#------------------------------------------------------------------------------
#$Date$
#$Revision$
#$URL$
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104189
loop_
_publ_author_name
'Cobo, Justo'
'Trilleras, Jorge'
'Quiroga, Jairo'
'Marchal, Antonio'
'Nogueras, Manuel'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 <i>N</i>^6^-Substituted 2-amino-4-chloro-5-formylpyrimidines: puckered
 <i>versus</i> planar pyrimidine rings, and hydrogen-bonded aggregation
 in zero, one, two and three dimensions
;
_journal_coeditor_code           BM5057
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              596
_journal_page_last               609
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C9 H13 Cl N4 O'
_chemical_formula_sum            'C9 H13 Cl N4 O'
_chemical_formula_weight         228.68
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.709(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.328(3)
_cell_length_b                   8.0810(4)
_cell_length_c                   11.3849(12)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      4.41
_cell_volume                     1030.2(3)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21126
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         4.41
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+1.3692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                1408
_reflns_number_total             2357
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm5057.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_atom_site_type_symbol
_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
N N1 0.4610(2) 0.3978(3) 0.6130(2) 0.0187(6) Uani d . 1
C C2 0.4704(3) 0.2420(4) 0.5792(3) 0.0186(7) Uani d . 1
N N2 0.5733(2) 0.1648(3) 0.6119(2) 0.0227(7) Uani d . 1
N N3 0.3803(2) 0.1501(3) 0.5177(2) 0.0186(6) Uani d . 1
C C4 0.2886(3) 0.2376(4) 0.4691(3) 0.0195(7) Uani d . 1
Cl Cl4 0.17783(7) 0.11931(10) 0.38568(7) 0.0246(3) Uani d . 1
C C5 0.2745(3) 0.4087(4) 0.4785(3) 0.0182(7) Uani d . 1
C C51 0.1943(3) 0.4955(4) 0.3876(3) 0.0214(7) Uani d . 1
O O51 0.20011(19) 0.6406(3) 0.3598(2) 0.0245(6) Uani d . 1
C C6 0.3614(3) 0.4822(4) 0.5689(3) 0.0189(7) Uani d . 1
N N61 0.3501(2) 0.6334(3) 0.6160(2) 0.0188(6) Uani d . 1
C C62 0.2380(3) 0.7273(4) 0.6073(3) 0.0225(8) Uani d . 1
C C63 0.1350(3) 0.6336(4) 0.6493(3) 0.0281(8) Uani d . 1
C C64 0.4488(3) 0.7008(4) 0.7017(3) 0.0211(7) Uani d . 1
C C65 0.4339(3) 0.6638(4) 0.8289(3) 0.0267(8) Uani d . 1
H H2A 0.6355 0.2226 0.6381 0.027 Uiso d R 1
H H2B 0.5826 0.0744 0.5745 0.027 Uiso d R 1
H H51 0.1306 0.4328 0.3454 0.026 Uiso calc R 1
H H62A 0.2134 0.7605 0.5234 0.027 Uiso calc R 1
H H62B 0.2530 0.8297 0.6549 0.027 Uiso calc R 1
H H63A 0.1105 0.5418 0.5947 0.042 Uiso calc R 1
H H63B 0.0674 0.7088 0.6507 0.042 Uiso calc R 1
H H63C 0.1610 0.5899 0.7293 0.042 Uiso calc R 1
H H64A 0.4528 0.8221 0.6909 0.025 Uiso calc R 1
H H64B 0.5251 0.6527 0.6855 0.025 Uiso calc R 1
H H65A 0.3589 0.7124 0.8457 0.040 Uiso calc R 1
H H65B 0.5009 0.7114 0.8828 0.040 Uiso calc R 1
H H65C 0.4321 0.5438 0.8407 0.040 Uiso calc R 1
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 0.0210(14) 0.0158(15) 0.0196(14) -0.0007(11) 0.0045(11) -0.0004(11)
C2 0.0214(17) 0.0174(17) 0.0179(16) 0.0004(14) 0.0061(13) 0.0011(13)
N2 0.0212(15) 0.0190(15) 0.0269(16) 0.0005(12) 0.0004(12) -0.0056(12)
N3 0.0200(14) 0.0145(15) 0.0221(14) 0.0009(11) 0.0055(11) 0.0003(11)
C4 0.0208(17) 0.0205(18) 0.0185(17) -0.0015(14) 0.0075(13) -0.0032(13)
Cl4 0.0231(4) 0.0193(4) 0.0307(5) -0.0024(4) 0.0017(3) -0.0041(4)
C5 0.0213(17) 0.0146(18) 0.0198(17) 0.0003(13) 0.0066(13) -0.0009(13)
C51 0.0210(18) 0.0218(19) 0.0217(17) 0.0011(14) 0.0043(14) -0.0037(14)
O51 0.0247(13) 0.0188(14) 0.0293(13) 0.0025(10) 0.0020(10) 0.0038(10)
C6 0.0199(17) 0.0153(17) 0.0228(17) -0.0036(14) 0.0074(13) 0.0016(13)
N61 0.0214(15) 0.0121(14) 0.0228(15) 0.0017(11) 0.0031(11) -0.0018(11)
C62 0.0237(18) 0.0141(17) 0.0298(19) 0.0060(13) 0.0042(15) -0.0011(14)
C63 0.029(2) 0.026(2) 0.031(2) 0.0048(16) 0.0087(15) -0.0024(16)
C64 0.0217(17) 0.0179(18) 0.0239(18) -0.0044(14) 0.0043(14) -0.0054(14)
C65 0.0272(19) 0.024(2) 0.0285(19) -0.0006(15) 0.0039(15) -0.0057(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.326(4) no
N1 C6 1.349(4) no
C2 N2 1.325(4) no
C2 N3 1.367(4) no
N2 H2A 0.86 no
N2 H2B 0.86 no
N3 C4 1.308(4) no
C4 C5 1.398(4) no
C4 Cl4 1.740(3) no
C5 C6 1.440(4) no
C5 C51 1.450(4) no
C51 O51 1.219(4) no
C51 H51 0.95 no
C6 N61 1.348(4) no
N61 C62 1.470(4) no
N61 C64 1.472(4) no
C62 C63 1.527(5) no
C62 H62A 0.99 no
C62 H62B 0.99 no
C63 H63A 0.98 no
C63 H63B 0.98 no
C63 H63C 0.98 no
C64 C65 1.513(5) no
C64 H64A 0.99 no
C64 H64B 0.99 no
C65 H65A 0.98 no
C65 H65B 0.98 no
C65 H65C 0.98 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 118.1(3) no
N2 C2 N1 118.1(3) no
N2 C2 N3 116.4(3) no
N1 C2 N3 125.3(3) no
C2 N2 H2A 118.8 no
C2 N2 H2B 115.4 no
H2A N2 H2B 118.6 no
C4 N3 C2 114.0(3) no
N3 C4 C5 126.5(3) no
N3 C4 Cl4 113.2(2) no
C5 C4 Cl4 120.2(2) no
C4 C5 C6 112.9(3) no
C4 C5 C51 119.4(3) no
C6 C5 C51 126.7(3) no
O51 C51 C5 126.7(3) no
O51 C51 H51 116.7 no
C5 C51 H51 116.7 no
N61 C6 N1 115.8(3) no
N61 C6 C5 124.2(3) no
N1 C6 C5 120.1(3) no
C6 N61 C62 125.1(3) no
C6 N61 C64 119.4(3) no
C62 N61 C64 114.6(3) no
N61 C62 C63 114.6(3) no
N61 C62 H62A 108.6 no
C63 C62 H62A 108.6 no
N61 C62 H62B 108.6 no
C63 C62 H62B 108.6 no
H62A C62 H62B 107.6 no
C62 C63 H63A 109.5 no
C62 C63 H63B 109.5 no
H63A C63 H63B 109.5 no
C62 C63 H63C 109.5 no
H63A C63 H63C 109.5 no
H63B C63 H63C 109.5 no
N61 C64 C65 112.2(3) no
N61 C64 H64A 109.2 no
C65 C64 H64A 109.2 no
N61 C64 H64B 109.2 no
C65 C64 H64B 109.2 no
H64A C64 H64B 107.9 no
C64 C65 H65A 109.5 no
C64 C65 H65B 109.5 no
H65A C65 H65B 109.5 no
C64 C65 H65C 109.5 no
H65A C65 H65C 109.5 no
H65B C65 H65C 109.5 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N2 172.7(3) no
C6 N1 C2 N3 -10.7(5) no
N2 C2 N3 C4 -168.3(3) no
N1 C2 N3 C4 15.1(4) no
C2 N3 C4 C5 -2.4(5) no
C2 N3 C4 Cl4 177.3(2) no
N3 C4 C5 C6 -12.2(5) no
Cl4 C4 C5 C6 168.1(2) no
N3 C4 C5 C51 156.6(3) no
Cl4 C4 C5 C51 -23.1(4) no
C4 C5 C51 O51 -153.8(3) no
C6 C5 C51 O51 13.2(5) no
C2 N1 C6 N61 172.8(3) no
C2 N1 C6 C5 -6.2(4) no
C4 C5 C6 N61 -162.6(3) no
C51 C5 C6 N61 29.6(5) no
C4 C5 C6 N1 16.4(4) no
C51 C5 C6 N1 -151.4(3) no
N1 C6 N61 C62 -162.3(3) no
C5 C6 N61 C62 16.7(5) no
N1 C6 N61 C64 5.4(4) no
C5 C6 N61 C64 -175.6(3) no
C6 N61 C62 C63 53.7(4) no
C64 N61 C62 C63 -114.5(3) no
C6 N61 C64 C65 -93.4(3) no
C62 N61 C64 C65 75.5(3) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A O51 3_666 0.86 2.16 2.986(3) 160 no
N2 H2B N3 3_656 0.86 2.17 3.026(3) 176 no