.0239(4) Uani 1 1 d . . .
H6 H 0.1343 0.6957 0.2879 0.029 Uiso 1 1 calc R . .
C13 C -0.0930(2) 0.8477(2) 0.5910(2) 0.0278(5) Uani 1 1 d . . .
H13 H -0.0144 0.9021 0.6681 0.033 Uiso 1 1 calc R . .
C7 C -0.0413(2) 0.7443(2) 0.30109(19) 0.0283(5) Uani 1 1 d . . .
H7 H -0.0938 0.7311 0.2171 0.034 Uiso 1 1 calc R . .
C16 C 0.40620(19) 0.75077(17) 0.94464(16) 0.0161(3) Uani 1 1 d . . .
C11 C 0.4290(2) 0.8500(2) 0.5447(3) 0.0384(6) Uani 1 1 d . . .
H11A H 0.4120 0.8744 0.4709 0.058 Uiso 1 1 calc GR . .
H11B H 0.5261 0.8380 0.5799 0.058 Uiso 1 1 calc GR . .
H11C H 0.4147 0.9166 0.6027 0.058 Uiso 1 1 calc GR . .
C10 C 0.3263(2) 0.7269(2) 0.51438(19) 0.0220(4) Uani 1 1 d . . .
H10 H 0.3468 0.7045 0.5912 0.026 Uiso 1 1 calc R . .
C15 C -0.1555(4) 0.7405(3) 0.6200(3) 0.0485(7) Uani 1 1 d . . .
H15A H -0.1888 0.7732 0.6818 0.073 Uiso 1 1 calc GR . .
H15B H -0.0838 0.6918 0.6504 0.073 Uiso 1 1 calc GR . .
H15C H -0.2351 0.6857 0.5471 0.073 Uiso 1 1 calc GR . .
C19 C 0.5543(2) 0.6462(2) 1.12227(19) 0.0288(5) Uani 1 1 d . . .
H19 H 0.6046 0.6092 1.1828 0.035 Uiso 1 1 calc R . .
C25 C 0.2102(2) 0.7611(2) 1.0176(2) 0.0295(5) Uani 1 1 d . . .
H25 H 0.1699 0.7951 0.9472 0.035 Uiso 1 1 calc R . .
Hg1 Hg 0.0000 0.5000 0.5000 0.01370(4) Uani 1 2 d S T P
N1 N 0.19362(15) 0.81198(14) 0.67121(13) 0.0130(3) Uani 1 1 d . . .
N2 N 0.32715(16) 0.80076(14) 0.84939(13) 0.0141(3) Uani 1 1 d . . .
P1 P 0.18409(5) 0.56112(4) 0.70096(4) 0.01810(10) Uani 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'
N N 0.0061 0.0033 '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'
Hg Hg -2.3894 9.2266 '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
C5 C4 N1 118.27(16) .
C9 C4 C5 123.07(16) .
C9 C4 N1 118.56(16) .
C20 C21 C22 119.95(18) .
C20 C21 C16 117.48(18) .
C16 C21 C22 122.56(17) .
C4 C5 C10 121.18(16) .
C6 C5 C4 117.21(18) .
C6 C5 C10 121.59(17) .
C19 C20 C21 121.5(2) .
C3 C2 N1 107.27(16) .
C2 C3 N2 107.70(16) .
C21 C22 C23 111.16(18) .
C21 C22 C24 111.17(18) .
C24 C22 C23 110.17(18) .
C18 C17 C16 117.40(19) .
C18 C17 C25 120.07(19) .
C16 C17 C25 122.53(18) .
C19 C18 C17 121.5(2) .
C7 C8 C9 121.15(19) .
N1 C1 N2 103.59(14) .
N1 C1 P1 134.12(13) .
N2 C1 P1 122.29(13) .
C4 C9 C13 121.43(17) .
C8 C9 C4 116.94(18) .
C8 C9 C13 121.63(18) .
C7 C6 C5 120.95(19) .
C9 C13 C14 113.07(19) .
C15 C13 C14 110.8(2) .
C15 C13 C9 112.4(2) .
C8 C7 C6 120.68(19) .
C21 C16 N2 118.65(16) .
C17 C16 C21 122.34(17) .
C17 C16 N2 119.01(17) .
C5 C10 C12 112.83(18) .
C5 C10 C11 110.94(17) .
C11 C10 C12 110.53(19) .
C18 C19 C20 119.74(19) .
C17 C25 C26 110.7(2) .
C17 C25 C27 110.84(19) .
C27 C25 C26 111.0(2) .
P1 Hg1 P1 180.00(3) 2_566
C2 N1 C4 121.99(15) .
C1 N1 C4 126.86(15) .
C1 N1 C2 110.75(15) .
C3 N2 C16 125.62(15) .
C1 N2 C3 110.67(15) .
C1 N2 C16 123.50(15) .
C1 P1 Hg1 103.56(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C5 1.403(3) .
C4 C9 1.403(3) .
C4 N1 1.433(2) .
C21 C20 1.392(3) .
C21 C22 1.522(3) .
C21 C16 1.403(3) .
C5 C6 1.390(3) .
C5 C10 1.518(3) .
C20 C19 1.380(3) .
C2 C3 1.338(3) .
C2 N1 1.394(2) .
C3 N2 1.391(2) .
C22 C23 1.536(3) .
C22 C24 1.527(3) .
C14 C13 1.531(3) .
C17 C18 1.395(3) .
C17 C16 1.398(3) .
C17 C25 1.516(3) .
C12 C10 1.525(3) .
C18 C19 1.379(3) .
C26 C25 1.533(3) .
C8 C9 1.394(3) .
C8 C7 1.379(3) .
C1 N1 1.384(2) .
C1 N2 1.384(2) .
C1 P1 1.7547(19) .
C27 C25 1.529(4) .
C9 C13 1.522(3) .
C6 C7 1.383(3) .
C13 C15 1.486(4) .
C16 N2 1.435(2) .
C11 C10 1.524(3) .
Hg1 P1 2.3991(5) 2_566
Hg1 P1 2.3991(5) .
