#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:26:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179412 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/09/4330927.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_4330927
loop_
_publ_author_name
'Nick A. Giffin'
'Arthur D. Hendsbee'
'Tracey L. Roemmele'
'Michael D. Lumsden'
'Cory C. Pye'
'Jason D. Masuda'
_publ_contact_author_address
; The Maritimes Centre for Green Chemistry
  Department of Chemistry
  Saint Mary's University
  923 Robie St
  Halifax, Nova Scotia
  B3H 3C3 
  Canada
;
_publ_contact_author_email       jason.masuda@smu.ca
_publ_contact_author_name        'Jason D. Masuda'
_publ_section_title
;
 Preparation of a Diphosphine with Persistent Phosphinyl Radical Character
 in Solution: Characterization, Reactivity with O2, S8, Se, Te, and P4,
 and Electronic Structure Calculations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11837
_journal_page_last               11850
_journal_paper_doi               10.1021/ic301758k
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C52 H76 N4 P6'
_chemical_formula_sum            'C52 H76 N4 P6'
_chemical_formula_weight         942.99
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.954(3)
_cell_length_b                   12.954(3)
_cell_length_c                   35.031(12)
_cell_measurement_reflns_used    9033
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.22
_cell_volume                     5878(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            71003
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_description       block
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          .3226
_exptl_crystal_size_mid          .3014
_exptl_crystal_size_min          .2821
_platon_squeeze_details
;
The unit cell contains 4 toluene molecules which have been treated as a diffuse 
contribution to the overall scattering without specific atom positions by 
SQUEEZE/PLATON.
;
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack (1983), 3049 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         7296
_refine_ls_number_restraints     2064
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0631
_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)+(0.0958P)²+4.9800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                6406
_reflns_number_total             7296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301758k_si_001_8.cif
_cod_data_source_block           Compound_8
_cod_original_cell_volume        5878.4(28)
_cod_database_code               4330927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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
C22 C 0.7549(5) 0.1593(6) 0.0891(2) 0.0384(8) Uani 0.623(6) 1 d PU A 1
H22A H 0.8218 0.1224 0.0932 0.046 Uiso 0.623(6) 1 calc PR A 1
C23 C 0.7288(5) 0.2107(5) 0.12605(19) 0.0420(9) Uani 0.623(6) 1 d PU A 1
H23A H 0.7159 0.1581 0.1456 0.063 Uiso 0.623(6) 1 calc PR A 1
H23B H 0.6669 0.2532 0.1227 0.063 Uiso 0.623(6) 1 calc PR A 1
H23C H 0.7865 0.2546 0.1340 0.063 Uiso 0.623(6) 1 calc PR A 1
C24 C 0.6733(6) 0.0753(6) 0.0795(2) 0.0478(10) Uani 0.623(6) 1 d PU A 1
H24A H 0.6912 0.0422 0.0552 0.072 Uiso 0.623(6) 1 calc PR A 1
H24B H 0.6050 0.1073 0.0774 0.072 Uiso 0.623(6) 1 calc PR A 1
H24C H 0.6723 0.0232 0.0998 0.072 Uiso 0.623(6) 1 calc PR A 1
C22B C 0.7613(9) 0.1386(9) 0.0742(4) 0.0379(9) Uani 0.377(6) 1 d PU A 2
H22B H 0.8187 0.1343 0.0932 0.045 Uiso 0.377(6) 1 calc PR A 2
C23B C 0.6632(9) 0.1432(9) 0.0951(3) 0.0432(11) Uani 0.377(6) 1 d PU A 2
H23D H 0.6633 0.2033 0.1121 0.065 Uiso 0.377(6) 1 calc PR A 2
H23E H 0.6546 0.0802 0.1102 0.065 Uiso 0.377(6) 1 calc PR A 2
H23F H 0.6060 0.1493 0.0769 0.065 Uiso 0.377(6) 1 calc PR A 2
C24B C 0.7628(9) 0.0408(9) 0.0501(3) 0.0435(11) Uani 0.377(6) 1 d PU A 2
H24D H 0.8312 0.0323 0.0386 0.065 Uiso 0.377(6) 1 calc PR A 2
H24E H 0.7107 0.0461 0.0299 0.065 Uiso 0.377(6) 1 calc PR A 2
H24F H 0.7474 -0.0188 0.0663 0.065 Uiso 0.377(6) 1 calc PR A 2
P1 P 1.01761(6) 0.17142(6) 0.07799(2) 0.02148(17) Uani 1 1 d U . .
P2 P 1.14551(6) 0.21779(6) 0.03627(2) 0.02366(18) Uani 1 1 d U . .
P3 P 1.16235(7) 0.05756(6) 0.01404(2) 0.02412(18) Uani 1 1 d U . .
N1 N 1.0691(2) 0.2019(2) 0.12095(8) 0.0288(5) Uani 1 1 d U . .
N2 N 0.9419(2) 0.2779(2) 0.07951(8) 0.0288(5) Uani 1 1 d U . .
C1 C 0.8613(3) 0.2973(3) 0.05259(10) 0.0316(6) Uani 1 1 d U A .
C2 C 0.7715(3) 0.2349(3) 0.05347(12) 0.0401(7) Uani 1 1 d U . .
C3 C 0.6948(3) 0.2540(4) 0.02608(13) 0.0472(8) Uani 1 1 d U A .
H3A H 0.6346 0.2121 0.0257 0.057 Uiso 1 1 calc R . .
C4 C 0.7050(3) 0.3318(4) -0.00004(12) 0.0448(7) Uani 1 1 d U . .
H4 H 0.6518 0.3433 -0.0182 0.054 Uiso 1 1 calc R A .
C5 C 0.7910(3) 0.3933(3) -0.00022(11) 0.0405(7) Uani 1 1 d U A .
H5A H 0.7960 0.4480 -0.0182 0.049 Uiso 1 1 calc R . .
C6 C 0.8709(3) 0.3769(3) 0.02536(10) 0.0326(6) Uani 1 1 d U . .
C7 C 1.1214(3) 0.1268(3) 0.14400(10) 0.0313(6) Uani 1 1 d U B .
C8 C 1.2294(3) 0.1329(3) 0.14747(10) 0.0358(6) Uani 1 1 d U . .
C9 C 1.2793(4) 0.0580(3) 0.16905(12) 0.0439(7) Uani 1 1 d U . .
H9 H 1.3523 0.0609 0.1717 0.053 Uiso 1 1 calc R . .
C19 C 0.9662(3) 0.4451(3) 0.02287(12) 0.0390(7) Uani 1 1 d U A .
H19A H 1.0207 0.4146 0.0396 0.047 Uiso 1 1 calc R . .
C20 C 0.9420(4) 0.5526(3) 0.03748(13) 0.0459(8) Uani 1 1 d U . .
H20A H 0.9153 0.5481 0.0636 0.069 Uiso 1 1 calc R A .
H20B H 0.8899 0.5847 0.0210 0.069 Uiso 1 1 calc R . .
H20C H 1.0050 0.5945 0.0373 0.069 Uiso 1 1 calc R . .
C10 C 1.2259(4) -0.0196(4) 0.18654(12) 0.0476(8) Uani 1 1 d U . .
H10 H 1.2620 -0.0707 0.2007 0.057 Uiso 1 1 calc R . .
C11 C 1.1194(4) -0.0241(3) 0.18379(12) 0.0442(7) Uani 1 1 d U B .
H11A H 1.0831 -0.0779 0.1964 0.053 Uiso 1 1 calc R . .
C12 C 1.0642(3) 0.0495(3) 0.16260(10) 0.0371(6) Uani 1 1 d U . .
C13A C 0.9519(6) 0.0435(6) 0.1607(3) 0.0371(9) Uani 0.692(13) 1 d PU B 1
H13A H 0.9272 0.1019 0.1444 0.045 Uiso 0.692(13) 1 calc PR B 1
C14A C 0.9099(6) 0.0610(7) 0.20151(19) 0.0442(10) Uani 0.692(13) 1 d PU B 1
H14A H 0.8343 0.0601 0.2010 0.066 Uiso 0.692(13) 1 calc PR B 1
H14B H 0.9339 0.1280 0.2110 0.066 Uiso 0.692(13) 1 calc PR B 1
H14C H 0.9350 0.0061 0.2184 0.066 Uiso 0.692(13) 1 calc PR B 1
C15A C 0.9137(6) -0.0552(6) 0.1431(2) 0.0442(9) Uani 0.692(13) 1 d PU B 1
H15A H 0.9446 -0.0636 0.1177 0.066 Uiso 0.692(13) 1 calc PR B 1
H15B H 0.8384 -0.0526 0.1407 0.066 Uiso 0.692(13) 1 calc PR B 1
H15C H 0.9333 -0.1136 0.1593 0.066 Uiso 0.692(13) 1 calc PR B 1
C13B C 0.9343(15) 0.0601(15) 0.1620(6) 0.0386(9) Uani 0.308(13) 1 d PU B 2
H13B H 0.9164 0.1121 0.1420 0.046 Uiso 0.308(13) 1 calc PR B 2
C14B C 0.8856(13) 0.0971(14) 0.1994(4) 0.0404(11) Uani 0.308(13) 1 d PU B 2
H14D H 0.9331 0.1444 0.2124 0.061 Uiso 0.308(13) 1 calc PR B 2
H14E H 0.8718 0.0376 0.2159 0.061 Uiso 0.308(13) 1 calc PR B 2
H14F H 0.8207 0.1330 0.1939 0.061 Uiso 0.308(13) 1 calc PR B 2
C15B C 0.8795(15) -0.0383(12) 0.1517(5) 0.0417(11) Uani 0.308(13) 1 d PU B 2
H15D H 0.8047 -0.0272 0.1527 0.063 Uiso 0.308(13) 1 calc PR B 2
H15E H 0.8988 -0.0927 0.1698 0.063 Uiso 0.308(13) 1 calc PR B 2
H15F H 0.8992 -0.0592 0.1258 0.063 Uiso 0.308(13) 1 calc PR B 2
C16 C 1.2920(3) 0.2189(3) 0.12928(11) 0.0399(7) Uani 1 1 d U . .
H16A H 1.2454 0.2571 0.1114 0.048 Uiso 1 1 calc R . .
C17 C 1.3293(4) 0.2956(4) 0.15952(13) 0.0522(9) Uani 1 1 d U . .
H17A H 1.2699 0.3218 0.1739 0.078 Uiso 1 1 calc R . .
H17B H 1.3648 0.3532 0.1470 0.078 Uiso 1 1 calc R . .
H17C H 1.3770 0.2608 0.1770 0.078 Uiso 1 1 calc R . .
C18 C 1.3835(4) 0.1804(4) 0.10622(14) 0.0545(9) Uani 1 1 d U . .
H18A H 1.3596 0.1314 0.0869 0.082 Uiso 1 1 calc R . .
H18B H 1.4328 0.1461 0.1232 0.082 Uiso 1 1 calc R . .
H18C H 1.4173 0.2390 0.0937 0.082 Uiso 1 1 calc R . .
C21 C 1.0084(4) 0.4499(4) -0.01784(14) 0.0528(9) Uani 1 1 d U . .
H21A H 1.0243 0.3799 -0.0267 0.079 Uiso 1 1 calc R A .
H21B H 1.0714 0.4918 -0.0182 0.079 Uiso 1 1 calc R . .
H21C H 0.9567 0.4809 -0.0347 0.079 Uiso 1 1 calc R . .
C25 C 1.0401(3) 0.3006(3) 0.13573(12) 0.0404(6) Uani 1 1 d U . .
H25A H 1.1023 0.3442 0.1389 0.049 Uiso 1 1 calc R . .
H25B H 1.0075 0.2920 0.1611 0.049 Uiso 1 1 calc R . .
C26 C 0.9673(3) 0.3513(3) 0.10954(11) 0.0407(6) Uani 1 1 d U . .
H26A H 0.9040 0.3720 0.1234 0.049 Uiso 1 1 calc R . .
H26B H 0.9991 0.4139 0.0984 0.049 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_1
_geom_angle_site_symmetry_3
C23 C22 C24 110.3(6) . .
C23 C22 C2 115.6(6) . .
C24 C22 C2 110.5(5) . .
C2 C22B C23B 107.0(9) . .
C2 C22B C24B 116.0(9) . .
C23B C22B C24B 108.7(10) . .
N1 P1 N2 90.60(14) . .
N1 P1 P2 102.79(11) . .
N2 P1 P2 103.04(11) . .
P3 P2 P3 58.05(4) 7_645 .
P3 P2 P1 92.89(5) 7_645 .
P3 P2 P1 92.84(4) . .
P3 P3 P2 61.20(4) 7_645 7_645
P3 P3 P2 60.75(4) 7_645 .
P2 P3 P2 80.27(5) 7_645 .
C25 N1 C7 121.8(3) . .
C25 N1 P1 115.3(2) . .
C7 N1 P1 121.9(2) . .
C1 N2 C26 121.8(3) . .
C1 N2 P1 123.1(2) . .
C26 N2 P1 115.1(2) . .
C6 C1 C2 120.3(3) . .
C6 C1 N2 120.7(3) . .
C2 C1 N2 119.0(3) . .
C3 C2 C1 117.8(4) . .
C3 C2 C22B 115.5(6) . .
C1 C2 C22B 125.2(5) . .
C3 C2 C22 123.1(4) . .
C1 C2 C22 118.4(4) . .
C4 C3 C2 121.3(4) . .
C3 C4 C5 120.7(4) . .
C4 C5 C6 121.0(4) . .
C5 C6 C1 119.0(4) . .
C5 C6 C19 118.7(4) . .
C1 C6 C19 122.4(3) . .
C12 C7 C8 121.7(3) . .
C12 C7 N1 119.6(3) . .
C8 C7 N1 118.7(3) . .
C9 C8 C7 118.1(4) . .
C9 C8 C16 119.4(4) . .
C7 C8 C16 122.5(3) . .
C10 C9 C8 121.4(4) . .
C20 C19 C6 110.3(3) . .
C20 C19 C21 110.6(4) . .
C6 C19 C21 111.6(4) . .
C9 C10 C11 120.3(4) . .
C10 C11 C12 121.0(4) . .
C11 C12 C7 117.4(4) . .
C11 C12 C13A 119.7(5) . .
C7 C12 C13A 122.9(5) . .
C11 C12 C13B 124.7(8) . .
C7 C12 C13B 117.5(8) . .
C12 C13A C15A 113.1(5) . .
C12 C13A C14A 107.4(6) . .
C15A C13A C14A 112.9(7) . .
C15B C13B C14B 106.1(16) . .
C15B C13B C12 113.9(11) . .
C14B C13B C12 115.2(14) . .
C18 C16 C8 113.5(4) . .
C18 C16 C17 109.6(4) . .
C8 C16 C17 110.8(3) . .
N1 C25 C26 110.0(3) . .
N2 C26 C25 107.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C22 C23 1.493(10) .
C22 C24 1.554(10) .
C22 C2 1.603(8) .
C22B C2 1.449(12) .
C22B C23B 1.469(17) .
C22B C24B 1.521(16) .
P1 N1 1.693(3) .
P1 N2 1.693(3) .
P1 P2 2.2894(12) .
P2 P3 2.2182(12) 7_645
P2 P3 2.2277(12) .
P3 P3 2.1571(17) 7_645
P3 P2 2.2183(12) 7_645
N1 C25 1.430(5) .
N1 C7 1.435(4) .
N2 C1 1.429(4) .
N2 C26 1.457(5) .
C1 C6 1.410(5) .
C1 C2 1.417(6) .
C2 C3 1.403(6) .
C3 C4 1.367(6) .
C4 C5 1.371(6) .
C5 C6 1.385(5) .
C6 C19 1.521(6) .
C7 C12 1.406(6) .
C7 C8 1.406(5) .
C8 C9 1.389(5) .
C8 C16 1.519(6) .
C9 C10 1.366(7) .
C19 C20 1.516(6) .
C19 C21 1.529(6) .
C10 C11 1.384(7) .
C11 C12 1.404(6) .
C12 C13A 1.459(9) .
C12 C13B 1.69(2) .
C13A C15A 1.502(11) .
C13A C14A 1.547(11) .
C13B C15B 1.50(3) .
C13B C14B 1.53(2) .
C16 C18 1.519(6) .
C16 C17 1.530(6) .
C25 C26 1.470(5) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.154 0.846 0.250 225 41 ' '
2 -0.154 0.154 0.750 225 41 ' '
3 0.033 0.317 0.164 8 0 ' '
4 0.157 0.157 1.000 43 3 ' '
5 0.346 0.346 0.500 225 41 ' '
6 0.183 0.533 0.914 8 0 ' '
7 0.343 0.657 0.750 43 3 ' '
8 0.316 0.033 0.836 8 0 ' '
9 0.654 0.654 1.000 225 41 ' '
10 0.466 0.817 0.586 8 0 ' '
11 0.533 0.183 0.086 8 0 ' '
12 0.657 0.343 0.250 43 3 ' '
13 0.683 0.967 0.336 8 0 ' '
14 0.843 0.843 0.500 43 3 ' '
15 0.816 0.467 0.414 8 0 ' '
16 0.966 0.683 0.664 8 0 ' '
