#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239775.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_2239775
loop_
_publ_author_name
'Wu, Ya-Ming'
_publ_section_title
;
 Methyl 4-amino-2-chloropyrimidine-5-carboxylate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o869
_journal_paper_doi               10.1107/S1600536814016080
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H6 Cl N3 O2'
_chemical_formula_moiety         'C6 H6 Cl N3 O2'
_chemical_formula_sum            'C6 H6 Cl N3 O2'
_chemical_formula_weight         187.59
_chemical_melting_point          433
_chemical_name_systematic
;
Methyl 4-amino-2-chloropyrimidine-5-carboxylate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.71(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.9110(8)
_cell_length_b                   10.136(2)
_cell_length_c                   9.848(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     385.89(14)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1474
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.361
_refine_ls_abs_structure_details 'Flack (1983), 106 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         817
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0461
_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)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                673
_reflns_number_total             817
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5799sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        385.89(13)
_cod_original_sg_symbol_Hall     'p -2yc'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2239775
_cod_database_fobs_code          2239775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
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
Cl Cl 1.0210(5) -0.25325(18) 0.5060(2) 0.0602(4) Uani d . 1 1
O O1 0.6389(12) 0.3421(3) 0.3059(4) 0.0559(11) Uani d . 1 1
C C1 1.1205(14) 0.1186(6) 0.5586(5) 0.0363(14) Uani d . 1 1
N N1 1.1550(12) -0.0104(6) 0.5759(4) 0.0411(11) Uani d . 1 1
O O2 0.9976(15) 0.3988(3) 0.4968(5) 0.0597(12) Uani d . 1 1
C C2 0.9749(16) -0.0851(5) 0.4819(5) 0.0399(13) Uani d . 1 1
N N2 0.7645(13) -0.0485(4) 0.3675(5) 0.0423(12) Uani d . 1 1
N N3 1.3017(15) 0.1949(5) 0.6544(5) 0.0480(12) Uani d . 1 1
H H3A 1.4322 0.1594 0.7229 0.058 Uiso calc R 1 1
H H3B 1.2878 0.2793 0.6476 0.058 Uiso calc R 1 1
C C3 0.7362(14) 0.0804(4) 0.3525(5) 0.0381(13) Uani d . 1 1
H H3C 0.5923 0.1118 0.2754 0.046 Uiso calc R 1 1
C C4 0.9020(14) 0.1715(5) 0.4414(5) 0.0339(12) Uani d . 1 1
C C5 0.8591(15) 0.3139(6) 0.4214(6) 0.0409(13) Uani d . 1 1
C C6 0.576(2) 0.4789(6) 0.2751(8) 0.0626(18) Uani d . 1 1
H H6A 0.4174 0.4871 0.1911 0.094 Uiso calc R 1 1
H H6B 0.7904 0.5215 0.2650 0.094 Uiso calc R 1 1
H H6C 0.4795 0.5199 0.3485 0.094 Uiso calc R 1 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
Cl 0.0703(9) 0.0469(7) 0.0553(8) -0.0003(8) -0.0160(6) 0.0032(7)
O1 0.067(3) 0.051(2) 0.040(2) 0.008(2) -0.023(2) 0.000(2)
C1 0.031(3) 0.046(3) 0.029(3) -0.002(3) -0.006(2) -0.003(2)
N1 0.041(3) 0.052(3) 0.026(2) 0.002(2) -0.008(2) 0.000(2)
O2 0.070(3) 0.046(2) 0.053(2) -0.008(3) -0.023(2) -0.007(2)
C2 0.039(3) 0.050(3) 0.030(3) 0.003(3) 0.002(3) -0.003(2)
N2 0.041(3) 0.051(3) 0.031(2) -0.003(2) -0.008(2) -0.003(2)
N3 0.057(3) 0.049(2) 0.031(2) -0.004(3) -0.016(2) -0.004(2)
C3 0.039(3) 0.046(3) 0.026(3) 0.001(3) -0.006(2) -0.003(3)
C4 0.032(3) 0.040(3) 0.028(3) 0.006(2) -0.003(2) 0.006(2)
C5 0.040(3) 0.048(3) 0.032(3) 0.004(3) -0.005(2) 0.004(2)
C6 0.060(4) 0.051(3) 0.067(4) 0.008(3) -0.023(3) 0.012(3)
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O1 C6 116.7(5)
N1 C1 N3 116.6(5)
N1 C1 C4 120.7(5)
N3 C1 C4 122.7(5)
C2 N1 C1 116.4(5)
N1 C2 N2 128.8(5)
N1 C2 Cl 116.0(4)
N2 C2 Cl 115.2(4)
C3 N2 C2 113.5(5)
C1 N3 H3A 120.0
C1 N3 H3B 120.0
H3A N3 H3B 120.0
N2 C3 C4 125.0(5)
N2 C3 H3C 117.5
C4 C3 H3C 117.5
C3 C4 C1 115.5(4)
C3 C4 C5 123.1(4)
C1 C4 C5 121.3(4)
O2 C5 O1 122.4(5)
O2 C5 C4 126.0(5)
O1 C5 C4 111.6(4)
O1 C6 H6A 109.5
O1 C6 H6B 109.5
H6A C6 H6B 109.5
O1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C2 1.726(5)
O1 C5 1.350(7)
O1 C6 1.433(7)
C1 N1 1.324(8)
C1 N3 1.337(7)
C1 C4 1.432(7)
N1 C2 1.315(7)
O2 C5 1.210(7)
C2 N2 1.343(8)
N2 C3 1.318(6)
N3 H3A 0.8600
N3 H3B 0.8600
C3 C4 1.367(7)
C3 H3C 0.9300
C4 C5 1.464(7)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
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
N3 H3A N2 2_655 0.86 2.10 2.955(7) 171 yes
N3 H3B O2 . 0.86 2.11 2.745(7) 130 yes
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
N3 C1 N1 C2 179.6(6)
C4 C1 N1 C2 -1.1(9)
C1 N1 C2 N2 1.9(10)
C1 N1 C2 Cl -179.8(4)
N1 C2 N2 C3 -1.5(10)
Cl C2 N2 C3 -179.9(5)
C2 N2 C3 C4 0.5(8)
N2 C3 C4 C1 0.0(8)
N2 C3 C4 C5 -179.2(6)
N1 C1 C4 C3 0.4(8)
N3 C1 C4 C3 179.6(6)
N1 C1 C4 C5 179.5(5)
N3 C1 C4 C5 -1.3(8)
C6 O1 C5 O2 0.4(10)
C6 O1 C5 C4 -179.9(6)
C3 C4 C5 O2 179.7(7)
C1 C4 C5 O2 0.6(9)
C3 C4 C5 O1 0.0(8)
C1 C4 C5 O1 -179.1(6)
