#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:57:10 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180457 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/26/7212633.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_7212633
loop_
_publ_author_name
'Ling, Irene'
'Alias, Yatimah'
'Sobolev, Alexandre N.'
'Raston, Colin L.'
_publ_section_title
;
 Hirshfeld surface analysis of phosphonium salts
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4321
_journal_paper_doi               10.1039/c002832k
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C44 H38 P2, 2(C2 N3)'
_chemical_formula_sum            'C48 H38 N6 P2'
_chemical_formula_weight         760.78
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                90.0
_cell_angle_beta                 96.951(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   9.9176(4)
_cell_length_b                   13.7706(6)
_cell_length_c                   14.1618(6)
_cell_measurement_reflns_used    13611
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.49
_cell_measurement_theta_min      3.24
_cell_volume                     1919.88(14)
_computing_cell_refinement
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            55499
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.60
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0395
_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)+(0.0820P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                5191
_reflns_number_total             6772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002832k.txt
_cod_data_source_block           230708c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7212633
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
P1 P 0.20421(3) 0.448641(17) 0.259490(17) 0.01212(7) Uani 1 1 d .
C11 C 0.24131(10) 0.36367(7) 0.35536(7) 0.01453(18) Uani 1 1 d .
C12 C 0.14224(11) 0.29601(7) 0.37401(7) 0.0176(2) Uani 1 1 d .
H12 H 0.0563 0.2954 0.3362 0.021 Uiso 1 1 calc R
C13 C 0.17011(12) 0.22995(7) 0.44789(8) 0.0211(2) Uani 1 1 d .
H13 H 0.1028 0.1845 0.4610 0.025 Uiso 1 1 calc R
C14 C 0.29605(12) 0.23013(8) 0.50264(8) 0.0221(2) Uani 1 1 d .
H14 H 0.3149 0.1846 0.5529 0.027 Uiso 1 1 calc R
C15 C 0.39424(12) 0.29671(9) 0.48403(8) 0.0235(2) Uani 1 1 d .
H15 H 0.4803 0.2964 0.5217 0.028 Uiso 1 1 calc R
C16 C 0.36797(11) 0.36406(8) 0.41065(7) 0.0191(2) Uani 1 1 d .
H16 H 0.4355 0.4098 0.3983 0.023 Uiso 1 1 calc R
C21 C 0.36013(10) 0.49728(7) 0.22817(7) 0.01455(19) Uani 1 1 d .
C22 C 0.42933(11) 0.45039(8) 0.16074(8) 0.0176(2) Uani 1 1 d .
H22 H 0.3916 0.3943 0.1285 0.021 Uiso 1 1 calc R
C23 C 0.55410(11) 0.48680(8) 0.14140(8) 0.0222(2) Uani 1 1 d .
H23 H 0.6011 0.4560 0.0950 0.027 Uiso 1 1 calc R
C24 C 0.61003(11) 0.56783(8) 0.18953(8) 0.0226(2) Uani 1 1 d .
H24 H 0.6952 0.5923 0.1759 0.027 Uiso 1 1 calc R
C25 C 0.54219(11) 0.61346(8) 0.25756(8) 0.0205(2) Uani 1 1 d .
H25 H 0.5816 0.6684 0.2908 0.025 Uiso 1 1 calc R
C26 C 0.41680(10) 0.57884(7) 0.27707(7) 0.0174(2) Uani 1 1 d .
H26 H 0.3700 0.6102 0.3232 0.021 Uiso 1 1 calc R
C31 C 0.09966(10) 0.54525(7) 0.29303(7) 0.01290(18) Uani 1 1 d .
C32 C 0.08772(10) 0.63043(7) 0.23809(7) 0.01596(19) Uani 1 1 d .
H32 H 0.1438 0.6401 0.1891 0.019 Uiso 1 1 calc R
C33 C -0.00670(11) 0.70017(7) 0.25603(7) 0.0176(2) Uani 1 1 d .
H33 H -0.0153 0.7580 0.2192 0.021 Uiso 1 1 calc R
C34 C -0.08880(11) 0.68596(7) 0.32775(7) 0.0184(2) Uani 1 1 d .
H34 H -0.1533 0.7341 0.3395 0.022 Uiso 1 1 calc R
C35 C -0.07708(11) 0.60189(7) 0.38226(8) 0.0184(2) Uani 1 1 d .
H35 H -0.1335 0.5926 0.4311 0.022 Uiso 1 1 calc R
C36 C 0.01724(10) 0.53133(7) 0.36533(7) 0.01546(19) Uani 1 1 d .
H36 H 0.0257 0.4739 0.4027 0.019 Uiso 1 1 calc R
C40 C 0.11280(10) 0.38226(7) 0.16166(7) 0.01374(18) Uani 1 1 d .
H401 H 0.1747 0.3334 0.1390 0.016 Uiso 1 1 calc R
H402 H 0.0369 0.3468 0.1855 0.016 Uiso 1 1 calc R
C41 C 0.05588(10) 0.44448(6) 0.07819(7) 0.01271(18) Uani 1 1 d .
C42 C -0.06639(10) 0.49420(7) 0.08056(7) 0.01463(19) Uani 1 1 d .
H42 H -0.1120 0.4904 0.1357 0.018 Uiso 1 1 calc R
C43 C -0.12233(10) 0.54929(7) 0.00313(7) 0.01426(18) Uani 1 1 d .
H43 H -0.2057 0.5827 0.0056 0.017 Uiso 1 1 calc R
N1 N 0.73311(13) 0.38547(8) 0.40308(8) 0.0361(3) Uani 1 1 d .
C10 C 0.75166(13) 0.32448(9) 0.47446(9) 0.0300(3) Uani 1 1 d .
C20 C 0.78118(11) 0.36316(8) 0.32364(8) 0.0205(2) Uani 1 1 d .
N10 N 0.76177(14) 0.27587(10) 0.54184(8) 0.0451(3) Uani 1 1 d .
N20 N 0.82092(10) 0.35041(7) 0.25082(7) 0.0229(2) Uani 1 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
C31 P1 C21 109.51(4) . .
C31 P1 C11 110.89(5) . .
C21 P1 C11 109.09(5) . .
C31 P1 C40 109.07(5) . .
C21 P1 C40 111.54(5) . .
C11 P1 C40 106.71(5) . .
C16 C11 C12 119.99(9) . .
C16 C11 P1 120.60(8) . .
C12 C11 P1 119.41(8) . .
C13 C12 C11 119.81(10) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C14 C13 C12 120.21(10) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C15 C14 C13 120.03(10) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.65(10) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C15 C16 C11 119.31(10) . .
C15 C16 H16 120.3 . .
C11 C16 H16 120.3 . .
C22 C21 C26 120.44(9) . .
C22 C21 P1 120.42(8) . .
C26 C21 P1 118.98(7) . .
C23 C22 C21 119.27(10) . .
C23 C22 H22 120.4 . .
C21 C22 H22 120.4 . .
C24 C23 C22 120.32(10) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 120.37(10) . .
C23 C24 H24 119.8 . .
C25 C24 H24 119.8 . .
C24 C25 C26 120.14(10) . .
C24 C25 H25 119.9 . .
C26 C25 H25 119.9 . .
C25 C26 C21 119.45(10) . .
C25 C26 H26 120.3 . .
C21 C26 H26 120.3 . .
C36 C31 C32 120.16(9) . .
C36 C31 P1 120.14(7) . .
C32 C31 P1 119.17(7) . .
C33 C32 C31 119.38(9) . .
C33 C32 H32 120.3 . .
C31 C32 H32 120.3 . .
C32 C33 C34 120.31(9) . .
C32 C33 H33 119.8 . .
C34 C33 H33 119.8 . .
C35 C34 C33 120.43(9) . .
C35 C34 H34 119.8 . .
C33 C34 H34 119.8 . .
C34 C35 C36 120.00(10) . .
C34 C35 H35 120.0 . .
C36 C35 H35 120.0 . .
C35 C36 C31 119.72(9) . .
C35 C36 H36 120.1 . .
C31 C36 H36 120.1 . .
C41 C40 P1 114.66(6) . .
C41 C40 H401 108.6 . .
P1 C40 H401 108.6 . .
C41 C40 H402 108.6 . .
P1 C40 H402 108.6 . .
H401 C40 H402 107.6 . .
C42 C41 C43 119.18(9) . 3_565
C42 C41 C40 120.12(9) . .
C43 C41 C40 120.68(9) 3_565 .
C43 C42 C41 120.83(9) . .
C43 C42 H42 119.6 . .
C41 C42 H42 119.6 . .
C42 C43 C41 119.99(9) . 3_565
C42 C43 H43 120.0 . .
C41 C43 H43 120.0 3_565 .
C10 N1 C20 118.72(11) . .
N10 C10 N1 174.19(16) . .
N20 C20 N1 174.80(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C31 1.7860(10) .
P1 C21 1.7895(10) .
P1 C11 1.7963(10) .
P1 C40 1.8092(10) .
C11 C16 1.3975(14) .
C11 C12 1.4022(14) .
C12 C13 1.3888(14) .
C12 H12 0.9500 .
C13 C14 1.3882(16) .
C13 H13 0.9500 .
C14 C15 1.3858(17) .
C14 H14 0.9500 .
C15 C16 1.3938(15) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.3994(14) .
C21 C26 1.4010(14) .
C22 C23 1.3926(15) .
C22 H22 0.9500 .
C23 C24 1.3878(16) .
C23 H23 0.9500 .
C24 C25 1.3903(16) .
C24 H24 0.9500 .
C25 C26 1.3904(15) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C36 1.3985(14) .
C31 C32 1.4045(13) .
C32 C33 1.3862(14) .
C32 H32 0.9500 .
C33 C34 1.3903(14) .
C33 H33 0.9500 .
C34 C35 1.3885(14) .
C34 H34 0.9500 .
C35 C36 1.3896(14) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C40 C41 1.5128(13) .
C40 H401 0.9900 .
C40 H402 0.9900 .
C41 C42 1.3965(14) .
C41 C43 1.3969(14) 3_565
C42 C43 1.3924(13) .
C42 H42 0.9500 .
C43 C41 1.3969(14) 3_565
C43 H43 0.9500 .
N1 C10 1.3100(17) .
N1 C20 1.3104(16) .
C10 N10 1.1600(17) .
C20 N20 1.1611(15) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C31 P1 C11 C16 -102.79(9) . .
C21 P1 C11 C16 17.90(10) . .
C40 P1 C11 C16 138.54(8) . .
C31 P1 C11 C12 77.73(9) . .
C21 P1 C11 C12 -161.58(8) . .
C40 P1 C11 C12 -40.94(9) . .
C16 C11 C12 C13 0.42(15) . .
P1 C11 C12 C13 179.90(8) . .
C11 C12 C13 C14 -0.61(16) . .
C12 C13 C14 C15 0.36(16) . .
C13 C14 C15 C16 0.10(16) . .
C14 C15 C16 C11 -0.29(16) . .
C12 C11 C16 C15 0.03(15) . .
P1 C11 C16 C15 -179.45(8) . .
C31 P1 C21 C22 -150.08(8) . .
C11 P1 C21 C22 88.39(9) . .
C40 P1 C21 C22 -29.24(10) . .
C31 P1 C21 C26 34.52(9) . .
C11 P1 C21 C26 -87.01(9) . .
C40 P1 C21 C26 155.36(8) . .
C26 C21 C22 C23 -1.23(16) . .
P1 C21 C22 C23 -176.55(8) . .
C21 C22 C23 C24 0.95(17) . .
C22 C23 C24 C25 0.04(18) . .
C23 C24 C25 C26 -0.77(17) . .
C24 C25 C26 C21 0.50(16) . .
C22 C21 C26 C25 0.51(15) . .
P1 C21 C26 C25 175.90(8) . .
C21 P1 C31 C36 -144.58(8) . .
C11 P1 C31 C36 -24.13(10) . .
C40 P1 C31 C36 93.10(9) . .
C21 P1 C31 C32 43.68(9) . .
C11 P1 C31 C32 164.12(8) . .
C40 P1 C31 C32 -78.65(9) . .
C36 C31 C32 C33 -0.22(15) . .
P1 C31 C32 C33 171.52(8) . .
C31 C32 C33 C34 0.01(15) . .
C32 C33 C34 C35 0.09(16) . .
C33 C34 C35 C36 0.04(16) . .
C34 C35 C36 C31 -0.26(15) . .
C32 C31 C36 C35 0.35(15) . .
P1 C31 C36 C35 -171.31(8) . .
C31 P1 C40 C41 52.39(8) . .
C21 P1 C40 C41 -68.70(8) . .
C11 P1 C40 C41 172.24(7) . .
P1 C40 C41 C42 -81.26(10) . .
P1 C40 C41 C43 100.67(9) . 3_565
C43 C41 C42 C43 0.14(15) 3_565 .
C40 C41 C42 C43 -177.95(9) . .
C41 C42 C43 C41 -0.14(15) . 3_565
