#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221522.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_2221522
loop_
_publ_author_name
'Hassan, Noor Doha'
'Tajuddin, Hairul Anuar'
'Abdullah, Zanariah'
'Ng, Seik Weng'
_publ_section_title
;
 1-Naphthyl quinoxalin-2-yl ether
;
_journal_coeditor_code           TK2386
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o731
_journal_paper_doi               10.1107/S1600536809007867
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H12 N2 O'
_chemical_formula_moiety         'C18 H12 N2 O'
_chemical_formula_sum            'C18 H12 N2 O'
_chemical_formula_weight         272.30
_chemical_name_systematic
;
1-Naphthyl quinoxalin-2-yl ether
;
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2758(6)
_cell_length_b                   18.5123(6)
_cell_length_c                   7.7947(3)
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      21.2
_cell_measurement_theta_min      2.2
_cell_volume                     2637.16(16)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      118(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.071
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12370
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1626
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.038
_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)+(0.046P)²+0.5804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.079
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                1316
_reflns_number_total             1626
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2386.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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        2637.2(2)
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               2221522
_cod_database_fobs_code          2221522
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+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, 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 0.19391(9) 0.24366(9) 0.5000(2) 0.0217(4) Uani d . 1 . .
N N1 0.15328(11) 0.34927(11) 0.3713(3) 0.0192(5) Uani d . 1 . .
N N2 0.30285(11) 0.38838(11) 0.3387(3) 0.0218(5) Uani d . 1 . .
C C1 0.12235(13) 0.21546(12) 0.4887(4) 0.0192(5) Uani d . 1 . .
C C2 0.07744(14) 0.22066(13) 0.6269(4) 0.0222(6) Uani d . 1 . .
H H2 0.0930 0.2454 0.7273 0.027 Uiso calc R 1 . .
C C3 0.00734(14) 0.18873(13) 0.6196(3) 0.0234(6) Uani d . 1 . .
H H3 -0.0246 0.1922 0.7155 0.028 Uiso calc R 1 . .
C C4 -0.01480(14) 0.15306(13) 0.4762(3) 0.0231(6) Uani d . 1 . .
H H4 -0.0619 0.1314 0.4737 0.028 Uiso calc R 1 . .
C C5 0.03121(13) 0.14761(12) 0.3301(3) 0.0198(5) Uani d . 1 . .
C C6 0.00887(15) 0.11230(14) 0.1784(4) 0.0269(6) Uani d . 1 . .
H H6 -0.0381 0.0903 0.1737 0.032 Uiso calc R 1 . .
C C7 0.05358(16) 0.10925(15) 0.0388(4) 0.0301(7) Uani d . 1 . .
H H7 0.0375 0.0857 -0.0627 0.036 Uiso calc R 1 . .
C C8 0.12373(16) 0.14110(15) 0.0448(4) 0.0278(6) Uani d . 1 . .
H H8 0.1546 0.1388 -0.0531 0.033 Uiso calc R 1 . .
C C9 0.14764(14) 0.17502(13) 0.1890(4) 0.0219(6) Uani d . 1 . .
H H9 0.1952 0.1957 0.1917 0.026 Uiso calc R 1 . .
C C10 0.10190(13) 0.17973(13) 0.3355(3) 0.0180(5) Uani d . 1 . .
C C11 0.20655(14) 0.30943(13) 0.4253(3) 0.0189(5) Uani d . 1 . .
C C12 0.28187(14) 0.32836(13) 0.4113(3) 0.0213(6) Uani d . 1 . .
H H12 0.3178 0.2964 0.4560 0.026 Uiso calc R 1 . .
C C13 0.24804(15) 0.43279(12) 0.2773(3) 0.0190(5) Uani d . 1 . .
C C14 0.26686(14) 0.49812(13) 0.1965(4) 0.0232(6) Uani d . 1 . .
H H14 0.3168 0.5114 0.1841 0.028 Uiso calc R 1 . .
C C15 0.21262(15) 0.54275(14) 0.1356(4) 0.0247(6) Uani d . 1 . .
H H15 0.2253 0.5866 0.0798 0.030 Uiso calc R 1 . .
C C16 0.13869(15) 0.52397(13) 0.1552(4) 0.0231(6) Uani d . 1 . .
H H16 0.1017 0.5552 0.1123 0.028 Uiso calc R 1 . .
C C17 0.11934(14) 0.46108(13) 0.2357(3) 0.0212(6) Uani d . 1 . .
H H17 0.0691 0.4494 0.2501 0.025 Uiso calc R 1 . .
C C18 0.17350(13) 0.41378(13) 0.2971(3) 0.0190(5) Uani d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C11 O1 C1 . . 117.31(18) ?
C11 N1 C18 . . 115.4(2) ?
C12 N2 C13 . . 116.4(2) ?
C2 C1 O1 . . 119.0(2) ?
C2 C1 C10 . . 122.9(2) ?
O1 C1 C10 . . 118.1(2) ?
C1 C2 C3 . . 119.1(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 120.4(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 121.2(2) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 122.3(2) ?
C6 C5 C10 . . 118.8(2) ?
C4 C5 C10 . . 119.0(2) ?
C7 C6 C5 . . 121.0(2) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 120.0(3) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 120.8(3) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.3(2) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C1 C10 C9 . . 123.5(2) ?
C1 C10 C5 . . 117.4(2) ?
C9 C10 C5 . . 119.1(2) ?
N1 C11 O1 . . 121.3(2) ?
N1 C11 C12 . . 124.2(2) ?
O1 C11 C12 . . 114.5(2) ?
N2 C12 C11 . . 121.8(2) ?
N2 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
N2 C13 C14 . . 119.3(2) ?
N2 C13 C18 . . 120.8(2) ?
C14 C13 C18 . . 119.9(2) ?
C15 C14 C13 . . 119.7(2) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.5(2) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 120.3(2) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
N1 C18 C17 . . 119.6(2) ?
N1 C18 C13 . . 121.3(2) ?
C17 C18 C13 . . 119.1(2) ?
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 C11 . 1.369(3) ?
O1 C1 . 1.411(3) ?
N1 C11 . 1.292(3) ?
N1 C18 . 1.378(3) ?
N2 C12 . 1.304(3) ?
N2 C13 . 1.382(3) ?
C1 C2 . 1.358(4) ?
C1 C10 . 1.415(3) ?
C2 C3 . 1.412(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.360(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.419(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.411(4) ?
C5 C10 . 1.423(3) ?
C6 C7 . 1.362(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.412(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.360(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.418(3) ?
C9 H9 . 0.9500 ?
C11 C12 . 1.425(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.406(3) ?
C13 C18 . 1.415(4) ?
C14 C15 . 1.375(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.404(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.369(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.405(3) ?
C17 H17 . 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
C11 O1 C1 C2 . . . . -101.4(3) ?
C11 O1 C1 C10 . . . . 81.6(3) ?
O1 C1 C2 C3 . . . . -176.3(2) ?
C10 C1 C2 C3 . . . . 0.5(3) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -0.7(4) ?
C3 C4 C5 C6 . . . . -178.6(2) ?
C3 C4 C5 C10 . . . . 0.5(3) ?
C4 C5 C6 C7 . . . . 178.6(2) ?
C10 C5 C6 C7 . . . . -0.5(4) ?
C5 C6 C7 C8 . . . . 0.6(4) ?
C6 C7 C8 C9 . . . . 0.1(4) ?
C7 C8 C9 C10 . . . . -0.8(4) ?
C2 C1 C10 C9 . . . . 178.8(2) ?
O1 C1 C10 C9 . . . . -4.4(3) ?
C2 C1 C10 C5 . . . . -0.7(3) ?
O1 C1 C10 C5 . . . . 176.1(2) ?
C8 C9 C10 C1 . . . . -178.6(2) ?
C8 C9 C10 C5 . . . . 0.9(4) ?
C6 C5 C10 C1 . . . . 179.3(2) ?
C4 C5 C10 C1 . . . . 0.2(3) ?
C6 C5 C10 C9 . . . . -0.2(3) ?
C4 C5 C10 C9 . . . . -179.3(2) ?
C18 N1 C11 O1 . . . . -179.3(2) ?
C18 N1 C11 C12 . . . . -0.3(4) ?
C1 O1 C11 N1 . . . . 10.9(3) ?
C1 O1 C11 C12 . . . . -168.2(2) ?
C13 N2 C12 C11 . . . . 0.4(4) ?
N1 C11 C12 N2 . . . . -1.0(4) ?
O1 C11 C12 N2 . . . . 178.1(2) ?
C12 N2 C13 C14 . . . . -179.6(2) ?
C12 N2 C13 C18 . . . . 1.4(4) ?
N2 C13 C14 C15 . . . . -179.7(2) ?
C18 C13 C14 C15 . . . . -0.7(4) ?
C13 C14 C15 C16 . . . . 0.7(4) ?
C14 C15 C16 C17 . . . . 0.2(4) ?
C15 C16 C17 C18 . . . . -1.2(4) ?
C11 N1 C18 C17 . . . . -179.5(2) ?
C11 N1 C18 C13 . . . . 2.1(3) ?
C16 C17 C18 N1 . . . . -177.3(2) ?
C16 C17 C18 C13 . . . . 1.2(4) ?
N2 C13 C18 N1 . . . . -2.8(4) ?
C14 C13 C18 N1 . . . . 178.2(2) ?
N2 C13 C18 C17 . . . . 178.8(2) ?
C14 C13 C18 C17 . . . . -0.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741890
