#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:12:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178553 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/61/4066174.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_4066174
loop_
_publ_author_name
'Wang, Yuzhong'
'Xie, Yaoming'
'Abraham, Mariham Y.'
'Gilliard, Robert J.'
'Wei, Pingrong'
'Schaefer, Henry F.'
'Schleyer, Paul v. R.'
'Robinson, Gregory H.'
_publ_section_title
;
 Carbene-Stabilized Parent Phosphinidene†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              4778
_journal_paper_doi               10.1021/om100335j
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C27 H36 Cl3 N2 P'
_chemical_formula_weight         525.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.2150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6288(6)
_cell_length_b                   13.9767(7)
_cell_length_c                   19.8632(11)
_cell_measurement_reflns_used    5289
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.728
_cell_measurement_theta_min      2.436
_cell_volume                     2872.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER APEX II'
_diffrn_measurement_method       OMEGA-SCAN
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39278
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         7141
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0686
_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)+(0.1156P)²+0.9836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2286
_reflns_number_gt                3986
_reflns_number_total             7141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100335j_si_002.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4066174
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.5412(8) 0.8561(7) 0.2037(4) 0.0619(19) Uani 0.339(2) 1 d PDU A 1
Cl1 Cl 0.6663(3) 0.7859(2) 0.27928(16) 0.0912(12) Uani 0.339(2) 1 d PDU A 1
Cl2 Cl 0.3583(10) 0.7640(7) 0.2310(6) 0.110(3) Uani 0.339(2) 1 d PDU A 1
Cl3 Cl 0.7295(7) 0.9281(7) 0.2051(6) 0.090(2) Uani 0.339(2) 1 d PDU A 1
P1A P 0.5635(4) 0.8486(3) 0.2217(2) 0.0515(7) Uani 0.661(2) 1 d PDU A 2
Cl1A Cl 0.48050(12) 0.84056(9) 0.11825(6) 0.0597(4) Uani 0.661(2) 1 d PDU A 2
Cl2A Cl 0.3776(5) 0.7586(3) 0.2417(2) 0.0720(8) Uani 0.661(2) 1 d PDU A 2
Cl3A Cl 0.7108(5) 0.9428(4) 0.1901(3) 0.116(2) Uani 0.661(2) 1 d PDU A 2
N1 N 0.3968(2) 1.02040(16) 0.21830(11) 0.0432(5) Uani 1 1 d . A .
N2 N 0.5140(2) 0.98344(17) 0.31883(11) 0.0450(5) Uani 1 1 d . A .
C1 C 0.4875(2) 0.95790(18) 0.25156(13) 0.0393(6) Uani 1 1 d D . .
C2 C 0.3657(3) 1.0843(2) 0.26492(16) 0.0570(8) Uani 1 1 d . . .
H2 H 0.3061 1.1340 0.2551 0.661(2) Uiso 1 1 calc R A .
C3 C 0.4391(3) 1.0606(2) 0.32781(17) 0.0604(8) Uani 1 1 d . A .
H3 H 0.4389 1.0909 0.3695 0.661(2) Uiso 1 1 calc R . .
C4 C 0.6111(3) 0.9438(2) 0.37616(14) 0.0505(7) Uani 1 1 d . . .
C5 C 0.7349(3) 0.9831(2) 0.39017(17) 0.0608(8) Uani 1 1 d . A .
C6 C 0.8245(4) 0.9468(3) 0.4464(2) 0.0907(13) Uani 1 1 d . . .
H6 H 0.9089 0.9698 0.4563 0.661(2) Uiso 1 1 calc R A .
C7 C 0.7897(6) 0.8771(4) 0.4879(2) 0.1124(19) Uani 1 1 d . A .
H7 H 0.8510 0.8538 0.5255 0.661(2) Uiso 1 1 calc R . .
C8 C 0.6656(6) 0.8414(3) 0.4746(2) 0.0998(16) Uani 1 1 d . . .
H8 H 0.6438 0.7947 0.5033 0.661(2) Uiso 1 1 calc R A .
C9 C 0.5715(4) 0.8754(2) 0.41780(16) 0.0713(10) Uani 1 1 d D A .
C10 C 0.4152(19) 0.867(2) 0.3891(19) 0.093(10) Uani 0.148(5) 1 d PDU A 1
H10 H 0.3861 0.8797 0.3395 0.661(2) Uiso 0.148(5) 1 calc PR A 1
C11 C 0.343(7) 0.926(3) 0.434(2) 0.116(14) Uani 0.148(5) 1 d PDU A 1
H11A H 0.2533 0.9079 0.4236 0.148(5) Uiso 0.148(5) 1 calc PR A 1
H11B H 0.3506 0.9926 0.4250 0.148(5) Uiso 0.148(5) 1 calc PR A 1
H11C H 0.3800 0.9132 0.4822 0.148(5) Uiso 0.148(5) 1 calc PR A 1
C12 C 0.386(4) 0.761(2) 0.410(2) 0.086(10) Uani 0.148(5) 1 d PDU A 1
H12A H 0.4270 0.7163 0.3852 0.148(5) Uiso 0.148(5) 1 calc PR A 1
H12B H 0.2940 0.7503 0.3982 0.148(5) Uiso 0.148(5) 1 calc PR A 1
H12C H 0.4181 0.7524 0.4586 0.148(5) Uiso 0.148(5) 1 calc PR A 1
C10' C 0.4340(6) 0.8386(5) 0.4073(3) 0.085(2) Uani 0.852(5) 1 d PDU A 2
H10' H 0.3862 0.8548 0.3604 0.661(2) Uiso 0.852(5) 1 calc PR A 2
C11' C 0.3698(10) 0.8860(8) 0.4586(5) 0.167(5) Uani 0.852(5) 1 d PDU A 2
H11D H 0.2864 0.8578 0.4556 0.148(5) Uiso 0.852(5) 1 calc PR A 2
H11E H 0.3600 0.9531 0.4484 0.148(5) Uiso 0.852(5) 1 calc PR A 2
H11F H 0.4221 0.8774 0.5044 0.148(5) Uiso 0.852(5) 1 calc PR A 2
C12' C 0.4354(11) 0.7272(5) 0.4161(4) 0.146(4) Uani 0.852(5) 1 d PDU A 2
H12D H 0.3482 0.7038 0.4069 0.148(5) Uiso 0.852(5) 1 calc PR A 2
H12E H 0.4789 0.7109 0.4625 0.148(5) Uiso 0.852(5) 1 calc PR A 2
H12F H 0.4798 0.6986 0.3841 0.148(5) Uiso 0.852(5) 1 calc PR A 2
C13 C 0.7709(4) 1.0665(3) 0.3482(2) 0.0745(10) Uani 1 1 d . . .
H13 H 0.7114 1.0671 0.3026 0.661(2) Uiso 1 1 calc R A .
C14 C 0.7564(5) 1.1613(3) 0.3853(3) 0.1061(16) Uani 1 1 d . A .
H14A H 0.6692 1.1675 0.3905 0.148(5) Uiso 1 1 calc R . .
H14B H 0.7766 1.2139 0.3585 0.148(5) Uiso 1 1 calc R . .
H14C H 0.8145 1.1616 0.4301 0.148(5) Uiso 1 1 calc R . .
C15 C 0.9108(4) 1.0548(5) 0.3386(3) 0.124(2) Uani 1 1 d . A .
H15A H 0.9170 0.9968 0.3137 0.148(5) Uiso 1 1 calc R . .
H15B H 0.9697 1.0521 0.3831 0.148(5) Uiso 1 1 calc R . .
H15C H 0.9323 1.1083 0.3131 0.148(5) Uiso 1 1 calc R . .
C16 C 0.3449(3) 1.0296(2) 0.14432(14) 0.0517(7) Uani 1 1 d . . .
C17 C 0.4107(4) 1.0877(3) 0.1071(2) 0.0731(10) Uani 1 1 d D A .
C18 C 0.3573(6) 1.0929(4) 0.0345(3) 0.1063(17) Uani 1 1 d . . .
H18 H 0.3976 1.1296 0.0065 0.661(2) Uiso 1 1 calc R A .
C19 C 0.2448(7) 1.0430(5) 0.0057(2) 0.115(2) Uani 1 1 d . A .
H19 H 0.2115 1.0465 -0.0418 0.661(2) Uiso 1 1 calc R . .
C20 C 0.1817(5) 0.9890(4) 0.0446(2) 0.0932(15) Uani 1 1 d . . .
H20 H 0.1067 0.9564 0.0235 0.661(2) Uiso 1 1 calc R A .
C21 C 0.2290(3) 0.9824(2) 0.11577(16) 0.0600(9) Uani 1 1 d . A .
C22 C 0.1528(4) 0.9300(3) 0.1593(2) 0.0729(10) Uani 1 1 d . . .
H22 H 0.2115 0.9130 0.2034 0.661(2) Uiso 1 1 calc R A .
C23 C 0.0897(5) 0.8370(3) 0.1247(3) 0.1174(19) Uani 1 1 d . A .
H23A H 0.0423 0.8065 0.1545 0.148(5) Uiso 1 1 calc R . .
H23B H 0.1557 0.7945 0.1168 0.148(5) Uiso 1 1 calc R . .
H23C H 0.0319 0.8523 0.0814 0.148(5) Uiso 1 1 calc R . .
C24 C 0.0473(4) 0.9965(4) 0.1746(3) 0.1051(16) Uani 1 1 d . A .
H24A H -0.0008 0.9634 0.2028 0.148(5) Uiso 1 1 calc R . .
H24B H -0.0099 1.0152 0.1319 0.148(5) Uiso 1 1 calc R . .
H24C H 0.0868 1.0524 0.1985 0.148(5) Uiso 1 1 calc R . .
C25 C 0.5256(18) 1.1424(17) 0.1517(13) 0.118(7) Uani 0.50(5) 1 d PDU A 1
H25 H 0.5566 1.1088 0.1957 0.661(2) Uiso 0.50(5) 1 calc PR A 1
C26 C 0.641(3) 1.161(2) 0.117(2) 0.158(8) Uani 0.50(5) 1 d PDU A 1
H26A H 0.7067 1.1967 0.1479 0.148(5) Uiso 0.50(5) 1 calc PR A 1
H26B H 0.6111 1.1964 0.0750 0.148(5) Uiso 0.50(5) 1 calc PR A 1
H26C H 0.6759 1.1008 0.1066 0.148(5) Uiso 0.50(5) 1 calc PR A 1
C27 C 0.476(3) 1.2435(16) 0.1658(19) 0.133(6) Uani 0.50(5) 1 d PDU A 1
H27A H 0.5470 1.2811 0.1909 0.148(5) Uiso 0.50(5) 1 calc PR A 1
H27B H 0.4118 1.2375 0.1926 0.148(5) Uiso 0.50(5) 1 calc PR A 1
H27C H 0.4389 1.2742 0.1226 0.148(5) Uiso 0.50(5) 1 calc PR A 1
C25' C 0.5290(13) 1.1466(11) 0.1357(12) 0.078(4) Uani 0.50(5) 1 d PDU A 2
H25' H 0.5747 1.1202 0.1802 0.661(2) Uiso 0.50(5) 1 calc PR A 2
C26' C 0.6181(17) 1.1418(16) 0.0835(13) 0.105(5) Uani 0.50(5) 1 d PDU A 2
H26D H 0.6942 1.1794 0.1006 0.148(5) Uiso 0.50(5) 1 calc PR A 2
H26E H 0.5726 1.1664 0.0396 0.148(5) Uiso 0.50(5) 1 calc PR A 2
H26F H 0.6423 1.0765 0.0783 0.148(5) Uiso 0.50(5) 1 calc PR A 2
C27' C 0.497(3) 1.2532(14) 0.145(2) 0.128(7) Uani 0.50(5) 1 d PDU A 2
H27D H 0.5746 1.2875 0.1643 0.148(5) Uiso 0.50(5) 1 calc PR A 2
H27E H 0.4384 1.2579 0.1753 0.148(5) Uiso 0.50(5) 1 calc PR A 2
H27F H 0.4566 1.2801 0.1007 0.148(5) Uiso 0.50(5) 1 calc PR A 2
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'
Cl Cl 0.1484 0.1585 '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
C1 P1 Cl1 102.5(4)
C1 P1 Cl3 91.6(5)
Cl1 P1 Cl3 76.9(4)
C1 P1 Cl2 86.5(4)
Cl1 P1 Cl2 90.0(5)
Cl3 P1 Cl2 166.1(5)
C1 P1A Cl1A 104.06(19)
C1 P1A Cl2A 86.9(2)
Cl1A P1A Cl2A 87.48(19)
C1 P1A Cl3A 89.4(2)
Cl1A P1A Cl3A 85.4(2)
Cl2A P1A Cl3A 170.9(3)
C1 N1 C2 110.0(2)
C1 N1 C16 127.8(2)
C2 N1 C16 121.9(2)
C1 N2 C3 109.8(2)
C1 N2 C4 128.5(2)
C3 N2 C4 121.5(2)
N2 C1 N1 106.0(2)
N2 C1 P1 133.3(3)
N1 C1 P1 120.5(3)
N2 C1 P1A 121.2(2)
N1 C1 P1A 132.6(2)
P1 C1 P1A 12.1(3)
C3 C2 N1 106.6(3)
C2 C3 N2 107.5(3)
C5 C4 C9 123.5(3)
C5 C4 N2 118.2(3)
C9 C4 N2 118.0(3)
C4 C5 C6 117.4(3)
C4 C5 C13 122.2(3)
C6 C5 C13 120.4(3)
C5 C6 C7 120.7(4)
C8 C7 C6 121.1(4)
C7 C8 C9 120.3(4)
C4 C9 C8 116.9(4)
C4 C9 C10' 124.3(4)
C8 C9 C10' 118.7(4)
C4 C9 C10 105.4(11)
C8 C9 C10 137.2(11)
C10' C9 C10 19.3(10)
C11 C10 C9 111(4)
C11 C10 C12 101(2)
C9 C10 C12 103(2)
C9 C10' C11' 109.2(5)
C9 C10' C12' 109.7(6)
C11' C10' C12' 110.9(6)
C14 C13 C15 110.6(4)
C14 C13 C5 109.3(3)
C15 C13 C5 110.6(4)
C17 C16 C21 124.3(3)
C17 C16 N1 118.0(3)
C21 C16 N1 117.6(3)
C16 C17 C18 115.8(4)
C16 C17 C25' 126.8(9)
C18 C17 C25' 117.4(10)
C16 C17 C25 114.4(10)
C18 C17 C25 129.6(10)
C25' C17 C25 12.6(13)
C19 C18 C17 119.8(4)
C18 C19 C20 122.3(4)
C19 C20 C21 120.2(5)
C16 C21 C20 117.4(4)
C16 C21 C22 122.5(3)
C20 C21 C22 120.0(4)
C21 C22 C24 109.4(3)
C21 C22 C23 112.9(4)
C24 C22 C23 109.5(4)
C17 C25 C27 107(2)
C17 C25 C26 115.3(18)
C27 C25 C26 105.2(13)
C17 C25' C27' 112.4(16)
C17 C25' C26' 108.0(12)
C27' C25' C26' 107.8(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.871(11)
P1 Cl1 2.018(8)
P1 Cl3 2.235(10)
P1 Cl2 2.492(10)
P1A C1 1.887(6)
P1A Cl1A 2.045(4)
P1A Cl2A 2.449(5)
P1A Cl3A 2.241(5)
N1 C1 1.356(3)
N1 C2 1.380(4)
N1 C16 1.452(4)
N2 C1 1.349(3)
N2 C3 1.376(4)
N2 C4 1.460(4)
C2 C3 1.354(4)
C4 C5 1.394(4)
C4 C9 1.391(4)
C5 C6 1.387(5)
C5 C13 1.532(5)
C6 C7 1.381(7)
C7 C8 1.378(7)
C8 C9 1.408(6)
C9 C10' 1.518(7)
C9 C10 1.63(2)
C10 C11 1.547(19)
C10 C12 1.583(19)
C10' C11' 1.503(8)
C10' C12' 1.567(8)
C13 C14 1.541(6)
C13 C15 1.551(6)
C16 C17 1.390(5)
C16 C21 1.399(5)
C17 C18 1.426(6)
C17 C25' 1.502(13)
C17 C25 1.539(17)
C18 C19 1.389(8)
C19 C20 1.362(8)
C20 C21 1.391(5)
C21 C22 1.504(5)
C22 C24 1.539(6)
C22 C23 1.550(5)
C25 C27 1.555(14)
C25 C26 1.560(11)
C25' C27' 1.549(12)
C25' C26' 1.555(10)
