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#$Date: 2016-01-22 05:52:52 +0200 (Fri, 22 Jan 2016) $
#$Revision: 174731 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/14/2241482.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_2241482
loop_
_publ_author_name
'Medjani, Meriem'
'Hamdouni, Noudjoud'
'Brihi, Ouarda'
'Boudjada, Ali'
'Meinnel, Jean'
_publ_section_title
;
 Crystal structure of 4,6-dichloro-5-methylpyrimidine
;
_journal_coeditor_code           SU5261
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1073
_journal_page_last               o1074
_journal_paper_doi               10.1107/S2056989015024020
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 H4 Cl2 N2'
_chemical_formula_moiety         'C5 H4 Cl2 N2'
_chemical_formula_sum            'C5 H4 Cl2 N2'
_chemical_formula_weight         163.00
_chemical_name_systematic
;
4,6-Dichloro-5-methylpyrimidine
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.233(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.463(5)
_cell_length_b                   7.827(5)
_cell_length_c                   11.790(5)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      4.24
_cell_volume                     687.6(7)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL-2014/6 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL-2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'CCD rotation images, thin slices ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2347
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_min         3.125
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Crysalis PRO; Oxford Diffraction, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0679
_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)+(0.0729P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                791
_reflns_number_total             1228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5261sup1.cif
_cod_data_source_block           I
_cod_database_code               2241482
_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   0.920
_shelx_estimated_absorpt_t_max   0.935
_shelxl_version_number           2014/6
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_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_occupancy
Cl Cl14 0.47393(16) 0.21816(17) 0.57181(8) 0.0686(5) Uani d 1
Cl Cl16 0.45631(17) 0.4430(2) 0.13763(9) 0.0853(6) Uani d 1
N N1 0.2066(5) 0.4832(6) 0.2775(3) 0.0604(11) Uani d 1
N N3 0.2153(5) 0.3882(5) 0.4695(3) 0.0579(10) Uani d 1
C C2 0.1383(6) 0.4657(7) 0.3784(4) 0.0661(14) Uani d 1
H H2 0.0251 0.5123 0.3865 0.079 Uiso calc 1
C C4 0.3744(5) 0.3225(5) 0.4544(3) 0.0458(10) Uani d 1
C C5 0.4659(5) 0.3309(6) 0.3546(3) 0.0458(10) Uani d 1
C C6 0.3650(6) 0.4175(6) 0.2685(3) 0.0514(11) Uani d 1
C C51 0.6464(6) 0.2553(7) 0.3426(4) 0.0666(14) Uani d 1
H H51A 0.7041 0.3121 0.2823 0.100 Uiso calc 1
H H51B 0.6344 0.1359 0.3252 0.100 Uiso calc 1
H H51C 0.7175 0.2692 0.4124 0.100 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N1 C2 115.4(3)
C4 N3 C2 114.8(3)
N1 C2 N3 126.8(4)
N1 C2 H2 116.6
N3 C2 H2 116.6
N3 C4 C5 125.7(4)
N3 C4 Cl14 115.1(3)
C5 C4 Cl14 119.2(3)
C4 C5 C6 111.4(4)
C4 C5 C51 123.4(4)
C6 C5 C51 125.2(4)
N1 C6 C5 125.9(3)
N1 C6 Cl16 115.6(3)
C5 C6 Cl16 118.5(3)
C5 C51 H51A 109.5
C5 C51 H51B 109.5
H51A C51 H51B 109.5
C5 C51 H51C 109.5
H51A C51 H51C 109.5
H51B C51 H51C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl14 C4 1.737(4)
Cl16 C6 1.733(4)
N1 C6 1.299(6)
N1 C2 1.327(5)
N3 C4 1.315(5)
N3 C2 1.335(5)
C2 H2 0.9300
C4 C5 1.395(5)
C5 C6 1.403(6)
C5 C51 1.486(6)
C51 H51A 0.9600
C51 H51B 0.9600
C51 H51C 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
C2 H2 N3 3_566 0.93 2.66 3.468(6) 146
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
C6 N1 C2 N3 -0.2(8)
C4 N3 C2 N1 -0.7(8)
C2 N3 C4 C5 1.3(7)
C2 N3 C4 Cl14 -178.9(4)
N3 C4 C5 C6 -1.1(6)
Cl14 C4 C5 C6 179.2(3)
N3 C4 C5 C51 179.5(4)
Cl14 C4 C5 C51 -0.2(6)
C2 N1 C6 C5 0.5(8)
C2 N1 C6 Cl16 -179.0(4)
C4 C5 C6 N1 0.1(7)
C51 C5 C6 N1 179.5(5)
C4 C5 C6 Cl16 179.6(3)
C51 C5 C6 Cl16 -1.0(7)

_cod_database_fobs_code 2241482
