data_2200116
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o198
_journal_page_last  o199
_publ_section_title
;
6-Chloro-2-methylthio-4-[(2-phenylethyl)amino]pyrimidine
;
loop_
_publ_author_name
  'Lynch, Daniel E.'
  'McClenaghan, Ian'
_chemical_formula_sum  'C26 H28 Cl2 N6 S2'
_chemical_formula_weight  559.56
_chemical_melting_point  '360 - 362 K'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  20.038(4)
_cell_length_b  11.358(2)
_cell_length_c  12.043(2)
_cell_angle_alpha  90.00
_cell_angle_beta  92.03(3)
_cell_angle_gamma  90.00
_cell_volume  2739.3(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.357
_diffrn_ambient_temperature  150(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
  N1A  .21983(9)  .22821(17)  -.07175(13)  .0299(4) Uani d . 1 . . N
  C2A  .18349(10)  .13330(19)  -.04914(17)  .0261(5) Uani d . 1 . . C
  S21A  .15169(3)  .06327(6)  -.16984(4)  .03741(17) Uani d . 1 . . S
  C22A  .10681(14)  -.0583(2)  -.1144(2)  .0475(7) Uani d . 1 . . C
  H21A  .1371  -.1060  -.0672  .059 Uiso calc R 1 . . H
  H22A  .0885  -.1068  -.1755  .059 Uiso calc R 1 . . H
  H23A  .0702  -.0288  -.0702  .059 Uiso calc R 1 . . H
  N3A  .16950(8)  .08903(15)  .04949(13)  .0259(4) Uani d . 1 . . N
  C4A  .19588(10)  .14708(19)  .13799(16)  .0256(5) Uani d . 1 . . C
  N41A  .18329(10)  .10783(18)  .23989(15)  .0348(5) Uani d . 1 . . N
  H4A  .1987(12)  .154(2)  .293(2)  .045(8) Uiso d . 1 . . H
  C42A  .14349(14)  .0053(2)  .26622(19)  .0431(6) Uani d . 1 . . C
  H41A  .1733  -.0595  .2917  .054 Uiso calc R 1 . . H
  H42A  .1183  -.0214  .1987  .054 Uiso calc R 1 . . H
  C43A  .09690(18)  .0336(3)  .3530(3)  .0742(10) Uani d . 1 . . C
  H43A  .0632  .0896  .3222  .093 Uiso calc R 1 . . H
  H44A  .1218  .0741  .4143  .093 Uiso calc R 1 . . H
  C44A  .06088(12)  -.0709(2)  .4006(2)  .0434(6) Uani d . 1 . . C
  C45A  .00747(13)  -.1226(3)  .3445(2)  .0477(7) Uani d . 1 . . C
  H45A  -.0055  -.0949  .2725  .060 Uiso calc R 1 . . H
  C46A  -.02761(13)  -.2137(3)  .3905(2)  .0501(7) Uani d . 1 . . C
  H46A  -.0647  -.2475  .3507  .063 Uiso calc R 1 . . H
  C47A  -.00903(14)  -.2555(3)  .4935(3)  .0528(7) Uani d . 1 . . C
  H47A  -.0331  -.3182  .5257  .066 Uiso calc R 1 . . H
  C48A  .04458(16)  -.2063(3)  .5497(2)  .0593(8) Uani d . 1 . . C
  H48A  .0580  -.2356  .6208  .074 Uiso calc R 1 . . H
  C49A  .07907(13)  -.1149(3)  .5040(2)  .0531(7) Uani d . 1 . . C
  H49A  .1160  -.0814  .5443  .066 Uiso calc R 1 . . H
  C5A  .23579(10)  .2477(2)  .12570(16)  .0281(5) Uani d . 1 . . C
  H5A  .2549  .2888  .1877  .035 Uiso calc R 1 . . H
  C6A  .24516(10)  .2822(2)  .01983(17)  .0289(5) Uani d . 1 . . C
  Cl6A  .29257(4)  .40626(6)  -.00536(5)  .0552(2) Uani d . 1 . . Cl
  N1B  .51355(8)  .71905(16)  .11772(13)  .0263(4) Uani d . 1 . . N
  C2B  .55408(9)  .81211(18)  .10665(15)  .0222(4) Uani d . 1 . . C
  S21B  .59942(3)  .84610(5)  .22985(4)  .03081(16) Uani d . 1 . . S
  C22B  .64533(11)  .9736(2)  .18981(17)  .0332(5) Uani d . 1 . . C
  H21B  .6769  .9517  .1330  .042 Uiso calc R 1 . . H
  H22B  .6699 1.0056  .2548  .042 Uiso calc R 1 . . H
  H23B  .6143 1.0332  .1598  .042 Uiso calc R 1 . . H
  N3B  .56205(8)  .87841(15)  .01758(12)  .0218(4) Uani d . 1 . . N
  C4B  .52500(9)  .84814(18)  -.07409(15)  .0225(4) Uani d . 1 . . C
  N41B  .53134(9)  .91376(16)  -.16581(14)  .0246(4) Uani d . 1 . . N
  H4B  .5172(11)  .884(2)  -.224(2)  .035(7) Uiso d . 1 . . H
  C42B  .57422(10) 1.01590(18)  -.17058(16)  .0255(5) Uani d . 1 . . C
  H41B  .5718 1.0597  -.0997  .032 Uiso calc R 1 . . H
  H42B  .5571 1.0683  -.2308  .032 Uiso calc R 1 . . H
  C43B  .64724(11)  .9870(2)  -.19073(18)  .0316(5) Uani d . 1 . . C
  H43B  .6644  .9317  -.1329  .040 Uiso calc R 1 . . H
  H44B  .6507  .9482  -.2639  .040 Uiso calc R 1 . . H
  C44B  .68860(10) 1.09734(19)  -.18786(17)  .0283(5) Uani d . 1 . . C
  C45B  .71708(12) 1.1389(2)  -.08867(18)  .0375(6) Uani d . 1 . . C
  H45B  .7118 1.0949  -.0225  .047 Uiso calc R 1 . . H
  C46B  .75285(13) 1.2424(2)  -.08407(19)  .0418(6) Uani d . 1 . . C
  H46B  .7717 1.2689  -.0150  .052 Uiso calc R 1 . . H
  C47B  .76148(12) 1.3080(2)  -.17899(18)  .0366(5) Uani d . 1 . . C
  H47B  .7861 1.3795  -.1759  .046 Uiso calc R 1 . . H
  C48B  .73374(11) 1.2681(2)  -.27793(17)  .0346(5) Uani d . 1 . . C
  H48B  .7394 1.3125  -.3438  .043 Uiso calc R 1 . . H
  C49B  .69775(11) 1.1644(2)  -.28296(17)  .0319(5) Uani d . 1 . . C
  H49B  .6790 1.1385  -.3523  .040 Uiso calc R 1 . . H
  C5B  .48059(10)  .75290(19)  -.07229(16)  .0261(5) Uani d . 1 . . C
  H5B  .4539  .7314  -.1359  .033 Uiso calc R 1 . . H
  C6B  .47762(10)  .69297(19)  .02493(16)  .0253(4) Uani d . 1 . . C
  Cl6B  .42403(3)  .57459(5)  .03666(5)  .04045(17) Uani d . 1 . . Cl
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
  N1A  .0328(10)  .0318(11)  .0250(9)  -.0062(8)  -.0011(7)  .0006(8)
  C2A  .0225(11)  .0268(12)  .0290(11)  .0003(9)  .0016(8)  -.0032(9)
  S21A  .0460(4)  .0389(4)  .0272(3)  -.0109(3)  .0001(2)  -.0076(2)
  C22A  .0563(17)  .0384(16)  .0477(15)  -.0184(13)  .0023(12)  -.0100(12)
  N3A  .0278(9)  .0243(10)  .0258(9)  .0001(8)  .0029(7)  -.0007(7)
  C4A  .0252(11)  .0252(12)  .0264(11)  .0026(9)  .0031(8)  .0023(8)
  N41A  .0484(12)  .0318(12)  .0247(10)  -.0078(9)  .0062(8)  -.0004(8)
  C42A  .0627(17)  .0316(14)  .0359(12)  -.0082(12)  .0166(11)  .0024(10)
  C43A  .075(2)  .051(2)  .101(3)  -.0199(17)  .0514(19)  -.0166(18)
  C44A  .0384(14)  .0403(16)  .0530(15)  -.0068(11)  .0198(12)  -.0084(12)
  C45A  .0490(16)  .0533(18)  .0410(14)  -.0028(13)  .0044(11)  .0019(12)
  C46A  .0365(15)  .0479(18)  .0662(18)  -.0072(13)  .0041(12)  -.0122(14)
  C47A  .0532(17)  .0352(16)  .0720(19)  -.0007(13)  .0295(14)  .0049(14)
  C48A  .065(2)  .067(2)  .0470(16)  .0172(17)  .0070(14)  .0080(15)
  C49A  .0342(15)  .065(2)  .0606(18)  .0013(13)  .0011(12)  -.0179(15)
  C5A  .0275(11)  .0319(13)  .0247(10)  -.0021(9)  -.0022(8)  -.0020(9)
  C6A  .0275(11)  .0288(13)  .0301(11)  -.0052(9)  -.0009(8)  .0036(9)
  Cl6A  .0730(5)  .0579(5)  .0343(3)  -.0420(4)  -.0042(3)  .0065(3)
  N1B  .0293(10)  .0245(10)  .0248(9)  -.0022(8)  -.0030(7)  .0024(7)
  C2B  .0234(10)  .0226(11)  .0205(9)  .0007(8)  -.0008(7)  .0006(8)
  S21B  .0357(3)  .0351(3)  .0211(3)  -.0090(2)  -.0072(2)  .0040(2)
  C22B  .0374(13)  .0338(14)  .0280(11)  -.0099(10)  -.0063(9)  .0010(9)
  N3B  .0244(9)  .0224(9)  .0185(8)  .0004(7)  -.0002(6)  -.0014(7)
  C4B  .0228(10)  .0241(12)  .0203(9)  .0026(8)  -.0006(7)  -.0031(8)
  N41B  .0289(10)  .0273(11)  .0172(9)  -.0027(8)  -.0022(7)  .0005(7)
  C42B  .0315(12)  .0211(12)  .0237(10)  -.0004(9)  -.0002(8)  .0033(8)
  C43B  .0313(12)  .0269(13)  .0370(12)  -.0002(10)  .0069(9)  -.0032(9)
  C44B  .0260(11)  .0273(13)  .0317(11)  .0044(9)  .0046(8)  -.0002(9)
  C45B  .0475(15)  .0383(15)  .0266(12)  -.0071(11)  .0009(10)  .0070(10)
  C46B  .0532(16)  .0440(16)  .0275(12)  -.0163(12)  -.0072(10)  .0030(10)
  C47B  .0400(13)  .0308(14)  .0388(13)  -.0078(11)  .0011(10)  .0012(10)
  C48B  .0436(14)  .0323(14)  .0281(11)  .0013(11)  .0054(9)  .0084(9)
  C49B  .0360(13)  .0345(14)  .0251(11)  .0019(10)  .0020(9)  -.0004(9)
  C5B  .0302(11)  .0262(12)  .0215(10)  -.0019(9)  -.0035(8)  -.0037(8)
  C6B  .0256(11)  .0223(12)  .0278(11)  -.0030(9)  -.0019(8)  .0007(8)
  Cl6B  .0442(4)  .0359(4)  .0406(3)  -.0188(3)  -.0075(2)  .0082(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
  N1A C2A . 1.334(3) ?
  N1A C6A . 1.346(3) ?
  C2A N3A . 1.329(3) ?
  C2A S21A . 1.757(2) ?
  S21A C22A . 1.790(3) ?
  C22A H21A .  .9800 ?
  C22A H22A .  .9800 ?
  C22A H23A .  .9800 ?
  N3A C4A . 1.345(3) ?
  C4A N41A . 1.338(3) ?
  C4A C5A . 1.406(3) ?
  N41A C42A . 1.453(3) ?
  N41A H4A .  .87(3) ?
  C42A C43A . 1.462(4) ?
  C42A H41A .  .9900 ?
  C42A H42A .  .9900 ?
  C43A C44A . 1.512(4) ?
  C43A H43A .  .9900 ?
  C43A H44A .  .9900 ?
  C44A C49A . 1.379(4) ?
  C44A C45A . 1.377(4) ?
  C45A C46A . 1.378(4) ?
  C45A H45A .  .9500 ?
  C46A C47A . 1.367(4) ?
  C46A H46A .  .9500 ?
  C47A C48A . 1.369(4) ?
  C47A H47A .  .9500 ?
  C48A C49A . 1.373(4) ?
  C48A H48A .  .9500 ?
  C49A H49A .  .9500 ?
  C5A C6A . 1.353(3) ?
  C5A H5A .  .9500 ?
  C6A Cl6A . 1.732(2) ?
  N1B C6B . 1.341(2) ?
  N1B C2B . 1.343(3) ?
  C2B N3B . 1.325(2) ?
  C2B S21B . 1.7551(19) ?
  S21B C22B . 1.791(2) ?
  C22B H21B .  .9800 ?
  C22B H22B .  .9800 ?
  C22B H23B .  .9800 ?
  N3B C4B . 1.353(2) ?
  C4B N41B . 1.342(3) ?
  C4B C5B . 1.401(3) ?
  N41B C42B . 1.446(3) ?
  N41B H4B .  .82(2) ?
  C42B C43B . 1.527(3) ?
  C42B H41B .  .9900 ?
  C42B H42B .  .9900 ?
  C43B C44B . 1.503(3) ?
  C43B H43B .  .9900 ?
  C43B H44B .  .9900 ?
  C44B C45B . 1.388(3) ?
  C44B C49B . 1.393(3) ?
  C45B C46B . 1.377(3) ?
  C45B H45B .  .9500 ?
  C46B C47B . 1.381(3) ?
  C46B H46B .  .9500 ?
  C47B C48B . 1.374(3) ?
  C47B H47B .  .9500 ?
  C48B C49B . 1.381(3) ?
  C48B H48B .  .9500 ?
  C49B H49B .  .9500 ?
  C5B C6B . 1.357(3) ?
  C5B H5B .  .9500 ?
  C6B Cl6B . 1.730(2) ?