#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220503.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_2220503
loop_
_publ_author_name
'Idris, Azila'
'Afiffin, Azhar'
'Abdullah, Zanariah'
'Ng, Seik Weng'
_publ_section_title
;
 Phenyl pyrazin-2-yl ether
;
_journal_coeditor_code           HB2867
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o7
_journal_paper_doi               10.1107/S1600536808040099
_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
;
Phenyl pyrazin-2-yl ether
;
_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                 94.382(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7040(10)
_cell_length_b                   8.557(2)
_cell_length_c                   17.595(4)
_cell_measurement_reflns_used    739
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      3.3
_cell_volume                     856.3(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, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4641
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.32
_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    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0462
_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)+(0.0572P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                1207
_reflns_number_total             1950
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2867.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        856.4(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220503
_cod_database_fobs_code          2220503
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 0.0900(2) 0.70888(14) 0.45704(7) 0.0301(3) Uani d . 1 . .
N N1 0.4770(3) 0.56153(17) 0.60955(8) 0.0281(4) Uani d . 1 . .
N N2 0.4352(3) 0.81790(16) 0.51088(8) 0.0252(4) Uani d . 1 . .
C C1 0.0879(3) 0.8138(2) 0.39557(9) 0.0244(4) Uani d . 1 . .
C C2 -0.1015(3) 0.9128(2) 0.38509(10) 0.0288(4) Uani d . 1 . .
H H2 -0.2208 0.9130 0.4199 0.035 Uiso calc R 1 . .
C C3 -0.1150(3) 1.0127(2) 0.32238(10) 0.0320(5) Uani d . 1 . .
H H3 -0.2447 1.0819 0.3140 0.038 Uiso calc R 1 . .
C C4 0.0604(3) 1.0112(2) 0.27248(10) 0.0309(5) Uani d . 1 . .
H H4 0.0520 1.0803 0.2301 0.037 Uiso calc R 1 . .
C C5 0.2481(3) 0.9097(2) 0.28386(10) 0.0298(5) Uani d . 1 . .
H H5 0.3672 0.9086 0.2489 0.036 Uiso calc R 1 . .
C C6 0.2641(3) 0.8093(2) 0.34580(9) 0.0266(4) Uani d . 1 . .
H H6 0.3927 0.7393 0.3539 0.032 Uiso calc R 1 . .
C C7 0.2816(3) 0.70451(19) 0.50838(9) 0.0225(4) Uani d . 1 . .
C C8 0.2987(3) 0.5762(2) 0.55764(10) 0.0279(4) Uani d . 1 . .
H H8 0.1799 0.4981 0.5537 0.033 Uiso calc R 1 . .
C C9 0.6367(3) 0.6767(2) 0.61232(10) 0.0275(4) Uani d . 1 . .
H H9 0.7686 0.6707 0.6486 0.033 Uiso calc R 1 . .
C C10 0.6149(3) 0.8027(2) 0.56430(9) 0.0274(4) Uani d . 1 . .
H H10 0.7311 0.8823 0.5690 0.033 Uiso calc R 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
O1 0.0285(7) 0.0309(8) 0.0299(7) -0.0092(6) -0.0033(5) 0.0105(6)
N1 0.0356(9) 0.0253(8) 0.0237(8) -0.0023(7) 0.0037(7) 0.0021(7)
N2 0.0304(9) 0.0229(8) 0.0222(8) -0.0055(6) 0.0020(6) 0.0000(7)
C1 0.0279(10) 0.0230(10) 0.0215(9) -0.0088(8) -0.0028(7) 0.0039(8)
C2 0.0233(10) 0.0323(11) 0.0307(10) -0.0049(8) 0.0021(7) 0.0031(9)
C3 0.0267(11) 0.0321(11) 0.0362(10) -0.0007(8) -0.0041(8) 0.0044(9)
C4 0.0338(11) 0.0344(11) 0.0237(9) -0.0062(9) -0.0037(8) 0.0068(9)
C5 0.0316(11) 0.0368(11) 0.0209(9) -0.0056(9) 0.0011(8) -0.0027(9)
C6 0.0280(10) 0.0256(10) 0.0255(9) -0.0014(8) -0.0020(8) -0.0032(8)
C7 0.0253(10) 0.0224(10) 0.0203(8) -0.0029(7) 0.0043(7) -0.0007(8)
C8 0.0319(11) 0.0246(10) 0.0274(10) -0.0060(8) 0.0048(8) 0.0015(8)
C9 0.0315(11) 0.0287(10) 0.0219(9) -0.0001(8) -0.0011(7) 0.0005(8)
C10 0.0295(10) 0.0287(11) 0.0238(9) -0.0076(8) 0.0003(7) -0.0011(9)
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 . . 119.11(13) ?
C8 N1 C9 . . 116.18(15) ?
C7 N2 C10 . . 115.21(15) ?
C2 C1 C6 . . 122.28(16) ?
C2 C1 O1 . . 117.23(15) ?
C6 C1 O1 . . 120.38(16) ?
C1 C2 C3 . . 118.68(17) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 119.90(18) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.36(17) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.49(17) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 118.29(17) ?
C1 C6 H6 . . 120.9 ?
C5 C6 H6 . . 120.9 ?
N2 C7 O1 . . 120.23(15) ?
N2 C7 C8 . . 123.24(16) ?
O1 C7 C8 . . 116.52(15) ?
N1 C8 C7 . . 121.13(16) ?
N1 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
N1 C9 C10 . . 121.80(16) ?
N1 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
N2 C10 C9 . . 122.43(17) ?
N2 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
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 . 1.364(2) ?
O1 C1 . 1.4050(19) ?
N1 C8 . 1.320(2) ?
N1 C9 . 1.340(2) ?
N2 C7 . 1.306(2) ?
N2 C10 . 1.343(2) ?
C1 C2 . 1.374(3) ?
C1 C6 . 1.383(2) ?
C2 C3 . 1.394(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.398(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.370(2) ?
C9 H9 . 0.9500 ?
C10 H10 . 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 . . . . -126.78(17) ?
C7 O1 C1 C6 . . . . 56.9(2) ?
C6 C1 C2 C3 . . . . -0.5(3) ?
O1 C1 C2 C3 . . . . -176.75(15) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . 0.8(3) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
O1 C1 C6 C5 . . . . 176.75(14) ?
C4 C5 C6 C1 . . . . 0.0(3) ?
C10 N2 C7 O1 . . . . 179.05(14) ?
C10 N2 C7 C8 . . . . 0.5(2) ?
C1 O1 C7 N2 . . . . 15.5(2) ?
C1 O1 C7 C8 . . . . -165.92(14) ?
C9 N1 C8 C7 . . . . 0.6(2) ?
N2 C7 C8 N1 . . . . -1.1(3) ?
O1 C7 C8 N1 . . . . -179.72(15) ?
C8 N1 C9 C10 . . . . 0.4(3) ?
C7 N2 C10 C9 . . . . 0.5(2) ?
N1 C9 C10 N2 . . . . -1.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 413629
