#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220855.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_2220855
loop_
_publ_author_name
'Ma, Wen'
'Li, Hongyan'
_publ_section_title
;
 1,4-Bis(6-chloropyrimidin-4-yloxy)benzene
;
_journal_coeditor_code           LH2746
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o223
_journal_paper_doi               10.1107/S1600536808043511
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H8 Cl2 N4 O2'
_chemical_formula_moiety         'C14 H8 Cl2 N4 O2'
_chemical_formula_sum            'C14 H8 Cl2 N4 O2'
_chemical_formula_weight         335.14
_chemical_name_systematic
;
1,4-Bis(6-chloropyrimidin-4-yloxy)benzene
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 93.301(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0760(5)
_cell_length_b                   6.9693(2)
_cell_length_c                   10.7893(3)
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.77
_cell_volume                     1432.02(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6918
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.249
_refine_ls_extinction_coef       0.0062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0374
_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)+(0.0635P)²+0.2906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                1156
_reflns_number_total             1372
_reflns_threshold_expression     I>2σ(I)'
_cod_data_source_file            lh2746.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2220855
_cod_database_fobs_code          2220855
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
C C1 0.34316(10) 0.0000 0.22381(18) 0.0495(5) Uani d S 1 . .
H H1 0.3002 0.0000 0.1786 0.059 Uiso calc SR 1 . .
C C2 0.40565(11) 0.0000 0.16857(19) 0.0543(6) Uani d S 1 . .
C C3 0.46576(12) 0.0000 0.3504(2) 0.0666(7) Uani d S 1 . .
H H3 0.5089 0.0000 0.3950 0.080 Uiso calc SR 1 . .
C C4 0.34857(11) 0.0000 0.35261(19) 0.0467(5) Uani d S 1 . .
C C5 0.22554(11) 0.0000 0.36269(19) 0.0512(6) Uani d S 1 . .
C C6 0.19419(8) 0.1719(3) 0.33512(14) 0.0589(4) Uani d . 1 . .
H H6 0.2162 0.2867 0.3578 0.071 Uiso calc R 1 . .
C C7 0.12865(9) 0.1712(3) 0.27244(15) 0.0636(5) Uani d . 1 . .
H H7 0.1058 0.2859 0.2523 0.076 Uiso calc R 1 . .
C C8 0.09825(11) 0.0000 0.24084(19) 0.0581(7) Uani d S 1 . .
C C9 -0.02669(11) 0.0000 0.21792(19) 0.0529(6) Uani d S 1 . .
C C10 -0.08588(12) 0.0000 0.1385(2) 0.0570(6) Uani d S 1 . .
H H10 -0.0839 0.0000 0.0526 0.068 Uiso calc SR 1 . .
C C11 -0.14794(11) 0.0000 0.1964(2) 0.0525(5) Uani d S 1 . .
C C12 -0.09188(11) 0.0000 0.3830(2) 0.0553(6) Uani d S 1 . .
H H12 -0.0939 0.0000 0.4689 0.066 Uiso calc SR 1 . .
Cl Cl1 0.40498(4) 0.0000 0.00858(5) 0.0916(3) Uani d S 1 . .
Cl Cl2 -0.22616(3) 0.0000 0.10747(6) 0.0829(3) Uani d S 1 . .
N N1 0.46804(10) 0.0000 0.22748(18) 0.0676(6) Uani d S 1 . .
N N2 0.40951(9) 0.0000 0.41739(17) 0.0572(5) Uani d S 1 . .
N N3 -0.02774(9) 0.0000 0.33990(16) 0.0533(5) Uani d S 1 . .
N N4 -0.15287(9) 0.0000 0.31826(17) 0.0566(5) Uani d S 1 . .
O O1 0.29285(8) 0.0000 0.42430(14) 0.0619(5) Uani d S 1 . .
O O2 0.03558(8) 0.0000 0.16482(14) 0.0793(6) Uani d S 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C4 . . 114.92(19) ?
C2 C1 H1 . . 122.5 ?
C4 C1 H1 . . 122.5 ?
N1 C2 C1 . . 125.3(2) ?
N1 C2 Cl1 . . 115.94(16) ?
C1 C2 Cl1 . . 118.76(17) ?
N2 C3 N1 . . 128.1(2) ?
N2 C3 H3 . . 115.9 ?
N1 C3 H3 . . 115.9 ?
N2 C4 O1 . . 113.24(18) n
N2 C4 C1 . . 122.83(19) ?
O1 C4 C1 . . 123.93(19) n
C6 C5 C6 6 . 122.8(2) ?
C6 C5 O1 6 . 118.57(10) n
C6 C5 O1 . . 118.57(10) n
C5 C6 C7 . . 118.36(17) ?
C5 C6 H6 . . 120.8 ?
C7 C6 H6 . . 120.8 ?
C8 C7 C6 . . 118.97(17) ?
C8 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
C7 C8 C7 6 . 122.4(2) ?
C7 C8 O2 6 . 118.70(11) n
C7 C8 O2 . . 118.70(11) n
N3 C9 O2 . . 119.27(19) n
N3 C9 C10 . . 124.21(19) ?
O2 C9 C10 . . 116.52(19) ?
C11 C10 C9 . . 114.6(2) ?
C11 C10 H10 . . 122.7 ?
C9 C10 H10 . . 122.7 ?
N4 C11 C10 . . 124.4(2) ?
N4 C11 Cl2 . . 116.32(17) ?
C10 C11 Cl2 . . 119.24(18) ?
N4 C12 N3 . . 127.8(2) ?
N4 C12 H12 . . 116.1 ?
N3 C12 H12 . . 116.1 ?
C2 N1 C3 . . 113.6(2) ?
C4 N2 C3 . . 115.20(19) ?
C9 N3 C12 . . 114.53(19) ?
C12 N4 C11 . . 114.45(18) ?
C4 O1 C5 . . 117.07(16) n
C9 O2 C8 . . 119.40(16) n
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
C1 C2 . 1.363(3) ?
C1 C4 . 1.388(3) ?
C1 H1 . 0.9300 ?
C2 N1 . 1.317(3) ?
C2 Cl1 . 1.725(2) ?
C3 N2 . 1.328(3) ?
C3 N1 . 1.329(3) ?
C3 H3 . 0.9300 ?
C4 N2 . 1.322(3) ?
C4 O1 . 1.350(2) n
C5 C6 6 1.364(2) ?
C5 C6 . 1.364(2) ?
C5 O1 . 1.411(3) n
C6 C7 . 1.387(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.361(2) ?
C7 H7 . 0.9300 ?
C8 C7 6 1.361(2) ?
C8 O2 . 1.410(3) n
C9 N3 . 1.317(3) ?
C9 O2 . 1.348(3) n
C9 C10 . 1.377(3) ?
C10 C11 . 1.370(3) ?
C10 H10 . 0.9300 ?
C11 N4 . 1.323(3) ?
C11 Cl2 . 1.727(2) ?
C12 N4 . 1.322(3) ?
C12 N3 . 1.334(3) ?
C12 H12 . 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
C10 H10 O2 2 0.93 2.57 3.463(3) 161.4
C3 H3 N2 2_656 0.93 2.48 3.355(3) 156.6
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
C4 C1 C2 N1 . . . . 0.0 ?
C4 C1 C2 Cl1 . . . . 180.0 ?
C2 C1 C4 N2 . . . . 0.0 ?
C2 C1 C4 O1 . . . . 180.0 ?
C6 C5 C6 C7 6 . . . -2.3(3) ?
O1 C5 C6 C7 . . . . 178.76(14) ?
C5 C6 C7 C8 . . . . -0.1(3) ?
C6 C7 C8 C7 . . . 6 2.4(3) ?
C6 C7 C8 O2 . . . . -172.75(14) ?
N3 C9 C10 C11 . . . . 0.0 ?
O2 C9 C10 C11 . . . . 180.0 ?
C9 C10 C11 N4 . . . . 0.0 ?
C9 C10 C11 Cl2 . . . . 180.0 ?
C1 C2 N1 C3 . . . . 0.0 ?
Cl1 C2 N1 C3 . . . . 180.0 ?
N2 C3 N1 C2 . . . . 0.0 ?
O1 C4 N2 C3 . . . . 180.0 ?
C1 C4 N2 C3 . . . . 0.0 ?
N1 C3 N2 C4 . . . . 0.0 ?
O2 C9 N3 C12 . . . . 180.0 ?
C10 C9 N3 C12 . . . . 0.0 ?
N4 C12 N3 C9 . . . . 0.0 ?
N3 C12 N4 C11 . . . . 0.0 ?
C10 C11 N4 C12 . . . . 0.0 ?
Cl2 C11 N4 C12 . . . . 180.0 ?
N2 C4 O1 C5 . . . . 180.0 ?
C1 C4 O1 C5 . . . . 0.0 ?
C6 C5 O1 C4 6 . . . 90.53(16) ?
C6 C5 O1 C4 . . . . -90.53(16) ?
N3 C9 O2 C8 . . . . 0.0 ?
C10 C9 O2 C8 . . . . 180.0 ?
C7 C8 O2 C9 6 . . . 92.31(16) ?
C7 C8 O2 C9 . . . . -92.31(16) ?
