#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227498.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227498
loop_
_publ_author_name
'Nasir, Shah Bakhtiar'
'Abdullah, Zanariah'
'Mainal, Azizah'
'Fairuz, Zainal A.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-(4-Methoxyphenoxy)pyrazine
;
_journal_coeditor_code           HB5602
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2303
_journal_paper_doi               10.1107/S1600536810031946
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H10 N2 O2'
_chemical_formula_moiety         'C11 H10 N2 O2'
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_chemical_name_systematic
;
2-(4-Methoxyphenoxy)pyrazine
;
_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                 97.109(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8783(2)
_cell_length_b                   10.9298(4)
_cell_length_c                   15.6430(6)
_cell_measurement_reflns_used    1293
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.3
_cell_volume                     997.32(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5515
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.12
_refine_ls_extinction_coef       0.042(4)
_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   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.087
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                1244
_reflns_number_total             1743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5602.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227498
_cod_database_fobs_code          2227498
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 0.80138(19) 0.41576(11) 0.38163(8) 0.0650(4) Uani d . 1 . .
O O2 0.0132(2) 0.59432(11) 0.19506(8) 0.0638(4) Uani d . 1 . .
N N1 0.6059(2) 0.26379(12) 0.44535(9) 0.0494(4) Uani d . 1 . .
N N2 1.0286(2) 0.18218(14) 0.52555(9) 0.0599(4) Uani d . 1 . .
C C1 0.7989(3) 0.31704(15) 0.43404(10) 0.0442(4) Uani d . 1 . .
C C2 1.0109(3) 0.27760(17) 0.47408(11) 0.0544(5) Uani d . 1 . .
H H2 1.1426 0.3197 0.4642 0.065 Uiso calc R 1 . .
C C3 0.8320(3) 0.12604(17) 0.53716(12) 0.0579(5) Uani d . 1 . .
H H3 0.8364 0.0578 0.5729 0.069 Uiso calc R 1 . .
C C4 0.6268(3) 0.16632(15) 0.49808(12) 0.0559(5) Uani d . 1 . .
H H4 0.4948 0.1247 0.5082 0.067 Uiso calc R 1 . .
C C5 0.5920(3) 0.45725(15) 0.33748(11) 0.0489(4) Uani d . 1 . .
C C6 0.5262(3) 0.41868(15) 0.25481(12) 0.0548(5) Uani d . 1 . .
H H6 0.6122 0.3603 0.2299 0.066 Uiso calc R 1 . .
C C7 0.3328(3) 0.46665(16) 0.20906(11) 0.0554(5) Uani d . 1 . .
H H7 0.2881 0.4407 0.1529 0.066 Uiso calc R 1 . .
C C8 0.2035(3) 0.55333(14) 0.24574(10) 0.0458(4) Uani d . 1 . .
C C9 0.2718(3) 0.59135(15) 0.32910(11) 0.0516(5) Uani d . 1 . .
H H9 0.1863 0.6494 0.3547 0.062 Uiso calc R 1 . .
C C10 0.4674(3) 0.54303(16) 0.37434(10) 0.0548(5) Uani d . 1 . .
H H10 0.5145 0.5692 0.4303 0.066 Uiso calc R 1 . .
C C11 -0.1195(3) 0.68815(16) 0.22838(12) 0.0637(5) Uani d . 1 . .
H H11A -0.2509 0.7059 0.1875 0.096 Uiso calc R 1 . .
H H11B -0.0278 0.7606 0.2386 0.096 Uiso calc R 1 . .
H H11C -0.1691 0.6611 0.2815 0.096 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
C1 O1 C5 . . 118.56(12) ?
C8 O2 C11 . . 118.05(13) ?
C1 N1 C4 . . 114.95(14) ?
C2 N2 C3 . . 116.22(15) ?
N1 C1 O1 . . 120.72(14) ?
N1 C1 C2 . . 123.03(16) ?
O1 C1 C2 . . 116.26(14) ?
N2 C2 C1 . . 121.37(16) ?
N2 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
N2 C3 C4 . . 121.60(17) ?
N2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
N1 C4 C3 . . 122.83(16) ?
N1 C4 H4 . . 118.6 ?
C3 C4 H4 . . 118.6 ?
C10 C5 C6 . . 120.54(16) ?
C10 C5 O1 . . 119.79(16) ?
C6 C5 O1 . . 119.42(16) ?
C5 C6 C7 . . 119.64(16) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C6 C7 C8 . . 120.56(16) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
O2 C8 C9 . . 124.90(15) ?
O2 C8 C7 . . 115.92(15) ?
C9 C8 C7 . . 119.17(16) ?
C10 C9 C8 . . 119.77(15) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C5 C10 C9 . . 120.31(16) ?
C5 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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 C1 . 1.3563(19) ?
O1 C5 . 1.4096(19) ?
O2 C8 . 1.3639(18) ?
O2 C11 . 1.426(2) ?
N1 C1 . 1.3062(19) ?
N1 C4 . 1.344(2) ?
N2 C2 . 1.314(2) ?
N2 C3 . 1.341(2) ?
C1 C2 . 1.392(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.357(2) ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9300 ?
C5 C10 . 1.361(2) ?
C5 C6 . 1.370(2) ?
C6 C7 . 1.371(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.380(2) ?
C9 C10 . 1.378(2) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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
C9 H9 Cg1 3_666 0.93 2.87 3.6326(18) 140
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 N1 C1 O1 . . . . 179.38(14) ?
C4 N1 C1 C2 . . . . -0.8(2) ?
C5 O1 C1 N1 . . . . -2.0(2) ?
C5 O1 C1 C2 . . . . 178.13(14) ?
C3 N2 C2 C1 . . . . -0.2(2) ?
N1 C1 C2 N2 . . . . 0.8(3) ?
O1 C1 C2 N2 . . . . -179.37(15) ?
C2 N2 C3 C4 . . . . -0.3(3) ?
C1 N1 C4 C3 . . . . 0.3(2) ?
N2 C3 C4 N1 . . . . 0.3(3) ?
C1 O1 C5 C10 . . . . 90.59(19) ?
C1 O1 C5 C6 . . . . -95.10(18) ?
C10 C5 C6 C7 . . . . -0.2(3) ?
O1 C5 C6 C7 . . . . -174.50(14) ?
C5 C6 C7 C8 . . . . -0.2(3) ?
C11 O2 C8 C9 . . . . 3.5(2) ?
C11 O2 C8 C7 . . . . -176.93(14) ?
C6 C7 C8 O2 . . . . -179.41(15) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
O2 C8 C9 C10 . . . . 179.76(15) ?
C7 C8 C9 C10 . . . . 0.2(2) ?
C6 C5 C10 C9 . . . . 0.6(3) ?
O1 C5 C10 C9 . . . . 174.88(14) ?
C8 C9 C10 C5 . . . . -0.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745775
