#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220651.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_2220651
loop_
_publ_author_name
'Shah Bakhtiar, Nasir'
'Abdullah, Zanariah'
'Ng, Seik Weng'
_publ_section_title
;
 2-Phenoxypyrimidine
;
_journal_coeditor_code           TK2342
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o114
_journal_paper_doi               10.1107/S1600536808041196
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H8 N2 O'
_chemical_formula_moiety         'C10 H8 N2 O'
_chemical_formula_sum            'C10 H8 N2 O'
_chemical_formula_weight         172.18
_chemical_name_systematic
;
2-Phenoxypyrimidine
;
_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
_cell_angle_beta                 106.637(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8590(10)
_cell_length_b                   20.181(2)
_cell_length_c                   8.1339(8)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.2
_cell_volume                     1707.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2  (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω 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  0.024
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9752
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.2571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.102
_reflns_number_gt                3026
_reflns_number_total             3901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2342.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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_cell_volume        1707.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220651
_cod_database_fobs_code          2220651
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
O O1 0.69295(8) 0.58216(5) 0.51546(11) 0.0274(2) Uani d . 1 . .
O O2 0.97744(9) 0.67233(5) 0.77250(11) 0.0281(2) Uani d . 1 . .
N N1 0.59037(10) 0.60351(5) 0.72195(13) 0.0245(2) Uani d . 1 . .
N N2 0.77301(10) 0.53229(5) 0.76936(14) 0.0253(2) Uani d . 1 . .
N N3 1.05326(11) 0.62385(5) 1.03911(13) 0.0264(3) Uani d . 1 . .
N N4 0.87443(10) 0.69812(5) 0.96601(13) 0.0247(2) Uani d . 1 . .
C C1 0.59965(12) 0.62116(6) 0.40077(16) 0.0213(3) Uani d . 1 . .
C C2 0.48239(12) 0.59386(6) 0.31580(17) 0.0256(3) Uani d . 1 . .
H H2 0.4617 0.5500 0.3408 0.031 Uiso calc R 1 . .
C C3 0.39513(13) 0.63124(7) 0.19343(18) 0.0297(3) Uani d . 1 . .
H H3 0.3136 0.6133 0.1346 0.036 Uiso calc R 1 . .
C C4 0.42700(14) 0.69480(7) 0.15706(17) 0.0311(3) Uani d . 1 . .
H H4 0.3671 0.7204 0.0729 0.037 Uiso calc R 1 . .
C C5 0.54526(14) 0.72141(6) 0.24218(18) 0.0314(3) Uani d . 1 . .
H H15A 0.5666 0.7650 0.2161 0.038 Uiso calc R 1 . .
C C6 0.63298(13) 0.68443(6) 0.36592(17) 0.0263(3) Uani d . 1 . .
H H6B 0.7144 0.7024 0.4254 0.032 Uiso calc R 1 . .
C C7 0.68331(12) 0.57302(6) 0.67684(16) 0.0208(3) Uani d . 1 . .
C C8 0.58755(14) 0.59106(7) 0.88258(17) 0.0303(3) Uani d . 1 . .
H H8 0.5227 0.6115 0.9225 0.036 Uiso calc R 1 . .
C C9 0.67458(14) 0.54993(7) 0.99239(17) 0.0295(3) Uani d . 1 . .
H H9 0.6711 0.5416 1.1059 0.035 Uiso calc R 1 . .
C C10 0.76711(13) 0.52151(6) 0.92888(17) 0.0267(3) Uani d . 1 . .
H H10 0.8291 0.4931 1.0015 0.032 Uiso calc R 1 . .
C C11 1.07433(12) 0.63814(6) 0.72453(15) 0.0235(3) Uani d . 1 . .
C C12 1.05906(12) 0.57148(6) 0.68472(15) 0.0235(3) Uani d . 1 . .
H H12 0.9859 0.5480 0.6954 0.028 Uiso calc R 1 . .
C C13 1.15275(12) 0.53963(6) 0.62894(15) 0.0239(3) Uani d . 1 . .
H H13 1.1439 0.4939 0.6007 0.029 Uiso calc R 1 . .
C C14 1.25931(13) 0.57413(7) 0.61407(16) 0.0258(3) Uani d . 1 . .
H H14 1.3239 0.5518 0.5773 0.031 Uiso calc R 1 . .
C C15 1.27177(13) 0.64082(7) 0.65256(18) 0.0298(3) Uani d . 1 . .
H H15 1.3445 0.6644 0.6409 0.036 Uiso calc R 1 . .
C C16 1.17853(13) 0.67363(6) 0.70825(17) 0.0284(3) Uani d . 1 . .
H H16 1.1865 0.7196 0.7345 0.034 Uiso calc R 1 . .
C C17 0.96950(12) 0.66360(6) 0.93451(15) 0.0214(3) Uani d . 1 . .
C C18 1.03893(14) 0.61819(7) 1.19692(17) 0.0302(3) Uani d . 1 . .
H H18 1.0957 0.5900 1.2774 0.036 Uiso calc R 1 . .
C C19 0.94557(14) 0.65152(7) 1.24657(16) 0.0293(3) Uani d . 1 . .
H H19 0.9368 0.6472 1.3590 0.035 Uiso calc R 1 . .
C C20 0.86503(13) 0.69161(6) 1.12499(17) 0.0271(3) Uani d . 1 . .
H H20 0.7999 0.7157 1.1560 0.033 Uiso calc R 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'
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
C7 O1 C1 . . 118.48(9) ?
C17 O2 C11 . . 117.86(9) ?
C7 N1 C8 . . 114.61(11) ?
C7 N2 C10 . . 114.78(11) ?
C17 N3 C18 . . 114.85(11) ?
C17 N4 C20 . . 114.51(11) ?
C2 C1 C6 . . 121.77(12) ?
C2 C1 O1 . . 119.74(11) ?
C6 C1 O1 . . 118.26(11) ?
C1 C2 C3 . . 119.11(12) ?
C1 C2 H2 . . 120.4 ?
C3 C2 H2 . . 120.4 ?
C4 C3 C2 . . 119.85(13) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.48(13) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.05(12) ?
C4 C5 H15A . . 120.0 ?
C6 C5 H15A . . 120.0 ?
C1 C6 C5 . . 118.74(12) ?
C1 C6 H6B . . 120.6 ?
C5 C6 H6B . . 120.6 ?
N1 C7 N2 . . 128.65(11) ?
N1 C7 O1 . . 118.78(11) ?
N2 C7 O1 . . 112.56(10) ?
N1 C8 C9 . . 122.86(12) ?
N1 C8 H8 . . 118.6 ?
C9 C8 H8 . . 118.6 ?
C8 C9 C10 . . 116.48(12) ?
C8 C9 H9 . . 121.8 ?
C10 C9 H9 . . 121.8 ?
N2 C10 C9 . . 122.61(12) ?
N2 C10 H10 . . 118.7 ?
C9 C10 H10 . . 118.7 ?
C16 C11 C12 . . 122.03(12) ?
C16 C11 O2 . . 118.22(11) ?
C12 C11 O2 . . 119.62(12) ?
C11 C12 C13 . . 118.57(12) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C12 C13 C14 . . 120.38(12) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 120.04(12) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.37(12) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C11 C16 C15 . . 118.61(12) ?
C11 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
N3 C17 N4 . . 128.48(11) ?
N3 C17 O2 . . 118.70(11) ?
N4 C17 O2 . . 112.82(10) ?
N3 C18 C19 . . 122.58(12) ?
N3 C18 H18 . . 118.7 ?
C19 C18 H18 . . 118.7 ?
C18 C19 C20 . . 116.58(12) ?
C18 C19 H19 . . 121.7 ?
C20 C19 H19 . . 121.7 ?
N4 C20 C19 . . 123.00(12) ?
N4 C20 H20 . . 118.5 ?
C19 C20 H20 . . 118.5 ?
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
O1 C7 . 1.3590(15) ?
O1 C1 . 1.4053(15) ?
O2 C17 . 1.3565(14) ?
O2 C11 . 1.4037(15) ?
N1 C7 . 1.3205(16) ?
N1 C8 . 1.3394(17) ?
N2 C7 . 1.3307(16) ?
N2 C10 . 1.3352(17) ?
N3 C17 . 1.3235(16) ?
N3 C18 . 1.3414(17) ?
N4 C17 . 1.3297(16) ?
N4 C20 . 1.3324(16) ?
C1 C2 . 1.3780(18) ?
C1 C6 . 1.3785(17) ?
C2 C3 . 1.3848(19) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3824(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.389(2) ?
C5 H15A . 0.9500 ?
C6 H6B . 0.9500 ?
C8 C9 . 1.3771(19) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3793(19) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C16 . 1.3772(19) ?
C11 C12 . 1.3824(18) ?
C12 C13 . 1.3850(17) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3851(18) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3797(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3897(19) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 C19 . 1.3703(19) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3792(18) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
C7 O1 C1 C2 . . . . -80.80(14) ?
C7 O1 C1 C6 . . . . 104.66(13) ?
C6 C1 C2 C3 . . . . -0.72(19) ?
O1 C1 C2 C3 . . . . -175.06(11) ?
C1 C2 C3 C4 . . . . 0.64(19) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C3 C4 C5 C6 . . . . -0.3(2) ?
C2 C1 C6 C5 . . . . 0.28(18) ?
O1 C1 C6 C5 . . . . 174.70(11) ?
C4 C5 C6 C1 . . . . 0.24(19) ?
C8 N1 C7 N2 . . . . -0.11(19) ?
C8 N1 C7 O1 . . . . 179.36(11) ?
C10 N2 C7 N1 . . . . -0.22(19) ?
C10 N2 C7 O1 . . . . -179.71(10) ?
C1 O1 C7 N1 . . . . -3.06(16) ?
C1 O1 C7 N2 . . . . 176.49(10) ?
C7 N1 C8 C9 . . . . 0.14(19) ?
N1 C8 C9 C10 . . . . 0.1(2) ?
C7 N2 C10 C9 . . . . 0.52(18) ?
C8 C9 C10 N2 . . . . -0.5(2) ?
C17 O2 C11 C16 . . . . -106.60(13) ?
C17 O2 C11 C12 . . . . 77.48(15) ?
C16 C11 C12 C13 . . . . 0.84(19) ?
O2 C11 C12 C13 . . . . 176.60(10) ?
C11 C12 C13 C14 . . . . 0.14(18) ?
C12 C13 C14 C15 . . . . -0.92(19) ?
C13 C14 C15 C16 . . . . 0.7(2) ?
C12 C11 C16 C15 . . . . -1.03(19) ?
O2 C11 C16 C15 . . . . -176.84(11) ?
C14 C15 C16 C11 . . . . 0.23(19) ?
C18 N3 C17 N4 . . . . 0.05(19) ?
C18 N3 C17 O2 . . . . 179.77(11) ?
C20 N4 C17 N3 . . . . 0.79(19) ?
C20 N4 C17 O2 . . . . -178.94(11) ?
C11 O2 C17 N3 . . . . 0.36(17) ?
C11 O2 C17 N4 . . . . -179.88(10) ?
C17 N3 C18 C19 . . . . -0.63(19) ?
N3 C18 C19 C20 . . . . 0.3(2) ?
C17 N4 C20 C19 . . . . -1.10(19) ?
C18 C19 C20 N4 . . . . 0.6(2) ?
