data_2013196 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o4 _journal_page_last o8 _publ_section_title ; Two polymorphs of 2-amino-4-chloro-6-morpholinopyrimidine in P2~1~/c with Z' = 1 and Z' = 2, and 2-amino-4-chloro-6-piperidinopyrimidine, isomorphous and almost isostructural with the Z' = 2 polymorph ; loop_ _publ_author_name 'Bowes, Katharine F.' 'Glidewell, Christopher' 'Low, John N.' 'Melguizo, Manuel' 'Quesada, Antonio' _chemical_formula_moiety 'C8 H11 Cl N4 O' _chemical_formula_sum 'C8 H11 Cl N4 O' _chemical_formula_iupac 'C8 H11 Cl N4 O' _chemical_formula_weight 214.66 _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 13.9215(3) _cell_length_b 8.1803(2) _cell_length_c 19.6390(4) _cell_angle_alpha 90.00 _cell_angle_beta 121.6130(12) _cell_angle_gamma 90.00 _cell_volume 1904.65(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150.0(10) _exptl_crystal_density_diffrn 1.497 _diffrn_ambient_temperature 150.0(10) 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 N11 0.79843(10) 0.20269(15) 0.47727(7) 0.0157(3) Uani d . 1 . . N C12 0.87493(13) 0.31923(18) 0.49071(9) 0.0159(3) Uani d . 1 . . C N12 0.83577(11) 0.46261(16) 0.45255(8) 0.0196(3) Uani d . 1 . . N N13 0.98819(10) 0.30662(16) 0.53999(7) 0.0171(3) Uani d . 1 . . N C14 1.02161(12) 0.16575(18) 0.57935(9) 0.0161(3) Uani d . 1 . . C Cl14 1.16729(3) 0.14980(5) 0.64376(2) 0.02322(12) Uani d . 1 . . Cl C15 0.95440(12) 0.03841(18) 0.57365(9) 0.0163(3) Uani d . 1 . . C C16 0.83789(12) 0.06163(18) 0.51820(8) 0.0151(3) Uani d . 1 . . C N161 0.76117(10) -0.05594(16) 0.50384(7) 0.0189(3) Uani d . 1 . . N C162 0.78149(14) -0.19507(19) 0.55632(10) 0.0216(3) Uani d . 1 . . C C163 0.68697(13) -0.2016(2) 0.57320(9) 0.0223(3) Uani d . 1 . . C O164 0.57956(9) -0.21304(13) 0.50117(7) 0.0214(2) Uani d . 1 . . O C165 0.55954(13) -0.07493(19) 0.45042(9) 0.0197(3) Uani d . 1 . . C C166 0.65010(12) -0.0603(2) 0.43037(9) 0.0184(3) Uani d . 1 . . C N21 0.41915(10) 0.52848(15) 0.36586(7) 0.0160(3) Uani d . 1 . . N C22 0.52244(12) 0.47297(18) 0.38765(8) 0.0155(3) Uani d . 1 . . C N22 0.57501(11) 0.37564(16) 0.45215(8) 0.0192(3) Uani d . 1 . . N N23 0.57955(10) 0.50596(15) 0.35056(7) 0.0153(3) Uani d . 1 . . N C24 0.52311(12) 0.60138(18) 0.28705(8) 0.0148(3) Uani d . 1 . . C Cl24 0.59211(3) 0.64279(5) 0.23570(2) 0.01897(11) Uani d . 1 . . Cl C25 0.41932(13) 0.66938(18) 0.25868(9) 0.0165(3) Uani d . 1 . . C C26 0.36881(12) 0.62934(18) 0.30311(9) 0.0153(3) Uani d . 1 . . C N261 0.26690(11) 0.69436(16) 0.28426(8) 0.0177(3) Uani d . 1 . . N C262 0.19982(13) 0.78362(19) 0.20911(9) 0.0187(3) Uani d . 1 . . C C263 0.10854(14) 0.8840(2) 0.20937(10) 0.0251(4) Uani d . 1 . . C O264 0.04106(10) 0.78723(16) 0.22870(7) 0.0278(3) Uani d . 1 . . O C265 0.11157(14) 0.7239(2) 0.30760(10) 0.0269(4) Uani d . 1 . . C C266 0.20157(13) 0.6115(2) 0.31349(9) 0.0205(3) Uani d . 1 . . C H11 0.7628 0.4775 0.4203 0.024 Uiso calc R 1 . . H H12 0.8832 0.5416 0.4598 0.024 Uiso calc R 1 . . H H151 0.9836 -0.0584 0.6046 0.020 Uiso calc R 1 . . H H13 0.8550 -0.1824 0.6069 0.026 Uiso calc R 1 . . H H14 0.7832 -0.2976 0.5302 0.026 Uiso calc R 1 . . H H15 0.6981 -0.2974 0.6074 0.027 Uiso calc R 1 . . H H16 0.6894 -0.1021 0.6027 0.027 Uiso calc R 1 . . H H17 0.5580 0.0260 0.4777 0.024 Uiso calc R 1 . . H H18 0.4851 -0.0868 0.4005 0.024 Uiso calc R 1 . . H H19 0.6457 -0.1546 0.3972 0.022 Uiso calc R 1 . . H H110 0.6383 0.0409 0.3992 0.022 Uiso calc R 1 . . H H21 0.5419 0.3503 0.4785 0.023 Uiso calc R 1 . . H H22 0.6426 0.3372 0.4681 0.023 Uiso calc R 1 . . H H251 0.3839 0.7380 0.2129 0.020 Uiso calc R 1 . . H H23 0.1647 0.7051 0.1641 0.022 Uiso calc R 1 . . H H24 0.2497 0.8568 0.2011 0.022 Uiso calc R 1 . . H H25 0.1439 0.9736 0.2488 0.030 Uiso calc R 1 . . H H26 0.0598 0.9338 0.1560 0.030 Uiso calc R 1 . . H H27 0.0646 0.6634 0.3233 0.032 Uiso calc R 1 . . H H28 0.1479 0.8159 0.3454 0.032 Uiso calc R 1 . . H H29 0.2526 0.5779 0.3698 0.025 Uiso calc R 1 . . H H210 0.1660 0.5119 0.2813 0.025 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 N11 0.0126(6) 0.0174(6) 0.0162(6) -0.0020(5) 0.0069(5) 0.0000(5) C12 0.0148(7) 0.0184(7) 0.0149(7) -0.0014(6) 0.0080(6) -0.0011(6) N12 0.0120(6) 0.0177(6) 0.0232(7) -0.0021(5) 0.0051(5) 0.0030(5) N13 0.0125(6) 0.0180(6) 0.0187(6) -0.0022(5) 0.0068(5) 0.0001(5) C14 0.0108(7) 0.0198(7) 0.0158(7) 0.0003(5) 0.0057(6) -0.0013(6) Cl14 0.01039(19) 0.0251(2) 0.0273(2) -0.00093(14) 0.00509(17) 0.00521(15) C15 0.0139(7) 0.0163(7) 0.0182(7) 0.0005(6) 0.0080(6) 0.0010(6) C16 0.0149(7) 0.0172(7) 0.0145(7) -0.0024(6) 0.0086(6) -0.0030(6) N161 0.0126(6) 0.0210(7) 0.0178(6) -0.0040(5) 0.0043(5) 0.0031(5) C162 0.0172(8) 0.0184(7) 0.0256(8) -0.0018(6) 0.0087(7) 0.0040(6) C163 0.0185(8) 0.0232(8) 0.0212(8) -0.0029(6) 0.0077(7) 0.0049(6) O164 0.0161(6) 0.0202(6) 0.0254(6) -0.0028(4) 0.0092(5) 0.0048(5) C165 0.0170(7) 0.0188(8) 0.0209(7) -0.0009(6) 0.0084(6) 0.0038(6) C166 0.0139(7) 0.0216(8) 0.0157(7) -0.0045(6) 0.0049(6) -0.0003(6) N21 0.0136(6) 0.0170(6) 0.0162(6) 0.0002(5) 0.0070(5) 0.0001(5) C22 0.0143(7) 0.0143(7) 0.0140(7) -0.0028(5) 0.0047(6) -0.0021(5) N22 0.0156(6) 0.0222(7) 0.0196(7) 0.0032(5) 0.0090(6) 0.0069(5) N23 0.0131(6) 0.0151(6) 0.0152(6) -0.0011(5) 0.0057(5) -0.0001(5) C24 0.0137(7) 0.0163(7) 0.0149(7) -0.0042(6) 0.0079(6) -0.0034(6) Cl24 0.01498(19) 0.0246(2) 0.01833(19) -0.00025(14) 0.00942(16) 0.00275(14) C25 0.0149(7) 0.0174(7) 0.0147(7) 0.0013(6) 0.0060(6) 0.0014(6) C26 0.0118(7) 0.0148(7) 0.0153(7) -0.0021(5) 0.0044(6) -0.0036(6) N261 0.0135(6) 0.0197(6) 0.0189(6) 0.0022(5) 0.0079(5) 0.0024(5) C262 0.0155(7) 0.0191(8) 0.0192(7) 0.0032(6) 0.0076(6) 0.0022(6) C263 0.0201(8) 0.0256(8) 0.0278(9) 0.0057(7) 0.0112(7) 0.0026(7) O264 0.0161(6) 0.0385(7) 0.0269(6) 0.0065(5) 0.0099(5) 0.0041(5) C265 0.0218(9) 0.0367(10) 0.0246(8) 0.0060(7) 0.0138(7) 0.0008(7) C266 0.0162(8) 0.0263(8) 0.0194(8) 0.0006(6) 0.0095(7) 0.0015(6) 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 N11 C16 . 1.348(2) no N11 C12 . 1.3483(19) no C12 N12 . 1.3440(19) no C12 N13 . 1.354(2) no N12 H11 . 0.88 no N12 H12 . 0.88 no N13 C14 . 1.328(2) no C14 C15 . 1.365(2) no C14 Cl14 . 1.7438(15) no C15 C16 . 1.415(2) no C15 H151 . 0.95 no C16 N161 . 1.3526(19) no N161 C162 . 1.460(2) no N161 C166 . 1.4612(19) no C162 C163 . 1.517(2) no C162 H13 . 0.99 no C162 H14 . 0.99 no C163 O164 . 1.4242(19) no C163 H15 . 0.99 no C163 H16 . 0.99 no O164 C165 . 1.4339(18) no C165 C166 . 1.510(2) no C165 H17 . 0.99 no C165 H18 . 0.99 no C166 H19 . 0.99 no C166 H110 . 0.99 no N21 C26 . 1.3361(19) no N21 C22 . 1.3460(19) no C22 N22 . 1.3425(19) no C22 N23 . 1.3575(19) no N22 H21 . 0.88 no N22 H22 . 0.88 no N23 C24 . 1.3247(19) no C24 C25 . 1.365(2) no C24 Cl24 . 1.7521(14) no C25 C26 . 1.417(2) no C25 H251 . 0.95 no C26 N261 . 1.3719(19) no N261 C262 . 1.462(2) no N261 C266 . 1.471(2) no C262 C263 . 1.515(2) no C262 H23 . 0.99 no C262 H24 . 0.99 no C263 O264 . 1.424(2) no C263 H25 . 0.99 no C263 H26 . 0.99 no O264 C265 . 1.428(2) no C265 C266 . 1.509(2) no C265 H27 . 0.99 no C265 H28 . 0.99 no C266 H29 . 0.99 no C266 H210 . 0.99 no