#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/85/1508509.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_1508509
loop_
_publ_author_name
'Marc, Philippe'
'Custelcean, Radu'
'Groenewold, Gary S.'
'Klaehn, John R.'
'Peterman, Dean R.'
'Delmau, Lætitia H.'
_publ_section_title
;
 Degradation of CYANEX 301 in Contact with Nitric Acid Media
;
_journal_issue                   40
_journal_name_full
'Industrial & Engineering Chemistry Research'
_journal_page_first              13238
_journal_paper_doi               10.1021/ie300757r
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C16 H35 P S2'
_chemical_formula_weight         322.53
_chemical_name_common            Cyanex-301
_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                75.089(2)
_cell_angle_beta                 82.148(2)
_cell_angle_gamma                89.399(2)
_cell_formula_units_Z            4
_cell_length_a                   11.8398(12)
_cell_length_b                   12.0290(12)
_cell_length_c                   14.8387(15)
_cell_measurement_temperature    173(2)
_cell_volume                     2022.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25477
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.981
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         10021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0552
_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)+(0.0918P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1536
_reflns_number_gt                7127
_reflns_number_total             10021
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ie300757r_si_003.cif
_cod_data_source_block           c:\frames\383\work\383s
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508509
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
S1 S 0.83187(4) 0.18070(5) 0.03219(4) 0.02894(14) Uani 1 1 d .
P1 P 0.68014(4) 0.23964(5) 0.01176(4) 0.02230(13) Uani 1 1 d .
C1 C 0.66350(17) 0.29897(19) -0.11153(15) 0.0278(5) Uani 1 1 d .
H1A H 0.6484 0.2343 -0.1385 0.033 Uiso 1 1 calc R
H1B H 0.5951 0.3472 -0.1142 0.033 Uiso 1 1 calc R
H1S H 0.4806(19) 0.1663(19) 0.0325(16) 0.029(6) Uiso 1 1 d .
S2 S 0.56325(5) 0.10098(5) 0.06014(4) 0.03226(15) Uani 1 1 d .
P2 P 0.18467(4) 0.25916(5) -0.01114(4) 0.02472(14) Uani 1 1 d .
C2 C 0.76455(18) 0.3720(2) -0.17508(15) 0.0300(5) Uani 1 1 d .
H2 H 0.8318 0.3212 -0.1768 0.036 Uiso 1 1 calc R
H2S H -0.009(2) 0.330(2) -0.0297(17) 0.040(7) Uiso 1 1 d .
S3 S 0.34243(4) 0.31741(5) -0.03214(4) 0.03082(15) Uani 1 1 d .
C3 C 0.7341(2) 0.4142(2) -0.27679(16) 0.0360(5) Uani 1 1 d .
H3 H 0.6608 0.3766 -0.2788 0.043 Uiso 1 1 calc R
H3A H 0.7215 0.4980 -0.2898 0.043 Uiso 1 1 calc R
S4 S 0.08180(5) 0.39930(5) -0.05603(5) 0.03667(16) Uani 1 1 d .
C4 C 0.8216(2) 0.3928(2) -0.35683(17) 0.0364(5) Uani 1 1 d .
C5 C 0.8262(3) 0.2636(2) -0.3500(2) 0.0505(7) Uani 1 1 d .
H5A H 0.8804 0.2504 -0.4021 0.076 Uiso 1 1 calc R
H5B H 0.7503 0.2346 -0.3535 0.076 Uiso 1 1 calc R
H5C H 0.8509 0.2231 -0.2900 0.076 Uiso 1 1 calc R
C6 C 0.79767(19) 0.4732(2) -0.13870(17) 0.0346(5) Uani 1 1 d .
H6A H 0.7313 0.5213 -0.1322 0.052 Uiso 1 1 calc R
H6B H 0.8591 0.5190 -0.1833 0.052 Uiso 1 1 calc R
H6C H 0.8238 0.4441 -0.0773 0.052 Uiso 1 1 calc R
C7 C 0.9400(2) 0.4392(3) -0.3547(2) 0.0523(7) Uani 1 1 d .
H7B H 0.9932 0.4231 -0.4062 0.078 Uiso 1 1 calc R
H7A H 0.9657 0.4019 -0.2944 0.078 Uiso 1 1 calc R
H7C H 0.9373 0.5225 -0.3622 0.078 Uiso 1 1 calc R
C8 C 0.7796(3) 0.4537(3) -0.45006(18) 0.0544(8) Uani 1 1 d .
H8B H 0.7779 0.5368 -0.4563 0.082 Uiso 1 1 calc R
H8A H 0.7027 0.4248 -0.4507 0.082 Uiso 1 1 calc R
H8C H 0.8314 0.4384 -0.5027 0.082 Uiso 1 1 calc R
C9 C 0.62365(17) 0.34724(18) 0.07114(15) 0.0258(4) Uani 1 1 d .
H9A H 0.6737 0.4169 0.0471 0.031 Uiso 1 1 calc R
H9B H 0.5477 0.3684 0.0522 0.031 Uiso 1 1 calc R
C10 C 0.61079(18) 0.31598(19) 0.17904(16) 0.0291(5) Uani 1 1 d .
H10 H 0.5892 0.2324 0.2039 0.035 Uiso 1 1 calc R
C11 C 0.72340(19) 0.3387(2) 0.21322(16) 0.0320(5) Uani 1 1 d .
H11A H 0.7867 0.3304 0.1646 0.038 Uiso 1 1 calc R
H11B H 0.7248 0.4200 0.2160 0.038 Uiso 1 1 calc R
C12 C 0.7496(2) 0.2640(2) 0.30857(19) 0.0457(7) Uani 1 1 d .
C13 C 0.6577(3) 0.2687(3) 0.3904(2) 0.0635(9) Uani 1 1 d .
H13C H 0.6473 0.3488 0.3930 0.095 Uiso 1 1 calc R
H13A H 0.6811 0.2236 0.4496 0.095 Uiso 1 1 calc R
H13B H 0.5857 0.2366 0.3811 0.095 Uiso 1 1 calc R
C14 C 0.5133(2) 0.3874(3) 0.21262(19) 0.0446(6) Uani 1 1 d .
H14A H 0.5326 0.4695 0.1869 0.067 Uiso 1 1 calc R
H14C H 0.5021 0.3690 0.2816 0.067 Uiso 1 1 calc R
H14B H 0.4430 0.3691 0.1908 0.067 Uiso 1 1 calc R
C15 C 0.7657(4) 0.1391(3) 0.3031(3) 0.0837(13) Uani 1 1 d .
H15A H 0.6916 0.1043 0.3020 0.126 Uiso 1 1 calc R
H15C H 0.7988 0.0956 0.3582 0.126 Uiso 1 1 calc R
H15B H 0.8169 0.1378 0.2457 0.126 Uiso 1 1 calc R
C16 C 0.8621(3) 0.3110(4) 0.3264(2) 0.0716(10) Uani 1 1 d .
H16A H 0.9218 0.3097 0.2740 0.107 Uiso 1 1 calc R
H16B H 0.8841 0.2630 0.3851 0.107 Uiso 1 1 calc R
H16C H 0.8522 0.3902 0.3315 0.107 Uiso 1 1 calc R
C17 C 0.14868(18) 0.15487(19) -0.07274(16) 0.0305(5) Uani 1 1 d .
H17A H 0.1906 0.0839 -0.0497 0.037 Uiso 1 1 calc R
H17B H 0.0663 0.1352 -0.0546 0.037 Uiso 1 1 calc R
C18 C 0.17318(19) 0.1897(2) -0.18082(17) 0.0319(5) Uani 1 1 d .
H18 H 0.1616 0.2742 -0.2040 0.038 Uiso 1 1 calc R
C19 C 0.29665(19) 0.1630(2) -0.21439(16) 0.0325(5) Uani 1 1 d .
H19A H 0.2978 0.0813 -0.2162 0.039 Uiso 1 1 calc R
H19B H 0.3434 0.1702 -0.1657 0.039 Uiso 1 1 calc R
C20 C 0.3571(2) 0.2346(2) -0.31008(18) 0.0419(6) Uani 1 1 d .
C21 C 0.2965(3) 0.2256(3) -0.3925(2) 0.0689(10) Uani 1 1 d .
H21A H 0.2206 0.2585 -0.3861 0.103 Uiso 1 1 calc R
H21B H 0.2888 0.1446 -0.3925 0.103 Uiso 1 1 calc R
H21C H 0.3410 0.2681 -0.4518 0.103 Uiso 1 1 calc R
C22 C 0.0860(2) 0.1237(3) -0.2170(2) 0.0524(7) Uani 1 1 d .
H22A H 0.0980 0.1451 -0.2860 0.079 Uiso 1 1 calc R
H22C H 0.0086 0.1433 -0.1944 0.079 Uiso 1 1 calc R
H22B H 0.0960 0.0408 -0.1937 0.079 Uiso 1 1 calc R
C23 C 0.3673(3) 0.3606(3) -0.3101(3) 0.0724(10) Uani 1 1 d .
H23C H 0.4138 0.4030 -0.3683 0.109 Uiso 1 1 calc R
H23A H 0.4035 0.3667 -0.2559 0.109 Uiso 1 1 calc R
H23B H 0.2912 0.3932 -0.3059 0.109 Uiso 1 1 calc R
C24 C 0.4765(3) 0.1864(3) -0.3238(2) 0.0697(10) Uani 1 1 d .
H24A H 0.4702 0.1061 -0.3264 0.105 Uiso 1 1 calc R
H24B H 0.5166 0.1902 -0.2711 0.105 Uiso 1 1 calc R
H24C H 0.5193 0.2319 -0.3828 0.105 Uiso 1 1 calc R
C25 C 0.12918(18) 0.1975(2) 0.11249(16) 0.0320(5) Uani 1 1 d .
H25A H 0.1048 0.2614 0.1408 0.038 Uiso 1 1 calc R
H25B H 0.0603 0.1501 0.1154 0.038 Uiso 1 1 calc R
C26 C 0.21071(19) 0.1229(2) 0.17380(16) 0.0327(5) Uani 1 1 d .
H26 H 0.2786 0.1720 0.1731 0.039 Uiso 1 1 calc R
C27 C 0.1505(2) 0.0834(2) 0.27658(17) 0.0398(6) Uani 1 1 d .
H27A H 0.0742 0.1179 0.2795 0.048 Uiso 1 1 calc R
H27B H 0.1387 -0.0011 0.2930 0.048 Uiso 1 1 calc R
C28 C 0.2129(2) 0.1138(2) 0.35235(18) 0.0377(6) Uani 1 1 d .
C29 C 0.1423(3) 0.0612(3) 0.44806(19) 0.0587(8) Uani 1 1 d .
H29B H 0.1369 -0.0225 0.4587 0.088 Uiso 1 1 calc R
H29A H 0.0656 0.0927 0.4489 0.088 Uiso 1 1 calc R
H29C H 0.1791 0.0798 0.4978 0.088 Uiso 1 1 calc R
C30 C 0.2527(2) 0.0202(2) 0.13758(18) 0.0392(6) Uani 1 1 d .
H30B H 0.1872 -0.0266 0.1337 0.059 Uiso 1 1 calc R
H30C H 0.3010 -0.0264 0.1808 0.059 Uiso 1 1 calc R
H30A H 0.2970 0.0476 0.0749 0.059 Uiso 1 1 calc R
C31 C 0.3313(2) 0.0654(3) 0.3518(2) 0.0607(9) Uani 1 1 d .
H31A H 0.3762 0.0969 0.2899 0.091 Uiso 1 1 calc R
H31B H 0.3260 -0.0186 0.3649 0.091 Uiso 1 1 calc R
H31C H 0.3686 0.0866 0.4003 0.091 Uiso 1 1 calc R
C32 C 0.2185(3) 0.2434(2) 0.3374(2) 0.0535(7) Uani 1 1 d .
H32B H 0.2606 0.2621 0.3843 0.080 Uiso 1 1 calc R
H32A H 0.1411 0.2724 0.3442 0.080 Uiso 1 1 calc R
H32C H 0.2577 0.2792 0.2741 0.080 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'
S S 0.1246 0.1234 '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
C9 P1 C1 105.19(10)
C9 P1 S1 118.41(7)
C1 P1 S1 114.30(7)
C9 P1 S2 104.91(7)
C1 P1 S2 105.13(7)
S1 P1 S2 107.76(3)
C2 C1 P1 116.71(14)
C17 P2 C25 105.72(11)
C17 P2 S3 118.51(8)
C25 P2 S3 113.98(8)
C17 P2 S4 104.79(8)
C25 P2 S4 105.15(8)
S3 P2 S4 107.57(3)
C6 C2 C1 112.77(19)
C6 C2 C3 110.96(19)
C1 C2 C3 108.90(18)
C4 C3 C2 116.9(2)
C7 C4 C5 109.8(2)
C7 C4 C8 109.6(2)
C5 C4 C8 108.4(2)
C7 C4 C3 112.0(2)
C5 C4 C3 109.7(2)
C8 C4 C3 107.2(2)
C10 C9 P1 118.01(15)
C9 C10 C14 107.20(19)
C9 C10 C11 110.95(17)
C14 C10 C11 112.0(2)
C12 C11 C10 118.6(2)
C13 C12 C15 110.0(3)
C13 C12 C16 108.4(2)
C15 C12 C16 108.8(3)
C13 C12 C11 113.1(2)
C15 C12 C11 109.7(2)
C16 C12 C11 106.8(2)
C18 C17 P2 117.45(16)
C17 C18 C19 110.64(18)
C17 C18 C22 107.1(2)
C19 C18 C22 111.9(2)
C18 C19 C20 119.4(2)
C23 C20 C21 109.1(3)
C23 C20 C24 109.3(3)
C21 C20 C24 108.2(3)
C23 C20 C19 110.6(2)
C21 C20 C19 112.8(2)
C24 C20 C19 106.8(2)
C26 C25 P2 116.72(15)
C30 C26 C25 112.8(2)
C30 C26 C27 111.0(2)
C25 C26 C27 109.02(19)
C28 C27 C26 116.3(2)
C31 C28 C32 110.4(2)
C31 C28 C29 109.1(2)
C32 C28 C29 108.3(2)
C31 C28 C27 111.6(2)
C32 C28 C27 109.9(2)
C29 C28 C27 107.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 P1 1.9578(7)
P1 C9 1.818(2)
P1 C1 1.822(2)
P1 S2 2.0913(7)
C1 C2 1.542(3)
P2 C17 1.816(2)
P2 C25 1.824(2)
P2 S3 1.9579(7)
P2 S4 2.0903(8)
C2 C6 1.527(3)
C2 C3 1.554(3)
C3 C4 1.539(3)
C4 C7 1.521(4)
C4 C5 1.532(4)
C4 C8 1.535(4)
C9 C10 1.534(3)
C10 C14 1.536(3)
C10 C11 1.541(3)
C11 C12 1.538(3)
C12 C13 1.528(4)
C12 C15 1.533(4)
C12 C16 1.534(4)
C17 C18 1.537(3)
C18 C19 1.537(3)
C18 C22 1.540(3)
C19 C20 1.541(3)
C20 C23 1.522(4)
C20 C21 1.527(4)
C20 C24 1.531(4)
C25 C26 1.539(3)
C26 C30 1.522(3)
C26 C27 1.548(3)
C27 C28 1.545(3)
C28 C31 1.513(4)
C28 C32 1.517(4)
C28 C29 1.530(4)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 143644 ChemSpider
