data_2013178
_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  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  9.9402(4)
_cell_length_b  16.7505(6)
_cell_length_c  14.1979(5)
_cell_angle_alpha  90
_cell_angle_beta  91.973(3)
_cell_angle_gamma  90
_cell_volume  2362.60(15)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.278
_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 0.41733(9) 0.33503(4) 0.22394(5) 0.0764(3) Uani d . 1 . . S
  C1 0.4009(2) 0.41162(13) 0.29735(15) 0.0475(5) Uani d . 1 . . C
  N1 0.3649(2) 0.48546(12) 0.26852(14) 0.0552(5) Uani d D 1 . . N
  H1 0.361(2) 0.5208(13) 0.3087(16) 0.055(7) Uiso d D 1 . . H
  N2 0.42313(19) 0.40706(11) 0.39175(13) 0.0495(5) Uani d D 1 . . N
  H2 0.410(2) 0.4484(12) 0.4229(15) 0.046(6) Uiso d D 1 . . H
  C2 0.4646(2) 0.33567(13) 0.44276(15) 0.0475(5) Uani d . 1 . . C
  H201 0.4751 0.2932 0.3962 0.057 Uiso calc R 1 . . H
  C3 0.3601(2) 0.30688(15) 0.51237(18) 0.0618(7) Uani d . 1 . . C
  H301 0.4006 0.2621 0.5475 0.074 Uiso calc R 1 . . H
  C4 0.3240(3) 0.37063(19) 0.5847(2) 0.0861(9) Uani d . 1 . . C
  H401 0.2638 0.3482 0.6291 0.129 Uiso calc R 1 . . H
  H402 0.2810 0.4149 0.5529 0.129 Uiso calc R 1 . . H
  H403 0.4044 0.3887 0.6175 0.129 Uiso calc R 1 . . H
  C5 0.2356(3) 0.27521(19) 0.4608(3) 0.0914(10) Uani d . 1 . . C
  H501 0.1630 0.2727 0.5046 0.110 Uiso calc R 1 . . H
  H502 0.2092 0.3128 0.4115 0.110 Uiso calc R 1 . . H
  C6 0.2515(4) 0.1946(2) 0.4173(4) 0.1354(17) Uani d . 1 . . C
  H601 0.2826 0.1574 0.4647 0.203 Uiso calc R 1 . . H
  H602 0.3158 0.1976 0.3685 0.203 Uiso calc R 1 . . H
  H603 0.1664 0.1771 0.3909 0.203 Uiso calc R 1 . . H
  P1 0.62958(6) 0.35621(3) 0.49463(4) 0.04534(19) Uani d . 1 . . P
  O1 0.64574(15) 0.43137(8) 0.54679(10) 0.0505(4) Uani d . 1 . . O
  O2 0.65682(16) 0.27821(9) 0.55433(12) 0.0605(5) Uani d D 1 . . O
  O3 0.72806(18) 0.34712(10) 0.41148(13) 0.0674(5) Uani d . 1 . . O
  C11 0.3427(3) 0.50966(14) 0.17258(16) 0.0538(6) Uani d . 1 . . C
  C12 0.4325(3) 0.56019(19) 0.1326(2) 0.0804(8) Uani d . 1 . . C
  H12 0.5086 0.5766 0.1673 0.096 Uiso calc R 1 . . H
  C13 0.4115(4) 0.5871(2) 0.0411(2) 0.1054(12) Uani d . 1 . . C
  H13 0.4733 0.6214 0.0146 0.126 Uiso calc R 1 . . H
  C14 0.3012(5) 0.5637(2) -0.0093(2) 0.0975(11) Uani d . 1 . . C
  H14 0.2871 0.5816 -0.0709 0.117 Uiso calc R 1 . . H
  C15 0.2104(4) 0.5139(2) 0.0299(2) 0.0940(10) Uani d . 1 . . C
  H15 0.1342 0.4981 -0.0051 0.113 Uiso calc R 1 . . H
  C16 0.2307(3) 0.48615(19) 0.12255(19) 0.0772(8) Uani d . 1 . . C
  H16 0.1685 0.4522 0.1492 0.093 Uiso calc R 1 . . H
  C31 0.8092(2) 0.40726(14) 0.37285(18) 0.0558(6) Uani d . 1 . . C
  C32 0.9315(3) 0.42194(18) 0.4143(2) 0.0761(8) Uani d . 1 . . C
  H32 0.9592 0.3951 0.4689 0.091 Uiso calc R 1 . . H
  C33 1.0139(3) 0.4775(2) 0.3738(3) 0.0988(11) Uani d . 1 . . C
  H33 1.0981 0.4884 0.4013 0.119 Uiso calc R 1 . . H
  C34 0.9730(5) 0.5167(2) 0.2939(3) 0.1024(12) Uani d . 1 . . C
  H34 1.0286 0.5545 0.2672 0.123 Uiso calc R 1 . . H
  C35 0.8493(4) 0.4999(2) 0.2530(2) 0.0994(11) Uani d . 1 . . C
  H35 0.8213 0.5263 0.1981 0.119 Uiso calc R 1 . . H
  C36 0.7656(3) 0.4438(2) 0.2928(2) 0.0778(8) Uani d . 1 . . C
  H36 0.6819 0.4317 0.2651 0.093 Uiso calc R 1 . . H
  C21A 0.7620(5) 0.2735(5) 0.6187(3) 0.0614(11) Uani d PGDU 0.50 A 1 C
  C22A 0.7274(4) 0.2986(4) 0.7079(4) 0.0685(11) Uani d PGU 0.50 A 1 C
  H22A 0.6423 0.3196 0.7173 0.082 Uiso calc PR 0.50 A 1 H
  C23A 0.8199(4) 0.2923(3) 0.7832(3) 0.0798(13) Uani d PGU 0.50 A 1 C
  H23A 0.7967 0.3091 0.8429 0.096 Uiso calc PR 0.50 A 1 H
  C24A 0.9471(4) 0.2609(3) 0.7692(3) 0.0812(14) Uani d PGU 0.50 A 1 C
  H24A 1.0090 0.2567 0.8196 0.097 Uiso calc PR 0.50 A 1 H
  C25A 0.9818(4) 0.2358(3) 0.6800(3) 0.0803(13) Uani d PGU 0.50 A 1 C
  H25A 1.0669 0.2148 0.6706 0.096 Uiso calc PR 0.50 A 1 H
  C26A 0.8892(5) 0.2421(4) 0.6047(3) 0.0737(12) Uani d PGU 0.50 A 1 C
  H26A 0.9124 0.2253 0.5450 0.088 Uiso calc PR 0.50 A 1 H
  C21B 0.7645(4) 0.2668(5) 0.6162(4) 0.0612(11) Uani d PGDU 0.50 A 2 C
  C22B 0.7693(4) 0.2888(4) 0.7107(4) 0.0711(11) Uani d PGU 0.50 A 2 C
  H22B 0.6964 0.3147 0.7363 0.085 Uiso calc PR 0.50 A 2 H
  C23B 0.8831(4) 0.2719(3) 0.7669(3) 0.0770(13) Uani d PGU 0.50 A 2 C
  H23B 0.8863 0.2866 0.8301 0.092 Uiso calc PR 0.50 A 2 H
  C24B 0.9920(3) 0.2331(3) 0.7286(3) 0.0776(13) Uani d PGU 0.50 A 2 C
  H24B 1.0681 0.2218 0.7661 0.093 Uiso calc PR 0.50 A 2 H
  C25B 0.9872(4) 0.2111(3) 0.6341(3) 0.0773(13) Uani d PGU 0.50 A 2 C
  H25B 1.0601 0.1852 0.6085 0.093 Uiso calc PR 0.50 A 2 H
  C26B 0.8735(5) 0.2280(4) 0.5779(3) 0.0684(12) Uani d PGU 0.50 A 2 C
  H26B 0.8703 0.2133 0.5147 0.082 Uiso calc PR 0.50 A 2 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 0.1148(6) 0.0614(4) 0.0518(4) 0.0187(4) -0.0161(4) -0.0198(3)
  C1 0.0529(13) 0.0469(13) 0.0421(12) 0.0004(10) -0.0052(10) -0.0042(10)
  N1 0.0812(14) 0.0473(12) 0.0368(11) 0.0036(10) -0.0037(10) -0.0034(9)
  N2 0.0683(13) 0.0410(11) 0.0384(10) 0.0050(9) -0.0078(9) -0.0078(9)
  C2 0.0582(13) 0.0393(11) 0.0445(12) 0.0011(10) -0.0039(10) -0.0025(10)
  C3 0.0578(15) 0.0575(15) 0.0698(17) -0.0032(12) -0.0007(13) 0.0124(13)
  C4 0.089(2) 0.094(2) 0.077(2) 0.0047(17) 0.0307(16) 0.0088(18)
  C5 0.0635(18) 0.082(2) 0.128(3) -0.0081(15) -0.0093(18) 0.016(2)
  C6 0.125(3) 0.078(2) 0.199(5) -0.020(2) -0.060(3) -0.003(3)
  P1 0.0528(3) 0.0391(3) 0.0439(3) 0.0005(2) -0.0016(3) -0.0037(2)
  O1 0.0643(10) 0.0414(8) 0.0455(8) -0.0007(7) -0.0030(7) -0.0060(7)
  O2 0.0635(10) 0.0434(9) 0.0729(11) -0.0014(7) -0.0200(9) 0.0059(8)
  O3 0.0781(12) 0.0537(10) 0.0719(12) -0.0082(8) 0.0259(9) -0.0175(9)
  C11 0.0688(15) 0.0527(14) 0.0398(13) 0.0089(12) -0.0022(11) -0.0012(11)
  C12 0.093(2) 0.083(2) 0.0641(18) -0.0123(17) -0.0077(15) 0.0172(16)
  C13 0.142(3) 0.099(3) 0.076(2) -0.017(2) 0.006(2) 0.031(2)
  C14 0.145(3) 0.092(2) 0.0546(19) 0.023(2) -0.013(2) 0.0104(18)
  C15 0.096(2) 0.121(3) 0.063(2) 0.016(2) -0.0290(18) -0.012(2)
  C16 0.0814(19) 0.092(2) 0.0577(17) -0.0027(16) -0.0077(15) -0.0055(15)
  C31 0.0584(15) 0.0534(14) 0.0566(15) -0.0032(11) 0.0149(12) -0.0122(12)
  C32 0.0632(17) 0.083(2) 0.0824(19) -0.0003(14) 0.0015(15) -0.0018(16)
  C33 0.068(2) 0.110(3) 0.119(3) -0.0288(19) 0.017(2) -0.023(2)
  C34 0.119(3) 0.086(2) 0.105(3) -0.035(2) 0.052(3) -0.012(2)
  C35 0.138(3) 0.095(2) 0.066(2) -0.001(2) 0.022(2) 0.0113(18)
  C36 0.0784(19) 0.093(2) 0.0624(18) -0.0052(17) 0.0039(15) -0.0023(17)
  C21A 0.0656(19) 0.052(2) 0.066(2) -0.0098(18) -0.0155(19) 0.0160(19)
  C22A 0.075(2) 0.059(2) 0.070(2) -0.012(2) -0.018(2) 0.020(2)
  C23A 0.082(3) 0.077(2) 0.079(2) -0.006(2) -0.023(2) 0.025(2)
  C24A 0.077(3) 0.083(3) 0.082(2) -0.003(2) -0.024(2) 0.025(2)
  C25A 0.074(2) 0.084(3) 0.081(3) -0.003(2) -0.026(2) 0.022(2)
  C26A 0.072(2) 0.072(2) 0.076(2) -0.003(2) -0.016(2) 0.018(2)
  C21B 0.0644(19) 0.052(2) 0.066(2) -0.0084(18) -0.0152(19) 0.0189(18)
  C22B 0.074(2) 0.066(2) 0.072(2) -0.009(2) -0.017(2) 0.0199(19)
  C23B 0.073(3) 0.083(3) 0.073(2) -0.008(2) -0.023(2) 0.026(2)
  C24B 0.076(2) 0.085(3) 0.070(3) -0.008(2) -0.020(2) 0.026(2)
  C25B 0.074(2) 0.080(3) 0.077(3) 0.000(2) -0.017(2) 0.020(2)
  C26B 0.065(2) 0.067(2) 0.071(2) 0.000(2) -0.017(2) 0.018(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 . 1.664(2) yes
  C1 N1 . 1.347(3) yes
  C1 N2 . 1.353(3) yes
  N1 C11 . 1.431(3) yes
  N1 H1 . 0.825(19) no
  N2 C2 . 1.450(3) yes
  N2 H2 . 0.833(19) no
  C2 C3 . 1.535(3) no
  C2 P1 . 1.808(2) yes
  C2 H201 . 0.9800 no
  C3 C5 . 1.513(4) no
  C3 C4 . 1.533(4) no
  C3 H301 . 0.9800 no
  C4 H401 . 0.9600 no
  C4 H402 . 0.9600 no
  C4 H403 . 0.9600 no
  C5 C6 . 1.494(5) no
  C5 H501 . 0.9700 no
  C5 H502 . 0.9700 no
  C6 H601 . 0.9600 no
  C6 H602 . 0.9600 no
  C6 H603 . 0.9600 no
  P1 O1 . 1.4667(14) yes
  P1 O3 . 1.5668(17) yes
  P1 O2 . 1.5758(16) yes
  O2 C21A . 1.367(3) no
  O2 C21B . 1.375(2) no
  O3 C31 . 1.413(3) no
  C11 C16 . 1.358(4) no
  C11 C12 . 1.368(4) no
  C12 C13 . 1.384(4) no
  C12 H12 . 0.9300 no
  C13 C14 . 1.347(5) no
  C13 H13 . 0.9300 no
  C14 C15 . 1.362(5) no
  C14 H14 . 0.9300 no
  C15 C16 . 1.403(4) no
  C15 H15 . 0.9300 no
  C16 H16 . 0.9300 no
  C31 C36 . 1.349(4) no
  C31 C32 . 1.354(4) no
  C32 C33 . 1.379(4) no
  C32 H32 . 0.9300 no
  C33 C34 . 1.360(5) no
  C33 H33 . 0.9300 no
  C34 C35 . 1.371(5) no
  C34 H34 . 0.9300 no
  C35 C36 . 1.389(4) no
  C35 H35 . 0.9300 no
  C36 H36 . 0.9300 no
  C21A C22A . 1.3900 no
  C21A C26A . 1.3900 no
  C22A C23A . 1.3900 no
  C22A H22A . 0.9300 no
  C23A C24A . 1.3900 no
  C23A H23A . 0.9300 no
  C24A C25A . 1.3900 no
  C24A H24A . 0.9300 no
  C25A C26A . 1.3900 no
  C25A H25A . 0.9300 no
  C26A H26A . 0.9300 no
  C21B C22B . 1.3900 no
  C21B C26B . 1.3900 no
  C22B C23B . 1.3900 no
  C22B H22B . 0.9300 no
  C23B C24B . 1.3900 no
  C23B H23B . 0.9300 no
  C24B C25B . 1.3900 no
  C24B H24B . 0.9300 no
  C25B C26B . 1.3900 no
  C25B H25B . 0.9300 no
  C26B H26B . 0.9300 no