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#$Date: 2022-05-18 12:36:03 +0300 (Wed, 18 May 2022) $
#$Revision: 275519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105296.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_8105296
loop_
_publ_author_name
'Yan, Sheng'
'Xue, Mei'
'He, Xinyuan'
'Wang, Chengqian'
'Wang, Zixin'
'Wang, Jianlong'
_publ_section_title
;
 The crystal structure of 5-chloro-4,6-dimethoxypyrimidin-2-amine,
 C6H8ClN3O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              815
_journal_page_last               816
_journal_paper_doi               10.1515/ncrs-2020-0026
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C6 H8 Cl N3 O2'
_chemical_formula_weight         189.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.060(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.066(3)
_cell_length_b                   12.775(8)
_cell_length_c                   12.587(8)
_cell_measurement_reflns_used    602
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.97
_cell_measurement_theta_min      3.19
_cell_volume                     812.6(9)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4854
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.386
_diffrn_reflns_theta_min         2.274
_exptl_absorpt_coefficient_mu    0.431
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       rod
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0597
_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/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1990
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                965
_reflns_number_total             1823
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0026_suppl.cif
_cod_data_source_block           1909194_0m
_cod_original_cell_volume        812.5(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105296
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_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_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1897(2) 0.34398(8) 0.79001(9) 0.0537(4) Uani 1 1 d . . . . .
O1 O 0.2141(5) 0.2033(2) 0.6081(2) 0.0493(8) Uani 1 1 d . . . . .
O2 O 0.5749(5) 0.5083(2) 0.7582(2) 0.0458(7) Uani 1 1 d . . . . .
N2 N 0.5312(6) 0.2924(2) 0.5216(2) 0.0371(8) Uani 1 1 d . . . . .
N3 N 0.7199(5) 0.4496(2) 0.5985(2) 0.0356(7) Uani 1 1 d . . . . .
N6 N 0.8465(7) 0.3827(3) 0.4402(3) 0.0478(9) Uani 1 1 d . . . . .
H6A H 0.835292 0.336295 0.390549 0.057 Uiso 1 1 calc R U . . .
H6B H 0.955266 0.434073 0.436820 0.057 Uiso 1 1 calc R U . . .
C1 C 0.3819(7) 0.2849(3) 0.6027(3) 0.0376(9) Uani 1 1 d . . . . .
C2 C 0.3869(7) 0.3561(3) 0.6852(3) 0.0357(9) Uani 1 1 d . . . . .
C3 C 0.5640(7) 0.4385(3) 0.6785(3) 0.0367(9) Uani 1 1 d . . . . .
C4 C 0.7498(8) 0.5960(3) 0.7512(3) 0.0529(12) Uani 1 1 d . . . . .
H4A H 0.928861 0.571440 0.750713 0.079 Uiso 1 1 calc R U . . .
H4B H 0.733851 0.641145 0.811325 0.079 Uiso 1 1 calc R U . . .
H4C H 0.703822 0.634026 0.686718 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2104(10) 0.1284(4) 0.5248(4) 0.0702(15) Uani 1 1 d . . . . .
H5A H 0.173189 0.162797 0.457624 0.105 Uiso 1 1 calc R U . . .
H5B H 0.075883 0.077124 0.535007 0.105 Uiso 1 1 calc R U . . .
H5C H 0.379641 0.094449 0.525401 0.105 Uiso 1 1 calc R U . . .
C6 C 0.6941(7) 0.3748(3) 0.5231(3) 0.0362(9) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 C5 117.3(3) . .
C3 O2 C4 117.8(3) . .
C1 N2 C6 115.7(3) . .
C3 N3 C6 115.1(3) . .
C6 N6 H6A 120.0 . .
C6 N6 H6B 120.0 . .
H6A N6 H6B 120.0 . .
N2 C1 O1 119.6(3) . .
N2 C1 C2 123.7(3) . .
O1 C1 C2 116.7(4) . .
C1 C2 C3 115.5(4) . .
C1 C2 Cl1 122.6(3) . .
C3 C2 Cl1 121.9(3) . .
N3 C3 O2 120.0(3) . .
N3 C3 C2 123.2(3) . .
O2 C3 C2 116.8(4) . .
O2 C4 H4A 109.5 . .
O2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
O2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C5 H5A 109.5 . .
O1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
O1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N2 C6 N6 115.8(3) . .
N2 C6 N3 126.7(3) . .
N6 C6 N3 117.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.717(4) .
O1 C1 1.351(4) .
O1 C5 1.419(5) .
O2 C3 1.341(4) .
O2 C4 1.435(5) .
N2 C1 1.316(5) .
N2 C6 1.337(5) .
N3 C3 1.330(4) .
N3 C6 1.347(4) .
N6 C6 1.345(5) .
N6 H6A 0.8600 .
N6 H6B 0.8600 .
C1 C2 1.379(5) .
C2 C3 1.390(5) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N2 C1 O1 -179.1(3) . . . .
C6 N2 C1 C2 0.2(5) . . . .
C5 O1 C1 N2 0.6(5) . . . .
C5 O1 C1 C2 -178.8(4) . . . .
N2 C1 C2 C3 -0.3(5) . . . .
O1 C1 C2 C3 179.1(3) . . . .
N2 C1 C2 Cl1 -179.9(3) . . . .
O1 C1 C2 Cl1 -0.6(5) . . . .
C6 N3 C3 O2 179.6(3) . . . .
C6 N3 C3 C2 0.2(5) . . . .
C4 O2 C3 N3 2.6(5) . . . .
C4 O2 C3 C2 -177.9(3) . . . .
C1 C2 C3 N3 0.1(5) . . . .
Cl1 C2 C3 N3 179.7(3) . . . .
C1 C2 C3 O2 -179.4(3) . . . .
Cl1 C2 C3 O2 0.3(5) . . . .
C1 N2 C6 N6 -179.9(3) . . . .
C1 N2 C6 N3 0.1(5) . . . .
C3 N3 C6 N2 -0.3(5) . . . .
C3 N3 C6 N6 179.7(3) . . . .
