#------------------------------------------------------------------------------
#$Date: 2016-04-05 20:18:43 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181713 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/55/7035586.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_7035586
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         'C27 H39 N2 P'
_chemical_formula_sum            'C27 H39 N2 P'
_chemical_formula_weight         422.57
_chemical_name_systematic
1,3-bis(2,6-diisopropylphenyl)-2-phosphanylideneimidazolidine
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-03-24
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8631(6)
_cell_length_b                   20.2676(9)
_cell_length_c                   10.9214(5)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.54
_cell_volume                     2625.9(2)
_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      173.0
_diffrn_measured_fraction_theta_full 1.000
_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     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42885
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.938
_diffrn_reflns_theta_min         2.010
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction''
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.069
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0682P)²+1.0435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             3242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01741f2.cif
_cod_data_source_block           DippNHCstar=PH
_cod_depositor_comments
'Adding full bibliography for 7035586--7035589.cif.'
_cod_database_code               7035586
_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   0.988
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C)
;
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
P1 P 0.74464(4) 0.2500 0.14191(6) 0.04110(19) Uani 1 2 d S T P
C1 C 0.88749(15) 0.2500 0.10472(16) 0.0244(4) Uani 1 2 d S T P
C2 C 1.06901(12) 0.28727(7) 0.05493(17) 0.0351(3) Uani 1 1 d . . .
C3 C 0.91400(11) 0.37089(6) 0.08231(13) 0.0292(3) Uani 1 1 d . . .
C4 C 0.86739(12) 0.39437(7) -0.02723(13) 0.0329(3) Uani 1 1 d . . .
C9 C 0.85172(14) 0.35023(8) -0.13787(14) 0.0400(4) Uani 1 1 d . . .
C5 C 0.83584(13) 0.46070(8) -0.03193(16) 0.0406(4) Uani 1 1 d . . .
C8 C 0.92722(12) 0.41091(7) 0.18511(14) 0.0338(3) Uani 1 1 d . . .
C6 C 0.84935(14) 0.50131(8) 0.06824(17) 0.0440(4) Uani 1 1 d . . .
C7 C 0.89341(14) 0.47681(8) 0.17565(16) 0.0415(4) Uani 1 1 d . . .
C12 C 0.97488(15) 0.38489(8) 0.30442(14) 0.0428(4) Uani 1 1 d . . .
C10 C 0.73105(19) 0.34824(12) -0.1804(2) 0.0740(7) Uani 1 1 d . . .
H10A H 0.6827 0.3333 -0.1132 0.111 Uiso 1 1 calc GR . .
H10B H 0.7242 0.3177 -0.2496 0.111 Uiso 1 1 calc GR . .
H10C H 0.7077 0.3925 -0.2063 0.111 Uiso 1 1 calc GR . .
C14 C 1.0742(2) 0.42486(12) 0.3488(2) 0.0803(8) Uani 1 1 d . . .
H14A H 1.0492 0.4696 0.3691 0.120 Uiso 1 1 calc GR . .
H14B H 1.1315 0.4269 0.2844 0.120 Uiso 1 1 calc GR . .
H14C H 1.1062 0.4040 0.4219 0.120 Uiso 1 1 calc GR . .
C11 C 0.9316(2) 0.36934(13) -0.2401(2) 0.0800(7) Uani 1 1 d . . .
H11A H 0.9303 0.3353 -0.3038 0.120 Uiso 1 1 calc GR . .
H11B H 1.0082 0.3735 -0.2074 0.120 Uiso 1 1 calc GR . .
H11C H 0.9079 0.4116 -0.2753 0.120 Uiso 1 1 calc GR . .
C13 C 0.8831(2) 0.38098(17) 0.4007(2) 0.0981(10) Uani 1 1 d . . .
H13A H 0.9135 0.3607 0.4752 0.147 Uiso 1 1 calc GR . .
H13B H 0.8205 0.3542 0.3698 0.147 Uiso 1 1 calc GR . .
H13C H 0.8559 0.4255 0.4195 0.147 Uiso 1 1 calc GR . .
N1 N 0.95327(9) 0.30394(5) 0.08720(11) 0.0298(3) Uani 1 1 d . . .
H5 H 0.8038(15) 0.4773(8) -0.1057(15) 0.040(4) Uiso 1 1 d . . .
H6 H 0.8251(16) 0.5472(10) 0.0623(17) 0.054(5) Uiso 1 1 d . . .
H7 H 0.9014(16) 0.5062(10) 0.2458(18) 0.055(5) Uiso 1 1 d . . .
H9 H 0.8719(15) 0.3061(9) -0.1152(15) 0.043(5) Uiso 1 1 d . . .
H12 H 1.0015(16) 0.3401(10) 0.2888(17) 0.056(5) Uiso 1 1 d . . .
H2A H 1.1201(18) 0.3048(9) 0.1133(17) 0.053(5) Uiso 1 1 d . . .
H2B H 1.0876(18) 0.3040(10) -0.026(2) 0.063(6) Uiso 1 1 d . . .
H1 H 0.721(3) 0.3076(18) 0.151(3) 0.045(9) Uiso 0.5 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'
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
N1 C1 P1 126.31(8) 7_565 .
N1 C1 P1 126.31(8) . .
N1 C1 N1 107.38(15) 7_565 .
N1 C2 C2 103.40(7) . 7_565
C4 C3 N1 118.74(12) . .
C8 C3 C4 122.30(13) . .
C8 C3 N1 118.91(12) . .
C3 C4 C9 121.92(13) . .
C5 C4 C3 117.66(14) . .
C5 C4 C9 120.42(14) . .
C10 C9 C4 112.26(15) . .
C10 C9 C11 111.95(18) . .
C11 C9 C4 111.12(15) . .
C6 C5 C4 120.97(15) . .
C3 C8 C7 117.64(14) . .
C3 C8 C12 122.15(13) . .
C7 C8 C12 120.20(14) . .
C7 C6 C5 120.33(14) . .
C6 C7 C8 121.09(15) . .
C8 C12 C13 110.30(16) . .
C14 C12 C8 112.38(15) . .
C14 C12 C13 111.44(19) . .
C1 N1 C2 112.90(11) . .
C1 N1 C3 125.47(11) . .
C3 N1 C2 121.06(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.7426(19) .
C1 N1 1.3567(15) 7_565
C1 N1 1.3568(15) .
C2 C2 1.511(3) 7_565
C2 N1 1.4572(18) .
C3 C4 1.401(2) .
C3 C8 1.394(2) .
C3 N1 1.4355(17) .
C4 C9 1.515(2) .
C4 C5 1.396(2) .
C9 C10 1.506(3) .
C9 C11 1.515(3) .
C5 C6 1.378(2) .
C8 C7 1.398(2) .
C8 C12 1.515(2) .
C6 C7 1.377(2) .
C12 C14 1.510(3) .
C12 C13 1.516(3) .
