#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017862.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017862
loop_
_publ_author_name
'Gálvez, Jaime A.'
'Quiroga, Jairo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 2-Cyano-N-(4,6-dimethoxypyrimidin-2-yl)acetamide: complex sheets
 built from N---H···O and
 C---H···O hydrogen bonds
;
_journal_coeditor_code           SK3387
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o521
_journal_page_last               o523
_journal_paper_doi               10.1107/S010827011003619X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H10 N4 O3'
_chemical_formula_moiety         'C9 H10 N4 O3'
_chemical_formula_sum            'C9 H10 N4 O3'
_chemical_formula_weight         222.21
_chemical_name_systematic
;
2-Cyano-N-(4,6-dimethoxypyrimidin-2-yl)acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                116.929(15)
_cell_angle_beta                 90.478(13)
_cell_angle_gamma                95.767(15)
_cell_formula_units_Z            2
_cell_length_a                   4.1760(6)
_cell_length_b                   11.296(2)
_cell_length_c                   12.070(3)
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.36
_cell_volume                     504.13(18)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12440
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0639P)²+0.5073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                1564
_reflns_number_total             2325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3387.cif
_cod_data_source_block           I
_cod_database_code               2017862
_cod_database_fobs_code          2017862
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5465(5) 0.3773(2) 0.24882(18) 0.0232(5) Uani d . 1 . .
C C2 0.4461(6) 0.2993(2) 0.3000(2) 0.0221(5) Uani d . 1 . .
N N3 0.5053(5) 0.17523(19) 0.26691(18) 0.0228(5) Uani d . 1 . .
C C4 0.6852(6) 0.1246(2) 0.1696(2) 0.0234(5) Uani d . 1 . .
C C5 0.8071(6) 0.1937(2) 0.1079(2) 0.0253(5) Uani d . 1 . .
H H5 0.9377 0.1559 0.0391 0.030 Uiso calc R 1 . .
C C6 0.7264(6) 0.3219(2) 0.1530(2) 0.0246(5) Uani d . 1 . .
N N21 0.2476(5) 0.3594(2) 0.39712(18) 0.0224(5) Uani d . 1 . .
H H21 0.2078 0.4398 0.4107 0.027 Uiso calc R 1 . .
C C22 0.1051(6) 0.3162(2) 0.4742(2) 0.0220(5) Uani d . 1 . .
O O22 -0.0883(4) 0.38088(16) 0.54600(15) 0.0255(4) Uani d . 1 . .
C C23 0.1928(6) 0.1902(3) 0.4747(2) 0.0278(6) Uani d . 1 . .
H H23A 0.1494 0.1144 0.3903 0.033 Uiso calc R 1 . .
H H23B 0.4256 0.2008 0.4979 0.033 Uiso calc R 1 . .
C C24 0.0062(6) 0.1624(2) 0.5627(2) 0.0270(6) Uani d . 1 . .
N N25 -0.1415(6) 0.1386(2) 0.6301(2) 0.0351(6) Uani d . 1 . .
O O41 0.7527(4) -0.00101(17) 0.12940(16) 0.0287(4) Uani d . 1 . .
C C41 0.5930(7) -0.0778(3) 0.1846(2) 0.0306(6) Uani d . 1 . .
H H41A 0.6631 -0.0379 0.2730 0.046 Uiso calc R 1 . .
H H41B 0.6477 -0.1698 0.1424 0.046 Uiso calc R 1 . .
H H41C 0.3593 -0.0783 0.1761 0.046 Uiso calc R 1 . .
O O61 0.8334(4) 0.39282(17) 0.09430(16) 0.0302(5) Uani d . 1 . .
C C61 0.7600(8) 0.5286(3) 0.1461(3) 0.0375(7) Uani d . 1 . .
H H61A 0.5263 0.5299 0.1515 0.056 Uiso calc R 1 . .
H H61B 0.8373 0.5685 0.0927 0.056 Uiso calc R 1 . .
H H61C 0.8665 0.5800 0.2296 0.056 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 114.7(2) ?
N3 C2 N1 . . 127.9(2) ?
N3 C2 N21 . . 119.2(2) ?
N1 C2 N21 . . 112.8(2) ?
C2 N3 C4 . . 114.7(2) ?
N3 C4 O41 . . 118.3(2) ?
N3 C4 C5 . . 123.9(2) ?
O41 C4 C5 . . 117.8(2) ?
C4 C5 C6 . . 115.0(2) ?
C4 C5 H5 . . 122.5 ?
C6 C5 H5 . . 122.5 ?
N1 C6 O61 . . 118.7(2) ?
N1 C6 C5 . . 123.8(2) ?
O61 C6 C5 . . 117.5(2) ?
C22 N21 C2 . . 131.3(2) ?
C22 N21 H21 . . 114.3 ?
C2 N21 H21 . . 114.3 ?
O22 C22 N21 . . 120.2(2) ?
O22 C22 C23 . . 119.9(2) ?
N21 C22 C23 . . 119.9(2) ?
C24 C23 C22 . . 110.1(2) ?
C24 C23 H23A . . 109.6 ?
C22 C23 H23A . . 109.6 ?
C24 C23 H23B . . 109.6 ?
C22 C23 H23B . . 109.6 ?
H23A C23 H23B . . 108.2 ?
N25 C24 C23 . . 178.9(3) ?
C4 O41 C41 . . 117.40(19) ?
O41 C41 H41A . . 109.5 ?
O41 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
O41 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C6 O61 C61 . . 116.72(19) ?
O61 C61 H61A . . 109.5 ?
O61 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
O61 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 109.5 ?
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 C6 . 1.322(3) ?
N1 C2 . 1.326(3) ?
C2 N3 . 1.322(3) ?
C2 N21 . 1.389(3) ?
N3 C4 . 1.328(3) ?
C4 O41 . 1.337(3) ?
C4 C5 . 1.369(3) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9500 ?
C6 O61 . 1.338(3) ?
N21 C22 . 1.349(3) ?
N21 H21 . 0.8800 ?
C22 O22 . 1.222(3) ?
C22 C23 . 1.508(3) ?
C23 C24 . 1.449(4) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 N25 . 1.135(3) ?
O41 C41 . 1.434(3) ?
C41 H41A . 0.9800 ?
C41 H41B . 0.9800 ?
C41 H41C . 0.9800 ?
O61 C61 . 1.437(3) ?
C61 H61A . 0.9800 ?
C61 H61B . 0.9800 ?
C61 H61C . 0.9800 ?
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
N21 H21 O22 2_566 0.88 1.97 2.845(3) 174 y
C5 H5 O41 2_755 0.95 2.48 3.401(3) 164 y
C23 H23B O22 1_655 0.99 2.58 3.372(3) 137 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N3 . . . . 0.2(4) ?
C6 N1 C2 N21 . . . . -177.6(2) ?
N1 C2 N3 C4 . . . . -0.6(4) ?
N21 C2 N3 C4 . . . . 177.0(2) ?
C2 N3 C4 O41 . . . . -179.2(2) ?
C2 N3 C4 C5 . . . . 1.0(3) ?
N3 C4 C5 C6 . . . . -0.8(4) ?
O41 C4 C5 C6 . . . . 179.4(2) ?
C2 N1 C6 O61 . . . . 178.9(2) ?
C2 N1 C6 C5 . . . . 0.0(3) ?
C4 C5 C6 N1 . . . . 0.3(4) ?
C4 C5 C6 O61 . . . . -178.6(2) ?
N3 C2 N21 C22 . . . . 4.1(4) ?
N1 C2 N21 C22 . . . . -178.0(2) y
C2 N21 C22 O22 . . . . -172.6(2) y
C2 N21 C22 C23 . . . . 9.4(4) y
O22 C22 C23 C24 . . . . 3.0(3) ?
N21 C22 C23 C24 . . . . -179.0(2) y
N3 C4 O41 C41 . . . . 7.5(3) y
C5 C4 O41 C41 . . . . -172.7(2) ?
N1 C6 O61 C61 . . . . 4.0(3) y
C5 C6 O61 C61 . . . . -177.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 27804849
