data_2013177
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o46
_journal_page_last  o50
_publ_section_title
;
Two derivatives of (N-phenylthioureidoalkyl)phosphonates
;
loop_
_publ_author_name
  "Ch\;eci\'nska, Lilianna"
  "Siero\'n, Les\/law"
  "Bukowska-Strzy\.zewska, Maria"
  'Kudzin, Zbigniew H.'
  "F\'abi\'an, L\'aszl\'o"
_chemical_formula_moiety  'C24 H27 N2 O3 P S'
_chemical_formula_sum  'C24 H27 N2 O3 P S'
_chemical_formula_weight  454.51
_symmetry_cell_setting  'Triclinic'
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  10.1931(7)
_cell_length_b  10.5503(5)
_cell_length_c  11.9560(7)
_cell_angle_alpha  90.932(4)
_cell_angle_beta  103.252(5)
_cell_angle_gamma  101.923(5)
_cell_volume  1221.78(12)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.235
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S1 0.40957(7) 0.34031(7) 0.15910(6) 0.0691(3) Uani d . 1 . . S
  N1 0.1853(2) 0.2333(2) 0.23068(18) 0.0670(6) Uani d D 1 . . N
  H1 0.104(2) 0.188(3) 0.216(2) 0.075(9) Uiso d D 1 . . H
  N2 0.1648(2) 0.2042(2) 0.04012(18) 0.0583(6) Uani d D 1 . . N
  H2 0.0881(19) 0.162(2) 0.041(2) 0.055(8) Uiso d D 1 . . H
  C1 0.2469(3) 0.2564(2) 0.1424(2) 0.0532(6) Uani d . 1 . . C
  C2 0.2049(3) 0.2064(2) -0.0692(2) 0.0569(6) Uani d . 1 . . C
  H201 0.3006 0.2551 -0.0561 0.068 Uiso calc R 1 . . H
  C3 0.1140(4) 0.2728(3) -0.1606(2) 0.0823(9) Uani d D 1 . . C
  H301 0.1323 0.2559 -0.2349 0.099 Uiso calc R 1 . . H
  H302 0.0179 0.2337 -0.1652 0.099 Uiso calc R 1 . . H
  C4 0.1357(4) 0.4173(3) -0.1378(3) 0.0893(10) Uani d D 1 . . C
  H4A 0.1340 0.4363 -0.0577 0.107 Uiso calc PR 0.673(9) A 1 H
  H4B 0.2323 0.4396 -0.0944 0.107 Uiso calc PR 0.327(9) A 2 H
  C5A 0.2714(6) 0.4818(6) -0.1570(7) 0.124(3) Uani d PD 0.673(9) A 1 C
  H51A 0.3435 0.4539 -0.1030 0.186 Uiso calc PR 0.673(9) A 1 H
  H52A 0.2832 0.5742 -0.1465 0.186 Uiso calc PR 0.673(9) A 1 H
  H53A 0.2757 0.4591 -0.2340 0.186 Uiso calc PR 0.673(9) A 1 H
  C6A 0.0229(9) 0.4681(7) -0.2171(10) 0.162(5) Uani d PD 0.673(9) A 1 C
  H61A 0.0356 0.4656 -0.2942 0.243 Uiso calc PR 0.673(9) A 1 H
  H62A 0.0267 0.5560 -0.1921 0.243 Uiso calc PR 0.673(9) A 1 H
  H63A -0.0652 0.4151 -0.2156 0.243 Uiso calc PR 0.673(9) A 1 H
  C5B 0.0634(15) 0.4564(13) -0.0517(10) 0.128(6) Uani d PD 0.327(9) A 2 C
  H51B 0.0769 0.5492 -0.0456 0.192 Uiso calc PR 0.327(9) A 2 H
  H52B 0.1004 0.4266 0.0219 0.192 Uiso calc PR 0.327(9) A 2 H
  H53B -0.0335 0.4184 -0.0761 0.192 Uiso calc PR 0.327(9) A 2 H
  C6B 0.138(3) 0.5051(17) -0.2351(14) 0.160(9) Uani d PD 0.327(9) A 2 C
  H61B 0.2233 0.5111 -0.2585 0.240 Uiso calc PR 0.327(9) A 2 H
  H62B 0.1314 0.5899 -0.2101 0.240 Uiso calc PR 0.327(9) A 2 H
  H63B 0.0620 0.4705 -0.2988 0.240 Uiso calc PR 0.327(9) A 2 H
  P1 0.19924(7) 0.04026(6) -0.11142(6) 0.0588(2) Uani d . 1 . . P
  O1 0.06818(18) -0.05100(17) -0.11522(14) 0.0649(5) Uani d . 1 . . O
  O2 0.2416(2) 0.05432(18) -0.23047(16) 0.0754(6) Uani d . 1 . . O
  O3 0.32753(18) 0.00418(18) -0.02859(17) 0.0726(5) Uani d . 1 . . O
  C11 0.2499(3) 0.2707(2) 0.3481(2) 0.0607(7) Uani d D 1 . . C
  C12 0.2947(4) 0.1816(3) 0.4226(2) 0.0909(10) Uani d D 1 . . C
  H12 0.2841 0.0964 0.3947 0.109 Uiso calc R 1 . . H
  C13 0.3550(4) 0.2162(4) 0.5380(2) 0.1065(12) Uani d D 1 . . C
  H13 0.3869 0.1554 0.5865 0.128 Uiso calc R 1 . . H
  C14 0.3675(4) 0.3414(4) 0.5805(3) 0.1124(14) Uani d D 1 . . C
  H14 0.4038 0.3646 0.6586 0.135 Uiso calc R 1 . . H
  C15 0.3258(5) 0.4320(4) 0.5063(3) 0.1404(19) Uani d D 1 . . C
  H15 0.3378 0.5175 0.5341 0.168 Uiso calc R 1 . . H
  C16 0.2661(4) 0.3967(3) 0.3909(3) 0.1114(13) Uani d D 1 . . C
  H16 0.2369 0.4582 0.3420 0.134 Uiso calc R 1 . . H
  C21 0.2224(3) -0.0536(3) -0.3081(2) 0.0664(7) Uani d . 1 . . C
  C22 0.0978(3) -0.0934(3) -0.3854(3) 0.0823(9) Uani d . 1 . . C
  H22 0.0254 -0.0525 -0.3845 0.099 Uiso calc R 1 . . H
  C23 0.0814(4) -0.1946(4) -0.4642(3) 0.1017(12) Uani d . 1 . . C
  H23 -0.0026 -0.2226 -0.5174 0.122 Uiso calc R 1 . . H
  C24 0.1882(5) -0.2548(4) -0.4652(3) 0.1123(13) Uani d . 1 . . C
  H24 0.1767 -0.3230 -0.5193 0.135 Uiso calc R 1 . . H
  C25 0.3110(5) -0.2147(4) -0.3870(3) 0.1094(13) Uani d . 1 . . C
  H25 0.3831 -0.2558 -0.3881 0.131 Uiso calc R 1 . . H
  C26 0.3296(4) -0.1137(4) -0.3063(3) 0.0891(10) Uani d . 1 . . C
  H26 0.4129 -0.0871 -0.2520 0.107 Uiso calc R 1 . . H
  C31 0.3264(3) -0.0937(3) 0.0504(3) 0.0639(7) Uani d . 1 . . C
  C32 0.3693(3) -0.2013(3) 0.0254(3) 0.0908(10) Uani d . 1 . . C
  H32 0.3936 -0.2123 -0.0439 0.109 Uiso calc R 1 . . H
  C33 0.3764(4) -0.2951(4) 0.1053(5) 0.1152(14) Uani d . 1 . . C
  H33 0.4049 -0.3703 0.0894 0.138 Uiso calc R 1 . . H
  C34 0.3418(4) -0.2772(5) 0.2067(5) 0.1202(16) Uani d . 1 . . C
  H34 0.3469 -0.3398 0.2604 0.144 Uiso calc R 1 . . H
  C35 0.2997(5) -0.1674(5) 0.2294(4) 0.1234(14) Uani d . 1 . . C
  H35 0.2761 -0.1556 0.2989 0.148 Uiso calc R 1 . . H
  C36 0.2913(4) -0.0738(3) 0.1514(3) 0.0977(11) Uani d . 1 . . C
  H36 0.2625 0.0012 0.1671 0.117 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S1 0.0571(5) 0.0725(5) 0.0688(5) -0.0001(3) 0.0102(3) -0.0038(4)
  N1 0.0579(15) 0.0792(16) 0.0529(13) -0.0058(12) 0.0103(11) -0.0062(11)
  N2 0.0517(14) 0.0622(13) 0.0551(13) 0.0007(11) 0.0114(11) -0.0021(10)
  C1 0.0568(15) 0.0497(13) 0.0500(14) 0.0095(11) 0.0086(12) 0.0004(11)
  C2 0.0601(16) 0.0578(14) 0.0490(14) 0.0043(12) 0.0129(12) 0.0004(11)
  C3 0.109(3) 0.076(2) 0.0605(18) 0.0273(18) 0.0108(17) 0.0082(15)
  C4 0.113(3) 0.076(2) 0.088(2) 0.031(2) 0.030(2) 0.0174(17)
  C5A 0.121(6) 0.089(4) 0.157(6) 0.006(4) 0.041(5) 0.012(4)
  C6A 0.134(7) 0.094(5) 0.229(11) 0.035(5) -0.029(7) 0.055(5)
  C5B 0.176(14) 0.105(9) 0.126(11) 0.046(9) 0.069(10) -0.004(8)
  C6B 0.20(3) 0.139(14) 0.175(17) 0.053(15) 0.091(17) 0.075(12)
  P1 0.0605(5) 0.0578(4) 0.0557(4) 0.0018(3) 0.0188(3) 0.0000(3)
  O1 0.0623(11) 0.0679(11) 0.0578(11) -0.0037(9) 0.0173(8) -0.0045(8)
  O2 0.0968(15) 0.0654(11) 0.0671(12) 0.0027(10) 0.0395(11) -0.0026(9)
  O3 0.0570(11) 0.0684(12) 0.0908(14) 0.0075(9) 0.0185(10) 0.0182(10)
  C11 0.0593(16) 0.0668(16) 0.0517(15) 0.0075(13) 0.0101(12) 0.0011(13)
  C12 0.107(3) 0.076(2) 0.083(2) 0.0188(18) 0.0098(19) 0.0111(17)
  C13 0.117(3) 0.128(3) 0.067(2) 0.026(2) 0.006(2) 0.031(2)
  C14 0.097(3) 0.179(4) 0.058(2) 0.044(3) 0.0011(18) -0.014(3)
  C15 0.181(5) 0.133(4) 0.092(3) 0.070(3) -0.027(3) -0.049(3)
  C16 0.155(4) 0.089(2) 0.079(2) 0.050(2) -0.014(2) -0.0118(19)
  C21 0.074(2) 0.0712(17) 0.0564(16) 0.0130(15) 0.0241(14) 0.0015(13)
  C22 0.079(2) 0.105(2) 0.0640(18) 0.0304(18) 0.0104(16) 0.0013(17)
  C23 0.097(3) 0.126(3) 0.069(2) 0.021(2) -0.0018(19) -0.015(2)
  C24 0.142(4) 0.111(3) 0.081(3) 0.038(3) 0.015(3) -0.026(2)
  C25 0.119(3) 0.118(3) 0.099(3) 0.052(3) 0.020(2) -0.023(2)
  C26 0.076(2) 0.110(3) 0.080(2) 0.024(2) 0.0114(17) -0.0103(19)
  C31 0.0473(15) 0.0585(16) 0.080(2) 0.0058(12) 0.0081(13) 0.0077(14)
  C32 0.090(2) 0.068(2) 0.116(3) 0.0187(18) 0.025(2) 0.003(2)
  C33 0.094(3) 0.073(2) 0.172(5) 0.024(2) 0.012(3) 0.027(3)
  C34 0.089(3) 0.104(3) 0.147(4) 0.012(2) -0.008(3) 0.062(3)
  C35 0.149(4) 0.130(4) 0.100(3) 0.040(3) 0.035(3) 0.041(3)
  C36 0.130(3) 0.081(2) 0.096(3) 0.039(2) 0.039(2) 0.024(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 C1 . 1.676(3) yes
  N1 C1 . 1.348(3) yes
  N1 C11 . 1.418(3) yes
  N1 H1 . 0.843(17) no
  N2 C1 . 1.348(3) yes
  N2 C2 . 1.455(3) yes
  N2 H2 . 0.817(16) no
  C2 C3 . 1.541(4) no
  C2 P1 . 1.802(3) yes
  C2 H201 . 0.9800 no
  C3 C4 . 1.505(3) no
  C3 H301 . 0.9700 no
  C3 H302 . 0.9700 no
  C4 C5A . 1.480(4) no
  C4 C5B . 1.495(5) no
  C4 C6B . 1.499(5) no
  C4 C6A . 1.510(4) no
  C4 H4A . 0.9800 no
  C4 H4B . 0.9800 no
  C5A H51A . 0.9600 no
  C5A H52A . 0.9600 no
  C5A H53A . 0.9600 no
  C6A H61A . 0.9600 no
  C6A H62A . 0.9600 no
  C6A H63A . 0.9600 no
  C5B H51B . 0.9600 no
  C5B H52B . 0.9600 no
  C5B H53B . 0.9600 no
  C6B H61B . 0.9600 no
  C6B H62B . 0.9600 no
  C6B H63B . 0.9600 no
  P1 O1 . 1.4673(18) yes
  P1 O3 . 1.568(2) yes
  P1 O2 . 1.5800(19) yes
  O2 C21 . 1.409(3) no
  O3 C31 . 1.411(3) no
  C11 C12 . 1.380(4) no
  C11 C16 . 1.381(4) no
  C12 C13 . 1.3844(19) no
  C12 H12 . 0.9300 no
  C13 C14 . 1.378(6) no
  C13 H13 . 0.9300 no
  C14 C15 . 1.381(6) no
  C14 H14 . 0.9300 no
  C15 C16 . 1.384(5) no
  C15 H15 . 0.9300 no
  C16 H16 . 0.9300 no
  C21 C26 . 1.368(4) no
  C21 C22 . 1.369(4) no
  C22 C23 . 1.370(5) no
  C22 H22 . 0.9300 no
  C23 C24 . 1.371(5) no
  C23 H23 . 0.9300 no
  C24 C25 . 1.360(5) no
  C24 H24 . 0.9300 no
  C25 C26 . 1.379(5) no
  C25 H25 . 0.9300 no
  C26 H26 . 0.9300 no
  C31 C32 . 1.350(4) no
  C31 C36 . 1.360(4) no
  C32 C33 . 1.387(6) no
  C32 H32 . 0.9300 no
  C33 C34 . 1.359(6) no
  C33 H33 . 0.9300 no
  C34 C35 . 1.359(6) no
  C34 H34 . 0.9300 no
  C35 C36 . 1.371(5) no
  C35 H35 . 0.9300 no
  C36 H36 . 0.9300 no