#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237899.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_2237899
loop_
_publ_author_name
'Jiang, Yufei'
'Wu, Kong'
'Cui, Dongmei'
'Zhou, Wei'
_publ_section_title
;
 2-Chloro-5-fluoro-6-methyl-N-o-tolylpyrimidin-4-amine
;
_journal_coeditor_code           IS5256
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o626
_journal_paper_doi               10.1107/S160053681300812X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H11 Cl F N3'
_chemical_formula_moiety         'C12 H11 Cl F N3'
_chemical_formula_sum            'C12 H11 Cl F N3'
_chemical_formula_weight         251.69
_chemical_name_systematic
;
2-Chloro-5-fluoro-6-methyl-N-o-tolylpyrimidin-4-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 113.021(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0593(7)
_cell_length_b                   8.3684(4)
_cell_length_c                   12.8611(6)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1364
_cell_measurement_theta_min      2.9750
_cell_volume                     1194.54(12)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4692
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.2577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1750
_reflns_number_total             2125
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5256.cif
_cod_data_source_block           I
_cod_original_cell_volume        1194.54(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237899
_cod_database_fobs_code          2237899
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 Cl1 0.75856(5) -0.06428(7) 1.24493(4) 0.0666(2) Uani d . 1 1
N N2 0.57335(12) 0.12020(18) 1.15433(11) 0.0470(4) Uani d . 1 1
N N3 0.70666(11) 0.09036(16) 1.05829(11) 0.0407(3) Uani d . 1 1
F F1 0.46632(9) 0.35255(15) 0.89928(9) 0.0694(3) Uani d . 1 1
C C1 0.66841(15) 0.0648(2) 1.14005(14) 0.0426(4) Uani d . 1 1
C C4 0.63837(14) 0.1897(2) 0.97700(13) 0.0401(4) Uani d . 1 1
C C3 0.53397(14) 0.2537(2) 0.98347(14) 0.0448(4) Uani d . 1 1
N N1 0.66996(12) 0.22514(18) 0.89014(11) 0.0484(4) Uani d . 1 1
H H1 0.6236 0.2882 0.8387 0.058 Uiso calc R 1 1
C C2 0.50232(14) 0.2189(2) 1.07122(15) 0.0460(4) Uani d . 1 1
C C6 0.77521(15) 0.1655(2) 0.87727(13) 0.0445(4) Uani d . 1 1
C C11 0.7589(2) 0.0547(2) 0.79274(17) 0.0627(5) Uani d . 1 1
H H11 0.6821 0.0171 0.7491 0.075 Uiso calc R 1 1
C C5 0.39149(18) 0.2840(3) 1.08108(19) 0.0684(6) Uani d . 1 1
H H5A 0.3501 0.3528 1.0180 0.103 Uiso calc R 1 1
H H5B 0.4136 0.3437 1.1500 0.103 Uiso calc R 1 1
H H5C 0.3395 0.1974 1.0816 0.103 Uiso calc R 1 1
C C10 0.8577(3) 0.0005(3) 0.7736(2) 0.0862(8) Uani d . 1 1
H H10 0.8482 -0.0745 0.7174 0.103 Uiso calc R 1 1
C C8 0.98515(19) 0.1680(4) 0.9222(2) 0.0824(8) Uani d . 1 1
H H8 1.0622 0.2052 0.9653 0.099 Uiso calc R 1 1
C C9 0.9696(3) 0.0584(4) 0.8384(3) 0.0925(9) Uani d . 1 1
H H9 1.0361 0.0229 0.8254 0.111 Uiso calc R 1 1
C C7 0.88790(16) 0.2248(2) 0.94391(16) 0.0560(5) Uani d . 1 1
C C12 0.9052(2) 0.3424(3) 1.03578(19) 0.0804(7) Uani d . 1 1
H H12A 0.8506 0.4302 1.0065 0.121 Uiso calc R 1 1
H H12B 0.9866 0.3812 1.0645 0.121 Uiso calc R 1 1
H H12C 0.8896 0.2916 1.0956 0.121 Uiso calc R 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'
F F 0.0171 0.0103 '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
C1 N2 C2 114.88(14)
C1 N3 C4 115.01(14)
N2 C1 N3 130.53(16)
N2 C1 Cl1 115.19(12)
N3 C1 Cl1 114.28(12)
N3 C4 N1 119.86(14)
N3 C4 C3 118.98(14)
N1 C4 C3 121.15(15)
F1 C3 C2 121.27(15)
F1 C3 C4 117.46(14)
C2 C3 C4 121.27(16)
C4 N1 C6 124.73(14)
C4 N1 H1 117.6
C6 N1 H1 117.6
N2 C2 C3 119.31(15)
N2 C2 C5 117.72(16)
C3 C2 C5 122.97(17)
C11 C6 C7 122.05(17)
C11 C6 N1 117.67(16)
C7 C6 N1 120.19(16)
C6 C11 C10 119.4(2)
C6 C11 H11 120.3
C10 C11 H11 120.3
C2 C5 H5A 109.5
C2 C5 H5B 109.5
H5A C5 H5B 109.5
C2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C9 C10 C11 119.3(2)
C9 C10 H10 120.4
C11 C10 H10 120.4
C9 C8 C7 121.3(2)
C9 C8 H8 119.3
C7 C8 H8 119.3
C10 C9 C8 121.0(2)
C10 C9 H9 119.5
C8 C9 H9 119.5
C6 C7 C8 117.0(2)
C6 C7 C12 121.83(17)
C8 C7 C12 121.2(2)
C7 C12 H12A 109.5
C7 C12 H12B 109.5
H12A C12 H12B 109.5
C7 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7384(17)
N2 C1 1.314(2)
N2 C2 1.357(2)
N3 C1 1.321(2)
N3 C4 1.337(2)
F1 C3 1.3533(19)
C4 N1 1.347(2)
C4 C3 1.400(2)
C3 C2 1.357(2)
N1 C6 1.433(2)
N1 H1 0.8600
C2 C5 1.494(2)
C6 C11 1.383(3)
C6 C7 1.385(2)
C11 C10 1.384(3)
C11 H11 0.9300
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C10 C9 1.367(4)
C10 H10 0.9300
C8 C9 1.371(4)
C8 C7 1.391(3)
C8 H8 0.9300
C9 H9 0.9300
C7 C12 1.488(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 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
N1 H1 N2 4_565 0.86 2.34 3.0768(19) 145
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
C2 N2 C1 N3 0.5(3)
C2 N2 C1 Cl1 -178.98(11)
C4 N3 C1 N2 0.6(3)
C4 N3 C1 Cl1 -179.90(11)
C1 N3 C4 N1 179.34(15)
C1 N3 C4 C3 -1.3(2)
N3 C4 C3 F1 -179.39(14)
N1 C4 C3 F1 -0.1(2)
N3 C4 C3 C2 1.1(2)
N1 C4 C3 C2 -179.61(16)
N3 C4 N1 C6 -0.9(3)
C3 C4 N1 C6 179.75(16)
C1 N2 C2 C3 -0.8(2)
C1 N2 C2 C5 178.99(16)
F1 C3 C2 N2 -179.44(14)
C4 C3 C2 N2 0.1(3)
F1 C3 C2 C5 0.8(3)
C4 C3 C2 C5 -179.72(17)
C4 N1 C6 C11 109.29(19)
C4 N1 C6 C7 -74.2(2)
C7 C6 C11 C10 0.2(3)
N1 C6 C11 C10 176.61(17)
C6 C11 C10 C9 -0.5(3)
C11 C10 C9 C8 0.6(4)
C7 C8 C9 C10 -0.4(4)
C11 C6 C7 C8 0.0(3)
N1 C6 C7 C8 -176.33(16)
C11 C6 C7 C12 -179.19(18)
N1 C6 C7 C12 4.5(3)
C9 C8 C7 C6 0.1(3)
C9 C8 C7 C12 179.3(2)
