#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222064.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_2222064
loop_
_publ_author_name
'Chen, Yan'
'Fang, Zheng'
'Wei, Ping'
_publ_section_title
;
 2,4-Dichloropyrimidine
;
_journal_coeditor_code           HK2698
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1438
_journal_paper_doi               10.1107/S1600536809019667
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H2 Cl2 N2'
_chemical_formula_moiety         'C4 H2 Cl2 N2'
_chemical_formula_sum            'C4 H2 Cl2 N2'
_chemical_formula_weight         148.98
_chemical_name_systematic
;
2,4-Dichloropyrimidine
;
_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                 92.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5090(15)
_cell_length_b                   10.776(2)
_cell_length_c                   7.1980(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     581.7(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0844
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1223
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  0.8263
_exptl_absorpt_correction_T_min  0.7551
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0692
_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)+(0.07P)²+1.45P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                733
_reflns_number_total             1139
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2698.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222064
_cod_database_fobs_code          2222064
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.5768(2) 0.63809(14) 0.0975(2) 0.0762(6) Uani d . 1 . .
Cl Cl2 1.1679(2) 0.83010(16) 0.3510(3) 0.0862(7) Uani d . 1 . .
N N1 0.6273(6) 0.8744(4) 0.0912(7) 0.0612(12) Uani d . 1 . .
N N2 0.8628(5) 0.7492(4) 0.2211(6) 0.0555(11) Uani d . 1 . .
C C1 0.8975(7) 0.9681(5) 0.2072(8) 0.0652(15) Uani d . 1 . .
H H1B 0.9665 1.0384 0.2321 0.078 Uiso calc R 1 . .
C C2 0.7272(8) 0.9751(5) 0.1252(9) 0.0689(16) Uani d . 1 . .
H H2B 0.6808 1.0526 0.0927 0.083 Uiso calc R 1 . .
C C3 0.7027(6) 0.7699(5) 0.1403(7) 0.0485(12) Uani d . 1 . .
C C4 0.9577(7) 0.8520(5) 0.2490(8) 0.0562(14) Uani d . 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
Cl1 0.0693(9) 0.0670(10) 0.0897(12) -0.0184(7) -0.0222(8) -0.0065(8)
Cl2 0.0581(9) 0.0731(11) 0.1233(15) -0.0074(7) -0.0370(9) -0.0038(10)
N1 0.055(3) 0.059(3) 0.068(3) 0.013(2) -0.009(2) 0.002(2)
N2 0.052(2) 0.042(2) 0.071(3) -0.0014(18) -0.017(2) -0.002(2)
C1 0.070(4) 0.042(3) 0.081(4) 0.000(2) -0.013(3) -0.007(3)
C2 0.079(4) 0.047(3) 0.081(4) 0.006(3) 0.000(3) 0.007(3)
C3 0.045(2) 0.056(3) 0.044(3) 0.005(2) -0.006(2) -0.007(2)
C4 0.051(3) 0.052(3) 0.064(3) -0.002(2) -0.008(3) -0.005(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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C2 . . 114.9(5) ?
C4 N2 C3 . . 113.2(4) ?
C4 C1 C2 . . 115.8(5) ?
C4 C1 H1B . . 122.1 ?
C2 C1 H1B . . 122.1 ?
N1 C2 C1 . . 122.2(5) ?
N1 C2 H2B . . 118.9 ?
C1 C2 H2B . . 118.9 ?
N1 C3 N2 . . 129.5(5) ?
N1 C3 Cl1 . . 115.9(4) ?
N2 C3 Cl1 . . 114.6(4) ?
N2 C4 C1 . . 124.4(5) ?
N2 C4 Cl2 . . 115.0(4) ?
C1 C4 Cl2 . . 120.5(4) ?
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
Cl1 C3 . 1.725(5) ?
Cl2 C4 . 1.723(5) ?
N1 C2 . 1.334(7) ?
N1 C3 . 1.302(6) ?
N2 C3 . 1.327(6) ?
N2 C4 . 1.327(6) ?
C1 C2 . 1.383(8) ?
C1 C4 . 1.358(7) ?
C1 H1B . 0.9300 ?
C2 H2B . 0.9300 ?
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
C1 H1B N2 2_755 0.93 2.62 3.548(7) 174
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C2 C1 . . . . -0.2(9) ?
C4 C1 C2 N1 . . . . 0.7(10) ?
C2 N1 C3 N2 . . . . 1.0(9) ?
C2 N1 C3 Cl1 . . . . -179.9(4) ?
C4 N2 C3 N1 . . . . -2.0(9) ?
C4 N2 C3 Cl1 . . . . 178.8(4) ?
C3 N2 C4 C1 . . . . 2.5(9) ?
C3 N2 C4 Cl2 . . . . -179.2(4) ?
C2 C1 C4 N2 . . . . -2.0(10) ?
C2 C1 C4 Cl2 . . . . 179.8(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 69938
