data_2012722
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o289
_journal_page_last  o294
_publ_section_title
;
Hydrogen bonding in 2-amino-4,6-dimethoxypyrimidine,
2-benzylamino-4,6-bis(benzyloxy)pyrimidine and
2-amino-4,6-bis(N-pyrrolidino)pyrimidine: chains of fused rings and a
centrosymmetric dimer
;
loop_
_publ_author_name
  'Low, John N.'
  'Quesada, Antonio'
  'Marchal, Antonio'
  'Melguizo, Manuel'
  'Nogueras, Manuel'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C25 H23 N3 O2'
_chemical_formula_sum  'C25 H23 N3 O2'
_chemical_formula_weight  397.46
_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  5.8083(6)
_cell_length_b  12.3104(13)
_cell_length_c  15.7260(16)
_cell_angle_alpha  68.549(2)
_cell_angle_beta  85.978(2)
_cell_angle_gamma  82.737(2)
_cell_volume  1037.81(19)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.272
_diffrn_ambient_temperature  120(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
  N1 1.06020(18) 0.15079(9) 0.43312(7) 0.0245(2) Uani d . 1 . . N
  C2 0.9040(2) 0.14975(10) 0.37413(8) 0.0234(2) Uani d . 1 . . C
  N2 0.81278(19) 0.04843(9) 0.39253(7) 0.0279(2) Uani d . 1 . . N
  C27 0.6332(2) 0.03365(11) 0.33940(8) 0.0261(3) Uani d . 1 . . C
  C21 0.7221(2) -0.00571(10) 0.26110(8) 0.0231(3) Uani d . 1 . . C
  C22 0.5881(2) -0.07097(11) 0.23235(8) 0.0275(3) Uani d . 1 . . C
  C23 0.6605(2) -0.10549(11) 0.15896(9) 0.0328(3) Uani d . 1 . . C
  C24 0.8691(2) -0.07512(12) 0.11369(9) 0.0334(3) Uani d . 1 . . C
  C25 1.0057(2) -0.01108(12) 0.14225(9) 0.0317(3) Uani d . 1 . . C
  C26 0.9327(2) 0.02341(11) 0.21554(8) 0.0272(3) Uani d . 1 . . C
  N3 0.82976(18) 0.24202(8) 0.29875(6) 0.0249(2) Uani d . 1 . . N
  C4 0.9258(2) 0.33947(10) 0.28374(8) 0.0238(3) Uani d . 1 . . C
  O4 0.85807(15) 0.43613(7) 0.21106(6) 0.0280(2) Uani d . 1 . . O
  C47 0.6792(2) 0.42567(11) 0.15532(9) 0.0321(3) Uani d . 1 . . C
  C41 0.6113(2) 0.54692(11) 0.08775(8) 0.0278(3) Uani d . 1 . . C
  C42 0.7715(3) 0.60873(13) 0.02532(11) 0.0409(3) Uani d . 1 . . C
  C43 0.7082(3) 0.72002(13) -0.03715(11) 0.0454(4) Uani d . 1 . . C
  C44 0.4837(3) 0.77170(12) -0.03714(10) 0.0392(3) Uani d . 1 . . C
  C45 0.3238(3) 0.71142(13) 0.02456(10) 0.0396(3) Uani d . 1 . . C
  C46 0.3856(2) 0.59913(12) 0.08676(9) 0.0334(3) Uani d . 1 . . C
  C5 1.0904(2) 0.35194(10) 0.33882(8) 0.0257(3) Uani d . 1 . . C
  C6 1.1484(2) 0.25220(10) 0.41456(8) 0.0237(3) Uani d . 1 . . C
  O6 1.29228(15) 0.24744(7) 0.48017(6) 0.0284(2) Uani d . 1 . . O
  C67 1.3823(3) 0.35596(11) 0.47016(9) 0.0338(3) Uani d . 1 . . C
  C61 1.5029(2) 0.34046(10) 0.55579(8) 0.0264(3) Uani d . 1 . . C
  C62 1.3964(2) 0.38608(11) 0.61912(9) 0.0280(3) Uani d . 1 . . C
  C63 1.5120(3) 0.37561(11) 0.69647(9) 0.0332(3) Uani d . 1 . . C
  C64 1.7358(2) 0.32039(11) 0.71061(9) 0.0347(3) Uani d . 1 . . C
  C65 1.8430(2) 0.27374(12) 0.64840(10) 0.0355(3) Uani d . 1 . . C
  C66 1.7265(2) 0.28324(11) 0.57154(9) 0.0320(3) Uani d . 1 . . C
  H2 0.8652 -0.0127 0.4397 0.033 Uiso calc R 1 . . H
  H27A 0.5340 0.1092 0.3143 0.031 Uiso calc R 1 . . H
  H27B 0.5343 -0.0248 0.3807 0.031 Uiso calc R 1 . . H
  H22 0.4449 -0.0923 0.2633 0.033 Uiso calc R 1 . . H
  H23 0.5667 -0.1499 0.1399 0.039 Uiso calc R 1 . . H
  H24 0.9185 -0.0981 0.0633 0.040 Uiso calc R 1 . . H
  H25 1.1497 0.0093 0.1116 0.038 Uiso calc R 1 . . H
  H26 1.0274 0.0673 0.2347 0.033 Uiso calc R 1 . . H
  H47A 0.5433 0.3942 0.1940 0.039 Uiso calc R 1 . . H
  H47B 0.7393 0.3720 0.1230 0.039 Uiso calc R 1 . . H
  H42 0.9273 0.5743 0.0253 0.049 Uiso calc R 1 . . H
  H43 0.8199 0.7608 -0.0801 0.054 Uiso calc R 1 . . H
  H44 0.4401 0.8484 -0.0795 0.047 Uiso calc R 1 . . H
  H45 0.1687 0.7468 0.0249 0.048 Uiso calc R 1 . . H
  H46 0.2725 0.5581 0.1288 0.040 Uiso calc R 1 . . H
  H5 1.1575 0.4230 0.3256 0.031 Uiso calc R 1 . . H
  H67A 1.2535 0.4200 0.4589 0.041 Uiso calc R 1 . . H
  H67B 1.4928 0.3774 0.4173 0.041 Uiso calc R 1 . . H
  H62 1.2431 0.4248 0.6094 0.034 Uiso calc R 1 . . H
  H63 1.4371 0.4065 0.7398 0.040 Uiso calc R 1 . . H
  H64 1.8158 0.3145 0.7630 0.042 Uiso calc R 1 . . H
  H65 1.9964 0.2352 0.6583 0.043 Uiso calc R 1 . . H
  H66 1.8002 0.2503 0.5293 0.038 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
  N1 0.0330(5) 0.0203(5) 0.0203(5) -0.0065(4) -0.0032(4) -0.0059(4)
  C2 0.0304(6) 0.0205(6) 0.0201(5) -0.0048(5) -0.0013(5) -0.0075(5)
  N2 0.0402(6) 0.0199(5) 0.0222(5) -0.0094(4) -0.0091(4) -0.0023(4)
  C27 0.0303(6) 0.0233(6) 0.0243(6) -0.0088(5) -0.0026(5) -0.0057(5)
  C21 0.0271(6) 0.0169(5) 0.0217(6) -0.0023(5) -0.0078(5) -0.0015(4)
  C22 0.0299(6) 0.0247(6) 0.0260(6) -0.0081(5) -0.0049(5) -0.0046(5)
  C23 0.0461(8) 0.0262(7) 0.0279(6) -0.0101(6) -0.0085(6) -0.0085(5)
  C24 0.0446(8) 0.0274(7) 0.0271(6) 0.0002(6) -0.0030(6) -0.0093(5)
  C25 0.0284(6) 0.0323(7) 0.0296(7) -0.0019(5) -0.0005(5) -0.0061(5)
  C26 0.0274(6) 0.0247(6) 0.0275(6) -0.0041(5) -0.0068(5) -0.0056(5)
  N3 0.0324(5) 0.0193(5) 0.0218(5) -0.0053(4) -0.0045(4) -0.0046(4)
  C4 0.0309(6) 0.0191(6) 0.0203(6) -0.0023(5) -0.0010(5) -0.0059(5)
  O4 0.0378(5) 0.0181(4) 0.0256(4) -0.0051(4) -0.0107(4) -0.0022(3)
  C47 0.0411(7) 0.0227(6) 0.0307(7) -0.0063(5) -0.0142(6) -0.0042(5)
  C41 0.0355(7) 0.0226(6) 0.0256(6) -0.0041(5) -0.0099(5) -0.0072(5)
  C42 0.0337(7) 0.0290(7) 0.0494(9) -0.0022(6) -0.0051(6) -0.0015(6)
  C43 0.0456(9) 0.0336(8) 0.0448(9) -0.0112(7) -0.0049(7) 0.0031(7)
  C44 0.0516(9) 0.0231(7) 0.0382(8) -0.0018(6) -0.0217(7) -0.0028(6)
  C45 0.0378(7) 0.0342(8) 0.0469(8) 0.0060(6) -0.0136(7) -0.0156(7)
  C46 0.0377(7) 0.0339(7) 0.0286(7) -0.0040(6) -0.0035(5) -0.0109(6)
  C5 0.0347(7) 0.0187(6) 0.0234(6) -0.0082(5) -0.0031(5) -0.0051(5)
  C6 0.0297(6) 0.0229(6) 0.0200(6) -0.0063(5) -0.0017(5) -0.0082(5)
  O6 0.0403(5) 0.0219(4) 0.0230(4) -0.0114(4) -0.0085(4) -0.0041(3)
  C67 0.0506(8) 0.0252(6) 0.0265(6) -0.0170(6) -0.0090(6) -0.0046(5)
  C61 0.0326(6) 0.0216(6) 0.0247(6) -0.0114(5) -0.0025(5) -0.0048(5)
  C62 0.0293(6) 0.0215(6) 0.0316(7) -0.0060(5) -0.0022(5) -0.0064(5)
  C63 0.0482(8) 0.0250(6) 0.0285(7) -0.0104(6) 0.0007(6) -0.0104(5)
  C64 0.0466(8) 0.0259(7) 0.0298(7) -0.0120(6) -0.0142(6) -0.0030(5)
  C65 0.0272(7) 0.0272(7) 0.0466(8) -0.0065(5) -0.0068(6) -0.0048(6)
  C66 0.0340(7) 0.0276(7) 0.0341(7) -0.0084(5) 0.0068(6) -0.0106(5)
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
  N1 C2 . 1.3466(15) y
  C2 N3 . 1.3582(15) y
  N3 C4 . 1.3227(15) y
  C4 C5 . 1.3925(17) y
  C5 C6 . 1.3863(16) y
  C6 N1 . 1.3342(15) y
  C2 N2 . 1.3424(15) y
  N2 C27 . 1.4495(15) y
  C4 O4 . 1.3516(14) y
  O4 C47 . 1.4522(14) y
  C6 O6 . 1.3530(14) y
  O6 C67 . 1.4470(15) y
  N2 H2 . 0.8800 no
  C27 C21 . 1.5172(17) no
  C27 H27A . 0.9900 no
  C27 H27B . 0.9900 no
  C21 C22 . 1.3886(16) no
  C21 C26 . 1.3923(17) no
  C22 C23 . 1.3910(18) no
  C22 H22 . 0.9500 no
  C23 C24 . 1.383(2) no
  C23 H23 . 0.9500 no
  C24 C25 . 1.3854(19) no
  C24 H24 . 0.9500 no
  C25 C26 . 1.3900(18) no
  C25 H25 . 0.9500 no
  C26 H26 . 0.9500 no
  C47 C41 . 1.5042(17) no
  C47 H47A . 0.9900 no
  C47 H47B . 0.9900 no
  C41 C42 . 1.3831(19) no
  C41 C46 . 1.3833(19) no
  C42 C43 . 1.384(2) no
  C42 H42 . 0.9500 no
  C43 C44 . 1.377(2) no
  C43 H43 . 0.9500 no
  C44 C45 . 1.370(2) no
  C44 H44 . 0.9500 no
  C45 C46 . 1.390(2) no
  C45 H45 . 0.9500 no
  C46 H46 . 0.9500 no
  C5 H5 . 0.9500 no
  C67 C61 . 1.5005(17) no
  C67 H67A . 0.9900 no
  C67 H67B . 0.9900 no
  C61 C62 . 1.3872(18) no
  C61 C66 . 1.3894(18) no
  C62 C63 . 1.3872(18) no
  C62 H62 . 0.9500 no
  C63 C64 . 1.381(2) no
  C63 H63 . 0.9500 no
  C64 C65 . 1.382(2) no
  C64 H64 . 0.9500 no
  C65 C66 . 1.3871(19) no
  C65 H65 . 0.9500 no
  C66 H66 . 0.9500 no