#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230585.cif $
#------------------------------------------------------------------------------
#
# 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_2230585
loop_
_publ_author_name
'Lu, Chun-Hsiang'
'Wu, Chia-Jun'
'Yeh, Chun-Wei'
'Hu, Hui-Ling'
'Chen, Jhy-Der'
_publ_section_title
;
 Methyl 4-[(pyrimidin-2-yl)carbamoyl]benzoate
;
_journal_coeditor_code           BT5561
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1858
_journal_paper_doi               10.1107/S1600536811025190
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H11 N3 O3'
_chemical_formula_moiety         'C13 H11 N3 O3'
_chemical_formula_sum            'C13 H11 N3 O3'
_chemical_formula_weight         257.25
_chemical_name_systematic
;
Methyl 4-[(pyrimidin-2-yl)carbamoyl]benzoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.793(12)
_cell_angle_beta                 79.997(11)
_cell_angle_gamma                77.426(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7387(7)
_cell_length_b                   7.9037(10)
_cell_length_c                   13.6496(19)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.37
_cell_measurement_theta_min      4.44
_cell_volume                     590.24(14)
_computing_cell_refinement       'XSCANS (Siemens, 1995)'
_computing_data_collection       'XSCANS (Siemens, 1995)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2727
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.2307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                1427
_reflns_number_total             2066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5561.cif
_cod_data_source_block           I
_cod_original_cell_volume        590.24(13)
_cod_database_code               2230585
_cod_database_fobs_code          2230585
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3108(4) 0.2690(3) 1.01131(16) 0.0434(5) Uani d . 1 1 . .
C C2 0.4585(5) 0.1585(3) 1.15496(18) 0.0526(6) Uani d . 1 1 . .
H H2A 0.5531 0.1622 1.2032 0.063 Uiso calc R 1 1 . .
C C3 0.3398(5) 0.0224(3) 1.16664(19) 0.0556(7) Uani d . 1 1 . .
H H3A 0.3510 -0.0647 1.2211 0.067 Uiso calc R 1 1 . .
C C4 0.2038(5) 0.0214(3) 1.09384(19) 0.0569(7) Uani d . 1 1 . .
H H4A 0.1188 -0.0682 1.0999 0.068 Uiso calc R 1 1 . .
C C5 0.1708(4) 0.4275(3) 0.85404(17) 0.0441(5) Uani d . 1 1 . .
C C6 0.2691(4) 0.5254(3) 0.75767(16) 0.0410(5) Uani d . 1 1 . .
C C7 0.5130(4) 0.4939(3) 0.71956(17) 0.0448(6) Uani d . 1 1 . .
H H7A 0.6229 0.4185 0.7570 0.054 Uiso calc R 1 1 . .
C C8 0.5926(4) 0.5745(3) 0.62600(17) 0.0449(6) Uani d . 1 1 . .
H H8A 0.7555 0.5503 0.6000 0.054 Uiso calc R 1 1 . .
C C9 0.4323(4) 0.6908(3) 0.57060(16) 0.0426(5) Uani d . 1 1 . .
C C10 0.1888(4) 0.7234(3) 0.60887(18) 0.0493(6) Uani d . 1 1 . .
H H10A 0.0797 0.8015 0.5722 0.059 Uiso calc R 1 1 . .
C C11 0.1086(4) 0.6399(3) 0.70134(17) 0.0474(6) Uani d . 1 1 . .
H H11A -0.0552 0.6608 0.7261 0.057 Uiso calc R 1 1 . .
C C12 0.5146(4) 0.7860(3) 0.47167(17) 0.0473(6) Uani d . 1 1 . .
C C13 0.8539(5) 0.8302(4) 0.35163(19) 0.0626(7) Uani d . 1 1 . .
H H13A 1.0257 0.8119 0.3490 0.094 Uiso calc R 1 1 . .
H H13B 0.7869 0.9530 0.3485 0.094 Uiso calc R 1 1 . .
H H13C 0.8174 0.7856 0.2959 0.094 Uiso calc R 1 1 . .
N N1 0.4459(3) 0.2859(2) 1.07831(14) 0.0469(5) Uani d . 1 1 . .
N N2 0.1882(4) 0.1440(3) 1.01460(15) 0.0558(6) Uani d . 1 1 . .
N N3 0.3151(4) 0.3953(3) 0.92751(14) 0.0496(5) Uani d . 1 1 . .
H H3B 0.4202 0.4605 0.9213 0.059 Uiso calc R 1 1 . .
O O1 -0.0197(3) 0.3799(2) 0.86197(13) 0.0601(5) Uani d . 1 1 . .
O O2 0.7514(3) 0.7402(2) 0.44414(12) 0.0576(5) Uani d . 1 1 . .
O O3 0.3845(3) 0.8936(3) 0.42251(14) 0.0690(6) Uani d . 1 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
N2 C1 N1 . . 127.4(2) ?
N2 C1 N3 . . 118.7(2) ?
N1 C1 N3 . . 113.84(19) ?
N1 C2 C3 . . 123.5(2) ?
N1 C2 H2A . . 118.3 ?
C3 C2 H2A . . 118.3 ?
C4 C3 C2 . . 116.4(2) ?
C4 C3 H3A . . 121.8 ?
C2 C3 H3A . . 121.8 ?
N2 C4 C3 . . 122.6(2) ?
N2 C4 H4A . . 118.7 ?
C3 C4 H4A . . 118.7 ?
O1 C5 N3 . . 124.8(2) ?
O1 C5 C6 . . 120.6(2) ?
N3 C5 C6 . . 114.57(19) ?
C11 C6 C7 . . 119.2(2) ?
C11 C6 C5 . . 118.7(2) ?
C7 C6 C5 . . 121.9(2) ?
C8 C7 C6 . . 120.0(2) ?
C8 C7 H7A . . 120.0 ?
C6 C7 H7A . . 120.0 ?
C7 C8 C9 . . 120.6(2) ?
C7 C8 H8A . . 119.7 ?
C9 C8 H8A . . 119.7 ?
C8 C9 C10 . . 119.4(2) ?
C8 C9 C12 . . 121.8(2) ?
C10 C9 C12 . . 118.8(2) ?
C11 C10 C9 . . 120.0(2) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C10 C11 C6 . . 120.8(2) ?
C10 C11 H11A . . 119.6 ?
C6 C11 H11A . . 119.6 ?
O3 C12 O2 . . 123.4(2) ?
O3 C12 C9 . . 124.5(2) ?
O2 C12 C9 . . 112.1(2) ?
O2 C13 H13A . . 109.5 ?
O2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C2 N1 C1 . . 114.5(2) ?
C1 N2 C4 . . 115.6(2) ?
C5 N3 C1 . . 127.31(19) ?
C5 N3 H3B . . 116.3 ?
C1 N3 H3B . . 116.3 ?
C12 O2 C13 . . 117.09(19) ?
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
C1 N2 . 1.323(3) ?
C1 N1 . 1.336(3) ?
C1 N3 . 1.393(3) ?
C2 N1 . 1.331(3) ?
C2 C3 . 1.369(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.368(4) ?
C3 H3A . 0.9300 ?
C4 N2 . 1.333(3) ?
C4 H4A . 0.9300 ?
C5 O1 . 1.213(3) ?
C5 N3 . 1.368(3) ?
C5 C6 . 1.501(3) ?
C6 C11 . 1.385(3) ?
C6 C7 . 1.389(3) ?
C7 C8 . 1.382(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.384(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.387(3) ?
C9 C12 . 1.490(3) ?
C10 C11 . 1.380(3) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C12 O3 . 1.202(3) ?
C12 O2 . 1.331(3) ?
C13 O2 . 1.443(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N3 H3B . 0.8600 ?
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
N3 H3B N1 2_667 0.860 2.299 3.104(3) 156
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29436166
