#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178832 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/86/4108653.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_4108653
loop_
_publ_author_name
'Yuzhong Wang'
'Yaoming Xie'
'Pingrong Wei'
'R. Bruce King'
'Henry F. Schaefer, III'
'Paul v. R. Schleyer'
'Gregory H. Robinson'
_publ_section_title
;
 Carbene-Stabilized Diphosphorus
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14970
_journal_page_last               14971
_journal_paper_doi               10.1021/ja807828t
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C54 H72 N4 P2'
_chemical_formula_weight         839.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.687(2)
_cell_angle_beta                 112.794(2)
_cell_angle_gamma                108.936(2)
_cell_formula_units_Z            1
_cell_length_a                   10.9170(16)
_cell_length_b                   10.9711(16)
_cell_length_c                   12.6490(19)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.491
_cell_measurement_theta_min      2.674
_cell_volume                     1269.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16022
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       plate
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5516
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0492
_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)+(0.0656P)²+0.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                3650
_reflns_number_total             5516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807828t_si_001.cif
_cod_data_source_block           j1
_cod_database_code               4108653
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.56468(6) 0.54164(5) 0.09762(4) 0.04482(17) Uani 1 1 d . . .
N1 N 0.67753(16) 0.79752(14) 0.23535(12) 0.0399(4) Uani 1 1 d . . .
N2 N 0.55625(17) 0.79490(14) 0.05142(13) 0.0419(4) Uani 1 1 d . . .
C1 C 0.59464(18) 0.71135(16) 0.12010(14) 0.0350(4) Uani 1 1 d . . .
C2 C 0.6866(2) 0.92618(18) 0.23571(18) 0.0548(5) Uani 1 1 d . . .
H2 H 0.7351 1.0001 0.3024 0.093(3) Uiso 1 1 calc R . .
C3 C 0.6135(3) 0.92510(19) 0.12368(18) 0.0590(6) Uani 1 1 d . . .
H3 H 0.6025 0.9986 0.0978 0.093(3) Uiso 1 1 calc R . .
C4 C 0.4697(2) 0.75748(18) -0.07589(16) 0.0481(5) Uani 1 1 d . A .
C5 C 0.3198(3) 0.7091(2) -0.1216(2) 0.0654(6) Uani 1 1 d D . .
C6 C 0.2404(3) 0.6694(3) -0.2460(2) 0.0925(10) Uani 1 1 d . A .
H6 H 0.1396 0.6361 -0.2807 0.093(3) Uiso 1 1 calc R . .
C7 C 0.3076(5) 0.6784(4) -0.3173(3) 0.1097(12) Uani 1 1 d . . .
H7 H 0.2524 0.6478 -0.3998 0.093(3) Uiso 1 1 calc R A .
C8 C 0.4541(5) 0.7316(3) -0.2693(3) 0.1037(11) Uani 1 1 d . A .
H8 H 0.4977 0.7391 -0.3198 0.093(3) Uiso 1 1 calc R . .
C9 C 0.5415(3) 0.7752(2) -0.1468(2) 0.0696(7) Uani 1 1 d . . .
C10 C 0.7044(4) 0.8386(3) -0.0943(3) 0.0963(10) Uani 1 1 d . A .
H10 H 0.7406 0.8955 -0.0139 0.093(3) Uiso 1 1 calc R . .
C11 C 0.7581(6) 0.9287(5) -0.1630(4) 0.190(3) Uani 1 1 d . . .
H11A H 0.8623 0.9664 -0.1256 0.164(4) Uiso 1 1 calc R A .
H11B H 0.7246 0.9996 -0.1634 0.164(4) Uiso 1 1 calc R . .
H11C H 0.7213 0.8771 -0.2436 0.164(4) Uiso 1 1 calc R . .
C12 C 0.7692(4) 0.7381(4) -0.0809(5) 0.1577(18) Uani 1 1 d . . .
H12A H 0.8729 0.7831 -0.0466 0.164(4) Uiso 1 1 calc R A .
H12B H 0.7330 0.6779 -0.1578 0.164(4) Uiso 1 1 calc R . .
H12C H 0.7434 0.6882 -0.0297 0.164(4) Uiso 1 1 calc R . .
C13 C 0.2467(6) 0.7187(7) -0.0436(6) 0.0840(17) Uani 0.70 1 d PDU A 1
H13 H 0.3174 0.7919 0.0289 0.093(3) Uiso 0.70 1 calc PR A 1
C14 C 0.2079(8) 0.5940(9) -0.0069(6) 0.120(2) Uani 0.70 1 d PU A 1
H14A H 0.1623 0.6016 0.0434 0.164(4) Uiso 0.70 1 calc PR A 1
H14B H 0.2942 0.5802 0.0361 0.164(4) Uiso 0.70 1 calc PR A 1
H14C H 0.1421 0.5194 -0.0765 0.164(4) Uiso 0.70 1 calc PR A 1
C15 C 0.1147(6) 0.7505(6) -0.1002(6) 0.140(2) Uani 0.70 1 d PU A 1
H15A H 0.1412 0.8308 -0.1245 0.164(4) Uiso 0.70 1 calc PR A 1
H15B H 0.0788 0.7635 -0.0433 0.164(4) Uiso 0.70 1 calc PR A 1
H15C H 0.0404 0.6775 -0.1686 0.164(4) Uiso 0.70 1 calc PR A 1
C13' C 0.2505(14) 0.6687(10) -0.0350(13) 0.067(4) Uani 0.30 1 d PDU A 2
H13' H 0.3231 0.6547 0.0322 0.093(3) Uiso 0.30 1 calc PR A 2
C14' C 0.1079(10) 0.5417(10) -0.0846(12) 0.099(4) Uani 0.30 1 d PDU A 2
H14D H 0.1217 0.4658 -0.1157 0.164(4) Uiso 0.30 1 calc PR A 2
H14E H 0.0319 0.5540 -0.1471 0.164(4) Uiso 0.30 1 calc PR A 2
H14F H 0.0815 0.5263 -0.0217 0.164(4) Uiso 0.30 1 calc PR A 2
C15' C 0.2300(13) 0.7942(10) 0.0170(11) 0.094(3) Uani 0.30 1 d PDU A 2
H15D H 0.3159 0.8738 0.0404 0.164(4) Uiso 0.30 1 calc PR A 2
H15E H 0.2135 0.7833 0.0851 0.164(4) Uiso 0.30 1 calc PR A 2
H15F H 0.1482 0.8022 -0.0430 0.164(4) Uiso 0.30 1 calc PR A 2
C16 C 0.7310(2) 0.75548(17) 0.34136(15) 0.0430(4) Uani 1 1 d . B .
C17 C 0.6429(2) 0.72036(19) 0.39789(17) 0.0511(5) Uani 1 1 d . . .
C18 C 0.6988(3) 0.6851(3) 0.5029(2) 0.0728(7) Uani 1 1 d . . .
H18 H 0.6430 0.6617 0.5432 0.093(3) Uiso 1 1 calc R . .
C19 C 0.8340(3) 0.6844(3) 0.5480(2) 0.0883(9) Uani 1 1 d . . .
H19 H 0.8694 0.6609 0.6186 0.093(3) Uiso 1 1 calc R . .
C20 C 0.9180(3) 0.7178(3) 0.4903(2) 0.0798(8) Uani 1 1 d . B .
H20 H 1.0096 0.7160 0.5221 0.093(3) Uiso 1 1 calc R . .
C21 C 0.8692(2) 0.7545(2) 0.38474(18) 0.0552(5) Uani 1 1 d D . .
C22 C 0.968(2) 0.7887(16) 0.326(2) 0.066(5) Uani 0.35(2) 1 d PDU B 1
H22 H 0.9107 0.8028 0.2507 0.093(3) Uiso 0.35(2) 1 calc PR B 1
C23 C 1.016(2) 0.6809(16) 0.291(2) 0.120(6) Uani 0.35(2) 1 d PDU B 1
H23A H 1.0750 0.7131 0.2519 0.164(4) Uiso 0.35(2) 1 calc PR B 1
H23B H 0.9316 0.6016 0.2370 0.164(4) Uiso 0.35(2) 1 calc PR B 1
H23C H 1.0705 0.6600 0.3608 0.164(4) Uiso 0.35(2) 1 calc PR B 1
C24 C 1.099(3) 0.9218(16) 0.395(2) 0.106(6) Uani 0.35(2) 1 d PDU B 1
H24A H 1.1568 0.9395 0.3528 0.164(4) Uiso 0.35(2) 1 calc PR B 1
H24B H 1.1563 0.9173 0.4729 0.164(4) Uiso 0.35(2) 1 calc PR B 1
H24C H 1.0665 0.9924 0.4020 0.164(4) Uiso 0.35(2) 1 calc PR B 1
C22' C 0.9592(11) 0.7970(10) 0.3186(11) 0.073(3) Uani 0.65(2) 1 d PDU B 2
H22' H 0.8937 0.7648 0.2327 0.093(3) Uiso 0.65(2) 1 calc PR B 2
C23' C 1.0684(12) 0.7317(16) 0.3446(12) 0.119(3) Uani 0.65(2) 1 d PDU B 2
H23D H 1.0170 0.6360 0.3140 0.164(4) Uiso 0.65(2) 1 calc PR B 2
H23E H 1.1274 0.7551 0.4293 0.164(4) Uiso 0.65(2) 1 calc PR B 2
H23F H 1.1291 0.7630 0.3069 0.164(4) Uiso 0.65(2) 1 calc PR B 2
C24' C 1.0353(12) 0.9474(8) 0.3518(10) 0.104(3) Uani 0.65(2) 1 d PDU B 2
H24D H 0.9650 0.9847 0.3199 0.164(4) Uiso 0.65(2) 1 calc PR B 2
H24E H 1.1034 0.9710 0.3194 0.164(4) Uiso 0.65(2) 1 calc PR B 2
H24F H 1.0860 0.9823 0.4371 0.164(4) Uiso 0.65(2) 1 calc PR B 2
C25 C 0.4938(2) 0.7235(2) 0.3496(2) 0.0624(6) Uani 1 1 d . . .
H25 H 0.4645 0.7264 0.2665 0.093(3) Uiso 1 1 calc R . .
C26 C 0.3798(3) 0.5979(3) 0.3501(3) 0.1033(10) Uani 1 1 d . . .
H26A H 0.2871 0.6035 0.3186 0.164(4) Uiso 1 1 calc R . .
H26B H 0.4072 0.5914 0.4304 0.164(4) Uiso 1 1 calc R . .
H26C H 0.3737 0.5199 0.3016 0.164(4) Uiso 1 1 calc R . .
C27 C 0.4962(4) 0.8485(3) 0.4185(3) 0.0994(10) Uani 1 1 d . . .
H27A H 0.4007 0.8482 0.3851 0.164(4) Uiso 1 1 calc R . .
H27B H 0.5628 0.9270 0.4130 0.164(4) Uiso 1 1 calc R . .
H27C H 0.5267 0.8492 0.5007 0.164(4) 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'
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_3
C1 P1 P1 103.19(6) 2_665
C2 N1 C1 110.95(14) .
C2 N1 C16 124.07(15) .
C1 N1 C16 124.54(14) .
C1 N2 C3 110.21(15) .
C1 N2 C4 126.78(14) .
C3 N2 C4 123.01(14) .
N2 C1 N1 103.12(13) .
N2 C1 P1 137.61(13) .
N1 C1 P1 119.27(12) .
C3 C2 N1 107.54(16) .
C2 C3 N2 108.17(16) .
C5 C4 C9 123.4(2) .
C5 C4 N2 118.57(19) .
C9 C4 N2 118.0(2) .
C4 C5 C6 116.3(2) .
C4 C5 C13 122.2(3) .
C6 C5 C13 120.8(3) .
C4 C5 C13' 118.2(5) .
C6 C5 C13' 123.6(5) .
C13 C5 C13' 21.6(3) .
C7 C6 C5 121.3(3) .
C8 C7 C6 120.5(3) .
C7 C8 C9 122.0(3) .
C4 C9 C8 116.3(3) .
C4 C9 C10 122.2(2) .
C8 C9 C10 121.5(3) .
C9 C10 C12 112.5(3) .
C9 C10 C11 113.0(3) .
C12 C10 C11 110.1(4) .
C14 C13 C5 110.2(4) .
C14 C13 C15 110.4(5) .
C5 C13 C15 113.8(5) .
C14' C13' C15' 110.2(10) .
C14' C13' C5 118.4(10) .
C15' C13' C5 107.0(7) .
C17 C16 C21 122.92(18) .
C17 C16 N1 118.05(17) .
C21 C16 N1 119.01(17) .
C18 C17 C16 117.2(2) .
C18 C17 C25 120.9(2) .
C16 C17 C25 121.88(18) .
C19 C18 C17 121.1(2) .
C18 C19 C20 120.6(2) .
C19 C20 C21 121.4(2) .
C16 C21 C20 116.7(2) .
C16 C21 C22 125.3(9) .
C20 C21 C22 118.0(9) .
C16 C21 C22' 119.4(5) .
C20 C21 C22' 123.8(5) .
C22 C21 C22' 6.2(12) .
C21 C22 C24 112.9(14) .
C21 C22 C23 117.3(13) .
C24 C22 C23 110.2(12) .
C24' C22' C23' 111.0(7) .
C24' C22' C21 111.2(6) .
C23' C22' C21 109.6(8) .
C17 C25 C27 111.5(2) .
C17 C25 C26 112.0(2) .
C27 C25 C26 109.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.7504(17) .
P1 P1 2.2052(10) 2_665
N1 C2 1.382(2) .
N1 C1 1.393(2) .
N1 C16 1.437(2) .
N2 C1 1.387(2) .
N2 C3 1.393(2) .
N2 C4 1.439(2) .
C2 C3 1.326(3) .
C4 C5 1.388(3) .
C4 C9 1.393(3) .
C5 C6 1.399(3) .
C5 C13 1.504(6) .
C5 C13' 1.584(13) .
C6 C7 1.360(5) .
C7 C8 1.351(5) .
C8 C9 1.388(4) .
C9 C10 1.504(4) .
C10 C12 1.484(5) .
C10 C11 1.515(4) .
C13 C14 1.479(7) .
C13 C15 1.516(7) .
C13' C14' 1.547(13) .
C13' C15' 1.575(11) .
C16 C17 1.393(3) .
C16 C21 1.396(3) .
C17 C18 1.390(3) .
C17 C25 1.515(3) .
C18 C19 1.365(4) .
C19 C20 1.368(4) .
C20 C21 1.393(3) .
C21 C22 1.511(15) .
C21 C22' 1.522(9) .
C22 C24 1.522(14) .
C22 C23 1.525(13) .
C22' C24' 1.506(8) .
C22' C23' 1.532(9) .
C25 C27 1.524(3) .
C25 C26 1.532(3) .
