#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:05:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180222 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/08/7110897.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110897
loop_
_publ_author_name
'Vohs, Jason K.'
'Wei, Pingrong'
'Su, Jianrui'
'Beck, Brent C.'
'Goodwin, Sonya D.'
'Robinson, Gregory H.'
_publ_section_title
;
 Formation of a diphosphine: synthesis and molecular structure of
 bis(tetraphenylbutadienyl)diphosphine, (Ph4C4)P--P(C4Ph4)
;
_journal_issue                   12
_journal_name_full               'Chemical Communications'
_journal_page_first              1037
_journal_paper_doi               10.1039/b001257m
_journal_year                    2000
_chemical_formula_sum            'C59 H47 P2'
_chemical_formula_weight         817.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 98.078(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.092(4)
_cell_length_b                   13.6821(16)
_cell_length_c                   24.311(2)
_cell_measurement_temperature    293(2)
_cell_volume                     9251.4(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16475
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.132
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00012(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         6568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                4061
_reflns_number_total             6568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001257msup1.cif
_cod_data_source_block           j
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7110897
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.40374(3) 0.82134(6) 0.10258(3) 0.0484(2) Uani 1 1 d .
P2 P 0.33220(3) 0.83295(6) 0.05241(3) 0.0533(3) Uani 1 1 d .
C1 C 0.41294(9) 0.6914(2) 0.10003(10) 0.0436(7) Uani 1 1 d .
C2 C 0.42349(10) 0.6426(2) 0.04877(11) 0.0474(7) Uani 1 1 d .
C3 C 0.45722(11) 0.6823(2) 0.01837(12) 0.0579(8) Uani 1 1 d .
H3A H 0.4719 0.7413 0.0296 0.069 Uiso 1 1 calc R
C4 C 0.46937(13) 0.6359(3) -0.02795(13) 0.0705(10) Uani 1 1 d .
H4A H 0.4923 0.6633 -0.0474 0.085 Uiso 1 1 calc R
C5 C 0.44784(14) 0.5502(3) -0.04529(14) 0.0774(11) Uani 1 1 d .
H5A H 0.4564 0.5183 -0.0762 0.093 Uiso 1 1 calc R
C6 C 0.41359(15) 0.5109(3) -0.01725(15) 0.0836(12) Uani 1 1 d .
H6A H 0.3982 0.4532 -0.0298 0.100 Uiso 1 1 calc R
C7 C 0.40162(12) 0.5565(2) 0.02967(13) 0.0672(9) Uani 1 1 d .
H7A H 0.3785 0.5287 0.0486 0.081 Uiso 1 1 calc R
C8 C 0.41544(9) 0.65166(19) 0.15143(11) 0.0414(7) Uani 1 1 d .
C9 C 0.42900(11) 0.5476(2) 0.16393(11) 0.0446(7) Uani 1 1 d .
C10 C 0.39408(13) 0.4761(2) 0.16299(14) 0.0708(10) Uani 1 1 d .
H10A H 0.3618 0.4936 0.1573 0.085 Uiso 1 1 calc R
C11 C 0.40681(17) 0.3785(3) 0.17047(16) 0.0853(12) Uani 1 1 d .
H11A H 0.3830 0.3313 0.1703 0.102 Uiso 1 1 calc R
C12 C 0.45343(19) 0.3519(3) 0.17793(16) 0.0891(13) Uani 1 1 d .
H12A H 0.4618 0.2863 0.1817 0.107 Uiso 1 1 calc R
C13 C 0.48827(15) 0.4219(3) 0.17984(16) 0.0872(12) Uani 1 1 d .
H13A H 0.5205 0.4037 0.1860 0.105 Uiso 1 1 calc R
C14 C 0.47627(12) 0.5195(2) 0.17272(13) 0.0646(9) Uani 1 1 d .
H14A H 0.5004 0.5664 0.1739 0.077 Uiso 1 1 calc R
C15 C 0.40680(9) 0.72275(19) 0.19441(10) 0.0402(7) Uani 1 1 d .
C16 C 0.41425(10) 0.6999(2) 0.25485(11) 0.0421(7) Uani 1 1 d .
C17 C 0.38920(11) 0.6273(2) 0.27769(12) 0.0549(8) Uani 1 1 d .
H17A H 0.3681 0.5879 0.2545 0.066 Uiso 1 1 calc R
C18 C 0.39482(14) 0.6121(2) 0.33450(14) 0.0714(10) Uani 1 1 d .
H18A H 0.3777 0.5626 0.3492 0.086 Uiso 1 1 calc R
C19 C 0.42543(15) 0.6696(3) 0.36872(13) 0.0741(11) Uani 1 1 d .
H19A H 0.4286 0.6602 0.4070 0.089 Uiso 1 1 calc R
C20 C 0.45166(13) 0.7412(2) 0.34733(12) 0.0644(9) Uani 1 1 d .
H20A H 0.4731 0.7794 0.3709 0.077 Uiso 1 1 calc R
C21 C 0.44606(10) 0.7562(2) 0.29072(11) 0.0504(8) Uani 1 1 d .
H21A H 0.4639 0.8048 0.2763 0.061 Uiso 1 1 calc R
C22 C 0.39560(10) 0.8144(2) 0.17450(11) 0.0431(7) Uani 1 1 d .
C23 C 0.38434(11) 0.9003(2) 0.20699(12) 0.0488(8) Uani 1 1 d .
C24 C 0.35585(11) 0.8933(2) 0.24914(12) 0.0573(8) Uani 1 1 d .
H24A H 0.3420 0.8336 0.2559 0.069 Uiso 1 1 calc R
C25 C 0.34781(13) 0.9731(3) 0.28105(14) 0.0713(10) Uani 1 1 d .
H25A H 0.3292 0.9660 0.3096 0.086 Uiso 1 1 calc R
C26 C 0.36643(17) 1.0613(3) 0.27171(17) 0.0913(13) Uani 1 1 d .
H26A H 0.3604 1.1147 0.2934 0.110 Uiso 1 1 calc R
C27 C 0.39420(18) 1.0720(3) 0.23014(19) 0.1037(14) Uani 1 1 d .
H27A H 0.4072 1.1327 0.2237 0.124 Uiso 1 1 calc R
C28 C 0.40303(14) 0.9919(2) 0.19744(14) 0.0769(11) Uani 1 1 d .
H28A H 0.4216 0.9999 0.1690 0.092 Uiso 1 1 calc R
C29 C 0.28971(10) 0.7942(2) 0.09671(11) 0.0496(8) Uani 1 1 d .
C30 C 0.28119(10) 0.6915(2) 0.10960(13) 0.0542(8) Uani 1 1 d .
C31 C 0.27641(12) 0.6198(3) 0.06919(16) 0.0780(10) Uani 1 1 d .
H31A H 0.2801 0.6358 0.0328 0.094 Uiso 1 1 calc R
C32 C 0.26614(14) 0.5240(3) 0.0825(2) 0.0951(13) Uani 1 1 d .
H32A H 0.2624 0.4765 0.0548 0.114 Uiso 1 1 calc R
C33 C 0.26155(13) 0.4992(3) 0.1359(2) 0.0926(13) Uani 1 1 d .
H33A H 0.2550 0.4348 0.1445 0.111 Uiso 1 1 calc R
C34 C 0.26656(12) 0.5682(3) 0.17653(18) 0.0791(11) Uani 1 1 d .
H34A H 0.2634 0.5511 0.2129 0.095 Uiso 1 1 calc R
C35 C 0.27633(11) 0.6638(2) 0.16357(14) 0.0619(9) Uani 1 1 d .
H35A H 0.2797 0.7107 0.1916 0.074 Uiso 1 1 calc R
C36 C 0.26442(11) 0.8727(2) 0.11160(11) 0.0510(8) Uani 1 1 d .
C37 C 0.21992(11) 0.8624(2) 0.13840(13) 0.0533(8) Uani 1 1 d .
C38 C 0.21848(12) 0.8889(2) 0.19281(15) 0.0710(10) Uani 1 1 d .
H38A H 0.2456 0.9164 0.2133 0.085 Uiso 1 1 calc R
C39 C 0.17759(15) 0.8756(3) 0.21767(17) 0.0829(11) Uani 1 1 d .
H39A H 0.1774 0.8940 0.2545 0.099 Uiso 1 1 calc R
C40 C 0.13785(15) 0.8357(3) 0.1883(2) 0.0881(12) Uani 1 1 d .
H40A H 0.1103 0.8269 0.2049 0.106 Uiso 1 1 calc R
C41 C 0.13819(13) 0.8083(3) 0.1342(2) 0.0942(13) Uani 1 1 d .
H41A H 0.1109 0.7805 0.1142 0.113 Uiso 1 1 calc R
C42 C 0.17937(13) 0.8218(3) 0.10883(15) 0.0809(11) Uani 1 1 d .
H42A H 0.1794 0.8034 0.0720 0.097 Uiso 1 1 calc R
C43 C 0.28181(10) 0.9671(2) 0.09386(11) 0.0502(8) Uani 1 1 d .
C44 C 0.25784(11) 1.0606(2) 0.10563(14) 0.0577(8) Uani 1 1 d .
C45 C 0.26529(16) 1.1033(3) 0.15657(17) 0.0920(12) Uani 1 1 d .
H45A H 0.2858 1.0736 0.1851 0.110 Uiso 1 1 calc R
C46 C 0.2426(2) 1.1916(3) 0.1670(2) 0.1097(15) Uani 1 1 d .
H46A H 0.2478 1.2194 0.2022 0.132 Uiso 1 1 calc R
C47 C 0.21352(18) 1.2359(3) 0.1258(3) 0.1140(17) Uani 1 1 d .
H47A H 0.1983 1.2942 0.1325 0.137 Uiso 1 1 calc R
C48 C 0.2065(2) 1.1953(4) 0.0750(3) 0.147(2) Uani 1 1 d .
H48A H 0.1872 1.2268 0.0462 0.177 Uiso 1 1 calc R
C49 C 0.22782(15) 1.1073(3) 0.06523(18) 0.1102(15) Uani 1 1 d .
H49A H 0.2215 1.0792 0.0301 0.132 Uiso 1 1 calc R
C50 C 0.31916(11) 0.9594(2) 0.06405(11) 0.0518(8) Uani 1 1 d .
C51 C 0.34553(11) 1.0388(2) 0.03984(13) 0.0564(8) Uani 1 1 d .
C52 C 0.36032(13) 1.1232(3) 0.06878(15) 0.0746(10) Uani 1 1 d .
H52A H 0.3523 1.1326 0.1042 0.090 Uiso 1 1 calc R
C53 C 0.38685(14) 1.1939(3) 0.04580(18) 0.0916(12) Uani 1 1 d .
H53A H 0.3973 1.2492 0.0663 0.110 Uiso 1 1 calc R
C54 C 0.39767(15) 1.1826(4) -0.0064(2) 0.0969(14) Uani 1 1 d .
H54A H 0.4155 1.2302 -0.0216 0.116 Uiso 1 1 calc R
C55 C 0.38255(14) 1.1018(4) -0.03685(18) 0.0901(13) Uani 1 1 d .
H55A H 0.3894 1.0954 -0.0730 0.108 Uiso 1 1 calc R
C56 C 0.35675(12) 1.0288(3) -0.01387(14) 0.0698(10) Uani 1 1 d .
H56A H 0.3470 0.9733 -0.0345 0.084 Uiso 1 1 calc R
C57 C 0.5020(3) 1.0007(11) -0.0355(6) 0.277(12) Uani 1 1 d .
H57A H 0.4872 1.0597 -0.0521 0.332 Uiso 1 1 calc R
H57B H 0.5356 1.0007 -0.0410 0.332 Uiso 1 1 calc R
C58 C 0.4797(3) 0.9211(9) -0.0606(7) 0.302(10) Uani 1 1 d .
H58A H 0.4459 0.9233 -0.0562 0.362 Uiso 1 1 calc R
H58B H 0.4933 0.8627 -0.0420 0.362 Uiso 1 1 calc R
C59 C 0.4840(3) 0.9141(9) -0.1223(4) 0.252(5) Uani 1 1 d .
H59A H 0.4673 0.8570 -0.1377 0.379 Uiso 1 1 calc R
H59B H 0.5173 0.9095 -0.1269 0.379 Uiso 1 1 calc R
H59C H 0.4702 0.9712 -0.1410 0.379 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'
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
C22 P1 C1 91.16(12) .
C22 P1 P2 108.13(9) .
C1 P1 P2 100.16(9) .
C29 P2 C50 91.26(14) .
C29 P2 P1 106.14(10) .
C50 P2 P1 99.92(10) .
C8 C1 C2 127.2(3) .
C8 C1 P1 110.7(2) .
C2 C1 P1 121.4(2) .
C7 C2 C3 117.3(3) .
C7 C2 C1 122.5(3) .
C3 C2 C1 120.2(3) .
C4 C3 C2 121.4(3) .
C5 C4 C3 120.0(3) .
C4 C5 C6 119.9(3) .
C5 C6 C7 120.3(3) .
C2 C7 C6 121.0(3) .
C1 C8 C15 113.4(2) .
C1 C8 C9 123.3(2) .
C15 C8 C9 123.2(2) .
C14 C9 C10 118.3(3) .
C14 C9 C8 120.8(3) .
C10 C9 C8 120.7(3) .
C9 C10 C11 120.6(3) .
C12 C11 C10 120.4(4) .
C11 C12 C13 119.6(4) .
C12 C13 C14 120.8(4) .
C9 C14 C13 120.3(3) .
C22 C15 C8 114.1(2) .
C22 C15 C16 122.4(2) .
C8 C15 C16 123.2(2) .
C17 C16 C21 117.8(3) .
C17 C16 C15 122.7(3) .
C21 C16 C15 119.5(2) .
C16 C17 C18 121.2(3) .
C19 C18 C17 119.8(3) .
C18 C19 C20 120.6(3) .
C19 C20 C21 119.5(3) .
C20 C21 C16 121.1(3) .
C15 C22 C23 126.7(2) .
C15 C22 P1 109.80(19) .
C23 C22 P1 123.1(2) .
C24 C23 C28 117.1(3) .
C24 C23 C22 121.9(3) .
C28 C23 C22 120.9(3) .
C25 C24 C23 121.2(3) .
C26 C25 C24 121.2(4) .
C25 C26 C27 119.6(4) .
C26 C27 C28 120.2(4) .
C23 C28 C27 120.7(4) .
C36 C29 C30 126.2(3) .
C36 C29 P2 110.0(2) .
C30 C29 P2 123.6(2) .
C31 C30 C35 117.7(3) .
C31 C30 C29 122.1(3) .
C35 C30 C29 120.2(3) .
C30 C31 C32 120.5(4) .
C33 C32 C31 120.3(4) .
C34 C33 C32 120.4(4) .
C33 C34 C35 119.7(4) .
C34 C35 C30 121.5(3) .
C29 C36 C43 114.0(3) .
C29 C36 C37 122.7(3) .
C43 C36 C37 123.0(3) .
C42 C37 C38 118.3(3) .
C42 C37 C36 119.5(3) .
C38 C37 C36 122.2(3) .
C37 C38 C39 121.5(3) .
C40 C39 C38 119.8(4) .
C39 C40 C41 120.0(4) .
C40 C41 C42 120.3(4) .
C37 C42 C41 120.0(4) .
C50 C43 C36 113.7(3) .
C50 C43 C44 124.8(3) .
C36 C43 C44 121.4(3) .
C45 C44 C49 117.1(3) .
C45 C44 C43 121.9(3) .
C49 C44 C43 121.0(3) .
C44 C45 C46 121.2(4) .
C47 C46 C45 119.8(5) .
C46 C47 C48 119.5(5) .
C47 C48 C49 120.5(5) .
C44 C49 C48 121.7(4) .
C43 C50 C51 128.4(3) .
C43 C50 P2 110.3(2) .
C51 C50 P2 121.2(2) .
C52 C51 C56 117.8(3) .
C52 C51 C50 122.7(3) .
C56 C51 C50 119.5(3) .
C51 C52 C53 121.1(4) .
C54 C53 C52 120.1(4) .
C53 C54 C55 120.5(4) .
C54 C55 C56 120.2(4) .
C51 C56 C55 120.2(4) .
C58 C57 C57 110.1(11) 5_675
C57 C58 C59 113.3(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C22 1.797(3) .
P1 C1 1.799(3) .
P1 P2 2.2051(11) .
P2 C29 1.796(3) .
P2 C50 1.799(3) .
C1 C8 1.356(3) .
C1 C2 1.480(4) .
C2 C7 1.379(4) .
C2 C3 1.391(4) .
C3 C4 1.377(4) .
C4 C5 1.359(5) .
C5 C6 1.365(5) .
C6 C7 1.382(4) .
C8 C15 1.472(3) .
C8 C9 1.494(4) .
C9 C14 1.370(4) .
C9 C10 1.383(4) .
C10 C11 1.387(4) .
C11 C12 1.347(5) .
C12 C13 1.365(5) .
C13 C14 1.382(4) .
C15 C22 1.365(3) .
C15 C16 1.488(3) .
C16 C17 1.379(4) .
C16 C21 1.390(4) .
C17 C18 1.384(4) .
C18 C19 1.360(5) .
C19 C20 1.372(4) .
C20 C21 1.379(4) .
C22 C23 1.475(4) .
C23 C24 1.389(4) .
C23 C28 1.390(4) .
C24 C25 1.377(4) .
C25 C26 1.347(5) .
C26 C27 1.369(5) .
C27 C28 1.396(5) .
C29 C36 1.364(4) .
C29 C30 1.467(4) .
C30 C31 1.382(4) .
C30 C35 1.391(4) .
C31 C32 1.391(5) .
C32 C33 1.365(5) .
C33 C34 1.359(5) .
C34 C35 1.383(4) .
C36 C43 1.467(4) .
C36 C37 1.495(4) .
C37 C42 1.376(4) .
C37 C38 1.378(4) .
C38 C39 1.383(4) .
C39 C40 1.353(5) .
C40 C41 1.370(5) .
C41 C42 1.397(5) .
C43 C50 1.360(4) .
C43 C44 1.492(4) .
C44 C45 1.359(4) .
C44 C49 1.361(5) .
C45 C46 1.405(5) .
C46 C47 1.344(6) .
C47 C48 1.343(6) .
C48 C49 1.380(6) .
C50 C51 1.482(4) .
C51 C52 1.385(4) .
C51 C56 1.392(4) .
C52 C53 1.386(5) .
C53 C54 1.355(5) .
C54 C55 1.363(5) .
C55 C56 1.396(5) .
C57 C58 1.359(19) .
C57 C57 1.75(3) 5_675
C58 C59 1.525(15) .
